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Sample records for oleanane triterpenoid cddo-me

  1. Inhibition of cell proliferation and induction of apoptosis by oleanane triterpenoid (CDDO-Me) in pancreatic cancer cells is associated with the suppression of hTERT gene expression and its telomerase activity

    International Nuclear Information System (INIS)

    Deeb, Dorrah; Gao, Xiaohua; Liu, Yongbo; Kim, Sahn-Ho; Pindolia, Kirit R.; Arbab, Ali S.; Gautam, Subhash C.

    2012-01-01

    Highlights: ► CDDO-Me inhibits hTERT gene expression. ► CDDO-Me inhibits hTERT protein expression. ► CDDO-Me inhibits hTERT telomerase activity. ► CDDO-Me inhibits hTERT regulatory proteins. -- Abstract: Methyl-2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oate (CDDO-Me) is a multifunctional oleanane synthetic triterpenoid with potent anti-inflammatory and antitumorigenic properties. The mechanisms of the antisurvival and apoptosis-inducing activities of CDDO-Me and related derivatives of oleanolic acid have been defined; however, to date, no study has been carried out on the effect of CDDOs on human telomerase reverse transcriptase (hTERT) gene or telomerase activity. Here we report for the first time that inhibition of cell proliferation and induction of apoptosis by CDDO-Me in pancreatic cancer cell lines is associated with the inhibition of hTERT gene expression, hTERT telomerase activity and a number of proteins that regulate hTERT expression and activity. Furthermore, abrogation or overexpression of hTERT protein altered the susceptibility of tumor cells to CDDO-Me. These findings suggest that telomerase (hTERT) is a relevant target of CDDO-Me in pancreatic cancer cells.

  2. Prevention of Prostate Cancer with Oleanane Synthetic Triterpenoid CDDO-Me in the TRAMP Mouse Model of Prostate Cancer

    International Nuclear Information System (INIS)

    Gao, Xiaohua; Deeb, Dorrah; Liu, Yongbo; Arbab, Ali S.; Divine, George W.; Dulchavsky, Scott A.; Gautam, Subhash C.

    2011-01-01

    2-Cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid (CDDO), a synthetic analog of oleanolic acid, and its C28 methyl ester derivative (CDDO-Me), have shown potent antitumorigenic activity against a wide range of cancer cell lines, including prostate cancer cells in vitro, and inhibited the development of liver and lung cancer in vivo. In the present study, we examined the efficacy of CDDO-Me in preventing the development and progression of prostate cancer in the transgenic adenocarinoma of the mouse prostate (TRAMP) model. CDDO-Me inhibited the growth of murine TRAMPC-1 prostate cancer cells by inducing apoptosis through the inhibition of antiapoptotic p-Akt, p-mTOR and NF-κB. Early intervention with CDDO-Me (7.5 mg/kg) initiated at five weeks of age for 20 wk inhibited the progression of the preneoplastic lesions (low-grade PIN and high-grade-PIN) to adenocarcinoma in the dorsolateral prostate (DLP) and ventral prostate (VP) lobes of TRAMP mice. Even delayed administration of CDDO-Me started at 12 wk of age for 12 wk inhibited the development of adenocarcimona of the prostate. Both early and late treatment with CDDO-Me inhibited the metastasis of tumor to the distant organs. Treatment with CDDO-Me inhibited the expression of prosurvival p-Akt and NF-κB in the prostate and knocking-down Akt in TRAMPC-1 tumor cells sensitized them to CDDO-Me. These findings indicated that Akt is a target for apoptoxicity in TRAMPC-1 cells in vitro and potentially a target of CDDO-Me for inhibition of prostate cancer in vivo

  3. CDDO-Me: A Novel Synthetic Triterpenoid for the Treatment of Pancreatic Cancer

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    Dorrah Deeb

    2010-10-01

    Full Text Available Pancreatic ductal adenocarcinoma (PDA is one of the most lethal human malignancy with dismal prognosis and few effective therapeutic options. Novel agents that are safe and effective are urgently needed. Oleanolic acid-derived synthetic triterpenoids are potent antitumorigenic agents, but their efficacy or the mechanism of action for pancreatic cancer has not been adequately investigated. In this study, we evaluated the antitumor activity and the mechanism of action of methyl-2-cyano-3,12-dioxooleana-1,9(11-dien-28-oate (CDDO-Me, a oleanane-derived synthetic triterpenoid for human pancreatic cancer cell lines. CDDO-Me inhibited the growth of both K-ras mutated (MiaPaca2, Panc1 and Capan2 and wild-type K-ras (BxPC3 pancreatic cancer cells at very low concentrations. The growth inhibitory activity of CDDO-Me was attributed to the induction of apoptosis characterized by increased annexin-V-FITC binding and cleavage of PARP-1 and procaspases-3, -8 and-9. In addition, CDDO-Me induced the loss of mitochondrial membrane potential and release of cytochrome C. The antitumor activity of CDDO-Me was associated with the inhibition of prosurvival p-Akt, NF-κB and mammalian target of rapamycin (mTOR signaling proteins and the downstream targets of Akt and mTOR, such as p-Foxo3a (Akt and p-S6K1, p-eIF-4E and p-4E-BP1 (mTOR. Silencing of Akt or mTOR with gene specific-siRNA sensitized the pancreatic cancer cells to CDDO-Me, demonstrating Akt and mTOR as molecular targets of CDDO-Me for its growth inhibitory and apoptosis-inducing activity.

  4. CDDO-Me: A Novel Synthetic Triterpenoid for the Treatment of Pancreatic Cancer

    International Nuclear Information System (INIS)

    Deeb, Dorrah; Gao, Xiaohua; Arbab, Ali S.; Barton, Kenneth; Dulchavsky, Scott A.; Gautam, Subhash C.

    2010-01-01

    Pancreatic ductal adenocarcinoma (PDA) is one of the most lethal human malignancy with dismal prognosis and few effective therapeutic options. Novel agents that are safe and effective are urgently needed. Oleanolic acid-derived synthetic triterpenoids are potent antitumorigenic agents, but their efficacy or the mechanism of action for pancreatic cancer has not been adequately investigated. In this study, we evaluated the antitumor activity and the mechanism of action of methyl-2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oate (CDDO-Me), a oleanane-derived synthetic triterpenoid for human pancreatic cancer cell lines. CDDO-Me inhibited the growth of both K-ras mutated (MiaPaca2, Panc1 and Capan2) and wild-type K-ras (BxPC3) pancreatic cancer cells at very low concentrations. The growth inhibitory activity of CDDO-Me was attributed to the induction of apoptosis characterized by increased annexin-V-FITC binding and cleavage of PARP-1 and procaspases-3, -8 and-9. In addition, CDDO-Me induced the loss of mitochondrial membrane potential and release of cytochrome C. The antitumor activity of CDDO-Me was associated with the inhibition of prosurvival p-Akt, NF-κB and mammalian target of rapamycin (mTOR) signaling proteins and the downstream targets of Akt and mTOR, such as p-Foxo3a (Akt) and p-S6K1, p-eIF-4E and p-4E-BP1 (mTOR). Silencing of Akt or mTOR with gene specific-siRNA sensitized the pancreatic cancer cells to CDDO-Me, demonstrating Akt and mTOR as molecular targets of CDDO-Me for its growth inhibitory and apoptosis-inducing activity

  5. Oleanane-type triterpenoid saponins from Lysimachia fortunei Maxim.

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    Zhang, Shu-Lin; Yang, Zi-Ni; He, Cui; Liao, Hai-Bing; Wang, Heng-Shan; Chen, Zhen-Feng; Liang, Dong

    2018-03-01

    Six previously undescribed oleanane-type triterpenoid saponins, fortunosides A-F, together with six known ones, were isolated from the aerial parts of Lysimachia fortunei Maxim. Their structures were established by spectroscopic data analyses (1D, 2D-NMR and HRESIMS) and chemical methods. All isolated triterpenoid saponins were evaluated for their cytotoxicity against four human liver cancer cell lines (SMMC-7721, Hep3B, HuH7, and SK-Hep-1). Three saponins with the aglycone protoprimulagenin A exhibited moderate cytotoxicity against all of the tested human cancer cell lines, with IC 50 values ranging from 4.76 to 15.12 μM. Copyright © 2018 Elsevier Ltd. All rights reserved.

  6. CDDO-Me protects normal lung and breast epithelial cells but not cancer cells from radiation.

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    Mariam El-Ashmawy

    Full Text Available Although radiation therapy is commonly used for treatment for many human diseases including cancer, ionizing radiation produces reactive oxygen species that can damage both cancer and healthy cells. Synthetic triterpenoids, including CDDO-Me, act as anti-inflammatory and antioxidant modulators primarily by inducing the transcription factor Nrf2 to activate downstream genes containing antioxidant response elements (AREs. In the present series of experiments, we determined if CDDO-Me can be used as a radioprotector in normal non-cancerous human lung and breast epithelial cells, in comparison to lung and breast cancer cell lines. A panel of normal non-cancerous, partially cancer progressed, and cancer cell lines from both lung and breast tissue was exposed to gamma radiation with and without pre-treatment with CDDO-Me. CDDO-Me was an effective radioprotector when given ∼18 hours before radiation in epithelial cells (average dose modifying factor (DMF = 1.3, and Nrf2 function was necessary for CDDO-Me to exert these radioprotective effects. CDDO-Me did not protect cancer lines tested from radiation-induced cytotoxicity, nor did it protect experimentally transformed human bronchial epithelial cells (HBECs with progressive oncogenic manipulations. CDDO-Me also protected human lymphocytes against radiation-induced DNA damage. A therapeutic window exists in which CDDO-Me protects normal cells from radiation by activating the Nrf2 pathway, but does not protect experimentally transformed or cancer cell lines. This suggests that use of this oral available, non-toxic class of drug can protect non-cancerous healthy cells during radiotherapy, resulting in better outcomes and less toxicity for patients.

  7. Cytotoxic oleanane-type triterpenoid saponins from the Rhizomes of Anemone rivularis var. flore-minore.

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    Wang, Xiaoyang; Wang, Minchang; Xu, Min; Wang, Yi; Tang, Haifeng; Sun, Xiaoli

    2014-02-18

    Phytochemical investigation of the n-BuOH extract of the rhizomes of Anemone rivularis var. flore-minore led to the isolation of five new oleanane-type triterpenoid saponins 1-5, together with five known saponins 6-10. Their structures were determined by the extensive use of 1D and 2D NMR experiments, along with ESIMS analyses and acid hydrolysis. The aglycone of 4 and 5 was determined as 21α-hydroxyoleanolic acid, which was reported in this genus for the first time. The cytotoxicity of these compounds was evaluated against four human cancer cell line, including HL-60 (promyelocytic leukemia), HepG2 (hepatocellular carcinoma), A549 (lung carcinoma) and HeLa (cervical carcinoma). The monodesmosidic saponins 6-8 exhibited cytotoxic activity toward all tested cancer cell lines, with IC50 values in the 7.25-22.38 μM range.

  8. Synthetic oleanane triterpenoids: multifunctional drugs with a broad range of applications for prevention and treatment of chronic disease.

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    Liby, Karen T; Sporn, Michael B

    2012-10-01

    We review the rationale for the use of synthetic oleanane triterpenoids (SOs) for prevention and treatment of disease, as well as extensive biological data on this topic resulting from both cell culture and in vivo studies. Emphasis is placed on understanding mechanisms of action. SOs are noncytotoxic drugs with an excellent safety profile. Several hundred SOs have now been synthesized and in vitro have been shown to: 1) suppress inflammation and oxidative stress and therefore be cytoprotective, especially at low nanomolar doses, 2) induce differentiation, and 3) block cell proliferation and induce apoptosis at higher micromolar doses. Animal data on the use of SOs in neurodegenerative diseases and in diseases of the eye, lung, cardiovascular system, liver, gastrointestinal tract, and kidney, as well as in cancer and in metabolic and inflammatory/autoimmune disorders, are reviewed. The importance of the cytoprotective Kelch-like erythroid cell-derived protein with CNC homology-associated protein 1/nuclear factor (erythroid-derived 2)-like 2/antioxidant response element (Keap1/Nrf2/ARE) pathway as a mechanism of action is explained, but interactions with peroxisome proliferator-activated receptor γ (PARPγ), inhibitor of nuclear factor-κB kinase complex (IKK), janus tyrosine kinase/signal transducer and activator of transcription (JAK/STAT), human epidermal growth factor receptor 2 (HER2)/ErbB2/neu, phosphatase and tensin homolog (PTEN), the phosphatidylinositol 3-kinase/protein kinase B (PI3K/Akt) pathway, mammalian target of rapamycin (mTOR), and the thiol proteome are also described. In these interactions, Michael addition of SOs to reactive cysteine residues in specific molecular targets triggers biological activity. Ultimately, SOs are multifunctional drugs that regulate the activity of entire networks. Recent progress in the earliest clinical trials with 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid (CDDO) methyl ester (bardoxolone methyl) is also

  9. Synthetic triterpenoid induces 15-PGDH expression and suppresses inflammation-driven colon carcinogenesis.

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    Choi, Sung Hee; Kim, Byung-Gyu; Robinson, Janet; Fink, Steve; Yan, Min; Sporn, Michael B; Markowitz, Sanford D; Letterio, John J

    2014-06-01

    Colitis-associated colon cancer (CAC) develops as a result of inflammation-induced epithelial transformation, which occurs in response to inflammatory cytokine-dependent downregulation of 15-hydroxyprostaglandin dehydrogenase (15-PGDH) and subsequent suppression of prostaglandin metabolism. Agents that both enhance 15-PGDH expression and suppress cyclooxygenase-2 (COX-2) production may more effectively prevent CAC. Synthetic triterpenoids are a class of small molecules that suppress COX-2 as well as inflammatory cytokine signaling. Here, we found that administration of the synthetic triterpenoid 2-cyano-3,12-dioxooleana-1,9(11)-dien-C28-methyl ester (CDDO-Me) suppresses CAC in mice. In a spontaneous, inflammation-driven intestinal neoplasia model, deletion of Smad4 specifically in T cells led to progressive production of inflammatory cytokines, including TNF-α, IFN-γ, iNOS, IL-6, IL-1β; as well as activation of STAT1 and STAT3; along with suppression of 15-PGDH expression. Oral administration of CDDO-Me to mice with SMAD4-deficient T cells increased survival and suppressed intestinal epithelial neoplasia by decreasing production of inflammatory mediators and increasing expression of 15-PGDH. Induction of 15-PGDH by CDDO-Me was dose dependent in epithelial cells and was abrogated following treatment with TGF-β signaling inhibitors in vitro. Furthermore, CDDO-Me-dependent 15-PGDH induction was not observed in Smad3-/- mice. Similarly, CDDO-Me suppressed azoxymethane plus dextran sodium sulfate-induced carcinogenesis in wild-type animals, highlighting the potential of small molecules of the triterpenoid family as effective agents for the chemoprevention of CAC in humans.

  10. Polyoxygenated ursane and oleanane triterpenes from Siphonodon celastrineus.

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    Kaweetripob, Wirongrong; Mahidol, Chulabhorn; Thongnest, Sanit; Prawat, Hunsa; Ruchirawat, Somsak

    2016-09-01

    Twenty polyoxygenated triterpenes, including nineteen ursanes and one oleanane, were characterized from the stem material of Siphonodon celastrineus (Celastraceae) through the application of spectroscopic techniques and chemical transformation. Three of the ursane-type triterpenoids possessed the rare 13,27-cyclopropane ring skeleton. Copyright © 2016 Elsevier Ltd. All rights reserved.

  11. Reaction of lupane and oleanane triterpenoids with Lawesson's reagent

    Czech Academy of Sciences Publication Activity Database

    Kvasnica, Miroslav; Rudovská, I.; Císařová, I.; Šarek, J.

    2008-01-01

    Roč. 64, č. 17 (2008), s. 3736-3743 ISSN 0040-4020 Grant - others:GA ČR(CZ) GP203/05/P025 Institutional research plan: CEZ:AV0Z40550506 Keywords : terpenoids * Lawesson's reagent * ketones * sulfur Subject RIV: CC - Organic Chemistry Impact factor: 2.897, year: 2008

  12. Lupane, friedelane, oleanane, and ursane triterpenes from the stem of Siphonodon celastrineus Griff.

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    Kaweetripob, Wirongrong; Mahidol, Chulabhorn; Prawat, Hunsa; Ruchirawat, Somsak

    2013-12-01

    Twenty-one triterpenes consisting of a lupane derivative, two friedelanes, an oleanane derivative, and 17 ursane-type triterpenoids, together with three known triterpenes, three sterols, a fatty acid, a sesquiterpene alkaloid, and a glycerol derivative, were isolated from the stem of Siphonodon celastrineus. Their structures were characterized by various spectroscopic techniques, as well as comparison with literature data. Twenty-seven metabolites of these were evaluated for cytotoxic activity against six human cancer cell lines. The biosynthetic formation of a 1,4-dioxane bridge is also discussed. Copyright © 2013 Elsevier Ltd. All rights reserved.

  13. Nonsterol Triterpenoids as Major Constituents of Olea europaea

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    Stiti, Naïm; Hartmann, Marie-Andrée

    2012-01-01

    Plant triterpenoids represent a large and structurally diverse class of natural products. A growing interest has been focused on triterpenoids over the past decade due to their beneficial effects on human health. We show here that these bioactive compounds are major constituents of several aerial parts (floral bud, leaf bud, stem, and leaf) of olive tree, a crop exploited so far almost exclusively for its fruit and oil. O. europaea callus cultures were analyzed as well. Twenty sterols and twenty-nine nonsteroidal tetra- and pentacyclic triterpenoids belonging to seven types of carbon skeletons (oleanane, ursane, lupane, taraxerane, taraxastane, euphane, and lanostane) were identified and quantified by GC and GC-MS as free and esterified compounds. The oleanane-type compounds, oleanolic acid and maslinic acid, were largely predominant in all the organs tested, whereas they are practically absent in olive oil. In floral buds, they represented as much as 2.7% of dry matter. In callus cultures, lanostane-type compounds were the most abundant triterpenoids. In all the tissues analyzed, free and esterified triterpene alcohols exhibited different distribution patterns of their carbon skeletons. Taken together, these data provide new insights into largely unknown triterpene secondary metabolism of Olea europaea. PMID:22523691

  14. Immunosuppressive potential of bardoxolone methyl using a modified murine local lymph node assay (LLNA).

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    Kitsukawa, Mika; Tsuchiyama, Hiromi; Maeda, Akihisa; Oshida, Keiyu; Miyamoto, Yohei

    2014-08-01

    2-Cyano-3, 12-dioxooleana-1, 9-dien-28-oic acid methyl ester (CDDO-Me; bardoxolone methyl) is one of the synthetic oleanane triterpenoids (SOs). It is known that it is the strongest Nrf2/ARE signaling inducer of SOs and slightly inhibits immune response. Little was known about the immunomodulatory action of CDDO-Me in vivo. We assessed its immunosuppressive potential by using the modified mouse lymph node assay (LLNA) including immunosuppression-related gene expression analysis. In the modified LLNA, CDDO-Me showed a significant decrease in lymph node weight and changes in expressions of the immunosuppression-related genes, Zfp459 and Fmo2. It has been already reported that a decrease in lymph node weight was induced by several types of immunosuppressive chemicals such as calcineurin inhibitors, antimetabolites, steroids, and alkylators. In addition, changes in Zfp459 and Fmo2 expression was reported in response after only treatment of antimetabolites. From these results, CDDO-Me is considered to have an immunosuppressive action and similar mechanism to antimetabolites.

  15. Cuspidate A, new anti-fungal triterpenoid saponin from Lepidagathis cuspidata.

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    Rattan, Rajeev; Inder Fozdar, Bharat; Gautam, Veena; Sharma, Ritika; Kumar, Dinesh; Sharma, Upendra

    2017-04-01

    One new triterpenoid saponin named cuspidate A (1) along with a known oleanane-based triterpenoid saponin clemontanoside-C were isolated from the roots of Lepidagathis cuspidata. The structure of new compound (1) was established after detailed analysis of spectroscopic data including 1D and 2D NMR spectra. This is the first report on clemontanoside-C from this genus. These saponins were found to be effective against the selected fungal strains Aspergillus flavus, Rhizopus stolinifer, Penicillum nodatum, Aspergillus fumigates. Compound 1 showed better activity, comparable to the synthetic drug, while compound 2 showed a moderate effect against all studied fungal strains.

  16. Quantitative determination for cytotoxic Friedo-nor-oleanane derivatives from five morphological types of Maytenus ilicifolia (Celastraceae) by reverse-phase high-performance liquid chromatography.

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    Buffa Filho, Waldemar; Corsino, Joaquim; Bolzani, da Silva Vanderlan; Furlan, Maysa; Pereira, Ana Maria S; França, Suzelei Castro

    2002-01-01

    Five different morphological types of Maytenus ilicifolia of the same age and harvested under the same conditions showed distinct accumulations of some friedo-nor-oleananes. A rapid, sensitive and reliable reverse-phase HPLC method (employing an external standard) was used for the determination of the cytotoxic triterpenoids, 20 alpha-hydroxymaytenin, 22 beta-hydroxymaytenin, maytenin, celastrol and pristimerin in each of the five types. Well resolved peaks with good detection response and linearity in the range 1.0-100 micrograms/mL were obtained.

  17. Triterpenoids from Arctium lappa.

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    Jeelani, S; Khuroo, M A

    2012-01-01

    Phytochemical investigation of the leaves of Arctium lappa led to the isolation of two triterpenoids, characterised by NMR, IR and MS as 3α-hydroxylanosta-5,15-diene and 3α-acetoxy-hop-22(29)-ene. 3α-hydroxylanosta-5,15-diene is a new triterpenoid and is isolated for the first time from this genus.

  18. Antimicrobial steroidal saponin and oleanane-type triterpenoid saponins from Paullinia pinnata.

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    Lunga, Paul K; Qin, Xu-Jie; Yang, Xing W; Kuiate, Jules-Roger; Du, Zhi Z; Gatsing, Donatien

    2014-10-02

    Paullinia pinnata L. (Sapindaceae) is an African woody vine, which is widely used in traditional medicine for the treatment of human malaria, erectile dysfunction and bacterial infections. A phytochemical investigation of its methanol leaf and stem extracts led to the isolation of seven compounds which were evaluated for their antimicrobial properties. The extracts were fractionated and compounds were isolated by chromatographic methods. Their structures were elucidated from their spectroscopic data in conjunction with those reported in literature. The antimicrobial activities of the crude extracts, fractions and compounds were evaluated against bacteria, yeasts and dermatophytes using the broth micro-dilution technique. Seven compounds: 2-O-methyl-L-chiro-inositol (1), β-sitosterol (2), friedelin (3), 3β-(β-D-Glucopyranosyloxy) stigmast-5-ene (4), (3β)-3-O-(2'-Acetamido-2'-deoxy-β-D-glucopyranosyl) oleanolic acid (5), (3β,16α-hydroxy)-3-O-(2'-Acetamido-2'-deoxy-β-D-glucopyranosyl) echinocystic acid (6) and (3β)-3-O-[β-D-glucopyranosyl-(1″-3')-2'-acetamido-2'-deoxy-β-D-galactopyranosyl]oleanolic acid (7) were isolated. Compounds 5 and 7 showed the best antibacterial and anti-yeast activities respectively (MIC value range of 0.78-6.25 and 1.56-6.25 μg/ml), while 6 exhibited the best anti-dermatophytic activity (MIC value range of 6.25-25 μg/ml). The results of the present findings could be considered interesting, taking into account the global disease burden of these susceptible microorganisms, in conjunction with the search for alternative and complementary medicines.

  19. Cytotoxic triterpenoid saponins from Clematis tangutica.

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    Zhao, Min; Da-Wa, Zhuo-Ma; Guo, Da-Le; Fang, Dong-Mei; Chen, Xiao-Zhen; Xu, Hong-Xi; Gu, Yu-Cheng; Xia, Bing; Chen, Lei; Ding, Li-Sheng; Zhou, Yan

    2016-10-01

    Eight previously undescribed oleanane-type triterpenoid saponins, clematangoticosides A-H, together with eight known saponins, were isolated from the whole plants of Clematis tangutica (Maxim.) Korsh. Their structures were elucidated by extensive spectroscopic analysis, in combination with chemical methods (acid hydrolysis and mild alkaline hydrolysis). Clematangoticosides D-G were found to be unusual 23, 28-bidesmosidic glycosides. The cytotoxic activities of all of the isolated saponins were evaluated against the four human cancer cell lines SGC-7901, HepG2, HL-60 and U251MG. Clematoside S, sapindoside B, kalopanax saponin A, and koelreuteria saponin A exhibited cytotoxicity against all of the test cancer cell lines with IC50 values in the range of 1.88-27.20 μM, while clematangoticoside D and F showed selective cytotoxicity against SGC-7901 with IC50 values of 24.22 and 21.35 μM, respectively. Copyright © 2016 Elsevier Ltd. All rights reserved.

  20. Triterpenoid Components from Oak Heartwood (Quercus robur) and Their Potential Health Benefits.

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    Pérez, Andy J; Pecio, Łukasz; Kowalczyk, Mariusz; Kontek, Renata; Gajek, Gabriela; Stopinsek, Lidija; Mirt, Ivan; Oleszek, Wiesław; Stochmal, Anna

    2017-06-14

    For centuries oak wood (Quercus robur) has been used in aging of wines and spirits, which is based on pleasant flavors given to beverages by phenolics transferred to the liquid during the maturation process. Other metabolites, such as triterpenoids, can also be released. Searching for extractable triterpenoids in oak heartwood, 12 new, 1-12, and five known, 13-17, oleanane types were isolated and characterized. Their cytotoxicities were tested against cancer cells (PC3 and MCF-7) and lymphocytes. Breast cancer cells (MCF-7) were the most affected by triterpenoids, with roburgenic acid, 4, being the most active compound (IC 50 = 19.7 μM). Selectivity was observed for compounds 1-3, 8, 9, and 16, exhibiting an IC 50 > 200 μM against lymphocytes, while active against cancer cells. A galloyl unit attached to the triterpenoid moiety was established as the key feature for such effect. These results highlight the occurrence of triterpenoids in oak heartwood and their relevance for chemoprevention of breast cancer.

  1. Candidate genes involved in the biosynthesis of triterpenoid saponins in Platycodon grandiflorum identified by transcriptome analysis

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    Chunhua eMa

    2016-05-01

    Full Text Available Background: Platycodon grandiflorum is the only species in the genus Platycodon of the family Campanulaceae, which has been traditionally used as a medicinal plant for its lung-heat-clearing, antitussive, and expectorant properties in China, Japanese and Korean. Oleanane-type triterpenoid saponins were the main chemical components of P. grandiflorum and platycodin D was the abundant and main bioactive component, but little is known about their biosynthesis in plants. Hence, P. grandiflorum is an ideal medicinal plant for studying the biosynthesis of Oleanane-type saponins. In addition, the genomic information of this important herbal plant is unavailable.Principal Findings:A total of 58,580,566 clean reads were obtained, which were assembled into 34,053 unigenes, with an average length of 936 bp and N50 of 1,661 bp by analyzing the transcriptome data of P. grandiflorum. Among these 34,053 unigenes, 22,409 unigenes (65.80% were annotated based on the information available from public databases, including Nr, NCBI, Swiss-Prot, KOG and KEGG. Furthermore, 21 candidate cytochrome P450 genes and 17 candidate UDP-glycosyltransferase genes most likely involved in triterpenoid saponins biosynthesis pathway were discovered from the transcriptome sequencing of P. grandiflorum. In addition, 10,626 SSRs were identified based on the transcriptome data, which would provide abundant candidates of molecular markers for genetic diversity and genetic map for this medicinal plant.Conclusion:The genomic data obtained from P. grandiflorum, especially the identification of putative genes involved in triterpenoid saponins biosynthesis pathway, will facilitate our understanding of the biosynthesis of triterpenoid saponins at molecular level.

  2. Triterpenoids from Tillandsia fasciculata.

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    Cantillo-Ciau, Z; Brito-Loeza, W; Quijano, L

    2001-07-01

    The leaves of Tillandsia fasciculata afforded four tetracyclic triterpenoids of the cycloartane type, two new compounds identified as cyclolaudenyl formate (2) and the (24S)-24-isopropenyl cycloartanone, which we named tillandsinone (1), and the known cyclolaudenone (3) and cyclolaudenol (4).

  3. [Study on the chemical composition of triterpenoid from the fruit of Buddleja lindleyana and their neuroprotective activitiy].

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    Wu, De-Ling; Wang, Yang-Kui; Wang, Xun-Cui; Liu, Jin-Song; Jin, Chuan-Shan; Zhang, Wei

    2011-12-01

    To study the chemical composition of triterpenoid from the fruit of Buddleja lindleyana. The chemical components were isolated by chromatography. The structures were identified by spectral data. The neuroprotective activity of these compounds were evaluated by using MPP+ induced injury in PC12 cells. 3 compounds were separated and identified as oleanane, alpha-L-msnnopyranoside derive (1), 13, 28-epoxy-3beta,23-dihydroxy-11-oleanene (2), 3, 23, 28-trihydroxyolean-11,13 (18)-diene (3). Compounds 1-3 showed obviously neuroprotective activity. The data of compound (1) is reported for the first time. The neuroprotective activities of compounds 1, 2, 3 are reported for the first time.

  4. Antibacterial triterpenoids from Melia toosendan

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    Qin Zhu

    2015-01-01

    Full Text Available A new lanostan-type triterpenoid with hydroperoxy group, toosendanin A (1, together with two known triterpenoids, meliastatin 3 (2 and ursolic acid (3, w ere isolated and identified from the stems of Melia toosendan. The structures of these compounds were elucidated by 1D- and 2D-NMR spectra and other spectroscopic studies. These compounds were assayed for the antibacterial activities against some hospital pathogenic bacteria. Toosendanin A (1 exhibited strong antibacterial activity against K. pneumoniae .

  5. Synthetic triterpenoids, CDDO-Imidazolide and CDDO-Ethyl amide, induce chondrogenesis.

    Science.gov (United States)

    Suh, N; Paul, S; Lee, H J; Yoon, T; Shah, N; Son, A I; Reddi, A H; Medici, D; Sporn, M B

    2012-05-01

    Novel methods for inducing chondrogenesis are critical for cartilage tissue engineering and regeneration. Here we show that the synthetic oleanane triterpenoids, CDDO-Imidazolide (CDDO-Im) and CDDO-Ethyl amide (CDDO-EA), at concentrations as low as 200 nM, induce chondrogenesis in organ cultures of newborn mouse calvaria. The cartilage phenotype was measured histologically with metachromatic toluidine blue staining for proteoglycans and by immunohistochemical staining for type II collagen. Furthermore, real-time polymerase chain reaction (PCR) analysis using mRNA from calvaria after 7-day treatment with CDDO-Im and CDDO-EA showed up-regulation of the chondrocyte markers SOX9 and type II collagen (alpha1). In addition, TGF-β; BMPs 2 and 4; Smads 3, 4, 6, and 7; and TIMPs-1 and -2 were increased. In contrast, MMP-9 was strongly down-regulated. Treatment of human bone marrow-derived mesenchymal stem cells with CDDO-Im and CDDO-EA (100 nM) induced expression of SOX9, collagen IIα1, and aggrecan, as well as BMP-2 and phospho-Smad5, confirming that the above triterpenoids induce chondrogenic differentiation. This is the first report of the use of these drugs for induction of chondrogenesis. Copyright © 2012 Osteoarthritis Research Society International. Published by Elsevier Ltd. All rights reserved.

  6. New triterpenoids from Gentiana lutea.

    Science.gov (United States)

    Toriumi, Yoshitaka; Kakuda, Rie; Kikuchi, Masafumi; Yaoita, Yasunori; Kikuchi, Masao

    2003-01-01

    Three new triterpenoids, 2,3-seco-3-oxours-12-en-2-oic acid, 2,3-seco-3-oxoolean-12-en-2-oic acid, and betulin 3-O-palmitate, have been isolated from the rhizomes and roots of Gentiana lutea, together with five known ones. The structures of the new compounds were determined by spectral and chemical methods.

  7. A structure-activity relationship study on antiosteoclastogenesis effect of triterpenoids from the leaves of loquat (Eriobotrya japonica).

    Science.gov (United States)

    Tan, Hui; Ashour, Ahmed; Katakura, Yoshinori; Shimizu, Kuniyoshi

    2015-04-15

    Our previous results elucidated that the leaves of Eriobotrya japonica possessed the potential to suppress ovariectomy-induced bone mineral density deterioration, and ursolic acid, the major bioactive component in these leaves, suppressed the osteoclast differentiation. The aim of this study was to discover more candidates for development of novel antiosteoclastogenesis agents from the leaves of E. japonica. Phytochemical analysis following a cell-based osteoclastic tartrate-resistant acid phosphatase (TRAP) activity assay revealed 11 more compounds with a potent antiosteoclastogenesis effect. The potency of ursane-type triterpenoids from the leaves of E. japonica prompted us to investigate the structure-activity relationships underlying their antiosteoclastogenesis. The results revealed that both the hydroxyl group at C-3 and the carboxylic group at C-17 played indispensable roles in the antiosteoclastogenesis activity of ursane-type triterpenoids. The configuration at C-3 (a beta-form of the hydroxyl group) was found to be important for this activity. While introducing a hydroxyl group at C-19 increased the inhibitory activity of ursane-type triterpenoids carrying an alpha-form hydroxyl group at C-3. The bioactivity analyses of ursolic acid and oleanolic acid demonstrated that the antiosteoclastogenesis effect of ursolic acid may be related to different positions of the C-29 and C-30 methyl groups on the E-ring, since oleanolic acid showed limited activity. The addition of a hydroxyl group at C-2 would dramatically improve the inhibition of oleanane-type triterpenoids. Collectively, these findings could provide important clues for the improvement of multi-targeted antiosteoclastogenesis agents from the leaves of E. japonica. Copyright © 2015 Elsevier GmbH. All rights reserved.

  8. Triterpenoid saponins from Dianthus versicolor.

    Science.gov (United States)

    Ma, Li; Gu, Yu-Cheng; Luo, Jian-Guang; Wang, Jun-Song; Huang, Xue-Feng; Kong, Ling-Yi

    2009-04-01

    Seven new pentacyclic triterpenoid saponins, named dianversicosides A-G (1-7), together with nine known compounds, were isolated from the aerial parts of Dianthus versicolor. The structures of 1-7 were elucidated on the basis of spectroscopic data and chemical evidence. The absolute configuration of the 3-hydroxyl-3-methylglutaryl (HMG) group in 1-4 was ascertained by chemical analysis combined with a chiral HPLC method. Cytotoxic activities of the isolated compounds were evaluated against a small panel of cancer and other cell lines.

  9. New Triterpenoid Saponins from Green Vegetable Soya Beans and Their Anti-Inflammatory Activities.

    Science.gov (United States)

    Lan, Xiuhua; Deng, Kejun; Zhao, Jianping; Chen, Yiyi; Xin, Xuhui; Liu, Yanli; Khan, Ikhlas A; Yang, Shilin; Wang, Taoyun; Xu, Qiongming

    2017-12-20

    Ten compounds were isolated and identified from green vegetable soya beans, of which five are new triterpenoid saponins (1-5) and five are known compounds (6-10). The chemical structures of the five triterpenoid saponins (1-5) were elucidated to be 3β,24-dihydroxy-22β,30-epoxy-30-oxoolean-12-en 3-O-α-l-rhamnopyranosyl-(1 → 2)-β-d-xylopyranosyl-(1 → 2)-β-d-glucuronopyranoside, 1; 3β,24-dihydroxy-22β,30-epoxy-30-oxoolean-12-en 3-O-α-l-rhamnopyranosyl-(1 → 2)-β-d-(3″-O-formyl)-galactopyranosyl-(1 → 2)-β-d-glucuronopyranoside, 2; 22-keto-3β,24-dihydroxy oleanane-12-ene 3-O-α-l-rhamnopyranosyl-(1 → 2)-β-d-(3″-O-formyl)-galactopyranosyl-(1 → 2)-β-d-glucuronopyranoside, 3; 3β,22β,24-trihydroxy oxyolean-18(19)-ene-29-acid 3-O-α-l-rhamnopyranosyl-(1 → 2)-β-d-galactopyranosyl-(1 → 2)-β-d-glucuronopyranoside, 4; and punicanolic acid 3-O-α-l-rhamnopyranosyl-(1 → 2)-β-d-galactopyranosyl-(1 → 2)-β-d-glucuronopyranoside, 5 from the spectroscopic data (IR, GTC/FID, HR-ESI-MS, and 1D and 2D NMR). The nitric oxide release inhibitions of compounds 1-10 in LPS-stimulated RAW264.7 cells were evaluated, and the data suggested that compounds 1, 2, and 5 might possess moderate anti-inflammatory activities, with IC 50 values of 18.8, 16.1, and 13.2 μM, respectively.

  10. Techniques for the analysis of pentacyclic triterpenoids in medicinal plants.

    Science.gov (United States)

    Xu, Congcong; Wang, Bing; Pu, Yiqiong; Tao, Jiansheng; Zhang, Tong

    2018-01-01

    Triterpenes are a major class of chemical compounds found in natural plants and can be categorized into acyclic triterpenoids, monocyclic triterpenoids, tricyclic triterpenoids, tetracyclic triterpenoids, and pentacyclic triterpenoids. Among them, pentacyclic triterpenoids have gained more extensive attention due to their biological activities, including anti-inflammation, antibacterial, antioxidation, antitumor, anti-HIV, hepatoprotection, and immunological adjuvant properties. In this review, we summarize the extraction and analytical methods for pentacyclic triterpenoids, where more than 56 triterpenes from 49 kinds of plants were involved. The analysis methods include gas chromatography, liquid chromatography, capillary electrophoresis, thin-layer chromatography, supercritical fluid chromatography, NMR spectroscopy, and X-ray spectroscopy. This review provides valuable reference for the determination of pentacyclic triterpenoids in medicinal plants. © 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  11. Bioactive constituents of oleanane-type triterpene saponins from the roots of Glycyrrhiza glabra.

    Science.gov (United States)

    Wei, Juan-Hua; Zheng, Yun-Feng; Li, Cun-Yu; Tang, Yu-Ping; Peng, Guo-Ping

    2014-01-01

    Three new oleanane-type triterpene saponins, namely licorice-saponin M3 (1), licorice-saponin N4 (2), and licorice-saponin O4 (3), an artificial product (4), as well as five known triterpene glucuronides (5-9), were isolated from the roots of Glycyrrhiza glabra L. Their structures were established using 1D and 2D NMR spectroscopy, mass spectrometry, and by comparison with spectroscopic data reported in the literature. The inhibitory effects of the selected compounds on neuraminidase were evaluated, and the preliminary structure-activity relationship was also predicted.

  12. Triterpenoid Saponins from Stauntonia chinensis

    Energy Technology Data Exchange (ETDEWEB)

    Chen, Yu [South Central Univ. for Nationalities, Wuhan (China); Yang, Fang; Wang, Sha; Wang, Debin; Xu, Jing; Yang, Guangzhong [South Central Univ. for Nationalities, Wuhan (China)

    2014-04-15

    The chemical constituents of S. chinensis were previously reported to contain nortriterpenoid saponins, neolignan glycosides, flavonoids. To find the biologically active compounds, a detailed phytochemical investigation was carried out on the stem of S. chinensis, which resulted in isolation of two new triterpenoid saponins, named as yemuo-side YM. Their structues were established on the basis of 2D-NMR experiments and mass spectrometry. In addition, eight known triterpene glycoside 3-O-α-L-arabinopyranosyl-30-norhederagenin, sinofoside A, yemuoside YM11, 3-O-α-L-arabinopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranos yl-akebonic acid, 3-O-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl-hederagenin, 3-O-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl hederagenin, hederasaponin D and 28-O-β-D-glucopyranosyl-(16)-β-D-glucopyranosyl-hederagenin were isolated from this plant. Compounds and were isolated from thisplant for the first time.

  13. Triterpenoid Saponins from Stauntonia chinensis

    International Nuclear Information System (INIS)

    Chen, Yu; Yang, Fang; Wang, Sha; Wang, Debin; Xu, Jing; Yang, Guangzhong

    2014-01-01

    The chemical constituents of S. chinensis were previously reported to contain nortriterpenoid saponins, neolignan glycosides, flavonoids. To find the biologically active compounds, a detailed phytochemical investigation was carried out on the stem of S. chinensis, which resulted in isolation of two new triterpenoid saponins, named as yemuo-side YM. Their structues were established on the basis of 2D-NMR experiments and mass spectrometry. In addition, eight known triterpene glycoside 3-O-α-L-arabinopyranosyl-30-norhederagenin, sinofoside A, yemuoside YM11, 3-O-α-L-arabinopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranos yl-akebonic acid, 3-O-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl-hederagenin, 3-O-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl hederagenin, hederasaponin D and 28-O-β-D-glucopyranosyl-(16)-β-D-glucopyranosyl-hederagenin were isolated from this plant. Compounds and were isolated from thisplant for the first time

  14. Triterpenoid saponins from Echinopsis macrogona (Cactaceae).

    Science.gov (United States)

    Okazaki, Sachie; Kinoshita, Kaoru; Ito, Satoru; Koyama, Kiyotaka; Yuasa, Hiroshi; Takahashi, Kunio

    2011-01-01

    Triterpene saponins, pachanosides C1, E1, F1 and G1 (1-4), and bridgesides A1, C1, C2, D1, D2, E1 and E2 (5-11) were isolated from Echinopsis macrogona. Compounds 1-4 were saponins with pachanane type triterpene saponins, while the others (5-11) were oleanane type triterpene saponins. While the aglycones of 2-4 and 8-11 were hitherto unknown, the structure of pachanol C was revised in this paper. Their structures were elucidated on the basis of chemical and physicochemical evidence. Copyright © 2010 Elsevier Ltd. All rights reserved.

  15. Occurrence and biogenesis of seco-triterpenoids

    DEFF Research Database (Denmark)

    Almeida Robles, Aldo Ricardo

    Triterpenoids are secondary metabolites synthesized by oxidosqualene cyclases (OSCs), a class of enzyme that converts the linear squalene-2,3-oxide to single or multi-ring products in a dynamic process called cyclization. The cyclization cascade is powered by a migrating carbocation that through...... process of an OSC or from post cyclization modification steps. The bioactivity and biosynthesis of the seco-triterpenoids is intriguing, and yet underexplored. In this thesis a review of structure-activity relationships of seco-triterpenoids is presented. Seco-cycloartanes report the highest cytotoxicity...... OSCs in O. spinosa (OsONS1 and OsONS2) which both are able to produce α-onocerin. Contrary to the α-onocerin pathway in L. clavatum in which two different cyclases are needed for α-onocerin synthesis. Moreover, an OSC phylogenetic analysis indicated the onocerin synthases of O. spinosa arose from...

  16. Three new triterpenoids from Ganoderma theaecolum.

    Science.gov (United States)

    Liu, Li-Ying; Yan, Zheng; Kang, Jie; Chen, Ruo-Yun; Yu, De-Quan

    2017-09-01

    Three new triterpenoids (1-3), together with four known triterpenoids (4-7), were isolated from the fruiting bodies of Ganoderma theaecolum. Their structures were elucidated on the basis of their spectroscopic data and chemical evidence. Compounds 4 and 6 exhibited antitumor activities against H460 cells with IC 50 values of 22.4 and 43.1 μM, respectively. And the cytotoxic activities of compounds 4 and 5 against MDA-MB-231 cancer cell lines were assayed with IC 50 values of 49.1 and 75.8 μM, respectively.

  17. Microbial-Catalyzed Biotransformation of Multifunctional Triterpenoids Derived from Phytonutrients

    Science.gov (United States)

    Shah, Syed Adnan Ali; Tan, Huey Ling; Sultan, Sadia; Mohd Faridz, Muhammad Afifi Bin; Mohd Shah, Mohamad Azlan Bin; Nurfazilah, Sharifah; Hussain, Munawar

    2014-01-01

    Microbial-catalyzed biotransformations have considerable potential for the generation of an enormous variety of structurally diversified organic compounds, especially natural products with complex structures like triterpenoids. They offer efficient and economical ways to produce semi-synthetic analogues and novel lead molecules. Microorganisms such as bacteria and fungi could catalyze chemo-, regio- and stereospecific hydroxylations of diverse triterpenoid substrates that are extremely difficult to produce by chemical routes. During recent years, considerable research has been performed on the microbial transformation of bioactive triterpenoids, in order to obtain biologically active molecules with diverse structures features. This article reviews the microbial modifications of tetranortriterpenoids, tetracyclic triterpenoids and pentacyclic triterpenoids. PMID:25003642

  18. GC-MS Profiling of Triterpenoid Saponins from 28 Quinoa Varieties (Chenopodium quinoa Willd.) Grown in Washington State.

    Science.gov (United States)

    Medina-Meza, Ilce G; Aluwi, Nicole A; Saunders, Steven R; Ganjyal, Girish M

    2016-11-16

    Quinoa (Chenopodium quinoa Willd) contains 2 to 5% saponins in the form of oleanane-type triterpenoid glycosides or sapogenins found in the external layers of the seeds. These saponins confer an undesirable bitter flavor. This study maps the content and profile of glycoside-free sapogenins from 22 quinoa varieties and 6 original breeding lines grown in North America under similar agronomical conditions. Saponins were recovered using a novel extraction protocol and quantified by GC-MS. Oleanolic acid (OA), hederagenin (HD), serjanic acid (SA), and phytolaccagenic acid (PA) were identified by their mass spectra. Total saponin content ranged from 3.81 to 27.1 mg/g among the varieties studied. The most predominant sapogenin was phytolaccagenic acid with 16.72 mg/g followed by hederagenin at 4.22 mg/g representing the ∼70% and 30% of the total sapogenin content. Phytolaccagenic acid and the total sapogenin content had a positive correlation of r 2 = 0.88 (p quinoa in food products. The multivariate analysis showed no correlations between origin of seeds and saponin profile and/or content.

  19. Triterpenoidal saponins from the fruits of Gleditsia caspica with proapoptotic properties.

    Science.gov (United States)

    Shaheen, Usama; Ragab, Ehab A; Abdalla, Ashraf N; Bader, Ammar

    2018-01-01

    Three previously undescribed oleanane-type triterpenoidal saponins named caspicaosides L-N were isolated from the fruits of Gleditsia caspica Desf. The aglycons of these saponins were echinocystic acid, erythrodiol and 12-oleanene-3,28,30-triol. Caspicaoside L is a bisdesmosidic saponin acylated with two monoterpenic acids. It has a disaccharide moiety made up of glucose and arabinose attached to C-3 and pentasaccharide moiety linked to C-28 made up of one glucose, 2 xyloses, one inner rhamnose and one terminal rhamnose which was acylated with two identical monoterpenic acids. Caspicaoside M is a monodesmosidic saponin with a trisaccharide moiety at C-3 made up of glucose, xylose and arabinose, while caspicaoside N has a disaccharide moiety at C-3 made up of glucose and arabinose. Their structures were determined by extensive 1D and 2D (DQF-COSY, HSQC, TOCSY, 1 H- 13 C-HSQC-TOCSY, HMBC, ROESY, NOESY) NMR, HRESIMS analyses and chemical degradation. The cytotoxicity MTT-based assay showed that caspicaosides M, N and L, respectively, exhibited high cytotoxic activity with IC 50  ≤ 10 μM (72 h) at least against one of the three used cancer cell lines, MCF 7, A2780 and HT 29; and were 2-34 folds selective against the normal fibroblasts (MRC 5). All compounds also induced apoptosis and caused G 2 /M arrest in MCF 7 cells (24 h); thus showing pro-apoptotic properties. Copyright © 2017 Elsevier Ltd. All rights reserved.

  20. Pentacyclic triterpenoids from the leaves of Terminalia brasiliensis; Triterpenoides pentaciclicos das folhas de Terminalia brasiliensis

    Energy Technology Data Exchange (ETDEWEB)

    Araujo, Delton Servulo; Chaves, Mariana H. [Universidade Federal do Piaui, Teresina, PI (Brazil). Dept. de Quimica]. E-mail: mariana@ufpi.br

    2005-11-15

    Eleven oleanane, ursane and lupane-type triterpenes were isolated from the leaves of Terminalia brasiliensis Camb, daturadiol (3{beta},6{beta}-dihydroxy-olean-12-ene), 3{beta}-hydroxy-30-norlupan-20-one, lupenone, {beta}-amyrenone, {alpha}-amyrenone, lupeol, {beta}-amyrin, {alpha}-amyrin, betulin, erythrodiol and uvaol, in addition to squalene, sitosterol and {alpha}-tocopherol. The structures of these compounds were identified by {sup 1}H and {sup 13}C NMR spectral analysis and comparison with literature data. (author)

  1. Ceanothane-type triterpenoids from Cyphostemma adenocaule.

    Science.gov (United States)

    Chouna, Jean Rodolphe; Nardella, Flore; Lenta, Bruno Ndjakou; Vonthron-Sénécheau, Catherine; Nkeng-Efouet-Alango, Pépin; Sewald, Norbert

    2016-07-26

    Phytochemical investigation of the methanol extract of Cyphostemma adenocaule liana (bark and wood) led to the isolation of two new ceanothane-type triterpenoids, cyphostemmic acid A 1 and cyphostemmic acid B 2, together with the known triterpenoids 3-7, β-sitosterol and its glucoside. The structures of the isolated compounds were established by 1D- and 2D-NMR spectroscopy. Ozonolysis of cyphostemmic acid A 1, epigouanic acid A 3 and betulin 6 yielded semisynthetic derivatives, cyphostemmic acid C 8, cyphostemmic acid D 9, and 3β,28-dihydroxy-30-norlupan-20-one 10 respectively. Compounds 1-4, 6, 8-10 were tested in vitro, for their antiplasmodial activity against Plasmodium falciparum 3D7 strain and showed weak activity.

  2. Potent antitrypanosomal triterpenoid saponins from Mussaenda luteola

    Science.gov (United States)

    Five new triterpenoid saponins, heinsiagenin A 3-O-[a-L-rhamnopyranosyl-(1->2)-Beta-D-glucopyranosyl-(1->2)]-B-D-glucopyranoside (1), heinsiagenin A 3-O-[a-L-rhamnopyranosyl-(1->2)-B-D-glucopyranosyl- (1->2)]-[B-D-glucopyranosyl-(1-4)]-B-D-glucopyranoside (2). 2a-hydroxyheinsiagenin A 3-o-[a-L-rhamn...

  3. Triterpenoids from Psidium guajava with Biocidal Activity

    Science.gov (United States)

    Ghosh, P.; Mandal, A.; Chakraborty, P.; Rasul, M. G.; Chakraborty, Madhumita; Saha, A.

    2010-01-01

    In continuation of our studies on the phytochemical investigation of medicinal plants available in the foothills of Darjeeling and Teri, we report herein the isolation of two triterpenoids betulinic acid and lupeol from the leaf extract of Psidium guajava and their potential antimicrobial and phytotoxic activities. All the structures of the isolated compounds were confirmed by spectral (IR, NMR) analysis and by comparison with the literature reports. PMID:21218065

  4. Cycloartane triterpenoids of propolis from Teresina - PI; Triterpenoides tipo cicloartano de propolis de Teresina - PI

    Energy Technology Data Exchange (ETDEWEB)

    Silva, Maria do Socorro Sousa da; Cito, Antonia Maria das Gracas Lopes; Chaves, Mariana H.; Lopes, Jose Arimateia Dantas [Universidade Federal do Piaui, Teresina, PI (Brazil). Dept. de Quimica]. E-mail: gracito@ufpi.br

    2005-09-15

    The chemical study of the propolis produced in Teresina city, state of Piaui, resulted in the identification of six cycloartane triterpenoids: isomangiferolic acid, 24-methylenecycloartane-3{beta},26-diol, mangiferolic acid, mangiferonic acid, ambonic acid and ambolic acid. The substances were characterized by one and two-dimensional {sup 1}H and {sup 13}C NMR analysis. (author)

  5. Triterpenoid biosynthesis in Euphorbia lathyris latex

    International Nuclear Information System (INIS)

    Hawkins, D.R.

    1987-11-01

    The structures of triterpenols, not previously been known, from Euphorbia lathyris latex are reported. A method for quantifying very small amounts of these compounds was developed. Concerning the biochemistry of the latex, no exogenous cofactors were required for the biosynthesis and the addition of compounds such as NADPAH and ATP do not stimulate the biosynthesis. The addition of DTE or a similar anti-oxidant was found to help reduce the oxidation of the latex, thus increasing the length of time that the latex remains active. The requirement of a divalent cation and the preference for Mn in the pellet was observed. The effect of several inhibitors on the biosynthesis of the triterpenoids was examined. Mevinolin was found to inhibit the biosynthesis of the triterpenoids from acetate, but not mevalonate. A dixon plot of the inhibition of acetate incorporation showed an I 50 concentration of 3.2 μM. Fenpropimorph was found to have little or no effect on the biosynthesis. Tridemorph was found to inhibit the biosynthesis of all of the triterpenoids with an I 50 of 4 μM. It was also observed that the cyclopropyl containing triterpenols, cycloartenol and 24-methylenecycloartenol were inhibited much more strongly than those containing an 8-9 double bond, lanosterol and 24-methylenelanosterol. The evidence indicates, but does not definetely prove, that lanosterol and 24-methylenelanosterol are not made from cycloartenol and 24-methylenecycloartenol via a ring-opening enzyme such as cycloeucalenol-obtusifoliol isomerase. The possibilty that cycloartenol is made via lanosterol was investigated by synthesizing 4-R-4- 3 H-mevalonic acid and incubating latex with a mixture of this and 14 C-mevalonic acid. From the 3 H/ 14 C ratio it was shown that cycloartenol and 24-methylenecycloartenol are not made via an intermediate containing as 8-9 double bond. 88 refs., 15 figs., 30 tabs

  6. Triterpenoid biosynthesis in Euphorbia lathyris latex

    Energy Technology Data Exchange (ETDEWEB)

    Hawkins, D.R.

    1987-11-01

    The structures of triterpenols, not previously been known, from Euphorbia lathyris latex are reported. A method for quantifying very small amounts of these compounds was developed. Concerning the biochemistry of the latex, no exogenous cofactors were required for the biosynthesis and the addition of compounds such as NADPAH and ATP do not stimulate the biosynthesis. The addition of DTE or a similar anti-oxidant was found to help reduce the oxidation of the latex, thus increasing the length of time that the latex remains active. The requirement of a divalent cation and the preference for Mn in the pellet was observed. The effect of several inhibitors on the biosynthesis of the triterpenoids was examined. Mevinolin was found to inhibit the biosynthesis of the triterpenoids from acetate, but not mevalonate. A dixon plot of the inhibition of acetate incorporation showed an I/sub 50/ concentration of 3.2 ..mu..M. Fenpropimorph was found to have little or no effect on the biosynthesis. Tridemorph was found to inhibit the biosynthesis of all of the triterpenoids with an I/sub 50/ of 4 ..mu..M. It was also observed that the cyclopropyl containing triterpenols, cycloartenol and 24-methylenecycloartenol were inhibited much more strongly than those containing an 8-9 double bond, lanosterol and 24-methylenelanosterol. The evidence indicates, but does not definetely prove, that lanosterol and 24-methylenelanosterol are not made from cycloartenol and 24-methylenecycloartenol via a ring-opening enzyme such as cycloeucalenol-obtusifoliol isomerase. The possibilty that cycloartenol is made via lanosterol was investigated by synthesizing 4-R-4-/sup 3/H-mevalonic acid and incubating latex with a mixture of this and /sup 14/C-mevalonic acid. From the /sup 3/H//sup 14/C ratio it was shown that cycloartenol and 24-methylenecycloartenol are not made via an intermediate containing as 8-9 double bond. 88 refs., 15 figs., 30 tabs.

  7. Triterpenoid saponins from Tocoyena brasiliensis Mart. (Rubiaceae)

    International Nuclear Information System (INIS)

    Hamerski, Lidilhone; Carbomezi, Carlos Alberto; Cavalheiro, Alberto Jose; Bolzani, Vanderlan da Silva; Young, Maria Claudia Marx

    2005-01-01

    The present communication reports the isolation and identification of four triterpenoid saponins from the chloroform extract of the leaves of Tocoyena brasiliensis: 3-O-β-D quinovopyranosyl quinovic acid, 3-O-β-D-quinovopyranosyl cincholic acid, 3-O-β-D-glucopyranosyl quinovic acid and the 28-O-β-D-glucopyranosyl ester derivative of quinovic acid as binary mixtures, respectively. From the ethanol extract a flavonoid identified as ramnazin-3-O-rutinoside was obtained. The structures of these compounds were assigned by data analysis of 1D and 2D NMR spectrometry and comparison with data recorded in the literature for these compounds. (author)

  8. Triterpenoids from Whole Plants of Phyllanthus urinaria

    Institute of Scientific and Technical Information of China (English)

    Ye Wu; Shuang-shuang Xie; Zheng-xi Hu; Zhao-di Wu; Yi Guo; Jin-wen Zhang; Jian-ping Wang; Yong-bo Xue; Yong-hui Zhang

    2017-01-01

    Objective To study the chemical constituents of whole plant of Phyllanthus urinaria and their biological activity.Methods The chemical constituents were isolated and purified by repeated column chromatography over silica gel,Rp-C18 (reverse phase),MCI,and Sephadex LH-20,as well as semi-preparative HPLC.NMR spectroscopic analyses were used for the structure identification.In this case,the inhibitory rate of NO production of the isolated triterpenoids was evaluated.Results Seven triterpenoids,identified as 28-norlup-20(29)-ene-3,17β-diol (1),betulin (2),β-betulinic acid (3),3-oxo-friedelan-28-oic acid (4),oleanolic acid (5),3R-E-coumaroyltaraxerol (6),and 3R-Z-coumaroyltaraxerol (7),were isolated and identified from the whole plants of P.urinaria.Compounds 1-5 exerted inhibitory effects against NO production in LPS-induced RAW 264.7 mouse macrophages with the inhibitory rate of NO production ranging from 4.0% to 27.8% at the concentration of 25μmol/L.Conclusion To the best of our knowledge,this is the first report of compounds 1-4,6,and 7 from the family Euphorbiaceae.Compounds 1-5 exhibited inhibitory effects against NO production in LPS-induced RAW 264.7 mouse macrophages.

  9. Triterpenoids from Whole Plants of Phyllanthus urinaria

    Institute of Scientific and Technical Information of China (English)

    Ye; Wu; Shuang-shuang; Xie; Zheng-xi; Hu; Zhao-di; Wu; Yi; Guo; Jin-wen; Zhang; Jian-ping; Wang; Yong-bo; Xue; Yong-hui; Zhang

    2017-01-01

    Objective To study the chemical constituents of whole plant of Phyllanthus urinaria and their biological activity.Methods The chemical constituents were isolated and purified by repeated column chromatography over silica gel,Rp-C18(reverse phase),MCI,and Sephadex LH-20,as well as semi-preparative HPLC.NMR spectroscopic analyses were used for the structure identification.In this case,the inhibitory rate of NO production of the isolated triterpenoids was evaluated.Results Seven triterpenoids,identified as28-norlup-20(29)-ene-3,17β-diol(1),betulin(2),β-betulinic acid(3),3-oxofriedelan-28-oic acid(4),oleanolic acid(5),3R-E-coumaroyltaraxerol(6),and 3R-Zcoumaroyltaraxerol(7),were isolated and identified from the whole plants of P.urinaria.Compounds 1-5 exerted inhibitory effects against NO production in LPS-induced RAW264.7 mouse macrophages with the inhibitory rate of NO production ranging from 4.0%to 27.8%at the concentration of 25 μmol/L.Conclusion To the best of our knowledge,this is the first report of compounds 1-4,6,and 7 from the family Euphorbiaceae.Compounds 1-5 exhibited inhibitory effects against NO production in LPS-induced RAW264.7 mouse macrophages.

  10. Bardoxolone methyl induces apoptosis and autophagy and inhibits epithelial-to-mesenchymal transition and stemness in esophageal squamous cancer cells

    Directory of Open Access Journals (Sweden)

    Wang YY

    2015-02-01

    Full Text Available Yan-Yang Wang,1,2 Yin-Xue Yang,3 Ren Zhao,1 Shu-Ting Pan,2,4 Hong Zhe,1 Zhi-Xu He,5 Wei Duan,6 Xueji Zhang,7 Tianxin Yang,8 Jia-Xuan Qiu,4 Shu-Feng Zhou2,51Department of Radiation Oncology, General Hospital of Ningxia Medical University, Yinchuan, People’s Republic of China; 2Department of Pharmaceutical Sciences, College of Pharmacy, University of South Florida, Tampa, FL, USA; 3Department of Colorectal Surgery, General Hospital of Ningxia Medical University, Yinchuan, People’s Republic of China; 4Department of Oral and Maxillofacial Surgery, The First Affiliated Hospital of Nanchang University, Nanchang, 5Guizhou Provincial Key Laboratory for Regenerative Medicine, Stem Cell and Tissue Engineering Research Center and Sino-US Joint Laboratory for Medical Sciences, Guiyang Medical University, Guiyang, People’s Republic of China; 6School of Medicine, Deakin University, Waurn Ponds, VIC, Australia; 7Research Center for Bioengineering and Sensing Technology, University of Science and Technology Beijing, Beijing, People’s Republic of China; 8Department of Internal Medicine, University of Utah and Salt Lake Veterans Affairs Medical Center, Salt Lake City, UT, USAAbstract: Natural and synthetic triterpenoids have been shown to kill cancer cells via multiple mechanisms. The therapeutic effect and underlying mechanism of the synthetic triterpenoid bardoxolone methyl (C-28 methyl ester of 2-cyano-3,12-dioxoolean-1,9-dien-28-oic acid; CDDO-Me on esophageal cancer are unclear. Herein, we aimed to investigate the anticancer effects and underlying mechanisms of CDDO-Me in human esophageal squamous cell carcinoma (ESCC cells. Our study showed that CDDO-Me suppressed the proliferation and arrested cells in G2/M phase, and induced apoptosis in human ESCC Ec109 and KYSE70 cells. The G2/M arrest was accompanied with upregulated p21Waf1/Cip1 and p53 expression. CDDO-Me significantly decreased B-cell lymphoma-extra large (Bcl-xl, B-cell lymphoma 2 (Bcl-2

  11. Screening for triterpenoid saponins in plants using hyphenated analytical platforms

    DEFF Research Database (Denmark)

    Khakimov, Bekzod; Tseng, Li Hong; Godejohann, Markus

    2016-01-01

    of saponin profiles from intact plant extracts as well as saponin aglycone profiles from hydrolysed samples. Continuously measured 1D proton NMR data during LC separation along with mass spectrometry data revealed significant differences, including contents of saponins, types of aglycones and numbers......Recently the number of studies investigating triterpenoid saponins has drastically increased due to their diverse and potentially attractive biological activities. Currently the literature contains chemical structures of few hundreds of triterpenoid saponins of plant and animal origin. Triterpenoid...... saponins consist of a triterpene aglycone with one or more sugar moieties attached to it. However, due to similar physico-chemical properties, isolation and identification of a large diversity of triterpenoid saponins remain challenging. This study demonstrates a methodology to screen saponins using...

  12. Triterpenoid saponins from Albizia lebbeck (L.) Benth and their inhibitory effect on the survival of high grade human brain tumor cells.

    Science.gov (United States)

    Noté, Olivier Placide; Jihu, Dong; Antheaume, Cyril; Zeniou, Maria; Pegnyemb, Dieudonné Emmanuel; Guillaume, Dominique; Chneiwess, Hervé; Kilhoffer, Marie Claude; Lobstein, Annelise

    2015-03-02

    As part of our search of new bioactive triterpenoid saponins from Cameroonian Mimosaceae plants, phytochemical investigation of the roots of Albizia lebbeck led to the isolation of two new oleanane-type saponins, named lebbeckosides A-B (1-2). Their structures were established on the basis of extensive 1D and 2D NMR ((1)H, (13)C NMR, DEPT, COSY, TOCSY, ROESY, HSQC, and HMBC) and HRESIMS studies, and by chemical evidence. Compounds 1-2 were evaluated for their inhibitory effect on the metabolism of high grade human brain tumor cells, the human glioblastoma U-87 MG cell lines and the glioblastoma stem-like TG1 cells isolated from a patient tumor, and known to be particularly resistant to standard therapies. The isolated saponins showed significant cytotoxic activity against U-87 MG and TG1 cancer cells with IC50 values of 3.46 μM and 1.36 μM for 1, and 2.10 μM and 2.24 μM for 2, respectively. Copyright © 2014 Elsevier Ltd. All rights reserved.

  13. Topical application of the synthetic triterpenoid RTA 408 activates Nrf2 and induces cytoprotective genes in rat skin.

    Science.gov (United States)

    Reisman, Scott A; Lee, Chun-Yue I; Meyer, Colin J; Proksch, Joel W; Ward, Keith W

    2014-07-01

    RTA 408 is a member of the synthetic oleanane triterpenoid class of compounds known to potently activate the cytoprotective transcription factor Nrf2. Because skin is constantly exposed to external oxidative stress, such as that from ultraviolet radiation, from chemical exposure, during improper wound healing, and throughout the course of cancer radiation therapy, it may benefit from activation of Nrf2. This study was conducted to evaluate the transdermal penetration properties and Nrf2 activation potential of RTA 408 in normal rat skin. RTA 408 (0.1, 1.0, or 3.0%) was applied topically to the shaved skin of male Sprague-Dawley rats twice daily for 4 days and once on Day 5. Topical application of RTA 408 resulted in transdermal penetration, with low but dose-dependent plasma exposure with AUC(0-24 h) values of 3.6, 26.0, and 41.1 h ng/mL for the 0.1, 1.0, and 3.0% doses, respectively. Further, topical application of RTA 408 resulted in increased translocation of Nrf2 to the nucleus, dose-dependent mRNA induction of Nrf2 target genes (e.g. Nqo1, Srxn1, Gclc, and Gclm), and induction of the protein expression of the prototypical Nrf2 target gene Nqo1 and increased total glutathione (GSH) in normal rat skin. Immunohistochemistry demonstrated that increased staining for Nqo1 and total GSH of structures in both the epidermis and dermis was consistent with the full transdermal penetration of RTA 408. Finally, topically administered RTA 408 was well tolerated with no adverse in-life observations and normal skin histology. Thus, the data support the further development of RTA 408 for the potential treatment of skin diseases.

  14. Three new triterpenoid saponins from Dianthus superbus.

    Science.gov (United States)

    Luo, Jian-Guang; Chen, Xia; Kong, Ling-Yi

    2011-01-01

    Three new triterpenoid saponins (1-3) were isolated from the dried aerial parts of Dianthus superbus L. (Caryophyllaceae). Their structures were established as 3-O-β-D-glucopyranosyl gypsogenic acid 28-O-[β-D-6-O-((3S)-3-hydroxyl-3-methylglutaryl)glucopyranosyl(1→6)]-β-D-glucopyranoside (1), 3-O-β-D-glucopyranosyl gypsogenic acid 28-O-[β-D-glucopyranosyl(1→3)][β-D-6-O-((3S)-hydroxyl-3-methylglutaryl)glucopyranosyl(1→6)]-β-D-glucopyranoside (2), 3-O-α-L-arabinopyranosyl-3β,16α-dihydroxyolean-12-en-23,28-dioic acid 28-O-[β-D-glucopyranosyl-(1→6)]-β-D-glucopyranoside (3), on the basis of various spectroscopic analyses and chemical degradations.

  15. Pentacyclic triterpenoids from the leaves of Terminalia brasiliensis

    International Nuclear Information System (INIS)

    Araujo, Delton Servulo; Chaves, Mariana H.

    2005-01-01

    Eleven oleanane, ursane and lupane-type triterpenes were isolated from the leaves of Terminalia brasiliensis Camb, daturadiol (3β,6β-dihydroxy-olean-12-ene), 3β-hydroxy-30-norlupan-20-one, lupenone, β-amyrenone, α-amyrenone, lupeol, β-amyrin, α-amyrin, betulin, erythrodiol and uvaol, in addition to squalene, sitosterol and α-tocopherol. The structures of these compounds were identified by 1 H and 13 C NMR spectral analysis and comparison with literature data. (author)

  16. Triterpenoids of Ganoderma theaecolum and their hepatoprotective activities.

    Science.gov (United States)

    Liu, Li-Ying; Chen, Hui; Liu, Chao; Wang, Hong-Qing; Kang, Jie; Li, Yan; Chen, Ruo-Yun

    2014-10-01

    Five new lanostane triterpenoids, ganoderic acid XL1 (1), ganoderic acid XL2 (2), 20-hydroxy-ganoderic acid AM1 (3), ganoderenic acid AM1 (4) and ganoderesin C (5), together with five known triterpenoids (6-10) were isolated from the fruiting bodies of Ganoderma theaecolum. Chemical structures were elucidated on the basis of spectroscopic evidence, including 1D, 2D NMR, mass spectrometric data and circular dichroism spectra. Compounds 1, 4, 5, 8, 9 and 10 (10 μM) exhibited hepatoprotective activities against DL-galactosamine-induced cell damage in HL-7702 cells. Copyright © 2014 Elsevier B.V. All rights reserved.

  17. A TRITERPENOID SAPONIN FROM SEEDS OF KOLOWE (Chydenanthus excelsus

    Directory of Open Access Journals (Sweden)

    Laode Rijai

    2010-06-01

    Full Text Available A triterpenoid saponin have been isolated from n-butanol fraction of the seeds of kolowe (Chydenanthus excelsus. The structure was determined as 3-O-[β-D-glucopyranosyl(1→3-β-D-xylopyranosyl(1→3- β - D-glucuronopyranosyloxy]- 22α -O-(2-methylbutiroyloxyolean-12-en-15α,16α,28-tri-hydroxy. Structure elucidation was accomplished by NMR (HMBC, HMQC/HSQC, ROE, ROESY, TOCSY methods, ESIMS, and IR spectroscopic.   Keywords: Chydenanthus excelsus, Lecythidaceae, Triterpenoid saponin

  18. Soulieoside R : A New Cycloartane Triterpenoid Glycoside from Souliea vaginata

    Directory of Open Access Journals (Sweden)

    Qiongyu Zou

    2018-01-01

    Full Text Available A new cycloartane triterpenoid glycoside, named soulieoside R, was isolated from the rhizomes of Souliea vaginata. Its structure was characterized by comprehensive analyses of 1H, 13C NMR, COSY, HSQC, HMBC, NOESY spectroscopic, and HRESIMS mass spectrometric data, as well as chemical methods. The new compound showed weak inhibitory activity against three human cancer cell lines.

  19. Two new triterpenoid saponins from rhizome of Anemone raddeana Regel

    DEFF Research Database (Denmark)

    Fan, Li; Lu, Jincai; Wang, Jing

    2009-01-01

    Two new 27-hydroxyoleanolic acid-type triterpenoid saponins, raddeanoside Ra (1) and raddeanoside Rb (2), were isolated from the rhizome of Anemone raddeana Regel. The structures of the two compounds were elucidated to be 27-hydroxyoleanolic acid 3-O-beta-D: -glucopyranosyl-(1 --> 4)-alpha...

  20. Triterpenoid saponins from Phytolacca rivinoides and Phytolacca bogotensis

    DEFF Research Database (Denmark)

    Nielsen, S. E.; Anthoni, U.; Christophersen, C.

    1995-01-01

    Investigation of the ethanolic extracts from Phytolacca rivinoides and P. bogotensis has resulted in the isolation of five new triterpenoid glycosides of serjanic acid. Their structures have been established mainly by spectroscopic methods (FAB-MS, H-1, (13)CNMR, COSY, NOESY, TOCSY, HETCOR and J-...

  1. Tubulin polymerization-stimulating activity of Ganoderma triterpenoids.

    Science.gov (United States)

    Kohno, Toshitaka; Hai-Bang, Tran; Zhu, Qinchang; Amen, Yhiya; Sakamoto, Seiichi; Tanaka, Hiroyuki; Morimoto, Satoshi; Shimizu, Kuniyoshi

    2017-04-01

    Tubulin polymerization is an important target for anticancer therapies. Even though the potential of Ganoderma triterpenoids against various cancer targets had been well documented, studies on their tubulin polymerization-stimulating activity are scarce. This study was conducted to evaluate the effect of Ganoderma triterpenoids on tubulin polymerization. A total of twenty-four compounds were investigated using an in vitro tubulin polymerization assay. Results showed that most of the studied triterpenoids exhibited microtuble-stabilizing activity to different degrees. Among the investigated compounds, ganoderic acid T-Q, ganoderiol F, ganoderic acid S, ganodermanontriol and ganoderic acid TR were found to have the highest activities. A structure-activity relationship (SAR) analysis was performed. Extensive investigation of the SAR suggests the favorable structural features for the tubulin polymerization-stimulating activity of lanostane triterpenes. These findings would be helpful for further studies on the potential mechanisms of the anticancer activity of Ganoderma triterpenoids and give some indications on the design of tubulin-targeting anticancer agents.

  2. Two new triterpenoid saponins from Dianthus superbus L.

    Science.gov (United States)

    Chen, Xia; Luo, Jian-Guang; Kong, Ling-Yi

    2010-06-01

    Two new triterpenoid saponins (1 and 2) were isolated from the dried aerial parts of Dianthus superbus L. (Caryophyllaceae). Their structures were elucidated on the basis of spectral data to be 3-O-beta-D-glucopyranosyl olean-9(11),12-diene-23,28-dioic acid 28-O-beta-D-glucopyranoside (1) and 3-O-beta-D-glucopyranosyl olean-11,13(18)-diene-23,28-dioic acid 28-O-beta-D-glucopyranoside (2).

  3. Dammarane triterpenoids from the roots of Gentiana rigescens.

    Science.gov (United States)

    Xu, Min; Wang, Dong; Zhang, Ying-Jun; Yang, Chong-Ren

    2007-05-01

    Six new minor dammarane triterpenoids were isolated from the roots of Gentiana rigescens. These include one aglycone, gentirigenic acid (1), and five glycosides, gentirigeosides A-E (2-6). Their structures were elucidated through detailed spectroscopic analyses, including 1D and 2D NMR techniques, and enzymatic hydrolysis. Antifungal testing of these compounds showed that the glycosides gentirigeosides A (2), C (4), and E (6) had antifungal activity against the plant pathogen Glomerella cingulata.

  4. Soulieoside O, a new cyclolanostane triterpenoid glycoside from Souliea vaginata.

    Science.gov (United States)

    Wu, Hai-Feng; Li, Peng-Fei; Zhu, Yin-Di; Zhang, Xiao-Po; Ma, Guo-Xu; Xu, Xu-Dong; Liu, Yi-Lin; Luo, Zheng-Hong; Chen, Di-Zhao; Zou, Qiong-Yu; Zhao, Zi-Jian

    2017-12-01

    A new cyclolanostane triterpenoid glycoside, soulieoside O (1), together with 25-O-acetylcimigenol-3-O-β-d-xylopyranoside (2) and cimigenol-3-O-β-d-xylopyranoside (3), was isolated from the rhizomes of Souliea vaginata. Their structures were characterized by spectroscopic analysis and chemical methods. The new compound showed moderate inhibitory activity against three human cancer cell lines with IC 50 values of 9.3-22.5 μM.

  5. Triterpenoids from Gymnema sylvestre and Their Pharmacological Activities

    Directory of Open Access Journals (Sweden)

    Giovanni Di Fabio

    2014-07-01

    Full Text Available Because plants are estimated to produce over 200,000 metabolites, research into new natural substances that can be used in the pharmaceutical, agrochemical and agro-industrial production of drugs, biopesticides and food additives has grown in recent years. The global market for plant-derived drugs over the last decade has been estimated to be approximately 30.69 billion USD. A relevant specific example of a plant that is very interesting for its numerous pharmacological properties, which include antidiabetic, anticarcinogenic, and neuroprotective effects is Gymnema sylvestre, used as a medicinal plant in Asia for thousands of years. Its properties are attributed to triterpenoidic saponins. In light of the considerable interest generated in the chemistry and pharmacological properties of G. sylvestre triterpenes and their analogues, we have undertaken this review in an effort to summarise the available literature on these promising bioactive natural products. The review will detail studies on the isolation, chemistry and bioactivity of the triterpenoids, which are presented in the tables. In particular the triterpenoids oxidised at C-23; their isolation, distribution in different parts of the plant, and their NMR spectral data; their names and physico-chemical characterisation; and the biological properties associated with these compounds, with a focus on their potential chemotherapeutic applications.

  6. Lanostane triterpenoids from Ganoderma hainanense J. D. Zhao.

    Science.gov (United States)

    Peng, XingRong; Liu, JieQing; Xia, JianJun; Wang, CuiFang; Li, XuYang; Deng, YuanYuan; Bao, NiMan; Zhang, ZhiRun; Qiu, MingHua

    2015-06-01

    Chemical investigation of the fruiting bodies of Ganoderma hainanense resulted in isolation of fourteen lanostane triterpenoids, including nine ganoderma acids and five ganoderma alcohols, together with five known compounds. Structural elucidation was determined using extensive spectroscopic technologies, Mosher's method and X-ray single crystal diffraction. Three of the compounds showed inhibitory activities against HL-60, SMMC-7721, A-549 and MCF-7 cells with IC50 values of 15.0-40.0 μM. Copyright © 2014 Elsevier Ltd. All rights reserved.

  7. Two new cucurbitane triterpenoids from the seeds of Momordica charantia.

    Science.gov (United States)

    Ma, Lin; Yu, Ai-Hua; Sun, Li-Li; Gao, Wan; Zhang, Meng-Meng; Su, Ya-Lun; Liu, Hua; Ji, Teng-Fei; Li, Di-Zao

    2014-01-01

    Two new cucurbitane triterpenoids 1 and 2 were isolated, together with six known compounds, from the seeds of Momordica charantia L. The structures of new compounds were determined to be 3-O-{[β-d-galactopyranosyl(1 → 6)]-O-β-d-galactopyranosyl}-23(R), 24(R), 25-trihydroxycucur-bit-5-ene (1), 3-O-[β-d-galactopyranosyl]-25-O-β-d-galactopyranosyl-7(R), 22(S), 23(R), 24(R), 25-pentahydroxycucurbit-5-ene (2), respectively. Their structures were elucidated by the combination of mass spectrometry, one- and two-dimensional NMR experiments and chemical reactions.

  8. Triterpenoid saponins from the roots of Clematis argentilucida.

    Science.gov (United States)

    Zhao, Mei; Ma, Ning; Qiu, Feng; Tian, Xiangrong; Zhang, Yan; Tang, Haifeng; Liu, Xinyou

    2014-09-01

    Reinvestigation of the n-BuOH extract of the roots of Clematis argentilucida led to the isolation of a new ursane-type triterpenoid saponin 1 and a new taraxerane-type saponin 2, four known saponins 3-6 first isolated from the species, together with seven saponins 7-13 reported in the previous papers. The structures of saponins 1-6 were elucidated by extensive spectroscopic analysis and chemical evidences. The ursane-type and taraxerane-type triterpenoid saponins were obtained from genus Clematis for the first time, and the aglycone of saponin 1, 3β,28-dihydroxy-18αH-ursan-20-en was first encountered. The cytotoxicity of all the saponins was evaluated against human glioblastoma U251MG cell lines. The monodesmosidic saponins 1, 2 and 4-8 exhibited cytotoxic activity against the cells with IC50 values ranging from 6.95 to 38.51 μM. Copyright © 2014 Elsevier B.V. All rights reserved.

  9. Optimization of extraction parameters of pentacyclic triterpenoids from Swertia chirata stem using response surface methodology.

    Science.gov (United States)

    Pandey, Devendra Kumar; Kaur, Prabhjot

    2018-03-01

    In the present investigation, pentacyclic triterpenoids were extracted from different parts of Swertia chirata by solid-liquid reflux extraction methods. The total pentacyclic triterpenoids (UA, OA, and BA) in extracted samples were determined by HPTLC method. Preliminary studies showed that stem part contains the maximum pentacyclic triterpenoid and was chosen for further studies. Response surface methodology (RSM) has been employed successfully by solid-liquid reflux extraction methods for the optimization of different extraction variables viz., temperature ( X 1 35-70 °C), extraction time ( X 2 30-60 min), solvent composition ( X 3 20-80%), solvent-to-solid ratio ( X 4 30-60 mlg -1 ), and particle size ( X 5 3-6 mm) on maximum recovery of triterpenoid from stem parts of Swertia chirata . A Plackett-Burman design has been used initially to screen out the three extraction factors viz., particle size, temperature, and solvent composition on yield of triterpenoid. Moreover, central composite design (CCD) was implemented to optimize the significant extraction parameters for maximum triterpenoid yield. Three extraction parameters viz., mean particle size (3 mm), temperature (65 °C), and methanol-ethyl acetate solvent composition (45%) can be considered as significant for the better yield of triterpenoid A second-order polynomial model satisfactorily fitted the experimental data with the R 2 values of 0.98 for the triterpenoid yield ( p  < 0.001), implying good agreement between the experimental triterpenoid yield (3.71%) to the predicted value (3.79%).

  10. Novel cycloartane-type triterpenoid from the fruits of Nandina domestica.

    Science.gov (United States)

    Kodai, Tetsuya; Horiuchi, Yoshinori; Nishioka, Yasuhiro; Noda, Naoki

    2010-04-01

    A novel cycloartane-type triterpenoid was isolated from the fruits of Nandina domestica (Berberidaceae). The structure was characterized as 24-methylene-3-oxocycloartane 13-carboxylic acid on the basis of NMR spectroscopic data.

  11. Simultaneous quantification of flavonoids and triterpenoids in licorice using HPLC.

    Science.gov (United States)

    Wang, Yuan-Chuen; Yang, Yi-Shan

    2007-05-01

    Numerous bioactive compounds are present in licorice (Glycyrrhizae Radix), including flavonoids and triterpenoids. In this study, a reversed-phase high-performance liquid chromatography (HPLC) method for simultaneous quantification of three flavonoids (liquiritin, liquiritigenin and isoliquiritigenin) and four triterpenoids (glycyrrhizin, 18alpha-glycyrrhetinic acid, 18beta-glycyrrhetinic acid and 18beta-glycyrrhetinic acid methyl ester) from licorice was developed, and further, to quantify these 7 compounds from 20 different licorice samples. Specifically, the reverse-phase HPLC was performed with a gradient mobile phase composed of 25 mM phosphate buffer (pH 2.5)-acetonitrile featuring gradient elution steps as follows: 0 min, 100:0; 10 min, 80:20; 50 min, 70:30; 73 min, 50:50; 110 min, 50:50; 125 min, 20:80; 140 min, 20:80, and peaks were detected at 254 nm. By using our technique, a rather good specificity was obtained regarding to the separation of these seven compounds. The regression coefficient for the linear equations for the seven compounds lay between 0.9978 and 0.9992. The limits of detection and quantification lay in the range of 0.044-0.084 and 0.13-0.25 microg/ml, respectively. The relative recovery rates for the seven compounds lay between 96.63+/-2.43 and 103.55+/-2.77%. Coefficient variation for intra-day and inter-day precisions lay in the range of 0.20-1.84 and 0.28-1.86%, respectively. Based upon our validation results, this analytical technique is a convenient method to simultaneous quantify numerous bioactive compounds derived from licorice, featuring good quantification parameters, accuracy and precision.

  12. Delivery Systems for Birch-Bark Triterpenoids and Their Derivatives in Anticancer Research.

    Science.gov (United States)

    Mierina, Inese; Vilskersts, Reinis; Turks, Maris

    2018-05-29

    Birch-bark triterpenoids and their semi-synthetic derivatives possess a wide range of biological activities including cytotoxic effects on various tumour cell lines. However, due to the low solubility and bioavailability, their medicinal applications are rather limited. The use of various nanotechnology-based drug delivery systems is rapidly developing approach to the solubilisation of insufficiently bioavailable pharmaceuticals. Herein, the drug delivery systems deemed to be applicable for birch-bark triterpenoid structures are reviewed. The aforementioned disadvantages of birch-bark triterpenoids and their semi-synthetic derivatives can be overcome through their incorporation into organic nanoparticles, which include various dendrimeric systems, as well as embedding the active compounds into polymer matrices or complexation with carbohydrate nanoparticles without covalent bonding. Some of the known triterpenoid delivery systems consist of nanoparticles featuring inorganic cores covered with carbohydrates or other polymers. Methods for delivering the title compounds through encapsulation and emulsification into lipophilic media are also suitable. Besides, the birch-bark triterpenoids can form self-assembling systems with increased bio-availability. Even more, the self-assembling systems are used as carriers for delivering other chemotherapeutic agents. Another advantage besides increased bioavailability and anticancer activity is the reduced overall systemic toxicity in most of the cases, when triterpenoids are delivered with any of the carriers. Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.org.

  13. Determination of total triterpenoid acids in different part and extract of Ganoderma lucidum

    Directory of Open Access Journals (Sweden)

    FENG Huiqin

    2013-04-01

    Full Text Available Aim To develop a method for determination of total triterpenoid acids in different part and extracts of Ganoderma lucidum. Method The samples of Ganoderma lucidum were extracted with ethanol and successively extracted with CHCl3 and 5% NaHCO3,the NaHCO3 layer was acidified to pH 3 with 2 mol/L HCl,the resulting precipitates were dissolved in CHCl3 and evaporated in vacuo then weighed. The total triterpenoid acids were obtained. Result The total triterpenoid acids of Ganoderma lucidum fruitbody,spore and mycelium were (8.58±0.25 mg/g,(3.48±0.03 mg/g and (1.75 ±0.09 mg/g respectively. The total triterpenoid acids of pileus and stipe were (12.62±0.22 mg/g and (7.66±0.08 mg/g. The range of total triterpenoid acid content among 10 batches of Ganoderma lucidum fruitbody purchased from the market was between 4.34 to 16.39 mg/g. The highest content fro/8/8/88/ m Ganoderma lucidum fruiting body with alcohol - water extracting was (208.70±5.54 mg/g and the lowest content with alkaline solution extracting was (123.07±4.99 mg/g. The composition of total triterpenoid acid from fruitbody,spores and extract of fruitbody analyzed by HPLC were almost the same. This method is reliable for determination of total triterpenoid acid in the fruiting body and its extracts,spore and mycelium from Ganoderma lucidum,which provides an indicator for the quality of Ganoderma lucidum product.

  14. New 30-Noroleanane Triterpenoid Saponins from Holboellia coriacea Diels

    Directory of Open Access Journals (Sweden)

    Wenbing Ding

    2016-06-01

    Full Text Available Three new 30-noroleanane triterpenoid saponins, akebonoic acid 28-O-β-d-glucopyranosyl-(1′′→6′-β-d-glucopyranosyl ester (1, akebonoic acid 28-O-(6′′-O-caffeoyl-β-d-glucopyranosyl-(1′′→6′-β-d-glucopyranosyl ester (Holboelliside A, 2 and 3β,20α,24-trihydroxy-29-norolean-12-en-28-oic acid 3-O-(6′-O-caffeoyl-β-d-glucopyranoside (Holboelliside B, 3 were isolated from the stems of Holboellia coriacea Diels, together with five known compounds, eupteleasaponin VIII (4, 3α-akebonoic acid (5, quinatic acid (6, 3β-hydroxy-30-norhederagenin (7 and quinatoside A (8. The structures of these compounds were determined on the basis of spectral and chemical evidence. Compounds 1–5 were evaluated for their inhibitory activity against three human tumors HepG2, HCT116 and SGC-7901 cell lines in vitro.

  15. Improvement of polysaccharide and triterpenoid production of Ganoderma lucidum through mutagenesis of protoplasts

    Directory of Open Access Journals (Sweden)

    Ren Peng

    2016-03-01

    Full Text Available Ganoderma lucidum is a traditional medicinal macrofungus in China, which has two kinds of key bioactive compounds -- polysaccharides and triterpenoids. To improve the polysaccharide and triterpenoid production from G. lucidum, the preparation and regeneration conditions of protoplasts were optimized. This was done by systematic trials with various parameters, and protoplast mutation was subsequently performed. A mycelium that was cultivated for seven days and treated with 0.33 mL of 1% snailase and 0.66 mL of 0.5% cellulase solution for 2.5 h at 30 °C in the presence of osmotic pressure stabilizer mannitol (0.5 mol/L, had the best conditions, in which the resultant protoplasts were 6.40 × 105/mL and the regeneration rate was 6.25%. The resultant protoplasts were subjected to subsequent mutation by lithium chloride or by the combination of lithium chloride and Triton X-100. The highest yields of intracellular polysaccharide and triterpenoid in two mutant strains were 37.50 and 40.81 mg/g, which were increased with 568.45% and 373.43%, respectively, as compared to the original strain. Furthermore, the yields of intracellular polysaccharides and triterpenoids in the second generation and the third generation of the mutants were comparable to that of the first generation, which showed genetic stability of the mutants for the production of polysaccharides and triterpenoids.

  16. An Approach for Expanding Triterpenoid Complexity via Divergent Norrish-Yang Photocyclization

    Science.gov (United States)

    Ignatenko, Vasily A.; Tochtrop, Gregory P.

    2013-01-01

    Triterpenoids comprise a very diverse family of polycyclic molecules that is well-known to possess a myriad of medicinal properties. Therefore, triterpenoids constitute an attractive target for medicinal chemistry and diversity-oriented synthesis. Photochemical transformations provide a promising tool for the rapid, green and inexpensive generation of skeletal diversity in the construction of natural product-like libraries. With this in mind, we have developed a diversity-oriented strategy, whereby the parent triterpenoids bryonolic acid and lanosterol are converted to the pseudo-symmetrical polyketones by sequential allylic oxidation and oxidative cleavage of the bridging double bond at the B/C-ring fusion. The resultant polyketones were hypothesized to undergo divergent Norrish-Yang cyclization to produce unique 6/4/8-fused triterpenoid analogs. The subtle differences between parent triterpenoids led to dramatically different spatial arrangements of reactive functionalities. This finding was rationalized through conformational analysis to explain unanticipated photoinduced pinacolization, as well as the regio- and stereochemical outcome of the desired Norrish-Yang cyclization. PMID:23544445

  17. Triterpenoids from Ganoderma lucidum inhibit the activation of EBV antigens as telomerase inhibitors.

    Science.gov (United States)

    Zheng, Dong-Shu; Chen, Liang-Shu

    2017-10-01

    Nasopharyngeal carcinoma (NPC) is a malignant disease that threatens the health of humans. To find effective agents for the inhibition of Epstein-Barr virus (EBV) infection, which is associated with NPC, a phytochemical investigation of Ganoderma lucidum was carried out in the present study. Five triterpenoids were identified, including ganoderic acid A (compound 1), ganoderic acid B (compound 2), ganoderol B (compound 3), ganodermanontriol (compound 4), and ganodermanondiol (compound 5), on the basis of spectroscopic analysis. An inhibition of EBV antigens activation assay was implemented to elucidate the triterpenoids from G. lucidum and potentially prevent NPC. All the triterpenoids showed significant inhibitory effects on both EBV EA and CA activation at 16 nmol. At 3.2 nmol, all the compounds moderately inhibited the activation of the two antigens. The activity of telomerase was inhibited by these triterpenoids at 10 µM. Molecular docking demonstrated that compound 1 was able to inhibit telomerase as a ligand. In addition, the physicochemical properties of these compounds were calculated to elucidate their drug-like properties. These results provided evidence for the application of these triterpenoids and whole G. lucidum in the treatment of NPC.

  18. Inhibition of neuraminidase by Ganoderma triterpenoids and implications for neuraminidase inhibitor design

    Science.gov (United States)

    Zhu, Qinchang; Bang, Tran Hai; Ohnuki, Koichiro; Sawai, Takashi; Sawai, Ken; Shimizu, Kuniyoshi

    2015-01-01

    Neuraminidase (NA) inhibitors are the dominant antiviral drugs for treating influenza in the clinic. Increasing prevalence of drug resistance makes the discovery of new NA inhibitors a high priority. Thirty-one triterpenoids from the medicinal mushroom Ganoderma lingzhi were analyzed in an in vitro NA inhibition assay, leading to the discovery of ganoderic acid T-Q and TR as two inhibitors of H5N1 and H1N1 NAs. Structure-activity relationship studies revealed that the corresponding triterpenoid structure is a potential scaffold for the design of NA inhibitors. Using these triterpenoids as probes we found, through further in silico docking and interaction analysis, that interactions with the amino-acid residues Arg292 and/or Glu119 of NA are critical for the inhibition of H5N1 and H1N1. These findings should prove valuable for the design and development of NA inhibitors. PMID:26307417

  19. Cycloartenol triterpenoid saponins from Cimicifuga simplex (Ranunculaceae) and their biological effects.

    Science.gov (United States)

    Wu, Lun; Chen, Zhi-Li; Su, Yang; Wang, Qiu-Hong; Kuang, Hai-Xue

    2015-02-01

    The constituents of Cimicifuga plants have been extensively investigated, and the principal metabolites are 9,19-cyclolanostane triterpenoid glycosides, which are distributed widely in Cimicifuga plants, but not in other members of the Ranunculaceae family, and are considered to be characteristics of the Cimicifuga genus. This type of triterpenoid glycoside possesses several important biological activities. More than 120 cycloartane triterpene glycosides have been isolated from Cimicifuga simplex Wormsk. The aim of this review article is to summarize all the major findings based on the available scientific literatures on C. simplex, with a focus on the identified 9,19-cyclolanostane triterpenoid glycosides. Biological studies of cycloartane triterpene glycosides from Cimicifuga spp. are also discussed. Copyright © 2015 China Pharmaceutical University. Published by Elsevier B.V. All rights reserved.

  20. New lanostane-type triterpenoids from the fruiting body of Ganoderma hainanense.

    Science.gov (United States)

    Li, Wei; Lou, Lan-Lan; Zhu, Jian-Yong; Zhang, Jun-Sheng; Liang, An-An; Bao, Jing-Mei; Tang, Gui-Hua; Yin, Sheng

    2016-12-01

    Five new lanostane-type triterpenoids, ganoderenses A-E (1-5), two new lanostane nor-triterpenoids, ganoderenses F and G (6 and 7), along with 13 known analogues (8-20) were isolated from the fruiting body of Ganoderma hainanense. Their structures were determined by combined chemical and spectral methods, and the absolute configurations of compounds 1 and 13 were confirmed by single crystal X-ray diffraction. All compounds were evaluated for inhibitory activity against thioredoxin reductase (TrxR), a potential target for cancer chemotherapy with redox balance and antioxidant functions, but were inactive. Copyright © 2016 Elsevier B.V. All rights reserved.

  1. One new 19-nor cucurbitane-type triterpenoid from the stems of Momordica charantia.

    Science.gov (United States)

    Li, Yong-chao; Xu, Xin-juan; Yang, Jing; Wu, Xing-gang; Fu, Qing-yun

    2016-01-01

    One new 19-nor cucurbitane-type triterpenoid (3β,9β,25-trihydroxy-7β-methoxy-19-nor-cucurbita-5,23(E)-diene) (1), together with other six known cucurbitane-type triterpenoids (2-7), were isolated from the stems of Momordica charantia L. The chemical structure of 1 was elucidated by extensive 1D NMR and 2D NMR (HSQC, HMBC, COSY and ROESY), MS experiments. Using MTT assay, compound 1 exhibited weak cytotoxicity against HL-60, A-549, and SK-BR-3 cell lines with the IC50 values at 27.3, 32.7 and 26.6 μM, respectively.

  2. Remarkably high surface visco-elasticity of adsorption layers of triterpenoid saponins

    NARCIS (Netherlands)

    Golemanov, K.; Tcholakova, S.; Denkov, N.; Pelan, E.; Stoyanov, S.D.

    2013-01-01

    Saponins are natural surfactants, with molecules composed of a hydrophobic steroid or triterpenoid group, and one or several hydrophilic oligosaccharide chains attached to this group. Saponins are used in cosmetic, food and pharmaceutical products, due to their excellent ability to stabilize

  3. Triterpenoids from Brazilian Ilex species and their in vitro antitrypanosomal activity.

    Science.gov (United States)

    Taketa, Alexandre T C; Gnoatto, Simone C B; Gosmann, Grace; Pires, Viviane S; Schenkel, Eloir P; Guillaume, Dominique

    2004-10-01

    From the leaves of Ilex affinis and Ilex buxifolia, two adulterant species of "erva mate" (Ilex paraguariensis), three new triterpenoid glycosides were isolated. Affinoside 1 (3beta-O-[beta-D-glucopyranosyl-(1-->3)-[2-O-acetyl-(1-->2

  4. 1H and 13C NMR spectral assignments of four dammarane triterpenoids from carnauba wax.

    Science.gov (United States)

    Cysne, Juliana de Brito; Braz-Filho, Raimundo; Assunção, Marcus Vinícius; Uchoa, Daniel E de Andrade; Silveira, Edilberto R; Pessoa, Otília Deusdênia L

    2006-06-01

    The phytochemical investigation of carnauba wax led to the isolation of three new dammarane triterpenoids 1, 2 and 4, together with the known triterpene 3. The structures of the new compounds were determined by 1D and 2D NMR spectroscopy and by comparison with published data for closely related compounds. 2006 John Wiley & Sons, Ltd.

  5. Cuticular membrane of Fuyu persimmon fruit is strengthened by triterpenoid nano-fillers.

    Directory of Open Access Journals (Sweden)

    Shuntaro Tsubaki

    Full Text Available The mechanical defensive performance of fruit cuticular membranes (CMs is largely dependent on the molecular arrangement of their constituents. Here, we elucidated nano-sized interactions between cutin and triterpenoids in the cuticular matrix of Fuyu persimmon fruits (Diospyroskaki Thunb. cv. Fuyu, focusing on the mechanical properties using a combination of polymer analyses. The fruit CMs of Fuyu were primarily composed of wax (34.7%, which was predominantly triterpenoids followed by higher aliphatic compounds, and cutin (48.4%, primarily consisting of 9,10-epoxy-18-hydroxyoctadecanoic acid and 9,10,18-trihydroxyoctadecanoic acid. Based on the tensile tests of the CM, the removal of wax lead to a considerable decrease in the maximum stress and elastic modulus accompanied by an increase in the maximum strain, indicating that wax is of significant importance for maintaining the mechanical strength of the CM. Wide-angle X-ray diffraction and relaxation time measurements using solid-state (13C nuclear magnetic resonance indicated that the triterpenoids in the cuticular matrix construct a nanocomposite at a mixing scale below 20-24 nm; however, the higher aliphatic compounds did not exhibit clear interactions with cutin. The results indicated that the triterpenoids in the cuticular matrix endow toughness to the CM by functioning as a nanofiller.

  6. Cytotoxic triterpenoids isolated from sweet chestnut heartwood (Castanea sativa) and their health benefits implication.

    Science.gov (United States)

    Pérez, Andy J; Pecio, Łukasz; Kowalczyk, Mariusz; Kontek, Renata; Gajek, Gabriela; Stopinsek, Lidija; Mirt, Ivan; Stochmal, Anna; Oleszek, Wiesław

    2017-11-01

    For centuries wood containers have been used in aging of wines and spirits, due to the pleasant flavors they give to the beverages. Together with oak, sweet chestnut wood (Castanea sativa) have been often used for such purpose. The maturation process involves the transfer of secondary metabolites, mainly phenolics, from the wood to the liquid. At the same time, other metabolites, such as triterpenoids and their glycosides, can also be released. Searching for the extractable triterpenoids from sweet chestnut heartwood (C. sativa), two new ursane-type triterpenoid saponins named chestnoside A (1) and chestnoside B (2), together with two known oleanen-type analogs (3 and 4) were isolated and characterized. The cytotoxicity of isolated compounds was tested against two cancer cell lines (PC3 and MCF-7), and normal lymphocytes. Breast cancer cells (MCF-7) were more affected by tested compounds than prostate cancer cells (PC3). Chestnoside B (2) exhibited the strongest cytotoxicity with an IC 50 of 12.3 μM against MCF-7 cells, lower than those of positive controls, while it was moderately active against normal lymphocytes (IC 50  = 67.2 μM). These results highlight the occurrence of triterpenoid saponins in sweet chestnut heartwood and their potential for the chemoprevention of breast cancer. Copyright © 2017 Elsevier Ltd. All rights reserved.

  7. Cloning and Characterization of Farnesyl Diphosphate Synthase Gene Involved in Triterpenoids Biosynthesis from Poria cocos

    Directory of Open Access Journals (Sweden)

    Jianrong Wang

    2014-12-01

    Full Text Available Poria cocos (P. cocos has long been used as traditional Chinese medicine and triterpenoids are the most important pharmacologically active constituents of this fungus. Farnesyl pyrophosphate synthase (FPS is a key enzyme of triterpenoids biosynthesis. The gene encoding FPS was cloned from P. cocos by degenerate PCR, inverse PCR and cassette PCR. The open reading frame of the gene is 1086 bp in length, corresponding to a predicted polypeptide of 361 amino acid residues with a molecular weight of 41.2 kDa. Comparison of the P. cocos FPS deduced amino acid sequence with other species showed the highest identity with Ganoderma lucidum (74%. The predicted P. cocos FPS shares at least four conserved regions involved in the enzymatic activity with the FPSs of varied species. The recombinant protein was expressed in Pichia pastoris and purified. Gas chromatography analysis showed that the recombinant FPS could catalyze the formation of farnesyl diphosphate (FPP from geranyl diphosphate (GPP and isopentenyl diphosphate (IPP. Furthermore, the expression profile of the FPS gene and content of total triterpenoids under different stages of development and methyl jasmonate treatments were determined. The results indicated that there is a positive correlation between the activity of FPS and the amount of total triterpenoids produced in P. cocos.

  8. Leucocontextins A-R, lanostane-type triterpenoids from Ganoderma leucocontextum.

    Science.gov (United States)

    Zhao, Zhen-Zhu; Chen, He-Ping; Li, Zheng-Hui; Dong, Ze-Jun; Bai, Xue; Zhou, Zhong-Yu; Feng, Tao; Liu, Ji-Kai

    2016-03-01

    Eighteen new lanostane-type triterpenoids, namely leucocontextins A-R (1-18) were isolated from the fruiting bodies of Ganoderma leucocontextum. Their structures were established by 1D and 2D NMR data in conjunction with HRESIMS/HREIMS, X-ray single crystal diffraction analysis. Compound 18 exhibited weak cytotoxicity against K562 and MCF-7 cell lines with IC50 of 20-30 μM. Copyright © 2015 Elsevier B.V. All rights reserved.

  9. [Minor components in food plants--II. Triterpenoid saponins from Ullucus tuberosus].

    Science.gov (United States)

    Dini, A; Rastrelli, L; Saturnino, P; Schettino, O

    1991-12-01

    The present work deals with the isolation and characterization of triterpenoid saponins from Ullucus tuberosus. This class of natural products can account at least in part for unpalatability of the tubers of the plant. Two saponins were isolated 28-O-beta-D-glucopyranosyl-epihederagenine and 28-O-beta-D-glucopyranoside-3-O-beta-D-glucopyranosyl (1"-- 2')-beta-D-glucopyranosyl-oleanoate.

  10. In vitro effectiveness of triterpenoids and their synergistic effect with antibiotics against Staphylococcus aureus strains.

    Science.gov (United States)

    Hamza, Muhammad; Nadir, Maha; Mehmood, Nadir; Farooq, Adeel

    2016-01-01

    The aim of this study is to evaluate the effect of four triterpenoids such as oleanolic acid, ursolic acid, cycloastragenol, and beta-boswellic acid alone and in combination with antibiotics against Staphylococcus aureus strains. Sixteen clinical strains of S. aureus from infected wounds were isolated. Eight were methicillin-sensitive S. aureus (MSSA), and the other eight were methicillin-resistant S. aureus (MRSA). The activity was also seen in reference S. aureus American Type Culture Collection ™ strains. The activity of all the triterpenoids and antibiotics against S. aureus was evaluated by broth microdilution method. The effectiveness was judged by comparing the minimum inhibitory concentrations (MICs) of the compounds with antibiotics. The combination of antibiotics with compounds was evaluated by their fractional inhibitory concentrations (FIC). Against both clinical and reference MSSA strains, none of the compounds exhibited comparable activity to antibiotics vancomycin or cefradine except for ursolic acid (MIC 7.8 μg/ml). Against MRSA, all compounds (MIC 16-128 μg/ml) showed lesser activity than vancomycin (MIC 5.8 μg/ml). Among triterpenoid-antibiotic combinations, the most effective were ursolic acid and vancomycin against clinical strain MSSA (FIC S 0.17). However, overall, different combinations between triterpenoids and antibiotics showed 95%-46% ( P antibiotics compared to when antibiotics were used alone. Cefradine, a drug not suitable for treating MRSA (MIC = 45 μg/ml), showed a remarkable decrease in its MIC (87% Pantibiotics. However, when used in combination with antibiotics, they showed remarkable synergistic effect and thus can help in prolonging the viability of these antibiotics against S. aureus infections. Furthermore, reduction in MIC of cefradine with oleanolic acid indicates their potential use against MRSA.

  11. Cycloartane triterpenoid saponins from water soluble of Passiflora edulis Sims and their antidepressant-like effects.

    Science.gov (United States)

    Wang, Cong; Xu, Feng-Qing; Shang, Jian-Hua; Xiao, Huai; Fan, Wei-Wei; Dong, Fa-Wu; Hu, Jiang-Miao; Zhou, Jun

    2013-07-30

    Various species of genus Passiflora have been used as traditional folk medicines owing to their sedative and anti-hypertensive properties. Passiflora edulis Sims most widely grown in the warm temperate for their fragrant fruits and their twigs and leaves are used as a folk medicine for treating both anxiety and nervousness in American countries. The present study was to evaluate the antidepressant-like effect and the active components of this plant. The alcohol extracts of the stems (PES, 10 and 2 g/kg of the plant materials) and leaves (PEL, 10 and 2 g/kg of the plant materials) of Passiflora edulis Sims were orally administered to mice for 7 day. The animals were tested in the forced swim test (FST) and tail suspension test (TST). After behavioral assay of ethanol extract, phytochemical research of the stems and leaves (5.7 kg) of Passiflora edulis Sims were developed and further bioactive verification of monomeric compounds were conducted. There are mainly cycloartane triterpenoids and their saponins isolated from this plant, including two new cycloartane triterpenoid saponins named cyclopassifloside ХII (1) and ХIII (2), together with six known cycloartane triterpenoids, cyclopassifloic acids B and E, cyclopassiflosides II, VI, IX and XI. The ethanol extract of Passiflora edulis Sims together with isolated compounds cyclopassiflosides IX and XI may possess antidepressant-like effect. Cycloartane triterpenoid was one of the main compositions of Passiflora edulis Sims and possess antidepressant-like activity. Crown Copyright © 2013. Published by Elsevier Ireland Ltd. All rights reserved.

  12. Synergistic antimicrobial activity between pentacyclic triterpenoids and antibiotics against Staphylococcus aureus strains

    Directory of Open Access Journals (Sweden)

    Navaratnam Parasakthi

    2011-06-01

    Full Text Available Abstract Background There has been considerable effort to discover plant-derived antibacterials against methicillin-resistant strains of Staphylococcus aureus (MRSA which have developed resistance to most existing antibiotics, including the last line of defence, vancomycin. Pentacyclic triterpenoid, a biologically diverse plant-derived natural product, has been reported to show anti-staphylococcal activities. The objective of this study is to evaluate the interaction between three pentacyclic triterpenoid and standard antibiotics (methicillin and vancomycin against reference strains of Staphylococcus aureus. Methods and Results The activity of the standard antibiotics and compounds on reference methicillin-sensitive and resistant strains of S. aureus were determined using the macrodilution broth method. The minimum inhibitory concentration (MIC of the compounds was compared with that of the standard antibiotics. The interaction between any two antimicrobial agents was estimated by calculating the fractional inhibitory concentration (FIC index of the combination. The various combinations of antibiotics and compounds reduced the MIC to a range of 0.05 to 50%. Conclusion Pentacyclic triterpenoids have shown anti-staphylococcal activities and although individually weaker than common antibiotics produced from bacteria and fungi, synergistically these compounds may use different mechanism of action or pathways to exert their antimicrobial effects, as implicated in the lowered MICs. Therefore, the use of current antibiotics could be maintained in their combination with plant-derived antibacterial agents as a therapeutic option in the treatment of S. aureus infections.

  13. The Antitumor Effects of Triterpenoid Saponins from the Anemone flaccida and the Underlying Mechanism

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    Lin-Tao Han

    2013-01-01

    Full Text Available Anemone flaccida Fr. Schmidt, a family of ancient hopanoids, have been used as traditional Asian herbs for the treatments of inflammation and convulsant diseases. Previous study on HeLa cells suggested that triterpenoid saponins from Anemone flaccida Fr. Schmidt may have potential antitumor effect due to their apoptotic activities. Here, we confirmed the apoptotic activities of the following five triterpenoid saponins: glycoside St-I4a (1, glycoside St-J (2, anhuienoside E (3, hedera saponin B (4, and flaccidoside II (5 on human BEL-7402 and HepG2 hepatoma cell lines, as well as the model of HeLa cells treated with lipopolysaccharide (LPS. We found that COX-2/PGE2 signaling pathway, which plays key roles in the development of cancer, is involved in the antitumor activities of these saponins. These data provide the evidence that triterpenoid saponins can induce apoptosis via COX-2/PGE2 pathway, implying a preventive role of saponins from Anemone flaccida in tumor.

  14. Extraction of triterpenoids and phenolic compounds from Ganoderma lucidum: optimization study using the response surface methodology.

    Science.gov (United States)

    Oludemi, Taofiq; Barros, Lillian; Prieto, M A; Heleno, Sandrina A; Barreiro, Maria F; Ferreira, Isabel C F R

    2018-01-24

    The extraction of triterpenoids and phenolic compounds from Ganoderma lucidum was optimized by using the response surface methodology (RSM), using heat and ultrasound assisted extraction techniques (HAE and UAE). The obtained results were compared with that of the standard Soxhlet procedure. RSM was applied using a circumscribed central composite design with three variables (time, ethanol content, and temperature or ultrasonic power) and five levels. The conditions that maximize the responses (extraction yield, triterpenoids and total phenolics) were: 78.9 min, 90.0 °C and 62.5% ethanol and 40 min, 100.0 W and 89.5% ethanol for HAE and UAE, respectively. The latter was the most effective, resulting in an extraction yield of 4.9 ± 0.6% comprising a content of 435.6 ± 21.1 mg g -1 of triterpenes and 106.6 ± 16.2 mg g -1 of total phenolics. The optimized extracts were fully characterized in terms of individual phenolic compounds and triterpenoids by HPLC-DAD-ESI/MS. The recovery of the above-mentioned bioactive compounds was markedly enhanced using the UAE technique.

  15. Lanostane triterpenoids from Ganoderma curtisii and their NO production inhibitory activities of LPS-induced microglia.

    Science.gov (United States)

    Jiao, Yang; Xie, Ting; Zou, Lu-Hui; Wei, Qian; Qiu, Li; Chen, Li-Xia

    2016-08-01

    Twenty-nine lanostane triterpenoids (1-29) were obtained from the EtOH extract of fruiting bodies of the Ganoderma curtisii. Among them, compound 1 was a new lanostane triterpenoid and compounds 2-5 were isolated from the genus Ganoderma for the first time and their structures were unambiguously identified in this work. The NMR data of the four known lanostane triterpenoids (2-5) were reported for the first time because their structures were all tentatively characterized by interpreting the MS data from the methanol extract of Ganoderma lucidum or from the metabolites in rat bile after oral administration of crude extract of the fruiting bodies of G. lucidum using fragmentation rules. Their anti-inflammatory activities were tested by measuring their inhibitory effects on nitric oxide (NO) production in BV-2 microglia cells activated by lipopolysaccharide. Their IC50 values were in a range from 3.65±0.41 to 28.04±2.81μM. Copyright © 2016 Elsevier Ltd. All rights reserved.

  16. Quantitative analysis of anti-inflammatory and radical scavenging triterpenoid esters in evening primrose seeds.

    Science.gov (United States)

    Zaugg, Janine; Potterat, Olivier; Plescher, Andreas; Honermeier, Bernd; Hamburger, Matthias

    2006-09-06

    Lipophilic triterpenoidal esters with radical scavenging and cyclooxygenase inhibitory properties were recently found in cold-pressed, nonraffinated evening primrose oil (EPO). A quantitative assay for the analysis of 3-O-trans-caffeoyl derivatives of betulinic, morolic, and oleanolic acid in evening primrose seeds was developed and validated. Extraction efficiency >99% was achieved by means of pressurized liquid extraction with two extraction cycles and 80% (v/v) ethanol at 120 degrees C. Analysis of esters was by normal-phase high-performance liquid chromatography on a Diol column and hexane/ethyl acetate (containing 0.1% formic acid) (65:35) as the eluent. The analytes were determined without further prepurification. Seeds from defined cultures of Oenothera biennis, Oenothera lamarckiana, and Oenothera ammophila, grown under identical conditions, were analyzed. The cultures originated from seeds from eight collections in the wild and from selections from five cultivars. The content of total triterpenoidal esters in seeds varied between 1.34 and 2.78 mg/g. Three types of qualitative patterns were observed for the triterpenoidal esters. The influence of different harvest times and plant treatments was studied with the cultivar Anothera. Variations between 1.5 and 2.3 mg/g were found.

  17. Accumulation of Charantin and Expression of Triterpenoid Biosynthesis Genes in Bitter Melon (Momordica charantia).

    Science.gov (United States)

    Cuong, Do Manh; Jeon, Jin; Morgan, Abubaker M A; Kim, Changsoo; Kim, Jae Kwang; Lee, Sook Young; Park, Sang Un

    2017-08-23

    Charantin, a natural cucurbitane type triterpenoid, has been reported to have beneficial pharmacological functions such as anticancer, antidiabetic, and antibacterial activities. However, accumulation of charantin in bitter melon has been little studied. Here, we performed a transcriptome analysis to identify genes involved in the triterpenoid biosynthesis pathway in bitter melon seedlings. A total of 88,703 transcripts with an average length of 898 bp were identified in bitter melon seedlings. On the basis of a functional annotation, we identified 15 candidate genes encoding enzymes related to triterpenoid biosynthesis and analyzed their expression in different organs of mature plants. Most genes were highly expressed in flowers and/or fruit from the ripening stages. An HPLC analysis confirmed that the accumulation of charantin was highest in fruits from the ripening stage, followed by male flowers. The accumulation patterns of charantin coincide with the expression pattern of McSE and McCAS1, indicating that these genes play important roles in charantin biosynthesis in bitter melon. We also investigated optimum light conditions for enhancing charantin biosynthesis in bitter melon and found that red light was the most effective wavelength.

  18. Structure-Activity Relationships of Pentacyclic Triterpenoids as Potent and Selective Inhibitors against Human Carboxylesterase 1

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    Li-Wei Zou

    2017-06-01

    Full Text Available Human carboxylesterase 1 (hCE1, one of the most important serine hydrolases distributed in liver and adipocytes, plays key roles in endobiotic homeostasis and xenobiotic metabolism. This study aimed to find potent and selective inhibitors against hCE1 from phytochemicals and their derivatives. To this end, a series of natural triterpenoids were collected and their inhibitory effects against human carboxylesterases (hCEs were assayed using D-Luciferin methyl ester (DME and 6,8-dichloro-9,9-dimethyl-7-oxo-7,9-dihydroacridin-2-yl benzoate (DDAB as specific optical substrate for hCE1, and hCE2, respectively. Following screening of a series of natural triterpenoids, oleanolic acid (OA, and ursolic acid (UA were found with strong inhibitory effects on hCE1 and relative high selectivity over hCE2. In order to get the highly selective and potent inhibitors of hCE1, a series of OA and UA derivatives were synthesized from OA and UA by chemical modifications including oxidation, reduction, esterification, and amidation. The inhibitory effects of these derivatives on hCEs were assayed and the structure-activity relationships of tested triterpenoids as hCE1 inhibitors were carefully investigated. The results demonstrated that the carbonyl group at the C-28 site is essential for hCE1 inhibition, the modifications of OA or UA at this site including esters, amides and alcohols are unbeneficial for hCE1 inhibition. In contrast, the structural modifications on OA and UA at other sites, such as converting the C-3 hydroxy group to 3-O-β-carboxypropionyl (compounds 20 and 22, led to a dramatically increase of the inhibitory effects against hCE1 and very high selectivity over hCE2. 3D-QSAR analysis of all tested triterpenoids including OA and UA derivatives provide new insights into the fine relationships linking between the inhibitory effects on hCE1 and the steric-electrostatic properties of triterpenoids. Furthermore, both inhibition kinetic analyses and docking

  19. Triterpenoid saponins from Polaskia chichipe Backbg. and their inhibitory or promotional effects on the melanogenesis of B16 melanoma cells.

    Science.gov (United States)

    Fujihara, Koji; Takahashi, Kunio; Koyama, Kiyotaka; Kinoshita, Kaoru

    2017-10-01

    Five new oleanane-type saponins 1-5 together with a known saponin 6 and a steroidal glycoside 7 were isolated from Polaskia chichipe Backbg., and their structures were determined from their 1D and 2D NMR and HRFABMS spectral data. The six isolated saponins 1-6 were tested for their effects on the melanogenesis of B16 melanoma 4A5 cells. Compound 1 exerted an inhibitory effect at 100 μM whereas compound 3 promoted melanogenesis at the same concentration, even though these two compounds contain the same aglycon structure. The dose-dependent activities of compounds 1 and 3 on melanin synthesis were investigated.

  20. Estimation of triterpenoids from Heliotropium marifolium Koen. ex Retz. in vivo and in vitro. I. Antimicrobial screening.

    Science.gov (United States)

    Singh, B; Dubey, M M

    2001-05-01

    The hexane extract of Heliotropium marifolium yielded a mixture of triterpenoids: beta-sitosterol, stigmasterol, beta-amyrin, friedelan-3beta-ol (epifriedelenol), cycloartenone, beta-amyrin acetate, friedelin and epifriedenyl acetate. Isolated triterpenoid and reference antibiotics (gentamycin/mycostatin) were tested against selected pathogenic bacteria and fungi, e.g. Escherichia coli, Staphylococcus aureus, Aspergillus niger and Penicillium chrysogenum. The inhibition zone (IZ) and the activity index (AI) of isolated compounds were recorded and it was found that epifriedenyl acetate (IZ = 17; AI = 1.06) was the most active. The present study deals with the quantification and assessment of their growth inhibitory potency. It has been reported that cycloartenone was the major triterpenoid in both in vivo (0.54%) and in vitro (0.11%) cell cultures. Copyright 2001 John Wiley & Sons, Ltd.

  1. Dereplication of pentacyclic triterpenoids in plants by GC-EI/MS.

    Science.gov (United States)

    Gu, Jian-Qiao; Wang, Yuehong; Franzblau, Scott G; Montenegro, Gloria; Timmermann, Barbara N

    2006-01-01

    Three common plant-derived pentacyclic triterpenoids, oleanolic acid (1), betulinic acid (2) and ursolic acid (3), have been found to exhibit moderate anti-tubercular activity in a microplate alamar blue assay. In order to facilitate the discovery of novel anti-tubercular leads with diverse chemical structures, a new and rapid GC-EI/MS method was developed simultaneously and unambiguously to dereplicate 1-3 as their methyl esters with limits of detection of 25.6, 26.9 and 26.8 ng, respectively.

  2. 3-O-trans-caffeoylisomyricadiol: a new triterpenoid from Tamarix nilotica growing in Saudi Arabia.

    Science.gov (United States)

    Orfali, Raha S; Ebada, Sherif S; El-Shafae, Azza M; Al-Taweel, Areej M; Lin, Wen H; Wray, Victor; Proksch, Peter

    2009-01-01

    A detailed chemical study of the aerial parts of Tamarix nilotica (Tamaricaceae) from Saudi Arabia led to the isolation of a new pentacyclic triterpenoid, 3-O-trans-caffeoylisomyricadiol, in addition to nine known compounds. The structures of all isolated compounds were unambiguously elucidated by 1D, 2D NMR, and mass spectrometry. In the radical scavenging (DPPH) assay, 3-O-trans-caffeoylisomyricadiol exhibited potent antioxidant activity with an IC50 value of 3.56 microM, while that for quercetin (standard antioxidant) was 5.72 microM.

  3. Triterpenoid saponins from Tocoyena brasiliensis Mart. (Rubiaceae); Saponinas triterpenicas de Tocoyena brasiliensis Mart. (Rubiaceae)

    Energy Technology Data Exchange (ETDEWEB)

    Hamerski, Lidilhone; Carbomezi, Carlos Alberto; Cavalheiro, Alberto Jose; Bolzani, Vanderlan da Silva [UNESP, Araraquara, SP (Brazil). Inst. de Quimica]. E-mail: bolzaniv@iq.unesp.br; Young, Maria Claudia Marx [Instituto de Botanica, Sao Paulo, SP (Brazil). Secao de Fisiologia e Bioquimica de Plantas

    2005-07-15

    The present communication reports the isolation and identification of four triterpenoid saponins from the chloroform extract of the leaves of Tocoyena brasiliensis: 3-O-{beta}-D quinovopyranosyl quinovic acid, 3-O-{beta}-D-quinovopyranosyl cincholic acid, 3-O-{beta}-D-glucopyranosyl quinovic acid and the 28-O-{beta}-D-glucopyranosyl ester derivative of quinovic acid as binary mixtures, respectively. From the ethanol extract a flavonoid identified as ramnazin-3-O-rutinoside was obtained. The structures of these compounds were assigned by data analysis of 1D and 2D NMR spectrometry and comparison with data recorded in the literature for these compounds. (author)

  4. Saponinas triterpênicas de Tocoyena brasiliensis Mart. (Rubiaceae Triterpenoid saponins from Tocoyena brasiliensis Mart. (Rubiaceae

    Directory of Open Access Journals (Sweden)

    Lidilhone Hamerski

    2005-08-01

    Full Text Available The present communication reports the isolation and identification of four triterpenoid saponins from the chloroform extract of the leaves of Tocoyena brasiliensis: 3-O-beta-D-quinovopyranosyl quinovic acid, 3-O-beta-D-quinovopyranosyl cincholic acid, 3-O-beta-D-glucopyranosyl quinovic acid and the 28-O-beta-D-glucopyranosyl ester derivative of quinovic acid as binary mixtures, respectively. From the ethanol extract a flavonoid identified as ramnazin-3-O-rutinoside was obtained. The structures of these compounds were assigned by data analysis of 1D and 2D NMR spectrometry and comparison with data recorded in the literature for these compounds.

  5. Lanostane-type triterpenoids from the fruiting body of Ganoderma calidophilum.

    Science.gov (United States)

    Huang, Sheng-Zhuo; Ma, Qing-Yun; Kong, Fan-Dong; Guo, Zhi-Kai; Cai, Cai-Hong; Hu, Li-Li; Zhou, Li-Man; Wang, Qi; Dai, Hao-Fu; Mei, Wen-Li; Zhao, You-Xing

    2017-11-01

    To search for active anti-cancer constituents in the fruiting body of Ganoderma calidophilum, we have successfully isolated four previously undescribed spiro-lactone lanostane triterpenoids (spiroganocalitones A-D), two previously undescribed lanostanoids (ganodecalones A and B) together with twenty-three known ones. The structures of the six previously undescribed compounds were elucidated based on 1D, 2D-NMR, and HRMS analyses. Ganoderone A showed moderate cytotoxic activity against K562, BEL7402, and SGC790 cell lines with IC 50 values of 7.62, 6.28, and 3.55 μM, respectively. Copyright © 2017 Elsevier Ltd. All rights reserved.

  6. Cucurbitane-type triterpenoids from the fruit pulp of Momordica charantia.

    Science.gov (United States)

    Liao, Yun-Wen; Chen, Chiy-Rong; Kuo, Yueh-Hsiung; Hsu, Jue-Liang; Shih, Wen-Ling; Cheng, Hsueh-Ling; Huang, Tzou-Chi; Chang, Chi-I

    2012-12-01

    Three new cucurbitane-type triterpenoids, 5beta,19-epoxy-23(R)-methoxycucurbita-6,24-dien-3beta-ol (1), 5beta,19-epoxy-23(S)-methoxycucurbita-6,24-dien-3beta-ol (2), and 3beta-hydroxy-23(R)-methoxycucurbita-6,24-dien-5beta,19-olide (3), were isolated from the fruit pulp of Momordica charantia. Their structures were established on the basis of extensive NMR (1H, 13C, COSY, HMQC, HMBC, and NOESY) and EI-MS studies. Compound 1 exhibited cytotoxic activity against the SK-Hep 1 cell line.

  7. [Analysis of triterpenoids in Ganoderma lucidum by microwave-assisted continuous extraction].

    Science.gov (United States)

    Lu, Yan-fang; An, Jing; Jiang, Ye

    2015-04-01

    For further improving the extraction efficiency of microwave extraction, a microwave-assisted contijuous extraction (MACE) device has been designed and utilized. By contrasting with the traditional methods, the characteristics and extraction efficiency of MACE has also been studied. The method was validated by the analysis of the triterpenoids in Ganoderma lucidum. The extraction conditions of MACE were: using 95% ethanol as solvent, microwave power 200 W and radiation time 14.5 min (5 cycles). The extraction results were subsequently compared with traditional heat reflux extraction ( HRE) , soxhlet extraction (SE), ultrasonic extraction ( UE) as well as the conventional microwave extraction (ME). For triterpenoids, the two methods based on the microwaves (ME and MACE) were in general capable of finishing the extraction in 10, 14.5 min, respectively, while other methods should consume 60 min and even more than 100 min. Additionally, ME can produce comparable extraction results as the classical HRE and higher extraction yield than both SE and UE, however, notably lower extraction yield than MASE. More importantly, the purity of the crud extract by MACE is far better than the other methods. MACE can effectively combine the advantages of microwave extraction and soxhlet extraction, thus enabling a more complete extraction of the analytes of TCMs in comparison with ME. And therefore makes the analytic result more accurate. It provides a novel, high efficient, rapid and reliable pretreatment technique for the analysis of TCMs, and it could potentially be extended to ingredient preparation or extracting techniques of TCMs.

  8. Supercritical Fluid Extraction of Eucalyptus globulus Bark—A Promising Approach for Triterpenoid Production

    Science.gov (United States)

    Domingues, Rui M. A.; Oliveira, Eduardo L. G.; Freire, Carmen S. R.; Couto, Ricardo M.; Simões, Pedro C.; Neto, Carlos P.; Silvestre, Armando J. D.; Silva, Carlos M.

    2012-01-01

    Eucalyptus bark contains significant amounts of triterpenoids with demonstrated bioactivity, namely triterpenic acids and their acetyl derivatives (ursolic, betulinic, oleanolic, betulonic, 3-acetylursolic, and 3-acetyloleanolic acids). In this work, the supercritical fluid extraction (SFE) of Eucalyptus globulus deciduous bark was carried out with pure and modified carbon dioxide to recover this fraction, and the results were compared with those obtained by Soxhlet extraction with dichloromethane. The effects of pressure (100–200 bar), co-solvent (ethanol) content (0, 5 and 8% wt), and multistep operation were studied in order to evaluate the applicability of SFE for their selective and efficient production. The individual extraction curves of the main families of compounds were measured, and the extracts analyzed by GC-MS. Results pointed out the influence of pressure and the important role played by the co-solvent. Ethanol can be used with advantage, since its effect is more important than increasing pressure by several tens of bar. At 160 bar and 40 °C, the introduction of 8% (wt) of ethanol greatly improves the yield of triterpenoids more than threefold. PMID:22837719

  9. Fragment-based discovery of novel pentacyclic triterpenoid derivatives as cholesteryl ester transfer protein inhibitors.

    Science.gov (United States)

    Chang, Yongzhi; Zhou, Shuxi; Li, Enqin; Zhao, Wenfeng; Ji, Yanpeng; Wen, Xiaoan; Sun, Hongbin; Yuan, Haoliang

    2017-01-27

    Cholesteryl Ester Transfer Protein (CETP) is an important therapeutic target for the treatment of atherosclerotic cardiovascular disease. Our molecular modeling study revealed that pentacyclic triterpenoid compounds could mimic the protein-ligand interactions of the endogenous ligand cholesteryl ester (CE) by occupying its binding site. Alignment of the docking conformations of oleanolic acid (OA), ursolic acid (UA) and the crystal conformations of known CETP inhibitor Torcetrapib in the active site proposed the applicability of fragment-based drug design (FBDD) approaches in this study. Accordingly, a series of pentacyclic triterpenoid derivatives have been designed and synthesized as novel CETP inhibitors. The most potent compound 12e (IC 50 :0.28 μM) validated our strategy for molecular design. Molecular dynamics simulations illustrated that the more stable hydrogen bond interaction of the UA derivative 12e with Ser191 and stronger hydrophobic interactions with Val198, Phe463 than those of OA derivative 12b mainly led to their significantly different CETP inhibitory activity. These novel potent CETP inhibitors based on ursane-type scaffold should deserve further investigation. Copyright © 2016 Elsevier Masson SAS. All rights reserved.

  10. Comparative Metabolite Profiling of Triterpenoid Saponins and Flavonoids in Flower Color Mutations of Primula veris L.

    Science.gov (United States)

    Apel, Lysanne; Kammerer, Dietmar R.; Stintzing, Florian C.; Spring, Otmar

    2017-01-01

    Primula veris L. is an important medicinal plant with documented use for the treatment of gout, headache and migraine reaching back to the Middle Ages. Triterpenoid saponins from roots and flowers are used in up-to-date phytotherapeutic treatment of bronchitis and colds due to their expectorant and secretolytic effects. In addition to the wild type plants with yellow petals, a red variant and an intermediate orange form of Primula veris L. have recently been found in a natural habitat. The secondary metabolite profiles of roots, leaves and flowers of these rare variants were investigated and compared with the wild type metabolome. Two flavonoids, six flavonoid glycosides, four novel methylated flavonoid glycosides, five anthocyanins and three triterpenoid saponins were identified in alcoholic extracts from the petals, leaves and roots of the three variants by high performance liquid chromatography (HPLC)-diode array detection (DAD)/mass spectrometry (MSn) analyses. Anthocyanins were detected in the petals of the red and orange variety, but not in the wild type. No other effects on the metabolite profiles of the three varieties have been observed. The possibility is discussed that a regulatory step of the anthocyanin biosynthetic pathway may have been affected by mutation thus triggering color polymorphism in the petals. PMID:28098796

  11. Predicting the functions and specificity of triterpenoid synthases: a mechanism-based multi-intermediate docking approach.

    Directory of Open Access Journals (Sweden)

    Bo-Xue Tian

    2014-10-01

    Full Text Available Terpenoid synthases construct the carbon skeletons of tens of thousands of natural products. To predict functions and specificity of triterpenoid synthases, a mechanism-based, multi-intermediate docking approach is proposed. In addition to enzyme function prediction, other potential applications of the current approach, such as enzyme mechanistic studies and enzyme redesign by mutagenesis, are discussed.

  12. New lupane triterpenoids from Solidago canadensis that inhibit the lyase activity of DNA polymerase beta.

    Science.gov (United States)

    Chaturvedula, V S Prakash; Zhou, Bing-Nan; Gao, Zhijie; Thomas, Shannon J; Hecht, Sidney M; Kingston, David G I

    2004-12-01

    Bioassay-directed fractionation of a methyl ethyl ketone extract of Solidago canadensis L. (Asteraceae), using an assay to detect the lyase activity of DNA polymerase beta, resulted in the isolation of the four new lupane triterpenoids 1-4 and the seven known compounds lupeol, lupeyl acetate, ursolic acid, cycloartenol, cycloartenyl palmitate, alpha-amyrin acetate, and stigmasterol. The structures of the new compounds were established as 3beta-(3R-acetoxyhexadecanoyloxy)-lup-20(29)-ene (1), 3beta-(3-ketohexadecanoyloxy)-lup-20(29)-ene (2), 3beta-(3R-acetoxyhexadecanoyloxy)-29-nor-lupan-20-one (3), and 3beta-(3-hetohexadecanoyloxy)-29-nor-lupan-20-one (4), respectively, on the basis of extensive 1D and 2D NMR spectroscopic interpretation and chemical modification studies. All 11 compounds were inhibitory to the lyase activity of DNA polymerase beta.

  13. Cytotoxic effect of triterpenoids from the root bark of Hibiscus syriacus.

    Science.gov (United States)

    Shi, Li-Shian; Wu, Chao-Hsuan; Yang, Te-Chun; Yao, Chen-Wen; Lin, Hang-Ching; Chang, Wen-Liang

    2014-09-01

    In this study, 4 new triterpenoids-3β- acetoxy-olean-11-en,28,13β-olide (1), 3β- acetoxy-11α,12α-epoxy-olean-28,13β-olide (2), 19α-epi-betulin (3), and 20, 28-epoxy-17β,19β-lupan-3β-ol (4)-and 12 known compounds, were isolated from the root bark of Hibiscus syriacus L. by using acetone extraction. Their structures were characterized by extensive spectroscopic analysis. To investigate cytotoxicity, A549 human lung cancer cells were exposed to the extract and the compounds identified from it. Significantly reduced cell viability was observed with betulin-3-caffeate (12) (IC50, 4.3 μM). The results of this study indicate that betulin-3-caffeate (12) identified from H. syriacus L. may warrant further investigation for potential as anticancer therapies. Copyright © 2014 Elsevier B.V. All rights reserved.

  14. Isolation, characterization, and in rats plasma pharmacokinetic study of a new triterpenoid saponin from Dianthus superbus.

    Science.gov (United States)

    Ren, Yina; Xu, Xiaobao; Zhang, Qianlan; Lu, Yongzhuang; Li, Ximin; Zhang, Lin; Tian, Jingkui

    2017-02-01

    One new oleanolic acid triterpenoid saponin, 3-O-β-D-glucopyranosyl olean-11, 13(18)-diene-23,28-dioic acid, (hereafter referred to as DS-1) was isolated from the traditional Chinese medicinal plant Dianthus superbus (D. superbus). DS-1 plays an important role in the bioactivity of D. superbus. Thus, a sensitive, reliable and accurate reversed-phased liquid chromatography with tandem mass spectrometry (LC-MS/MS) in negative ion mode was developed and validated for the quantification and pharmacokinetic study of DS-1 in rats plasma. The pharmacokinetic profile showed that DS-1 was rapidly absorbed and eliminated in plasma, indicating that significant accumulation of the compound in biological specimen is unlikely. In addition, poor absorption into systemic circulation was observed after oral administration of DS-1, resulting in low absolute bioavailability (0.92 %).

  15. Plant Resources, 13C-NMR Spectral Characteristic and Pharmacological Activities of Dammarane-Type Triterpenoids

    Directory of Open Access Journals (Sweden)

    Jingya Ruan

    2016-08-01

    Full Text Available Dammarane-type triterpenoids (DTT widely distribute in various medicinal plants. They have generated a great amount of interest in the field of new drug research and development. Generally, DTT are the main bioactive ingredients abundant in Araliaceae plants, such as Panax ginseng, P. japonicas, P. notoginseng, and P. quinquefolium. Aside from Araliaceae, DTT also distribute in other families, including Betulaceae, Cucurbitaceae, Meliaceae, Rhamnaceae, and Scrophulariaceae. Until now, about 136 species belonging to 46 families have been reported to contain DTT. In this article, the genus classifications of plant sources of the botanicals that contain DTT are reviewed, with particular focus on the NMR spectral features and pharmacological activities based on literature reports, which may be benefit for the development of new drugs or food additives.

  16. Cucurbitane-type triterpenoids from the stems and leaves of Momordica charantia.

    Science.gov (United States)

    Zhao, Gao-Ting; Liu, Jie-Qing; Deng, Yuan-Yuan; Li, Hai-Zhou; Chen, Jian-Chao; Zhang, Zhi-Run; Zhou, Lin; Qiu, Ming-Hua

    2014-06-01

    Six new cucurbitane-type triterpenoids, karavilagenin F (1), karavilosides XII and XIII (2, 3), momordicines VI, VII, and VIII (4, 5 and 6), along with four known ones, 5β,19-epoxy-25-methoxycucurbita-6,23-diene-3β,19-diol (7), 5β,19-epoxycucurbita-6, 23-diene-3β,19,25-triol (8), kuguacin R (9), and (19R,23E)-5β,19-epoxy-19-methoxycucurbita-6,23,25-trien-3β-ol (10), were isolated from the stems and leaves of Momordica charantia L. Their chemical structures were elucidated by extensive 1D NMR and 2D NMR (HSQC, HMBC, COSY, and ROESY), MS experiments, and CD spectrum. Compound 6 showed weak cytotoxicity against five human cancer cells lines with IC50 values of 14.3-20.5μmol/L. Copyright © 2014 Elsevier B.V. All rights reserved.

  17. New Cytotoxic Triterpenoid Saponins from the Roots of Albizia gummifera (J.F.Gmel.) C.A.Sm.

    Science.gov (United States)

    Simo, Line Made; Noté, Olivier Placide; Mbing, Joséphine Ngo; Aouazou, Sarah Ali; Guillaume, Dominique; Muller, Christian Dominique; Pegnyemb, Dieudonné Emmanuel; Lobstein, Annelise

    2017-10-01

    As part of our search for new bioactive saponins from Cameroonian medicinal plants, two new oleanane-type saponins, named gummiferaosides D and E (1 and 2), along with one known saponin, julibroside J 8 (3), were isolated from the roots of Albizia gummifera. Their structures were established on the basis of extensive 1D- and 2D-NMR ( 1 H- and 13 C-NMR, DEPT, COSY, TOCSY, NOESY, HSQC, HSQC-TOCSY, and HMBC) and HR-ESI-MS studies, and by chemical evidence. The apoptotic effect of saponins 1 - 3 was evaluated on the A431 human epidermoid cancer cell. Flow cytometric analyses showed that saponins 1 - 3 induced apoptosis of human epidermoid cancer cell (A431) in a dose-dependent manner. © 2017 Wiley-VHCA AG, Zurich, Switzerland.

  18. Novel Bacterial Proteins and Lipids Reveal the Diversity of Triterpenoid Biomarker Synthesis

    Science.gov (United States)

    Wei, J. H.; Banta, A. B.; Gill, C. C. C.; Giner, J. L.; Welander, P. V.

    2017-12-01

    Lipids preserved in sediments and rocks function as organic biomarkers providing evidence for the types of organisms that lived in ancient environments. We use a combined approach utilizing comparative genomics, molecular biology, and lipid analysis to discover novel cyclic triteprenoid lipids and their biosynthetic pathways in bacteria. Here, we present two cases of bacterial synthesis of pentacylic triterpenols previously thought to be indicative of eukaryotes, which address current incongruities in the fossil record. Cyclic triterpenoid lipids, such as hopanoids and sterols, are generally associated with bacteria and eukaryotes, respectively. The pentacyclic triterpenoid tetrahymanol, first discovered in the ciliate Tetrahymena pyriformis, and its diagenetic product gammacerane, have been previously interpreted as markers for eukaryotes and linked to water column stratification. Yet the occurrence of tetrahymanol in bacteria implies our knowledge of extant tetrahymanol producers is not complete. Through comparative genomics we identified a new gene required for tetrahymanol synthesis in the bacterium Methylomicrobium alcaliphilum. This gene encodes a novel enzyme, Tetrahymanol synthase (THS), that synthesizes tetrahymanol from the hopanoid diploptene demonstrating a pathway for tetrahymanol production in bacteria distinct from that in eukaryotes. We bionformatically identified THS homologs in 104 bacterial genomes and 472 metagenomes, implying a great diversity of tetrahymanol producers. Lipids of the arborane class, such as iso-arborinol, are commonly found in modern angiosperms. Arobranes are synthesized by the enzyme oxidosqualene cyclase (OSC), which in plants can form both tetra and pentacyclic molecules. While bacteria are known to produce tetracyclic sterol compounds, bacterial synthesis of pentacyclic arborane class triterpenols of this class were previously undiscovered. We have identified a bacterium, Eudoraea adriatica, whose OSC synthesizes

  19. Triterpenoids and Polysaccharide Fractions of Ganoderma tsugae Exert Different Effects on Antiallergic Activities

    Directory of Open Access Journals (Sweden)

    Miaw-Ling Chen

    2015-01-01

    Full Text Available This study was to investigate antiallergic effects of triterpenoids (Gt-TRE and polysaccharide (Gt-PS extracts from Ganoderma tsugae, using mast cell line RBL-2H3, T cell line EL4, primary T cells, and transfected RAW264.7 macrophage cells. The results showed that histamine secreted from activated RBL-2H3 mast cells was significantly suppressed by Gt-TRE but not Gt-PS. Interleukin- (IL- 4 secreted from activated EL4 cells was significantly suppressed by Gt-TRE but not Gt-PS. Further primary CD4+ T cells cultures also confirmed that Gt-TRE (5~50 µg/mL significantly suppressed Th2 cytokines IL-4 and IL-5 secretions but had no effect on Th1 cytokines IL-2 and interferon (IFN-γ. Gt-PS did not affect IL-4 and IL-5 secretions until higher doses (400, 500 µg/mL and significantly suppressed IFNγ secretions but enhanced IL-2 at these high doses. The reporter gene assay indicated that Gt-TRE inhibited but Gt-PS enhanced the transcriptional activity of NF-κB in activated transfected RAW264.7 cells and transfected EL4 cells. IL-4 secreted by this transfected EL-4 cells was also significantly decreased by Gt-TRE but not by Gt-PS, suggesting that these two fractions may exert different effects on NF-κB related cytokines expression. These data suggested that triterpenoids fraction of Ganoderma tsugae might be the main constituents to alleviate allergic asthma.

  20. UPLC/Q-TOF MS-based metabolomics and qRT-PCR in enzyme gene screening with key role in triterpenoid saponin biosynthesis of Polygala tenuifolia.

    Science.gov (United States)

    Zhang, Fusheng; Li, Xiaowei; Li, Zhenyu; Xu, Xiaoshuang; Peng, Bing; Qin, Xuemei; Du, Guanhua

    2014-01-01

    The dried root of Polygala tenuifolia, named Radix Polygalae, is a well-known traditional Chinese medicine. Triterpenoid saponins are some of the most important components of Radix Polygalae extracts and are widely studied because of their valuable pharmacological properties. However, the relationship between gene expression and triterpenoid saponin biosynthesis in P. tenuifolia is unclear. In this study, ultra-performance liquid chromatography (UPLC) coupled with quadrupole time-of-flight mass spectrometry (Q-TOF MS)-based metabolomic analysis was performed to identify and quantify the different chemical constituents of the roots, stems, leaves, and seeds of P. tenuifolia. A total of 22 marker compounds (VIP>1) were explored, and significant differences in all 7 triterpenoid saponins among the different tissues were found. We also observed an efficient reference gene GAPDH for different tissues in this plant and determined the expression level of some genes in the triterpenoid saponin biosynthetic pathway. Results showed that MVA pathway has more important functions in the triterpenoid saponin biosynthesis of P. tenuifolia. The expression levels of squalene synthase (SQS), squalene monooxygenase (SQE), and beta-amyrin synthase (β-AS) were highly correlated with the peak area intensity of triterpenoid saponins compared with data from UPLC/Q-TOF MS-based metabolomic analysis. This finding suggested that a combination of UPLC/Q-TOF MS-based metabolomics and gene expression analysis can effectively elucidate the mechanism of triterpenoid saponin biosynthesis and can provide useful information on gene discovery. These findings can serve as a reference for using the overexpression of genes encoding for SQS, SQE, and/or β-AS to increase the triterpenoid saponin production of P. tenuifolia.

  1. UPLC/Q-TOF MS-based metabolomics and qRT-PCR in enzyme gene screening with key role in triterpenoid saponin biosynthesis of Polygala tenuifolia.

    Directory of Open Access Journals (Sweden)

    Fusheng Zhang

    Full Text Available The dried root of Polygala tenuifolia, named Radix Polygalae, is a well-known traditional Chinese medicine. Triterpenoid saponins are some of the most important components of Radix Polygalae extracts and are widely studied because of their valuable pharmacological properties. However, the relationship between gene expression and triterpenoid saponin biosynthesis in P. tenuifolia is unclear.In this study, ultra-performance liquid chromatography (UPLC coupled with quadrupole time-of-flight mass spectrometry (Q-TOF MS-based metabolomic analysis was performed to identify and quantify the different chemical constituents of the roots, stems, leaves, and seeds of P. tenuifolia. A total of 22 marker compounds (VIP>1 were explored, and significant differences in all 7 triterpenoid saponins among the different tissues were found. We also observed an efficient reference gene GAPDH for different tissues in this plant and determined the expression level of some genes in the triterpenoid saponin biosynthetic pathway. Results showed that MVA pathway has more important functions in the triterpenoid saponin biosynthesis of P. tenuifolia. The expression levels of squalene synthase (SQS, squalene monooxygenase (SQE, and beta-amyrin synthase (β-AS were highly correlated with the peak area intensity of triterpenoid saponins compared with data from UPLC/Q-TOF MS-based metabolomic analysis.This finding suggested that a combination of UPLC/Q-TOF MS-based metabolomics and gene expression analysis can effectively elucidate the mechanism of triterpenoid saponin biosynthesis and can provide useful information on gene discovery. These findings can serve as a reference for using the overexpression of genes encoding for SQS, SQE, and/or β-AS to increase the triterpenoid saponin production of P. tenuifolia.

  2. Isolation and structural characterization of echinocystic acid triterpenoid saponins from the Australian medicinal and food plant Acacia ligulata

    DEFF Research Database (Denmark)

    Knudsen, Diana Jæger; Ndi, Chi P.; Crocoll, Christoph

    2017-01-01

    The Australian plant Acacia ligulata has a number of traditional food and medicinal uses by Australian Aboriginal people, although no bioactive compounds have previously been isolated from this species. Bioassay-guided fractionation of an ethanolic extract of the mature pods of A. ligulata led...... to the isolation of the two new echinocystic acid triterpenoid saponins, ligulatasides A (1) and B (2), which differ in the fine structure of their glycan substituents. Their structures were elucidated on the basis of 1D and 2D NMR, GC-MS, LC-MS/MS, and saccharide linkage analysis. These are the first isolated...... compounds from A. ligulata and the first fully elucidated structures of triterpenoid saponins from Acacia sensu stricto having echinocystic acid reported as the aglycone. Compounds 1 and 2 were evaluated for cytotoxic activity against a human melanoma cancer cell line (SK-MEL28) and a diploid fibroblast...

  3. Isolation of Triterpenoid Glycoside from Bark of Terminalia arjuna using Chromatographic Technique and Investigation of Pharmacological Behavior upon Muscle Tissues

    Directory of Open Access Journals (Sweden)

    Tanushree Patnaik

    2007-01-01

    Full Text Available This study reports the isolation and characterization of a new triterpenoid glycoside extracted from the bark of Terminalia arjuna. The isolation of the organic compounds was done using simple chromatographic technique. Compound characterization using various spectroscopic technique identify the final isolated compound as Olean-3β,22β-diol-12-en-28β-D-glucopyranoside-oic acid. The method of isolation is simple, cost effective and efficient. The preliminary bioactivity of the compound was also evaluated.

  4. [HPLC-ELSD for determining contents of three triterpenoidal saponins in fruits of Buddleja lindleyana from different habitats].

    Science.gov (United States)

    Wu, Pei-Yun; Ren, Ya-Shuo; Wu, De-Ling; Qiao, Jin-Wei

    2016-04-01

    To establish an HPLC-ELSD method for the quantification of triterpenoids in the fruits of Buddleja lindleyana. The RP-HPLC-ELSD method was used for the determination of triterpenoids in B. lindleyana fruits, which were collected from different habitats. The column used was a packed with 5 μm stationary phase Waters SunFireTM C₁₈ (4.6 mm×150 mm, 5 μm). The mobile phase consisted of Methanol-water(82∶18) at a flow rate of 1 mL•min⁻¹. Column temperature: 30 ℃. ELSD conditions: drift tube temperature: 106 ℃; carrier gas (nitrogen) flow rate: 1.5 L•min⁻¹; amplification factor: 1. The calibration curves showed good linear relationship on a range from 0.702 to 28.08 μg(r=0.999 2) for Clinoposaponin III, 0.390 to 15.60 μg(r=0.998 9) for Desrhamnoverbascosaponin and 0.192 to 7.68μg(r=0.999 0) for Mimengoside I. The average recovery rate(n=6) were 99.41%, 99.08% and 98.67% and it's RSD were 0.86%, 1.56% and 1.80%. This method can be used to determine the contents of triterpenoids in the fruits of Buddleja lindleyana for its simplicity, accurateness and reliability. Copyright© by the Chinese Pharmaceutical Association.

  5. Cucurbitane Triterpenoids from the Fruits of Momordica Charantia Improve Insulin Sensitivity and Glucose Homeostasis in Streptozotocin-Induced Diabetic Mice.

    Science.gov (United States)

    Han, Joo-Hui; Tuan, Nguyen Quoc; Park, Min-Ho; Quan, Khong Trong; Oh, Joonseok; Heo, Kyung-Sun; Na, MinKyun; Myung, Chang-Seon

    2018-04-01

    Momordica charantia (M. charantia) has antidiabetic effects, and cucurbitane-type triterpenoid is one of the compounds of M. charantia. This study aims to investigate whether the new cucurbitane-type triterpenoids affect insulin sensitivity both in vitro and in vivo, and the underlying mechanisms. Four compounds (C1-C4) isolated from the ethanol extract of M. charantia enhance glucose uptake in C2C12 myotubes via insulin receptor substrate-1 (IRS-1) rather than via adenosine monophosphate-activated protein kinase. The most potent, compound 2 (C2), significantly increases the activation of IRS-1 and downstream signaling pathways, resulting in glucose transporter 4 translocation. Furthermore, these C2-induced in vitro effects are blocked by specific signal inhibitors. We further evaluate the antidiabetic effect of C2 using a streptozotocin (STZ)-induced diabetic mouse model. Consistent with in vitro data, treatment with C2 (1.68 mg kg -1 ) significantly decreases blood glucose level and enhances glycogen storage in STZ-injected mice. These effects appear to be mediated by the IRS-1 signaling pathway in skeletal muscle, not in adipose and liver tissues, suggesting that C2 improves hyperglycemia by increasing glucose uptake into skeletal muscle. Our findings demonstrate that the new cucurbitane-type triterpenoids have potential for prevention and management of diabetes by improving insulin sensitivity and glucose homeostasis. © 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  6. Antiprotozoal activity of extracts and isolated triterpenoids of 'carnauba' (Copernicia prunifera) wax from Brazil.

    Science.gov (United States)

    de Almeida, Buana C; Araújo, Bruno Q; Carvalho, Adonias A; Freitas, Sâmya Danielle L; Maciel, Dayany da S Alves; Ferreira, Ari José S; Tempone, Andre G; Martins, Ligia F; Alexandre, Tatiana R; Chaves, Mariana H; Lago, João Henrique G

    2016-12-01

    'Carnauba' wax is a natural product obtained from the processing of the powder exuded from Copernicia prunifera (Miller) H. E. Moore (Arecaceae). This material is widely used in the Brazilian folk medicine, including the treatment of rheumatism and syphilis. To investigate the antiprotozoal activity of hexane and EtOH extracts from the 'carnauba' wax as well as from the isolated compounds from the bioactive extracts. Two different samples of 'carnauba' (C. prunifera) waxes - types 1 and 4 - were individually extracted using hexane (EH) and EtOH (EE). Aliquots of hexane (type 1 - EH-1 and EH-4) and EtOH (type 4 - EE-1 and EE-4) extracts were tested against promastigote (2-200 μg/mL in DMSO during 48 h at 24 °C) and amastigote (3-150 μg/mL in DMSO during 120 h at 37 °C) forms of Leishmania infantum as well as against trypomastigote (3-150 μg/mL in DMSO during 24 h at 37 °C) forms of Trypanosoma cruzi. Bioactive extracts EH-1 and EE-4 were subjected to a bioactivity-guided fractionation to afford three dammarane-type triterpenoids (1-3). The in vitro antiprotozoal activities of the obtained compounds were evaluated as described above. Additionally, the cytotoxicity activity of compounds 1-3 against mammalian conjunctive cells (NCTC - 2-200 μg/mL in DMSO during 48 h at 37 °C) was determined. From the bioactive hexane and EtOH extracts from the 'carnauba' (C. prunifera) wax, were isolated three dammarane-type triterpenoids: (24R*)-methyldammar-25-ene-3β,20-diol (carnaubadiol, 1), (24R*)-methyldammara-20,25-dien-3-one (2) and (24R*)-methyldammara-20,25-dien-3α-ol (3). These compounds were identified based on the analysis of NMR and MS spectroscopic data. Compounds 1-3 were effective against the intracellular amastigotes of L. infantum, with IC 50 values ranging from 8 to 52 μM, while compounds 1 and 3 displayed activity against trypomastigote forms of T. cruzi with IC 50 values of 15 and 35 μM, respectively. The mammalian

  7. Antiviral effects of two Ganoderma lucidum triterpenoids against enterovirus 71 infection

    Energy Technology Data Exchange (ETDEWEB)

    Zhang, Wenjing; Tao, Junyan; Yang, Xiaoping [State Key Laboratory of Virology and College of Life Sciences, Wuhan University, Wuhan 430072 (China); Yang, Zhuliang [Key Laboratory of Biodiversity and Biogeography, Kunming Institute of Botany, Chinese Academy of Science, Kunming 650201 (China); Zhang, Li; Liu, Hongsheng [Department of Academy of Sciences, Liaoning University, Shenyang 110036 (China); Wu, Kailang [State Key Laboratory of Virology and College of Life Sciences, Wuhan University, Wuhan 430072 (China); Wu, Jianguo, E-mail: jwu@whu.edu.cn [State Key Laboratory of Virology and College of Life Sciences, Wuhan University, Wuhan 430072 (China)

    2014-07-04

    Highlights: • Triterpenoids GLTA and GLTB display anti-EV71 activities without cytotoxicity. • The compounds prevent EV71 infection by blocking adsorption of the virus to the cells. • GLTA and GLTB bind to EV71 capsid at the hydrophobic pocket to block EV71 uncoating. • The two compounds significantly inhibit the replication of EV71 viral RNA. • GLTA and GLTB may be used as potential therapeutic agents to treat EV71 infection. - Abstract: Enterovirus 71 (EV71) is a major causative agent for hand, foot and mouth disease (HFMD), and fatal neurological and systemic complications in children. However, there is currently no clinical approved antiviral drug available for the prevention and treatment of the viral infection. Here, we evaluated the antiviral activities of two Ganoderma lucidum triterpenoids (GLTs), Lanosta-7,9(11),24-trien-3-one,15;26-dihydroxy (GLTA) and Ganoderic acid Y (GLTB), against EV71 infection. The results showed that the two natural compounds display significant anti-EV71 activities without cytotoxicity in human rhabdomyosarcoma (RD) cells as evaluated by 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) cell proliferation assay. The mechanisms by which the two compounds affect EV71 infection were further elucidated by three action modes using Ribavirin, a common antiviral drug, as a positive control. The results suggested that GLTA and GLTB prevent EV71 infection through interacting with the viral particle to block the adsorption of virus to the cells. In addition, the interactions between EV71 virion and the compounds were predicated by computer molecular docking, which illustrated that GLTA and GLTB may bind to the viral capsid protein at a hydrophobic pocket (F site), and thus may block uncoating of EV71. Moreover, we demonstrated that GLTA and GLTB significantly inhibit the replication of the viral RNA (vRNA) of EV71 replication through blocking EV71 uncoating. Thus, GLTA and GLTB may represent two potential

  8. Antiviral effects of two Ganoderma lucidum triterpenoids against enterovirus 71 infection

    International Nuclear Information System (INIS)

    Zhang, Wenjing; Tao, Junyan; Yang, Xiaoping; Yang, Zhuliang; Zhang, Li; Liu, Hongsheng; Wu, Kailang; Wu, Jianguo

    2014-01-01

    Highlights: • Triterpenoids GLTA and GLTB display anti-EV71 activities without cytotoxicity. • The compounds prevent EV71 infection by blocking adsorption of the virus to the cells. • GLTA and GLTB bind to EV71 capsid at the hydrophobic pocket to block EV71 uncoating. • The two compounds significantly inhibit the replication of EV71 viral RNA. • GLTA and GLTB may be used as potential therapeutic agents to treat EV71 infection. - Abstract: Enterovirus 71 (EV71) is a major causative agent for hand, foot and mouth disease (HFMD), and fatal neurological and systemic complications in children. However, there is currently no clinical approved antiviral drug available for the prevention and treatment of the viral infection. Here, we evaluated the antiviral activities of two Ganoderma lucidum triterpenoids (GLTs), Lanosta-7,9(11),24-trien-3-one,15;26-dihydroxy (GLTA) and Ganoderic acid Y (GLTB), against EV71 infection. The results showed that the two natural compounds display significant anti-EV71 activities without cytotoxicity in human rhabdomyosarcoma (RD) cells as evaluated by 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) cell proliferation assay. The mechanisms by which the two compounds affect EV71 infection were further elucidated by three action modes using Ribavirin, a common antiviral drug, as a positive control. The results suggested that GLTA and GLTB prevent EV71 infection through interacting with the viral particle to block the adsorption of virus to the cells. In addition, the interactions between EV71 virion and the compounds were predicated by computer molecular docking, which illustrated that GLTA and GLTB may bind to the viral capsid protein at a hydrophobic pocket (F site), and thus may block uncoating of EV71. Moreover, we demonstrated that GLTA and GLTB significantly inhibit the replication of the viral RNA (vRNA) of EV71 replication through blocking EV71 uncoating. Thus, GLTA and GLTB may represent two potential

  9. Glucosidase inhibitory activity and antioxidant activity of flavonoid compound and triterpenoid compound from Agrimonia Pilosa Ledeb.

    Science.gov (United States)

    Liu, Xi; Zhu, Liancai; Tan, Jun; Zhou, Xuemei; Xiao, Ling; Yang, Xian; Wang, Bochu

    2014-01-10

    In Chinese traditional medicine, Agrimonia pilosa Ledeb (APL) exhibits great effect on treatment of type 2 diabetes mellitus (T2DM), however its mechanism is still unknown. Considering that T2DM are correlated with postprandial hyperglycemia and oxidative stress, we investigated the α-glucosidase inhibitory activity and the antioxidant activity of flavonoid compound (FC) and triterpenoid compound (TC) from APL. Entire plants of APL were extracted using 95% ethanol and 50% ethanol successively. The resulting extracts were partitioned and isolated by applying liquid chromatography using silica gel column and Sephadex LH 20 column to give FC and TC. The content of total flavonoids in FC and the content of total triterpenoids in TC were determined by using UV spectrophotometry. HPLC analysis was used to identify and quantify the monomeric compound in FC and TC. The α-glucosidase inhibitory activities were determined using the chromogenic method with p-nitrophenyl-α-D-glucopyranoside as substrate. Antioxidant activities were assessed through three kinds of radical scavenging assays (DPPH radical, ABTS radical and hydroxyl radical) & β-carotene-linoleic acid assay. The results indicate FC is abundant of quercitrin, and hyperoside, and TC is abundant of 1β, 2β, 3β, 19α-tetrahydroxy-12-en-28-oic acid (265.2 mg/g) and corosolic acid (100.9 mg/g). The FC & the TC have strong α-glucosidase inhibitory activities with IC50 of 8.72 μg/mL and 3.67 μg/mL, respectively. We find that FC show competitive inhibition against α-glucosidase, while the TC exhibits noncompetitive inhibition. Furthermore, The FC exhibits significant radical scavenging activity with the EC50 values of 7.73 μg/mL, 3.64 μg/mL and 5.90 μg/mL on DPPH radical, hydroxyl radical and ABTS radical, respectively. The FC also shows moderate anti-lipid peroxidation activity with the IC50 values of 41.77 μg/mL on inhibiting β-carotene bleaching. These results imply that the FC and the TC could be

  10. Regulation of the sperm calcium channel CatSper by endogenous steroids and plant triterpenoids.

    Science.gov (United States)

    Mannowetz, Nadja; Miller, Melissa R; Lishko, Polina V

    2017-05-30

    The calcium channel of sperm (CatSper) is essential for sperm hyperactivated motility and fertility. The steroid hormone progesterone activates CatSper of human sperm via binding to the serine hydrolase ABHD2. However, steroid specificity of ABHD2 has not been evaluated. Here, we explored whether steroid hormones to which human spermatozoa are exposed in the male and female genital tract influence CatSper activation via modulation of ABHD2. The results show that testosterone, estrogen, and hydrocortisone did not alter basal CatSper currents, whereas the neurosteroid pregnenolone sulfate exerted similar effects as progesterone, likely binding to the same site. However, physiological concentrations of testosterone and hydrocortisone inhibited CatSper activation by progesterone. Additionally, testosterone antagonized the effect of pregnenolone sulfate. We have also explored whether steroid-like molecules, such as the plant triterpenoids pristimerin and lupeol, affect sperm fertility. Interestingly, both compounds competed with progesterone and pregnenolone sulfate and significantly reduced CatSper activation by either steroid. Furthermore, pristimerin and lupeol considerably diminished hyperactivation of capacitated spermatozoa. These results indicate that ( i ) pregnenolone sulfate together with progesterone are the main steroids that activate CatSper and ( ii ) pristimerin and lupeol can act as contraceptive compounds by averting sperm hyperactivation, thus preventing fertilization.

  11. The Triterpenoid Betulin Protects against the Neuromuscular Effects of Bothrops jararacussu Snake Venom In Vivo

    Directory of Open Access Journals (Sweden)

    Miriéle Cristina Ferraz

    2015-01-01

    Full Text Available We confirmed the ability of the triterpenoid betulin to protect against neurotoxicity caused by Bothrops jararacussu snake venom in vitro in mouse isolated phrenic nerve-diaphragm (PND preparations and examined its capability of in vivo protection using the rat external popliteal/sciatic nerve-tibialis anterior (EPSTA preparation. Venom caused complete, irreversible blockade in PND (40 μg/mL, but only partial blockade (~30% in EPSTA (3.6 mg/kg, i.m. after 120 min. In PND, preincubation of venom with commercial bothropic antivenom (CBA attenuated the venom-induced blockade, and, in EPSTA, CBA given i.v. 15 min after venom also attenuated the blockade (by ~70% in both preparations. Preincubation of venom with betulin (200 μg/mL markedly attenuated the venom-induced blockade in PND; similarly, a single dose of betulin (20 mg, i.p., 15 min after venom virtually abolished the venom-induced decrease in contractility. Plasma creatine kinase activity was significantly elevated 120 min after venom injection in the EPSTA but was attenuated by CBA and betulin. These results indicate that betulin given i.p. has a similar efficacy as CBA given i.v. in attenuating the neuromuscular effects of B. jararacussu venom in vivo and could be a useful complementary measure to antivenom therapy for treating snakebite.

  12. The Triterpenoid Betulin Protects against the Neuromuscular Effects of Bothrops jararacussu Snake Venom In Vivo

    Science.gov (United States)

    Ferraz, Miriéle Cristina; de Oliveira, Jhones Luiz; de Oliveira Junior, Joel Reis; Cogo, José Carlos; dos Santos, Márcio Galdino; Franco, Luiz Madaleno; Puebla, Pilar; Ferraz, Helena Onishi; Ferraz, Humberto Gomes; da Rocha, Marisa Maria Teixeira; Hyslop, Stephen

    2015-01-01

    We confirmed the ability of the triterpenoid betulin to protect against neurotoxicity caused by Bothrops jararacussu snake venom in vitro in mouse isolated phrenic nerve-diaphragm (PND) preparations and examined its capability of in vivo protection using the rat external popliteal/sciatic nerve-tibialis anterior (EPSTA) preparation. Venom caused complete, irreversible blockade in PND (40 μg/mL), but only partial blockade (~30%) in EPSTA (3.6 mg/kg, i.m.) after 120 min. In PND, preincubation of venom with commercial bothropic antivenom (CBA) attenuated the venom-induced blockade, and, in EPSTA, CBA given i.v. 15 min after venom also attenuated the blockade (by ~70% in both preparations). Preincubation of venom with betulin (200 μg/mL) markedly attenuated the venom-induced blockade in PND; similarly, a single dose of betulin (20 mg, i.p., 15 min after venom) virtually abolished the venom-induced decrease in contractility. Plasma creatine kinase activity was significantly elevated 120 min after venom injection in the EPSTA but was attenuated by CBA and betulin. These results indicate that betulin given i.p. has a similar efficacy as CBA given i.v. in attenuating the neuromuscular effects of B. jararacussu venom in vivo and could be a useful complementary measure to antivenom therapy for treating snakebite. PMID:26633987

  13. The triterpenoids of Ganoderma tsugae prevent stress-induced myocardial injury in mice.

    Science.gov (United States)

    Kuok, Qian-Yu; Yeh, Chen-Yu; Su, Bor-Chyuan; Hsu, Pei-Ling; Ni, Hao; Liu, Ming-Yie; Mo, Fan-E

    2013-10-01

    Ganoderma mushrooms (Lingzhi in Chinese) have well-documented health benefits. Ganoderma tsugae (G. tsugae), one of the ganoderma species, has been commercially cultivated as a dietary supplement. Because G. tsugae has high antioxidant activity and because oxidative stress is often associated with cardiac injury, we hypothesized that G. tsugae protects against cardiac injury by alleviating oxidative stress. We tested the hypothesis using a work-overload-induced myocardial injury model created by challenging mice with isoproterenol (ISO). Remarkably, oral G. tsugae protected the mice from ISO-induced myocardial injury. Moreover, the triterpenoid fraction of G. tsugae, composed of a mixture of nine structurally related ganoderic acids (GAs), provided cardioprotection by inhibiting the ISO-induced expression of Fas/Fas ligand, oxidative stress, and apoptosis. The antioxidant activity of GAs was tested in cultured cardio-myoblast H9c2 cells against the insult of H₂O₂. GAs dissipated the cellular reactive oxygen species imposed by H₂O₂ and prevented cell death. Our findings uncovered the cardioprotective activity of G. tsugae and identified GAs as the bioactive components against cardiac insults. © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  14. Immunochromatographic strip assay for detection of bioactive Ganoderma triterpenoid, ganoderic acid A in Ganoderma lingzhi.

    Science.gov (United States)

    Sakamoto, Seiichi; Kikkawa, Nao; Kohno, Toshitaka; Shimizu, Kuniyoshi; Tanaka, Hiroyuki; Morimoto, Satoshi

    2016-10-01

    Ganoderic acid A (GAA) is one of the major Ganoderma triterpenes produced by medicinal mushroom belonging to the genus Ganoderma (Ganodermataceae). Due to its interesting pharmacological activities, Ganoderma species have been traditionally used in China for the treatment of various diseases. Herein, we developed a colloidal gold-based immunochromatographic strip assay (ICA) for the rapid detection of GAA using highly specific monoclonal antibody against GAA (MAb 12A) conjugated with gold nanoparticles. Using the developed ICA, the detection of GAA can be completed within 15min after dipping the test strip into an analyte solution with the limit of detection (LOD) for GAA of ~500ng/mL. In addition, this system makes it possible to perform a semi-quantitative analysis of GAA in Ganoderma lingzhi, where high reliability was evaluated by enzyme-linked immunosorbent assay (ELISA). The newly developed ICA can potentially be applied to the standardization of Ganoderma using GAA as an index because GAA is major triterpenoid present much in the mushroom. Copyright © 2016. Published by Elsevier B.V.

  15. Bioactivity-guided isolation of antioxidant triterpenoids from Betula platyphylla var. japonica bark.

    Science.gov (United States)

    Eom, Hee Jeong; Kang, Hee Rae; Kim, Ho Kyong; Jung, Eun Bee; Park, Hyun Bong; Kang, Ki Sung; Kim, Ki Hyun

    2016-06-01

    The bark of Betula platyphylla var. japonica (Betulaceae) has been used to treat pneumonia, choloplania, nephritis, and chronic bronchitis. This study aimed to investigate the bioactive chemical constituents of the bark of B. platyphylla var. japonica. A bioassay-guided fractionation and chemical investigation of the bark of B. platyphylla var. japonica resulted in the isolation and identification of a new lupane-type triterpene, 27-hydroxybetunolic acid (1), along with 18 known triterpenoids (2-19). The structure of the new compound (1) was elucidated on the basis of 1D and 2D NMR spectroscopic data analysis as well as HR-ESIMS. Among the known compounds, chilianthin B (17), chilianthin C (18), and chilianthin A (19) were triterpene-lignan esters, which are rarely found in nature. Compounds 4, 6, 7, 17, 18, and 19 showed significant antioxidant activities with IC50 values in the range 4.48-43.02μM in a DPPH radical-scavenging assay. However, no compound showed significant inhibition of acetylcholine esterase (AChE). Unfortunately, the new compound (1) exhibited no significance in both biological activities. This study strongly suggests that B. platyphylla var. japonica bark is a potential source of natural antioxidants for use in pharmaceuticals and functional foods. Copyright © 2016 Elsevier Inc. All rights reserved.

  16. Fast separation of triterpenoid saponins using supercritical fluid chromatography coupled with single quadrupole mass spectrometry.

    Science.gov (United States)

    Huang, Yang; Zhang, Tingting; Zhou, Haibo; Feng, Ying; Fan, Chunlin; Chen, Weijia; Crommen, Jacques; Jiang, Zhengjin

    2016-03-20

    Triterpenoid saponins (TSs) are the most important components of some traditional Chinese medicines (TCMs) and have exhibited valuable pharmacological properties. In this study, a rapid and efficient method was developed for the separation of kudinosides, stauntosides and ginsenosides using supercritical fluid chromatography coupled with single quadrupole mass spectrometry (SFC-MS). The separation conditions for the selected TSs were carefully optimized after the initial screening of eight stationary phases. The best compromise for all compounds in terms of chromatographic performance and MS sensitivity was obtained when water (5-10%) and formic acid (0.05%) were added to the supercritical carbon dioxide/MeOH mobile phase. Beside the composition of the mobile phase, the nature of the make-up solvent for interfacing SFC with MS was also evaluated. Compared to reversed phase liquid chromatography, the SFC approach showed higher resolution and shorter running time. The developed SFC-MS methods were successfully applied to the separation and identification of TSs present in Ilex latifolia Thunb., Panax quinquefolius L. and Panax ginseng C.A. Meyer. These results suggest that this SFC-MS approach could be employed as a useful tool for the quality assessment of natural products containing TSs as active components. Copyright © 2015 Elsevier B.V. All rights reserved.

  17. Reduction of Myeloid-derived Suppressor Cells and Lymphoma Growth by a Natural Triterpenoid

    Science.gov (United States)

    Radwan, Faisal F. Y.; Hossain, Azim; God, Jason M.; Leaphart, Nathan; Elvington, Michelle; Nagarkatti, Mitzi; Tomlinson, Stephen; Haque, Azizul

    2016-01-01

    Lymphoma is a potentially life threatening disease. The goal of this study was to investigate the therapeutic potential of a natural triterpenoid, Ganoderic acid A (GA-A) in controlling lymphoma growth both in vitro and in vivo. Here, we show that GA-A treatment induces caspase-dependent apoptotic cell death characterized by a dose-dependent increase in active caspases 9 and 3, up-regulation of pro-apoptotic BIM and BAX proteins, and a subsequent loss of mitochondrial membrane potential with release of cytochrome c. In addition to GA-A’s anti-growth activity, we show that lower doses of GA-A enhance HLA class II-mediated antigen presentation and CD4+ T cell recognition of lymphoma in vitro. The therapeutic relevance of GA-A treatment was also tested in vivo using the EL4 syngeneic mouse model of metastatic lymphoma. GA-A-treatment significantly prolonged survival of EL4 challenged mice and decreased tumor metastasis to the liver, an outcome accompanied by a marked down-regulation of STAT3 phosphorylation, reduction myeloid-derived suppressor cells (MDSCs), and enhancement of cytotoxic CD8+ T cells in the host. Thus, GA-A not only selectively induces apoptosis in lymphoma cells, but also enhances cell-mediated immune responses by attenuating MDSCs, and elevating Ag presentation and T cell recognition. The demonstrated therapeutic benefit indicates that GA-A is a candidate for future drug design for the treatment of lymphoma. PMID:25142864

  18. Cloning and characterization of oxidosqualene cyclases from Kalanchoe daigremontiana: enzymes catalyzing up to 10 rearrangement steps yielding friedelin and other triterpenoids.

    Science.gov (United States)

    Wang, Zhonghua; Yeats, Trevor; Han, Hong; Jetter, Reinhard

    2010-09-24

    The first committed step in triterpenoid biosynthesis is the cyclization of oxidosqualene to polycyclic alcohols or ketones C(30)H(50)O. It is catalyzed by single oxidosqualene cyclase (OSC) enzymes that can carry out varying numbers of carbocation rearrangements and, thus, generate triterpenoids with diverse carbon skeletons. OSCs from diverse plant species have been cloned and characterized, the large majority of them catalyzing relatively few rearrangement steps. It was recently predicted that special OSCs must exist that can form friedelin, the pentacyclic triterpenoid whose formation involves the maximum possible number of rearrangement steps. The goal of the present study, therefore, was to clone a friedelin synthase from Kalanchoe daigremontiana, a plant species known to accumulate this triterpenoid in its leaf surface waxes. Five OSC cDNAs were isolated, encoding proteins with 761-779 amino acids and sharing between 57.4 and 94.3% nucleotide sequence identity. Heterologous expression in yeast and GC-MS analyses showed that one of the OSCs generated the steroid cycloartenol together with minor side products, whereas the other four enzymes produced mixtures of pentacyclic triterpenoids dominated by lupeol (93%), taraxerol (60%), glutinol (66%), and friedelin (71%), respectively. The cycloartenol synthase was found expressed in all leaf tissues, whereas the lupeol, taraxerol, glutinol, and friedelin synthases were expressed only in the epidermis layers lining the upper and lower surfaces of the leaf blade. It is concluded that the function of these enzymes is to form respective triterpenoid aglycones destined to coat the leaf exterior, probably as defense compounds against pathogens or herbivores.

  19. A novel 3α-p-Nitrobenzoylmultiflora-7:9(11)-diene-29-benzoate and two new triterpenoids from the seeds of zucchini (Cucurbita pepo L).

    Science.gov (United States)

    Tanaka, Reiko; Kikuchi, Takashi; Nakasuji, Saori; Ue, Yasuhiro; Shuto, Daisuke; Igarashi, Keishi; Okada, Rina; Yamada, Takeshi

    2013-06-26

    Three novel multiflorane-type triterpenoids, 3α-p-nitrobenzoylmultiflora-7:9(11)-diene-29-benzoate (1), 3α-acetoxymultiflora-7:9(11)-diene-29-benzoate (2), and 3α-acetoxymultiflora-5(6):7:9(11)-triene-29-benzoate (3), along with two known related compounds 4 and 5 were isolated from the seeds of zucchini (Cucurbita pepo L). Their structures were determined on the basis of 1D and 2D NMR spectroscopy and HREIMS. Triterpenoids possessing a nitro group were not isolated previously.

  20. Studies on the constituents of Gentiana species. II. A new triterpenoid, and (S)-(+)- and (R)-(-)-gentiolactones from Gentiana lutea.

    Science.gov (United States)

    Kakuda, Rie; Machida, Koichi; Yaoita, Yasunori; Kikuchi, Masafumi; Kikuchi, Masao

    2003-07-01

    A new triterpenoid, 12-ursene-3beta, 11alpha-diol 3-O-palmitate (1), has been isolated from the rhizomes and roots of Gentiana lutea, together with the artificial diene derivative, 9 (11), 12-ursadien-3beta-ol 3-O-palmitate (1a) and five known compounds (3-7). Their structures were established on the basis of spectral analysis. In addition, (+/-)-gentiolactone [(+/-)-2], isolated from this plant, was successfully separated into its enantiomers [(+)-2, (-)-2] for the first time, and the absolute configurations at C-9 of (+)-2, (-)-2 were assigned as S and R, respectively, from the optical rotations and the circular dichroism (CD) spectral data.

  1. [Studies on technology optimization for extracting triterpenoid saponins from Picria felterrae by multi-target grading method].

    Science.gov (United States)

    Fang, Hong; Ning, De-sheng; Liang, Xiao-yan

    2009-12-01

    To study the optimum extraction conditions of triterpenoid saponins from Picria felterrae. The optimum extraction conditions were investigated by the contents of the total glycosides and picfeltarraenine I A and I B, using orthogonal test. The optimum extraction conditions were as follows: using 70% alcohol of 19 times than the amount of original material soaking 3 hours, extracting twice with hot reflux method at 80 degrees C, 3h the first time, 1 h the second time. The selected extraction conditions are convenient and practical with high accuracy, and could be used as a reference for industrial production.

  2. Ingasaponin, a complex triterpenoid saponin with immunological adjuvant activity from Inga laurina.

    Science.gov (United States)

    Cruz, Maria de Fátima Simão Jucá; Pereira, Gabriela Moysés; Ribeiro, Marcela Gonçalves; da Silva, Ari Miranda; Tinoco, Luzineide Wanderley; da Silva, Bernadete Pereira; Parente, José Paz

    2016-02-01

    As part of our search of bioactive saponins from Brazilian plants, phytochemical study of the seeds of Inga laurina led to the isolation of a new complex triterpenoid saponin, named ingasaponin. It is the first saponin isolated from a species of Inga genus. It was isolated by using chromatographic methods and its structural elucidation was performed using detailed analyses of (1)H and (13)C NMR spectra including 2D-NMR spectroscopic techniques and chemical conversions. Its structure was established as 21-[[(2E,6S)-6-[[6-deoxy-4-O-[(2E,6S)-6-[(β-D-glucopyranosyl)oxy]-2,6-dimethyl-1-oxo-2,7-octadienyl]-[(β-D-glucopyranosyl)oxy]-2,6-dimethyl-1-oxo-2,7-octadienyl]-[(β-D-glucopyranosyl)oxy]-2,6-dimethyl-1-oxo-2,7-octadienyl]-[(β-D-glucopyranosyl)oxy]-2-(hydroxymethyl)-6-methyl-1-oxo-2,7-octadienyl]oxy]-16-hydroxy-3-[[O-β-D-xylopyranosyl-(1 → 2)-O-α-L-arabinopyranosyl-(1 → 6)-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl]oxy]-(3β,16α,21β)-olean-12-en-28-oic acid O-α-L-arabinofuranosyl-(1 → 4)-O-[β-D-glucopyranosyl-(1 → 3)]-O-6-deoxy-α-L-mannopyranosyl-(1 → 2)-β-D-glucopyranosyl ester (1). The hemolytic potential of 1 was evaluated using in vitro assays, and its adjuvant activity on the cellular immune response against ovalbumin antigen was investigated using in vivo models. Copyright © 2015 Elsevier Ltd. All rights reserved.

  3. Reduction of myeloid-derived suppressor cells and lymphoma growth by a natural triterpenoid.

    Science.gov (United States)

    Radwan, Faisal F Y; Hossain, Azim; God, Jason M; Leaphart, Nathan; Elvington, Michelle; Nagarkatti, Mitzi; Tomlinson, Stephen; Haque, Azizul

    2015-01-01

    Lymphoma is a potentially life threatening disease. The goal of this study was to investigate the therapeutic potential of a natural triterpenoid, Ganoderic acid A (GA-A) in controlling lymphoma growth both in vitro and in vivo. Here, we show that GA-A treatment induces caspase-dependent apoptotic cell death characterized by a dose-dependent increase in active caspases 9 and 3, up-regulation of pro-apoptotic BIM and BAX proteins, and a subsequent loss of mitochondrial membrane potential with release of cytochrome c. In addition to GA-A's anti-growth activity, we show that lower doses of GA-A enhance HLA class II-mediated antigen (Ag) presentation and CD4+ T cell recognition of lymphoma cells in vitro. The therapeutic relevance of GA-A treatment was also tested in vivo using the EL4 syngeneic mouse model of metastatic lymphoma. GA-A-treatment significantly prolonged survival of EL4 challenged mice and decreased tumor metastasis to the liver, an outcome accompanied by a marked down-regulation of STAT3 phosphorylation, reduction myeloid-derived suppressor cells (MDSCs), and enhancement of cytotoxic CD8+ T cells in the host. Thus, GA-A not only selectively induces apoptosis in lymphoma cells, but also enhances cell-mediated immune responses by attenuating MDSCs, and elevating Ag presentation and T cell recognition. The demonstrated therapeutic benefit indicates that GA-A is a candidate for future drug design for the treatment of lymphoma. © 2014 Wiley Periodicals, Inc.

  4. Antiparasitic activity of natural and semi-synthetic tirucallane triterpenoids from Schinus terebinthifolius (Anacardiaceae): structure/activity relationships.

    Science.gov (United States)

    Morais, Thiago R; da Costa-Silva, Thais A; Tempone, Andre G; Borborema, Samanta Etel T; Scotti, Marcus T; de Sousa, Raquel Maria F; Araujo, Ana Carolina C; de Oliveira, Alberto; de Morais, Sérgio Antônio L; Sartorelli, Patricia; Lago, João Henrique G

    2014-05-05

    Leishmaniasis and Chagas are diseases caused by parasitic protozoans that affect the poorest population in the World, causing a high mortality and morbidity. As a result of highly toxic and long-term treatments, the discovery of novel, safe and more efficacious drugs is essential. In this work, the in vitro antiparasitic activity and mammalian cytotoxicity of three natural tirucallane triterpenoids, isolated from leaves of Schinus terebinthifolius (Anacardiaceae), and nine semi-synthetic derivatives were investigated against Leishmania (L.) infantum and Trypanosoma cruzi. Trypomastigotes of T. cruzi were the most susceptible parasites and seven compounds demonstrated a trypanocidal activity with IC50 values in the range between 15 and 58 µg/mL. Four compounds demonstrated selectivity towards the intracellular amastigotes of Leishmania, with IC50 values in the range between 28 and 97 µg/mL. The complete characterization of triterpenoids was afforded after thorough analysis of nuclear magnetic resonance (NMR) data as well as electrospray ionization mass spectrometry (ESI-MS). Additionally, structure-activity relationships were performed using Decision Trees.

  5. Antiparasitic Activity of Natural and Semi-Synthetic Tirucallane Triterpenoids from Schinus terebinthifolius (Anacardiaceae: Structure/Activity Relationships

    Directory of Open Access Journals (Sweden)

    Thiago R. Morais

    2014-05-01

    Full Text Available Leishmaniasis and Chagas are diseases caused by parasitic protozoans that affect the poorest population in the World, causing a high mortality and morbidity. As a result of highly toxic and long-term treatments, the discovery of novel, safe and more efficacious drugs is essential. In this work, the in vitro antiparasitic activity and mammalian cytotoxicity of three natural tirucallane triterpenoids, isolated from leaves of Schinus terebinthifolius (Anacardiaceae, and nine semi-synthetic derivatives were investigated against Leishmania (L. infantum and Trypanosoma cruzi. Trypomastigotes of T. cruzi were the most susceptible parasites and seven compounds demonstrated a trypanocidal activity with IC50 values in the range between 15 and 58 µg/mL. Four compounds demonstrated selectivity towards the intracellular amastigotes of Leishmania, with IC50 values in the range between 28 and 97 µg/mL. The complete characterization of triterpenoids was afforded after thorough analysis of nuclear magnetic resonance (NMR data as well as electrospray ionization mass spectrometry (ESI-MS. Additionally, structure-activity relationships were performed using Decision Trees.

  6. Structure-activity relationships of lanostane-type triterpenoids from Ganoderma lingzhi as α-glucosidase inhibitors.

    Science.gov (United States)

    Fatmawati, Sri; Kondo, Ryuichiro; Shimizu, Kuniyoshi

    2013-11-01

    A series of lanostane-type triterpenoids, identified as ganoderma alcohols and ganoderma acids, were isolated from the fruiting body of Ganoderma lingzhi. Some of these compounds were confirmed as active inhibitors of the in vitro human recombinant aldose reductase. This paper aims to explain the structural requirement for α-glucosidase inhibition. Our structure-activity studies of ganoderma alcohols showed that the OH substituent at C-3 and the double-bond moiety at C-24 and C-25 are necessary to increase α-glucosidase inhibitory activity. The structure-activity relationships of ganoderma acids revealed that the OH substituent at C-11 is an important feature and that the carboxylic group in the side chain is essential for the recognition of α-glucosidase inhibitory activity. Moreover, the double-bond moiety at C-20 and C-22 in the side chain and the OH substituent at C-3 of ganoderma acids improve α-glucosidase inhibitory activity. These results provide an approach with which to consider the structural requirements of lanostane-type triterpenoids from G. lingzhi. An understanding of these requirements is considered necessary in order to improve a new type of α-glucosidase inhibitor. Copyright © 2013 Elsevier Ltd. All rights reserved.

  7. Pesticidal and pest repellency activities of a plant derived triterpenoid 2α,3β,21β,23,28-penta hydroxyl 12-oleanene against Tribolium castaneum

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    Alam Khan

    2014-01-01

    Full Text Available BACKGROUND: Tribolium castaneum (Herbst is a major pest of stored grain-based products, and cause severe damage to cereal grains throughout the world. The present investigation was aimed to determine the pesticidal and pest repellent activities of 2α,3β,21β,23,28-penta hydroxyl 12-oleanene against T. castaneum. The compound 2α,3β,21β,23,28-penta hydroxyl 12-oleanene is a triterpenoid which was isolated from the roots of Laportea crenulata Gaud. Surface film technique was used for pesticidal screening, whereas, pest repellency property of the triterpenoid was determined by filter paper disc method. RESULTS: At 24 hours of exposure duration, significant mortality records (80% and 86% were observed at doses 0.88 and 1.77 mg/cm². No significant change in mortality records was observed when duration of exposure was increased up to 48 hours. The triterpenoid showed significant repellency activity at doses 0.47 and 0.94 mg/cm². CONCLUSION: These data suggest that the triterpenoid 2α,3β,21β,23,28-penta hydroxyl 12-oleanene possess both pesticidal and pest repellency activities against T. castaneum and can be used in controlling the pest of grain-based products.

  8. A WRKY transcription factor from Withania somnifera regulates triterpenoid withanolide accumulation and biotic stress tolerance through modulation of phytosterol and defense pathways.

    Science.gov (United States)

    Singh, Anup Kumar; Kumar, Sarma Rajeev; Dwivedi, Varun; Rai, Avanish; Pal, Shaifali; Shasany, Ajit K; Nagegowda, Dinesh A

    2017-08-01

    Withania somnifera produces pharmacologically important triterpenoid withanolides that are derived via phytosterol pathway; however, their biosynthesis and regulation remain to be elucidated. A jasmonate- and salicin-inducible WRKY transcription factor from W. somnifera (WsWRKY1) exhibiting correlation with withaferin A accumulation was functionally characterized employing virus-induced gene silencing and overexpression studies combined with transcript and metabolite analyses, and chromatin immunoprecipitation assay. WsWRKY1 silencing resulted in stunted plant growth, reduced transcripts of phytosterol pathway genes with corresponding reduction in phytosterols and withanolides in W. somnifera. Its overexpression elevated the biosynthesis of triterpenoids in W. somnifera (phytosterols and withanolides), as well as tobacco and tomato (phytosterols). Moreover, WsWRKY1 binds to W-box sequences in promoters of W. somnifera genes encoding squalene synthase and squalene epoxidase, indicating its direct regulation of triterpenoid pathway. Furthermore, while WsWRKY1 silencing in W. somnifera compromised the tolerance to bacterial growth, fungal infection, and insect feeding, its overexpression in tobacco led to improved biotic stress tolerance. Together these findings demonstrate that WsWRKY1 has a positive regulatory role on phytosterol and withanolides biosynthesis, and defense against biotic stress, highlighting its importance as a metabolic engineering tool for simultaneous improvement of triterpenoid biosynthesis and plant defense. © 2017 The Authors. New Phytologist © 2017 New Phytologist Trust.

  9. Triterpenóides tipo cicloartano de própolis de Teresina - PI Cycloartane triterpenoids of propolis from Teresina - PI

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    Maria do Socorro Sousa da Silva

    2005-10-01

    Full Text Available The chemical study of the propolis produced in Teresina city, state of Piaui, resulted in the identification of six cycloartane triterpenoids: isomangiferolic acid, 24-methylenecycloartane-3beta,26-diol, mangiferolic acid, mangiferonic acid, ambonic acid and ambolic acid. The substances were characterized by one and two-dimensional ¹H and 13C NMR analysis.

  10. Isolation and identification of an antiparasitic triterpenoid estersaponin from the stem bark of Pittosporum mannii (Pittosporaceae

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    Kennedy D Nyongbela

    2013-10-01

    Full Text Available Objective: To screen for antiparasitic properties of Pittosporum mannii Hook (Pittosporaceae through in vitro bioassay tests and to identify the bioactive compound(s. Methods: The stem bark of Pittosporum mannii was harvested in Bali Nyonga in January 2007. The CH 2Cl2 and MeOH extracts were tested in vitro for antiparasitic activity. NF54 (an airport strain of unknown origin and sensitive to all known drugs and K1 (a clone originating from Thailand and resistant to chloroquine/pyrimethamine strains were used for the antiplasmodial screening while Leishmania donovani MHOM-ET-67/L82 was used for antileishmanial testing. 1H and 13C NMR spectra were recorded on a Bruker AMX-500 spectrometer using CDCl3 as solvent. EIMS were recorded on a double-focusing mass spectrometer (Varian MAT 311A while HREIMS were recorded on a JEOL HX 110 mass spectrometer. Results: The MeOH extract was active on both the chloroquine-resistant (K1 strain (IC50=4.3 μg/ mL and on the macrophages of Leishmania donovani (IC50=8.6 μg/mL. The CH2Cl2 extract was considered inactive on both parasites (IC50>5.0 μg/mL and 21.7 μg/mL respectively. Compound 1, a constituent that precipitated from the MeOH extract, showed pronounced activity on both Plasmodium falciparum and Leishmania donovani parasites (IC 50=1.02 and 1.80 μg/mL respectively with artemisinin and miltefosine included as reference drugs. Its structure was identified as 1-O-[apha-L-(Rhamnopyranosyl]-23-acetoxyimberbic acid 29-methyl ester, a pentacyclic triterpenoid estersaponin. Conclusions: The present study constitutes the first report on the antiparasitic activity of this plant and provides some support for the traditional use of the plant in the treatment of malaria. The plant has therefore been identified as a potential source for the discovery of antiparasitic lead compounds.

  11. Cytotoxic lanostane-type triterpenoids from the fruiting bodies of Ganoderma lucidum and their structure–activity relationships

    Science.gov (United States)

    Wang, Zhanggen; Su, Jiyan; Jiao, Chunwei; Xie, Yizhen; Yang, Burton B.

    2017-01-01

    We conducted a study of Ganoderma lucidum metabolites and isolated 35 lanostane-type triterpenoids, including 5 new ganoderols (1-5). By spectroscopy, we compared the structures of these compounds with known related compounds in this group. All of the isolated compounds were assayed for their effect against the human breast carcinoma cell line MDA-MB-231 and hepatocellular carcinoma cell line HepG2. Corresponding three-dimensional quantitative structure–activity relationship (3D-QSAR) models were built and analyzed using Discovery Studio. These results provide further evidence for anti-cancer constituents within Ganoderma lucidum, and may provide a theoretical foundation for designing novel therapeutic compounds. PMID:28052025

  12. A Triterpenoid from Thalictrum fortunei Induces Apoptosis in BEL-7402 Cells Through the P53-Induced Apoptosis Pathway

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    Lvyi Chen

    2011-11-01

    Full Text Available Thalictrum fortunei S. Moore, a perennial plant distributed in the southeastern part of China, has been used in Traditional Chinese Medicine for thousands of years for its antitumor, antibacterial and immunoregulatory effects. In order to investigate the active components and the mechanism of the anti-tumor effects of Thalictrum fortunei, the growth inhibitory effects of eight triterpenoids isolated from the aerial parts of the plant on tumor cell lines were examined by 3-(4,5-dimethylthiazoy1-3,5-diphenyltetrazolium bromide (MTT assay. The MTT-assay results showed that the inhibitory activity of 3-O-β-D-glucopyranosyl-(1→4-β-D-fucopyranosyl(22S,24Z-cycloart-24-en-3β,22,26-triol 26-O-β-D-glucopyranoside (1 was stronger than that of the other seven tested triterpenoids on human hepatoma Bel-7402 cell line (Bel-7402, human colon lovo cells (LoVo, human non-small cells lung cancer NCIH-460 cells (NCIH-460 and human gastric carcinoma SGC-7901 cells (SGC-7901 after 48 h treatment in vitro, with the IC50 values of 66.4, 84.8, 73.5, 89.6 μM, respectively. Moreover, the antitumor mechanism of compound 1 on Bel-7402 cell was explored through nucleus dyeing, fluorescence assay, flow cytometry and western blot. The flow cytometric analysis results revealed that compound 1 caused apoptosis and mitochondrial membrane potential (MMP loss in Bel-7402 cells. A fluorescence assay indicated that intracellular reactive oxygen species (ROS were markedly provoked by compound 1 treatment compared to control cells. Immunoblot results showed that compound 1 significantly increased the expression levels of cleaved caspase-3, P53 and Bax protein, and decreased the expression level of Bcl-2 protein. These findings indicate that compound 1 inhibits the growth activity of tumor cells, probably through the P53 protein-induced apoptosis pathway.

  13. Ganoderma Triterpenoids Exert Antiatherogenic Effects in Mice by Alleviating Disturbed Flow-Induced Oxidative Stress and Inflammation

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    Pei-Ling Hsu

    2018-01-01

    Full Text Available Ganoderma mushrooms, used in traditional Chinese medicine to promote health and longevity, have become widely accepted as herbal supplements. Ganoderma lucidum (GL, a commonly seen ganoderma species, is commercially cultivated under controlled conditions for more consistent chemical composition. The medicinal properties of GL are attributable to its antioxidant and anti-inflammatory activities. We intended to assess the effect of GL in atherosclerosis, an arterial condition associated with chronic oxidative stress and inflammation, using a carotid-artery-ligation mouse model. Flow turbulence created in the ligated artery induces oxidative stress and neointimal hyperplasia, a feature of early atherogenesis. Daily oral GL prevented neointimal thickening 2 weeks after ligation. Moreover, the ganoderma triterpenoid (GT crude extract isolated from GL abolished ligation-induced neointima formation. Mechanistically, endothelial dysfunction was observed 3 days after ligation before any structural changes could be detected. GTs alleviated the oxidative stress and restored the atheroresistent status of endothelium by inhibiting the induction of a series of atherogenic factors, including endothelin-1, von Willebrand factor, and monocyte chemoattractant protein-1 after 3-day ligation. The anti-inflammatory activity of GTs was tested in cultured human umbilical vein endothelial cells (HUVECs exposed to disturbed flow in an in vitro perfusion system. GTs abolished the induction of proinflammatory VCAM-1, TNF-α, and IL-6 by oscillatory shear stress. Moreover, the antioxidant activity of GTs was tested in HUVECs against the insult of H2O2. GTs dissipated the cellular superoxide accumulation imposed by H2O2, thereby mitigating H2O2-induced cell damage and proatherogenic response. Our results revealed the atheroprotective properties of ganoderma mushrooms and identified triterpenoids as the critical constituents for those effects. GTs prevent atherogenesis by

  14. Triterpenoids from Ocimum labiatum Activates Latent HIV-1 Expression In Vitro: Potential for Use in Adjuvant Therapy

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    Petrina Kapewangolo

    2017-10-01

    Full Text Available Latent HIV reservoirs in infected individuals prevent current treatment from eradicating infection. Treatment strategies against latency involve adjuvants for viral reactivation which exposes viral particles to antiretroviral drugs. In this study, the effect of novel triterpenoids isolated from Ocimum labiatum on HIV-1 expression was measured through HIV-1 p24 antigen capture in the U1 latency model of HIV-1 infection and in peripheral blood mononuclear cells (PBMCs of infected patients on combination antiretroviral therapy (cART. The mechanism of viral reactivation was determined through the compound’s effect on cytokine production, histone deacetylase (HDAC inhibition, and protein kinase C (PKC activation. Cytotoxicity of the triterpenoids was determined using a tetrazolium dye and flow cytometry. The isolated triterpene isomers, 3-hydroxy-4,6a,6b,11,12,14b-hexamethyl-1,2,3,4,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-octadecahydropicene-4,8a-dicarboxylic acid (HHODC, significantly (p < 0.05 induced HIV-1 expression in a dose-dependent manner in U1 cells at non-cytotoxic concentrations. HHODC also induced viral expression in PBMCs of HIV-1 infected patients on cART. In addition, the compound up-regulated the production of interleukin (IL-2, IL-6, tumour necrosis factor (TNF-α, and interferon (IFN-γ but had no effect on HDAC and PKC activity, suggesting cytokine upregulation as being involved in latency activation. The observed in vitro reactivation of HIV-1 introduces the adjuvant potential of HHODC for the first time here.

  15. Mevalonate-derived quinonemethide triterpenoid from in vitro roots of Peritassa laevigata and their localization in root tissue by MALDI imaging

    Science.gov (United States)

    Pina, Edieidia S.; Silva, Denise B.; Teixeira, Simone P.; Coppede, Juliana S.; Furlan, Maysa; França, Suzelei C.; Lopes, Norberto P.; Pereira, Ana Maria S.; Lopes, Adriana A.

    2016-03-01

    Biosynthetic investigation of quinonemethide triterpenoid 22β-hydroxy-maytenin (2) from in vitro root cultures of Peritassa laevigata (Celastraceae) was conducted using 13C-precursor. The mevalonate pathway in P. laevigata is responsible for the synthesis of the quinonemethide triterpenoid scaffold. Moreover, anatomical analysis of P. laevigata roots cultured in vitro and in situ showed the presence of 22β-hydroxy-maytenin (2) and maytenin (1) in the tissues from transverse or longitudinal sections with an intense orange color. MALDI-MS imaging confirmed the distribution of (2) and (1) in the more distal portions of the root cap, the outer cell layers, and near the vascular cylinder of P. laevigata in vitro roots suggesting a role in plant defense against infection by microorganisms as well as in the root exudation processes.

  16. Triterpenoid herbal saponins enhance beneficial bacteria, decrease sulfate-reducing bacteria, modulate inflammatory intestinal microenvironment and exert cancer preventive effects in ApcMin/+ mice

    OpenAIRE

    Chen, Lei; Brar, Manreetpal S.; Leung, Frederick C. C.; Hsiao, W. L. Wendy

    2016-01-01

    Saponins derived from medicinal plants have raised considerable interest for their preventive roles in various diseases. Here, we investigated the impacts of triterpenoid saponins isolated from Gynostemma pentaphyllum (GpS) on gut microbiome, mucosal environment, and the preventive effect on tumor growth. Six-week old ApcMin/+ mice and their wild-type littermates were fed either with vehicle or GpS daily for the duration of 8 weeks. The fecal microbiome was analyzed by enterobacterial repetit...

  17. The total triterpenoid saponins of Xanthoceras sorbifolia improve learning and memory impairments through against oxidative stress and synaptic damage.

    Science.gov (United States)

    Ji, Xue-Fei; Chi, Tian-Yan; Liu, Peng; Li, Lu-Yi; Xu, Ji-Kai; Xu, Qian; Zou, Li-Bo; Meng, Da-Li

    2017-02-15

    X. sorbifolia is a widely cultivated ecologicalcrop in the north of China which is used to produce biodiesel fuel. It also possesses special medicinal value and has attracted keen interests of researchers to explore its bioactivity. To extract the total triterpenoid saponins from the husk of X. sorbifolia (TSX) and investigate its effects on Alzheimer's disease (AD). TSX was prepared via modern extraction techniques. Its effects on two AD animal models, as well as the preliminary mechanism were investigated comprehensively. The behavioral experiments including Y maze test, Morris water maze test and passive avoidance test were performed to observe the learning and memory abilities of the animals. ELISA assays, transmission electron microscope observation and Western blotting were employed in mechanism study. TSX, the main composition of X. sorbifolia, accounted for 88.77% in the plant material. It could significantly increase the spontaneous alternation in Y maze test (F (6, 65)=3.209, Plearning and memory. The preliminary mechanism might associate with its protection effects against oxidative stress damage, cholinergic system deficiency and synaptic damage. TSX are perfectly suitable for AD patients as medicine or functional food, which would be a new candidate to treat AD. Copyright © 2016 Elsevier GmbH. All rights reserved.

  18. Ilexgenin A, a novel pentacyclic triterpenoid extracted from Aquifoliaceae shows reduction of LPS-induced peritonitis in mice.

    Science.gov (United States)

    Sun, Weidong; Liu, Chang; Zhang, Yaqi; Qiu, Xia; Zhang, Li; Zhao, Hongxia; Rong, Yi; Sun, Yun

    2017-02-15

    Ilexgenin A (IA) is a novel pentacyclic triterpenoid, which extracted from leaves of Ilex hainanensis Merr. In the present study, we aim to explore anti-inflammatory activity of IA on LPS-induced peritonitis and its underlying molecular mechanism. The results determined that IA was capable of suppressing peritonitis in mice induced by intraperitoneal (i.p.) injection of lipopolysaccaride (LPS). Furthermore, the results showed that IA dramatically inhibited levels of inflammatory cells infiltration in peritoneal cavity and serum in LPS-induced mice peritonitis model. Besides, IA could dramatically inhibit levels of inflammatory cytokines (IL-1β, IL-6 and TNF-α) in peritoneal cavity in LPS-induced mice peritonitis model. In vitro study, the results showed that IA inhibited production of IL-1β, IL-6 and TNF-α at transcriptional and translational levels in RAW 264.7 cells induced by LPS. Furthermore, IA could suppress the LPS-induced activation of Akt and downstream degradation and phosphorylation of kappa B-α (IκB-α). Moreover, IA could significantly inhibit ERK 1/2 phosphorylation in RAW 264.7 cells induced by LPS. These results were concurrent with molecular docking which revealed ERK1/2 inhibition. These results demonstrated that IA might as an anti-inflammatory agent candidate for inflammatory disease therapy. Copyright © 2017 Elsevier B.V. All rights reserved.

  19. Hepatoprotective Effects of Total Triterpenoids and Total Flavonoids from Vitis vinifera L against Immunological Liver Injury in Mice

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    Tao Liu

    2012-01-01

    Full Text Available Suosuo grape (the fruits of Vitis vinifera L has been used for prevention and treatment of liver diseases in Uighur folk medicine in China besides its edible value. In this study, the hepatoprotective effects of total triterpenoids (VTT and total flavonoids (VTF from Suosuo grape were evaluated in Bacille-Calmette-Guerin- (BCG- plus-lipopolysaccharide- (LPS- induced immunological liver injury (ILI in mice. Various dose groups (50, 150, and 300 mg/kg of VTT and VTF alleviated the degree of liver injury of ILI mice, effectively reduced the BCG/LPS-induced elevated liver index and spleen index, hepatic nitric oxide (NO, and malondialdehyde (MDA content, increased liver homogenate alanine aminotransferase (ALT and aspartate aminotransferase (AST levels, and restored hepatic superoxide dismutase (SOD activity in ILI mice. VTT and VTF also significantly inhibited intrahepatic expression of Th1 cytokines (IFN-γ and IL-2 in ILI mice and increased intrahepatic expression of Th2 cytokines (IL-4 and IL-10. Moreover, the increased Bax/Bcl-2 ratio was significantly downregulated by VTT and VTF in liver tissue of ILI mice. These results are comparable to those of biphenyl dicarboxylate (DDB, the reference hepatoprotective agent and suggest that VTT and VTF play a protective role against immunological liver injury, which may have important implications for our understanding of the immunoregulatory mechanisms of this plant.

  20. Camellianols A-G, Barrigenol-like Triterpenoids with PTP1B Inhibitory Effects from the Endangered Ornamental Plant Camellia crapnelliana.

    Science.gov (United States)

    Xiong, Juan; Wan, Jiang; Ding, Jie; Wang, Pei-Pei; Ma, Guang-Lei; Li, Jia; Hu, Jin-Feng

    2017-11-22

    Seven new naturally occurring barrigenol-like compounds, camellianols A-G (1-7), and 10 known triterpenoids were isolated from the twigs and leaves of the cultivated endangered ornamental plant Camellia crapnelliana. According to the ECD octant rule for saturated cyclohexanones, the absolute configurations of camellianols D (4) and E (5) were defined. The backbones of the remaining new isolates are assumed to have the same absolute configuration as compounds 4, 5, and harpullone (12). Compounds 2, 3, 9, 10, 13, and 16 exhibited inhibitory effects on the protein tyrosine phosphatase 1B (PTP1B) enzyme, with IC 50 values less than 10 μM.

  1. Triterpenoid Saponins from Anemone rivularis var. Flore-Minore and Their Anti-Proliferative Activity on HSC-T6 Cells.

    Science.gov (United States)

    Wang, Xiao-Yang; Gao, Hui; Xie, Xiao-Jie; Jurhiin, Jirimubatu; Zhang, Mu-Zi-He; Zhou, Yan-Ping; Liu, Rui; Ning, Meng; Han, Jin; Tang, Hai-Feng

    2018-02-23

    Five previously undescribed triterpenoid saponins ( 1 - 5 ), along with eight known ones ( 6 - 13 ), were isolated from the whole plants of Anemone rivularis var. flore-minore . Their structures were clarified by extensive spectroscopic data and chemical evidence. For the first time, the lupane-type saponins ( 3 and 12 ) were reported from the Anemone genus. The anti-proliferative activity of all isolated saponins was evaluated on hepatic stellate cells (HSC-T6). Saponins 12 and 13 , which possess more monosaccharides than the others, displayed potent anti-proliferative activity, with IC 50 values of 18.21 and 15.56 μM, respectively.

  2. Betulinic acid, a bioactive pentacyclic triterpenoid, inhibits skeletal-related events induced by breast cancer bone metastases and treatment

    Energy Technology Data Exchange (ETDEWEB)

    Park, Se Young; Kim, Hyun-Jeong; Kim, Ki Rim; Lee, Sun Kyoung; Lee, Chang Ki; Park, Kwang-Kyun, E-mail: biochelab@yuhs.ac; Chung, Won-Yoon, E-mail: wychung@yuhs.ac

    2014-03-01

    Many breast cancer patients experience bone metastases and suffer skeletal complications. The present study provides evidence on the protective and therapeutic potential of betulinic acid on cancer-associated bone diseases. Betulinic acid is a naturally occurring triterpenoid with the beneficial activity to limit the progression and severity of cancer, diabetes, cardiovascular diseases, atherosclerosis, and obesity. We first investigated its effect on breast cancer cells, osteoblastic cells, and osteoclasts in the vicious cycle of osteolytic bone metastasis. Betulinic acid reduced cell viability and the production of parathyroid hormone-related protein (PTHrP), a major osteolytic factor, in MDA-MB-231 human metastatic breast cancer cells stimulated with or without tumor growth factor-β. Betulinic acid blocked an increase in the receptor activator of nuclear factor-kappa B ligand (RANKL)/osteoprotegerin ratio by downregulating RANKL protein expression in PTHrP-treated human osteoblastic cells. In addition, betulinic acid inhibited RANKL-induced osteoclastogenesis in murine bone marrow macrophages and decreased the production of resorbed area in plates with a bone biomimetic synthetic surface by suppressing the secretion of matrix metalloproteinase (MMP)-2, MMP-9, and cathepsin K in RANKL-induced osteoclasts. Furthermore, oral administration of betulinic acid inhibited bone loss in mice intra-tibially inoculated with breast cancer cells and in ovariectomized mice causing estrogen deprivation, as supported by the restored bone morphometric parameters and serum bone turnover markers. Taken together, these findings suggest that betulinic acid may have the potential to prevent bone loss in patients with bone metastases and cancer treatment-induced estrogen deficiency. - Highlights: • Betulinic acid reduced PTHrP production in human metastatic breast cancer cells. • Betulinic acid blocked RANKL/OPG ratio in PTHrP-stimulated human osteoblastic cells. • Betulinic

  3. Betulinic acid, a bioactive pentacyclic triterpenoid, inhibits skeletal-related events induced by breast cancer bone metastases and treatment

    International Nuclear Information System (INIS)

    Park, Se Young; Kim, Hyun-Jeong; Kim, Ki Rim; Lee, Sun Kyoung; Lee, Chang Ki; Park, Kwang-Kyun; Chung, Won-Yoon

    2014-01-01

    Many breast cancer patients experience bone metastases and suffer skeletal complications. The present study provides evidence on the protective and therapeutic potential of betulinic acid on cancer-associated bone diseases. Betulinic acid is a naturally occurring triterpenoid with the beneficial activity to limit the progression and severity of cancer, diabetes, cardiovascular diseases, atherosclerosis, and obesity. We first investigated its effect on breast cancer cells, osteoblastic cells, and osteoclasts in the vicious cycle of osteolytic bone metastasis. Betulinic acid reduced cell viability and the production of parathyroid hormone-related protein (PTHrP), a major osteolytic factor, in MDA-MB-231 human metastatic breast cancer cells stimulated with or without tumor growth factor-β. Betulinic acid blocked an increase in the receptor activator of nuclear factor-kappa B ligand (RANKL)/osteoprotegerin ratio by downregulating RANKL protein expression in PTHrP-treated human osteoblastic cells. In addition, betulinic acid inhibited RANKL-induced osteoclastogenesis in murine bone marrow macrophages and decreased the production of resorbed area in plates with a bone biomimetic synthetic surface by suppressing the secretion of matrix metalloproteinase (MMP)-2, MMP-9, and cathepsin K in RANKL-induced osteoclasts. Furthermore, oral administration of betulinic acid inhibited bone loss in mice intra-tibially inoculated with breast cancer cells and in ovariectomized mice causing estrogen deprivation, as supported by the restored bone morphometric parameters and serum bone turnover markers. Taken together, these findings suggest that betulinic acid may have the potential to prevent bone loss in patients with bone metastases and cancer treatment-induced estrogen deficiency. - Highlights: • Betulinic acid reduced PTHrP production in human metastatic breast cancer cells. • Betulinic acid blocked RANKL/OPG ratio in PTHrP-stimulated human osteoblastic cells. • Betulinic

  4. Pentacyclic Triterpenoids Inhibit IKKβ Mediated Activation of NF-κB Pathway: In Silico and In Vitro Evidences.

    Directory of Open Access Journals (Sweden)

    Kalpesh R Patil

    Full Text Available Pentacyclic Triterpenoids (PTs and their analogues as well as derivatives are emerging as important drug leads for various diseases. They act through a variety of mechanisms and a majority of them inhibit the nuclear factor kappa-beta (NF-κB signaling pathway. In this study, we examined the effects of the naturally occurring PTs on IκB kinase-β (IKKβ, which has great scientific relevance in the NF-κB signaling pathway. On virtual screening, 109 PTs were screened through the PASS (prediction of activity spectra of substances software for prediction of NF-κB inhibitory activity followed by docking on the NEMO/IKKβ association complex (PDB: 3BRV and testing for compliance with the softened Lipinski's Rule of Five using Schrodinger (LLC, New York, USA. Out of the projected 45 druggable PTs, Corosolic Acid (CA, Asiatic Acid (AA and Ursolic Acid (UA were assayed for IKKβ kinase activity in the cell free medium. The UA exhibited a potent IKKβ inhibitory effect on the hotspot kinase assay with IC50 of 69 μM. Whereas, CA at 50 μM concentration markedly reduced the NF-κB luciferase activity and phospho-IKKβ protein expressions. The PTs tested, attenuated the expression of the NF-κB cascade proteins in the LPS-stimulated RAW 264.7 cells, prevented the phosphorylation of the IKKα/β and blocked the activation of the Interferon-gamma (IFN-γ. The results suggest that the IKKβ inhibition is the major mechanism of the PTs-induced NF-κB inhibition. PASS predictions along with in-silico docking against the NEMO/IKKβ can be successfully applied in the selection of the prospective NF-κB inhibitory downregulators of IKKβ phosphorylation.

  5. The First Pentacyclic Triterpenoid Gypsogenin Derivative Exhibiting Anti-ABL1 Kinase and Anti-chronic Myelogenous Leukemia Activities.

    Science.gov (United States)

    Ciftci, Halil Ibrahim; Ozturk, Safiye Emirdag; Ali, Taha F S; Radwan, Mohamed O; Tateishi, Hiroshi; Koga, Ryoko; Ocak, Zeynep; Can, Mustafa; Otsuka, Masami; Fujita, Mikako

    2018-04-01

    The discovery of the chimeric tyrosine kinase breakpoint cluster region kinase-Abelson kinase (BCR-ABL)-targeted drug imatinib conceptually changed the treatment of chronic myelogenous leukemia (CML). However, some CML patients show drug resistance to imatinib. To address this issue, some artificial heterocyclic compounds have been identified as BCR-ABL inhibitors. Here we examined whether plant-derived pentacyclic triterpenoid gypsogenin and/or their derivatives show inhibitory activity against BCR-ABL. Among the three derivatives, benzyl 3-hydroxy-23-oxoolean-12-en-28-oate (1c) was found to be the most effective anticancer agent on the CML cell line K562, with an IC 50 value of 9.3 µM. In contrast, the IC 50 against normal peripheral blood mononuclear cells was 276.0 µM, showing better selectivity than imatinib. Compound 1c had in vitro inhibitory activity against Abelson kinase 1 (ABL1) (IC 50 =8.7 µM), the kinase component of BCR-ABL. In addition, compound 1c showed a different inhibitory profile against eight kinases compared with imatinib. The interaction between ATP binding site of ABL and 1c was examined by molecular docking study, and the binding mode was different from imatinib and newer generation inhibitors. Furthermore, 1c suppressed signaling downstream of BCR-ABL. This study suggests the possibility that plant extracts may be a source for CML treatment and offer a strategy to overcome drug resistance to known BCR-ABL inhibitors.

  6. Antidiabetic activities of a cucurbitane‑type triterpenoid compound from Momordica charantia in alloxan‑induced diabetic mice.

    Science.gov (United States)

    Jiang, Bowen; Ji, Mingli; Liu, Wei; Chen, Lili; Cai, Zhiyu; Zhao, Yuqing; Bi, Xiuli

    2016-11-01

    Momordica charantia has been used to treat a variety of diseases, including inflammation, diabetes and cancer. A cucurbitane‑type triterpenoid [(19R,23E)‑5β, 19‑epoxy‑19‑methoxy‑cucurbita‑6,23,25‑trien‑3 β‑o‑l] previously isolated from M. charantia was demonstrated to possess significant cytotoxicity against cancer cells. The current study investigated the effects of this compound (referred to as compound K16) on diabetes using an alloxan‑induced diabetic mouse model. C57BL/6J mice were intraperitoneally injected with alloxan (10 mg/kg body weight), and those with blood glucose concentration higher than 10 mM were selected for further experiments. Diabetic C57BL/6J mice induced by alloxan were administered 0.9% saline solution, metformine (10 mg/kg body weight), or K16 (25 or 50 mg/kg body weight) by gavage for 4 weeks, followed by analysis of blood glucose level, glucose tolerance, serum lipid levels and organ indexes. The results demonstrated that compound K16 significantly reduced blood glucose (31‑48.6%) and blood lipids (13.5‑42.8%; triglycerides and cholesterol), while improving glucose tolerance compared with diabetic mice treated with saline solution, suggesting a positive improvement in glucose and lipid metabolism following K16 treatment. Furthermore, similarly to metformine, compound K16 markedly upregulated the expression of a number of insulin signaling pathway‑associated proteins, including insulin receptor, insulin receptor substrate 1, glycogen synthase kinase 3β, Akt serine/threonine kinase, and the transcript levels of glucose transporter type 4 and AMP‑activated protein kinase α1. The results of the current study demonstrated that compound K16 alleviated diabetic metabolic symptoms in alloxan‑induced diabetic mice, potentially by affecting genes and proteins involved in insulin metabolism signaling.

  7. Phenolic and triterpenoid composition and inhibition of α-amylase of pistachio kernels (Pistacia vera L.) as affected by rootstock and irrigation treatment.

    Science.gov (United States)

    Noguera-Artiaga, Luis; Pérez-López, David; Burgos-Hernández, Armando; Wojdyło, Aneta; Carbonell-Barrachina, Ángel A

    2018-09-30

    The current water scarcity forces farmers to adopt new irrigation strategies to save water without jeopardizing the fruit yield and quality. In this study, the influence of 3 regulated deficit irrigation (RDI) treatments and 3 rootstocks on the functional quality of pistachios were studied. The functional parameters studied included, polyphenols, triterpenoids, and inhibition of α-amylase. The results showed that P. terebinthus and P. atlantica rootstocks led to pistachio kernels with higher contents of polyphenols and triterpenoids (mainly betulinic acid with 111 and 102 µg g -1 , respectively) than pistachios obtained using P. integerrima rootstock (81 µg g -1 ). On the other hand, the use of moderate RDI (T1 treatment) increased the total content of polyphenols (∼10%), quercetin-O-galloyl-hexoside (∼15%), keampferol-3-O-glucoside (∼19%), and polymeric procyanidins (∼20%), as compared to the control trees, resulting in pistachios with a better functional profile, lower economic cost and with a lesser environmental impact. Copyright © 2018 Elsevier Ltd. All rights reserved.

  8. Supercritical Fluid Extraction of Eucalyptus globulus Bark—A Promising Approach for Triterpenoid Production

    Directory of Open Access Journals (Sweden)

    Carlos M. Silva

    2012-06-01

    Full Text Available Eucalyptus bark contains significant amounts of triterpenoids with demonstrated bioactivity, namely triterpenic acids and their acetyl derivatives (ursolic, betulinic, oleanolic, betulonic, 3-acetylursolic, and 3-acetyloleanolic acids. In this work, the supercritical fluid extraction (SFE of Eucalyptus globulus deciduous bark was carried out with pure and modified carbon dioxide to recover this fraction, and the results were compared with those obtained by Soxhlet extraction with dichloromethane. The effects of pressure (100–200 bar, co-solvent (ethanol content (0, 5 and 8% wt, and multistep operation were studied in order to evaluate the applicability of SFE for their selective and efficient production. The individual extraction curves of the main families of compounds were measured, and the extracts analyzed by GC-MS. Results pointed out the influence of pressure and the important role played by the co-solvent. Ethanol can be used with advantage, since its effect is more important than increasing pressure by several tens of bar. At 160 bar and 40 °C, the introduction of 8% (wt of ethanol greatly improves the yield of triterpenoids more than threefold.

  9. Simultaneous determination of flavonoids, isochlorogenic acids and triterpenoids in Ilex hainanensis Using high performance liquid chromatography coupled with diode array and evaporative light scattering detection.

    Science.gov (United States)

    Peng, Bo; Qiao, Chun-Feng; Zhao, Jing; Huang, Wei-Hua; Hu, De-Jun; Liu, Hua-Gang; Li, Shao-Ping

    2013-03-04

    A high performance liquid chromatography coupled with diode array and evaporative light scattering detection (HPLC-DAD-ELSD) method for simultaneous determination of eight major bioactive compounds including two flavonoids (rutin and eriodictyol-7-O-β-D-glucopyranoside), two isochlorogenic acids (isochlorogenic acid A and isochlorogenic acid C) and four triterpenoids (ilexhainanoside D, ilexsaponin A1, ilexgenin A and ursolic acid) in Ilex hainanensis has been developed for the first time. The 283 nm wavelength was chosen for determination of two flavonoids and two isochlorogenic acids. ELSD was applied to determine four triterpenoids. The analysis was performed on an Agilent Zorbax SB-C18 column (250 × 4.6 mm i.d., 5 µm) with gradient elution of 0.2% formic acid in water and acetonitrile. The method was validated for linearity, limit of detection, limit of quantification, precision, repeatability and accuracy. The proposed method has been successfully applied for simultaneous quantification of the analytes in four samples of Ilex hainanensis, which is helpful for quality control of this plant.

  10. Soyasaponin Bh, a Triterpene Saponin Containing a Unique Hemiacetal-Functional Five-Membered Ring from Glycine max (Soybeans)

    Science.gov (United States)

    Soybeans (Glycine max L. Merill) and soy-based food products are major dietary sources of saponins. An oleanane triterpenoid saponin, soyasaponin Bh (1) containing a unique five-membered ring with a hemiacetal functionality together with seven known saponins were isolated from soybeans. Their struct...

  11. Three further triterpenoid saponins from Gleditsia caspica fruits and protective effect of the total saponin fraction on cyclophosphamide-induced genotoxicity in mice.

    Science.gov (United States)

    Melek, Farouk R; Aly, Fawzia A; Kassem, Iman A A; Abo-Zeid, Mona A M; Farghaly, Ayman A; Hassan, Zeinab M

    2015-01-01

    Three triterpenoidal saponins were isolated from the saponin fraction derived from a Gleditsia caspica Desf. methanolic fruit extract. The isolated saponins were identified as gleditsiosides B, C, and Q based on spectral data. The saponin-containing fraction was evaluated in vivo for genotoxic and antigenotoxic activities. The fraction caused no DNA damage in Swiss albino male mice treated with a dose of 45 mg/kg body weight for 24 h, although it significantly inhibited the number of chromosomal aberrations induced by cyclophosphamide (CP) in bone marrow and germ cells when applied before or after CP administration. The inhibitory indices in chromosomal aberrations were 59% and 41% for bone marrow and 48% and 43% for germ cells, respectively. In addition, the saponin fraction was found to reduce the viability of the human tumor cell line MCF-7 in a dose-dependent manner with an extrapolated IC50 value in the range of 220 μg/mL.

  12. Inhibitors of HIV-1 maturation: Development of structure-activity relationship for C-28 amides based on C-3 benzoic acid-modified triterpenoids.

    Science.gov (United States)

    Swidorski, Jacob J; Liu, Zheng; Sit, Sing-Yuen; Chen, Jie; Chen, Yan; Sin, Ny; Venables, Brian L; Parker, Dawn D; Nowicka-Sans, Beata; Terry, Brian J; Protack, Tricia; Rahematpura, Sandhya; Hanumegowda, Umesh; Jenkins, Susan; Krystal, Mark; Dicker, Ira B; Meanwell, Nicholas A; Regueiro-Ren, Alicia

    2016-04-15

    We have recently reported on the discovery of a C-3 benzoic acid (1) as a suitable replacement for the dimethyl succinate side chain of bevirimat (2), an HIV-1 maturation inhibitor that reached Phase II clinical trials before being discontinued. Recent SAR studies aimed at improving the antiviral properties of 2 have shown that the benzoic acid moiety conferred topographical constraint to the pharmacophore and was associated with a lower shift in potency in the presence of human serum albumin. In this manuscript, we describe efforts to improve the polymorphic coverage of the C-3 benzoic acid chemotype through modifications at the C-28 position of the triterpenoid core. The dimethylaminoethyl amides 17 and 23 delivered improved potency toward bevirimat-resistant viruses while increasing C24 in rat oral PK studies. Copyright © 2016 Elsevier Ltd. All rights reserved.

  13. Friedelane-type triterpenoids as selective anti-inflammatory agents by regulation of differential signaling pathways in LPS-stimulated macrophages

    Energy Technology Data Exchange (ETDEWEB)

    Villar-Lorenzo, Andrea, E-mail: avillar@iib.uam.es [Instituto de Investigaciones Biomédicas Alberto Sols (IIBm) (CSIC/UAM), C/ Arturo Duperier 4, 28029 Madrid (Spain); Centro de Investigación Biomédica en Red de Diabetes y Enfermedades Metabólicas Asociadas (CIBERdem), ISCIII, 28029 Madrid (Spain); Ardiles, Alejandro E., E-mail: ale_csic@gmail.com [Instituto Universitario de Bio-Orgánica Antonio González, Departamento de Química Orgánica, Universidad de La Laguna, Avenida Astrofísico Francisco Sánchez 2, 38206 La Laguna, Tenerife (Spain); Facultad de Ciencias de la Salud, Universidad Arturo Prat, Casilla 121, Iquique 1110939 (Chile); Arroba, Ana I., E-mail: aarroba@iib.uam.es [Instituto de Investigaciones Biomédicas Alberto Sols (IIBm) (CSIC/UAM), C/ Arturo Duperier 4, 28029 Madrid (Spain); Centro de Investigación Biomédica en Red de Diabetes y Enfermedades Metabólicas Asociadas (CIBERdem), ISCIII, 28029 Madrid (Spain); Hernández-Jiménez, Enrique, E-mail: enheji@gmail.com [Tumor Immunology Laboratory (IdiPAZ), 28029 Madrid (Spain); Centro de Investigación Biomédica en Red de Enfermedades Respiratorias (CIBERres), ISCIII, 28029 Madrid (Spain); and others

    2016-12-15

    A series of 31 pentacyclic triterpenoids isolated from the root barks of Celastrus vulcanicola and Maytenus jelskii were tested for cytotoxicity and inhibitory activity against lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW 264.7 macrophages. Compounds 18 (C18) and 25 (C25) exhibited significant inhibition of LPS-induced NO release at 50 and 25 μM concentrations, respectively, and decreased mRNAs of pro-inflammatory cytokines. At the molecular level, C18 neither inhibited LPS-mediated phosphorylation of mitogen activated protein kinases (MAPKs) nor nuclear translocation of nuclear factor kappa beta (NFκB). Instead, C18 enhanced and prolonged nuclear translocation of nuclear factor-erythroid 2-related factor 2 (Nrf2) and increased the expression of its target genes including hemeoxigenase 1 (HO1). C25 efficiently inhibited LPS-mediated phosphorylation of JNK, p38 and ERK, without affecting NFκB or Nrf2 signaling pathways. Both compounds reduced LPS-mediated processing of caspase-1 and the cleavage of interleukin 1β (IL1β) proform, reflecting their ability to target the inflammasome. C25 also counteracted LPS effects on iNOS expression and pro-inflammatory cytokines mRNA levels in Bv-2 microglial cells. The anti-inflammatory effect of both compounds was also assessed in human macrophages. Our results suggest that triterpenoids C18 and C25 possess anti-inflammatory effects, which may be therapeutically relevant for diseases linked to inflammation. - Highlights: • Compounds 18 (C18) and 25 (C25) exert anti-inflammatory effects in macrophages. • C18 enhanced nuclear translocation of Nrf2 and increased HO1 expression. • C25 inhibited the phosphorylation of JNK, p38 and ERK, members of the MAPKs family. • C25 reduced LPS-mediated processing of caspase-1 and the cleavage of interleukin 1β. • C18 and C25 may be therapeutic agents for diseases linked to inflammation.

  14. Friedelane-type triterpenoids as selective anti-inflammatory agents by regulation of differential signaling pathways in LPS-stimulated macrophages

    International Nuclear Information System (INIS)

    Villar-Lorenzo, Andrea; Ardiles, Alejandro E.; Arroba, Ana I.; Hernández-Jiménez, Enrique

    2016-01-01

    A series of 31 pentacyclic triterpenoids isolated from the root barks of Celastrus vulcanicola and Maytenus jelskii were tested for cytotoxicity and inhibitory activity against lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW 264.7 macrophages. Compounds 18 (C18) and 25 (C25) exhibited significant inhibition of LPS-induced NO release at 50 and 25 μM concentrations, respectively, and decreased mRNAs of pro-inflammatory cytokines. At the molecular level, C18 neither inhibited LPS-mediated phosphorylation of mitogen activated protein kinases (MAPKs) nor nuclear translocation of nuclear factor kappa beta (NFκB). Instead, C18 enhanced and prolonged nuclear translocation of nuclear factor-erythroid 2-related factor 2 (Nrf2) and increased the expression of its target genes including hemeoxigenase 1 (HO1). C25 efficiently inhibited LPS-mediated phosphorylation of JNK, p38 and ERK, without affecting NFκB or Nrf2 signaling pathways. Both compounds reduced LPS-mediated processing of caspase-1 and the cleavage of interleukin 1β (IL1β) proform, reflecting their ability to target the inflammasome. C25 also counteracted LPS effects on iNOS expression and pro-inflammatory cytokines mRNA levels in Bv-2 microglial cells. The anti-inflammatory effect of both compounds was also assessed in human macrophages. Our results suggest that triterpenoids C18 and C25 possess anti-inflammatory effects, which may be therapeutically relevant for diseases linked to inflammation. - Highlights: • Compounds 18 (C18) and 25 (C25) exert anti-inflammatory effects in macrophages. • C18 enhanced nuclear translocation of Nrf2 and increased HO1 expression. • C25 inhibited the phosphorylation of JNK, p38 and ERK, members of the MAPKs family. • C25 reduced LPS-mediated processing of caspase-1 and the cleavage of interleukin 1β. • C18 and C25 may be therapeutic agents for diseases linked to inflammation.

  15. Quantitative determination of triterpenoids and formononetin in rhizomes of black cohosh (Actaea racemosa) and dietary supplements by using UPLC-UV/ELS detection and identification by UPLC-MS.

    Science.gov (United States)

    Avula, Bharathi; Wang, Yan-Hong; Smillie, Troy J; Khan, Ikhlas A

    2009-03-01

    A UPLC-UV/ELSD method has been developed for analysis of major triterpenoids and formononetin in ACTAEA RACEMOSA L. (family Ranunculaceae) samples. The best results were obtained with an Acquity UPLC BEH C18 (100 mmx2.1 mm, i. d., 1 microm) column system using gradient elution with a mobile phase consisting of water and acetonitrile:methanol (7:3) at a constant flow rate of 0.3 mL/min. Owing to their low UV absorption, the triterpene saponins were detected by evaporative light scattering. Within 5.5 minutes, three main triterpenoid glycosides [cimiracemoside A, 23- EPI-26-deoxyactein, and actein] and an isoflavonoid, formononetin, could be separated, with detection limits of 5, 5, 10, and 0.01 microg/mL, respectively. The method was successfully used to analyze different Actaea racemosa market products as well as to distinguish between two other ACTAEA species. There was a significant variability in the amounts of the selected triterpene glycosides for the products containing black cohosh and rhizomes of black cohosh. The isoflavone formononetin was not detected in the samples analyzed. LC-MS coupled with the electrospray ionization (ESI) interface method is described for the identification of formononetin and triterpenoid glycosides in plant samples and dietary supplements that claim to contain black cohosh and different species of Actaea.

  16. Simultaneous quantification of triterpenoid saponins in rat plasma by UHPLC-MS/MS and its application to a pharmacokinetic study after oral total saponin of Aralia elata leaves.

    Science.gov (United States)

    Sun, Yichun; Xue, Juan; Li, Baimei; Lin, Xiaoting; Wang, Zhibin; Jiang, Hai; Zhang, Hongwei; Wang, Qiuhong; Kuang, Haixue

    2016-11-01

    A rapid, sensitive, and reliable analytical ultra performance liquid chromatography with tandem mass spectrometry method was developed for the simultaneous determination of Aralia-saponin IV, 3-O-β-d-glucopyranosyl-(1→3)-β-d-glucopyranosyl-(1→3)-β-d-glucopyranosyl oleanolic acid 28-O-β-d-glucopyranoside, Aralia-saponin A and Aralia-saponin B after the oral administration of total saponin of Aralia elata leaves in rat plasma. Plasma samples were pretreated by protein precipitation with methanol. The analysis was performed on an ACQUITY UPLC HSS T3 column. The detection was performed on a triple quadrupole tandem mass spectrometer in multiple reaction monitoring mode using an electrospray ionization source with negative ionization mode. Under the experimental conditions, the calibration curves of four analytes had good linearity values (r > 0.991). The intra- and inter-day precision values of the four analytes were ≤ 11.6%, and the accuracy was between -6.2 and 4.2%.The extraction recoveries of four triterpenoid saponins were in the range of 84.06-91.66% (RSD saponins in rat plasma after oral administration of total saponin of Aralia elata leaves, which helps guiding clinical usage of Aralia elata leaves. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  17. [Effects of triterpenoid from Psidium guajava leaves ursolic acid on proliferation, differentiation of 3T3-L1 preadipocyte and insulin resistance].

    Science.gov (United States)

    Lin, Juan-Na; Kuang, Qiao-Ting; Ye, Kai-He; Ye, Chun-Ling; Huang, Yi; Zhang, Xiao-Qi; Ye, Wen-Cai

    2013-08-01

    To investigate the influences of triterpenoid from Psidium guajava Leaves (ursolic acid) on the proliferation, differentiation of 3T3-L1 preadipocyte, and its possible mechanism treat for insulin resistance. 3T3-L1 preadipocyte was cultured in vitro. After adding ursolic acid to the culture medium for 48h, the cell viability was tested by MTT assay. Induced for 6 days, the lipid accumulation of adipocyte was measured by Oil Red O staining. The insulin resistant cell model was established with Dexamethasone. Cellular glucose uptake was determined with GOD-POD assays and FFA concentration was determined at the time of 48h. Secreted adiponectin were measured by ELISA. The protein levels of PPARgamma and PTP1B in insulin resistant adipocyte were measured by Western Blotting. Compared with medium control group, 30, 100 micromol/L ursolic acid could increase its proliferation and differentiation significantly (P 0.05). Ursolic acid can improve the proliferation and differentiation of 3T3-L1 preadipocyte, enhance cellular glucose uptake, inhibit the production of FFA, promote the secretion of adiponectin insulin resistant adipocyte, its mechanism may be related to upregulating the expression of PPARgamma protein.

  18. Antiplasmodial, cytotoxic activities and characterization of a new naturally occurring quinone methide pentacyclic triterpenoid derivative isolated from Salacia leptoclada Tul. (Celastraceae) originated from Madagascar.

    Science.gov (United States)

    Ruphin, Fatiany Pierre; Baholy, Robijaona; Emmanue, Andrianarivo; Amelie, Raharisololalao; Martin, Marie-Therese; Koto-te-Nyiwa, Ngbolua

    2013-10-01

    To validate scientifically the traditional use of Salacia leptoclada Tul. (Celastraceae) (S. leptoclada) and to isolate and elucidate the structure of the biologically active compound. Bioassay-guided fractionation of the acetonic extract of the stem barks of S. leptoclada was carried out by a combination of chromatography technique and biological experiments in viro using Plasmodium falciparum and P388 leukemia cell lines as models. The structure of the biologically active pure compound was elucidated by 1D and 2D NMR spectroscopy and mass spectrometry. Biological screening of S. leptoclada extracts resulted in the isolation of a pentacyclic triterpenic quinone methide. The pure compound exhibited both in vitro a cytotoxic effect on murine P388 leukemia cells with IC50 value of (0.041±0.020) μg/mL and an antiplasmodial activity against the chloroquine-resistant strain FC29 of Plasmodium falciparum with an IC50 value of (0.052±0.030) μg/mL. Despite this interesting anti-malarial property of the lead compound, the therapeutic index was weak (0.788). In the best of our knowledge, the quinone methide pentacyclic triterpenoid derivative compound is reported for the first time in S. leptoclada. The results suggest that furthers studies involving antineoplastic activity is needed for the development of this lead compound as anticancer drug. Copyright © 2013 Asian Pacific Tropical Biomedical Magazine. Published by Elsevier B.V. All rights reserved.

  19. Rapid Determination of Two Triterpenoid Acids in Chaenomelis Fructus Using Supercritical Fluid Extraction On-line Coupled with Supercritical Fluid Chromatography.

    Science.gov (United States)

    Zhang, Xiaotian; Ji, Feng; Li, Yueqi; He, Tian; Han, Ya; Wang, Daidong; Lin, Zongtao; Chen, Shizhong

    2018-01-01

    In this study, an on-line supercritical fluid extraction (SFE) and supercritical fluid chromatography (SFC) method was developed for the rapid determination of oleanoic acid and ursolic acid in Chaenomelis Fructus. After optimization of the conditions, the two triterpenoid acids was obtained by SFE using 20% methanol as a modifier at 35°C in 8 min. They were resolved on a Shim-pack UC-X Diol column (4.6 × 150 mm, 3 μm) in 14 min (0 - 10 min, 5 - 10%; 10 - 14 min, 10% methanol in CO 2 ) with a backpressure of 15 MPa at 40°C. The on-line SFE-SFC method could be completed within 40 min (10.79 mg/g dry plant, R s = 2.36), while the ultrasound-assisted extraction and HPLC method required at least 90 min (3.55 mg/g dry plant, R s = 1.92). This on-line SFE-SFC method is powerful to simplify the pre-processing and quantitative analysis of natural products.

  20. A novel monocyclic triterpenoid and a norsesquaterpenol from the aerial parts of Suaeda monoica Forssk. ex J.F. Gmel with cell proliferative potential

    Directory of Open Access Journals (Sweden)

    Mansour S. Al-Said

    2017-11-01

    Full Text Available Suaeda monoica Forssk. ex J.F. Gmel (Chenopodiaceae, a mangrove herb, is distributed in tropical Africa, Arabian Peninsula, India, Pakistan, Palestine and Jordan. The plant parts are used to treat sore throat, hepatitis, wounds, rheumatism, paralysis, asthma, snakebites, skin disease and ulcer. Two new phytoconstituents characterized as 13,17-octahydropentalene-4,4,10,23-tetramethyl-17,21-diisopropyl-tetradecahydrocyclo-[a]-phenanthrene-(14, 20(23, 21(30-trien-5α-ol (SMC-3 and [1,4,4-trimethyl-cyclopent-1(5-enyl]-9,10,17,21-tetramethyl-9α-ol-16α (17α-epoxy heptadecan-6,10-dione (SMC-4 belong to the class norsesquaterpenol and monocyclic triterpenoid, respectively, along with two known compounds 3-epi-lupeol (SMC-1 and 4-cyclopentylpyrocatechol (SMC-2 have been isolated from the ethanol extract of aerial parts of S. monoica using normal and reverse phase column as well as planar chromatography. The spectroscopic studies including 1D, 2D NMR (DEPT, COSY, HMBC and HSQC aided by EIMS mass and IR spectra were used to establish their structures. All the four compounds were tested for cytotoxicity on cultured HepG2 cells and for cell proliferation activities. The results revealed no cytotoxicity even at highest (6.25–50 μg/ml dose of all the four compounds. The compound SMC-1 showed prominent cell proliferative activity as compared to other SMC compounds.

  1. Hypoglycemic and hypolipidemic effects of triterpenoid-enriched Jamun (Eugenia jambolana Lam.) fruit extract in streptozotocin-induced type 1 diabetic mice.

    Science.gov (United States)

    Xu, Jialin; Liu, Tingting; Li, Yuanyuan; Yuan, Chunhui; Ma, Hang; Seeram, Navindra P; Liu, Feifei; Mu, Yu; Huang, Xueshi; Li, Liya

    2018-06-20

    The edible berries of Eugenia jambolana Lam. (known as Jamun) are consumed in various parts of the world. Our previous studies revealed that a triterpenoid-enriched Jamun fruit extract (TJFE) showed beneficial effects on glucose homeostasis in non-diabetic mice. Herein, the anti-diabetic effects of TJFE (100 mg kg-1 by oral gavage for ten days) were evaluated in streptozotocin (STZ)-induced type 1 diabetic mice. TJFE significantly attenuated STZ-induced hyperglycemia and glucose intolerance, suppressed the abnormal elevation of hepatic gluconeogenesis, and improved dyslipidemia in the mice. Histopathology and mechanism-based studies revealed that TJFE preserved the architecture and function of pancreatic islets, attenuated insulin secretion deficiency, enhanced insulin/Akt signaling transduction, reduced lipogenic gene expression, and prevented the abnormal activation of Erk MAPK in the liver tissues of the STZ-induced diabetic mice. The current study adds to previously published data supporting the potential beneficial effects of this edible fruit on diabetes management.

  2. Induction of Highly Curved Structures in Relation to Membrane Permeabilization and Budding by the Triterpenoid Saponins, α- and δ-Hederin

    Science.gov (United States)

    Lorent, Joseph; Le Duff, Cécile S.; Quetin-Leclercq, Joelle; Mingeot-Leclercq, Marie-Paule

    2013-01-01

    The interactions of triterpenoid monodesmosidic saponins, α-hederin and δ-hederin, with lipid membranes are involved in their permeabilizing effect. Unfortunately, the interactions of these saponins with lipid membranes are largely unknown, as are the roles of cholesterol or the branched sugar moieties (two for α-hederin and one for δ-hederin) on the aglycone backbone, hederagenin. The differences in sugar moieties are responsible for differences in the molecular shape of the saponins and the effects on membrane curvature that should be the most positive for α-hederin in a transbilayer direction. In large unilamellar vesicles and monocyte cells, we showed that membrane permeabilization was dependent on the presence of membrane cholesterol and saponin sugar chains, being largest for α-hederin and smallest for hederagenin. In the presence of cholesterol, α-hederin induced the formation of nonbilayer phases with a higher rate of Brownian tumbling or lateral diffusion. A reduction of Laurdan's generalized polarization in relation to change in order of the polar heads of phospholipids was observed. Using giant unilamellar vesicles, we visualized the formation of wrinkled borders, the decrease in liposome size, budding, and the formation of macroscopic pores. All these processes are highly dependent on the sugars linked to the aglycone, with α-hederin showing a greater ability to induce pore formation and δ-hederin being more efficient in inducing budding. Hederagenin induced intravesicular budding but no pore formation. Based on these results, a curvature-driven permeabilization mechanism dependent on the interaction between saponin and sterols and on the molecular shape of the saponin and its ability to induce local spontaneous curvature is proposed. PMID:23530040

  3. Triterpenoid herbal saponins enhance beneficial bacteria, decrease sulfate-reducing bacteria, modulate inflammatory intestinal microenvironment and exert cancer preventive effects in ApcMin/+ mice

    Science.gov (United States)

    Chen, Lei; Brar, Manreetpal S.; Leung, Frederick C. C.; Hsiao, W. L. Wendy

    2016-01-01

    Saponins derived from medicinal plants have raised considerable interest for their preventive roles in various diseases. Here, we investigated the impacts of triterpenoid saponins isolated from Gynostemma pentaphyllum (GpS) on gut microbiome, mucosal environment, and the preventive effect on tumor growth. Six-week old ApcMin/+ mice and their wild-type littermates were fed either with vehicle or GpS daily for the duration of 8 weeks. The fecal microbiome was analyzed by enterobacterial repetitive intergenic consensus (ERIC)-PCR and 16S rRNA gene pyrosequencing. Study showed that GpS treatment significantly reduced the number of intestinal polyps in a preventive mode. More importantly, GpS feeding strikingly reduced the sulfate-reducing bacteria lineage, which are known to produce hydrogen sulfide and contribute to damage the intestinal epithelium or even promote cancer progression. Meanwhile, GpS also boosted the beneficial microbes. In the gut barrier of the ApcMin/+ mice, GpS treatment increased Paneth and goblet cells, up-regulated E-cadherin and down-regulated N-cadherin. In addition, GpS decreased the pro-oncogenic β-catenin, p-Src and the p-STAT3. Furthermore, GpS might also improve the inflamed gut epithelium of the ApcMin/+ mice by upregulating the anti-inflammatory cytokine IL-4, while downregulating pro-inflammatory cytokines TNF-β, IL-1β and IL-18. Intriguingly, GpS markedly stimulated M2 and suppressed M1 macrophage markers, indicating that GpS altered mucosal cytokine profile in favor of the M1 to M2 macrophages switching, facilitating intestinal tissue repair. In conclusion, GpS might reverse the host's inflammatory phenotype by increasing beneficial bacteria, decreasing sulfate-reducing bacteria, and alleviating intestinal inflammatory gut environment, which might contribute to its cancer preventive effects. PMID:27121311

  4. 21-O-Angeloyltheasapogenol E3, a Novel Triterpenoid Saponin from the Seeds of Tea Plants, Inhibits Macrophage-Mediated Inflammatory Responses in a NF-κB-Dependent Manner

    Directory of Open Access Journals (Sweden)

    Woo Seok Yang

    2014-01-01

    Full Text Available 21-O-Angeloyltheasapogenol E3 (ATS-E3 is a triterpenoid saponin recently isolated from the seeds of the tea tree Camellia sinensis (L. O. Kuntze. ATS-E3 has several beneficial properties including anti-inflammatory, antidiabetic, antiatherosclerotic, and anticancer effects. Unlike other phenolic compounds isolated from tea plants, there are no studies reporting the pharmacological action of ATS-E3. In this study, we therefore aimed to explore the cellular and molecular inhibitory activities of ATS-E3 in macrophage-mediated inflammatory responses. ATS-E3 remarkably diminished cellular responses of macrophages such as FITC-dextran-induced phagocytic uptake, sodium nitroprusside- (SNP- induced radical generation, and LPS-induced nitric oxide (NO production. Analysis of its molecular activity showed that this compound significantly suppressed the expression of inducible NO synthase (iNOS, nuclear translocation of nuclear factor- (NF- κB subunits (p50 and p65, phosphorylation of inhibitor of κB kinase (IKK, and the enzyme activity of AKT1. Taken together, the novel triterpenoid saponin compound ATS-E3 contributes to the beneficial effects of tea plants by exerting anti-inflammatory and antioxidative activities in an AKT/IKK/NF-κB-dependent manner.

  5. A new diterpenoid glucoside and two new diterpenoids from the fruit of Vitex agnus-castus.

    Science.gov (United States)

    Ono, Masateru; Eguchi, Keisuke; Konoshita, Masatarou; Furusawa, Chisato; Sakamoto, Junich; Yasuda, Shin; Ikeda, Tsuyoshi; Okawa, Masafumi; Kinjo, Junei; Yoshimitsu, Hitoshi; Nohara, Toshihiro

    2011-01-01

    A new labdane-type diterpenoid glucoside and two new labdane-type diterpenoids were isolated from the fruit (chasteberry) of Vitex agnus-castus L. (Verbenaceae) along with 14 known compounds comprising seven labdane-type diterpenoids, one halimane-type diterpenoid, two oleanane-type triterpenoids, two ursane-type triterpenoids, one aromadendrane-type sesquiterpenoid, and one flavonoid. Their structures were characterized on the basis of spectroscopic data as well as chemical evidence. Furthermore, the antioxidative activities of the flavonoid were evaluated using five different analyses.

  6. NF-κB and JNK mediated apoptosis and G0/G1 arrest of HeLa cells induced by rubiarbonol G, an arborinane-type triterpenoid from Rubia yunnanensis.

    Science.gov (United States)

    Zeng, Guang-Zhi; Wang, Zhe; Zhao, Li-Mei; Fan, Jun-Ting; Tan, Ning-Hua

    2018-06-28

    Rubia yunnanensis is a medicinal plant mainly grown in Yunnan province in Southwest China, and its root named "Xiaohongshen" has been used as a herb in Yunnan for the treatment of cancers. Three major types of chemical components, Rubiaceae-type cyclopeptides, quinones, and triterpenoids, were identified from R. yunnanensis, in which some of compounds including rubiarbonol G (RG), a unique arboriane-type triterpenoid, showed cytotoxicity on cancer cells. But the cytotoxic mechanism of RG has not been reported. To investigate the cytotoxic mechanism of RG on cancer cells. RG was evaluated its cytotoxicity on 7 cancer cell lines by the SRB assay, and detected the effect on apoptosis and cell cycle arrest by Annexin V-FITC/PI apoptosis assay and DNA contents analysis. The expression and activity of apoptosis and cell cycle related proteins were also investigated by western blot and caspase activity assay. Furthermore, the effect of RG on NF-κB signaling was also tested by luciferase assay, western blot, and immunofluorescence staining. RG showed potent cytotoxicity on 7 human cancer cell lines, whose activity was attributed to apoptosis induction and G 0 /G 1 arrest in HeLa cells. Results from the mechanism study showed that RG promoted the activation of ERK1/2 and JNK pathway in MAPK family, which in turn increased the expression of p53, thereby triggering the G 0 /G 1 arrest through p53/p21/cyclin D1 signaling. Moreover, RG-mediated JNK activation down-regulated the expression of the anti-apoptotic protein Bcl-2, which caused the release of cytochrome c to the cytosol and activated the cleavage of caspase cascade and poly(ADP-ribose) polymerase, thereby inducing apoptosis in HeLa cells. In addition, RG was also found to inhibit the activation of NF-κB signaling by down-regulating the expression and attenuating the translocation to nucleus of NF-κB p65, by which the down-stream p53, cyclin D1, Bcl-2, and caspases were regulated, thereby triggering apoptosis and G

  7. Simultaneous determination of triterpenoid saponins in dog plasma by a validated UPLC-MS/MS and its application to a pharmacokinetic study after administration of total saponin of licorice.

    Science.gov (United States)

    Tao, Weiwei; Duan, Jinao; Guo, Jianming; Li, Jianping; Tang, Yuping; Liu, Pei; Yang, Nianyun

    2013-03-05

    A rapid and sensitive ultra performance liquid chromatography-tandem mass spectrometry method was developed for simultaneous determination of eight constituents, uralsaponin C, uralsaponin F, 22β-acetoxyl-glycyrrhizin, 24-hydroxy-licorice-saponin E2, licorice-saponin G2, licorice-saponin E2, glycyrrhizin, and licorice-saponin J2, from total saponin of licorice (TSL) in dog plasma. Ardisiacrispin A was used as the internal standard (IS). The separation was performed on Thermo Syncronic C₁₈ column (100 mm × 2.1 mm, 1.7 μm) at a flow rate of 0.4 mL min⁻¹, and acetonitrile/methanol (3:1, v/v)-0.1% formic acid was used as mobile phase. The detection was performed on a triple quadrupole tandem mass spectrometer by multiple reaction monitoring (MRM) via electrospray ionization (ESI) source with negative ionization mode. All calibration curves had good linearity (r>0.991) over the concentration range from 2.03-405 ng mL⁻¹ to 2.63-2625 ng mL⁻¹ for all components. The intra- and inter-day precision was within 15% and the accuracy ranged from -14.08% to 13.8%. The method was successfully applied to pharmacokinetic study of eight triterpenoid saponins in dog plasma after oral administration of TSL. Crown Copyright © 2012. Published by Elsevier B.V. All rights reserved.

  8. Protection against 2-chloroethyl ethyl sulfide (CEES) - induced cytotoxicity in human keratinocytes by an inducer of the glutathione detoxification pathway

    International Nuclear Information System (INIS)

    Abel, Erika L.; Bubel, Jennifer D.; Simper, Melissa S.; Powell, Leslie; McClellan, S. Alex; Andreeff, Michael; MacLeod, Michael C.; DiGiovanni, John

    2011-01-01

    Sulfur mustard (SM or mustard gas) was first used as a chemical warfare agent almost 100 years ago. Due to its toxic effects on the eyes, lungs, and skin, and the relative ease with which it may be synthesized, mustard gas remains a potential chemical threat to the present day. SM exposed skin develops fluid filled bullae resulting from potent cytotoxicity of cells lining the basement membrane of the epidermis. Currently, there are no antidotes for SM exposure; therefore, chemopreventive measures for first responders following an SM attack are needed. Glutathione (GSH) is known to have a protective effect against SM toxicity, and detoxification of SM is believed to occur, in part, via GSH conjugation. Therefore, we screened 6 potential chemopreventive agents for ability to induce GSH synthesis and protect cultured human keratinocytes against the SM analog, 2-chloroethyl ethyl sulfide (CEES). Using NCTC2544 human keratinocytes, we found that both sulforaphane and methyl-2-cyano-3,12-dioxooleana-1,9-dien-28-oate (CDDO-Me) stimulated nuclear localization of Nrf2 and induced expression of the GSH synthesis gene, GCLM. Additionally, we found that treatment with CDDO-Me elevated reduced GSH content of NCTC2544 cells and preserved their viability by ∼ 3-fold following exposure to CEES. Our data also suggested that CDDO-Me may act additively with 2,6-dithiopurine (DTP), a nucleophilic scavenging agent, to increase the viability of keratinocytes exposed to CEES. These results suggest that CDDO-Me is a promising chemopreventive agent for SM toxicity in the skin. - Highlights: → CDDO-Me treatment increased intracellular GSH in human keratinocytes. → CDDO-Me increased cell viability following exposure to the half-mustard, CEES. → The cytoprotective effect of CDDO-Me was likely due to scavenging with endogenous GSH.

  9. The novel triterpenoid RTA 408 protects human retinal pigment epithelial cells against H2O2-induced cell injury via NF-E2-related factor 2 (Nrf2 activation

    Directory of Open Access Journals (Sweden)

    Xiaobin Liu

    2016-08-01

    Full Text Available Oxidative stress-induced retinal pigment epithelial (RPE cell damage is an important factor in the pathogenesis of age-related macular degeneration (AMD. Previous studies have shown that RTA 408, a synthetic triterpenoid compound, potently activates Nrf2. This study aimed to investigate the protective effects of RTA 408 in cultured RPE cells during oxidative stress and to determine the effects of RTA 408 on Nrf2 and its downstream target genes. Primary human RPE cells were pretreated with RTA 408 and then incubated in 200 μM H2O2 for 6 h. Cell viability was measured with the WST-8 assay. Apoptosis was quantitatively measured by annexin V/propidium iodide (PI double staining and Hoechst 33342 fluorescent staining. Reduced (GSH and oxidized glutathione (GSSG were measured using colorimetric assays. Nrf2 activation and its downstream effects on phase II enzymes were examined by Western blot. Treatment of RPE cells with nanomolar ranges (10 and 100 nM of RTA 408 markedly attenuated H2O2-induced viability loss and apoptosis. RTA 408 pretreatment significantly protected cells from oxidative stress-induced GSH loss, GSSG formation and decreased ROS production. RTA 408 activated Nrf2 and increased the expression of its downstream genes, such as HO-1, NQO1, SOD2, catalase, Grx1, and Trx1. Consequently, the enzyme activities of NQO1, Grx1, and Trx1 were fully protected by RTA 408 pretreatment under oxidative stress. Moreover, knockdown of Nrf2 by siRNA significantly reduced the cytoprotective effects of RTA 408. In conclusion, our data suggest that RTA 408 protect primary human RPE cells from oxidative stress-induced damage by activating Nrf2 and its downstream genes.

  10. Preparation of new 18alpha-oleanane alcohols: synthesis, characterization, and cytotoxic activity

    Czech Academy of Sciences Publication Activity Database

    Kvasnica, Miroslav; Rudovská, I.; Hajduch, M.; Šarek, J.

    2010-01-01

    Roč. 141, č. 2 (2010), s. 233-244 ISSN 0026-9247 R&D Projects: GA AV ČR KAN200200651 Grant - others:GA ČR(CZ) GP203/05/P025; GA ČR(CZ) GA305/09/1216 Institutional research plan: CEZ:AV0Z40550506 Keywords : reduction * hydride * ketone * configuration * cytotoxicity Subject RIV: CC - Organic Chemistry Impact factor: 1.356, year: 2010

  11. Fatty acid synthase inhibitors isolated from Punica granatum L

    Energy Technology Data Exchange (ETDEWEB)

    Jiang, He-Zhong [School of Life Science and Engineering, Southwest Jiaotong University, Chengdu, (China); Ma, Qing-Yun; Liang, Wen-Juan; Huang, Sheng-Zhuo; Dai, Hao-Fu; Wang, Peng-Cheng; Zhao, You-Xing, E-mail: zhaoyx1011@163.com [Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou (China); Fan, Hui-Jin; Ma, Xiao-Feng, E-mail: maxiaofeng@gucas.ac.cn [College of Life Sciences, Graduate University of Chinese Academy of Sciences, Beijing (China)

    2012-05-15

    The aim of this work is the isolation of fatty acid synthase (FAS) inhibitors from the ethyl acetate extracts of fruit peels of Punica granatum L. Bioassay-guided chemical investigation of the fruit peels resulted in the isolation of seventeen compounds mainly including triterpenoids and phenolic compounds, from which one new oleanane-type triterpene (punicaone) along with fourteen known compounds were isolated for the first time from this plant. Seven isolates were evaluated for inhibitory activities of FAS and two compounds showed to be active. Particularly, flavogallonic acid exhibited strong FAS inhibitory activity with IC{sub 50} value of 10.3 {mu}mol L{sup -1}. (author)

  12. Fatty acid synthase inhibitors isolated from Punica granatum L

    International Nuclear Information System (INIS)

    Jiang, He-Zhong; Ma, Qing-Yun; Liang, Wen-Juan; Huang, Sheng-Zhuo; Dai, Hao-Fu; Wang, Peng-Cheng; Zhao, You-Xing; Fan, Hui-Jin; Ma, Xiao-Feng

    2012-01-01

    The aim of this work is the isolation of fatty acid synthase (FAS) inhibitors from the ethyl acetate extracts of fruit peels of Punica granatum L. Bioassay-guided chemical investigation of the fruit peels resulted in the isolation of seventeen compounds mainly including triterpenoids and phenolic compounds, from which one new oleanane-type triterpene (punicaone) along with fourteen known compounds were isolated for the first time from this plant. Seven isolates were evaluated for inhibitory activities of FAS and two compounds showed to be active. Particularly, flavogallonic acid exhibited strong FAS inhibitory activity with IC 50 value of 10.3 μmol L -1 . (author)

  13. New biofunctional effects of the flower buds of Camellia sinensis and its bioactive acylated oleanane-type triterpene oligoglycosides.

    Science.gov (United States)

    Matsuda, Hisashi; Nakamura, Seikou; Morikawa, Toshio; Muraoka, Osamu; Yoshikawa, Masayuki

    2016-10-01

    We review the biofunctional effects of the flower buds of Camellia sinensis and C. sinensis var. assamica, such as antihyperlipidemic, antihyperglycemic, antiobesity, and gastroprotective effects in vivo, and antiallergic, pancreatic lipase inhibitory, and amyloid β (Aβ) aggregation inhibitory activities in vitro. Although the biofunctional effects of tea leaves have been extensively studied, less attention has been given to those of the flowers and seeds of the tea plant. Our studies focused on the saponin constituents of the extracts of the flower buds of C. sinensis cultivated in Japan and China, and C. sinensis var. assamica cultivated in India, and we review their beneficial biofunctions for health promotion.

  14. Phytochemical Analysis of Pfaffia glomerata Inflorescences by LC-ESI-MS/MS

    Directory of Open Access Journals (Sweden)

    Daniele F. Felipe

    2014-09-01

    Full Text Available Pfaffia glomerata contains high levels of β-ecdysone, which has shown a range of beneficial pharmacological effects. The present study demonstrated that inflorescences of P. glomerata contain other important bioactive compounds in addition to β-ecdysone. The identification of compounds from inflorescences using liquid chromatography coupled with electrospray ionization tandem mass spectrometry (LC-ESI-MS/MS was performed for the first time. The eight compounds identified were β-ecdysone, flavonoid glycosides such as quercetin-3-O-glucoside, kaempferol-3-O-glucoside and kaempferol-3-O-(6-p-coumaroyl-glucoside, oleanane-type triterpenoid saponins such as ginsenoside Ro and chikusetsusaponin IV, in addition to oleanonic acid and gluconic acid. This study provided information on the phytochemicals contained in P. glomerata inflorescences revealing the potential application of this plant part as raw material for the phytotherapeutic and cosmetic industries.

  15. Dammarane-type triterpenes from the Brazilian medicinal plant Cordia multispicata.

    Science.gov (United States)

    Kuroyanagi, Masanori; Kawahara, Nobuo; Sekita, Setsuko; Satake, Motoyoshi; Hayashi, Tatsuo; Takase, Yoichi; Masuda, Kazuo

    2003-10-01

    From the Brazilian medicinal plant Carucaá (Cordia multispicata), oleanane- and ursane-type triterpenoids were previously reported as anti-androgenic constituents of the plant. In this study, purification of the polar elements of the EtOAc-soluble fraction of the plant revealed nine novel dammarane-type triterpenes, named cordianols A-I (1-9) along with the known compound cordialin A (10). The structures of these new compounds were elucidated by means of spectral methods including HRFABMS, (1)H NMR, (13)C NMR, and 2D NMR (HMQC, HMBC, NOESY). Absolute configuration at C-23 of compound 7 was determined by an excitone chirality method. Some of these new compounds revealed a hemiketal structure on the A ring and a hydroxylated or epoxidated 20(22)-(E)-ene side chain and showed weak anti-androgenic activity.

  16. Clionasterol, a Triterpenoid from the Kenyan Marine Green ...

    African Journals Online (AJOL)

    EMAIL FREE FULL TEXT EMAIL FREE FULL TEXT · DOWNLOAD FULL TEXT DOWNLOAD FULL TEXT · http://dx.doi.org/10.4314/wiojms.v2i2.28436 · Creative Commons License This work is licensed under a Creative Commons Attribution 3.0 License. AJOL African Journals Online. HOW TO USE AJOL... for Researchers ...

  17. Biflavones and triterpenoids isolated from Ouratea castaneifolia (DC. Engl., Ochnaceae

    Directory of Open Access Journals (Sweden)

    Luís Adriano S. do Nascimento

    Full Text Available This paper presents the chemical investigation of the leaves and stems of Ouratea castaneifolia (DC. Engl.. There are no chemical or pharmacological studies with this species. Classic phytochemical investigation of the organic extracts together with high pressure liquid chromatography (HPLC procedures lead to the identification of seventeen metabolites: seven triterpenes (friedelin, 3β-friedelinol, α-amyrin, β-amyrin, lupeol, germanicol and taraxerol, four steroids (sitosterol, stigmasterol and the glycosides sitosteryl 3-O-β-D-glucopyranoside and stigmasteryl 3-O-β-D-glucopyranoside, one isoflavone (5,7,4'-trimethoxyisoflavone, one flavone (5,4'-dihydroxy-7,3',5'-trimethoxyflavone and four biflavones (amenthoflavone, 7,7"-O-dimethylamenthoflavone, heveaflavone and tetramethylamenthoflavone. The structures of the compounds were established by the analysis of ¹H, 13C NMR spectra including bidimensional techniques. The classes of the identified metabolites are in agreement with previous studies of the Ouratea genus.

  18. Cytotoxic triterpenoids from the mushroom Clavulina cinerea (Bull) J ...

    African Journals Online (AJOL)

    The NCI 60 human cancer cell line panel was used to evaluate the ... also used as antioxidant with ascorbic acid as the main ingredient and are ..... fruit of rabbiteye blueberry (Vaccinium ashei). Food Sci. Technol. Res., 10(1):. 56-59. Osono T.

  19. Triterpenoidal saponins: bioactive secondary metabolites from Zygophyllum coccineum L

    Science.gov (United States)

    Phytochemical investigation of the aerial parts of Zygophyllum coccineum L., led to the isolation of nine ursane-type triterpene saponins (1-9) including one new: zygophylloside S (1), together with known flavonoid glycoside (10), and sterol glycoside (11). The isolated compounds were tested for ant...

  20. Triterpenoid saponins from Lippia alba (Mill.) N. E. Brown

    International Nuclear Information System (INIS)

    Farias, Mareni R.; Pertile, Roberto; Correa, Melissa M.; Schenkel, Eloir P.; Almeida, Maria Tereza R. de; Palermo, Jorge A.

    2010-01-01

    Two saponins were isolated from the leaves of Lippia alba. Their structures were established using one- and two-dimensional NMR spectroscopy and mass spectrometry. These new compounds were elucidated as 3-O-β-D-glucopyranosyl-28-O-(α-L-rhamnopyranosyl-(1→3)-beta-D-xylopyranosyl -(1→4)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl)-16α, 23-dihydroxy-olean -12-en-28-oic acid, named as Lippiasaponin I (2) and as 3-O-β-D-glucopyranosyl-28-O-(α-L-rhamnopyranosyl-(1→3)-β-D-xylopyranosyl- (1→4)-α-L-rhamnopyranosyl-(1→3)-α-Larabinopyranosyl)-16α,23-dihydroxy-olean -12-en-28-oic acid, named Lippiasaponin II (3). (author)

  1. Triterpenoids From the Leaves of Olax mannii Oliv. * MISule, HS

    African Journals Online (AJOL)

    2. A.A. Ambi. 1Department of Pharmaceutical and Medicinal Chemistry, Faculty of Pharmaceutical Sciences,. Ahmadu Bello University, Zaria-Nigeria. 2Department of Pharmacognosy, Faculty of Pharmaceutical Sciences,. Ahmadu Bello University, Zaria-Nigeria. [*Corresponding Author, E-mail: ibrasule@gmail.com]. 193.

  2. Triterpenoid saponins from Lippia alba (Mill.) N. E. Brown

    Energy Technology Data Exchange (ETDEWEB)

    Farias, Mareni R.; Pertile, Roberto; Correa, Melissa M.; Schenkel, Eloir P., E-mail: marenif@yahoo.com.b [Universidade Federal de Santa Catarina (UFSC), Florianopolis, SC (Brazil). Dept. de Ciencias Farmaceuticas. Programa de Pos-graduacao em Farmacia; Almeida, Maria Tereza R. de; Palermo, Jorge A. [Universidad de Buenos Aires (Argentina). Facultad de Ciencias Exactas y Naturales. Dept. de Quimica Organica

    2010-07-01

    Two saponins were isolated from the leaves of Lippia alba. Their structures were established using one- and two-dimensional NMR spectroscopy and mass spectrometry. These new compounds were elucidated as 3-O-beta-D-glucopyranosyl-28-O-(alpha-L-rhamnopyranosyl-(1->3)-beta-D-xylopyranosyl -(1->4)-alpha-L-rhamnopyranosyl-(1->2)-alpha-L-arabinopyranosyl)-16alpha, 23-dihydroxy-olean -12-en-28-oic acid, named as Lippiasaponin I (2) and as 3-O-beta-D-glucopyranosyl-28-O-(alpha-L-rhamnopyranosyl-(1->3)-beta-D-xylopyranosyl- (1->4)-alpha-L-rhamnopyranosyl-(1->3)-alpha-Larabinopyranosyl)-16alpha,23-dihydroxy-olean -12-en-28-oic acid, named Lippiasaponin II (3). (author)

  3. A new bioactive ursane-type triterpenoid from Croton ...

    Indian Academy of Sciences (India)

    blance of the leaves and flower cymes to that of Tulsi, this plant is often called Ban Tulsi locally. C. bon- plandianum was reported to have many medicinal uses including the repellent property against the insects,2–5 mosquito, A. aegypti.6 Local people in the remote area of West Bengal, India are using its root against snake.

  4. Triterpenoidal Saponins: Bioactive Secondary Metabolites from Zygophyllum coccineum

    Science.gov (United States)

    2011-01-22

    Merfort, Freiburg, Germany Kurt Schmidt, Graz, Austria Thomas Simmet, Ulm, Germany Hermann Stuppner, Innsbruck, Austria Yang-Chang Wu, Taichung, Taiwan ...hyperinsulinemic effects of some Egyptian herbs used for treatment of diabetes mellitus (Type II) in rats. Egypt J Pharm Sci 1995; 36: 331–341 5 Gibbons S

  5. Cytotoxic Triterpenoids from the Stalks of Microtropis triflora.

    Science.gov (United States)

    Zhang, Xiao-Wei; Wang, Kui-Wu; Zhou, Man-Qing

    2017-07-01

    Bioassay-guided phytochemical investigation of the stalks of Microtropis triflora Merr. & F.L. Freeman led to the isolation of ten triterpenes 1 - 10, including one novel compound 3,24-epoxy-2α,24-dihydroxyfriedelan-29-oic acid (1). Their chemical structures were identified on the basis of spectroscopic analysis, including HR-ESI mass spectrometry, 1D- and 2D-NMR ( 1 H, 13 C, 1 H, 1 H-COSY, HSQC, HMBC, and NOESY), and by comparison with the data reported. The cytotoxicities of compounds 1 - 10 against a panel of cultured human tumor cell lines (Bcap37, SMMC7721, HeLa, CNE) were evaluated. The new compound 1 showed moderate anti-tumor activities with IC 50 values of 39.22, 29.24, 23.28, and 68.81 μm/ml, respectively. These results might be helpful for explaining the use of M. triflora in traditional medicine. Triterpenes are characteristic of Microtropis genus and could be useful as potential chemotaxonomic markers. © 2017 Wiley-VHCA AG, Zurich, Switzerland.

  6. Cytotoxicity of Triterpenes from Green Walnut Husks of Juglans mandshurica Maxim in HepG-2 Cancer Cells.

    Science.gov (United States)

    Zhou, Yuanyuan; Yang, Bingyou; Liu, Zhaoxi; Jiang, Yanqiu; Liu, Yuxin; Fu, Lei; Wang, Xiaoli; Kuang, Haixue

    2015-10-22

    Among the classes of identified natural products, triterpenoids, one of the largest families, have been studied extensively for their diverse structures and variety of biological activities, including antitumor effects. In the present study, a phytochemical study of the green walnut husks of Juglans mandshurica Maxim led to the isolation of a new dammarane triterpene, 12β, 20(R), 24(R)-trihydroxydammar-25-en-3-one (6), together with sixteen known compounds, chiefly from chloroform and ethyl acetate extracts. According to their structural characteristics, these compounds were divided into dammarane-type, oleanane- and ursane-type. Dammarane-type triterpenoids were isolated for the first time from the Juglans genus. As part of our continuing search for biologically active compounds from this plant, all of these compounds were also evaluated for their cytotoxic activities against the growth of human cancer cells lines HepG-2 by the MTT assay. The results were shown that 20(S)-protopanaxadiol, 2α,3β,23-trihydroxyolean-12-en-28-oic acid and 2α,3β,23-trihydroxyurs-12-en-28-oic acid exhibited better cytotoxicity in vitro with IC50 values of 10.32±1.13, 16.13±3.83, 15.97±2.47 μM, respectively. Preliminary structure-activity relationships for these compounds were discussed.

  7. In-Vitro Activity of Saponins of Bauhinia Purpurea Madhuca Longifolia Celastrus Paniculatus and Semecarpus Anacardium on Selected Oral Pathogens

    Directory of Open Access Journals (Sweden)

    K. S. Jyothi

    2012-01-01

    Full Text Available Objective: Dental caries, periodontitis and other mucosal diseases are caused by a complex community of microorganisms. This study aimed to investigate the antimicrobial properties of saponins of four important oil yielding medicinal plant extracts on selected oral pathogens that are involved in such diseases.Materials and Methods: Saponins were extracted from Bauhinia purpurea, Madhuca longifolia, Celastrus paniculatus and Semecarpus anacardium and purified. Antimicrobial properties of these saponins against Streptococcus mutans, Streptococcus mitis, Streptococcus salivarius, Staphylococcus aureus and Lactobacillus acidophilus were determined using well diffusion method. The minimum inhibitory concentration (MIC was determined as the lowest concentration of saponins inhibiting bacterial growth after 14 h of incubation at 37°C. The bactericidal activity was evaluated using the viable cell count method.Results: The minimum inhibitory concentration (MIC and minimum bactericidal concentration (MBC of Madhuca longifolia saponin on Streptococcus mutans MTCC 890, Streptococcus mitis and Staphylococcus aureus was 18.3 ± 0.15/34.4 ± 0.24 µg/ml, 19.0 ± 0.05/32.2 ± 0.0 µg/ml and 21.2 ± 0.35/39.0 ± 0.30 µg/ml, respectively and Bauhinia purpurea saponin on Streptococcus mutans MTCC 890, Staphylococcus aureus and Lactobacillus acidophilus was 26.4 ± 0.20/43.0 ± 0.40 µg/ml, 29.0 ± 0.30/39.6 ± 0.12 µg/ml and 20.2 ± 0.05/36.8 ± 0.23 µg/ml, respectively.Conclusion: The strong antimicrobial activity of Madhuca longifolia and Bauhinia purpurea may be due to the presence of complex triterpenoid saponins, oleanane type triterpenoid glycosides or atypical pentacyclic triterpenoid saponin. Hence, these extracted saponins may be used in food and oral products to prevent and control oral diseases.

  8. In-Vitro Activity of Saponins of Bauhinia Purpurea, Madhuca Longifolia, Celastrus Paniculatus and Semecarpus Anacardium on Selected Oral Pathogens

    Science.gov (United States)

    Jyothi, K. S.; Seshagiri, M.

    2012-01-01

    Objective: Dental caries, periodontitis and other mucosal diseases are caused by a complex community of microorganisms. This study aimed to investigate the antimicrobial properties of saponins of four important oil yielding medicinal plant extracts on selected oral pathogens that are involved in such diseases. Materials and Methods: Saponins were extracted from Bauhinia purpurea, Madhuca longifolia, Celastrus paniculatus and Semecarpus anacardium and purified. Antimicrobial properties of these saponins against Streptococcus mutans, Streptococcus mitis, Streptococcus salivarius, Staphylococcus aureus and Lactobacillus acidophilus were determined using well diffusion method. The minimum inhibitory concentration (MIC) was determined as the lowest concentration of saponins inhibiting bacterial growth after 14 h of incubation at 37°C. The bactericidal activity was evaluated using the viable cell count method. Results: The minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) of Madhuca longifolia saponin on Streptococcus mutans MTCC 890, Streptococcus mitis and Staphylococcus aureus was 18.3 ± 0.15/34.4 ± 0.24 μg/ml, 19.0 ± 0.05/32.2 ± 0.0 μg/ml and 21.2 ± 0.35/39.0 ± 0.30 μg/ml, respectively and Bauhinia purpurea saponin on Streptococcus mutans MTCC 890, Staphylococcus aureus and Lactobacillus acidophilus was 26.4 ± 0.20/43.0 ± 0.40 μg/ml, 29.0 ± 0.30/39.6 ± 0.12 μg/ml and 20.2 ± 0.05/36.8 ± 0.23 μg/ml, respectively. Conclusion: The strong antimicrobial activity of Madhuca longifolia and Bauhinia purpurea may be due to the presence of complex triterpenoid saponins, oleanane type triterpenoid glycosides or atypical pentacyclic triterpenoid saponin. Hence, these extracted saponins may be used in food and oral products to prevent and control oral diseases. PMID:23323183

  9. Medicinal Flowers. XXXII. Structures of oleanane-type triterpene saponins, perennisosides VIII, IX, X, XI, and XII, from the flowers of Bellis perennis.

    Science.gov (United States)

    Morikawa, Toshio; Li, Xuezheng; Nishida, Eriko; Nakamura, Seikou; Ninomiya, Kiyofumi; Matsuda, Hisashi; Hamao, Makoto; Muraoka, Osamu; Hayakawa, Takao; Yoshikawa, Masayuki

    2011-01-01

    Five new triterpene saponins perennisosides VIII (1), IX (2), X (3), XI (4), and XII (5) were isolated from the MeOH-eluated fraction of the methanolic extract from the flowers of Bellis perennis. The MeOH-eluted fraction of the methanolic extract from the flowers of B. perennis was found to inhibit gastric emptying in olive oil-loaded mice at a dose of 200 mg/kg, per os (p.o.). The stereostructures of 1-5 were elucidated on the basis of chemical and spectroscopic evidence.

  10. Isolation and characterization of an oxidosqualene cyclase gene encoding a β-amyrin synthase involved in Polygala tenuifolia Willd. saponin biosynthesis.

    Science.gov (United States)

    Jin, Mei Lan; Lee, Dae Young; Um, Yurry; Lee, Jeong Hoon; Park, Chun Geun; Jetter, Reinhard; Kim, Ok Tae

    2014-03-01

    Expression of PtBS (Polygala tenuifolia β-amyrin synthase) led to the production of β-amyrin as sole product. Polygala tenuifolia Willdenow is a rich source of triterpene saponins, onjisaponins and polygalasaponins, used as herbal medicine to treat phlegms and for detumescence in traditional Asian healing. The Polygala saponins share the oleanane backbone structure and are, therefore, likely synthesized via β-amyrin as a common precursor. We hypothesized that, in analogy to diverse other plant species, this central intermediate should be formed by a β-amyrin synthase catalyzing the complex cyclization of oxidosqualene. This member of the oxidosqualene cyclase (OSC) family of enzymes is thus defining an important branch point between primary and secondary metabolisms, and playing a crucial role in the control of oleanane-type triterpene saponin biosynthesis. From P. tenuifolia roots, we isolated an OSC cDNA containing a reading frame of 2,289 bp nucleotides. The predicted protein of 763 amino acids (molecular weight 87.353 kDa) showed particularly high amino acid sequence identities to known β-amyrin synthases (85-87 %) and was, therefore, named PtBS. Expression of PtBS in the triterpenoid synthase-deficient yeast mutant GIL77 led to the production of β-amyrin as sole product. qRT-PCR analysis of various P. tenuifolia organs showed that PtBS transcript levels were highest in the roots, consistent with onjisaponin accumulation patterns. Therefore, we conclude that PtBS is the β-amyrin synthase enzyme catalyzing the first committed step in the biosynthesis of onjisaponins and polygalasaponins in P. tenuifolia.

  11. Design and synthesis of new hybrids from 2-cyano-3,12-dioxooleana- 9-dien-28-oic acid and O2-(2,4-dinitrophenyl) diazeniumdiolate for intervention of drug-resistant lung cancer.

    Science.gov (United States)

    Kang, Fenghua; Ai, Yong; Zhang, Yihua; Huang, Zhangjian

    2018-04-10

    To search for new drugs for intervention of drug-resistant lung cancer, a series of hybrids 4-15 from 2-cyano-3,12-dioxooleana-9-dien-28-oic acid (CDDO) and O 2 -(2,4-dinitrophenyl) diazeniumdiolate were designed, synthesized and biologically evaluated. The most active compound 7 produced relatively high levels of nitric oxide (NO) and reactive oxygen species (ROS) in drug-resistant lung cancer A549/Taxol cells which over-express glutathione S-transferase π (GSTπ), and significantly inhibited the cells' proliferation (IC 50  = 0.349 ± 0.051 μM), superior to the positive controls CDDO-Me, JS-K and Taxol. The inhibitory activity of 7 could be attenuated by an NO scavenger, ROS scavenger or GSTπ inhibitor. In addition, 7 suppressed the Lon protease expression as well as induced cell apoptosis and cycle arrest in A549/Taxol cells more strongly than CDDO-Me or JS-K. Together, our findings suggest that 7 may be worth studying further for intervention of drug-resistant lung cancer. Copyright © 2018 Elsevier Masson SAS. All rights reserved.

  12. Optimization of solid-phase extraction and liquid chromatography-tandem mass spectrometry for simultaneous determination of capilliposide B and its active metabolite in rat urine and feces: Overcoming nonspecific binding.

    Science.gov (United States)

    Cheng, Zhongzhe; Zhou, Xing; Li, Wenyi; Hu, Bingying; Zhang, Yang; Xu, Yong; Zhang, Lin; Jiang, Hongliang

    2016-11-30

    Capilliposide B, a novel oleanane triterpenoid saponin isolated from Lysimachia capillipes Hemsl, showed significant anti-tumor activities in recent studies. To characterize the excretion of Capilliposide B, a reliable liquid chromatography-tandem mass spectrometry (LC-MS/MS) method was developed and validated for simultaneous determination of Capilliposide B and its active metabolite, Capilliposide A in rat urine and feces. Sample preparation using a solid-phase extraction procedure was optimized by acidification of samples at various degrees, providing extensive sample clean-up with a high extraction recovery. In addition, rat urinary samples were pretreated with CHAPS, an anti-adsorptive agent, for overcoming nonspecific analytes adsorption during sample storage and process. The method validation was conducted over the curve range of 10.0-5000ng/ml for both analytes. The intra- and inter-day precision and accuracy of the QC samples showed ≤11.0% RSD and -10.4-12.8% relative error. The method was successfully applied to an excretion study of Capilliposide B following intravenous administration. Copyright © 2016 Elsevier B.V. All rights reserved.

  13. Chemical constituents and biological activities of Dianthus elegans var. elegans.

    Science.gov (United States)

    Mutlu, Kiymet; Sarikahya, Nazli Boke; Nalbantsoy, Ayse; Kirmizigul, Suheyla

    2018-06-01

    Chemical investigation of the aerial parts of Dianthus elegans var. elegans afforded two previously undescribed saponins, named dianosides M-N (1-2), together with four oleanane-type triterpenoid glycosides (3-6). Their structures were elucidated as 3-O-α-L-arabinofuranosyl-16α-hydroxyolean-12-ene-23α, 28β-dioic acid (1) and 3-O-α-L-arabinofuranosyl-(1 → 3)-β-D-glucopyranosyl 16α-hydroxyolean-12-ene-23α-oic acid, 28-O-β-D-glucopyranosyl-(1 → 6)-β-D-glycosyl ester (2) by chemical and extensive spectroscopic methods including IR, 1D, 2D NMR and HRESIMS. Both of the saponins were evaluated for their cytotoxicities against HEK-293, A-549 and HeLa human cancer cells using the MTT method. All compounds showed no substantial cytotoxic activity against tested cell lines. However, dianosides M-N and the n-butanol fraction exhibited considerable haemolysis in human erythrocyte cells. The immunomodulatory properties of dianosides M-N were also evaluated in activated whole blood cells by PMA plus ionomycin. Dianosides M-N increased IL-1β concentration significantly whereas the n-butanol fraction slightly augmented IL-1β secretion. All compounds did not change IL-2 and IFN-γ levels considerably.

  14. Identification of new natural sweet compounds in wine using centrifugal partition chromatography-gustatometry and Fourier transform mass spectrometry.

    Science.gov (United States)

    Marchal, Axel; Waffo-Téguo, Pierre; Génin, Eric; Mérillon, Jean-Michel; Dubourdieu, Denis

    2011-12-15

    Sweetness contributes notably to the taste-balance of dry wines and increases during oak-barrel aging owing to the release of natural sweeteners from wood. The search for such taste-active molecules, which are sometimes present at very low concentrations in wine or other complex matrixes, requires both reliable purification tools and powerful identification techniques. Here, we report the development of an original inductive method using centrifugal partition chromatography (CPC) and sensorial analysis. This method, called CPC-gustatometry, was implemented to isolate a sweet fraction with only four compounds from a complex oak wood extract. The recently developed Fourier transform mass spectrometry (FT-MS, Orbitrap analyzer) was used jointly with two-dimensional nuclear magnetic resonance (2D (1)H and (13)C NMR) to obtain the structural elucidation of the purified compounds. The tandem mass spectrometry (MS/MS) spectra obtained with resonant and nonresonant fragmentation modes were compared, thus providing complementary information about the molecular structure. Two oleanane-type triterpenoids substituted with galloyl and glucosyl moieties were identified, one of which exhibits sweet properties. We term these compounds which have never been reported, Quercotriterpenoside I and II.

  15. The effect of aromatization on the isotopic compositions of hydrocarbons during early diagenesis

    Science.gov (United States)

    Freeman, K. H.; Boreham, C. J.; Summons, R. E.; Hayes, J. M.

    1994-01-01

    Polycyclic aromatic hydrocarbons with varying degrees of aromatization were isolated from the Eocene Messel Shale (Rheingraben, Germany). The high abundances of these compounds and their structural resemblances to cyclic triterpenoid lipids are consistent with derivation from microbial rather than thermal processes. Compounds structurally related to oleanane contain from five to nine double bonds; those within a series of aromatized hopanoids contain from three to nine. All are products of diagenetic reactions that remove hydrogen or methyl groups, and, in several cases, break carbon-carbon bonds to open rings. Aromatized products are on average depleted in 13C relative to possible precursors by l.2% (range: l.5% enrichment to 4% depletion, n = 9). The dependence of 13C content on the number of double bonds is not, however, statistically significant and it must be concluded that there is no strong evidence for isotopic fractionation accompanying diagenetic aromatization. Isotopic differences between series (structures related to ursane, des-A-ursane, des-A-lupane, des-A-arborane, and possibly, des-A-gammacerane are present) are much greater, indicating that 13C contents are controlled primarily by source effects. Fractionations due to chromatographic isotope effects during HPLC ranged from 0.1 to 2.8%.

  16. Triterpenoid Saponin Biosynthesis in the non-model Crucifer Plant Barbares Vulgaris

    DEFF Research Database (Denmark)

    Erthmann, Pernille Østerbye

    ratios were identified In vivo results suggest the rate limiting step for saponin biosynthesis in B. vulgaris to be the expression levels of 2,3-oxidosqualene cyclase. To support these findings, an in vivo knock-out of the OSC via CRISPER/Cas was desired. To achieve this, stable transformants of B...

  17. AntiMtb activity of triterpenoid-rich fractions from Spondias mombin L.

    African Journals Online (AJOL)

    STORAGESEVER

    2009-05-04

    May 4, 2009 ... stomachache, biliousness, urethritis, cystitis and eye and throat inflammation. The juice of crushed leaves and the powder of dried leaves are used as poultices on wounds and inflammations. The gum is employed as an expec- torant and to expel tapeworms. Our antimtb screening of plant products from ...

  18. In vivo induction of phase II detoxifying enzymes, glutathione transferase and quinone reductase by citrus triterpenoids

    Directory of Open Access Journals (Sweden)

    Ahmad Hassan

    2010-09-01

    Full Text Available Abstract Background Several cell culture and animal studies demonstrated that citrus bioactive compounds have protective effects against certain types of cancer. Among several classes of citrus bioactive compounds, limonoids were reported to prevent different types of cancer. Furthermore, the structures of citrus limonoids were reported to influence the activity of phase II detoxifying enzymes. The purpose of the study was to evaluate how variations in the structures of citrus limonoids (namely nomilin, deacetyl nomilin, and isoobacunoic acid and a mixture of limonoids would influence phase II enzyme activity in excised tissues from a mouse model. Methods In the current study, defatted sour orange seed powder was extracted with ethyl acetate and subjected to silica gel chromatography. The HPLC, NMR and mass spectra were used to elucidate the purity and structure of compounds. Female A/J mice were treated with three limonoids and a mixture in order to evaluate their effect on phase II enzymes in four different tissues. Assays for glutathione S-transferase and NAD(PH: quinone reductase (QR were used to evaluate induction of phase II enzymatic activity. Results The highest induction of GST against 1-chloro-2,4-dinitrobenzene (CDNB was observed in stomach (whole, 58% by nomilin, followed by 25% isoobacunoic acid and 19% deacetyl nomilin. Deacetyl nomilin in intestine (small as well as liver significantly reduced GST activity against CDNB. Additionally isoobacunoic acid and the limonoid mixture in liver demonstrated a significant reduction of GST activity against CDNB. Nomilin significantly induced GST activity against 4-nitroquinoline 1-oxide (4NQO, intestine (280% and stomach (75% while deacetyl nomilin showed significant induction only in intestine (73%. Induction of GST activity was also observed in intestine (93% and stomach (45% treated with the limonoid mixture. Finally, a significant induction of NAD(PH: quinone reductase (QR activity was observed by the limonoid mixture in stomach (200%. In addition, the deacetyl nomilin treatment group displayed an increase in QR activity in liver (183% and intestine (22%. Conclusion The results of the present study suggests that, dietary intake of citrus limonoids may provide a protective effect against the onset of various cancers by inducing the activity of certain phase II detoxifying enzymes in specific organs.

  19. Targeting Inflammatory Pathways by Triterpenoids for Prevention and Treatment of Cancer

    Directory of Open Access Journals (Sweden)

    Bharat B. Aggarwal

    2010-10-01

    Full Text Available Traditional medicine and diet has served mankind through the ages for prevention and treatment of most chronic diseases. Mounting evidence suggests that chronic inflammation mediates most chronic diseases, including cancer. More than other transcription factors, nuclear factor-kappaB (NF-κB and STAT3 have emerged as major regulators of inflammation, cellular transformation, and tumor cell survival, proliferation, invasion, angiogenesis, and metastasis. Thus, agents that can inhibit NF-κB and STAT3 activation pathways have the potential to both prevent and treat cancer. In this review, we examine the potential of one group of compounds called triterpenes, derived from traditional medicine and diet for their ability to suppress inflammatory pathways linked to tumorigenesis. These triterpenes include avicins, betulinic acid, boswellic acid, celastrol, diosgenin, madecassic acid, maslinic acid, momordin, saikosaponins, platycodon, pristimerin, ursolic acid, and withanolide. This review thus supports the famous adage of Hippocrates, “Let food be thy medicine and medicine be thy food”.

  20. Ursolic Acid—A Pentacyclic Triterpenoid with a Wide Spectrum of Pharmacological Activities

    Directory of Open Access Journals (Sweden)

    Łukasz Woźniak

    2015-11-01

    Full Text Available Ursolic acid (UA is a natural terpene compound exhibiting many pharmaceutical properties. In this review the current state of knowledge about the health-promoting properties of this widespread, biologically active compound, as well as information about its occurrence and biosynthesis are presented. Particular attention has been paid to the application of ursolic acid as an anti-cancer agent; it is worth noticing that clinical tests suggesting the possibility of practical use of UA have already been conducted. Amongst other pharmacological properties of UA one can mention protective effect on lungs, kidneys, liver and brain, anti-inflammatory properties, anabolic effects on skeletal muscles and the ability to suppress bone density loss leading to osteoporosis. Ursolic acid also exhibits anti-microbial features against numerous strains of bacteria, HIV and HCV viruses and Plasmodium protozoa causing malaria.

  1. Inhibitory Effect of Triterpenoids from Panax ginseng on Coagulation Factor X

    Directory of Open Access Journals (Sweden)

    Lingxin Xiong

    2017-04-01

    Full Text Available Enzymes involved in the coagulation process have received great attention as potential targets for the development of oral anti-coagulants. Among these enzymes, coagulation factor Xa (FXa has remained the center of attention in the last decade. In this study, 16 ginsenosides and two sapogenins were isolated, identified and quantified. To determine the inhibitory potential on FXa, the chromogenic substrates method was used. The assay suggested that compounds 5, 13 and 18 were mainly responsible for the anti-coagulant effect. Furthermore, these three compounds also possessed high thrombin selectivity in the thrombin inhibition assay. Furthermore, Glide XP from Schrödinger was employed for molecular docking to clarify the interaction between the bioactive compounds and FXa. Therefore, the chemical and biological results indicate that compounds 5 (ginsenoside Rg2, 13 (ginsenoside Rg3 and 18 (protopanaxtriol, PPT are potential natural inhibitors against FXa.

  2. The Sg-1 Glycosyltransferase Locus Regulates Structural Diversity of Triterpenoid Saponins of Soybean[W][OA

    Science.gov (United States)

    Sayama, Takashi; Ono, Eiichiro; Takagi, Kyoko; Takada, Yoshitake; Horikawa, Manabu; Nakamoto, Yumi; Hirose, Aya; Sasama, Hiroko; Ohashi, Mihoko; Hasegawa, Hisakazu; Terakawa, Teruhiko; Kikuchi, Akio; Kato, Shin; Tatsuzaki, Nana; Tsukamoto, Chigen; Ishimoto, Masao

    2012-01-01

    Triterpene saponins are a diverse group of biologically functional products in plants. Saponins usually are glycosylated, which gives rise to a wide diversity of structures and functions. In the group A saponins of soybean (Glycine max), differences in the terminal sugar species located on the C-22 sugar chain of an aglycone core, soyasapogenol A, were observed to be under genetic control. Further genetic analyses and mapping revealed that the structural diversity of glycosylation was determined by multiple alleles of a single locus, Sg-1, and led to identification of a UDP-sugar–dependent glycosyltransferase gene (Glyma07g38460). Although their sequences are highly similar and both glycosylate the nonacetylated saponin A0-αg, the Sg-1a allele encodes the xylosyltransferase UGT73F4, whereas Sg-1b encodes the glucosyltransferase UGT73F2. Homology models and site-directed mutagenesis analyses showed that Ser-138 in Sg-1a and Gly-138 in Sg-1b proteins are crucial residues for their respective sugar donor specificities. Transgenic complementation tests followed by recombinant enzyme assays in vitro demonstrated that sg-10 is a loss-of-function allele of Sg-1. Considering that the terminal sugar species in the group A saponins are responsible for the strong bitterness and astringent aftertastes of soybean seeds, our findings herein provide useful tools to improve commercial properties of soybean products. PMID:22611180

  3. Pharmacokinetic studies of active triterpenoid saponins and the total secondary saponin from Anemone raddeana Regel.

    Science.gov (United States)

    Zhang, Dandan; Lei, Tianli; Lv, Chongning; Zhao, Huimin; Xu, Haiyan; Lu, Jincai

    2017-02-15

    The rhizome of Anemone raddeana Regel, a Traditional Chinese Medicine (TCM) which has a robust history treating rheumatism and neuralgia. The total secondary saponin (TSS) from it has demonstrated antitumor activity. In this study, a rapid and validated LC-MS/MS method was developed to simultaneously determine the active compounds (Hederacolchiside A1 and Eleutheroside K). Analytes were separated on a reverse-phase C18 column with acetonitrile-water (5mmol/L ammonium acetate) as the mobile phase. This assay showed acceptable linearity (r>0.99) over the concentration range 5-1000 nmol/L for two analytes. The intra- and inter-day precision was within 8.06% and accuracy was ranged from -3.16% to 3.34% for two analytes. The mean extraction recoveries of analytes and IS from rat plasma were all more than 76.0%. Under the developed analytical conditions, the obtained values of main pharmacokinetic parameters (C max and AUC 0-t ) indicated that the pure compounds were more efficient than the TSS extract in Hederacolchiside A1 and Eleutheroside K absorption. In addition, pharmacokinetic studies of two individual compounds demonstrated their poor oral absorption in rat ( a F%, 0.019-1.521). In the study of absorption and transportation of Hederacolchiside A1 and Eleutheroside K in Caco-2 cell monolayer model, the uptake permeability was in 10 -6 cm/sec range suggesting poor absorption, which confirmed the previous pharmacokinetic profiles in vivo. Interestingly, the uptake ratio of them declined significantly when treated with phloridzin (SGLT1 inhibitor). It indicated that the absorption of Hederacolchiside A1 in intestine was mainly through positive transport and SGLT1 might participate in its active absorption. Copyright © 2017 Elsevier B.V. All rights reserved.

  4. Anti-tumor activity of triterpenoid-rich extract from bamboo shavings ...

    African Journals Online (AJOL)

    GREGORY

    2010-09-20

    Sep 20, 2010 ... temperature at 280°C. The column temperature was held at 100°C for 2 min and then ... 10% freshly inactivated fetal calf serum (FCS) and antibiotics. The ... dissolved in DMSO in advance and then in the culture medium with.

  5. Relationship between triterpenoid anticancer drug resistance, autophagy, and caspase-1 in adult T-cell leukemia

    Directory of Open Access Journals (Sweden)

    Tsukasa Nakanishi

    2016-05-01

    Full Text Available We previously reported that the inflammasome inhibitor cucurbitacin D (CuD induces apoptosis in human leukemia cell lines. Here, we investigated the effects of CuD and a B-cell lymphoma extra-large (Bcl-xL inhibitor on autophagy in peripheral blood lymphocytes (PBL isolated from adult T-cell leukemia (ATL patients. CuD induced PBL cell death in patients but not in healthy donors. This effect was not significantly inhibited by treatment with rapamycin or 3-methyladenine (3-MA. The Bcl-xL inhibitor Z36 induced death in primary cells from ATL patients including that induced by CuD treatment, effects that were partly inhibited by 3-MA. Similarly, cell death induced by the steroid prednisolone was enhanced in the presence of Z36. A western blot analysis revealed that Z36 also promoted CuD-induced poly(ADP ribose polymerase cleavage. Interestingly, the effects of CuD and Z36 were attenuated in primary ATL patient cells obtained upon recurrence after umbilical cord blood transplantation, as compared to those obtained before chemotherapy. Furthermore, cells from this patient expressed a high level of caspase-1, and treatment with caspase-1 inhibitor-enhanced CuD-induced cell death. Taken together, these results suggest that rescue from resistance to steroid drugs can enhance chemotherapy, and that caspase-1 is a good marker for drug resistance in ATL patients.

  6. Triterpenoids from Azorella trifurcata (Gaertn.) Pers and their effect against the enzyme acetylcholinesterase

    Energy Technology Data Exchange (ETDEWEB)

    Areche, Carlos; Cejas, Patricia; Thomas, Pablo; San-Martin, Aurelio [University of Chile, Santiago (Chile). Faculty of Sciences. Dept. of Chemistry], e-mail: aurelio@uchile.cl; Astudillo, Luis; Gutierrez, Margarita [University of Talca, Talca (Chile). Inst. of Chemistry of Natural Resource; Loyola, Luis A. [University of Antofagasta (Chile). Faculty of Basic Sciences. Dept. of Chemistry

    2009-07-01

    The inhibition of the enzyme acetylcholinesterase is considered as a strategy for the treatment of Alzheimer's disease, senile dementia, ataxia, and myasthenia gravis. Three lanostane- and two cycloartane-type triterpenes, together with two mulinane-type diterpenes were isolated from petroleum ether extract of the whole shrub of Azorella trifurcata (Gaertn.) Pers. Their effect on the enzyme acetylcholinesterase was assessed as well. In addition, this is the first report of these triterpenes in the genus Azorella. (author)

  7. Triterpenoids from Azorella trifurcata (Gaertn.) Pers and their effect against the enzyme acetylcholinesterase

    International Nuclear Information System (INIS)

    Areche, Carlos; Cejas, Patricia; Thomas, Pablo; San-Martin, Aurelio; Astudillo, Luis; Gutierrez, Margarita; Loyola, Luis A.

    2009-01-01

    The inhibition of the enzyme acetylcholinesterase is considered as a strategy for the treatment of Alzheimer's disease, senile dementia, ataxia, and myasthenia gravis. Three lanostane- and two cycloartane-type triterpenes, together with two mulinane-type diterpenes were isolated from petroleum ether extract of the whole shrub of Azorella trifurcata (Gaertn.) Pers. Their effect on the enzyme acetylcholinesterase was assessed as well. In addition, this is the first report of these triterpenes in the genus Azorella. (author)

  8. Thermosensitive Triterpenoid-Appended Polymers with Broad Temperature Tunability Regulated by Host-Guest Chemistry.

    Science.gov (United States)

    Hao, Jie; Gao, Yuxia; Li, Ying; Yan, Qiang; Hu, Jun; Ju, Yong

    2017-09-05

    Thermoresponsive water-soluble polymers are of great importance since they typically show a lower critical solution temperature (LCST) in aqueous media. In this research, the LCST change in broad temperature ranges of copolymers composed of natural glycyrrhetinic acid (GA)-based methacrylate and N,N'-dimethylacrylamides (DMAs) was investigated as a function of the concentration and the content of GA pendants. By complexation of GA pendants with β-cyclodextrin (β-CD), a side-chain polypseudorotaxane was obtained, which exhibited a significant increase in the LCST of copolymers. Moreover, the precisely reversible control of the LCST behavior was realized through adding a competing guest molecule, sodium 1-admantylcarboxylate. This work illustrates a simple and effective approach to endow water-soluble polymers with broad temperature tunability and helps us further understand the effect of a biocompatible host-guest complementary β-CD/GA pair on the thermoresponsive process. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

  9. A novel triterpenoid carbon skeleton in immature sulphur-rich sediments

    Energy Technology Data Exchange (ETDEWEB)

    Schouten, S.; Sinninghe Damste, J.S.; De Leeuw, J.W. [Netherlands Inst. for Sea Research (NIOZ), Texel (Netherlands)

    1995-03-01

    A novel S compound, 1,4-bis(2{sup {prime}}, 5{sup {prime}}, 5{sup {prime}}, 8a{sup {prime}}-tetramethylhexahydrothiochroman)-butane has been detected in several immature S-rich sediments, of which the desulphurized counterpart was unambiguously identified by synthesis of an authentic standard and coinjection experiments. This C skeleton of the S compound, 1, 10-bis(2{sup {prime}}, 2{sup {prime}}, 6{sup {prime}}-trimethylcyclohexyl)-3,8-dimethyldodecane(I), has not been reported yet in any sediment or organism. We suggest that it may be biosynthesized through an enzymatic cyclization reaction of squalene (II), which shows similarities with the biosynthesis of {Beta}, {Beta}-carotene (III) from lycopene (IV). 24 refs., 4 figs.

  10. Synthesis and biological evaluations of cytotoxic and antiangiogenic triterpenoids-jacaranone conjugates

    DEFF Research Database (Denmark)

    Sun, Hua; Yue, Partick Y. K.; Wang, Shao Rong

    2016-01-01

    showed that these conjugates are more potent in both cytotoxic and antiangiogenic assays than their corresponding parent molecules, and are also selectively more active against melanoma cells B16 and metastatic B16BL6 than the two other cancer cell lines (A549 and MCF-7) tested. The predicted...

  11. Highly oxygenated lanostane-type triterpenoids and their bioactivity from the fruiting body of Ganoderma gibbosum.

    Science.gov (United States)

    Pu, De-Bing; Zheng, Xi; Gao, Jun-Bo; Zhang, Xing-Jie; Qi, Yan; Li, Xiao-Si; Wang, Yong-Mei; Li, Xiao-Nian; Li, Xiao-Li; Wan, Chun-Ping; Xiao, Wei-Lie

    2017-06-01

    Eight new highly oxygenated lanostane triterpenes, gibbosic acids A-H (1-8), along with three known ones (9-11), were isolated from the fruiting body of Ganoderma gibbosum. The structures of new isolates were assigned by NMR and HRESIMS experiments. The absolute configurations of 1 were further confirmed by single crystal X-ray diffraction data and computational ECD methods. Immunoregulatory effect and anti-inflammatory activities of these compounds were screened in murine lymphocyte proliferation assay and in lipopolysaccharide (LPS)-stimulated RAW-264.7 macrophages, respectively. Compound 2 exhibited immunostimulatory effect both in lymphocyte proliferation assay without any induction and ConA-induced mitogenic activity of T-lymphocyte, and the proportion of lymphocyte proliferation at the concentration of 0.1μM are 20.01% and 21.40%, respectively. Copyright © 2017 Elsevier B.V. All rights reserved.

  12. Pentacyclic triterpenoids with nitrogen- and sulfur-containing heterocycles: synthesis and medicinal significance

    Czech Academy of Sciences Publication Activity Database

    Kvasnica, Miroslav; Urban, M.; Dickinson, N.J.; Sarek, J.

    2015-01-01

    Roč. 32, č. 9 (2015), s. 1303-1330 ISSN 0265-0568 R&D Projects: GA ČR(CZ) GJ15-08202Y; GA MŠk(CZ) LO1304; GA MŠk(CZ) LO1204 Institutional support: RVO:61389030 Keywords : BETULINIC ACID-DERIVATIVES * C-LACTAM DERIVATIVES * OLEANOLIC ACID Subject RIV: CC - Organic Chemistry Impact factor: 10.986, year: 2015

  13. Polygalasaponin XXXII, a triterpenoid saponin from Polygalae Radix, attenuates scopolamine-induced cognitive impairments in mice.

    Science.gov (United States)

    Zhou, Heng; Xue, Wei; Chu, Shi-Feng; Wang, Zhen-Zhen; Li, Chuang-Jun; Jiang, Yi-Na; Luo, Lin-Ming; Luo, Piao; Li, Gang; Zhang, Dong-Ming; Chen, Nai-Hong

    2016-08-01

    Recent studies show that the extract of a Chinese herb Polygalae Radix exerts cognition-enhancing actions in rats and humans. The aim of this study was to characterize the pharmacological profiles of active compounds extracted from Polygalae Radix. Two fractions P3 and P6 and two compounds PTM-15 and polygalasaponin XXXII (PGS32) were prepared. Neuroprotective effects were evaluated in primary cortical neurons exposed to high concentration glutamate, serum deficiency or H2O2. Anti-dementia actions were assessed in scopolamine-induced amnesia in mice using step-through avoidance tests and channel water maze tests. After conducting the channel water maze tests, TrkB phosphorylation in mouse hippocampus was detected using Western blotting. Long-term potentiation (LTP) was induced in the dentate gyrus in adult rats; PGS32 (5 μL 400 μmol/L) was injected into the lateral cerebral ventricle 20 min after high frequency stimulation (HFS). Compared to the fraction P6, the fraction P3 showed more prominent neuroprotective effects in vitro and cognition-enhancing effects in scopolamine-induced amnesia in mice. One active compound PGS32 in the fraction P3 exerted potent cognition-enhancing action: oral administration of PGS32 (0.125 mg·kg(-1)·d(-1)) for 19 days abolished scopolamine-induced memory impairment in mice. Furthermore, PGS32 (0.5 and 2 mg·kg(-1)·d(-1)) significantly stimulated the phosphorylation of TrkB in the hippocampus. Intracerebroventricular injection of PGS32 significantly enhanced HFS-induced LTP in the dentate gyrus of rats. PGS32 attenuates scopolamine-induced cognitive impairments in mice, suggesting that it has a potential for the treatment of cognitive dysfunction and dementia.

  14. Surface properties of adsorption layers formed from triterpenoid and steroid saponins

    NARCIS (Netherlands)

    Pagureva, N.; Tcholakova, S.; Golemanov, K.; Denkov, N.; Pelan, E.; Stoyanov, S.D.

    2016-01-01

    Saponins are natural surfactants with non-trivial surface and aggregation properties which find numerous important applications in several areas (food, pharma, cosmetic and others). In the current paper we study the surface properties of ten saponin extracts, having different molecular structure

  15. Isolation of Three Triterpene Saponins, Including Two New Oleanane Derivatives, from Soldanella alpina and Hydrophilic Interaction Liquid Chromatography-Evaporative Light Scattering Detection of these Three Saponins in Four Soldenella Species.

    Science.gov (United States)

    Haller, Julia; Schwaiger, Stefan; Stuppner, Hermann; Gafner, Frank; Ganzera, Markus

    2017-11-01

    The genus Soldanella is one of the few endemic to Europe. Some of its species have relevance in local traditional medicine. Earlier work has indicated the possible presence of saponins in S. alpina. To investigate S. alpina and other related species for the occurrence of saponins. Following sequential extraction with n-hexane, dichloromethane and ethyl acetate the subsequent methanolic extract of S. alpina roots was fractionated after solvent precipitation using fast centrifugal partition chromatography and column chromatography. Structures were elucidated by LC-MS n , high-resolution MS, hydrolysis experiments and one-dimensional (1D)- and two-dimensional (2D)-NMR. A hydrophilic interaction liquid chromatography method was developed to quantitate saponins in the leaves and roots of four Soldanella species. Three triterpene saponins, two of them new natural products, were isolated from S. alpina. Based on an epoxyoleanal aglycone substituted with four sugar units, they were analytically quantitated using a Kinetex 2.6 μm hydrophilic interaction liquid chromatography (HILIC) column together with a mobile phase comprising of ammonium acetate, water and acetonitrile. Method validation confirmed that the assay meets all requirements in respect to linearity, accuracy, sensitivity and precision. All four Soldanella species investigated contained the three saponins. The lowest total level of the three saponins (1.09%) was observed in S. montana leaves while the highest saponin content (5.14%) was determined in S. alpina roots. The detection of saponins within the genus Soldanella is an indication that further phytochemical examination of this genus may reveal more secondary metabolites of interest. Copyright © 2017 John Wiley & Sons, Ltd. Copyright © 2017 John Wiley & Sons, Ltd.

  16. Chemosystematics and diagenesis of terpenoids in fossil conifer species and sediment from the Eocene Zeitz formation, Saxony, Germany

    Science.gov (United States)

    Otto, Angelika; Simoneit, Bernd R. T.

    2001-10-01

    The biomarker contents of three fossil conifer species (Athrotaxis couttsiae, Taxodium balticum, Pinus palaeostrobus) and the clay sediment from the Eocene Zeitz formation, Germany, have been analyzed by gas chromatography-mass spectrometry. Triterpenoids of the oleanane, ursane and lupane series and aliphatic wax lipids are the major compounds in the total extracts of the sediment indicating a major angiosperm input. In contrast, diterpenoids (abietanes, phenolic abietanes, pimaranes, isopimaranes, kauranes, phyllocladanes, totaranes) and lignin degradation products are predominant in the conifer fossil extracts. Polar diterpenoids (ferruginol and derivatives, dehydroabietic acid) are preserved as major compounds in the conifers, accompained by saturated and aromatic diterpenoid products. The extracts of the fossil conifer species show characteristic biomarker patterns and contain terpenoids of chemosystematic value. The terpenoid composition of the fossil conifers is similar to that of related modern species. Phenolic abietanes (ferruginol, 6,7-dehydroferruginol, hydroxyferruginols, sugiol) which are known from modern species of the Cupressaceae and Podocarpaceae are the major terpenoids in shoots of Athrotaxis couttsiae and a cone of Taxodium balticum (both Cupressaceae). Sesquiterpenoids characteristic for Cupressaceae (cuparene, α-cedrene) are also present in Athrotaxis. Abietane-type acids (dehydroabietic acid, abietic acid) and saturated abietanes [fichtelite, 13α(H)-fichtelite] predominate in the extracts of a Pinus palaeostrobus cone and phenolic abietanes are not detectable. A diagenetic pathway for the degradation of abietic acid is proposed based on the presence of abietane-type acids and a series of their presumed degradation products in the Pinus cone. The formation of diagenetic products from the phenolic abietanes is also discussed.

  17. LC-MS/MS Tandem Mass Spectrometry for Analysis of Phenolic Compounds and Pentacyclic Triterpenes in Antifungal Extracts of Terminalia brownii (Fresen

    Directory of Open Access Journals (Sweden)

    Enass Y. A. Salih

    2017-12-01

    Full Text Available Decoctions and macerations of the stem bark and wood of Terminalia brownii Fresen. are used in traditional medicine for fungal infections and as fungicides on field crops and in traditional granaries in Sudan. In addition, T. brownii water extracts are commonly used as sprays for protecting wooden houses and furniture. Therefore, using agar disc diffusion and macrodilution methods, eight extracts of various polarities from the stem wood and bark were screened for their growth-inhibitory effects against filamentous fungi commonly causing fruit, vegetable, grain and wood decay, as well as infections in the immunocompromised host. Ethyl acetate extracts of the stem wood and bark gave the best antifungal activities, with MIC values of 250 µg/mL against Nattrassia mangiferae and Fusarium verticillioides, and 500 µg/mL against Aspergillus niger and Aspergillus flavus. Aqueous extracts gave almost as potent effects as the ethyl acetate extracts against the Aspergillus and Fusarium strains, and were slightly more active than the ethyl acetate extracts against Nattrassia mangiferae. Thin layer chromatography, RP-HPLC-DAD and tandem mass spectrometry (LC-MS/MS, were employed to identify the chemical constituents in the ethyl acetate fractions of the stem bark and wood. The stem bark and wood were found to have a similar qualitative composition of polyphenols and triterpenoids, but differed quantitatively from each other. The stilbene derivatives, cis- (3 and trans- resveratrol-3-O-β-galloylglucoside (4, were identified for the first time in T. brownii. Moreover, methyl-(S-flavogallonate (5, quercetin-7-β-O-di-glucoside (8, quercetin-7-O-galloyl-glucoside (10, naringenin-4′-methoxy-7-pyranoside (7, 5,6-dihydroxy-3′,4′,7-tri-methoxy flavone (12, gallagic acid dilactone (terminalin (6, a corilagin derivative (9 and two oleanane type triterpenoids (1 and (2 were characterized. The flavonoids, a corilagin derivative and terminalin, have not been

  18. Evaluation of the Hepatoprotective Effects of Lantadene A, a Pentacyclic Triterpenoid of Lantana Plants against Acetaminophen-induced Liver Damage

    Directory of Open Access Journals (Sweden)

    Sreenivasan Sasidharan

    2012-11-01

    Full Text Available The aim of the present study was to evaluate the hepatoprotective activity of lantadene A against acetaminophen-induced liver toxicity in mice was studied. Activity was measured by monitoring the levels of aspartate aminotransferase (AST, alanine aminotransferase (ALT, alkaline phosphatase (ALP and bilirubin, along with histo-pathological analysis. Silymarin was used as positive control. A bimodal pattern of behavioural toxicity was exhibited by the lantadene A-treated group at the beginning of the treatment. However, treatment with lantadene A and silymarin resulted in an increase in the liver weight compared with the acetaminophen treated group. The results of the acetaminophen-induced liver toxicity experiments showed that mice treated with lantadene A (500 mg/kg showed a significant decrease in the activity of ALT, AST and ALP and the level of bilirubin, which were all elevated in the acetaminophen treated group (p < 0.05. Histological studies supported the biochemical findings and a maximum improvement in the histoarchitecture was seen. The lantadene A-treated group showed remarkable protective effects against histopathological alterations, with comparable results to the silymarin treated group. The current study confirmed the hepatoprotective effects of lantadene A against the model hepatotoxicant acetaminophen, which is likely related to its potent antioxidative activity.

  19. DETERMINACIÓN DE ÁCIDOS GRASOS Y COMPUESTOS TRITERPENOIDES DEL CUERPO FRUCTIFERO DE Suillus luteus.

    Directory of Open Access Journals (Sweden)

    Ivonne Nieto

    2009-04-01

    Full Text Available Normal 0 21 false false false MicrosoftInternetExplorer4 /* Style Definitions */ table.MsoNormalTable {mso-style-name:"Tabla normal"; mso-tstyle-rowband-size:0; mso-tstyle-colband-size:0; mso-style-noshow:yes; mso-style-parent:""; mso-padding-alt:0cm 5.4pt 0cm 5.4pt; mso-para-margin:0cm; mso-para-margin-bottom:.0001pt; mso-pagination:widow-orphan; font-size:10.0pt; font-family:"Times New Roman"; mso-ansi-language:#0400; mso-fareast-language:#0400; mso-bidi-language:#0400;} Del cuerpo fructífero de Suillus luteus se extrajeron e identificaron, con base en el análisis de sus espectros de masas,  dieciséis compuestos, los cuales corresponden al ácido palmítico, oléico, linolénico y linoléico, octadecanoato de etilo, ergosta-7,22-dien-3β-ol, ergosta-7-en-3β-ol, estigmasterol, ergosta-3,5,7,9(11,22-pentaeno, ergosta-2,5,7,9(11,14,22-hexaeno, 23-metil-estigmast-3,5,7,22-tetraeno, 23-metil-estigmast-3,5,7,9(11,22-pentaeno, ergosta-4,6,15(16,22-tetraen-3-ona,  ergosta-1,5,7,9(11,22-pentaen-3-ona, ergosta-5,7,9(11,22-tetraen-3β-ol y ergosta-5,6,7-trihidroxi-7,22-dien-3β-ol. Siendo este un hongo tan poco estudiado, todos los compuestos, a excepción de los ácidos grasos, se reportan aquí por primera vez.

  20. Antihyperglycemic and hypolipidemic effects of α, β-amyrin, a triterpenoid mixture from Protium heptaphyllum in mice

    Directory of Open Access Journals (Sweden)

    Santos Flávia

    2012-08-01

    Full Text Available Abstract Background Pentacyclic triterpenes in general exert beneficial effects in metabolic disorders. This study investigated the effects of α, β-amyrin, a pentacyclic triterpene mixture from the resin of Protium heptaphyllum on blood sugar level and lipid profile in normal and streptozotocin (STZ-induced diabetic mice, and in mice fed on a high-fat diet (HFD. Findings Mice treated with α, β-amyrin (10, 30 and 100 mg/kg, p.o. or glibenclamide (10 mg/kg, p.o. had significantly reduced STZ-induced increases in blood glucose (BG, total cholesterol (TC and serum triglycerides (TGs. Unlike glibenclamide that showed significant reductions in BG, TC and TGs in normoglycemic mice, α, β-amyrin did not lower normal blood sugar levels but at 100 mg/kg, manifested a hypolipidemic effect. Also, α, β-amyrin effectively reduced the elevated plasma glucose levels during the oral glucose tolerance test. Moreover, the plasma insulin level and histopathological analysis of pancreas revealed the beneficial effect of α, β-amyrin in the preservation of beta cell integrity. In mice treated orally with α, β-amyrin (10, 30 and 100 mg/kg or fenofibrate (200 mg/kg, the HFD-associated rise in serum TC and TGs were significantly less. The hypocholesterolemic effect of α, β-amyrin appeared more prominent at 100 mg/kg with significant decreases in VLDL and LDL cholesterol and an elevation of HDL cholesterol. Besides, the atherogenic index was significantly reduced by α, β-amyrin. Conclusions These findings reflect the potential antihyperglycemic and hypolipidemic effects of α, β-amyrin mixture and suggest that it could be a lead compound for drug development effective in diabetes and atherosclerosis.

  1. Accumulation of Rutin and Betulinic Acid and Expression of Phenylpropanoid and Triterpenoid Biosynthetic Genes in Mulberry (Morus alba L.).

    Science.gov (United States)

    Zhao, Shicheng; Park, Chang Ha; Li, Xiaohua; Kim, Yeon Bok; Yang, Jingli; Sung, Gyoo Byung; Park, Nam Il; Kim, Soonok; Park, Sang Un

    2015-09-30

    Mulberry (Morus alba L.) is used in traditional Chinese medicine and is the sole food source of the silkworm. Here, 21 cDNAs encoding phenylpropanoid biosynthetic genes and 21 cDNAs encoding triterpene biosynthetic genes were isolated from mulberry. The expression levels of genes involved in these biosynthetic pathways and the accumulation of rutin, betulin, and betulinic acid, important secondary metabolites, were investigated in different plant organs. Most phenylpropanoid and triterpene biosynthetic genes were highly expressed in leaves and/or fruit, and most genes were downregulated during fruit ripening. The accumulation of rutin was more than fivefold higher in leaves than in other organs, and higher levels of betulin and betulinic acid were found in roots and leaves than in fruit. By comparing the contents of these compounds with gene expression levels, we speculate that MaUGT78D1 and MaLUS play important regulatory roles in the rutin and betulin biosynthetic pathways.

  2. The triterpenoid corosolic acid blocks transformation and epigenetically reactivates Nrf2 in TRAMP-C1 prostate cells.

    Science.gov (United States)

    Yang, Jie; Wu, Renyi; Li, Wenji; Gao, Linbo; Yang, Yuqing; Li, Ping; Kong, Ah-Ng

    2018-04-01

    Corosolic acid (CRA) is found in various plants and has been used as a health food supplement worldwide. Although it has been reported that CRA exhibits significant anticancer activity, the effect of this compound on prostate cancer remains unknown. In this study, we investigated the effect of CRA on cellular transformation and the reactivation of nuclear factor erythroid 2-related factor 2 (Nrf2) through epigenetic regulation in TRAMP-C1 prostate cells. Specifically, we found that CRA inhibited anchorage-independent growth of prostate cancer TRAMP-C1 cells but not Nrf2 knockout prostate cancer TRAMP-C1 cells. Moreover, CRA induced mRNA and protein expression of Nrf2, heme oxygenase-1 (HO-1) and NAD(P)H Quinone Oxidoreductase 1 (NQO1). Bisulfite genomic sequencing and methylated DNA immunoprecipitation results revealed that CRA treatment decreased the level of methylation of the first five CpG sites of the Nrf2 promoter. Histone modification was analyzed using a chromatin immunoprecipitation (ChIP) assay, which revealed that CRA treatment increased the acetylation of histone H3 lysine 27 (H3K27ac) while decreasing the trimethylation of histone H3 lysine 27 (H3K27me3) in the promoter region of Nrf2. Furthermore, CRA treatment attenuated the protein expression of DNA methyltransferases (DNMTs) and histone deacetylases (HDACs). These findings indicate that CRA has a significant anticancer effect in TRAMP-C1 cells, which could be partly attributed to epigenetics including its ability to epigenetically restore the expression of Nrf2. © 2017 Wiley Periodicals, Inc.

  3. Lebbeckoside C, a new triterpenoid saponin from the stem barks of Albizia lebbeck inhibits the growth of human glioblastoma cells.

    Science.gov (United States)

    Noté, Olivier Placide; Ngo Mbing, Joséphine; Kilhoffer, Marie-Claude; Pegnyemb, Dieudonné Emmanuel; Lobstein, Annelise

    2018-02-19

    One new acacic acid-type saponin, named lebbeckoside C (1), was isolated from the stem barks of Albizia lebbeck. Its structure was established on the basis of extensive analysis of 1D and 2D NMR ( 1 H, 13 C NMR, DEPT, COSY, TOCSY, ROESY, HSQC and HMBC) experiments, HRESIMS studies, and by chemical evidence as 3-O-[β-d-xylopyranosyl-(l→2)-β-d-fucopyranosyl-(1→6)-[β-d-glucopyranosyl(1→2)]-β-d-glucopyranosyl]-21-O-{(2E,6S)-6-O-{4-O-[(2E,6S)-2,6-dimethyl-6-O-(β-d-quinovopyranosyl)octa-2,7-dienoyl]-4-O-[(2E,6S)-2,6-dimethyl-6-O-(β-d-quinovopyranosyl)octa-2,7-dienoyl]-β-d-quinovopyranosyl}-2,6-dimethylocta-2,7-dienoyl}acacic acid 28 O-[β-d-quinovopyranosyl-(l→3)-[α-l-arabinofuranosyl-(l→4)]-α-l-rhamnopyranosyl-(l→2)-β-d-glucopyranosyl] ester. The isolated saponin (1) displayed significant cytotoxic activity against the human glioblastoma cell line U-87 MG and TG1 stem-like glioma cells isolated from a patient tumor with IC 50 values of 1.69 and 1.44 μM, respectively.

  4. Metabolomic analysis of methyl jasmonate-Induced triterpenoid production in the medicinal herb Centella asiatica (L.) Urban

    CSIR Research Space (South Africa)

    James, TJ

    2013-04-01

    Full Text Available as well as their aglycones, asiatic acid and madecassic acid. Cell suspensions were treated with 0.2 mM MeJa for 2, 4 and 6 days. Liquid chromatography coupled to mass spectrometry (LC-MS) was used to explore induced changes in metabolite profiles, both...

  5. Olean-18-ene triterpenoids from Celastraceae species inhibit HIV replication targeting NF-kB and Sp1 dependent transcription.

    Science.gov (United States)

    Osorio, Alex A; Muñóz, Alejandro; Torres-Romero, David; Bedoya, Luis M; Perestelo, Nayra R; Jiménez, Ignacio A; Alcamí, José; Bazzocchi, Isabel L

    2012-06-01

    In the present study we report the isolation of nine new olean-18-ene triterpenes (1-9), along with three known ones (10-12), from Cassine xylocarpa and Maytenus jelskii. Their stereostructures have been elucidated on the basis of spectroscopic analysis, including 1D and 2D NMR techniques (COSY, ROESY, HSQC and HMBC), and spectrometric methods. The natural compounds and derivatives 13-15 have been tested for their potential as inhibitors of human immunodeficiency virus type 1 replication. Five compounds from this series displayed potent antiviral activity with IC(50)s in the micromolar range (1, 3, 4, 7 and 8) being 1 and 8 the most active compounds. The target of these compounds was different from antiretroviral drugs currently licensed as they act as inhibitors of enhancer-dependent transcription. The structure-activity relationships were established based on the regiosubstitution and oxidation degree of the triterpene scaffold, revealing that these aspects were able to modulate the selectivity and intensity of HIV inhibition. Copyright © 2012 Elsevier Masson SAS. All rights reserved.

  6. Triterpenoid α-amyrin stimulates proliferation of human keratinocytes but does not protect them against UVB damage

    DEFF Research Database (Denmark)

    Biskup, Edyta; Gołębiowski, Marek; Gniadecki, Robert

    2012-01-01

    Rhaponticum carthamoides plants ("maral root") are widely used in Siberian folk medicine. The present study reports for the first time the presence of pentacyclic terpenoid, α-amyrin, in methanol extract from leaves of this plant. α-Amyrin induced proliferation of human keratinocytes (HaCaT) by a...

  7. Colossolactone H, a new Ganoderma triterpenoid exhibits cytotoxicity and potentiates drug efficacy of gefitinib in lung cancer.

    Science.gov (United States)

    Chen, Su-Yu; Chang, Chao-Lin; Chen, Teng-Hai; Chang, Ya-Wen; Lin, Shwu-Bin

    2016-10-01

    Three pentacyclic triterpene dilactones were isolated from the fruiting bodies of Ganoderma colossum, a medicinal mushroom. Colossolactone H (colo H) as a new compound and the most cytotoxic among the isolates was studied for its anticancer mechanism and the potential use in cancer therapy. Gene expression profiling analysis indicated that treatment of lung cancer cells with colo H caused upregulation of 252 genes and downregulation of 398 genes. Gene ontology enrichment analysis indicated that the downregulated genes were the most significantly enriched in cell cycle progression, and the upregulated genes were significantly enriched in metabolic process, cellular response to stimulus, and oxidation reduction. Accordingly, colo H was found to halt cell growth and induce cell apoptosis via the elevation of cellular reactive oxygen species to cause DNA damage and the increase of tumor suppressor p53 protein. These events facilitate additive cytotoxicity of colo H and gefitinib for gefitinib-resistant H1650 lung cancer cells. Furthermore, combination of colo H and gefitinib effectively inhibited the growth of tumor xenografts in athymic mice. In addition to the efficacy in adjunctive cancer therapy, we have also demonstrated the isolation of colo H from cultivated G. colossum. Thus it is feasible to use colo H or Ganoderma colossum for cancer therapy. Copyright © 2016. Published by Elsevier B.V.

  8. RNAi and Homologous Over-Expression Based Functional Approaches Reveal Triterpenoid Synthase Gene-Cycloartenol Synthase Is Involved in Downstream Withanolide Biosynthesis in Withania somnifera.

    Directory of Open Access Journals (Sweden)

    Smrati Mishra

    Full Text Available Withania somnifera Dunal, is one of the most commonly used medicinal plant in Ayurvedic and indigenous medicine traditionally owing to its therapeutic potential, because of major chemical constituents, withanolides. Withanolide biosynthesis requires the activities of several enzymes in vivo. Cycloartenol synthase (CAS is an important enzyme in the withanolide biosynthetic pathway, catalyzing cyclization of 2, 3 oxidosqualene into cycloartenol. In the present study, we have cloned full-length WsCAS from Withania somnifera by homology-based PCR method. For gene function investigation, we constructed three RNAi gene-silencing constructs in backbone of RNAi vector pGSA and a full-length over-expression construct. These constructs were transformed in Agrobacterium strain GV3101 for plant transformation in W. somnifera. Molecular and metabolite analysis was performed in putative Withania transformants. The PCR and Southern blot results showed the genomic integration of these RNAi and overexpression construct(s in Withania genome. The qRT-PCR analysis showed that the expression of WsCAS gene was considerably downregulated in stable transgenic silenced Withania lines compared with the non-transformed control and HPLC analysis showed that withanolide content was greatly reduced in silenced lines. Transgenic plants over expressing CAS gene displayed enhanced level of CAS transcript and withanolide content compared to non-transformed controls. This work is the first full proof report of functional validation of any metabolic pathway gene in W. somnifera at whole plant level as per our knowledge and it will be further useful to understand the regulatory role of different genes involved in the biosynthesis of withanolides.

  9. Characterization and Quantitation of Triterpenoid Saponins in Raw and Sprouted Chenopodium berlandieri spp. (Huauzontle) Grains Subjected to Germination with or without Selenium Stress Conditions.

    Science.gov (United States)

    Lazo-Vélez, Marco A; Guajardo-Flores, Daniel; Mata-Ramírez, Daniel; Gutiérrez-Uribe, Janet A; Serna-Saldivar, Sergio O

    2016-01-01

    Pseudocereal Chenopodium berlandieri spp. (huauzontle) was evaluated to determine saponin composition. Saponins were evaluated in raw and germinated grains subjected to chemical stress induced by sodium selenite. Analysis by liquid chromatography coupled with ELSD detector revealed the presence of 12 saponins, identified according to compounds previously assayed in Chenopodium quinoa. Saponins found at the highest concentrations in raw grains were derived from oleanolic and phytolaccagenic acids. Total saponin concentration significantly decreased in germinated compared to raw grains due to the significant loss of 90.1% and 95.7% of the phytolaccagenic acid without and with chemical selenium stress, respectively. The most abundant saponin in germinated sprouts decreased during normal germination. Interestingly, the concentration of this particular saponin significantly increased during the Se-induced stress germination. Chemical stress with selenium salts proved to change the saponin composition in geminated Chenopodium berlandieri spp. grains, therefore affecting their potential use as ingredient in the food industry. © 2015 Institute of Food Technologists®

  10. Structure revision of hupehensis saponin F and G and characterization of new trace triterpenoid saponins from Anemone hupehensis by tandem electrospray ionization mass spectrometry.

    Science.gov (United States)

    Li, Fu; Liu, Xin; Tang, Minghai; Chen, Bin; Ding, Lisheng; Chen, Lijuan; Wang, Mingkui

    2012-05-15

    Electrospray ionization ion-trap tandem mass spectrometry (ESI-MS(n)) was first employed for reinvestigating the structures of hupehensis saponin F and G previously isolated from Anemone hupehensis in our lab. Hupehensis saponin G was determined to contain one more trisaccharide unit (Rha-(1→4)-Glc-(1→6)-Glc-), not a glucose residue, than saponin F based on their molecular weights deduced from their [M+Na](+) ions in ESI-MS spectra. The (2,4)A(4α)-ion at m/z 551.3 formed by retro-Diels-Alder (RDA) rearrangement in positive mode illustrated that the C-28 sugar chains of the two saponins were composed of trisaccharide repeating moieties with (1→4) linkages rather than (1→3) linkages. The interpretation of 2D-NMR spectra of the two compounds also confirmed the results obtained by ESI-MS(n). Moreover, from the water soluble part of A. hupehensis, two novel triterpene saponins were tentatively characterized to contain 4 and 5 (1→4)-linked above trisaccharide repeating moieties at C-28 position according to their ESI-MS(n) behaviors, respectively. Copyright © 2012 Elsevier Ltd. All rights reserved.

  11. Inhibition of amyloid β aggregation and protective effect on SH-SY5Y cells by triterpenoid saponins from the cactus Polaskia chichipe.

    Science.gov (United States)

    Fujihara, Koji; Koike, Shin; Ogasawara, Yuki; Takahashi, Kunio; Koyama, Kiyotaka; Kinoshita, Kaoru

    2017-07-01

    Alzheimer's disease (AD) destroys brain function, especially in the hippocampus, and is a social problem worldwide. A major pathogenesis of AD is related to the accumulation of amyloid beta (Aβ) peptides, resulting in neuronal cell death in the brain. Here, we isolated four saponins (1-4) and elucidated their structures from 1D and 2D NMR and HRFABMS spectral data. The structures of 1 and 2 were determined as new saponins which have cochalic acid as the aglycon, and 3 was determined as a new saponin with oleanolic acid as the aglycon. Compound 4 was confirmed as the known saponin chikusetsusaponin V (=ginsenoside R 0 ). Isolated saponins (1-4) and six previously reported saponins (5-10) were tested for their inhibitory effects of Aβ aggregation and their protective effects on SH-SY5Y cells against Aβ-associated toxicity. As the results, compounds 3 and 4 showed inhibitory effect of Aβ aggregation and compounds 5-8 exerted the protective effects on SH-SY5Y cells against Aβ-associated toxicity. Copyright © 2017 Elsevier Ltd. All rights reserved.

  12. In silico PASS analysis and determination of antimycobacterial, antifungal, and antioxidant efficacies of maslinic acid in an extract rich in pentacyclic triterpenoids

    Directory of Open Access Journals (Sweden)

    Prasad G Jamkhande

    2016-01-01

    Conclusion: This work provides scientific evidence of the antioxidant, antifungal, and antimycobacterial activities of MA, showing its potential application in the development of natural antioxidants and antimicrobial agents for the agro-food and pharmaceutical industries.

  13. Transport of cryptotanshinone, a major active triterpenoid in Salvia miltiorrhiza Bunge widely used in the treatment of stroke and Alzheimer's disease, across the blood-brain barrier.

    Science.gov (United States)

    Yu, Xi-Yong; Lin, Shu-Guang; Chen, Xiao; Zhou, Zhi-Wei; Liang, Jun; Duan, Wei; Chowbay, Balram; Wen, Jing-Yuan; Chan, Eli; Cao, Jie; Li, Chun-Guang; Zhou, Shu-Feng

    2007-05-01

    Cryptotanshinone (CTS), a major constituent from the roots of Salvia miltiorrhiza (Danshen), is widely used in the treatment of coronary heart disease, stroke and less commonly Alzheimer's disease. Our recent study indicates that CTS is a substrate for P-glycoprotein (PgP/MDR1/ABCB1). This study has investigated the nature of the brain distribution of CTS across the brain-blood barrier (BBB) using several in vitro and in vivo rodent models. A polarized transport of CTS was found in rat primary microvascular endothelial cell (RBMVEC) monolayers, with facilitated efflux from the abluminal side to luminal side. Addition of a PgP (e.g. verapamil and quinidine) or multi-drug resistance protein 1/2 (MRP1/2) inhibitor (e.g. probenecid and MK-571) in both luminal and abluminal sides attenuated the polarized transport. In a bilateral in situ brain perfusion model, the uptake of CTS into the cerebrum increased from 0.52 +/- 0.1% at 1 min to 11.13 +/- 2.36 ml/100 g tissue at 30 min and was significantly greater than that of sucrose. Co-perfusion of a PgP/MDR1 (e.g. verapamil) or MRP1/2 inhibitor (e.g. probenecid) significantly increased the brain distribution of CTS by 35.1-163.6%. The brain levels of CTS were only about 21% of those in plasma, and were significantly increased when coadministered with verapamil or probenecid in rats. The brain levels of CTS in rats subjected to middle cerebral artery occlusion and rats treated with quinolinic acid (a neurotoxin) were about 2- to 2.5-fold higher than the control rats. Moreover, the brain levels in mdr1a(-/-) and mrp1(-/-) mice were 10.9- and 1.5-fold higher than those in the wild-type mice, respectively. Taken collectively, these findings indicate that PgP and Mrp1 limit the brain penetration of CTS in rodents, suggesting a possible role of PgP and MRP1 in limiting the brain penetration of CTS in patients and causing drug resistance to Danshen therapy and interactions with conventional drugs that are substrates of PgP and MRP1. Further studies are needed to explore the role of other drug transporters in restricting the brain penetration of CTS and the clinical relevance.

  14. Bioactive non-sterol triterpenoid from Streblus asper: microwave-assisted extraction, HPTLC profiling, computational studies and neuro-pharmacological evaluation in BALB/c mice.

    Science.gov (United States)

    Verma, Vandana; Tripathi, Avinash C; Saraf, Shailendra K

    2016-11-01

    In folk medicine, the stem bark of Streblus asper Lour. (Moraceae) has been reported to possess anticonvulsant activity. However, no systematic/scientific validation is available. Objective This study explores the constituents in the stem bark, their biosassy-guided isolation and their efficacy in neuro-pharmacological disorders, for validating the traditional claims. Microwave-assisted extraction (MAE) technique was employed to obtain the crude extract. The n-hexane, dichloromethane and aqueous fractions were prepared and phytoconstituents were ascertained by phytochemical tests. The isolated compound, betulin, was characterized by different physicochemical and spectral methods, including HPTLC. Finally, neuro-pharmacological evaluations were conducted at 100, 200, 400 mg/kg b.w., p.o. (25, 50, 100 mg/kg b.w. for betulin) doses in BALB/c mice. The n-hexane fraction (400 mg/kg), and isolated compound betulin (100 mg/kg), showed maximum anticonvulsant activity in maximal electroshock (87.84% and 85.14% seizure inhibition), and isoniazid induced convulsion models (88.85% and 83.18% seizure inhibition), respectively. A dose-dependent attenuation of epileptic seizures was observed, probably through GABArgic mechanism of anticonvulsant action. Moreover, the antidepressant study was also conducted using behavioural models and the results expound that n-hexane and dichloromethane fractions (400 mg/kg) significantly reduced the duration of immobility, as compared to the control. This study reports some novel aspects like applying an environmentally benign/green approach of MAE, neuro-pharmacological screening and use of docking studies, for the first time, on the plant S. asper. The findings present a rational explanation for its use in traditional medicine, for the management of neuro-pharmacological disorders.

  15. Synthetic triterpenoid inhibition of human ghrelin O-acyltransferase: Involvement of a functionally required cysteine provides mechanistic insight into ghrelin acylation

    OpenAIRE

    McGovern-Gooch, Kayleigh R.; Mahajani, Nivedita S.; Garagozzo, Ariana; Schramm, Anthony J.; Hannah, Lauren G.; Sieburg, Michelle A.; Chisholm, John D.; Hougland, James L.

    2017-01-01

    The peptide hormone ghrelin plays a key role in regulating hunger and energy balance within the body. Ghrelin signaling presents a promising and unexploited target for development of small-molecule therapeutics to treat obesity, diabetes, and other health conditions. Inhibition of ghrelin O-acyltransferase (GOAT), which catalyzes an essential octanoylation step in ghrelin maturation, offers a potential avenue for controlling ghrelin signaling. Through screening a small molecule library, we ha...

  16. Exploring the Cytotoxic Potential of Triterpenoids-enriched Fraction of Bacopa monnieri by Implementing In vitro, In vivo, and In silico Approaches

    OpenAIRE

    Mallick, Md. Nasar; Khan, Washim; Parveen, Rabea; Ahmad, Sayeed; Sadaf,; Najm, Mohammad Zeeshan; Ahmad, Istaq; Husain, Syed Akhtar

    2017-01-01

    Background: Bacopa monnieri (BM) is a herbaceous plant traditionally used from time immemorial in Ayurvedic and folklore medicines. We hypothesized that the extract of the whole plant might contain numerous molecules with having antitumor activities that could be very effective in killing of human cancer cells. Objectives: This work investigated anticancer activity of bioactive fraction of BM. Materials and Methods: The hydroalcoholic extract of BM was fractionated with different solvent, nam...

  17. Exploring the Cytotoxic Potential of Triterpenoids-enriched Fraction of Bacopa monnieri by Implementing In vitro, In vivo, and In silico Approaches.

    Science.gov (United States)

    Mallick, Md Nasar; Khan, Washim; Parveen, Rabea; Ahmad, Sayeed; Sadaf; Najm, Mohammad Zeeshan; Ahmad, Istaq; Husain, Syed Akhtar

    2017-10-01

    Bacopa monnieri (BM) is a herbaceous plant traditionally used from time immemorial in Ayurvedic and folklore medicines. We hypothesized that the extract of the whole plant might contain numerous molecules with having antitumor activities that could be very effective in killing of human cancer cells. This work investigated anticancer activity of bioactive fraction of BM. The hydroalcoholic extract of BM was fractionated with different solvent, namely, hexane, dichloromethane (DCM), acetone, methanol, and water. The in vitro anticancer activity was performed against various Human Cancer Cell lines, namely, Colon (HT29, Colo320, and Caco2), Lung (A549), Cervix (HeLa, SiHa), and Breast (MCF-7, MDAMB-231). Further, DCM fraction was evaluated in vivo for anticancer activity against Ehrlich ascites carcinoma (EAC) tumor-bearing mice since it showed the best cytotoxicity at 72 h (IC 50 41.0-60.0 µg/mL). The metabolic fingerprinting of these extract were carried out using high-performance thin-layer chromatography along with quantification of bacoside A, bacoside B, cucurbitacin B, cucurbitacin E, and bittulinic acid. Oral administration of DCM fraction at a dose of 40 mg/kg rendered prominent reduction of tumor regression parameters such as tumor weight, packed cell volume, tumor volume and viable tumor cell count as compared to the untreated mice of the EAC control group. The anticancer activity of DCM fraction may be due to the presence of large amount of bacoside A, B and cucurbitacins. The molecular docking studies of major metabolites with targeted proteins predicted the anticancer activity of DCM fraction which was in support of in vivo activity. The in vitro , in vivo , analytical and in silico studies on DCM fraction of Bacopa monieri has proved its great potential for development of anticancer phytopharmaceuticals. A new HPTLC method has been developed and validated for the qualitative and quantitative analysis of bacoside A, B, cucurbitacin B, D, E and bittulinic acid in Bacopa monnieri extract. Enrichment of active anticancer metabolites was done by polarity based fractionations of hydroalcoholic extract of Bacopa. DCM fraction of a hydroalcoholic extract of Bacopa showed anticancer potential against human cancer cell line (IC50 41.0-60.0 µg/mL) and in EAC treated mice (at a dose of 40 mg/kg body weight). The anticancer activity of Bacopa may be due to the presence of bacosides and cucurbitacin and it was confirmed by in silico screening. Abbreviations used: DBM: DCM fraction of Bacopa monnieri; DCM: Dichloromethane; EAC: Ehrlich ascites carcinoma; HCT: Hematocrit; HGB: Hemoglobin; HPTLC: High performance thin layer chromatography; ICH: International council for Harmonisation; LOD: Limit of detection; LOQ: Limit of quantification; LYM: Lymphocytes; MCH: Mean corpuscular hemoglobin; MCHC: Mean corpuscular haemoglobin concentration (MCHC); MCV: Mean corpuscular volume; MTT: 3-(4, 5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide; PLT: Platelet; RBC: Red blood cell; RDW: Red blood cell distribution width; RSD: Relative standard deviation; WBC: White blood cells.

  18. Cucurbitane Triterpenoid from Momordica charantia Induces Apoptosis and Autophagy in Breast Cancer Cells, in Part, through Peroxisome Proliferator-Activated Receptor γ Activation

    Directory of Open Access Journals (Sweden)

    Jing-Ru Weng

    2013-01-01

    Full Text Available Although the antitumor activity of the crude extract of wild bitter gourd (Momordica charantia L. has been reported, its bioactive constituents and the underlying mechanism remain undefined. Here, we report that 3β,7β-dihydroxy-25-methoxycucurbita-5,23-diene-19-al (DMC, a cucurbitane-type triterpene isolated from wild bitter gourd, induced apoptotic death in breast cancer cells through peroxisome proliferator-activated receptor (PPAR γ activation. Luciferase reporter assays indicated the ability of DMC to activate PPARγ, and pharmacological inhibition of PPARγ protected cells from DMC's antiproliferative effect. Western blot analysis indicated that DMC suppressed the expression of many PPARγ-targeted signaling effectors, including cyclin D1, CDK6, Bcl-2, XIAP, cyclooxygenase-2, NF-κB, and estrogen receptor α, and induced endoplasmic reticulum stress, as manifested by the induction of GADD153 and GRP78 expression. Moreover, DMC inhibited mTOR-p70S6K signaling through Akt downregulation and AMPK activation. The ability of DMC to activate AMPK in liver kinase (LK B1-deficient MDA-MB-231 cells suggests that this activation was independent of LKB1-regulated cellular metabolic status. However, DMC induced a cytoprotective autophagy presumably through mTOR inhibition, which could be overcome by the cotreatment with the autophagy inhibitor chloroquine. Together, the ability of DMC to modulate multiple PPARγ-targeted signaling pathways provides a mechanistic basis to account for the antitumor activity of wild bitter gourd.

  19. Journal of Biosciences | Indian Academy of Sciences

    Indian Academy of Sciences (India)

    Triterpenoids are pentacyclic secondary metabolites present in many terrestrial plants. Natural triterpenoids have been reported to exhibit anti-inflammatory and anti-carcinogenic activities. Here, we show that modifications of ring A of boswellic acid (2 cyano, 3 enone) resulted in a highly active growth inhibitory, ...

  20. BRIONONIC ACID FROM THE HEXANE EXTRACT OF Sandoricum koetjape MERR STEM BARK (meliaceae

    Directory of Open Access Journals (Sweden)

    Tukiran Tukiran

    2010-06-01

    Full Text Available An oleane-type triterpenoid, briononic acid was isolated from hexane extract of the stem bark of Sandoricum koetjape Merr. (Meliaceae. This structure had been established based on spectroscopic data (UV, IR, and NMR and by comparison with spectroscopic data of related compound that had been reported.   Keywords: Meliaceae, Oleane, Sandoricum koetjape Merr., Triterpenoid

  1. Kandungan Bahan Aktif Tanaman Pegagan dan Khasiatnya untuk Meningkatkan Sistem Imun Tubuh

    OpenAIRE

    Sutardi, Sutardi

    2016-01-01

    Pegagan (Centella asiatica (L.) Urban) merupakan tanaman yang banyak dimanfaatkan sebagai obat tradisional untuk menyem-buhkan berbagai penyakit. Pegagan mengandung bahan aktif alkaloid, saponin, tanin, flavonoid, steroid, dan triterpenoid. Tiga golongan bioaktif, yaitu triterpenoid, steroid, dan saponin termasuk antioksidan yang bermanfaat bagi kesehatan tubuh manusia. Bahan aktif tersebut merupakan bahan baku obat tradisional yang bermanfaat sebagai antipikun, antistres, obat lemah syaraf, ...

  2. Dianthosaponins A-F, triterpene saponins, flavonoid glycoside, aromatic amide glucoside and γ-pyrone glucoside from Dianthus japonicus.

    Science.gov (United States)

    Nakano, Takahiro; Sugimoto, Sachiko; Matsunami, Katsuyoshi; Otsuka, Hideaki

    2011-01-01

    From aerial parts of Dianthus japonicus, six new and seven known oleanane-type triterpene saponins were isolated. The structures of the new saponins, named dianthosaponins A-F, were elucidated by means of high resolution mass spectrometry, and extensive inspection of one- and two-dimensional NMR spectroscopic data. A new C-glycosyl flavone, a glycosidic derivative of anthranilic acid amide and a maltol glucoside were also isolated.

  3. Triterpenes and flavonol glucuronides from Oenothera cheiranthifolia.

    Science.gov (United States)

    Nakanishi, Tsutomu; Inatomi, Yuka; Murata, Hiroko; Ishida, Syun-Suke; Fujino, Yuri; Miura, Kanako; Yasuno, Yoshito; Inada, Akira; Lang, Frank A; Murata, Jin

    2007-02-01

    A new ursane-type triterpene, named as cheiranthic acid (1), was isolated from the MeOH extract of whole plants of Oenothera cheiranthifolia (Onagraceae) along with an isomeric pair of known oleanane- and ursane-type triterpenes (arjunolic acid and asiatic acid) and three flavonol glucuronide analogues (quercetin 3-O-glucuronide, its n-butyl ester, and myricetin 3-O-glucuronide). Their structures were elucidated based on spectroscopic evidence.

  4. Photochemistry and pharmacology of 9, 19-cyclolanostane glycosides isolated from genus Cimicifuga.

    Science.gov (United States)

    Su, Yang; Chi, Wen-Cheng; Wu, Lun; Wang, Qiu-Hong; Kuang, Hai-Xue

    2016-10-01

    The constituents of Cimicifuga plants have been extensively investigated, and the principal metabolites are 9, 19-cyclolanostane triterpenoid glycosides, which often exhibit extensive pharmacological activities. 9, 19-Cyclolanostane triterpenoid glycosides are distributed widely in genus Cimicifuga rather than in other members of the Ranunculaceae family. So far, more than 140 cycloartane triterpene glycosides have been isolated from Cimicifuga spp.. The aim of this review was to summarize all 9, 19-cyclolanostane triterpenoid glycosides based on the available relevant scientific literatures from 2000 to 2014. Biological studies of cycloartane triterpene glycosides from Cimicifuga spp. are also discussed. Copyright © 2016 China Pharmaceutical University. Published by Elsevier B.V. All rights reserved.

  5. The terpene synthase gene family in Tripterygium wilfordii harbors a labdane-type diterpene synthase among the monoterpene synthase TPS-b subfamily

    DEFF Research Database (Denmark)

    Hansen, Nikolaj Lervad; Heskes, Allison Maree; Hamberger, Britta

    2017-01-01

    Tripterygium wilfordii (Celastraceae) is a medicinal plant with anti-inflammatory and immunosuppressive properties. Identification of a vast array of unusual sesquiterpenoids, diterpenoids and triterpenoids in T. wilfordii has spurred investigations of their pharmacological properties. The tri-ep...

  6. Structure-Activity Relationship Studies on Derivatives of Eudesmanolides from Inula Helenium as Toxicants against Aedes Aegypti Larvae and Adults

    Science.gov (United States)

    2010-01-01

    bioassay was performed on compounds representing many classes of natural compounds including polyacetylenes, phytosterols, flavonoids ... flavonoids , sesquiterpenoids, and triterpenoids, among others, were CHEMISTRY & BIODIVERSITY – Vol. 7 (2010)1682 Table 1. Larvicidal Activities of Various

  7. Ogunlana et al., Afr J Tradit Complement Altern Med. (2013) 10(6 ...

    African Journals Online (AJOL)

    AJTCAM

    ... the plant shows that it contains saponins, alkaloids, flavonoids, triterpenoids, diterpenoids, .... The histopathological study of kidney, liver, spleen and heart removed from the experimental ..... In renal failure, there is an increase in metabolic.

  8. MEDICINAL, PHARMACOLOGICAL AND PHYTOCHEMICAL ...

    African Journals Online (AJOL)

    DR. AMINU

    2013-06-01

    Jun 1, 2013 ... alkaloids, flavonoids, saponins, tannins, steroids, triterpenoids and phytosterols. This review was ... Thanks to modern technology, science can now identify some .... The methanolic extract of A. comosus peel was inactive to B.

  9. Aqueous Extract of Flueggea leucopyrus Increases Urine Output in ...

    African Journals Online (AJOL)

    1Faculty of Science, Department of Chemistry, 2Department of Zoology, University of ... tertiary, quaternary alkaloids/amine oxides, triterpenoids, unsaturated sterols, leucoanthocyanins, ..... Chemical Synthesis and biological activities of.

  10. Isolation and quantification of Quillaja saponaria Molina saponins and lipids in iscom-matrix and iscoms.

    Science.gov (United States)

    Behboudi, S; Morein, B; Rönnberg, B

    1995-12-01

    In the iscom, multiple copies of antigen are attached by hydrophobic interaction to a matrix which is built up by Quillaja triterpenoid saponins and lipids. Thus, the iscom presents antigen in multimeric form in a small particle with a built-in adjuvant resulting in a highly immunogenic antigen formulation. We have designed a chloroform-methanol-water extraction procedure to isolate the triterpenoid saponins and lipids incorporated into iscom-matrix and iscoms. The triterpenoids in the triterpenoid phase were quantitated using orcinol sulfuric acid detecting their carbohydrate chains and by HPLC. The cholesterol and phosphatidylcholine in the lipid phase were quantitated by HPLC and a commercial colorimetric method for the cholesterol. The quantitative methods showed an almost total separation and recovery of triterpenoids and lipids in their respective phases, while protein was detected in all phases after extraction. The protein content was determined by the method of Lowry and by amino acid analysis. Amino acid analysis was shown to be the reliable method of the two to quantitate proteins in iscoms. In conclusion, simple, reproducible and efficient procedures have been designed to isolate and quantitate the triterpenoids and lipids added for preparation of iscom-matrix and iscoms. The procedures described should also be useful to adequately define constituents in prospective vaccines.

  11. Synthesis of arborane triterpenols by a bacterial oxidosqualene cyclase

    Science.gov (United States)

    Banta, Amy B.; Wei, Jeremy H.; Gill, Clare C. C.; Giner, José-Luis; Welander, Paula V.

    2017-01-01

    Cyclic triterpenoids are a broad class of polycyclic lipids produced by bacteria and eukaryotes. They are biologically relevant for their roles in cellular physiology, including membrane structure and function, and biochemically relevant for their exquisite enzymatic cyclization mechanism. Cyclic triterpenoids are also geobiologically significant as they are readily preserved in sediments and are used as biomarkers for ancient life throughout Earth's history. Isoarborinol is one such triterpenoid whose only known biological sources are certain angiosperms and whose diagenetic derivatives (arboranes) are often used as indicators of terrestrial input into aquatic environments. However, the occurrence of arborane biomarkers in Permian and Triassic sediments, which predates the accepted origin of angiosperms, suggests that microbial sources of these lipids may also exist. In this study, we identify two isoarborinol-like lipids, eudoraenol and adriaticol, produced by the aerobic marine heterotrophic bacterium Eudoraea adriatica. Phylogenetic analysis demonstrates that the E. adriatica eudoraenol synthase is an oxidosqualene cyclase homologous to bacterial lanosterol synthases and distinct from plant triterpenoid synthases. Using an Escherichia coli heterologous sterol expression system, we demonstrate that substitution of four amino acid residues in a bacterial lanosterol synthase enabled synthesis of pentacyclic arborinols in addition to tetracyclic sterols. This variant provides valuable mechanistic insight into triterpenoid synthesis and reveals diagnostic amino acid residues to differentiate between sterol and arborinol synthases in genomic and metagenomic datasets. Our data suggest that there may be additional bacterial arborinol producers in marine and freshwater environments that could expand our understanding of these geologically informative lipids.

  12. Composition of the epicuticular and intracuticular wax layers on Kalanchoe daigremontiana (Hamet et Perr. de la Bathie) leaves.

    Science.gov (United States)

    van Maarseveen, Clare; Jetter, Reinhard

    2009-05-01

    Epicuticular and intracuticular waxes from both adaxial and abaxial surfaces of the leaves of Kalanchoe daigremontiana were analyzed. All wax mixtures were found to contain approximately equal amounts of triterpenoids and very long chain fatty acid (VLCFA) derivatives. The triterpenoid fraction consisted of glutinol (8-19% of the total wax) and friedelin (4-9%), together with smaller amounts of glutanol, glutinol acetate, epifriedelanol, germanicol and beta-amyrin. The VLCFA derivatives comprised C27-C35 alkanes (19-37% of the total wax), C32-C34 aldehydes (3-7%), C32 and C34 fatty acids (0.2-3%), C26-C36 primary alcohols (4-8%), and C42-C52 alkyl esters (2-9%). The wax layers were found to differ in triterpenoid amounts, with the intracuticular wax containing higher percentages of most triterpenoids than the epicuticular wax. Friedelin, the only triterpenoid ketone present, showed the opposite distribution with higher proportions in the epicuticular wax. VLCFA derivatives also accumulated to higher percentages in the epicuticular than in the intracuticular wax layer. Epicuticular wax crystals were observed on both the adaxial and abaxial leaf surfaces.

  13. Chemical constituents of Salacia elliptica (Celastraceae)

    International Nuclear Information System (INIS)

    Duarte, Lucienir Pains; Figueiredo, Rute Cunha; Sousa, Grasiely Faria de; Soares, Debora Barbosa da Silva; Rodrigues, Salomao Bento Vasconcelos; Silva, Fernando Cesar; Silva, Gracia Divina de Fatima; Vieira Filho, Sidney Augusto

    2010-01-01

    The chemical investigation of Salacia elliptica allowed to the isolation of 20 constituents: two polyols, one xanthone, a mixture of long chain hydrocarbons, one carboxylic acid, one polymer, two steroidal compounds, one aromatic ester and eleven pentacyclic triterpenes. These triterpenes include 3β-stearyloxy-oleanane, 3β-stearyloxy-ursane, one seco-friedelane, and eight compounds of the friedelane series. The chemical structure and the relative configuration of a new triterpene 1,3-dioxo-16α-hydroxyfriedelane (15) were established through 1 H and 13 C NMR including 2D experiments (HMBC, HMQC, COSY and NOESY) and herein reported for the first time (author)

  14. Chemical constituents of Salacia elliptica (Celastraceae)

    Energy Technology Data Exchange (ETDEWEB)

    Duarte, Lucienir Pains; Figueiredo, Rute Cunha; Sousa, Grasiely Faria de; Soares, Debora Barbosa da Silva; Rodrigues, Salomao Bento Vasconcelos; Silva, Fernando Cesar; Silva, Gracia Divina de Fatima, E-mail: lucienir@ufmg.b [Universidade Federal de Minas Gerais (UFMG), Belo Horizonte, MG (Brazil). Dept. de Quimica; Vieira Filho, Sidney Augusto [Universidade Federal de Ouro Preto, MG (Brazil). Escola de Farmacia. Dept. de Farmacia

    2010-07-01

    The chemical investigation of Salacia elliptica allowed to the isolation of 20 constituents: two polyols, one xanthone, a mixture of long chain hydrocarbons, one carboxylic acid, one polymer, two steroidal compounds, one aromatic ester and eleven pentacyclic triterpenes. These triterpenes include 3{beta}-stearyloxy-oleanane, 3{beta}-stearyloxy-ursane, one seco-friedelane, and eight compounds of the friedelane series. The chemical structure and the relative configuration of a new triterpene 1,3-dioxo-16alpha-hydroxyfriedelane (15) were established through {sup 1}H and {sup 13}C NMR including 2D experiments (HMBC, HMQC, COSY and NOESY) and herein reported for the first time (author)

  15. Chemical constituents of Salacia elliptica (Celastraceae

    Directory of Open Access Journals (Sweden)

    Lucienir Pains Duarte

    2010-01-01

    Full Text Available The chemical investigation of Salacia elliptica allowed to the isolation of 20 constituents: two polyols, one xanthone, a mixture of long chain hydrocarbons, one carboxylic acid, one polymer, two steroidal compounds, one aromatic ester and eleven pentacyclic triterpenes. These triterpenes include 3β-stearyloxy-oleanane, 3β-stearyloxy-ursane, one seco-friedelane, and eight compounds of the friedelane serie. The chemical structure and the relative configuration of a new triterpene 1,3-dioxo-16α-hydroxyfriedelane (15 were established through ¹H and 13C NMR including 2D experiments (HMBC, HMQC, COSY and NOESY and herein reported for the first time.

  16. [Effective productions of plant secondary metabolites having antitumor activity by plant cell and tissue cultures].

    Science.gov (United States)

    Taniguchi, Shoko

    2005-06-01

    Methods for the effective production of plant secondary metabolites with antitumor activity using plant cell and tissue cultures were developed. The factors in tannin productivity were investigated using culture strains producing different types of hydrolyzable tannins, i.e., gallotannins (mixture of galloylglucoses), ellagi-, and dehydroellagitannins. Production of ellagi- and dehydroellagitannins was affected by the concentrations and ratio of nitrogen sources in the medium. The formation of oligomeric ellagitannins in shoots of Oenothera tetraptera was correlated with the differentiation of tissues. Cultured cells of Eriobotrya japonica producing ursane- and oleanane-type triterpenes with antitumor activities were also established.

  17. Fungi & Health: can polysaccharides from the fungus inonotus obliquus (CHAGA) inhibit tumor growth?

    DEFF Research Database (Denmark)

    Wold, C. W.; Corthay, A.; Kjeldsen, Christian

    Inonotus obliquus (Chaga) – a white rot fungus found on birch trees in the northern hemisphere –has been used in traditional medicine in Europe and Asia for centuries. Native peoples have made use of Chaga by brewing it as a tea to treat gastro-intestinal problems, to heal wounds and even to treat...... cancer. The last few decades, studies have found Chaga to contain biologically active substances such as polysaccharides, triterpenoids, polyphenols and melanin. In vivo effects such as tumor growth inhibition have been observed in mice receiving various Chaga extracts. The main hypothesis behind...... the tumor inhibiting effect is two-fold: i) fungal polysaccharides may inhibit tumor growth indirectly by activating certain immune cells such as macrophages and ii) triterpenoids and other steroids from Chaga may give a direct cytotoxic effect against cancer cells. While triterpenoids from Chaga have been...

  18. Cloning and Characterization of Oxidosqualene Cyclases from Kalanchoe daigremontiana

    Science.gov (United States)

    Wang, Zhonghua; Yeats, Trevor; Han, Hong; Jetter, Reinhard

    2010-01-01

    The first committed step in triterpenoid biosynthesis is the cyclization of oxidosqualene to polycyclic alcohols or ketones C30H50O. It is catalyzed by single oxidosqualene cyclase (OSC) enzymes that can carry out varying numbers of carbocation rearrangements and, thus, generate triterpenoids with diverse carbon skeletons. OSCs from diverse plant species have been cloned and characterized, the large majority of them catalyzing relatively few rearrangement steps. It was recently predicted that special OSCs must exist that can form friedelin, the pentacyclic triterpenoid whose formation involves the maximum possible number of rearrangement steps. The goal of the present study, therefore, was to clone a friedelin synthase from Kalanchoe daigremontiana, a plant species known to accumulate this triterpenoid in its leaf surface waxes. Five OSC cDNAs were isolated, encoding proteins with 761–779 amino acids and sharing between 57.4 and 94.3% nucleotide sequence identity. Heterologous expression in yeast and GC-MS analyses showed that one of the OSCs generated the steroid cycloartenol together with minor side products, whereas the other four enzymes produced mixtures of pentacyclic triterpenoids dominated by lupeol (93%), taraxerol (60%), glutinol (66%), and friedelin (71%), respectively. The cycloartenol synthase was found expressed in all leaf tissues, whereas the lupeol, taraxerol, glutinol, and friedelin synthases were expressed only in the epidermis layers lining the upper and lower surfaces of the leaf blade. It is concluded that the function of these enzymes is to form respective triterpenoid aglycones destined to coat the leaf exterior, probably as defense compounds against pathogens or herbivores. PMID:20610397

  19. 15N-labelled pyrazines of triterpenic acids

    International Nuclear Information System (INIS)

    Vlk, Martin; Micolova, Petra; Sarek, Jan

    2016-01-01

    Triterpenoid pyrazines from our research group were found selectively cytotoxic on several cancer cell lines with IC 50 in low micromolar range. This sparked our interest in preparing their labeled analogs for metabolic studies. In this work, we prepared a set of non-labeled pyrazines from seven triterpenoid skeletal types along with their 15 N labelled analogs. In this work, we present the synthesis and characterization of the target 15 N labelled pyrazines. Currently, these compounds are being studied in complex metabolic studies. (author)

  20. Terpenoids from Tripterygium doianum (Celastraceae).

    Science.gov (United States)

    Tanaka, Naonobu; Duan, Hongquan; Takaishi, Yoshihisa; Kawazoe, Kazuyoshi; Goto, Satoru

    2002-09-01

    The extract of Tripterygium doianum (Celastraceae) afforded three triterpenoids [3beta-acetoxy-11-ursen-13alpha,30-olide, 25-chloro-24-hydroxytirucall-7-en-3-one and tirucall-7-en-3,24-dione], two sesquiterpenoids [5alpha-acetoxy-1beta,8alpha-bis-cinnamoyl-4alpha-hydroxydihydroagarofuran and 5alpha-acetoxy-1beta-benzoyl-8alpha-cinnamoyl-4alpha-hydroxydihydroagarofuran] and nine known triterpenoids. Their structures were established based on spectroscopic studies. Copyright 2002 Elsevier Science Ltd.

  1. Application of a controllable degron strategy for metabolic engineering

    DEFF Research Database (Denmark)

    Knuf, Christoph; Maury, Jerome; Jacobsen, Simo Abdessamad

    2014-01-01

    In numerous cases of metabolic engineering, metabolite pools have to be increased in order to obtain flux into heterologous pathways. A simple tool for this would be the deletion of genes that would practically lead to a block of the natural pathway, so that the carbon can flow into the heterolog...... of intermediates of the mevalonate pathway around 2,3-oxidosqualene, which is the precursor for triterpenoids. Many triterpenoids are pharmaceutically relevant compounds which nowadays need to be extracted from plant material through an intricate and resource consuming process....

  2. Combinatorial biosynthesis of sapogenins and saponins in Saccharomyces cerevisiae using a C-16α hydroxylase from Bupleurum falcatum

    Science.gov (United States)

    Moses, Tessa; Pollier, Jacob; Almagro, Lorena; Buyst, Dieter; Van Montagu, Marc; Pedreño, María A.; Martins, José C.; Thevelein, Johan M.; Goossens, Alain

    2014-01-01

    The saikosaponins comprise oleanane- and ursane-type triterpene saponins that are abundantly present in the roots of the genus Bupleurum widely used in Asian traditional medicine. Here we identified a gene, designated CYP716Y1, encoding a cytochrome P450 monooxygenase from Bupleurum falcatum that catalyzes the C-16α hydroxylation of oleanane- and ursane-type triterpenes. Exploiting this hitherto unavailable enzymatic activity, we launched a combinatorial synthetic biology program in which we combined CYP716Y1 with oxidosqualene cyclase, P450, and glycosyltransferase genes available from other plant species and reconstituted the synthesis of monoglycosylated saponins in yeast. Additionally, we established a culturing strategy in which applying methylated β-cyclodextrin to the culture medium allows the sequestration of heterologous nonvolatile hydrophobic terpenes, such as triterpene sapogenins, from engineered yeast cells into the growth medium, thereby greatly enhancing productivity. Together, our findings provide a sound base for the development of a synthetic biology platform for the production of bioactive triterpene sapo(ge)nins. PMID:24434554

  3. Saponins from Cephalaria aristata C. Koch

    Directory of Open Access Journals (Sweden)

    Derya Gülcemal

    2014-05-01

    Full Text Available One new oleanane-type saponin, 3-O-β-D-glucopyranosyl-(1→4-β-D-xylopyranosyl-(1→3-α-L-rhamnopyranosyl-(1→2-α-L-arabinopyranosyl hederagenin 28-O-β-D-glucopyranosyl-(1→6-β-D-glucopyranosyl ester (1 was isolated from the MeOH extract of whole plant parts of Cephalaria aristata C. Koch along with three known oleanane-type saponins (2-4, 3-O- α -L-rhamnopyranosyl-(1→2- α -L-arabinopyranosyl hederagenin 28-O-( β -D-glucopyranosyl-(1→6- β -D-glucopyranosyl ester, 3-O- β -D-glucopyranosyl-(1→4- β -D-xylopyranosyl-(1→3- α -L-rhamnopyranosyl-(1→2- α -L-arabinopyranosyl hederagenin and 3-O- α -L-rhamnopyranosyl-(1→2- α -L-arabinopyranosyl hederagenin respectively, (5-7, oleanolic acid (5, β -amyrin (6 and 20 β -hydroxyursolic acid (7 and one sterol glucoside (8, 29-hydroxystigmast-5-en-3-O- β -D-glucopyranosyde. Their structures were established by the extensive use of 1D- and 2D-NMR experiments along with ESIMS and HRMS analysis.

  4. New triterpenic acids from Uncaria rhynchophylla: chemistry, NO-inhibitory activity, and tandem mass spectrometric analysis.

    Science.gov (United States)

    Zhang, Yi-bei; Yang, Wen-zhi; Yao, Chang-liang; Feng, Rui-hong; Yang, Min; Guo, De-an; Wu, Wan-ying

    2014-07-01

    Five new oleanane and ursane type triterpenes, namely uncarinic acids F-J (1-5), together with six known triterpenic acids (6-11) were isolated from the stems and hooks of Uncaria rhynchophylla. Structure elucidation of 1-5 was based on the integrated analyses of high-resolution MS data, 1D ((1)H NMR, (13)C NMR, DEPT) and 2D (HSQC, HMBC, ROESY) NMR spectra. Compounds 4, 10, and 11 exhibited weak inhibitory effects on LPS-induced NO production in RAW264.7 cells (with IC50 1.48, 7.01, and 1.89 μM, respectively) with dexamethasone (IC50 0.04 μM) and quercetin (IC50 0.86 μM) as the positive controls. 19-OH substituted oleanane triterpenic acids (1, 2, 5, 8) were prone to eliminate CH2O3, whereas those ursane-type encompassing 19-OH (3, 6, 7, 9, 4) were featured by preferred cleavage of H2O while performing the negative collision-induced MS/MS fragmentation on an LTQ/Orbitrap mass spectrometer. Copyright © 2014 Elsevier B.V. All rights reserved.

  5. Modulating the level of components within plants

    Science.gov (United States)

    Bobzin, Steven Craig; Apuya, Nestor; Chiang, Karen; Doukhanina, Elena; Feldmann, Kenneth; Jankowski, Boris; Margolles-Clark, Emilio; Mumenthaler, Daniel; Okamuro, Jack; Park, Joon-Hyun; Van Fleet, Jennifer E.; Zhang, Ke

    2017-09-12

    Materials and Methods for identifying lignin regulatory region-regulatory protein associations are disclosed. Materials and methods for modulating lignin accumulation are also disclosed. In addition, methods and materials for modulating (e.g., increasing or decreasing) the level of a component (e.g., protein, oil, lignin, carbon, a carotenoid, or a triterpenoid) in plants are disclosed.

  6. A comparative study of lipids in Sphagnum species

    NARCIS (Netherlands)

    Sinninghe Damsté, J.S.; Baas, M.; Pancost, R.D.; Geel, B. van

    2000-01-01

    The free lipid compositions of twelve species of Sphagnum were determined by capillary gas chromatography/mass spectrometry as part of a study to identify characteristic lipids for Sphagnum in peat bogs. Complex mixtures of lipids, comprised of C28 C29 sterols, C30 triterpenoids, C16 C30 fatty

  7. Hydrocarbons and energy from plants: Final report, 1984-1987

    Energy Technology Data Exchange (ETDEWEB)

    Calvin, M.; Otvos, J.; Taylor, S.E.; Nemethy, E.K.; Skrukrud, C.L.; Hawkins, D.R.; Lago, R.

    1988-08-01

    Plant hydrocarbon (isoprenoid) production was investigated as an alternative source to fossil fuels. Because of their high triterpenoid (hydrocarbon) content of 4--8%, Euphorbia lathyris plants were used as a model system for this study. The structure of the E. lathyris triterpenoids was determined, and triterpenoid biosynthesis studied to better understand the metabolic regulation of isoprenoid production. Triterpenoid biosynthesis occurs in two distinct tissue types in E. lathyris plants: in the latex of the laticifer cells; and in the mesophyll cells of the leaf and stem. The latex has been fractionated by centrifugation, and it has been determined that the later steps of isoprenoid biosynthesis, the conversion of mevalonic acid to the triterpenes, are compartmentized within a vacuole. Also identified was the conversion of hydroxymethyl glutaryl-CoA to mevalonic acid, catalyzed by the enzyme Hydroxymethyl glutaryl-CoA Reductase, as a key rate limiting step in isoprenoid biosynthesis. At least two isozymes of this enzyme, one in the latex and another in the leaf plastids, have been identified. Environmental stress has been applied to plants to study changes in carbon allocation. Salinity stress caused a large decrease in growth, smaller decreases in photosynthesis, resulting in a larger allocation of carbon to both hydrocarbon and sugar production. An increase in Hydroxymethyl glutaryl-CoA Reductase activity was also observed when isoprenoid production increased. Other species where also screened for the production of hydrogen rich products such as isoprenoids and glycerides, and their hydrocarbon composition was determined.

  8. 13C nuclear magnetic resonance data of lanosterol derivatives—Profiling the steric topology of the steroid skeleton via substituent effects on its 13C NMR

    Science.gov (United States)

    Dias, Jerry Ray; Gao, Hongwu

    2009-12-01

    The 13C NMR spectra of over 24 tetracyclic triterpenoid derivatives have been structurally analyzed. The 13C NMR chemical shifts allow one to probe the steric topology of the rigid steroid skeleton and inductive effects of its substituents. Use of deuterium labeling in chemical shift assignment and B-ring aromatic terpenoids are also featured.

  9. The effect of porcine somatotropin (pST) and gender on production ...

    African Journals Online (AJOL)

    The effect of porcine somatotropin (pST) and gender on production parameters and tissue yield of pigs slaughtered at 135 kg live weight. ... No significant pST effects were found for live weight, carcass weight, % bone, % fat or % lean meat, but a significant increase in percentage skin was found. Keywords: triterpenoid, stem ...

  10. Ultraviolet spectroscopic evaluation of bioactive saponin fraction ...

    African Journals Online (AJOL)

    This study was to evaluate and characterize the saponin principles, using chromatographic and ..... triterpenoids, reducing sugars, amino acids, flavonoids, ..... blood glucose levels of diabetic rats. Int. J. Biol. Chem. ... homeostatic plants in Edo and Delta. States of ... mellitus: Systematic review and meta- analysis. BMJ,.

  11. The protection of glycyrrhetinic acid (GA) towards acetaminophen ...

    African Journals Online (AJOL)

    piratory tract infections, asthma, pneumothorax, chron- ic obstructive pulmonary disease, pulmonary fibrosis, tuberculosis, and even cancers1,2. Searching effective drugs for respiratory system diseases is very important. Glycyrrhetinic acid, also called as enoxolone, is a pen- tacyclic triterpenoid derivative of the beta-amyrin ...

  12. Soy Saponins: Current Research and Future Goals

    Science.gov (United States)

    Saponins are a biologically active class of triterpenoid phytochemicals found in soybeans at concentrations similar to those of the isoflavones, and the role they may play in nutrition and health is not well understood. Research the functionality of these compounds in animals and humans has been ha...

  13. Verbesinosides A-F, Novel 15,27-Cyclooleanane Saponins from the American Native Plant Verbesina virginica

    Science.gov (United States)

    Verbesinosides A-F (1-6), six novel 15,27-cyclooleanane-type triterpenoid saponins carrying different aromatic acyl moieties on the aglycone, were isolated from the leaf and flower of Verbesina virginica. Their structures were established by interpretation of spectroscopic data and chemical methods....

  14. Environ: E00205 [KEGG MEDICUS

    Lifescience Database Archive (English)

    Full Text Available enoid [CPD:C06085], Friedelin [CPD:C08626], Shionone, Triterpenoid saponin, Astersaponin, Quercetin [CPD:C00...389], Prosapogenin, epi-Friedelanol [CPD:C17123], Lachnophyllol [CPD:C17965], Anethole [CPD:C10428], Lachnophyllol acetate, Astersapo...nin, Essential oil Aster tataricus [TAX:588669] Same as:

  15. Surface Shear Rheology of Saponin Adsorption Layers

    NARCIS (Netherlands)

    Golemanov, K.; Tcholakova, S.; Denkov, N.; Pelan, E.; Stoyanov, S.D.

    2012-01-01

    Saponins are a wide class of natural surfactants, with molecules containing a rigid hydrophobic group (triterpenoid or steroid), connected via glycoside bonds to hydrophilic oligosaccharide chains. These surfactants are very good foam stabiliziers and emulsifiers, and show a range of nontrivial

  16. QUAFRINOIC ACIDS: TWO NEW TRITERPENIODS FROM ...

    African Journals Online (AJOL)

    From the stem bark of Quassia africana, two new triterpenoids with the ursolic acid skeleton, characterized as 3-oxo-urs-12-en-27a, 28di-oic acid and its dihydro derivative, 3β-urs-12-en-27α, 28di-oic acid have been isolated. The structures were determined using spectroscopic techniques. KEY WORDS: Quassia africana; ...

  17. Rosemary, the beneficial chemistry of a garden herb.

    Science.gov (United States)

    Hanson, James R

    2016-01-01

    The major natural products that are present in the garden herb, rosemary (Rosmarinus officinalis) including the mono di- and triterpenoid, flavonoid and phenolic constituents together with their biological activity as anti-microbial, anti-oxidant, anti-inflammatory, memory-enhancing and tumour-inhibitory agents, are reviewed.

  18. Author Details

    African Journals Online (AJOL)

    Zhang, Xiaoqi. Vol 15, No 2 (2016) - Articles Ameliorative Effect and Underlying Mechanisms of Total Triterpenoids from Psidium guajava Linn (Myrtaceae) Leaf on High-Fat Streptozotocin-induced Diabetic Peripheral Neuropathy in Rats Abstract PDF. ISSN: 1596-9827. AJOL African Journals Online. HOW TO USE AJOL.

  19. Des-A-lupane in an East African lake sedimentary record as a new proxy for the stable carbon isotopic composition of C3 plants

    NARCIS (Netherlands)

    van Bree, Loes G.J.; Rijpstra, W. Irene C; Al-Dhabi, N.A.; Verschuren, D.; Sinninghe Damste, J.S.; de Leeuw, J.W.

    2016-01-01

    We studied the high-resolution and well-dated 25,000 year sedimentary record of Lake Challa, a deep tropical crater lake in equatorial East Africa, to explore new proxies for paleoenvironmental and paleohydrological change. Sedimentary biomarker analysis revealed the presence of des-A-triterpenoids

  20. Bauer-7-en-3{beta}-yl acetate: a major constituent of unusual samples of Brazilian propolis

    Energy Technology Data Exchange (ETDEWEB)

    Teixeira, Erica Weinstein [Secretaria da Agricultura e Abastecimento, Pindamonhangaba, SP (Brazil). Agencia Paulista de Tecnologia dos Agronegocios; Message, Dejair [Vicosa Univ., MG (Brazil). Inst. de Biociencias. Dept. de Biologia Animal; Negri, Giuseppina; Salatino, Antonio [Sao Paulo Univ., SP (Brazil). Dept. de Botanica

    2006-03-15

    The pentacyclic triterpenoid bauer-7-en-3{beta}-yl acetate was obtained from thloroform extract of an unusual sample of propolis from southeast Brazil with the yield of 7%. The compound was identified by comparison of IR, MS and NMR analysis with published data. (author)

  1. Pramana – Journal of Physics | Indian Academy of Sciences

    Indian Academy of Sciences (India)

    The nanosized triterpenoid, arjunolic acid, showed efficient gelation of various organic solvents at low concentrations. The low molecular mass gelator molecules self-assembled in the solvents to form fibers of nanometer diameters. The movement of the solvent molecules was hindered inside the fibrous network leading to ...

  2. Betulinic acid-induced mitochondria-dependent cell death is counterbalanced by an autophagic salvage response

    NARCIS (Netherlands)

    Potze, L.; Mullauer, F. B.; Colak, S.; Kessler, J. H.; Medema, J. P.

    2014-01-01

    Betulinic acid (BetA) is a plant-derived pentacyclic triterpenoid that exerts potent anti-cancer effects in vitro and in vivo. It was shown to induce apoptosis via a direct effect on mitochondria. This is largely independent of proapoptotic BAK and BAX, but can be inhibited by cyclosporin A (CsA),

  3. Comparative Studies of Some Polypores Using High Performance ...

    African Journals Online (AJOL)

    ... these polypores in a previous work. The ability of the polypores to produce triterpenoids is affected by their age, period of collection, geographical location and method of drying, which also affected the High Performance Liquid Chromatography characteristics of their secondary metabolites. African Research Review Vol.

  4. Subcritical water extraction of bioactive compounds from dry loquat ...

    African Journals Online (AJOL)

    ERASTO

    total flavonoids (54.1 ± 4.1 mgQE/g LW) and total triterpenoids (37.5 ± 3.2 mgUAE/g LW) ... those obtained using traditional extraction methods, and their main structural pattern of the cured .... Quantification was based on the standard curve generated ..... HPLC chromatograms of the triterpene acids from loquat leaf extract.

  5. In vitro antimicrobial activity of Harungana madagascriensis and ...

    African Journals Online (AJOL)

    Phytochemical analysis showed the presence of phenols, tannins, saponins, anthraquinones, anthocyanins, triterpenoids, flavonoids and alkaloids in both plant extracts. These data suggest that the aqueous extracts of H. madagascariensis and E. prostrata contain antibacterial principles which may be non toxic. Keywords: ...

  6. Biosynthesis, regulation, and domestication of bitterness in cucumber

    NARCIS (Netherlands)

    Shang, Y.; Ma, Y.; Bouwmeester, H.J.

    2014-01-01

    Cucurbitacins are triterpenoids that confer a bitter taste in cucurbits such as cucumber, melon, watermelon, squash, and pumpkin. These compounds discourage most pests on the plant and have also been shown to have antitumor properties. With genomics and biochemistry, we identified nine cucumber

  7. Growth inhibitory, apoptotic and anti-inflammatory activities ...

    Indian Academy of Sciences (India)

    naturally abundant oleanolic acid, displayed diverse biolog- ical activities ... triterpenoids and natural products. CDDO and its .... ration was determined by treating with anti-BrdU antibody and Texas red ..... apoptotic and necrotic in the tumour tissue. Thus .... Palmer RM, Ashton DS and Moncada S 1988 Vascular endothelial.

  8. Control of water-borne parasitic diseases with natural products: the potential of Dialium guineense as a molluscicide.

    Science.gov (United States)

    Houghton, P J; Odukoya, O A; Adelusi, A; Omogbai, E K; Sanderson, L; Whitfield, P J

    1997-01-01

    The molluscicidal activity of the fruit and leaves of Dialium guineense was found to be due to glycosides of the triterpenoid oleanolic acid. Three glycosides were isolated from the fruit and a fourth from the leaves and are known compounds. The amount of total saponins present in D. guineense makes it a good candidate for a readily available molluscicide in Nigerian villages.

  9. Role of cucurbitacin C in resistance to spider mite (Tetranychus urticae) in cucumber (Cucumber sativus L.)

    NARCIS (Netherlands)

    Balkema-Boomstra, A.G.; Zijlstra, S.; Verstappen, F.W.A.; Inggamer, H.; Mercke, P.

    2003-01-01

    Cucurbitacins are bitter triterpenoid compounds that are toxic to most organisms and occur widely in wild and cultivated Cucurbitaceae. The only cucurbitacin identified in Cucumis sativus is cucurbitacin C. The bitter taste of cucumber has been correlated with resistance to the spider mite

  10. Terpenoid biosynthesis in Euphorbia lathyris and Copaifera spp

    International Nuclear Information System (INIS)

    Skrukrud, C.L.

    1987-07-01

    Biosynthesis of triterpenoids by isolated latex of Euphorbia lathyris was investigated. The rate of in vitro incorporation of mevalonic acid into triterpenoids was thirty times greater than acetate incorporation indicating that the rate-limiting step in the pathway occurs prior to mevalonate. Both HMG-CoA reductase (EC 1.1.1.34) and HMG-CoA lyase (EC 4.1.3.4) activities were detected in isolated latex. HMG-CoA reductase was localized to a membrane-bound fraction of a 5000g pellet of latex. The rate of conversion of HMG-CoA to mevalonate by this enzyme is comparable to the overall rate of acetate incorporation into the triterpenoids suggesting that this enzyme is rate-determining in the biosynthesis of triterpenoids in E. lathyris latex. HMG-CoA reductase of E. lathyris vegetative tissue was localized to the membrane-bound portion of a particulate fraction (18,000g), and was solubilized by treatment with 2% polyoxyethylene ether W-1. Differences in the optimal pH for activity of HMG-CoA reductase from the latex and vegetative tissue suggest that isozymes of the enzyme may be present in the two tissue types. Studies of the incorporation of various precursors into leaf discs and cuttings taken from Copaifera spp. show differences in the rate of incorporation into Copaifera sesquiterpenes suggesting that the site of sesquiterpene biosynthesis may differ in its accessibility to the different substrates and/or reflecting the metabolic controls on carbon allocation to the terpenes. Mevalonate incorporation by Copaifera langsdorfii cuttings into sesquiterpenes was a hundred-fold greater than either acetate or glucose incorporation, however, its incorporation into squalene and triterpenoids was also a hundred-fold greater than the incorporation into sesquiterpenes. 119 refs., 58 figs., 16 tabs

  11. The Application of Ultra-High-Performance Liquid Chromatography Coupled with a LTQ-Orbitrap Mass Technique to Reveal the Dynamic Accumulation of Secondary Metabolites in Licorice under ABA Stress.

    Science.gov (United States)

    Li, Da; Xu, Guojie; Ren, Guangxi; Sun, Yufeng; Huang, Ying; Liu, Chunsheng

    2017-10-20

    The traditional medicine licorice is the most widely consumed herbal product in the world. Although much research work on studying the changes in the active compounds of licorice has been reported, there are still many areas, such as the dynamic accumulation of secondary metabolites in licorice, that need to be further studied. In this study, the secondary metabolites from licorice under two different methods of stress were investigated by ultra-high-performance liquid chromatography coupled with hybrid linear ion trap-Orbitrap mass spectrometry (UHPLC-LTQ-Orbitrap-MS). A complex continuous coordination of flavonoids and triterpenoids in a network was modulated by different methods of stress during growth. The results showed that a total of 51 secondary metabolites were identified in licorice under ABA stress. The partial least squares-discriminate analysis (PLS-DA) revealed the distinction of obvious compounds among stress-specific districts relative to ABA stress. The targeted results showed that there were significant differences in the accumulation patterns of the deeply targeted 41 flavonoids and 10 triterpenoids compounds by PCA and PLS-DA analyses. To survey the effects of flavonoid and triterpenoid metabolism under ABA stress, we inspected the stress-specific metabolic changes. Our study testified that the majority of flavonoids and triterpenoids were elevated in licorice under ABA stress, while the signature metabolite affecting the dynamic accumulation of secondary metabolites was detected. Taken together, our results suggest that ABA-specific metabolite profiling dynamically changed in terms of the biosynthesis of flavonoids and triterpenoids, which may offer new trains of thought on the regular pattern of dynamic accumulation of secondary metabolites in licorice at the metabolite level. Our results also provide a reference for clinical applications and directional planting and licorice breeding.

  12. Terpenoid biosynthesis in Euphorbia lathyris and Copaifera spp

    Energy Technology Data Exchange (ETDEWEB)

    Skrukrud, C.L.

    1987-07-01

    Biosynthesis of triterpenoids by isolated latex of Euphorbia lathyris was investigated. The rate of in vitro incorporation of mevalonic acid into triterpenoids was thirty times greater than acetate incorporation indicating that the rate-limiting step in the pathway occurs prior to mevalonate. Both HMG-CoA reductase (EC 1.1.1.34) and HMG-CoA lyase (EC 4.1.3.4) activities were detected in isolated latex. HMG-CoA reductase was localized to a membrane-bound fraction of a 5000g pellet of latex. The rate of conversion of HMG-CoA to mevalonate by this enzyme is comparable to the overall rate of acetate incorporation into the triterpenoids suggesting that this enzyme is rate-determining in the biosynthesis of triterpenoids in E. lathyris latex. HMG-CoA reductase of E. lathyris vegetative tissue was localized to the membrane-bound portion of a particulate fraction (18,000g), and was solubilized by treatment with 2% polyoxyethylene ether W-1. Differences in the optimal pH for activity of HMG-CoA reductase from the latex and vegetative tissue suggest that isozymes of the enzyme may be present in the two tissue types. Studies of the incorporation of various precursors into leaf discs and cuttings taken from Copaifera spp. show differences in the rate of incorporation into Copaifera sesquiterpenes suggesting that the site of sesquiterpene biosynthesis may differ in its accessibility to the different substrates and/or reflecting the metabolic controls on carbon allocation to the terpenes. Mevalonate incorporation by Copaifera langsdorfii cuttings into sesquiterpenes was a hundred-fold greater than either acetate or glucose incorporation, however, its incorporation into squalene and triterpenoids was also a hundred-fold greater than the incorporation into sesquiterpenes. 119 refs., 58 figs., 16 tabs.

  13. The Application of Ultra-High-Performance Liquid Chromatography Coupled with a LTQ-Orbitrap Mass Technique to Reveal the Dynamic Accumulation of Secondary Metabolites in Licorice under ABA Stress

    Directory of Open Access Journals (Sweden)

    Da Li

    2017-10-01

    Full Text Available The traditional medicine licorice is the most widely consumed herbal product in the world. Although much research work on studying the changes in the active compounds of licorice has been reported, there are still many areas, such as the dynamic accumulation of secondary metabolites in licorice, that need to be further studied. In this study, the secondary metabolites from licorice under two different methods of stress were investigated by ultra-high-performance liquid chromatography coupled with hybrid linear ion trap–Orbitrap mass spectrometry (UHPLC-LTQ-Orbitrap-MS. A complex continuous coordination of flavonoids and triterpenoids in a network was modulated by different methods of stress during growth. The results showed that a total of 51 secondary metabolites were identified in licorice under ABA stress. The partial least squares–discriminate analysis (PLS-DA revealed the distinction of obvious compounds among stress-specific districts relative to ABA stress. The targeted results showed that there were significant differences in the accumulation patterns of the deeply targeted 41 flavonoids and 10 triterpenoids compounds by PCA and PLS-DA analyses. To survey the effects of flavonoid and triterpenoid metabolism under ABA stress, we inspected the stress-specific metabolic changes. Our study testified that the majority of flavonoids and triterpenoids were elevated in licorice under ABA stress, while the signature metabolite affecting the dynamic accumulation of secondary metabolites was detected. Taken together, our results suggest that ABA-specific metabolite profiling dynamically changed in terms of the biosynthesis of flavonoids and triterpenoids, which may offer new trains of thought on the regular pattern of dynamic accumulation of secondary metabolites in licorice at the metabolite level. Our results also provide a reference for clinical applications and directional planting and licorice breeding.

  14. Chemical constituents from Aspidosperma illustre (Apocynaceae)

    International Nuclear Information System (INIS)

    Barbosa, Lara F.; Mathias, Leda; Braz-Filho, Raimundo; Vieira, Ivo J. Curcino

    2010-01-01

    A new natural product oleanane-type triterpene, olean-12-ene-11α-methoxy-3β-acetate (10) was isolated from Aspidosperma illustre, together with β-amyrin (3), lupeol (4), β-amyrin acetate (5), lupeol acetate (6), olean-12-ene-28-hydroxy-3α-tetradecanoate (7), olean-12-ene-28-carboxy-3α-hexadecanoate (8), ursolic acid (9) triterpenes, and two monoterpenic indole alkaloids, b-yoimbine (1) and 1,2-dehydroaspidospermidine (2). These compounds were characterized on their spectral data basis, mainly one- ( 1 H, 13 C, APT) and two-dimensional ( 1 H- 1 H-COSY, 1 H- 1 HNOESY, HMQC and HMBC) NMR, and mass spectra, involving also comparison with data from the literature. (author)

  15. Saponins from seeds of Genus Camellia: Phytochemistry and bioactivity.

    Science.gov (United States)

    Guo, Na; Tong, Tuantuan; Ren, Ning; Tu, Youying; Li, Bo

    2018-05-01

    Camellia seeds have been traditionally used as oil raw materials in Asia, and are known for a wide spectrum of applications. Oleanane-type triterpene saponins are the major specialised metabolites in Camellia seeds, and more than seventy saponins have been isolated and characterized. These natural compounds have caught much attention due to their various biological and pharmacological activities, including modulation of gastrointestinal system, anti-cancer, anti-inflammation, anti-microorganism, antioxidation, neuroprotection, hypolipidemic effects, foaming and detergence, as well as helping the accumulation of pollutants by plants. These compounds have a promising application in medicine, agriculture, industry and environmental protection. The present paper summarized the information from current publications on Camellia seed saponins, with a focus on the advances made in chemical structures, determination methods, bioactivities and toxicity. We hope this article will stimulate further investigations on these compounds. Copyright © 2018 Elsevier Ltd. All rights reserved.

  16. Organic geochemistry and petrology of oil source rocks, Carpathian Overthrust region, southeastern Poland - Implications for petroleum generation

    Science.gov (United States)

    Kruge, M.A.; Mastalerz, Maria; Solecki, A.; Stankiewicz, B.A.

    1996-01-01

    The organic mailer rich Oligocene Menilite black shales and mudstones are widely distributed in the Carpathian Overthrust region of southeastern Poland and have excellent hydrocarbon generation potential, according to TOC, Rock-Eval, and petrographic data. Extractable organic matter was characterized by an equable distribution of steranes by carbon number, by varying amounts of 28,30-dinor-hopane, 18??(H)-oleanane and by a distinctive group of C24 ring-A degraded triterpanes. The Menilite samples ranged in maturity from pre-generative to mid-oil window levels, with the most mature in the southeastern portion of the study area. Carpathian petroleum samples from Campanian Oligocene sandstone reservoirs were similar in biomarker composition to the Menilite rock extracts. Similarities in aliphatic and aromatic hydrocarbon distributions between petroleum asphaltene and source rock pyrolyzates provided further evidence genetically linking Menilite kerogens with Carpathian oils.

  17. 19β,28-Epoxy-18α-olean-3β-ol

    Directory of Open Access Journals (Sweden)

    R. C. Santos

    2009-09-01

    Full Text Available The title triterpene, C30H50O2, is an 18α-oleanane derivative prepared by the Wagner–Meerwein rearrangement of betulin with Bi(OTf3.xH2O (OTF is trifluoromethanesulfonate. There are two symmetry-independent molecules in the asymmetric unit that show no significant differences concerning bond lengths and angles. The conformation of the six-membered rings is close to a chair form, while the five-membered epoxide rings adopt envelope conformations. All rings are trans-fused. In the crystal, molecules are held together by O—H...O hydrogen bonds. A quantum-mechanical ab initio Roothan Hartree–Fock calculation on the isolated molecule gives values for bond lengths and valency angles close to the experimental values. The calculations also reproduce well the molecular conformation with calculated puckering parameters that match well the observed values.

  18. Indolopyridoquinazoline alkaloids from Esenbeckia grandiflora mart. (Rutaceae); Alkaloides {beta}-indolopiridoquinazolinicos de Esenbeckia grandiflora mart. (Rutaceae)

    Energy Technology Data Exchange (ETDEWEB)

    Januario, Ana Helena; Vieira, Paulo Cezar; Silva, Maria Fatima das Gracas Fernandes da; Fernandes, Joao Batista [Universidade Federal de Sao Carlos (UFSCAR), SP (Brazil). Dept. de Quimica], e-mail: anahjanuario@unifran.br; Silva, Jorge Jose de Brito; Conserva, Lucia Maria [Universidade Federal de Alagoas (UFAL), Maceio, AL (Brazil). Inst. de Quimica e Biotecnologia

    2009-07-01

    The chemical composition of two specimens of Esenbeckia grandiflora, collected in the south and northeast regions of Brazil, was investigated. In this study, three b-indolopyridoquinazoline alkaloids from the leaves (rutaecarpine, 1-hydroxyrutaecarpine) and roots (euxylophoricine D) were isolated for the first time in this genus. In addition, the triterpenes {alpha}-amyrin, {beta}-amyrin, {alpha}-amyrenonol, {beta}-amyrenonol, 3{alpha}-hydroxy-ursan-12-one, and 3{alpha}-hydroxy-12,13-epoxy-oleanane, the coumarins auraptene, umbelliferone, pimpinelin, and xanthotoxin, the furoquinoline alkaloids delbine and kokusaginine, and the phytosteroids sitosterol, stigmasterol, campesterol and 3{beta}-O-{beta}-D-glucopyranosylsitosterol were also isolated from the leaves, twigs, roots and stems of this species. Structures of these compounds were established by spectral analysis. (author)

  19. Methyl Jasmonate-Elicited Transcriptional Responses and Pentacyclic Triterpene Biosynthesis in Sweet Basil1[C][W

    Science.gov (United States)

    Misra, Rajesh Chandra; Maiti, Protiti; Chanotiya, Chandan Singh; Shanker, Karuna; Ghosh, Sumit

    2014-01-01

    Sweet basil (Ocimum basilicum) is well known for its diverse pharmacological properties and has been widely used in traditional medicine for the treatment of various ailments. Although a variety of secondary metabolites with potent biological activities are identified, our understanding of the biosynthetic pathways that produce them has remained largely incomplete. We studied transcriptional changes in sweet basil after methyl jasmonate (MeJA) treatment, which is considered an elicitor of secondary metabolites, and identified 388 candidate MeJA-responsive unique transcripts. Transcript analysis suggests that in addition to controlling its own biosynthesis and stress responses, MeJA up-regulates transcripts of the various secondary metabolic pathways, including terpenoids and phenylpropanoids/flavonoids. Furthermore, combined transcript and metabolite analysis revealed MeJA-induced biosynthesis of the medicinally important ursane-type and oleanane-type pentacyclic triterpenes. Two MeJA-responsive oxidosqualene cyclases (ObAS1 and ObAS2) that encode for 761- and 765-amino acid proteins, respectively, were identified and characterized. Functional expressions of ObAS1 and ObAS2 in Saccharomyces cerevisiae led to the production of β-amyrin and α-amyrin, the direct precursors of oleanane-type and ursane-type pentacyclic triterpenes, respectively. ObAS1 was identified as a β-amyrin synthase, whereas ObAS2 was a mixed amyrin synthase that produced both α-amyrin and β-amyrin but had a product preference for α-amyrin. Moreover, transcript and metabolite analysis shed light on the spatiotemporal regulation of pentacyclic triterpene biosynthesis in sweet basil. Taken together, these results will be helpful in elucidating the secondary metabolic pathways of sweet basil and developing metabolic engineering strategies for enhanced production of pentacyclic triterpenes. PMID:24367017

  20. Multifunctional oxidosqualene cyclases and cytochrome P450 involved in the biosynthesis of apple fruit triterpenic acids.

    Science.gov (United States)

    Andre, Christelle M; Legay, Sylvain; Deleruelle, Amélie; Nieuwenhuizen, Niels; Punter, Matthew; Brendolise, Cyril; Cooney, Janine M; Lateur, Marc; Hausman, Jean-François; Larondelle, Yvan; Laing, William A

    2016-09-01

    Apple (Malus × domestica) accumulates bioactive ursane-, oleanane-, and lupane-type triterpenes in its fruit cuticle, but their biosynthetic pathway is still poorly understood. We used a homology-based approach to identify and functionally characterize two new oxidosqualene cyclases (MdOSC4 and MdOSC5) and one cytochrome P450 (CYP716A175). The gene expression patterns of these enzymes and of previously described oxidosqualene cyclases were further studied in 20 apple cultivars with contrasting triterpene profiles. MdOSC4 encodes a multifunctional oxidosqualene cyclase producing an oleanane-type triterpene, putatively identified as germanicol, as well as β-amyrin and lupeol, in the proportion 82 : 14 : 4. MdOSC5 cyclizes 2,3-oxidosqualene into lupeol and β-amyrin at a ratio of 95 : 5. CYP716A175 catalyses the C-28 oxidation of α-amyrin, β-amyrin, lupeol and germanicol, producing ursolic acid, oleanolic acid, betulinic acid, and putatively morolic acid. The gene expression of MdOSC1 was linked to the concentrations of ursolic and oleanolic acid, whereas the expression of MdOSC5 was correlated with the concentrations of betulinic acid and its caffeate derivatives. Two new multifuntional triterpene synthases as well as a multifunctional triterpene C-28 oxidase were identified in Malus × domestica. This study also suggests that MdOSC1 and MdOSC5 are key genes in apple fruit triterpene biosynthesis. © 2016 The Authors. New Phytologist © 2016 New Phytologist Trust.

  1. Composition and morphology of cuticular wax in blueberry (Vaccinium spp.) fruits.

    Science.gov (United States)

    Chu, Wenjing; Gao, Haiyan; Cao, Shifeng; Fang, Xiangjun; Chen, Hangjun; Xiao, Shangyue

    2017-03-15

    The chemical composition and morphology of cuticular wax in mature fruit of nine blueberry cultivars were investigated using gas chromatography-mass spectrometry (GC-MS) and scanning electron microscope (SEM). Triterpenoids and β-diketones were the most prominent compounds, accounting for on average 64.2% and 16.4% of the total wax, respectively. Ursolic or oleanolic acid was identified as the most abundant triterpenoids differing in cultivars. Two β-diketones, hentriacontan-10,12-dione and tritriacontan-12,14-dione, were detected in cuticular wax of blueberry fruits for the first time. Notably, hentriacontan-10,12-dione and tritriacontan-12,14-dione were only detected in highbush (V. corymbosum) and rabbiteye (V. ashei) blueberries, respectively. The results of SEM showed that a large amount of tubular wax deposited on the surface of blueberry fruits. There was no apparent difference in wax morphology among the nine cultivars. Copyright © 2016 Elsevier Ltd. All rights reserved.

  2. Chemical Constituents of Propolis from Vietnamese Trigona minor and Their Antiausterity Activity against the PANC-1 Human Pancreatic Cancer Cell Line.

    Science.gov (United States)

    Nguyen, Hai X; Nguyen, Mai T T; Nguyen, Nhan T; Awale, Suresh

    2017-08-25

    The ethanol extract of propolis from the Vietnamese stingless bee Trigona minor possessed potent preferential cytotoxicity against PANC-1 human pancreatic cancer cells in nutrient-deprived medium, with a PC 50 value of 14.0 μg/mL. Chemical investigation of this extract led to the isolation of 15 cycloartane-type triterpenoids, including five new compounds (1-5), and a lanostane-type triterpenoid. The structures of the new compounds were elucidated on the basis of NMR spectroscopic analysis. Among the isolated compounds, 23-hydroxyisomangiferolic acid B (5) and 27-hydroxyisomangiferolic acid (13) exhibited the most potent preferential cytotoxicity against PANC-1 human pancreatic cancer cells under nutrition-deprived conditions, with PC 50 values of 4.3 and 3.7 μM, respectively.

  3. Bioactive Pentacyclic Triterpene Ester Derivatives from Alnus viridis ssp. viridis Bark.

    Science.gov (United States)

    Novakovic, Miroslav; Nikodinovic-Runic, Jasmina; Veselinovic, Jovana; Ilic-Tomic, Tatjana; Vidakovic, Vera; Tesevic, Vele; Milosavljevic, Slobodan

    2017-05-26

    Seven derivatives of pentacyclic triterpene acids (1-7) were isolated from the bark of Alnus viridis ssp. viridis using a combination of column chromatography and semipreparative HPLC. Compounds 1-3, 6, and 7 were determined to be new after spectroscopic data interpretation and were assigned as 27-hydroxyalphitolic acid derivatives (1-3), a 27-hydroxybetulinic acid derivative (6), and a 3-epi-maslinic acid derivative (7), respectively. Pentacyclic triterpenoids with a C-27 hydroxymethyl group have been found in species of the genus Alnus for the first time. These compounds were subjected to cytotoxicity testing against a number of cancer cell lines. Also, selected pentacyclic triterpenoids were selected as potential inhibitors of topoisomerases I and IIα for an in silico investigation.

  4. Preliminary correlation of organic molecular tracers in residential wood smoke with the source of fuel

    Science.gov (United States)

    Standley, Laurel J.; Simoneit, Bernd R. T.

    Polar cyclic di- and triterpenoids were analyzed in the extracts of residential wood combustion aerosols collected in suburban sections of Eugene, Oakridge and Corvallis, Oregon. Additional samples collected included alder wood, smoke from two wood stoves burning only alder or pine as fuel, soot from a stove burning alder and a fireplace where oak was the predominant fuel. Due to the relatively cooler temperatures present under the smoldering conditions of residential wood combustion, as compared to the active burning of forest fires and slash burns, incomplete combustion resulted in the preservation of high levels of the natural products. There were three distinct signatures which could be used to trace relative input from coniferous, alder and oak combustion products, i.e. diterpenoids, lupane-derived triterpenoids and friedelin, respectively. Conifer combustion products dominated the suburban smoke aerosols.

  5. Dendranthema grandiflorum, a hybrid ornamental plant, is a source of larvicidal compounds against Aedes aegypti larvae

    Directory of Open Access Journals (Sweden)

    Kassia C.V.W. Spindola

    Full Text Available Abstract In hybrid cultivated form, Dendranthema grandiflorum (Ramat. Kitam., Asteraceae, flowers (Chrysanthemum morifolium Ramat. were utilized in the production of extracts, which were analyzed for larvicidal activity against Aedes aegypti third instar larvae. Methanol and dichloromethane extracts showed LC50 values of 5.02 and 5.93 ppm, respectively. Using GC–MS, phytochemical analyses of the dichloromethane extract showed the presence of triterpenoids and fatty acids, while flavonoids and caffeoylquinic acids were shown to occur in the methanol extract by ESI Fourier Transform Ion Cyclotron Resonance Mass Spectrometry (ESI-FT-ICR-MS. Triterpenoids and fatty acids are well known insecticidal compounds. From this study, it can be concluded that D. grandiflorum grown for floriculture, as an agribusiness, can have additional applications as raw material for the production of insecticidal products.

  6. Phytochemical composition and antioxidant capacity of Cordia dichotoma seeds.

    Science.gov (United States)

    Tian, Shuge; Liu, Feng; Zhang, Xuejia; Upur, Halmuart

    2014-09-01

    This study aims to determine the phytochemical composition and antioxidant activity of air-dried Cordia dichotoma seeds. Total polyphenolic content was analyzed via the Folin-Ciocalteu method. Total triterpenoid content and amino acids was analyzed colorimetrically. The rosmarinic acid content was examined using high-performance liquid chromatography tandem mass spectrometry. The ethanolic extracts contained polyphenolic compounds (1.0%), triterpenoids (0.075%), amino acids (1.39%), and rosmarinic acid (0.0028%). The results from this study indicate that C. dichotoma seeds are a rich source of polyphenolic compounds and amino acids, which can be used for quality assessment. The ethanolic extract of C. dichotoma seeds has good antioxidant capacity.

  7. Antitubercular Activity of Mycelium-Associated Ganoderma Lanostanoids.

    Science.gov (United States)

    Isaka, Masahiko; Chinthanom, Panida; Sappan, Malipan; Supothina, Sumalee; Vichai, Vanicha; Danwisetkanjana, Kannawat; Boonpratuang, Thitiya; Hyde, Kevin D; Choeyklin, Rattaket

    2017-05-26

    In a continuation of our research into antitubercular lanostane triterpenoids from submerged cultures of Ganoderma species, three strains, Ganoderma orbiforme BCC 22325, Ganoderma sp. BCC 60695, and Ganoderma australe BCC 22314, have been investigated. Fourteen new lanostane triterpenoids, together with 35 known compounds, were isolated. Antitubercular activities of these mycelium-associated Ganoderma lanostanoids against Mycobacterium tuberculosis H37Ra were evaluated. Taken together with the assay data of previously isolated compounds, structure-activity relationships of the antitubercular activity are proposed. Most importantly, 3β- and 15α-acetoxy groups were shown to be critical for antimycobacterial activity. The most potent compound was (24E)-3β,15α-diacetoxylanosta-7,9(11),24-trien-26-oic acid (35).

  8. Integrative Approaches for the Identification and Localization of Specialized Metabolites in Tripterygium Roots1[OPEN

    Science.gov (United States)

    Fischedick, Justin T.; Lange, Malte F.; Poirier, Brenton C.

    2017-01-01

    Members of the genus Tripterygium are known to contain an astonishing diversity of specialized metabolites. The lack of authentic standards has been an impediment to the rapid identification of such metabolites in extracts. We employed an approach that involves the searching of multiple, complementary chromatographic and spectroscopic data sets against the Spektraris database to speed up the metabolite identification process. Mass spectrometry-based imaging indicated a differential localization of triterpenoids to the periderm and sesquiterpene alkaloids to the cortex layer of Tripterygium roots. We further provide evidence that triterpenoids are accumulated to high levels in cells that contain suberized cell walls, which might indicate a mechanism for storage. To our knowledge, our data provide first insights into the cell type specificity of metabolite accumulation in Tripterygium and set the stage for furthering our understanding of the biological implications of specialized metabolites in this genus. PMID:27864443

  9. Photooxidation of nimbin and salannin, tetranortriterpenoids from the neem tree (Azadirachta indica)

    International Nuclear Information System (INIS)

    Jarvis, A.P.; Johnson, S.; Morgan, E.D.; Simmonds, M.S.J.; Blaney, W.M.

    1997-01-01

    Nimbin and salannin, major triterpenoids accompanying azadirachtin in extracts of neem (Azadirachta indica) seeds, were photooxidized by UV light in the presence of oxygen to more polar, unstable intermediates that rearranged on silica gel to two final products in which the furan ring had been oxidized to isomeric hydroxybutenolides. The isomeric hydroxybutenolides were also readily formed when a crude extract of triterpenoids from neem seeds was irradiated, and both isomers of salannin have been isolated from seeds. Photooxidation of nimbin and salannin proceeded much faster than that of azadirachtin. All photoproducts showed some biological activity against Spodoptera littoralis, Locusta migratoria, and Schistocerca gregaria. Isonimbinolide was as potent as azadirachtin at inhibiting feeding in all three species, and it also inhibited the growth of S. littoralis. Isosalanninolide showed potent antifeedant and growth inhibitory activity against S. littoralis

  10. Identification of novel autophagic Radix Polygalae fraction by cell membrane chromatography and UHPLC-(Q)TOF-MS for degradation of neurodegenerative disease proteins

    OpenAIRE

    An-Guo Wu; Vincent Kam-Wai Wong; Wu Zeng; Liang Liu; Betty Yuen-Kwan Law

    2015-01-01

    With its traditional use in relieving insomnia and anxiety, our previous study has identified onjisaponin B from Radix Polygalae (RP), as a novel autophagic enhancer with potential neuroprotective effects. In current study, we have further identified a novel active fraction from RP, contains 17 major triterpenoid saponins including the onjisaponin B, by the combinational use of cell membrane chromatography (CMC) and ultra-performance liquid chromatography coupled to (quadrupole) time-of-fligh...

  11. Phytochemical investigation and antimicrobial activity of Caesalpinia bonduc (linn) Roxb seeds

    OpenAIRE

    V. Subramani; M. Kamaraj; B. Ramachandran; J. Jerome Jeyakumar

    2014-01-01

    The aim of the study was to investigate phytochemical properties, antimicrobial activity and trace metal concentrations of Caesalpinia bonducella. The phytochemical screening of the extracts of leaves of C. bonducella revealed the presence of bioactive compounds such as Steroid, Triterpenoids, Reducing Sugar(A), Reducing Sugar(B), Sugars, Flavonoids, Saponin, Amino acids with absence of Alkaloids, Phenolic Compounds, Catachins, Tannins, Anthroquinones.  The ethanol solvent was used for extrac...

  12. Secondary Metabolites from Inula britannica L. and Their Biological Activities

    Directory of Open Access Journals (Sweden)

    Yoon-Ha Kim

    2010-03-01

    Full Text Available Inula britannica L., family Asteraceae, is used in traditional Chinese and Kampo Medicines for various diseases. Flowers or the aerial parts are a rich source of secondary metabolites. These consist mainly of terpenoids (sesquiterpene lactones and dimmers, diterpenes and triterpenoids and flavonoids. The isolated compounds have shown diverse biological activities: anticancer, antioxidant, anti-inflammatory, neuroprotective and hepatoprotective activities. This review provides information on isolated bioactive phytochemicals and pharmacological potentials of I. britannica.

  13. Two new compounds from the fruits of Buddleja lindleyana with neuroprotective effect.

    Science.gov (United States)

    Wu, De-Ling; Wang, Yang-Kui; Liu, Jing-Song; Wang, Xun-Cui; Zhang, Wei

    2012-01-01

    Two new triterpenoid glycosides, mimengosides H (1) and I (2), were isolated from the fruits of Buddleja lindleyana Fort. Their structures were determined by extensive spectroscopic methods. Neuroprotective effects of these isolates against 1-methyl-4-phenylpyridinium ion-induced neurotoxicity in PC12 cells were evaluated. Pretreatment with compound 1 had potential protective effect in a concentration range from 0.1 to 1 μmol l⁻¹.

  14. Bisabolane-type sesquiterpenes from the aerial parts of Lippia dulcis.

    Science.gov (United States)

    Ono, Masateru; Tsuru, Tsuyoshi; Abe, Hiroaki; Eto, Masashi; Okawa, Masafumi; Abe, Fumiko; Kinjo, Junei; Ikeda, Tsuyoshi; Nohara, Toshihiro

    2006-10-01

    Six new bisabolane-type sesquiterpenes, peroxylippidulcines A-C (3-5), peroxyepilippidulcine B (6), and epilippidulcines B (7) and C (8), have been isolated from the aerial parts of Lippia dulcis, along with two known bisabolane-type sesquiterpenes, seven known flavonoids, and a known triterpenoid. The structures of 3-8 were characterized on the basis of NMR, MS, specific rotation, and X-ray crystallographic analysis data and chemical evidence.

  15. Application of High-Performance Liquid Chromatography Coupled with Linear Ion Trap Quadrupole Orbitrap Mass Spectrometry for Qualitative and Quantitative Assessment of Shejin-Liyan Granule Supplements

    OpenAIRE

    Jifeng Gu; Weijun Wu; Mengwei Huang; Fen Long; Xinhua Liu; Yizhun Zhu

    2018-01-01

    A method for high-performance liquid chromatography coupled with linear ion trap quadrupole Orbitrap high-resolution mass spectrometry (HPLC-LTQ-Orbitrap MS) was developed and validated for the qualitative and quantitative assessment of Shejin-liyan Granule. According to the fragmentation mechanism and high-resolution MS data, 54 compounds, including fourteen isoflavones, eleven ligands, eight flavonoids, six physalins, six organic acids, four triterpenoid saponins, two xanthones, two alkaloi...

  16. Efek Kombinasi Ekstrak Etanol Daun Sirih (Piper betle L) Dengan Amoksisilin Terhadap Pertumbuhan Bakteri Escherichia coli dan Staphylococcus aureus

    OpenAIRE

    Siahaan, Remon Gortap

    2017-01-01

    The combination of antibiotic and plant extract is a new concept and has been used for the treatment of resistant bacterial infections. Betel leaves have antibacterial activity against Escherichia coli and Staphylococcus aureus because they contain secondary metabolites such as flavonoid, saponin, tanin, and steroid/ triterpenoid. Extract combination with amoxicillin needs to be tested to determine the effectiveness of a single comparison. This study aims was to investigated the characteristi...

  17. Chemical constituents of Simarouba versicolor

    International Nuclear Information System (INIS)

    Arriaga, Angela M.C.; Mesquita, Aldenor C. de; Pouliquen, Yvone B.M.; Lima, Roberto A. de; Cavalcante, Sergio H.; Carvalho, Mario G. de; Siqueira, Jose A. de; Alegrio, Leila V.; Braz-Filho, Raimundo

    2002-01-01

    From the roots, stems and fruits of Simarouba versicolor (Simaroubaceae) were isolated quassinoids (3, 5-7), triterpenoids (8-14), a mixture of steroids (15-17), the flavonoid kaempferol (18) and the squalene derivative 11,14-diacetoxy-7,10; 15,18-diepoxy-6,19-dihidroxy-6,7,10,11,14,15,18,19-octahydrosqualene (19). Spectral data were used for structural characterization. (author)

  18. Chemical constituents of Simarouba versicolor

    Energy Technology Data Exchange (ETDEWEB)

    Arriaga, Angela M.C.; Mesquita, Aldenor C. de; Pouliquen, Yvone B.M. [Ceara Univ., Fortaleza, CE (Brazil). Dept. de Quimica Organica e Inorganica; Lima, Roberto A. de; Cavalcante, Sergio H. [Alagoas Univ., Maceio, AL (Brazil). Dept. de Quimica; Carvalho, Mario G. de; Siqueira, Jose A. de; Alegrio, Leila V. [Universidade Federal Rural do Rio de Janeiro, RJ (Brazil). Dept. de Quimica; Braz-Filho, Raimundo [Universidade Estadual do Norte Fluminense (UENF), Campos dos Goytacases, RJ (Brazil). Setor de Quimica de Produtos Naturais]. E-mail: braz@uenf.br

    2002-09-01

    From the roots, stems and fruits of Simarouba versicolor (Simaroubaceae) were isolated quassinoids (3, 5-7), triterpenoids (8-14), a mixture of steroids (15-17), the flavonoid kaempferol (18) and the squalene derivative 11,14-diacetoxy-7,10; 15,18-diepoxy-6,19-dihidroxy-6,7,10,11,14,15,18,19-octahydrosqualene (19). Spectral data were used for structural characterization. (author)

  19. Antitumour, Antimicrobial, Antioxidant and Antiacetylcholinesterase Effect of Ganoderma Lucidum Terpenoids and Polysaccharides: A Review

    OpenAIRE

    Darija Cör; Željko Knez; Maša Knez Hrnčič

    2018-01-01

    Ganoderma lucidum (Reishi) is a popular medicinal mushroom and has been used in oriental medicine because of its promoting effects on health and life expectancy. G. lucidum contains various compounds with a high grade of biological activty, which increase the immunity and show antitumour, antimicrobial, anti-inflammatory, antioxidant and acetylcholinesterase inhibitory activity. Several of these substances belong to the triterpenoids and polysaccharides classes. Proteins, lipids, phenols, ste...

  20. Cucurbitacin: Ancient Compound Shedding New Light on Cancer Treatment

    OpenAIRE

    Lee, Dhong Hyun; Iwanski, Gabriela B.; Thoennissen, Nils H.

    2010-01-01

    Cucurbitacins and their derivatives are triterpenoids found in medicinal plants known for their diverse pharmacological and biological activities, including anticancer effects, throughout human history. Although initial attention to cucurbitacin as a potential anticancer drug withered for decades, recent discoveries showing that cucurbitacin is a strong STAT3 (Signal Transducers and Activators of Transcription-3) inhibitor have reclaimed the attention of the drug industry one more time. There...

  1. HRGC-MS analysis of terpenoids from Maytenus ilicifolia and Maytenus aquifolium ("espinheira santa"

    Directory of Open Access Journals (Sweden)

    Cordeiro Paulo J. M.

    1999-01-01

    Full Text Available This work describes the identification of some of the minor chemical constituents of "espinheira santa" (Maytenus ilicifolia and Maytenus aquifolium, Celastraceae, a medicinal plant widely utilized in Brazil. By using high resolution gas chromatography coupled to mass spectrometry (HRGC-MS, it was possible to identify mainly triterpenoids and steroids in "espinheira santa", most of them reported for the first time in both Maytenus species.

  2. Evaluation of Biological Activities of Extracts and Chemical ...

    African Journals Online (AJOL)

    flavones, triterpenoids and steroids [2,4-5]. The volatile constituents of the flowers have also been reported [6]. Different parts of the plant are reported to be used in traditional medicine for ... 0/0/1 v/v/v) to yield six fractions (FB1 - 5). FB1 and FB3 were ... Sigma) was added to each well and the plates incubated at 37 °C for 30 ...

  3. Pyrrolizidine Alkaloids from Onosmakaheirei Teppner (Boraginaceae

    Directory of Open Access Journals (Sweden)

    Ioanna Maria Orfanou

    2016-03-01

    Full Text Available The new pyrrolizidine alkaloid (PA 3΄-O-acetylechinatine N-oxide (7, along with two more known PAs (5, 6, two known flavonoids (3, 4, one known alkannin (1, two known triterpenoids, one known sterol, and allantoin (2 were isolated from the aerial parts of Onosma kaheirei. In addition, the retention indeces of the reduced PAs 6 and 7 were determined in a DB-5 WCOT column, to aid their detection by GC/MS in the future.

  4. Cucurbitane Glycosides Derived from Mogroside IIE: Structure-Taste Relationships, Antioxidant Activity, and Acute Toxicity

    Directory of Open Access Journals (Sweden)

    Lei Wang

    2014-08-01

    Full Text Available Mogroside IIE is a bitter triterpenoid saponin which is the main component of unripe Luo Han Guo fruit and a precursor of the commercially available sweetener mogroside V. In this study, we developed an enzymatic glycosyl transfer method, by which bitter mogroside IIE could be converted into a sweet triterpenoid saponin mixture. The reactant concentration, temperature, pH and buffer system were studied. New saponins with the α-glucose group were isolated from the resulting mixtures, and the structures of three components of the extract were determined. The structure-taste relationships of these derivatives were also studied together with those of the natural mogrosides. The number and stereoconfiguration of glucose groups present in the mogroside molecules were found to be the main factor to determine the sweet or bitter taste of a compound. The antioxidant and food safety properties were initially evaluated by their radical scavenging ability and via 7 day mice survival tests, respectively. The results showed that the sweet triterpenoid saponin mixture has the same favorable physiological and safety characteristics as the natural mogrosides.

  5. Evidence for a Saponin Biosynthesis Pathway in the Body Wall of the Commercially Significant Sea Cucumber Holothuria scabra.

    Science.gov (United States)

    Mitu, Shahida Akter; Bose, Utpal; Suwansa-Ard, Saowaros; Turner, Luke H; Zhao, Min; Elizur, Abigail; Ogbourne, Steven M; Shaw, Paul Nicholas; Cummins, Scott F

    2017-11-07

    The sea cucumber (phylum Echinodermata) body wall is the first line of defense and is well known for its production of secondary metabolites; including vitamins and triterpenoid glycoside saponins that have important ecological functions and potential benefits to human health. The genes involved in the various biosynthetic pathways are unknown. To gain insight into these pathways in an echinoderm, we performed a comparative transcriptome analysis and functional annotation of the body wall and the radial nerve of the sea cucumber Holothuria scabra ; to define genes associated with body wall metabolic functioning and secondary metabolite biosynthesis. We show that genes related to signal transduction mechanisms were more highly represented in the H. scabra body wall, including genes encoding enzymes involved in energy production. Eight of the core triterpenoid biosynthesis enzymes were found, however, the identity of the saponin specific biosynthetic pathway enzymes remains unknown. We confirm the body wall release of at least three different triterpenoid saponins using solid phase extraction followed by ultra-high-pressure liquid chromatography-quadrupole time of flight-mass spectrometry. The resource we have established will help to guide future research to explore secondary metabolite biosynthesis in the sea cucumber.

  6. Evidence for a Saponin Biosynthesis Pathway in the Body Wall of the Commercially Significant Sea Cucumber Holothuria scabra

    Directory of Open Access Journals (Sweden)

    Shahida Akter Mitu

    2017-11-01

    Full Text Available The sea cucumber (phylum Echinodermata body wall is the first line of defense and is well known for its production of secondary metabolites; including vitamins and triterpenoid glycoside saponins that have important ecological functions and potential benefits to human health. The genes involved in the various biosynthetic pathways are unknown. To gain insight into these pathways in an echinoderm, we performed a comparative transcriptome analysis and functional annotation of the body wall and the radial nerve of the sea cucumber Holothuria scabra; to define genes associated with body wall metabolic functioning and secondary metabolite biosynthesis. We show that genes related to signal transduction mechanisms were more highly represented in the H. scabra body wall, including genes encoding enzymes involved in energy production. Eight of the core triterpenoid biosynthesis enzymes were found, however, the identity of the saponin specific biosynthetic pathway enzymes remains unknown. We confirm the body wall release of at least three different triterpenoid saponins using solid phase extraction followed by ultra-high-pressure liquid chromatography-quadrupole time of flight-mass spectrometry. The resource we have established will help to guide future research to explore secondary metabolite biosynthesis in the sea cucumber.

  7. Determination of betulinic acid, oleanolic acid and ursolic acid from Achyranthes aspera L. using RP-UFLC-DAD analysis and evaluation of various parameters for their optimum yield.

    Science.gov (United States)

    Pai, Sandeep R; Upadhya, Vinayak; Hegde, Harsha V; Joshi, Rajesh K; Kholkute, Sanjiva D

    2016-03-01

    Achyranthes aspera L. is a well known herb commonly used in traditional system of Indian medicine to treat various disorders, such as cough, dysentery, gonorrhea, piles, kidney stone, pneumonia, renal dropsy, skin eruptions, snake bite, etc. Here, we used RP-UFLC-DAD method for determining triterpenoids betulinic acid (BA), oleanolic acid (OA) and ursolic acid (UA) from A. aspera. Optimum yield of these compounds were studied and evaluated using parameters viz., method of extraction, time of extraction, age of plant and plant parts (leaves, stem and roots). Linear relationships in RP-UFLC-DAD analysis were obtained in the range 0.05-100 µg/mL with 0.035, 0.042 and 0.033 µg/mL LOD for BA, OA and UA, respectively. Of the variables tested, extraction method and parts used significantly affected content yield. Continuous shaking extraction (CSE) at ambient temperature gave better extraction efficiency than exposure to ultra sonic extraction (USE) or microwave assisted extraction (MAE) methods. The highest content of BA, OA and UA were determined individually in leaf, stem and root extracts with CSE. Collective yield of these triterpenoids were higher in leaf part exposed to 15 min USE method. To best of our knowledge, the study newly reports UA from A. aspera and the same was confirmed using ATR-FT-IR studies. This study explains the distribution pattern of these major triterpenoids and optimum extraction parameters in detail.

  8. Application of positive mode atmospheric chemical ionisation to distinguish epimeric oleanolic and ursolic acids.

    Science.gov (United States)

    Townley, Chloe; Brettell, Rhea C; Bowen, Richard D; Gallagher, Richard T; Martin, William H C

    2015-01-01

    A new and more reliable method is reported for distinguishing the equatorial and axial epimers of oleanolic and ursolic acids and related triterpenoids based primarily on the relative abundance of the [M+H](+) and [M+-H(2)O](+) signals in their positive mode atmospheric pressure chemical ionisation mass spectra. The rate of elimination of water, which is the principal primary fragmentation of protonated oleanolic and ursolic acids, depends systematically on the stereochemistry of the hydroxyl group in the 3 position. For the b-epimer, in which the 3-hydroxyl substituent is in an equatorial position,[M+-H(2)O](+) is the base peak. In contrast, for the α-epimer, where the 3-hydroxyl group is axial, [M + H](+) is the base peak. This trend, which is general for a range of derivatives of oleanolic and ursolic acids, including the corresponding methyl esters, allows epimeric triterpenoids in these series to be securely differentiated. Confirmatory information is available from the collision-induced dissociation of the [M+-H(2)O](+) primary fragment ions, which follow different pathways for the species derived from axial and equatorial epimers of oleanolic and ursolic acids. These two pieces of independent spectral information permit the stereochemistry of epimeric oleanolic and ursolic acids (and selected derivatives) to be assigned with confidence without relying either on chromatographic retention times or referring to the spectra or other properties of authentic samples of these triterpenoids.

  9. Uji Fitokimia, Toksisitas dan Aktivitas Antioksidan Fraksi n-heksan dan Etil Asetat terhadap Ekstrak Jahe Merah (Zingiber officinale var. amarum

    Directory of Open Access Journals (Sweden)

    Alpina Nora Kaban

    2016-11-01

    Full Text Available Has conducted research on the phytochemical test, toxicity test and test the antioxidant activity of the fraction of n-hexane and ethyl acetate to extract red ginger (Zingiber officinale amarum var.. The dried leaves weighing 382 grams, was macerated using methanol, filtered and concentrated by rotary evaporator. Then the total extract of red ginger in fractionation with n-hexane and ethyl acetate. Based on the test results of secondary metabolites phytochemical extracts of total red ginger (Zingiber officinale var amarum. Are alkaloids, flavonoids, triterpenoids and phenolic. N-hexane fraction contains alkaloids, flavonoids, steroids, triterpenoids and phenolic. Ethyl acetate fractions contain alkaloids, flavonoids, triterpenoids and phenolic. Toxicity test showed the mortality rate of shrimp larvae Artemia salina Leach using Probit Analysis SAS (Statistical Analysis System to determine the value of 50% Lethal Concentration (LC50, showed that the fraction of n-hexane toxicity with LC50 values of 63.8130 ppm; extracts of total was 71.0121 ppm and ethyl acetate was 3821.89 ppm. Test the antioxidant activity using DPPH free radical reduction in the spectrophotometer and IC50 values obtained on a total extract was 32.19 ppm; n-hexane was fraction 35.63 ppm; and ethyl acetate fraction was 25.69 ppm.

  10. A novel Nrf2 activator from microbial transformation inhibits radiation-induced dermatitis in mice

    International Nuclear Information System (INIS)

    Nakagami, Yasuhiro; Masuda, Kayoko

    2016-01-01

    Nuclear factor erythroid 2-related factor 2 (Nrf2) is a transcriptional factor that regulates many antioxidants, and we have recently succeeded in obtaining a novel Nrf2 activator, RS9, from microbial transformation. RS9 is categorized as a triterpenoid, and well-known triterpenoids such as RTA 402 (bardoxolone methyl) and RTA 408 have been tested in clinical trials. RTA 408 lotion is currently being tested in patients at risk for radiation dermatitis. This prompted us to study the profiles of RS9 in the skin. All the above triterpenoids increased the level of an Nrf2-targeted gene, NADPH:quinone oxidoreductase-1, in normal human epidermal keratinocytes. Among them, the activity of RS9 was prominent; furthermore, the cellular toxicity was less compared with RTA compounds. BALB/c mice were irradiated with 30 Gy/day on Day 0, and compounds were topically applied on the back once daily from Day 1 to Day 30. Dermatitis scores peaked on Day 18, with a score of 2.6 in vehicle-treated mice, and topical applications of 0.1% RTA 402, RTA 408 and RS9 reduced the scores to 1.8, 2.0 and 1.4, respectively. Moreover, the percentage of animals with scores ≥2 was analyzed, and 0.1% RS9 suppressed the percentage from 100% to 47%. These results imply that RS9 has potential efficacy for treating radiation dermatitis.

  11. Changes in Renal Function and Oxidative Status Associated with the Hypotensive Effects of Oleanolic Acid and Related Synthetic Derivatives in Experimental Animals.

    Directory of Open Access Journals (Sweden)

    Hlengiwe Pretty Madlala

    Full Text Available The triterpene oleanolic acid (OA is known to possess antihypertensive actions. In the present study we to compared the effects of the triterpene on mean arterial blood pressure (MAP and kidney function following acute administration in normotensive animals with those of its related oleanane synthetic derivatives (brominated oleanolic acid, Br-OA and oleanolic acid methyl ester, Me-OA. We also used experimental models of hypertension to further explore the effects of sub-chronic oral OA treatment and evaluated influences on oxidative status.OA was extracted from dried flower buds of Syzygium aromaticum using a previously validated protocol in our laboratory. Me-OA and Br-OA were synthesized according to a method described. Rats were supplemented with lithium chloride (12 mmol L-1 prior to experimentation in order to raise plasma lithium to allow measurements of lithium clearance and fractional excretion (FELi as indices of proximal tubular Na+ handling. Anaesthetized animals were continuously infused via the right jugular with 0.077M NaCl. MAP was measured via a cannula inserted in the carotid artery, and urine was collected through a cannula inserted in the bladder. After a 3.5 h equilibration, MAP, urine flow, electrolyte excretion rates were determined for 4 h of 1 h control, 1.5 h treatment and 1.5 h recovery periods. OA, Me-OA and Br-OA were added to the infusate during the treatment period. We evaluated sub-chronic effects on MAP and kidney function in normotensive Wistar rats and in two animal models of hypertension, spontaneously hypertensive rats (SHR and Dahl salt-sensitive (DSS rats, during 9-week administration of OA (p.o.. Tissue oxidative status was examined in these animals at the end of the study. Increasing evidence suggests that and renal function disturbances and oxidative stress play major roles in the pathogenesis of hypertension.Acute infusion OA and oleanane derivatives displayed qualitatively similar effects in decreasing

  12. Virus-Induced Silencing of Key Genes Leads to Differential Impact on Withanolide Biosynthesis in the Medicinal Plant, Withania somnifera.

    Science.gov (United States)

    Agarwal, Aditya Vikram; Singh, Deeksha; Dhar, Yogeshwar Vikram; Michael, Rahul; Gupta, Parul; Chandra, Deepak; Trivedi, Prabodh Kumar

    2018-02-01

    Withanolides are a collection of naturally occurring, pharmacologically active, secondary metabolites synthesized in the medicinally important plant, Withania somnifera. These bioactive molecules are C28-steroidal lactone triterpenoids and their synthesis is proposed to take place via the mevalonate (MVA) and 2-C-methyl-d-erythritol-4-phosphate (MEP) pathways through the sterol pathway using 24-methylene cholesterol as substrate flux. Although the phytochemical profiles as well as pharmaceutical activities of Withania extracts have been well studied, limited genomic information and difficult genetic transformation have been a major bottleneck towards understanding the participation of specific genes in withanolide biosynthesis. In this study, we used the Tobacco rattle virus (TRV)-mediated virus-induced gene silencing (VIGS) approach to study the participation of key genes from MVA, MEP and triterpenoid biosynthesis for their involvement in withanolide biosynthesis. TRV-infected W. somnifera plants displayed unique phenotypic characteristics and differential accumulation of total Chl as well as carotenoid content for each silenced gene suggesting a reduction in overall isoprenoid synthesis. Comprehensive expression analysis of putative genes of withanolide biosynthesis revealed transcriptional modulations conferring the presence of complex regulatory mechanisms leading to withanolide biosynthesis. In addition, silencing of genes exhibited modulated total and specific withanolide accumulation at different levels as compared with control plants. Comparative analysis also suggests a major role for the MVA pathway as compared with the MEP pathway in providing substrate flux for withanolide biosynthesis. These results demonstrate that transcriptional regulation of selected Withania genes of the triterpenoid biosynthetic pathway critically affects withanolide biosynthesis, providing new horizons to explore this process further, in planta.

  13. UJI FITOKIMIA SENYAWA KIMIA AKTIF AKAR NIPAH (Nyfa Fruticans WURMB SEBAGAI TUMBUHAN OBAT DI KALIMANTAN SELATAN

    Directory of Open Access Journals (Sweden)

    Rosidah R Radam

    2017-02-01

    Full Text Available Nipa (Nypa fruticans WURMB classified in Palma family and grow in riptide area. This Research aims to know active Chemical compounds in Nipa root. We Hope that this Research will provide new information about active Chemical compounds in Nipa root, so that we can improve the benefit value of Nipa as One of the medicinal herb. Nipa root samples is taken in Tanah Bumbu District, samples examined in Laboratory of F-MIPA UNLAM. The observed parameters in thus Chemical Test are the active Chemical compounds: alkaloid, steroid, triterpenoid, flavonoid, and tannin. The Content of active Chemical compound is presented in Table and concluded descriptively. The Result of active Chemical compound consist in Nipa’s root shows that Alkaloid, Steroid, Triterpenoid, Flavonoid , and tannin compound is do contains in Nipa root. This active Chemical compound in Nipa root can be Led as the basic Chemical informative to utilize Nipa root as analgesics Medical for such disease. Nipah (nypa fruticans WURMB merupakan tumbuhan yang termasuk famili Palmae dan   tumbuh di daerah  pasang   surut.  Penelitian ini bertujuan untuk mengetahui  kandungan senyawa-senyawa kimia aktif pada akar nipah. Manfaat dari penelitian ini untuk memberikan informasi baru tentang senyawa aktif yang terdapat pada akar nipah, sehingga dapat meningkatkan nilai guna dan manfaat tumbuhan nipah sebagai salah satu tanaman obat. Pengambilan sample akar nipah dilakukan Kabupaten Tanah Bumbu  sedangkan pengujian sample akar nipah dilakukan di Laboratorium F-MIFA UNLAM. Parameter-parameter yang diamati pada pengujian kimia tersebut adalah senyawa-senyawa kimia aktif yaitu alkaloid, steroid, triterpenoid flavonoid, dan tanin. Data hasil uji kandungan senyawa kimia aktif  ditabulasi dan disimpulkan secara diskriptif. Hasil pengujian terhadap senyawa kimia aktif yang terkandung dalam akar Nifah ini menunjukan bahwa senyawa Alkaloid, Steroid, Triterpenoid, Flavonoid , dan tanin memang dikandung

  14. The Genus Phyllanthus: An Ethnopharmacological, Phytochemical, and Pharmacological Review

    Directory of Open Access Journals (Sweden)

    Xin Mao

    2016-01-01

    Full Text Available The plants of the genus Phyllanthus (Euphorbiaceae have been used as traditional medicinal materials for a long time in China, India, Brazil, and the Southeast Asian countries. They can be used for the treatment of digestive disease, jaundice, and renal calculus. This review discusses the ethnopharmacological, phytochemical, and pharmacological studies of Phyllanthus over the past few decades. More than 510 compounds have been isolated, the majority of which are lignins, triterpenoids, flavonoids, and tannins. The researches of their remarkable antiviral, antioxidant, antidiabetic, and anticancer activities have become hot topics. More pharmacological screenings and phytochemical investigations are required to support the traditional uses and develop leading compounds.

  15. Triterpenos isolados de Eschweilera longipes miers (Lecythidaceae

    Directory of Open Access Journals (Sweden)

    Carvalho Mario Geraldo de

    1998-01-01

    Full Text Available The phytochemical studies of Eschweilera longipes have led to the identification of ten triterpenoids: fridelin, fridelinol, alpha-amirin, beta-amirin, 3beta-O-cinamoyl-alpha-amirin, 3beta-O-cinamoyl-beta-amirin, alpha-amirenone, beta-amirenone, 3-alpha-hidroxi-lupeol, 3-alpha-hidroxi-taraxasterol, along with b-sitosterol, stigmasterol, alpha -tocopherol and tocotrienol. The structures of these compounds were identified by analysis of IR, ¹H and 13C NMR data and comparison with values of literature.

  16. Chemical constituents of the aerial part of Taraxacum mongolicum and their chemotaxonomic significance.

    Science.gov (United States)

    Li, Wei; Lee, Changyeol; Kim, Young Ho; Ma, Jin Yeul; Shim, Sang Hee

    2017-10-01

    A phytochemical investigation of Taraxacum mongolicum led to the isolation of 24 compounds, including six flavonoids (1-6), four sesquiterpenes (7-10), two sphingolipids (11 and 12), six glycerols (13-18) and six triterpenoids and sterols (19-24). The structures of these compounds were identified by spectroscopic methods, and their data compared with those reported in the literature. This is the first report of compounds 11-19 from T. mongolicum and the genus Taraxacum, and compounds 11, 12, 15, 16, 18 and 19 from the Asteraceae family. The chemotaxonomic relationship between T. mongolicum and other Taraxacum species is also discussed.

  17. Gas chromatography/mass spectrometry characterization of historical varnishes of ancient Italian lutes and violin.

    Science.gov (United States)

    Echard, J P; Benoit, C; Peris-Vicente, J; Malecki, V; Gimeno-Adelantado, J V; Vaiedelich, S

    2007-02-12

    The organic constituents of historical vanishes from two ancient Italian lutes and a Stradivari violin, kept in the Musée de la musique in Paris, have been characterized using gas chromatography-mass spectrometry. Results have been compared with the chromatograms and mass spectra of recent as well as old naturally aged reference materials. The three historical varnishes analyzed have been shown to be oil varnishes, probably mixtures of linseed oil with resins. Identification of diterpenoids and triterpenoids compounds, and of the resins that may have been ingredients of the varnishes, are discussed in this paper.

  18. Synthesis, cytotoxicity and haemolytic activity of Pulsatilla saponin A, D derivatives.

    Science.gov (United States)

    Chen, Zhong; Duan, Huaqing; Wang, Minglei; Han, Li; Liu, Yanli; Zhu, Yongming; Yang, Shilin

    2015-06-15

    The strong haemolytic activity of Pulsatilla saponin A (PSA), D (PSD) hampered their clinical development of antitumor agents. In order to solve this problem, C-28 position modification derivatives of PSA/PSD were synthesized. The cytotoxicity and haemolytic activity of these compounds were evaluated. Structure-activity relationship and structure-toxicity relationship had been observed. The mice acute toxicity of compound 11 was reduced greatly than that of PSA. This study indicates that compound 11 may represent an interesting class of potent antitumor agents from triterpenoid saponins avoiding the haemolysis problem. The present study has important significance for the development of antitumor saponins. Copyright © 2015 Elsevier Ltd. All rights reserved.

  19. [Synthetic transformations of higher terpenoids. XXX. Synthesis and cytotoxic activity of betulonic acid amides with a piperidine or pyrrolidine nitroxide moiety].

    Science.gov (United States)

    Antimonova, A N; Petrenko, N I; Shults, E E; Polienko, Iu F; Shakirov, M M; Irtegova, I G; Pokrovskiĭ, M A; Sherman, K M; Grigor'ev, I A; Pokrovskiĭ, A G; Tolstikov, G A

    2013-01-01

    The reaction of betulonic acid chloride with 4-amino-2,2,6,6-tetramethylpeperidine-1-oxyl, 3-amino-2,2,5,5-tetramethylpyrrolidine-1-oxyl and 3-aminomethyl-2,2,5,5-tetramethylpyrrolidine-1-oxyl gave corresponding triterpenoid amides. It was found that new derivatives exhibit cytotoxic activity against tumor cells CEM-13, U-937, MT-4. CCID50 value for most activity compound--N-[3-oxolup-20(29)-en-30-yl]-(2,2,6,6-tetramethylpiperidine-4-yl)-1-oxyl--was 5.7-33.1 microM.

  20. Dirhamnosyl flavonoid and other constituents from Brillantaisia palisatii

    Energy Technology Data Exchange (ETDEWEB)

    Berrondo, Luciane Fatima; Gabriel, Felipe Teixeira; Fernandes, Sidney Bessa de; Menezes, Fabio de Sousa [Universidade Federal, Rio de Janeiro, RJ (Brazil). Faculdade de Farmacia. Dept. de Produtos Naturais e Alimentos]. E-mail: fsmenezes@pharma.ufrj.br; Moreira, Davyson de Lima [Universidade de Barra Mansa, RJ (Brazil). Faculdade de Farmacia

    2003-12-01

    A mixture containing sitosterol and stigmasterol; a new triterpene 3-epi-ursolic acid; another triterpene mixture comprising {alpha}-amyrin, {beta}-amyrin and lupeol; verbascoside, a phenylpropanoid glycoside; and lespedin, a glycosyl flavonoid, were isolated. The less polar compounds (steroids and triterpenoids) were isolated from the hexane partition of the crude ethanolic extract while the more polar ones (phenylpropanoid glycoside and glycosyl flavonoid) were isolated from the ethyl acetate partition of the same extract. The structures of all compounds were established using modern spectrometric methods of elucidation. The spectroscopic data of Lespedin, a rare dirhamnosylflavonol with hypotensor activity and of the triterpene, 3-epi-ursolic acid, are also reported. (author)

  1. Octadecanoides como reguladores de la defensa de las plantas

    OpenAIRE

    G. Camarena Gutiérrez

    2002-01-01

    En años recientes muchas moléculas lipoides muy potentes han sido identificadas, comprenden compuestos lipofílicos no derivados de lípidos como los brasinoesteroides triterpenoides, otros que parcialmente son de origen lipídico como los lipo-oligosacáridos, factores de nodulación de especies de Rhizobium que pueden tener parientes endógenos en las plantas, y un tercer grupo, los octadecanoides, cuyas estructuras son derivadas de ácidos grasos vegetales. Las señales mediadas por lípid...

  2. Aedes aegypti Larvicidal Sesquiterpene Alkaloids from Maytenus oblongata.

    Science.gov (United States)

    Touré, Seindé; Nirma, Charlotte; Falkowski, Michael; Dusfour, Isabelle; Boulogne, Isabelle; Jahn-Oyac, Arnaud; Coke, Maïra; Azam, Didier; Girod, Romain; Moriou, Céline; Odonne, Guillaume; Stien, Didier; Houël, Emeline; Eparvier, Véronique

    2017-02-24

    Four new sesquiterpene alkaloids (1-4) with a β-dihydroagrofuran skeleton and a new triterpenoid (5) were isolated from an ethyl acetate extract of Maytenus oblongata stems. Their structures were elucidated using 1D and 2D NMR spectroscopy as well as MS and ECD experiments. The M. oblongata stem EtOAc extract and the pure compounds isolated were tested for larvicidal activity against Aedes aegypti under laboratory conditions, and compounds 2 and 3 were found to be active.

  3. Two new 24-isopropenyl-lanostanoids from Tillandsia brachycaulos.

    Science.gov (United States)

    Cantillo-Ciau, Zulema; Mena-Rejón, Gonzalo J; Quintero-Mármol, Esther; Jiménez-Díaz, Antonio; Quijano, Leovigildo

    2003-01-01

    The leaves of Tillandsia brachycaulos afforded two novel tetracyclic triterpenoids identified as (24S)-24-isopropenyl-29-nor-5alpha-lanosta-7-en-3beta-ol (1) and (24S)-24-isopropenyl-29-nor-5alpha-lanosta-7-en-3-one (2), in addition to the known isopimaric acid (3) and chlorogenic acid (4). Their structures were elucidated on the basis of spectral analysis, including homo- and heteronuclear correlation NMR experiments (COSY, ROESY, HMQC and HMBC) and by comparison with data in the literature. The antimicrobial and antifungal activities were studied. The compounds did not show significant activity.

  4. Fermentation and purification strategies for the production of betulinic acid and its lupane-type precursors in Saccharomyces cerevisiae

    DEFF Research Database (Denmark)

    Czarnotta, Eik; Dianat, Mariam; Korf, Marcel

    2017-01-01

    from the bark of plane tree or birch. Here, we reengineered the reported betulinic acid pathway into S. cerevisiae and used this novel strain to develop efficient fermentation and product purification methods. Fed-batch cultivations with ethanol excess, using either an ethanol-pulse feed or controlling...... a constant ethanol concentration in the fermentation medium, significantly enhanced production of betulinic acid and its triterpenoid precursors. The beneficial effect of excess ethanol was further exploited in nitrogen-limited resting cell fermentations, yielding betulinic acid concentrations of 182 mg...

  5. Chemical constituents from Piper wallichii.

    Science.gov (United States)

    Shi, Yan-Ni; Yang, Lian; Zhao, Jin-Hua; Shi, Yi-Ming; Qu, Yan; Zhu, Hong-Tao; Wang, Dong; Yang, Chong-Ren; Li, Xing-Cong; Xu, Min; Zhang, Ying-Jun

    2015-01-01

    Fifteen known compounds including four triterpenoids (1-4), one sterol (5), one diketopiperazine alkaloid (6) and nine phenolics (7-15) were isolated from the stems of Piper wallichii. Their structures were elucidated by means of spectroscopic analysis, and acidic hydrolysis in case of the 2-oxo-3β,19α,23-trihydroxyurs-12-en-28-oic acid β-D-glucopyranosyl ester (1). The structure of compound 1 was fully assigned by 1D and 2D NMR experiments for the first time. All isolates were tested for their antibacterial, antifungal, anti-inflammatory and antiplatelet aggregation bioactivities.

  6. Microbial transformation of hederagenin by Cunninghamella echinulate, Mucor subtilissimus, and Pseudomonas oleovorans.

    Science.gov (United States)

    Liu, Zhen; Lu, Yan-Hua; Feng, Xu; Zou, Ying-Xin; Diao, Zhuo; Chu, Zhi-Yong

    2017-07-01

    The pentacyclic triterpenoid hederagenin (1) was subjected to biotransformation by Cunninghamella echinulate CGMCC 3.2000, Mucor subtilissimus CGMCC 3.2454 and Pseudomonas oleovorans CGMCC 1.1641. Three metabolites were obtained. On the basis of nuclear magnetic resonance and high-resolution mass spectral analyses, their structures were characterized as 3β, 23-dihydroxyolean-12-en-28-oic acid 28-O-β-D-glucopyranosyl ester (2), 3β, 15α, 23-trihydroxyolean-12-en-28-oic acid (3), 1β, 3β, 23-trihydroxyolean-12-en-28-oic acid (4), and metabolite (3) was a new compound. This was the first report on the biotransformation of hederagenin.

  7. Resorcinol derivatives from Ardisia maculosa.

    Science.gov (United States)

    Zheng, Ying; Wu, Feng-E

    2007-01-01

    Besides a series of known sterols and triterpenoids, a new resorcinol (1) and a known resorcinol (2) have been isolated from ethanol extract of Ardisia maculosa for the first time. The structures of these resorcinol derivatives were elucidated as 2-methyl-5-(Z-heptadec-8-enyl) resorcinol and 5-Z-heptadec-8-enyl) resorcinol by HRESI-MS, NMR ((1)H, (13)C, HSQC, HMBC) experiments. In our in vitro assay, compounds 1 and 2 showed no antimicrobial activities, however, compound 2 exhibited cytotoxity activity against human cancer cell line with GI(50) value of 2.14 x 10(- 4) mmol/ml.

  8. Antitumour, Antimicrobial, Antioxidant and Antiacetylcholinesterase Effect of Ganoderma Lucidum Terpenoids and Polysaccharides: A Review.

    Science.gov (United States)

    Cör, Darija; Knez, Željko; Knez Hrnčič, Maša

    2018-03-13

    Ganoderma lucidum (Reishi) is a popular medicinal mushroom and has been used in oriental medicine because of its promoting effects on health and life expectancy. G. lucidum contains various compounds with a high grade of biological activty, which increase the immunity and show antitumour, antimicrobial, anti-inflammatory, antioxidant and acetylcholinesterase inhibitory activity. Several of these substances belong to the triterpenoids and polysaccharides classes. Proteins, lipids, phenols, sterols, etc. are also present. In the present review, an extensive overview of the presence of antitumour, antimicrobial, antioxidant and antiacetylcholinesterase compounds in G. lucidum extracts will be given, along with an evaluation of their therapeutic effects.

  9. Antitumour, Antimicrobial, Antioxidant and Antiacetylcholinesterase Effect of Ganoderma Lucidum Terpenoids and Polysaccharides: A Review

    Directory of Open Access Journals (Sweden)

    Darija Cör

    2018-03-01

    Full Text Available Ganoderma lucidum (Reishi is a popular medicinal mushroom and has been used in oriental medicine because of its promoting effects on health and life expectancy. G. lucidum contains various compounds with a high grade of biological activty, which increase the immunity and show antitumour, antimicrobial, anti-inflammatory, antioxidant and acetylcholinesterase inhibitory activity. Several of these substances belong to the triterpenoids and polysaccharides classes. Proteins, lipids, phenols, sterols, etc. are also present. In the present review, an extensive overview of the presence of antitumour, antimicrobial, antioxidant and antiacetylcholinesterase compounds in G. lucidum extracts will be given, along with an evaluation of their therapeutic effects.

  10. Direct 13C NMR Detection in HPLC Hyphenation Mode

    DEFF Research Database (Denmark)

    Wubshet, Sileshi Gizachew; Johansen, Kenneth; Nyberg, Nils

    2012-01-01

    Solid phase extraction (SPE) was introduced as a crucial step in the HPLC-SPE-NMR technique to enable online analyte enrichment from which proton-detected NMR experiments on submicrogram amounts from complex mixtures were possible. However, the significance of direct-detected (13)C NMR experiments...... application of HPLC-SPE-NMR analysis using direct-detected (13)C NMR spectra. HPLC column loading, accumulative SPE trappings, and the effect of different elution solvents were evaluated and optimized. A column loading of approximately 600 mug of a prefractionated triterpenoid mixture, six trappings...

  11. 1H and 13C NMR spectral data of new saponins from Cordia piauhiensis.

    Science.gov (United States)

    Santos, Renata P; Silveira, Edilberto R; Uchôa, Daniel Esdras de A; Pessoa, Otília Deusdênia L; Viana, Francisco Arnaldo; Braz-Filho, Raimundo

    2007-08-01

    Two new bidesmoside triterpenoid saponins were isolated from stems of Cordia piauhiensis. Their structures, characterized as 3-O-alpha-L-rhamnopyranosyl-(1 --> 2)-beta-D-glucopyranosyl pomolic acid 28-O-beta-D-glucopyranosyl ester (1) and 3-O-alpha-L-rhamnopyranosyl-(1 --> 2)-beta-D-glucopyranosyl oleanolic acid 28-O-beta-D-glucopyranosyl-(1 --> 6)-beta-D-glucopyranosyl ester (2), were unequivocally established after extensive NMR (1H, 13C, DEPT 135 degrees, COSY, HSQC, HMBC, TOCSY, and NOESY) studies. Copyright 2007 John Wiley & Sons, Ltd.

  12. Actividad antifúngica de extractos de biomasa celular de neem sobre aislamientos de dermatofitos

    OpenAIRE

    Ospina Salazar, Daniel Iván; Hoyos Sánchez, Rodrigo Alberto; Arango Arteaga, Myrtha; Orozco Sánchez, Fernando; Ríos Salazar, Jhon Diego

    2014-01-01

    Título en español: Actividad antifúngica de extractos de biomasa celular de neem sobre aislamientos de dermatofitos Título en ingles: Antifungal activity of neem cellular biomass extracts on dermatophytes isolates Título corto: Actividad antifúngica de extractos de biomasa celular de neem Resumen:  Las líneas celulares de neem (Azadirachta indica A. Juss.) cultivadas en suspensión líquida han demostrado producir metabolitos secundarios bioactivos, particularmente triterpenoides. E...

  13. Current Advances in the Antimicrobial Potential of Species of Genus Ganoderma (Higher Basidiomycetes) against Human Pathogenic Microorganisms (Review).

    Science.gov (United States)

    Rai, Mahendra K; Gaikwad, Swapnil; Nagaonkar, Dipali; dos Santos, Carolina Alves

    2015-01-01

    Ganoderma spp. are very important therapeutic mushrooms and have been used traditionally for 4000 years in the treatment of various human disorders. Different species of Ganoderma possess bioactive compounds, which have already demonstrated antiviral, antibacterial, and antifungal activities. Various bioactive compounds such as triterpenoids, colossolactones, and polysaccharides, which are responsible for the antimicrobial potential of the genus, are discussed here in detail. Some Ganoderma spp. have been reported to be potential agents for the synthesis of metal nanoparticles. These nanoparticles have demonstrated antimicrobial activity and also are reviewed herein. The main aim of this review is to discuss the possible use of Ganoderma extracts and their active principles in antimicrobial therapy.

  14. Ganoderma pfeifferi--A European relative of Ganoderma lucidum.

    Science.gov (United States)

    Lindequist, Ulrike; Jülich, Wolf-Dieter; Witt, Sabine

    2015-06-01

    In contrast to well-studied and broadly used Ganoderma species, such as Ganoderma lucidum and Ganoderma applanatum, knowledge regarding Ganoderma pfeifferi is very limited. Herein is an overview of the phytochemistry, biological activities and possible applications of this mushroom species. In addition to triterpenoids and polysaccharides, G. pfeifferi contains unique sesquiterpenoids and other small molecular weight compounds. Some of these compounds exhibit remarkable antimicrobial activities in vitro and in vivo against multi-resistant bacteria, such as MRSA. Antiviral properties, UV-protection abilities and other activities are also known. Potential issues arising from the conversion of research results into practical applications are discussed. Copyright © 2015 Elsevier Ltd. All rights reserved.

  15. Transcriptome analysis of Panax vietnamensis var. fuscidicus discovers putative ocotillol-type ginsenosides biosynthesis genes and genetic markers.

    Science.gov (United States)

    Zhang, Guang-Hui; Ma, Chun-Hua; Zhang, Jia-Jin; Chen, Jun-Wen; Tang, Qing-Yan; He, Mu-Han; Xu, Xiang-Zeng; Jiang, Ni-Hao; Yang, Sheng-Chao

    2015-03-08

    P. vietnamensis var. fuscidiscus, called "Yesanqi" in Chinese, is a new variety of P. vietnamensis, which was first found in Jinping County, the southern part of Yunnan Province, China. Compared with other Panax plants, this species contains higher content of ocotillol-type saponin, majonoside R2. Despite the pharmacological importance of ocotillol-type saponins, little is known about their biosynthesis in plants. Hence, P. vietnamensis var. fuscidiscus is a suitable medicinal herbal plant species to study biosynthesis of ocotillol-type saponins. In addition, the available genomic information of this important herbal plant is lacking. To investigate the P. vietnamensis var. fuscidiscus transcriptome, Illumina HiSeq™ 2000 sequencing platform was employed. We produced 114,703,210 clean reads, assembled into 126,758 unigenes, with an average length of 1,304 bp and N50 of 2,108 bp. Among these 126,758 unigenes, 85,214 unigenes (67.23%) were annotated based on the information available from the public databases. The transcripts encoding the known enzymes involved in triterpenoid saponins biosynthesis were identified in our Illumina dataset. A full-length cDNA of three Squalene epoxidase (SE) genes were obtained using reverse transcription PCR (RT-PCR) and the expression patterns of ten unigenes were analyzed by reverse transcription quantitative real-time PCR (RT-qPCR). Furthermore, 15 candidate cytochrome P450 genes and 17 candidate UDP-glycosyltransferase genes most likely to involve in triterpenoid saponins biosynthesis pathway were discovered from transcriptome sequencing of P. vietnamensis var. fuscidiscus. We further analyzed the data and found 21,320 simple sequence repeats (SSRs), 30 primer pairs for SSRs were randomly selected for validation of the amplification and polymorphism in 13 P. vietnamensis var. fuscidiscus accessions. Meanwhile, five major triterpene saponins in roots of P. vietnamensis var. fuscidicus were determined using high performance

  16. Phytochemicals and bioactivities of Anemone raddeana Regel: a review.

    Science.gov (United States)

    Sun, Yong-Xu; Liu, Ji-Cheng; Liu, Da-You

    2011-11-01

    Anemone raddeana, usually called as'"Toujian Liang" in China, is an Anemone herb belonging to the Ranunculaceae family. Until now there are in total 67 of chemical components identified including triterpenoids, steroids, lactones, fats and oils, saccharide and alkaloids. A broad spectrum of pharmacological activity of A. raddeana compounds have been reported, such as antitumor, antimicrobial, anti-inflammatory, sedative and analgesic activites, as well as anti-convulsant and anti-histamine effects. In view of this, we initiated this short review to present the phytochemical and pharmacological profile of A. raddeana to support future studies in this discipline.

  17. Rationale and trial design of Bardoxolone Methyl Evaluation in Patients with Chronic Kidney Disease and Type 2 Diabetes

    DEFF Research Database (Denmark)

    de Zeeuw, Dick; Akizawa, Tadao; Agarwal, Rajiv

    2013-01-01

    Chronic kidney disease (CKD) associated with type 2 diabetes mellitus constitutes a global epidemic complicated by considerable renal and cardiovascular morbidity and mortality, despite the provision of inhibitors of the renin-angiotensin-aldosterone system (RAAS). Bardoxolone methyl, a synthetic...... triterpenoid that reduces oxidative stress and inflammation through Nrf2 activation and inhibition of NF-κB was previously shown to increase estimated glomerular filtration rate (eGFR) in patients with CKD associated with type 2 diabetes mellitus. To date, no antioxidant or anti-inflammatory therapy has proved...

  18. An updated review on pharmacological activities and phytochemical constituents of evening primrose (genus Oenothera

    Directory of Open Access Journals (Sweden)

    Rebecca Munir

    2017-11-01

    Full Text Available Genus Oenothera includes medicinal plants that are distributed throughout the world and are known since ancient times. Popular indications of different species of this genus include treatment of inflammations, diabetes, microbial infections, ulcers, tumors, kidney and liver problems. The plants of this genus are a botanical source for various pharmaceutically active components like sterols, alkaloids, phenolic acids, flavonoids, triterpenoids, saponins, biflavonols and tocopherols. This review article is a compilation of chemical composition and biological activities of the various species of the genus Oenothera.

  19. Comparison of the Apoptotic Effects of Supercritical Fluid Extracts of Antrodia cinnamomea Mycelia on Hepatocellular Carcinoma Cells

    Directory of Open Access Journals (Sweden)

    Hsiu-Man Lien

    2014-06-01

    Full Text Available Antrodia cinnamomea (AC has been widely used as a folk medicine in the prevention and treatment of liver diseases, such as hepatitis, hepatic fibrosis, and hepatocellular carcinoma. Previous studies have indicated that triterpenoids and benzenoids show selective cytotoxicity against human hepatoma cell lines. The aim of the study was to compare the triterpenoid content of extract and the extract-induced cytotoxicity in HepG2 cells from mycelia extracts of solid state cultured AC obtained by supercritical fluid extraction (SFE and the conventional solvent extraction method. SFE with CO2 mixed with a constant amount of ethanol co-solvent (10% of CO2 volume applied at different temperatures and pressures (40, 60 and 80 °C and, 20.7, 27.6 and 34.5 Mpa was also compared in the study. Although the extraction yield of triterpenoids (59.7 mg/g under the optimal extraction conditions of 34.5 MPa (5000 psi/60 °C (designated as sample S-5000-60 was equivalent to the extraction yield using conventional liquid solvent extraction with ethanol (ETOH-E at room temperature (60.33 mg/g, the cytotoxicity of the former against the proliferation of HepG2 cell line measured as the inhibition of 50% of cell growth activity (IC50 at dosages of 116.15, 57.82 and 43.96 µg/mL was superior to that of EtOH-E at 131.09, 80.04 and 48.30 µg/mL at 24, 48 and 72 h, respectively. Additionally, we further proved that the apoptotic effect of S-5000-60 presented a higher apoptosis ratio (21.5% than ETOH-E (10.5% according to annexin V-FITC and propidium iodide double staining assay results. The high affinity and selectivity of SFE on bioactive components resulted in a higher extraction efficiency than conventional solvent extraction. The chemical profile of the obtained extracts from solid state cultivated mycelium of AC was also determined by high-performance liquid chromatography electrospray ionization tandem mass spectrometry (LC-MS/MS, whereby three benzenoids and four

  20. Chemical Investigation of Euphorbia schimperi C. Presl

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    Azza R. Abdel-Monem

    2008-08-01

    Full Text Available Three triterpenoids; cycloart-25-en-3β,24-diol, cycloart-23-en-3β,25-diol, and a -amyrin, in addition to b -sitosterol- b -D-O-glucoside, scopoletin, luteolin and kampferol were isolated for the first time from the chloroform fraction of the alcoholic extract of Euphorbia schimperi C. Presl (F. Euphorbiaceae. The isolated compounds were identified using different spectroscopic methods (EIMS, 1HNMR, 13CNMR, HMQC, HMBC and COSY. The cytotoxic activity of the chloroform fraction was also studied using brain and breast carcinoma cell lines.

  1. A dicyanotriterpenoid induces cytoprotective enzymes and reduces multiplicity of skin tumors in UV-irradiated mice

    International Nuclear Information System (INIS)

    Dinkova-Kostova, Albena T.; Jenkins, Stephanie N.; Wehage, Scott L.; Huso, David L.; Benedict, Andrea L.; Stephenson, Katherine K.; Fahey, Jed W.; Liu Hua; Liby, Karen T.; Honda, Tadashi; Gribble, Gordon W.; Sporn, Michael B.; Talalay, Paul

    2008-01-01

    Inducible phase 2 enzymes constitute a primary line of cellular defense. The oleanane dicyanotriterpenoid 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-onitrile (TP-225) is a very potent inducer of these systems. Topical application of TP-225 to SKH-1 hairless mice increases the levels of NAD(P)H-quinone acceptor oxidoreductase 1 (NQO1) and heme oxygenase 1 (HO-1) and protects against UV radiation-induced dermal thickening. Daily topical treatments of 10 nmol of TP-225 to the backs of mice that were previously subjected to low-level chronic UVB radiation (30 mJ/cm 2 /session, twice a week for 17 weeks), led to 50% reduction in multiplicity of skin tumors. In addition, the total tumor burden of squamous cell carcinomas was reduced by 5.5-fold. The identification of new agents for protection against UV radiation-induced skin cancer and understanding of their mechanism(s) of action is especially important in view of the fact that human skin cancers represent a significant source of increasing morbidity and mortality

  2. [Synthesis and biological activity of 2,3-secotriterpene acid mono- and diamides].

    Science.gov (United States)

    Tolmacheva, I A; Igosheva, E V; Vikharev, Iu B; Grishko, V V; Savinova, O V; Boreko, E I; Eremin, V F

    2013-01-01

    Four types of amide (C3; C28; C3-C28) conjugates based on 2,3-seco-18alphaH-oleanane and 2,3-secolupane mono- and dicarboxylic acids were synthesized. The range of diamide derivatives was supplemented with C3-C3' and C28-C28' dicondensed amides with two A-secotriterpene backbones educed by reacting monocarboxylic A-secoacids with biogenic amino acid lysine. Compounds with inhibitory action against herpes virus reproduction (EC50 8.7 and 4.1 McM) were found among the synthesized mono- and diamide derivatives containing an ethyl-beta-alaninate fragment. It has been ascertained that diamide with ethyl-beta-alaninate fragment combines anti-herpes virus properties and anti-HIV activity (EC50 5.1 McM). For active compounds, the maximum non-toxic concentration (MNTC)/EC50 ratios ranges from 9.7 to 40.8. The synthesized amide conjugates do not exhibit any marked cytotoxic effects against human tumor cell lines rabdomiosarcoma RD TE32, A549 lung carcinoma and melanoma MS.

  3. The Antiproliferative Effect of Chakasaponins I and II, Floratheasaponin A, and Epigallocatechin 3-O-Gallate Isolated from Camellia sinensis on Human Digestive Tract Carcinoma Cell Lines

    Directory of Open Access Journals (Sweden)

    Niichiro Kitagawa

    2016-11-01

    Full Text Available Acylated oleanane-type triterpene saponins, namely chakasaponins I (1 and II (2, floratheasaponin A (3, and their analogs, together with catechins—including (–-epigallocatechin 3-O-gallate (4, flavonoids, and caffeine—have been isolated as characteristic functional constituents from the extracts of “tea flower”, the flower buds of Camellia sinensis (Theaceae, which have common components with that of the leaf part. These isolates exhibited antiproliferative activities against human digestive tract carcinoma HSC-2, HSC-4, MKN-45, and Caco-2 cells. The antiproliferative activities of the saponins (1–3, IC50 = 4.4–14.1, 6.2–18.2, 4.5–17.3, and 19.3–40.6 µM, respectively were more potent than those of catechins, flavonoids, and caffeine. To characterize the mechanisms of action of principal saponin constituents 1–3, a flow cytometric analysis using annexin-V/7-aminoactinomycin D (7-AAD double staining in HSC-2 cells was performed. The percentage of apoptotic cells increased in a concentration-dependent manner. DNA fragmentation and caspase-3/7 activation were also detected after 48 h. These results suggested that antiproliferative activities of 1–3 induce apoptotic cell death via activation of caspase-3/7.

  4. Triterpene saponin hemi-biosynthesis of a leaf beetle's (Platyphora kollari) defensive secretion

    Science.gov (United States)

    Ghostin, Jean; Habib-Jiwan, Jean-Louis; Rozenberg, Raoul; Daloze, Désiré; Pasteels, Jacques M.; Braekman, Jean-Claude

    2007-07-01

    The adults of the leaf beetle Platyphora kollari (Chrysomelidae) are able to metabolise the oleanane triterpene β-amyrin (1) into the glycoside 3-O-β-d-glucopyranosyl-(1→4)-β-d-glucuronopyranosyl-hederagenin (2) that is stored in their defensive glands. The aim of this study was to test the hypothesis that oleanolic acid (3) is an intermediate in the conversion of 1 into 2 and to check whether the sequestration of pentacyclic triterpenes is selective in favour of β-amyrin (1). To this end, adults of P. kollari were fed with Ipomoea batatas leaf disks painted with a solution of [2,2,3-2H3]oleanolic acid or [2,2,3-2H3]α-amyrin and the secretion of their defensive glands analysed by HPLC ESIMS. The data presented in this work indicated that the first step of the transformation of β-amyrin (1) into the sequestered glycoside 2 is its oxidation into oleanolic acid (3) and that this conversion is selective but not specific in favour of β-amyrin (1).

  5. Transcriptomic analysis of Siberian ginseng (Eleutherococcus senticosus) to discover genes involved in saponin biosynthesis.

    Science.gov (United States)

    Hwang, Hwan-Su; Lee, Hyoshin; Choi, Yong Eui

    2015-03-14

    Eleutherococcus senticosus, Siberian ginseng, is a highly valued woody medicinal plant belonging to the family Araliaceae. E. senticosus produces a rich variety of saponins such as oleanane-type, noroleanane-type, 29-hydroxyoleanan-type, and lupane-type saponins. Genomic or transcriptomic approaches have not been used to investigate the saponin biosynthetic pathway in this plant. In this study, de novo sequencing was performed to select candidate genes involved in the saponin biosynthetic pathway. A half-plate 454 pyrosequencing run produced 627,923 high-quality reads with an average sequence length of 422 bases. De novo assembly generated 72,811 unique sequences, including 15,217 contigs and 57,594 singletons. Approximately 48,300 (66.3%) unique sequences were annotated using BLAST similarity searches. All of the mevalonate pathway genes for saponin biosynthesis starting from acetyl-CoA were isolated. Moreover, 206 reads of cytochrome P450 (CYP) and 145 reads of uridine diphosphate glycosyltransferase (UGT) sequences were isolated. Based on methyl jasmonate (MeJA) treatment and real-time PCR (qPCR) analysis, 3 CYPs and 3 UGTs were finally selected as candidate genes involved in the saponin biosynthetic pathway. The identified sequences associated with saponin biosynthesis will facilitate the study of the functional genomics of saponin biosynthesis and genetic engineering of E. senticosus.

  6. Diospyros, an under-utilized, multi-purpose plant genus: A review.

    Science.gov (United States)

    Rauf, Abdur; Uddin, Ghias; Patel, Seema; Khan, Ajmal; Halim, Sobia Ahsan; Bawazeer, Saud; Ahmad, Khalid; Muhammad, Naveed; Mubarak, Mohammad S

    2017-07-01

    The genus Diospyros from family Ebenaceae has versatile uses including edible fruits, valuable timber, and ornamental uses. The plant parts of numerous species have been in use as remedies in various folk healing practices, which include therapy for hemorrhage, incontinence, insomnia, hiccough, diarrhea etc. Phytochemical constituents such as terpenoids, ursanes, lupanes, polyphenols, tannins, hydrocarbons, and lipids, benzopyrones, naphthoquinones, oleananes, and taraxeranes have been isolated from different species of this genus. The biological activities of these plants such as antioxidant, anti-inflammatory, analgesic, antipyretic, anti-diabetic, antibacterial, anthelmintic, antihypertensive, cosmeceutical, enzyme-inhibitory etc. have been validated by means of an in vitro, in vivo, and clinical tests. As a rich reserve of pharmacologically important components, this genus can accelerate the pace of drug discovery. Accordingly, the aim of the present review is to survey and summarize the recent literature pertaining to the medicinal and pharmacological uses of Diospyros, and to select experimental evidence on the pharmacological properties of this genus. In addition, the review also aims at identifying areas that need development to make use of this genus, especially its fruit and phytochemicals as means for economic development and for drug discovery. Copyright © 2017 Elsevier Masson SAS. All rights reserved.

  7. Organic geochemical investigation and coal-bed methane characteristics of the Guasare coals (Paso Diablo mine, western Venezuela)

    Science.gov (United States)

    Quintero, K.; Martinez, M.; Hackley, P.; Marquez, G.; Garban, G.; Esteves, I.; Escobar, M.

    2011-01-01

    The aim of this work was to carry out a geochemical study of channel samples collected from six coal beds in the Marcelina Formation (Zulia State, western Venezuela) and to determine experimentally the gas content of the coals from the Paso Diablo mine. Organic geochemical analyses by gas chromatography-mass spectrometry and isotopic analyses on-line in coalbed gas samples were performed. The results suggest that the Guasare coals were deposited in a continental environment under highly dysoxic and low salinity conditions. The non-detection of 18??(H)-oleanane does not preclude that the organic facies that gave rise to the coals were dominated by angiosperms. In addition, the presence of the sesquiterpenoid cadalene may indicate the subordinate contribution of gymnosperms (conifers) in the Paleocene Guasare mire. The average coalbed gas content obtained was 0.6 cm3/g. ??13C and D values indicate that thermogenic gas is prevalent in the studied coals. Copyright ?? Taylor & Francis Group, LLC.

  8. Inhibition of Helicobacter pylori CagA-Induced Pathogenesis by Methylantcinate B from Antrodia camphorata

    Directory of Open Access Journals (Sweden)

    Chun-Jung Lin

    2013-01-01

    Full Text Available The bacterial pathogen Helicobacter pylori (Hp is the leading risk factor for the development of gastric cancer. Hp virulence factor, cytotoxin-associated gene A (CagA interacted with cholesterol-enriched microdomains and leads to induction of inflammation in gastric epithelial cells (AGS. In this study, we identified a triterpenoid methylantcinate B (MAB from the medicinal mushroom Antrodia camphoratawhich inhibited the translocation and phosphorylation of CagA and caused a reduction in hummingbird phenotype in HP-infected AGS cells. Additionally, MAB suppressed the Hp-induced inflammatory response by attenuation of NF-κB activation, translocation of p65 NF-κB, and phosphorylation of IκB-α, indicating that MAB modulates CagA-mediated signaling pathway. Additionally, MAB also suppressed the IL-8 luciferase activity and its secretion in HP-infected AGS cells. On the other hand, molecular structure simulations revealed that MAB interacts with CagA similarly to that of cholesterol. Moreover, binding of cholesterol to the immobilized CagA was inhibited by increased levels of MAB. Our results demonstrate that MAB is the first natural triterpenoid which competes with cholesterol bound to CagA leading to attenuation of Hp-induced pathogenesis of epithelial cells. Thus, this study indicates that MAB may have a scope to develop as a therapeutic candidate against Hp CagA-induced inflammation.

  9. The Effectiveness of Local Plants from Lom and Sawang Ethnics as Antimalarial Medicine

    Directory of Open Access Journals (Sweden)

    Henny Helmi

    2016-09-01

    Full Text Available Native people or ethnic societies that live in endemic malaria islands such as in Bangka Island and Belitung Island have used many medicinal plants to cure malaria. Leaves of kesembung (Scaevola taccada (Gaertn Roxb, roots of kebentak (Wikstroemia androsaemofolia Decne, and roots of medang mencena (Dapniphyllum laurinum (Benth are the examples. This research was aimed to investigate the present of some biochemical compound and evaluate the antimalarial activity of ethanol extract of the plants against Plasmodium falciparum 3D7 in vitro. The IC50 level was determined through visual observation under microscope over 5000 of giemsa-stained erythrocytes then analyzed by probit analysis. Results showed that kebentak root ethanol extract was effective to inhibit P. falciparum 3D7 with level 0.485 µg/mL. Furthermore, the IC50 level of kesembung leaves and medang root were 44.352 µg/mL and 1486.678 µg/mL respectively. Phytochemical test result showed that kebentak leaf ethanol crude extract contained triterpenoid, kesembung root contained phenol and tannins; moreover, medang root contained alkaloid, saponin, and triterpenoid.How to CiteHelmi, H., Afriyansyah, B. & Ekasari, W. (2016. The Effectiveness of Local Plants from Lom and Sawang Ethnics as Antimalarial Medicine. Biosaintifika: Journal of Biology & Biology Education, 8(2, 193-200. 

  10. Bioactive Phytochemicals from Wild Arbutus unedo L. Berries from Different Locations in Portugal: Quantification of Lipophilic Components.

    Science.gov (United States)

    Fonseca, Daniela F S; Salvador, Ângelo C; Santos, Sónia A O; Vilela, Carla; Freire, Carmen S R; Silvestre, Armando J D; Rocha, Sílvia M

    2015-06-23

    The lipophilic composition of wild Arbutus unedo L. berries, collected from six locations in Penacova (center of Portugal), as well as some general chemical parameters, namely total soluble solids, pH, titratable acidity, total phenolic content and antioxidant activity was studied in detail to better understand its potential as a source of bioactive compounds. The chemical composition of the lipophilic extracts, focused on the fatty acids, triterpenoids, sterols, long chain aliphatic alcohols and tocopherols, was investigated by gas chromatography-mass spectrometry (GC-MS) analysis of the dichloromethane extracts. The lipophilic extractives of the ripe A. unedo berries ranged from 0.72% to 1.66% (w/w of dry weight), and consisted mainly of triterpenoids, fatty acids and sterols. Minor amounts of long chain aliphatic alcohols and tocopherols were also identified. Forty-one compounds were identified and among these, ursolic acid, lupeol, α-amyrin, linoleic and α-linolenic acids, and β-sitosterol were highlighted as the major components. To the best of our knowledge the current research study provides the most detailed phytochemical repository for the lipophilic composition of A. unedo, and offers valuable information for future valuation and exploitation of these berries.

  11. Antiproliferative and Antibacterial Activities of Cirsium scabrum from Tunisia

    Directory of Open Access Journals (Sweden)

    Ramla Sahli

    2017-01-01

    Full Text Available Several Cirsium species are known for their uses in traditional medicine and consequently are studied for their phytochemical content and their biological activities. In the framework of a previous study conducted on eight extremophile plants from Tunisia, we highlighted that the crude methanolic extract of C. scabrum, a not investigated thistle, showed moderate but quite selective cytotoxic activity against the cancerous cell line J774 compared to the noncancerous cell line WI38 (IC50 = 11.53 μg/ml on J774, IC50 = 29.89 µg/ml on WI38, and selectivity index = 2.6. In the current study, the partitions of the leaves of C. scabrum were analyzed for their antiproliferative activity on the same cell lines. From the most active petroleum ether partition, we isolated four triterpenoids including lupeol, taraxasterol acetate, and a (1 : 1 mixture of 25-hydroperoxycycloart-23-en-3β-ol and 24-hydroperoxycycloart-25-en-3β-ol. These two cycloartane-type triterpenoids are mostly responsible for this cytotoxic activity. On the other hand, the antimicrobial potential of this plant was also evaluated against 36 microorganisms. The moderate antibacterial activity against 6 Staphylococcus aureus and 2 Dermabacter hominis strains is mainly attributed to the butanol partition whose major compounds are glycosides of flavones.

  12. Antiproliferative and Antibacterial Activities of Cirsium scabrum from Tunisia.

    Science.gov (United States)

    Sahli, Ramla; Rivière, Céline; Dufloer, Cédric; Beaufay, Claire; Neut, Christel; Bero, Joanne; Hennebelle, Thierry; Roumy, Vincent; Ksouri, Riadh; Quetin-Leclercq, Joelle; Sahpaz, Sevser

    2017-01-01

    Several Cirsium species are known for their uses in traditional medicine and consequently are studied for their phytochemical content and their biological activities. In the framework of a previous study conducted on eight extremophile plants from Tunisia, we highlighted that the crude methanolic extract of C. scabrum , a not investigated thistle, showed moderate but quite selective cytotoxic activity against the cancerous cell line J774 compared to the noncancerous cell line WI38 (IC 50 = 11.53  μ g/ml on J774, IC 50 = 29.89  µ g/ml on WI38, and selectivity index = 2.6). In the current study, the partitions of the leaves of C. scabrum were analyzed for their antiproliferative activity on the same cell lines. From the most active petroleum ether partition, we isolated four triterpenoids including lupeol, taraxasterol acetate, and a (1 : 1) mixture of 25-hydroperoxycycloart-23-en-3 β -ol and 24-hydroperoxycycloart-25-en-3 β -ol. These two cycloartane-type triterpenoids are mostly responsible for this cytotoxic activity. On the other hand, the antimicrobial potential of this plant was also evaluated against 36 microorganisms. The moderate antibacterial activity against 6 Staphylococcus aureus and 2 Dermabacter hominis strains is mainly attributed to the butanol partition whose major compounds are glycosides of flavones.

  13. Identification of metabolic profiling of cell culture of licorice compared with its native one.

    Science.gov (United States)

    Man, Shuli; Guo, Songbo; Gao, Wenyuan; Wang, Juan; Zhang, Liming; Li, Xinglin

    2013-04-01

    Glycyrrhiza uralensis has long been used as a flavoring and sweetening agent in food products. In the last ten years, suspensions of Glycyrhiza cells have been successfully established. However, there is no report of full metabolic profiling research on these cells. To identify their composition we used HPLC-DAD coupled with ESI(+/-)-MS (n) to compare the constituents of cultured Glycyrhiza (CG) cells with those the native cells (NG). We identified 60 compounds including flavonoids, phenols, and triterpenoids. Among these compounds, 42 occurred both in NG and CG, nine were present in NG only and nine were present in CG alone. The number of the triterpenoid aglycones without glycones in CG was smaller than that in NG. The number of flavanone, isoflavone, isoflavan, and benzenoid compounds was also smaller in CG than that in NG, whereas the number of pterocarpans was much higher. Although differences existed between CG and NG, the extract of CG was similar to that of NG. With the development of cell suspension culture-based biotransformation, cell culture of Glycyrrhiza has the potential to be more profitable than field cultivation in some areas.

  14. Molecular Cloning and Characterization of PnbHLH1 Transcription Factor in Panax notoginseng

    Directory of Open Access Journals (Sweden)

    Xiang Zhang

    2017-07-01

    Full Text Available Panax notoginseng has been extensively used as a traditional Chinese medicine. In the current study, molecular cloning and characterization of PnbHLH1 transcription factor were explored in Panax notoginseng. The full length of the PnbHLH1 gene obtained by splicing was 1430 bp, encoding 321 amino acids. Prokaryotic expression vector pET-28a-PnbHLH1 was constructed and transferred into the BL21 prokaryotic expression strain. An electrophoretic mobility shift assay of PnbHLH1 protein binding to E-box cis-acting elements verified that PnbHLH1 belonged to the bHLH class transcription factor which could interact with the promoter region of the E-box core sequence. The expression levels of key genes involved in the biosynthesis of triterpenoid saponins in PnbHLH1 transgenic cells were higher than those in the wild cells. Similarly, the total saponin contents were increased in the PnbHLH1 transgenic cell lines compared with the wild cell lines. Such results suggest that the PnbHLH1 transcription factor is a positive regulator in the biosynthesis of triterpenoid saponins in Panax notoginseng.

  15. Hepatoprotective activity of sea cucumber Phyllophorus sp. extract in carp (Cyprinus carpio)

    Science.gov (United States)

    Sulmartiwi, Laksmi; Triastuti, Juni; Andriyono, Sapto; Umami, Mardiah Rahma

    2017-02-01

    Many procedures continuously in aquaculture and scientific research like tagging and vaccinating cause pain, involving damaging tissue and also cause stress responses in fish. Stress responses in fish influence liver because liver have vital role to supply energy and metabolism. Histology alteration in liver is caused by stress response like changes of vacuolation hepatocyte and characteristic colour. Triterpenoid was known had hepatoprotective activity. One of marine organism contained triterpenoid was sea cucumber. Result of research showed that liver tissue in fish with injected acetic acid 5 % (in upper lip) as pain stimulus have histopathology damages such as pyknosis (medium damage level) and oedema (heavy damage level) after 8 hour injection. Injected Lidocaine 1mg/fish as analgesic drug have histopathology damages such as oedema (heavy damages level), necrosis and pyknosis (low damages level). Injected acetic acid 5 % (in upper lip) and ethanolic extract of sea cucumber Phyllophorus sp. dose 5 mg/50 gr body weight shown histopathology damages such as necrosis, edema (medium damage level) and pyknosis (low damage level).

  16. Fruit cuticle lipid composition and fruit post-harvest water loss in an advanced backcross generation of pepper (Capsicum sp.)

    KAUST Repository

    Parsons, Eugene P.; Popopvsky, Sigal; Lohrey, Gregory T.; Lu, Shiyou; Alkalai-Tuvia, Sharon; Perzelan, Yaacov; Paran, Ilan; Fallik, Elazar; Jenks, Matthew A.

    2012-01-01

    To understand the role of fruit cuticle lipid composition in fruit water loss, an advanced backcross population, the BC2F2, was created between the Capsicum annuum (PI1154) and the Capsicum chinense (USDA162), which have high and low post-harvest water loss rates, respectively. Besides dramatic differences in fruit water loss, preliminary studies also revealed that these parents exhibited significant differences in both the amount and composition of their fruit cuticle. Cuticle analysis of the BC2F2 fruit revealed that although water loss rate was not strongly associated with the total surface wax amount, there were significant correlations between water loss rate and cuticle composition. We found a positive correlation between water loss rate and the amount of total triterpenoid plus sterol compounds, and negative correlations between water loss and the alkane to triterpenoid plus sterol ratio. We also report negative correlations between water loss rate and the proportion of both alkanes and aliphatics to total surface wax amount. For the first time, we report significant correlations between water loss and cutin monomer composition. We found positive associations of water loss rate with the total cutin, total C16 monomers and 16-dihydroxy hexadecanoic acid. Our results support the hypothesis that simple straight-chain aliphatic cuticle constituents form more impermeable cuticular barriers than more complex isoprenoid-based compounds. These results shed new light on the biochemical basis for cuticle involvement in fruit water loss. © 2012 Physiologia Plantarum.

  17. Analisis Kemiripan 20 Aksesi Temu Ireng (Curcuma aeruginosa Roxb. Berdasarkan Warna Rimpang, Hasil Ekstrak, dan Kandungan Fitokimia

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    Waras Nurcholis

    2017-01-01

    Full Text Available ABSTRACTCurcuma aeruginosa Roxb., popularly known as “temu ireng”, is considered as a potential source of medicinal plant for pharmacological activities. However, varieties of C. aeruginosa are still limited in Indonesia so it needs more accessions for improvement and development of new varieties. Rhizome colors, phytochemical contents and extract yield from 20 promising lines of C. aeruginosa were investigated by qualitative method for rhizome colors and phytochemical contents, and maceration method using 70% ethanol for yield extract. Similarity analysis was used for cluster analysis based on rhizome colors, phytochemical contents and yield extract. Blue was the color characterization of rhizome C. aeruginosa. The extract yield for 20 promising lines of C. aeruginosa varied from 7.92 to 19.71%, with KN and BH promising lines having the lowest and highest value, respectively. All promising lines of C. aeruginosa contain saponin and triterpenoid. Based on similarity analysis, all promising lines could be divided into 3 clusters. Cluster I consisted of 14 promising lines i.e. WG, SH, KA, GD, BH, KP, NW, PW, MB, PR, PT, KN, MD, and PK. Cluster II consisted of 4 promising lines i.e. LC, CB, KL, and GK. Cluster III consisted of 2 promising lines i.e. KD and SG. Keywords: promising lines, saponin, triterpenoid

  18. Characterization of Terpenoids from the Root of Ceriops tagal with Antifouling Activity

    Science.gov (United States)

    Chen, Jun-De; Yi, Rui-Zao; Lin, Yi-Ming; Feng, Dan-Qing; Zhou, Hai-Chao; Wang, Zhan-Chang

    2011-01-01

    One new dimeric diterpenoid, 8(14)-enyl-pimar-2′(3′)-en-4′(18′)-en-15′(16′)-endolabr- 16,15,2′,3′-oxoan-16-one (1) and five known terpenoids: Tagalsin C (2), Tagalsin I (3), lup-20(29)-ene-3β,28-diol (4), 3-oxolup-20(29)-en-28-oic acid (5) and 28-hydroxylup- 20(29)-en-3-one (6) were isolated from the roots of the mangrove plant Ceriops tagal. Their structures and relative stereochemistry were elucidated by means of extensive NMR, IR and MS analysis. The antifouling activity against larval settlement of the barnacle Balanus albicostatus were evaluated using capsaicin as a positive control. All these terpenoids exhibited antifouling activity against cyprid larvae of the barnacle without significant toxicity. The structure-activity relationship results demonstrated that the order of antifouling activity was diterpenoid (Compound 2) > triterpenoid (Compounds 4, 5 and 6) > dimeric diterpenoid (Compounds 1 and 3). The functional groups on the C-28 position of lupane triterpenoid significantly affect the antifouling activity. The diterpenoid dimmer with two identical diterpenoid subunits might display more potent antifouling activity than one with two different diterpenoid subunits. The stability test showed that Compounds 2, 4, 5 and 6 remained stable over 2-month exposure under filtered seawater. PMID:22072902

  19. Trypanocidal constituents in plants: 7. Mammea-type coumarins

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    Ricardo Reyes-Chilpa

    2008-08-01

    Full Text Available Calophyllum brasiliense and Mammea americana (Clusiaceae are two trees from the tropical rain forests of the American continent. A previous screening showed high trypanocidal activity in the extracts of these species. Several mammea-type coumarins, triterpenoids and biflavonoids were isolated from the leaves of C. brasiliense. Mammea A/AA was obtained from the fruit peels of M. americana. These compounds were tested in vitro against epimastigotes and trypomastigotes of Trypanosoma cruzi, the etiologic agent of Chagas disease. The most potent compounds were mammea A/BA, A/BB, A/AA, A/BD and B/BA, with MC100 values in the range of 15 to 90 g/ml. Coumarins with a cyclized ,-dimethylallyl substituent on C-6, such as mammea B/BA, cyclo F + B/BB cyclo F, and isomammeigin, showed MC100 values > 200 g/ml. Several active coumarins were also tested against normal human lymphocytes in vitro, which showed that mammea A/AA and A/BA were not toxic. Other compounds from C. brasiliense, such as the triterpenoids, friedelin, canophyllol, the biflavonoid amentoflavone, and protocatechuic and shikimic acids, were inactive against the epimastigotes. The isopropylidenedioxy derivative of shikimic acid was inactive, and its structure was confirmed by X-ray diffraction. Our results suggest that mammea-type coumarins could be a valuable source of trypanocidal compounds.

  20. High-Performance Liquid Chromatography with Diode Array Detector and Electrospray Ionization Ion Trap Time-of-Flight Tandem Mass Spectrometry to Evaluate Ginseng Roots and Rhizomes from Different Regions.

    Science.gov (United States)

    Wang, Hong-Ping; Zhang, You-Bo; Yang, Xiu-Wei; Yang, Xin-Bao; Xu, Wei; Xu, Feng; Cai, Shao-Qing; Wang, Ying-Ping; Xu, Yong-Hua; Zhang, Lian-Xue

    2016-05-09

    Ginseng, Panax ginseng C. A. Meyer, is an industrial crop in China and Korea. The functional components in ginseng roots and rhizomes are characteristic ginsenosides. This work developed a new high-performance liquid chromatography coupled with electrospray ionization ion trap time-of-flight multistage mass spectrometry (LC-ESI-IT-TOF-MS(n)) method to identify the triterpenoids. Sixty compounds (1-60) including 58 triterpenoids were identified from the ginseng cultivated in China. Substances 1, 2, 7, 15-20, 35, 39, 45-47, 49, 55-57, 59, and 60 were identified for the first time. To evaluate the quality of ginseng cultivated in Northeast China, this paper developed a practical liquid chromatography-diode array detection (LC-DAD) method to simultaneously quantify 14 interesting ginsenosides in ginseng collected from 66 different producing areas for the first time. The results showed the quality of ginseng roots and rhizomes from different sources was different due to growing environment, cultivation technology, and so on. The developed LC-ESI-IT-TOF-MS(n) method can be used to identify many more ginsenosides and the LC-DAD method can be used not only to assess the quality of ginseng, but also to optimize the cultivation conditions for the production of ginsenosides.

  1. Revisiting Terminalia arjuna – An Ancient Cardiovascular Drug

    Directory of Open Access Journals (Sweden)

    Shridhar Dwivedi

    2014-10-01

    Full Text Available Terminalia arjuna, commonly known as arjuna, belongs to the family of Combretaceae. Its bark decoction is being used in the Indian subcontinent for anginal pain, hypertension, congestive heart failure, and dyslipidemia, based on the observations of ancient physicians for centuries. The utility of arjuna in various cardiovascular diseases needs to be studied further. Therefore, the present review is an effort to give a detailed survey of the literature summarizing the experimental and clinical studies pertinent to arjuna in cardiovascular disorders, which were particularly performed during the last decade. Systematic reviews, meta-analyses, and clinical studies of arjuna were retrieved through the use of PubMed, Google Scholar, and Cochrane databases. Most of the studies, both experimental and clinical, have suggested that the crude drug possesses anti-ischemic, antioxidant, hypolipidemic, and antiatherogenic activities. Its useful phytoconstituents are: Triterpenoids, β-sitosterol, flavonoids, and glycosides. Triterpenoids and flavonoids are considered to be responsible for its beneficial antioxidant cardiovascular properties. The drug has shown promising effect on ischemic cardiomyopathy. So far, no serious side effects have been reported with arjuna therapy. However, its long-term safety still remains to be elucidated. Though it has been found quite useful in angina pectoris, mild hypertension, and dyslipidemia, its exact role in primary/secondary coronary prevention is yet to be explored.

  2. Oleanolic Acid and Its Derivatives: Biological Activities and Therapeutic Potential in Chronic Diseases

    Directory of Open Access Journals (Sweden)

    Taiwo Betty Ayeleso

    2017-11-01

    Full Text Available The increasing demand for natural products as an alternative therapy for chronic diseases has encouraged research into the pharmacological importance of bioactive compounds from plants. Recently, there has been a surge of interest in the therapeutic potential of oleanolic acid (OA in the prevention and management of chronic diseases. Oleanolic acid is a pentacyclic triterpenoid widely found in plants, including fruits and vegetables with different techniques and chromatography platforms being employed in its extraction and isolation. Several studies have demonstrated the potential therapeutic effects of OA on different diseases and their symptoms. Furthermore, oleanolic acid also serves as a framework for the development of novel semi-synthetic triterpenoids that could prove vital in finding therapeutic modalities for various ailments. There are recent advances in the design and synthesis of chemical derivatives of OA to enhance its solubility, bioavailability and potency. Some of these derivatives have also been therapeutic candidates in a number of clinical trials. This review consolidates and expands on recent reports on the biological effects of oleanolic acid from different plant sources and its synthetic derivatives as well as their mechanisms of action in in vitro and in vivo study models. This review suggests that oleanolic acid and its derivatives are important candidates in the search for alternative therapy in the treatment and management of chronic diseases.

  3. In silico investigation of cycloartane triterpene derivatives from Cimicifuga dahurica (Turcz.) Maxim. roots for the development of potent soluble epoxide hydrolase inhibitors.

    Science.gov (United States)

    Thao, Nguyen Phuong; Kim, Jang Hoon; Thuy Luyen, Bui Thi; Dat, Nguyen Tien; Kim, Young Ho

    2017-05-01

    In our search for natural soluble epoxide hydrolase (sEH) inhibitors from plants, we found that an ethanolic extract of the roots of Cimicifuga dahurica (Turcz.) Maxim. significantly inhibits sEH in vitro. A phytochemical study on the dichloromethane fraction of C. dahurica resulted in the isolation of two new cycloartane triterpenoids (1 and 6), together with 13 known cycloartane analogues (2-5 and 7-15). The structures of compounds were determined by spectroscopic methods. All of the triterpenoid derivatives inhibited sEH enzymatic activity in a concentration-dependent manner, and 13 of the tested compounds showed significant activity. Among them, compounds 1, 3, 5, 7, 9, and 12 showed the highest levels of inhibitory activity, with IC 50 values of about 5μM or less. Kinetic analysis of compounds 1, 3, 5-9, 11, 12, and 14 revealed that compounds 3, 6, 7, 11, and 14 were non-competitive; 1, 5, 9, and 12 were mixed-type; and 8 was a competitive inhibitor. Furthermore, in silico molecular docking indicated that compounds 3, 6-9, 11, 12, and 14 bound to sEH in a similar manner and had stable binding energies, as calculated by AutoDock 4.2 and processed in a 10,000-ps molecular dynamics simulation to assess the binding stability of compounds 5, 7, and 9. Copyright © 2017 Elsevier B.V. All rights reserved.

  4. Bioactive Phytochemicals from Wild Arbutus unedo L. Berries from Different Locations in Portugal: Quantification of Lipophilic Components

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    Daniela F. S. Fonseca

    2015-06-01

    Full Text Available The lipophilic composition of wild Arbutus unedo L. berries, collected from six locations in Penacova (center of Portugal, as well as some general chemical parameters, namely total soluble solids, pH, titratable acidity, total phenolic content and antioxidant activity was studied in detail to better understand its potential as a source of bioactive compounds. The chemical composition of the lipophilic extracts, focused on the fatty acids, triterpenoids, sterols, long chain aliphatic alcohols and tocopherols, was investigated by gas chromatography–mass spectrometry (GC–MS analysis of the dichloromethane extracts. The lipophilic extractives of the ripe A. unedo berries ranged from 0.72% to 1.66% (w/w of dry weight, and consisted mainly of triterpenoids, fatty acids and sterols. Minor amounts of long chain aliphatic alcohols and tocopherols were also identified. Forty-one compounds were identified and among these, ursolic acid, lupeol, α-amyrin, linoleic and α-linolenic acids, and β-sitosterol were highlighted as the major components. To the best of our knowledge the current research study provides the most detailed phytochemical repository for the lipophilic composition of A. unedo, and offers valuable information for future valuation and exploitation of these berries.

  5. A new pentacyclic triterpene with potent antibacterial activity from Limnophila indica Linn. (Druce).

    Science.gov (United States)

    Brahmachari, Goutam; Mandal, Narayan C; Roy, Rajiv; Ghosh, Ranjan; Barman, Soma; Sarkar, Sajal; Jash, Shyamal K; Mondal, Sadhan

    2013-10-01

    A new pentacyclic triterpenoid constituent, characterized as 3-oxo-olean-12(13),18(19)-dien-29α-carboxylic acid (1) on the basis of detailed spectral studies, was isolated from the aerial parts and roots of Limnophila indica (Scrophulariaceae). Compound 1 exhibited considerable antibacterial activity against three Gram-positive bacteria viz. Bacillus subtilis, Staphylococcus aureus and Listeria monocytogenes (MICs within a range of 25-30 μg/ml) and moderate activity against four Gram-negative bacteria Salmonella typhimurium, Escherichia coli, Pseudomonas aeruginosa, and Pantoea ananatis (MICs within a range of 30-100 μg/ml). The plant pathogenic bacterium P. ananatis and human pathogenic S. typhimurium responded at comparatively higher concentrations of the compound 1, which were 75 and 100 μg/ml respectively. The compound inhibited the growth of Gram-positive B. subtilis and Gram-negative P. aeruginosa completely with a clear bactericidal mode of action at their MIC values. The compound upon treatment on both B. subtilis and P. aeruginosa released substantial amount of nucleic acid in the external medium and also effected the change of morphology towards pleomorphicity, thereby indicating its probable action on cell membrane. Furthermore, the triterpenoid 1 was found not to inhibit a probiotic lactic acid bacterium Lactococcus lactis subsp. lactis LABW4 under in vitro condition and to possess no toxicity in Swiss albino mice. © 2013.

  6. In-vitro DNA binding and cleavage studies with pBR322 of N,N-Bis(3{beta}-acetoxy-5{alpha}-cholest-6-yl-idene)hydrazine

    Energy Technology Data Exchange (ETDEWEB)

    Tabassum, Zishan [School of Industrial Technology, Universiti Sains Malaysia, 11800 USM, Penang (Malaysia); Muddassir, Mohd [Department of Chemistry, Aligarh Muslim University, Aligarh 202002, U.P. (India); Sulaiman, Othman [School of Industrial Technology, Universiti Sains Malaysia, 11800 USM, Penang (Malaysia); Arjmand, Farukh [Department of Chemistry, Aligarh Muslim University, Aligarh 202002, U.P. (India)

    2012-08-15

    The DNA binding studies of the triterpenoid derivative, cholesterol, N,N-Bis(3{beta}-acetoxy-5{alpha}-cholest-6-yl-idene)hydrazine (L) with CT DNA were carried out by employing different optical methods viz, UV-vis and fluorescence spectroscopy. The ligand binds to DNA through hydrophobic interaction with K{sub b} value found to be 4.7 Multiplication-Sign 10{sup 3} M{sup -1}. These observations have been validated also by fluorescence spectroscopy. (L) exhibits a remarkable DNA cleavage activity with pBR322 DNA in the presence of different activators and the DNA is probably cleaved by an other than oxidative mechanism, possibly by a discernable hydrolytic pathway. In the presence of major and minor groove binding agents, (L) prefers major groove binding of the DNA. - Highlights: Black-Right-Pointing-Pointer DNA binding studies of the triterpenoid derivative, cholesterol, N,N-Bis(3{beta}-acetoxy-5{alpha}-cholest-6-yl-idene)hydrazine. Black-Right-Pointing-Pointer The ligand binds to DNA through hydrophobic interaction with K{sub b} value found to be 4.7 Multiplication-Sign 10{sup 3} M{sup -1}. Black-Right-Pointing-Pointer DNA is probably cleaved by an other than oxidative mechanism, possibly by a discernable hydrolytic pathway. Black-Right-Pointing-Pointer In the presence of major and minor groove binding agents, the (L) prefers major groove binding of the DNA.

  7. In-vitro DNA binding and cleavage studies with pBR322 of N,N-Bis(3β-acetoxy-5α-cholest-6-yl-idene)hydrazine

    International Nuclear Information System (INIS)

    Tabassum, Zishan; Muddassir, Mohd; Sulaiman, Othman; Arjmand, Farukh

    2012-01-01

    The DNA binding studies of the triterpenoid derivative, cholesterol, N,N-Bis(3β-acetoxy-5α-cholest-6-yl-idene)hydrazine (L) with CT DNA were carried out by employing different optical methods viz, UV–vis and fluorescence spectroscopy. The ligand binds to DNA through hydrophobic interaction with K b value found to be 4.7×10 3 M −1 . These observations have been validated also by fluorescence spectroscopy. (L) exhibits a remarkable DNA cleavage activity with pBR322 DNA in the presence of different activators and the DNA is probably cleaved by an other than oxidative mechanism, possibly by a discernable hydrolytic pathway. In the presence of major and minor groove binding agents, (L) prefers major groove binding of the DNA. - Highlights: ► DNA binding studies of the triterpenoid derivative, cholesterol, N,N-Bis(3β-acetoxy-5α-cholest-6-yl-idene)hydrazine. ► The ligand binds to DNA through hydrophobic interaction with K b value found to be 4.7×10 3 M −1 . ► DNA is probably cleaved by an other than oxidative mechanism, possibly by a discernable hydrolytic pathway. ► In the presence of major and minor groove binding agents, the (L) prefers major groove binding of the DNA.

  8. A comparative study of conventional and supercritical fluid extraction methods for the recovery of secondary metabolites from Syzygium campanulatum Korth#

    Science.gov (United States)

    Memon, Abdul Hakeem; Hamil, Mohammad Shahrul Ridzuan; Laghari, Madeeha; Rithwan, Fahim; Zhari, Salman; Saeed, Mohammed Ali Ahmed; Ismail, Zhari; Majid, Amin Malik Shah Abdul

    2016-01-01

    Syzygium campanulatum Korth is a plant, which is a rich source of secondary metabolites (especially flavanones, chalcone, and triterpenoids). In our present study, three conventional solvent extraction (CSE) techniques and supercritical fluid extraction (SFE) techniques were performed to achieve a maximum recovery of two flavanones, chalcone, and two triterpenoids from S. campanulatum leaves. Furthermore, a Box-Behnken design was constructed for the SFE technique using pressure, temperature, and particle size as independent variables, and yields of crude extract, individual and total secondary metabolites as the dependent variables. In the CSE procedure, twenty extracts were produced using ten different solvents and three techniques (maceration, soxhletion, and reflux). An enriched extract of five secondary metabolites was collected using n-hexane:methanol (1:1) soxhletion. Using food-grade ethanol as a modifier, the SFE methods produced a higher recovery (25.5%‒84.9%) of selected secondary metabolites as compared to the CSE techniques (0.92%‒66.00%). PMID:27604860

  9. A comparative study of conventional and supercritical fluid extraction methods for the recovery of secondary metabolites from Syzygium campanulatum Korth.

    Science.gov (United States)

    Memon, Abdul Hakeem; Hamil, Mohammad Shahrul Ridzuan; Laghari, Madeeha; Rithwan, Fahim; Zhari, Salman; Saeed, Mohammed Ali Ahmed; Ismail, Zhari; Majid, Amin Malik Shah Abdul

    2016-09-01

    Syzygium campanulatum Korth is a plant, which is a rich source of secondary metabolites (especially flavanones, chalcone, and triterpenoids). In our present study, three conventional solvent extraction (CSE) techniques and supercritical fluid extraction (SFE) techniques were performed to achieve a maximum recovery of two flavanones, chalcone, and two triterpenoids from S. campanulatum leaves. Furthermore, a Box-Behnken design was constructed for the SFE technique using pressure, temperature, and particle size as independent variables, and yields of crude extract, individual and total secondary metabolites as the dependent variables. In the CSE procedure, twenty extracts were produced using ten different solvents and three techniques (maceration, soxhletion, and reflux). An enriched extract of five secondary metabolites was collected using n-hexane:methanol (1:1) soxhletion. Using food-grade ethanol as a modifier, the SFE methods produced a higher recovery (25.5%‒84.9%) of selected secondary metabolites as compared to the CSE techniques (0.92%‒66.00%).

  10. Anti-diabetic effects of Ganoderma lucidum.

    Science.gov (United States)

    Ma, Haou-Tzong; Hsieh, Jung-Feng; Chen, Shui-Tein

    2015-06-01

    Ganoderma lucidum is a white rot fungus widely used as a tonic for the promotion of longevity and health. Extracts of G. lucidum have been recognized as an alternative adjuvant treatment for diabetes. Among the many biologically active constituents of G. lucidum, polysaccharides, proteoglycans, proteins and triterpenoids have been shown to have hypoglycemic effects. G. lucidum polysaccharides have been reported to have hypoglycemic activity by increasing plasma insulin levels and decreasing plasma sugar levels in mice. Protein tyrosine phosphatase 1B is a promising therapeutic target in diabetes, and G. lucidum proteoglycan can inhibit this enzyme in vitro. Moreover, G. lucidum triterpenoids were shown to have inhibitory activity on aldose reductase and α-glucosidase that can suppress postprandial hyperglycemia. In addition, a protein Ling Zhi-8 extracted from G. lucidum significantly decreased lymphocyte infiltration and increased the antibody detection of insulin in diabetic mice. This review summarizes most of the research about the hypoglycemic action effects of polysaccharides, proteoglycans, proteins and tritrerpenoids from G. lucidum as a guide for future research. Copyright © 2015 Elsevier Ltd. All rights reserved.

  11. The anti-invasive effect of lucidenic acids isolated from a new Ganoderma lucidum strain.

    Science.gov (United States)

    Weng, Chia-Jui; Chau, Chi-Fai; Chen, Kuang-Dee; Chen, Deng-Hai; Yen, Gow-Chin

    2007-12-01

    Ganoderma lucidum is a well-known mushroom with various pharmacological effects that has been used for health and longevity purposes. The objective of this study was to investigate the anti-invasive effect of lucidenic acids isolated from a new G. lucidum strain (YK-02) against human hepatoma carcinoma (HepG(2)) cells. Triterpenoid components in the ethanol extract of G. lucidum (YK-02) were separated by means of a semi-preparative RP HPLC. Four major peaks were separated and crystallized from triterpenoids fraction, and were identified as lucidenic acids A, B, C, and N according to their spectroscopic values of (1)H NMR and MS. Treatment of the lucidenic acids (50 microM) in the presence of 200 nM phorbol 12-myristate 13-acetate (PMA) after 24 h of incubation all resulted in significant inhibitory effects on PMA-induced MMP-9 activity and invasion of HepG(2 )cells. The results indicate that the lucidenic acids isolated from G. lucidum (YK-02) are anti-invasive bioactive components on hepatoma cells.

  12. Genotoxicity test of Maytenus rigida and Aristolochia birostris in the radicular meristem of the onion, Allium cepa

    Directory of Open Access Journals (Sweden)

    Sandra S. Mendes

    2011-09-01

    Full Text Available Medicinal plants are an important source of treatment for many ailments, although little is known of the potential genotoxic effects of most species. In the present study, two species from diverse and medicinally important genera - Maytenus rigida Mart., Celastraceae, and Aristolochia birostris Ducht, Aristolochiaceae - were analyzed to identify potentially significant secondary metabolites and the possible effects of their aqueous and alcoholic extracts on cell division in the onion root stem (genotoxicity test. The phytochemical testing revealed the presence of a number of potentially important secondary compounds in both species, including phenols, flavonoids, triterpenoids, steroids, and saponins. In the genotoxicity tests, no chromosomal abnormalities of any kind were observed in either species. In the case of M. rigida, a significant increase in mitotic activity was observed at the highest concentration. No significant tendency was recorded in A. birostris, although a considerable increase in the prophase was observed at all concentrations of the alcoholic extract. The triterpenoid content of both species may be especially important from a medicinal viewpoint, although recent findings on the carcinogenic potential of Aristolochia extracts demands caution in the interpretation of the results, and the need for further research.

  13. Genotoxicity test of Maytenus rigida and Aristolochia birostris in the radicular meristem of the onion, Allium cepa

    Directory of Open Access Journals (Sweden)

    Sandra S. Mendes

    2012-02-01

    Full Text Available Medicinal plants are an important source of treatment for many ailments, although little is known of the potential genotoxic effects of most species. In the present study, two species from diverse and medicinally important genera - Maytenus rigida Mart., Celastraceae, and Aristolochia birostris Ducht, Aristolochiaceae - were analyzed to identify potentially significant secondary metabolites and the possible effects of their aqueous and alcoholic extracts on cell division in the onion root stem (genotoxicity test. The phytochemical testing revealed the presence of a number of potentially important secondary compounds in both species, including phenols, flavonoids, triterpenoids, steroids, and saponins. In the genotoxicity tests, no chromosomal abnormalities of any kind were observed in either species. In the case of M. rigida, a significant increase in mitotic activity was observed at the highest concentration. No significant tendency was recorded in A. birostris, although a considerable increase in the prophase was observed at all concentrations of the alcoholic extract. The triterpenoid content of both species may be especially important from a medicinal viewpoint, although recent findings on the carcinogenic potential of Aristolochia extracts demands caution in the interpretation of the results, and the need for further research.

  14. Fruit cuticle lipid composition and fruit post-harvest water loss in an advanced backcross generation of pepper (Capsicum sp.)

    KAUST Repository

    Parsons, Eugene P.

    2012-03-05

    To understand the role of fruit cuticle lipid composition in fruit water loss, an advanced backcross population, the BC2F2, was created between the Capsicum annuum (PI1154) and the Capsicum chinense (USDA162), which have high and low post-harvest water loss rates, respectively. Besides dramatic differences in fruit water loss, preliminary studies also revealed that these parents exhibited significant differences in both the amount and composition of their fruit cuticle. Cuticle analysis of the BC2F2 fruit revealed that although water loss rate was not strongly associated with the total surface wax amount, there were significant correlations between water loss rate and cuticle composition. We found a positive correlation between water loss rate and the amount of total triterpenoid plus sterol compounds, and negative correlations between water loss and the alkane to triterpenoid plus sterol ratio. We also report negative correlations between water loss rate and the proportion of both alkanes and aliphatics to total surface wax amount. For the first time, we report significant correlations between water loss and cutin monomer composition. We found positive associations of water loss rate with the total cutin, total C16 monomers and 16-dihydroxy hexadecanoic acid. Our results support the hypothesis that simple straight-chain aliphatic cuticle constituents form more impermeable cuticular barriers than more complex isoprenoid-based compounds. These results shed new light on the biochemical basis for cuticle involvement in fruit water loss. © 2012 Physiologia Plantarum.

  15. Eclalbasaponin II induces autophagic and apoptotic cell death in human ovarian cancer cells

    Directory of Open Access Journals (Sweden)

    Yoon Jin Cho

    2016-09-01

    Full Text Available Triterpenoids echinocystic acid and its glycosides, isolated from several Eclipta prostrata, have been reported to possess various biological activities such as anti-inflammatory, anti-bacterial, and anti-diabetic activity. However, the cytotoxicity of the triterpenoids in human cancer cells and their molecular mechanism of action are poorly understood. In the present study, we found that eclalbasaponin II with one glucose moiety has potent cytotoxicity in three ovarian cancer cells and two endometrial cancer cells compared to an aglycone echinocystic acid and eclalbasaponin I with two glucose moiety. Eclalbasaponin II treatment dose-dependently increased sub G1 population. Annexin V staining revealed that eclalbasaponin II induced apoptosis in SKOV3 and A2780 ovarian cancer cells. In addition, eclalbasaponin II-induced cell death was associated with characteristics of autophagy; an increase in acidic vesicular organelle content and elevation of the levels of LC3-II. Interestingly, autophagy inhibitor BaF1 suppressed the eclalbasaponin II-induced apoptosis. Moreover, eclalbasaponin II activated JNK and p38 signaling and inhibited the mTOR signaling. We further demonstrated that pre-treatment with a JNK and p38 inhibitor and mTOR activator attenuated the eclalbasaponin II-induced autophagy. This suggests that eclalbasaponin II induces apoptotic and autophagic cell death through the regulation of JNK, p38, and mTOR signaling in human ovarian cancer cells.

  16. Development of the cuticular wax during growth of Kalanchoe daigremontiana (Hamet et Perr. de la Bathie) leaves.

    Science.gov (United States)

    Van Maarseveen, Clare; Han, Hong; Jetter, Reinhard

    2009-01-01

    The goal of the present study was to monitor cuticular wax accumulation during leaf development of Kalanchoe daigremontiana. Leaves expanded linearly until they were 40-60 d old. Wax coverages of leaves on the third node increased steadily during initial leaf development, from 6.5 microg x cm(-2) on day 22 to 15.3 microg x cm(-2) on day 53, and then levelled off. Triterpenoids dominated the wax mixture throughout leaf development, but decreased from 74 to 40-45% in mature leaves, while very long-chain fatty acid (VLCFA) derivatives increased from 19 to 39-44%. The major VLCFA derivatives were alkanes, accompanied by fatty acids, primary alcohols, aldehydes and alkyl esters. In all compound classes, either C(34) or C(33) homologs predominated during leaf development. Eight different triterpenoids were identified, with glutinol constituting 70% of the fraction, and friedelin (20%) and germanicol (10%) as further major components of the young leaf wax. The glutinol percentage decreased, while the relative amounts of epifriedelanol and glutanol increased during development. Various leaf pairs upwards from the third node showed similar growth patterns and developmental time courses of cuticular wax amounts and composition. Based on these surface chemical analyses, the relative activities of biosynthetic pathways leading to various wax components can be assessed.

  17. Detection of Ganoderic Acid A in Ganoderma lingzhi by an Indirect Competitive Enzyme-Linked Immunosorbent Assay.

    Science.gov (United States)

    Sakamoto, Seiichi; Kohno, Toshitaka; Shimizu, Kuniyoshi; Tanaka, Hiroyuki; Morimoto, Satoshi

    2016-05-01

    Ganoderma is a genus of medicinal mushroom traditionally used for treating various diseases. Ganoderic acid A is one of the major bioactive Ganoderma triterpenoids isolated from Ganoderma species. Herein, we produced a highly specific monoclonal antibody against ganoderic acid A (MAb 12 A) and developed an indirect competitive ELISA for the highly sensitive detection of ganoderic acid A in Ganoderma lingzhi, with a limit of detection of 6.10 ng/mL. Several validation analyses support the accuracy and reliability of the developed indirect competitive ELISA for use in the quality control of Ganoderma based on ganoderic acid A content. Furthermore, quantitative analysis of ganoderic acid A in G. lingzhi revealed that the pileus exhibits the highest ganoderic acid A content compared with the stipe and spore of the fruiting body; the best extraction efficiency was found when 50 % ethanol was used, which suggests the use of a strong liquor to completely harness the potential of Ganoderma triterpenoids in daily life. Georg Thieme Verlag KG Stuttgart · New York.

  18. [Advance in chemical constituents of genus Clematis].

    Science.gov (United States)

    Sun, Feng; Yang, Depo

    2009-10-01

    Progresses in the studies on chemical constituents of Clematis L. (belonging to the family Ranunculaceae) were systematiically reviewed in this article. The plants in this genus have a wide spectrum of constituents as follows: triterpenes, flavonoids, lignans, coumarins, alkaloids, volatile oils, steroids, organic acids, macrocyclic compounds and phenols, etc., among which triterpenoid saponins, flavonoids and lignans are the main components. The triterpenoid saponins are mainly oleanolic type and hederagenin type, most of which are bidesmosidic saponins, substituted with oligosaccharide chains at both C-3 and C-28, and some are substituted with acetyl, caffeoyl, isoferuloyl, p-methoxy cinnamyl and 3,4-dimethoxy cinnamyl groups in the oligosaccharide chains. The flavonoids from Clematis species are mainly flavones, flavonols, flavanones, isoflavones, xanthones and their glucosides (sugar moieties are connected to the aglycone through either the oxygen or the carbon atoms), the aglycones of which are mainly apigenin, kaempferol, luteolin and quercetin. The lignans from Clematis are mainly eupomatene lignans, cyclolignans, monoepoxylignans, bisepoxylignans and lignanolides. Clematis spp. are rich in resources, however, studies on their chemical constituents have only been carried out on twenty or so spp. As a result, it is necessary to expand our study on other spp. from this genus for better utilization of medicinal resources.

  19. Dual activities of the anti-cancer drug candidate PBI-05204 provide neuroprotection in brain slice models for neurodegenerative diseases and stroke.

    Science.gov (United States)

    Van Kanegan, Michael J; Dunn, Denise E; Kaltenbach, Linda S; Shah, Bijal; He, Dong Ning; McCoy, Daniel D; Yang, Peiying; Peng, Jiangnan; Shen, Li; Du, Lin; Cichewicz, Robert H; Newman, Robert A; Lo, Donald C

    2016-05-12

    We previously reported neuroprotective activity of the botanical anti-cancer drug candidate PBI-05204, a supercritical CO2 extract of Nerium oleander, in brain slice and in vivo models of ischemic stroke. We showed that one component of this neuroprotective activity is mediated through its principal cardiac glycoside constituent, oleandrin, via induction of the potent neurotrophic factor brain-derived neurotrophic factor (BDNF). However, we also noted that the concentration-relation for PBI-05204 in the brain slice oxygen-glucose deprivation (OGD) model is considerably broader than that for oleandrin as a single agent. We thus surmised that PBI-05204 contains an additional neuroprotective component(s), distinct from oleandrin. We report here that neuroprotective activity is also provided by the triterpenoid constituents of PBI-05204, notably oleanolic acid. We demonstrate that a sub-fraction of PBI-05204 (Fraction 0-4) containing oleanolic and other triterpenoids, but without cardiac glycosides, induces the expression of cellular antioxidant gene transcription programs regulated through antioxidant transcriptional response elements (AREs). Finally, we show that Fraction 0-4 provides broad neuroprotection in organotypic brain slice models for neurodegeneration driven by amyloid precursor protein (APP) and tau implicated in Alzheimer's disease and frontotemporal dementias, respectively, in addition to ischemic injury modeled by OGD.

  20. Inhibitory Effects of Cytosolic Ca2+ Concentration by Ginsenoside Ro Are Dependent on Phosphorylation of IP3RI and Dephosphorylation of ERK in Human Platelets

    Directory of Open Access Journals (Sweden)

    Hyuk-Woo Kwon

    2015-01-01

    Full Text Available Intracellular Ca2+ ([Ca2+]i is platelet aggregation-inducing molecule and is involved in activation of aggregation associated molecules. This study was carried out to understand the Ca2+-antagonistic effect of ginsenoside Ro (G-Ro, an oleanane-type saponin in Panax ginseng. G-Ro, without affecting leakage of lactate dehydrogenase, dose-dependently inhibited thrombin-induced platelet aggregation, and the half maximal inhibitory concentration was approximately 155 μM. G-Ro inhibited strongly thrombin-elevated [Ca2+]i, which was strongly increased by A-kinase inhibitor Rp-8-Br-cAMPS compared to G-kinase inhibitor Rp-8-Br-cGMPS. G-Ro increased the level of cAMP and subsequently elevated the phosphorylation of inositol 1, 4, 5-triphosphate receptor I (IP3RI (Ser1756 to inhibit [Ca2+]i mobilization in thrombin-induced platelet aggregation. Phosphorylation of IP3RI (Ser1756 by G-Ro was decreased by PKA inhibitor Rp-8-Br-cAMPS. In addition, G-Ro inhibited thrombin-induced phosphorylation of ERK 2 (42 kDa, indicating inhibition of Ca2+ influx across plasma membrane. We demonstrate that G-Ro upregulates cAMP-dependent IP3RI (Ser1756 phosphorylation and downregulates phosphorylation of ERK 2 (42 kDa to decrease thrombin-elevated [Ca2+]i, which contributes to inhibition of ATP and serotonin release, and p-selectin expression. These results indicate that G-Ro in Panax ginseng is a beneficial novel Ca2+-antagonistic compound and may prevent platelet aggregation-mediated thrombotic disease.

  1. Geochemical and geological control on filling history of Eocene reservoirs, Maracaibo Basin, Venezuela

    Energy Technology Data Exchange (ETDEWEB)

    Alberdi, M.; Maguregui, J.; Toro, C.; Marquina, M. [Intevep S.A., Caracas (Venezuela)

    1996-08-01

    Crude oils of Eocene fluvio-deltaic reservoirs in {open_quotes}Bloque V{close_quotes} and {open_quotes}Centro Lago{close_quotes} fields in the center of the Maracaibo Lake show many differences in composition, which are due to stratigraphically and structurally controlled reservoir geometry and a low rate of in-reservoir mixing of at least two successive petroleum charges. Oils produced from the top of structural highs contain 18(H) oleanane, higher Pr/Ph and C{sub 23-3}/C{sub 24-4} ratios, a lower proportion of DBT/P compounds, and clearly different fingerprint patterns in the C{sub 6}-C{sub 15} range, than those observed in oils produced from the lower parts of the structures. These compositional differences suggest that two source rocks, or two distinctive organic facies within the same Cretaceous La Luna Formation, generated and filled vertically poorly connected Eocene reservoirs. On the other hand, saturate-biomarkers ratios, triaromatics (C{sub 21}/C{sub 21}+C{sub 28}), n-paraffins (n-C{sub 20}/n-C{sub 29}) and n-heptane index suggest that oils in upper reservoirs are slightly less mature than oils in lower reservoirs and, consequently filled the structure first. Additional evidence from formation water analysis and tectonic basin evolution allow us to interpret at least two petroleum pulses from Cretaceous source rocks during Upper Miocene to present day kitchens located in the Andes foredeep at the southeast of the study area.

  2. Organic petrological and organic geochemical characterisation of the Tertiary coal-bearing sequence of Batu Arang, Selangor, Malaysia

    Science.gov (United States)

    Wan Hasiah, Abdullah; Abolins, Peter

    1998-08-01

    The Tertiary coal-bearing sequence at Batu Arang in Selangor, Peninsular Malaysia consists of a sandstone-coal-oil shale facies assemblage. A detailed organic petrological and organic geochemical study was carried out on several organic-rich sediments from this sequence. The oil shales are dominated by Botryococcus-derived telalginite and Pediastrum-derived lamalginite. The coals, hypautochthonous in origin, are mainly duroclarite-type, although other minor microlithotypes also occur. Alginite is not observed in the coals, but other liptinitic constituents are very common, particularly thin-walled cutinite and sporinite. The oil shales and the coals are thermally immature. This immaturity has a considerable influence on the biomarker distributions, particularly so on the triterpanes which are dominated by C 31αβ 22R and C 30ββ compounds. Interestingly, for Tertiary aged sediments of continental origin, the diagnostic biomarker compounds such as 18 α(H)-oleanane and bicadinanes, normally linked to the higher land plant group of angiosperms, are not observed in the samples analysed. Tricyclic terpanes occur only in very low relative abundance or are virtually absent. A clear distinction, however, in the biomarker distributions of the shales and the coals/carbargilite can be made based upon the distribution of C 27-C 29 regular steranes: the shales, with a source input being predominantly planktonic algae, are dominated by 5 α(H),14 α(H),17 α(H) 20R cholestane, while the coals/carbargilites, with a source input consisting mainly of higher plant material, are dominated by 5 α(H),14 α(H),17 α(H) 20R ethyl cholestane. The depositional environment of the Batu Arang coal-bearing sequence is interpreted as varying from an alluvial flood plain peat-swamp to fluvio-lacustrine depositional setting.

  3. Geochemical characteristics of Tertiary saline lacustrine oils in the Western Qaidam Basin, northwest China

    International Nuclear Information System (INIS)

    Zhu Yangming; Weng Huanxin; Su Aiguo; Liang Digang; Peng Dehua

    2005-01-01

    Based on the systematic analyses of light hydrocarbon, saturate, aromatic fractions and C isotopes of over 40 oil samples along with related Tertiary source rocks collected from the western Qaidam basin, the geochemical characteristics of the Tertiary saline lacustrine oils in this region was investigated. The oils are characterized by bimodal n-alkane distributions with odd-to-even (C 11 -C 17 ) and even-to-odd (C 18 -C 28 ) predominance, low Pr/Ph (mostly lower than 0.6), high concentration of gammacerane, C 35 hopane and methylated MTTCs, reflecting the high salinity and anoxic setting typical of a saline lacustrine depositional environment. Mango's K 1 values in the saline oils are highly variable (0.99-1.63), and could be associated with the facies-dependent parameters such as Pr/Ph and gammacerane indexes. Compared with other Tertiary oils, the studied Tertiary saline oils are marked by enhanced C 28 sterane abundance (30% or more of C 27 -C 29 homologues), possibly derived from halophilic algae. It is noted that the geochemical parameters of the oils in various oilfields exhibit regular spatial changes, which are consistent with the depositional phase variations of the source rocks. The oils have uncommon heavy C isotopic ratios (-24%o to -26%o) and a flat shape of the individual n-alkane isotope profile, and show isotopic characteristics similar to marine organic matter. The appearance of oleanane and high 24/(24 + 27)-norcholestane ratios (0.57-0.87) in the saline oils and source rocks confirm a Tertiary organic source

  4. Potato wound-healing tissues: A rich source of natural antioxidant molecules with potential for food preservation.

    Science.gov (United States)

    Dastmalchi, Keyvan; Wang, Isabel; Stark, Ruth E

    2016-11-01

    The need for safe, effective preservatives is a prominent issue in the food and drug industries, reflecting demand for natural alternatives to synthetic chemicals viewed as harmful to consumers and the environment. Thus, this study determined the identities and scavenging capacities of antioxidant metabolites produced as a response to potato tuber wounding, using activity-guided fractionation of polar extracts from a Yukon Gold cultivar that had previously exhibited exceptionally high radical-scavenging activity. Activity-guided fractionation using the ABTS(+) radical scavenging assay and LC-MS with TOF-MS for compositional analysis of the most potent antioxidant fractions yielded identification of nine constituents: coumaroylputrescine; feruloylquinic acid; isoferuloylputrescine; ferulic acid; 22,25-dimethoxy-3-[[2,3,4-tri-O-methyl-6-O-(2,3,4,6-tetra-O-methyl-β-d-glucopyranosyl)-β-d-glucopyranosyl]oxy]-(3β)-lanost-9(11)-en-24-one; 4-(2Z)-2-decen-1-yl-5-[1-(4-hydroxyphenyl)decyl]-1,2-benzenediol; 8-[(2E)-3,7-dimethyl-2,6-octadien-1-yl]-5-hydroxy-2,8-dimethyl-6-(3-methyl-2-buten-1-yl)-2H-1-benzopyran-4,7(3H,8H)-dione; 3-[(2-O-β-d-glucopyranosyl-β-d-glucopyranosyl)oxy]-20-[(6-O-β-d-xylopyranosyl-β-d-glucopyranosyl)oxy]-dammar-24-en-19-al; (3β)-28-oxo-28-(phenylmethoxy)oleanan-3-yl 2-O-β-d-galactopyranosyl-3-O-(phenylmethyl)-, butyl ester β-d-glucopyranosiduronic acid. A positive correlation was observed between the scavenging activities and the polarities of the active fractions. The antioxidant capacities of the fractions were also characterised by monitoring the activity throughout a 45-minute assay period. Copyright © 2016 Elsevier Ltd. All rights reserved.

  5. Application of a multimolecular marker approach to fingerprint petroleum pollution in the marine environment

    International Nuclear Information System (INIS)

    Barakat, Assem O.; Mostafa, Alaa R.; Rullkoetter, Juergen; Hegazi, Abdel Rahman

    1999-01-01

    In an attempt to investigate the suitability of a multibiological marker approach for defining the origin of petroleum pollution in marine systems, the aliphatic hydrocarbon composition of tar ball samples collected from the beaches of a small island impacted by heavy tar loads were determined by gas chromatography and gas chromatography/mass spectrometry. The tar ball samples, as collected, were at low stages of biodegradation and had diverse physical appearance. The majority of the samples (as many as 7 of the 10) appeared to be heavy fuel oils - possibly Bunker C. The GC traces for the other three tar balls, however, indicated that they were crude oils probably from tanker ballast washings or other non-point sources like the oil entering from the adjacent North Mediterranean. The biomarkers for the sterane and hopane series in these samples, however, had remained unaffected by weathering, and their distributions revealed significant differences among the samples suggesting multiple sources of the tar balls. The tar ball samples could be genetically subdivided into four groups on the basis of their biomarker fingerprints. A marine carbonate or evaporite, hypersaline, anoxic depositional environment of the petroleum source rock for Type I residues could be inferred from the even-carbon-number predominance of n-alkanes, the high relative abundance of gammacerane and the predominance of C 35 relative to C 34 17α(H)-homohopanes. Higher plant contribution and a deltaic environment of source rock deposition could be concluded for Type II residues from the high concentrations of oleanane and diasteranes. On the other hand, Type III residues possessed geochemical characteristics consistent with a normal marine carbonate or evaporite source depositional environment under normal saline, reducing conditions. Finally, type IV residues had biomarker signatures intermediate between Types II and III. (Author)

  6. Five new triterpene saponins, polygalasaponins XXVIII-XXXII from the root of Polygala japonica Houtt.

    Science.gov (United States)

    Zhang, D; Miyase, T; Kuroyanagi, M; Umehara, K; Ueno, A

    1996-04-01

    Five new oleanane-type saponins, polygalasaponins XXVIII-XXXII, along with one known saponin, polygalasaponin XXIV, and one known acylated sucrose, tenuifoliside C, were isolated from the root of Polygala japonica. The structures of these new compounds were elucidated as 3-O-beta-D-glucopyranosyl pesenegenin 28-O-beta-D-xylopyranosyl (1-->4)-alpha-L-rhamnopyranosyl (1-->2)-beta-D-fucopyranosyl ester, 3-O-beta-D-glucopyranosyl presenegenin 28-O-beta-D-galactopyranosyl (1-->5)-beta-D-apiofuranosyl (1-->4)-beta-D-xylopyranosyl (1-->4)-alpha-L-rhamno-pyranosyl (1-->2)-beta-D-fucopyranosyl ester, 3-O-beta-D-glucopyranosyl presenegenin 28-O-beta-D-galactopyranosyl (1-->4)-beta-D-xylopyranosyl (1-->4)-alpha-L-rhamnopyranosyl (1-->2)-[4-O-p-methoxycinnamoyl]-[beta-D-glucopyranosyl (1-->3)]-beta-D-fucopyranosyl ester, 3-O-beta-D-glucopyranosyl presenegenin 28-O-alpha-L-arabinopyranosyl (1-->3)-beta-D-xylopyranosyl (1-->4)-[beta-D-apiofuranosyl (1-->3)]-alpha-L-rhamnopyranosyl (1-->2)-[4-O-3,4,5-trimethoxycinnamoyl]-beta-D-fucopyranosyl ester, 3-O-beta-D-glucopyranosyl persenegenin 28-O-alpha-L-arabinopyranosyl (1-->3)-beta-D-xylopyranosyl (1-->4)-[beta-D-apiofuranosyl (1-->3)-alpha-L-rhamnopyranosyl (1-->2)-[4-O-p-methoxycinnamoyl]-[alpha-L-rhamnopyranosyl (1-->3)-beta-D-fucopyranosyl ester, respectively, on the basis of spectroscopic and chemical evidence.

  7. Effectiveness of cuticular transpiration barriers in a desert plant at controlling water loss at high temperatures.

    Science.gov (United States)

    Schuster, Ann-Christin; Burghardt, Markus; Alfarhan, Ahmed; Bueno, Amauri; Hedrich, Rainer; Leide, Jana; Thomas, Jacob; Riederer, Markus

    2016-01-01

    Maintaining the integrity of the cuticular transpiration barrier even at elevated temperatures is of vital importance especially for hot-desert plants. Currently, the temperature dependence of the leaf cuticular water permeability and its relationship with the chemistry of the cuticles are not known for a single desert plant. This study investigates whether (i) the cuticular permeability of a desert plant is lower than that of species from non-desert habitats, (ii) the temperature-dependent increase of permeability is less pronounced than in those species and (iii) whether the susceptibility of the cuticular permeability barrier to high temperatures is related to the amounts or properties of the cutin or the cuticular waxes. We test these questions with Rhazya stricta using the minimum leaf water vapour conductance (gmin) as a proxy for cuticular water permeability. gmin of R. stricta (5.41 × 10(-5) m s(-1) at 25 °C) is in the upper range of all existing data for woody species from various non-desert habitats. At the same time, in R. stricta, the effect of temperature (15-50 °C) on gmin (2.4-fold) is lower than in all other species (up to 12-fold). Rhazya stricta is also special since the temperature dependence of gmin does not become steeper above a certain transition temperature. For identifying the chemical and physical foundation of this phenomenon, the amounts and the compositions of cuticular waxes and cutin were determined. The leaf cuticular wax (251.4 μg cm(-2)) is mainly composed of pentacyclic triterpenoids (85.2% of total wax) while long-chain aliphatics contribute only 3.4%. In comparison with many other species, the triterpenoid-to-cutin ratio of R. stricta (0.63) is high. We propose that the triterpenoids deposited within the cutin matrix restrict the thermal expansion of the polymer and, thus, prevent thermal damage to the highly ordered aliphatic wax barrier even at high temperatures. Published by Oxford University Press on behalf of the

  8. Effects of Salicylic Acid on the Growth and Physiological Characteristics in Cyclocarya Paliurus Seedlings

    International Nuclear Information System (INIS)

    Xie, Y.; Guo, N.; Zhang, Y.; Liu, N.; Wang, T.; Yang, W.; Fang, S.

    2016-01-01

    Field studies were conducted to examine the effects of salicylic acid (SA) on the growth and physiological characteristics of Cyclocarya paliurus seedlings by spraying the foliage with 0.0 (control), 0.2, 1.0, and 2.0 mM salicylic acid (SA). Proper concentrations of SA improved the relative growth yield of seedling stems and the soluble protein and sugar content of the leaves. It also increased the content of secondary metabolites including triterpenoids, flavonoids, quercetin and kaempferol, mineral elements K, Ca, Mg, Mn, Fe and Cu. Moreover, it stimulated the activities of superoxide dismutase (SOD), peroxidase (POX) and phenylalanine ammonia lyase (PAL) in the leaves. The effects of SA on these indices were dose dependent. The relative growth of seedling stem diameter and quercetin content increased gradually with an increase in concentration of SA from 0.0-2.0 mM. A concentration of 0.2 mM was optimal to promote content of soluble protein, sugars, Ca, Mg, Mn, Fe, and Cu, and SOD activity and significantly increased by 38.6 percentage, 22.1 percentage, 17.7 percentage, 8.2 percentage, 20.3 percentage, 23.2 percentage, 15.6 percentage, and 52.4 percentage, respectively, as compared with the control (CK). However, the maximal increase in activities of PAL, POX, and content of triterpenoids, kaempferol, and flavonoids was attained at 1.0 mM treatment, which significantly increased by 76.5 percentage, 78.4 percentage, 76.4 percentage, 96.3 percentage, and 107.4 percentage, respectively, compared with CK. Correlation analysis revealed positive relationships between activities of PAL, POX and content of triterpenoids, quercetin, kaempferol, and flavonoids within a certain concentration range of SA. These results suggested that an appropriate concentration (0.2-1.0 mM) of SA was not only effective in the improvement of physiological function of C. paliurus, but also increased seedling resistance; additionally, it helped to stimulate the synthesis of medicinal

  9. Lindersin B from Lindernia crustacea induces neuritogenesis by activation of tyrosine kinase A/phosphatidylinositol 3 kinase/extracellular signal-regulated kinase signaling pathway.

    Science.gov (United States)

    Cheng, Lihong; Ye, Ying; Xiang, Lan; Osada, Hiroyuki; Qi, Jianhua

    2017-01-15

    Neurotrophic factors such as nerve growth factor (NGF) play important roles in nervous system. NGF is a potential therapeutic drug for treatment of neurodegenerative diseases. However, because of physicochemical property, NGF cannot pass through the blood-brain barrier (BBB). Hence, small molecules which exhibit NGF-mimic activity and can pass through the BBB are considered to be promising drug candidates for treatment of such diseases. The present study was designed to isolate NGF-mimic substance from extract of natural products, determine their structures and investigate mechanism of action of the active substance. Extract of Lindernia crustacean was partitioned between water and ethyl acetate to obtain water layer and ethyl acetate layer samples, respectively, and then evaluated their neuritogenic activity in PC12 cells. The active sample was separated by open columns, followed by HPLC purification to obtain active compound. Then, specific inhibitors were used to investigate signaling pathway of neurite outgrowth induced by the active compound. Finally, western blot analysis was performed to confirm the pathway proposed by inhibitor experiments. The ethyl acetate layer sample of extract of Lindernia crustacea exhibited significant neuritogenic activity. Two new compounds, named as linderside A and lindersin B, were isolated; their structures were elucidated by spectroscopic and chemical derivatization methods. Linderside A is a cucurbitane glycoside, whereas lindersin B is a cucurbitane triterpenoid. Each compound has an unusual isopentene unit, namely, a double bond bound to an unmodified isopropyl group at the end of cucurbitane triterpenoid side chain. Among them, lindersin B induced significant neurite outgrowth in PC12 cells, while linderside A was inactive against PC12 cells. Western blotting analysis results showed that lindersin B-induced neuritogenic activity depended on the activation of the mitogen-activated protein kinase (MAPK)/extracellular signal

  10. Ontology-based systematic representation and analysis of traditional Chinese drugs against rheumatism.

    Science.gov (United States)

    Liu, Qingping; Wang, Jiahao; Zhu, Yan; He, Yongqun

    2017-12-21

    Rheumatism represents any disease condition marked with inflammation and pain in the joints, muscles, or connective tissues. Many traditional Chinese drugs have been used for a long time to treat rheumatism. However, a comprehensive information source for these drugs is still missing, and their anti-rheumatism mechanisms remain unclear. An ontology for anti-rheumatism traditional Chinese drugs would strongly support the representation, analysis, and understanding of these drugs. In this study, we first systematically collected reported information about 26 traditional Chinese decoction pieces drugs, including their chemical ingredients and adverse events (AEs). By mostly reusing terms from existing ontologies (e.g., TCMDPO for traditional Chinese medicines, NCBITaxon for taxonomy, ChEBI for chemical elements, and OAE for adverse events) and making semantic axioms linking different entities, we developed the Ontology of Chinese Medicine for Rheumatism (OCMR) that includes over 3000 class terms. Our OCMR analysis found that these 26 traditional Chinese decoction pieces are made from anatomic entities (e.g., root and stem) from 3 Bilateria animals and 23 Mesangiospermae plants. Anti-inflammatory and antineoplastic roles are important for anti-rheumatism drugs. Using the total of 555 unique ChEBI chemical entities identified from these drugs, our ChEBI-based classification analysis identified 18 anti-inflammatory, 33 antineoplastic chemicals, and 9 chemicals (including 3 diterpenoids and 3 triterpenoids) having both anti-inflammatory and antineoplastic roles. Furthermore, our study detected 22 diterpenoids and 23 triterpenoids, including 16 pentacyclic triterpenoids that are likely bioactive against rheumatism. Six drugs were found to be associated with 184 unique AEs, including three AEs (i.e., dizziness, nausea and vomiting, and anorexia) each associated with 5 drugs. Several chemical entities are classified as neurotoxins (e.g., diethyl phthalate) and allergens (e

  11. Organic Tracers from Asphalt in Propolis Produced by Urban Honey Bees, Apis mellifera Linn.

    Science.gov (United States)

    Alqarni, Abdulaziz S; Rushdi, Ahmed I; Owayss, Ayman A; Raweh, Hael S; El-Mubarak, Aarif H; Simoneit, Bernd R T

    2015-01-01

    Propolis is a gummy material produced by honey bees to protect their hives and currently has drawn the attention of researchers due to its broad clinical use. It has been reported, based only on observations, that honey bees also collect other non-vegetation substances such as paint or asphalt/tar to make propolis. Therefore, propolis samples were collected from bee hives in Riyadh and Al-Bahah, a natural area, Saudi Arabia to determine their compositional characteristics and possible sources of the neutral organic compounds. The samples were extracted with hexane and analyzed by gas chromatography-mass spectrometry. The results showed that the major compounds were n-alkanes, n-alkenes, methyl n-alkanoates, long chain wax esters, triterpenoids and hopanes. The n-alkanes (ranging from C17 to C40) were significant with relative concentrations varying from 23.8 to 56.8% (mean = 44.9+9.4%) of the total extracts. Their odd carbon preference index (CPI) ranged from 3.6 to 7.7, with a maximum concentration at heptacosane indicating inputs from higher plant vegetation wax. The relative concentrations of the n-alkenes varied from 23.8 to 41.19% (mean = 35.6+5.1%), with CPI = 12.4-31.4, range from C25 to C35 and maximum at tritriacontane. Methyl n-alkanoates, ranged from C12 to C26 as acids, with concentrations from 3.11 to 33.2% (mean = 9.6+9.5%). Long chain wax esters and triterpenoids were minor. The main triterpenoids were α- and β-amyrins, amyrones and amyryl acetates. The presence of hopanes in some total extracts (up to 12.5%) indicated that the bees also collected petroleum derivatives from vicinal asphalt and used that as an additional ingredient to make propolis. Therefore, caution should be taken when considering the chemical compositions of propolis as potential sources of natural products for biological and pharmacological applications. Moreover, beekeepers should be aware of the proper source of propolis in the flight range of their bee colonies.

  12. Geochemical evidence for different peat sources in the Siak estuary and along the east coast of Sumatra, Indonesia

    Directory of Open Access Journals (Sweden)

    R. Wöstmann

    2012-02-01

    Full Text Available The distribution pattern of selected biomarkers extracted from samples of outcropping peat from the Siak river, its estuary, the coast around Dumai and the island of Bengkalis have been investigated by gas chromatography (GC and combined gas chromatography/mass spectrometry (GC/MS, and compared with samples of eroded peat washed ashore (re-deposited on the coastline of Sumatra. Geochemical analyses of n-alkanes, n-alkanols, n-alkanoic acids, steroids and triterpenoids show that outcropping and re-deposited peats have different chemical compositions. The outcropping peats around Dumai, Bengkalis and in the Siak River estuary contain high concentrations of the pentacyclic triterpenoid taraxerol, a typical constituent of the mangrove species Rhizophora. A comparison with the lipid composition of leaves from the fringing mangrove species (Avicennia alba, Sonneratia alba and Rhizophora apiculata showed that only R. apiculata contains significant amounts of taraxerol. Taraxerol was completely absent from the leaves of A. alba and S. alba. This suggests that the peats outcropping around Dumai, Bengkalis and in the Siak estuary must be formed by a dominant input of mangroves of the Rhizophora family. The n-alkane distribution patterns of the outcropping peats near Dumai and the Siak estuary are similar to those of the surrounding mangrove vegetation with a maximum at C31 and a strong predominance of odd over even carbon numbers in all samples. Biomarker analysis of eroded peats washed ashore along the coastline around Dumai and the Siak estuary shows a different lipid composition with high amounts of the triterpenoids friedelin, α-amyrin and β-amyrin. These compounds are typical biomarkers for tropical forest vegetation as found along the Siak River and for peats eroding at upstream river banks. The n-alkanol distribution patterns of re-deposited peats also indicate a different origin for their organic matter. Peats re-deposited in the Siak estuary

  13. Phytochemical Composition and Antioxidant Capacity of Seven Saskatoon Berry (Amelanchier alnifolia Nutt. Genotypes Grown in Poland

    Directory of Open Access Journals (Sweden)

    Sabina Lachowicz

    2017-05-01

    Full Text Available The basic chemical composition, bioactive compounds, and antioxidant capacity of fruits of three new Polish breeding clones (No. 5/6, type S, and type N and four Canadian cultivars (cvs. (“Martin”, “Smoky”, “Pembina”, and “Honeywood” grown in Poland in 2016 were investigated. Fruits were analyzed for their contents of triterpenoids, carotenoids, chlorophylls, and polyphenolics with the ultra-performance liquid chromatography photodiode detector-quadrupole/time-of-flight mass spectrometry (UPLC-PDA-Q/TOF-MS method, sugar with the high-performance liquid chromatography–evaporative light scattering detector (HPLC-ELSD method, and antioxidant capacity with the ability to reduce free radical (ABTS and ferric reducing ability of plasma (FRAP method. Thirty-eight bioactive compounds, including twenty-eight polyphenolic compounds (four anthocyanins, nine phenolic acids, nine flavonols, and seven flavan-3-ols, four carotenoids, two chlorophylls, and three triterpenoids were identified in the fruits. The fruits of the tested Saskatoon berry genotypes were found to be rich in phenolic compounds (3773.94–6390.36 mg/100 g·dm, triterpenoids (66.55–91.31 mg/kg·dm, and carotenoids (478.62–561.57 mg/kg·dm, with high ABTS and FRAP capacity (10.38–34.49 and 9.66–25.34 mmol·Trolox/100 g·dm, respectively. Additionally, the berries of these genotypes seemed to be a good source of sugar (9.02–19.69 g/100 g, pectins (0.67%–1.33%, and ash (0.59%–0.67%. Some genotypes of Saskatoon berry, especially the clones type S, type N, and cvs. “Honeywood” and “Smoky”, may be selected for their potential applications in commercial cultivation to produce fruits with valuable health-promoting nutritional effects on human health. Additionally, three new genotypes that may offer new functional materials can be recommended for fruit growers.

  14. Qualitative phytochemical screening and evaluation of anti-inflammatory, analgesic and antipyretic activities of Microcos paniculata barks and fruits.

    Science.gov (United States)

    Aziz, Md Abdullah

    2015-05-01

    The main objectives of this study were to qualitatively evaluate the profile of phytochemical constituents present in methanolic extract of Microcos paniculata bark (BME) and fruit (FME), as well as to evaluate their anti-inflammatory, analgesic and antipyretic activities. Phytochemical constituents of BME and FME were determined by different qualitative tests such as Molisch's test, Fehling's test, alkaloid test, frothing test, FeCl3 test, alkali test, Salkowski's test and Baljet test. The anti-inflammatory, analgesic and antipyretic activities of the extracts were evaluated through proteinase-inhibitory assay, xylene-induced ear edema test, cotton pellet-induced granuloma formation in mice, formalin test, acetic acid-induced writhing test, tail immersion test and Brewer's yeast-induced pyrexia in mice. M. paniculata extracts revealed the presence of carbohydrates, alkaloids, saponins, tannins, flavonoids and triterpenoids. All of the extracts showed significant (Panalgesic activities at 60 min in the tail immersion test. Again, the significant (Panalgesic and antipyretic activities.

  15. Phytochemistry, Pharmacology and Traditional Uses of Plants from the Genus Trachelospermum L.

    Directory of Open Access Journals (Sweden)

    Zefeng Zhao

    2017-08-01

    Full Text Available This paper is intended to review advances in the botanical, phytochemical, traditional uses and pharmacological studies of the genus Trachelospermum. Until now, 138 chemical constituents have been isolated and characterized from these plants, particularly from T. asiaticum and T. jasminoides. Among these compounds, lignans, triterpenoids, and flavonoids are the major bioactive constituents. Studies have shown that plants from the genus Trachelospermum exhibit an extensive range of pharmacological properties both in vivo and in vitro, including anti-inflammatory, analgesic, antitumor, antiviral and antibacterial activities. In Traditional Chinese Medicine (TCM culture, drugs that include T. jasminoides stems have been used to cure rheumatism, gonarthritis, backache and pharyngitis, although there are few reports concerning the clinical use and toxicity of these plants. Further attention should be paid to gathering information about their toxicology data, quality-control measures, and the clinical value of the active compounds from genus Trachelospermum.

  16. An In-Silico Investigation of Phytochemicals as Antiviral Agents Against Dengue Fever.

    Science.gov (United States)

    Powers, Chelsea N; Setzer, William N

    2016-01-01

    A virtual screening analysis of our library of phytochemical structures with dengue virus protein targets has been carried out using a molecular docking approach. A total of 2194 plant-derived secondary metabolites have been docked. This molecule set comprised of 290 alkaloids (68 indole alkaloids, 153 isoquinoline alkaloids, 5 quinoline alkaloids, 13 piperidine alkaloids, 14 steroidal alkaloids, and 37 miscellaneous alkaloids), 678 terpenoids (47 monoterpenoids, 169 sesquiterpenoids, 265 diterpenoids, 81 steroids, and 96 triterpenoids), 20 aurones, 81 chalcones, 349 flavonoids, 120 isoflavonoids, 74 lignans, 58 stilbenoids, 169 miscellaneous polyphenolic compounds, 100 coumarins, 28 xanthones, 67 quinones, and 160 miscellaneous phytochemicals. Dengue virus protein targets examined included dengue virus protease (NS2B-NS3pro), helicase (NS3 helicase), methyltransferase (MTase), RNA-dependent RNA polymerase (RdRp), and the dengue virus envelope protein. Polyphenolic compounds, flavonoids, chalcones, and other phenolics were the most numerous of the strongly docking ligands for dengue virus protein targets.

  17. Facile Synthesis of Oleanolic Acid Monoglycosides and Diglycosides

    Directory of Open Access Journals (Sweden)

    Mao-Sheng Cheng

    2008-07-01

    Full Text Available Oleanolic acid and its glycosides are important natural products, possessing various attractive biological activities such as antitumor, antivirus and anti-inflammatory properties. In the present work, fifteen oleanolic acid saponins bearing various saccharide moieties, including 3-monoglycoside, 28-monoglycoside and 3,28-diglycoside, were easily synthesized in high yields. Benzyl was chosen as the protective group for the COOH(28 group, instead of commonly used methyl and allyl, to avoid difficulties in the final deprotection. Alkali-promoted condensation of the carboxylic acid with bromoglycosides was found to be more efficient in the synthesis of 28-glycosides. Two approaches were investigated and proved practicable in the preparation of 3,28- diglycosides. This method is suitable for preparing oleanolic acid glycosides with structural diversity for extensive biological evaluation and structure-activity relationship study, and it also apply new idea for the corresponding synthetic methods to the glycoside derivatives of other triterpenoid.

  18. Rhodamine B conjugates of triterpenoic acids are cytotoxic mitocans even at nanomolar concentrations.

    Science.gov (United States)

    Sommerwerk, Sven; Heller, Lucie; Kerzig, Christoph; Kramell, Annemarie E; Csuk, René

    2017-02-15

    Triterpenoic acids 1-6 exhibited very low or no cytotoxicity at all, but their corresponding 2,3-di-O-acetyl-piperazinyl amides 13-18 showed low EC 50 values for several human tumor cell lines. Their cytotoxicity, however, was also high for the non-malignant mouse fibroblasts NIH 3T3. A significant improvement was achieved by preparing the rhodamine B derivatives 19-24. While rhodamine B is not cytotoxic (up to a concentration of 30μM - cut-off of the assay), the triterpenoid piperazine-spacered rhodamine B derivatives were cytotoxic in nano-molar concentration. Compound 24 (a diacetylated maslinic acid derivative) was most toxic for several human tumor cell lines but less toxic for mouse fibroblasts NIH 3T3. Staining and double-staining experiments revealed 24 to act as a mitocan. Copyright © 2016 Elsevier Masson SAS. All rights reserved.

  19. Pregnanes and other constituents of the roots of Macrosiphonia petraea (A. St.-Hil.) Kuntze (Apocynaceae); Pregnanos e outros constituintes das raizes de Macrosiphonia petraea (A. St.-Hil.) Kuntze (Apocynaceae)

    Energy Technology Data Exchange (ETDEWEB)

    Assis Junior, Luiz Roberto de; Garcez, Fernanda Rodrigues; Garcez, Walmir Silva, E-mail: walmir.garcez@ufms.br [Universidade Federal de Mato Grosso do Sul (UFMS), Campo Grande, MS (Brazil). Centro de Ciencias Exatas e Tecnologia; Guterres, Zaira da Rosa [Universidade Estadual de Mato Grosso do Sul (UFMS), Mundo Novo, MS (Brazil)

    2013-09-01

    Macrosiphonia petraea (A. St.-Hil.) Kuntze is a plant popularly known as 'velame'. Its root infusion is used in the folk medicine of Mato Grosso do Sul, Brazil, for the treatment of inflammatory diseases. Phytochemical investigation of the roots of this species led to the identification of 17 compounds belonging to four different classes: two pregnanes, 12{beta}-hydroxypregna-4,6,16-triene-3,20-dione, neridienone A, and 12{beta}-hydroxypregna-4,6-diene-3,20-dione, cybisterol, one hydroxylated fatty acid, 5-hydroxy-octadeca-6(E)-8(Z)-dienoic acid, two lignoids, pinoresinol and 8{alpha}-hydroxypinoresinol, ten pentacyclic triterpenoids, and two steroids. (author)

  20. Mimusops elengi bark extract mediated green synthesis of gold nanoparticles and study of its catalytic activity

    Science.gov (United States)

    Majumdar, Rakhi; Bag, Braja Gopal; Ghosh, Pooja

    2016-04-01

    The bark extract of Mimusops elengi is rich in different types of plant secondary metabolites such as flavonoids, tannins, triterpenoids and saponins. The present study shows the usefulness of the bark extract of Mimusops elengi for the green synthesis of gold nanoparticles in water at room temperature under very mild conditions. The synthesis of the gold nanoparticles was complete within a few minutes without any extra stabilizing or capping agents and the polyphenols present in the bark extract acted as both reducing as well as stabilizing agents. The synthesized colloidal gold nanoparticles were characterized by HRTEM, surface plasmon resonance spectroscopy and X-ray diffraction studies. The synthesized gold nanoparticles have been used as an efficient catalyst for the reduction of 3-nitrophenol and 4-nitrophenol to their corresponding aminophenols in water at room temperature.

  1. Anacardic acid derivatives from Brazilian propolis and their antibacterial activity

    Energy Technology Data Exchange (ETDEWEB)

    Silva, M.S.S.; Lima, S.G. de; Lopes, J.A.D.; Chaves, M.H.; Cito, A.M.G.L. [Universidade Federal do Piaui (UFPI), Teresina, PI (Brazil). Dept. de Quimica]. E-mail: gracito@ufpi.br; Oliveira, E.H. [Universidade Federal do Piaui (UFPI), Teresina, PI (Brazil). Dept. de Microbiologia e Parasitologia; Reis, F.A.M. [Universidade Estadual de Campinas (UNICAMP), Campinas, SP (Brazil). Inst. de Quimica

    2008-07-01

    Propolis is a sticky, gummy, resinous substance collected by honeybees (Apis mellifera L.) from various plant sources, which has excellent medicinal properties. This paper describes the isolation and identification of triterpenoids and anacardic acid derivatives from Brazilian propolis and their antibacterial activity. Their structures were elucidated by {sup 1}H and {sup 13}C NMR, including uni- and bidimensional techniques; in addition, comparisons were made with data from academic literature. These compounds were identified as: cardanols (1a + 1b), cardols (2a + 2b), mono ene anacardic acid (3), alpha-amirine (4), beta-amirine (5), cycloartenol (6), 24-methylene-cycloartenol (7) and lupeol (8). The determination of the position of the double bond after a reaction with Dimethyl disulfide (DMDS) is described for the phenol derivatives. The ethanolic extract was tested in vitro for antimicrobial activity by using the disc diffusion method and it showed significant results against Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa and Shigella spp. (author)

  2. Pregnanes and other constituents of the roots of Macrosiphonia petraea (A. St.-Hil.) Kuntze (Apocynaceae)

    International Nuclear Information System (INIS)

    Assis Junior, Luiz Roberto de; Garcez, Fernanda Rodrigues; Garcez, Walmir Silva

    2013-01-01

    Macrosiphonia petraea (A. St.-Hil.) Kuntze is a plant popularly known as 'velame'. Its root infusion is used in the folk medicine of Mato Grosso do Sul, Brazil, for the treatment of inflammatory diseases. Phytochemical investigation of the roots of this species led to the identification of 17 compounds belonging to four different classes: two pregnanes, 12β-hydroxypregna-4,6,16-triene-3,20-dione, neridienone A, and 12β-hydroxypregna-4,6-diene-3,20-dione, cybisterol, one hydroxylated fatty acid, 5-hydroxy-octadeca-6(E)-8(Z)-dienoic acid, two lignoids, pinoresinol and 8α-hydroxypinoresinol, ten pentacyclic triterpenoids, and two steroids. (author)

  3. Antibacterial and antioxidant activities of Licania tomentosa (Benth. fritsch (crhysobalanaceae

    Directory of Open Access Journals (Sweden)

    Silva J.B.N.F.

    2012-01-01

    Full Text Available This work describes the chemical composition, and evaluates the antimicrobial and antioxidant activities of a hydroalcoholic extract from the leaves of the Licania tomentosa. Gram positive and negative bacterial strains were used in this work. Examination of the phytochemical composition of L. tomentosa revealed the presence of secondary metabolites such as tannins, flavonoids, saponins, alkaloids, steroids and triterpenoids. An antibacterial assay pointed out that the extract had a lower minimal inhibitory concentration (MIC - 32 μg/mL towards Staphylococcus aureus (ATCC12692. The extract also presented antibacterial activity against other assayed bacteria, with the MIC varying between 64 and 512 μg/ mL. Our findings reveal that the extract presented an antioxidative capacity lower than that of BHT at the same concentration, used as positive control. Our results suggest that the levels and combinations between the secondary metabolites of this plant should be investigated to explain the demonstrated antibacterial activity.

  4. An access to a library of novel triterpene derivatives with a promising pharmacological potential by Ugi and Passerini multicomponent reactions.

    Science.gov (United States)

    Wiemann, Jana; Heller, Lucie; Csuk, René

    2018-04-25

    The promising combination of natural product leads and their derivatization by isocyanide-based multicomponent reactions (IMCRs) has gained interest in accessing diversity-oriented libraries with auspicious pharmacological potential. Therefore, a set of 34 Ugi and 3 Passerini products was successfully synthesized starting from naturally occurring triterpenoids, i.e. oleanolic acid (OA) and maslinic acid (MA), followed by a biological evaluation of the novel α-acylamino carboxamides and the α-acyloxy carboxamides in colorimetric SRB assays to determine their cytotoxic potential. Especially, the MA-Ugi products 6a, 6b and 7b showed a remarkable cytotoxicity for A2780 ovarian carcinoma cells in a low μM range. Compounds 6a and 7b induced programmed cell death in part through the apoptosis pathway. Copyright © 2018 Elsevier Masson SAS. All rights reserved.

  5. A new saponin from Acanthopanax koreanum with anti-inflammatory activity.

    Science.gov (United States)

    Dat, Le Duc; Thao, Nguyen Phuong; Luyen, Bui Thi Thuy; Tai, Bui Huu; Woo, Mi Hee; Manzoor, Zahid; Ali, Irshad; Koh, Young Sang; Kim, Young Ho

    2017-03-01

    Twelve saponins were isolated from the leaves of Acanthopanax koreanum, including one new lupane-type triterpene glycoside, named acankoreoside R (1), together with 11 known triterpenoid saponins (2-12). Their structures were elucidated by 1D and 2D nuclear magnetic resonance (NMR), mass spectroscopic data (MS). All of the fractions and isolated saponins were evaluated for anti-inflammatory activities in lipopolysaccharide (LPS)-stimulated bone marrow-derived dendritic cells (BMDCs) by ELISA. Among them, compounds 1-5, 7, 10, and 12 showed strong inhibitions towards interleukin-12 (IL-12) production with IC 50 values ranging from 1.59 to 5.46 µM. Other compounds were weak or inactive toward IL-12 p40 production.

  6. Steroidal Saponins

    Science.gov (United States)

    Sahu, N. P.; Banerjee, S.; Mondal, N. B.; Mandal, D.

    The medicinal activities of plants are generally due to the secondary metabolites (1) which often occur as glycosides of steroids, terpenoids, phenols etc. Saponins are a group of naturally occurring plant glycosides, characterized by their strong foam-forming properties in aqueous solution. The cardiac glycosides also possess this, property but are classified separately because of their specific biological activity. Unlike the cardiac glycosides, saponins generally do not affect the heart. These are classified as steroid or triterpenoid saponins depending on the nature of the aglycone. Steroidal glycosides are naturally occurring sugar conjugates of C27 steroidal compounds. The aglycone of a steroid saponin is usually a spirostanol or a furostanol. The glycone parts of these compounds are mostly oligosaccharides, arranged either in a linear or branched fashion, attached to hydroxyl groups through an acetal linkage (2, 3). Another class of saponins, the basic steroid saponins, contain nitrogen analogues of steroid sapogenins as aglycones.

  7. Direct detection of saponins in crude extracts of soapnuts by FTIR.

    Science.gov (United States)

    Almutairi, Meshari Saad; Ali, Muhammad

    2015-01-01

    Direct detection of saponins in soapnuts (Sapindus mukorossi) using Fourier transform infrared (FTIR) spectroscopy is investigated in this project. Potassium bromide powder was mixed with extracted powder of soapnuts and compressed to a thin pellet for examination process. The outcome of the FTIR spectra of saponin demonstrated characteristic triterpenoid saponin absorptions of OH, C = O, C-H, and C = C, while the glycoside linkages to the sapogenins were indicated by the absorptions of C-O. The significance of this study is that saponin absorption peaks are directly detectable in crude aqueous and 95% ethanol extracts of soapnuts powder using FTIR spectroscopy, thereby eliminating the need of further expensive and exhaustive purification steps. The extracts of soapnuts were screened for saponins along with controls by phytochemical tests, and advanced spectroscopic techniques such as ultra fast liquid chromatography and ultra performance liquid chromatography quadrupole-time of flight-mass spectrometry were also implemented to validate the saponins.

  8. Hydroxylation of a hederagenin derived saponin by a Xylareaceous fungus found in fruits of Sapindus saponaria

    Energy Technology Data Exchange (ETDEWEB)

    Murgu, Michael; Santos, Luiz F. Arruda; Souza, Gezimar D. de; Daolio, Cristina; Ferreira, Antonio Gilberto; Rodrigues-Filho, Edson [Universidade Federal de Sao Carlos (UFSCAR), SP (Brazil). Dept. de Quimica; Schneider, Bernd [Max Planck Institute for Chemical Ecology, Beutenberg Campus, Jena (Germany)

    2008-07-01

    During our screening of tropical plants for endophyte microorganisms, a Xylareaceous fungus was found living on the internal part of Sapindus saponaria fruits. The fruits of S. saponaria accumulate great amounts of triterpenoidal and sesquiterpenoidal saponins. The saponin 3-O-({beta}-D-xylopyranosyl)-(1{yields}3)-{alpha}-L -rhamnopyranosyl-(1{yields}2)-{alpha}-L-arabinopyranosyl-hederagenin was isolated using chromatographic methods, after alkaline hydrolysis of the crude extract obtained from S. saponaria fruits and added to the culture medium used to grows the fungus. A new saponin was isolated from this experiment by preparative scale HPLC and characterized as a 22{alpha}-hydroxy derivative. The structure of this hydroxylated saponin was elucidated based on interpretation of MS/MS data and NMR spectra. (author)

  9. Stereoisomers of Saponins in Panax notoginseng (Sanqi): A Review

    Science.gov (United States)

    Peng, Ming; Yi, Ya X.; Zhang, Tong; Ding, Yue; Le, Jian

    2018-01-01

    Panax notoginseng (Sanqi), a traditional Chinese medical drug which has been applied to medical use for over four centuries, contains high content of dammarane-type tetracyclic triterpenoid saponins. A number of stereoisomeric dammarane-type saponins exist in this precious herb, and some are particularly regarded as “biomarkers” in processed notoginseng. Contemporary researches have indicated that some saponin stereoisomers may show stereospecific pharmacological activities, such as anti-tumor, antioxidative, anti-photoaging, anti-inflammatory, antidiabetic, and neuro-protective activities, as well as stereoselective effects on ion channel current regulation, cardiovascular system, and immune system. The current review provides a comprehensive overview of chemical compositions of raw and processed P. notoginseng with a particular emphasis on saponin stereoisomers. Besides, the pharmacological and pharmacokinetic researches, as well as determination and biotechnological preparation methods of stereoisomeric saponins in notoginseng are discussed extensively. PMID:29593531

  10. Hydroxylation of a hederagenin derived saponin by a Xylareaceous fungus found in fruits of Sapindus saponaria

    International Nuclear Information System (INIS)

    Murgu, Michael; Santos, Luiz F. Arruda; Souza, Gezimar D. de; Daolio, Cristina; Ferreira, Antonio Gilberto; Rodrigues-Filho, Edson

    2008-01-01

    During our screening of tropical plants for endophyte microorganisms, a Xylareaceous fungus was found living on the internal part of Sapindus saponaria fruits. The fruits of S. saponaria accumulate great amounts of triterpenoidal and sesquiterpenoidal saponins. The saponin 3-O-(β-D-xylopyranosyl)-(1→3)-α-L -rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl-hederagenin was isolated using chromatographic methods, after alkaline hydrolysis of the crude extract obtained from S. saponaria fruits and added to the culture medium used to grows the fungus. A new saponin was isolated from this experiment by preparative scale HPLC and characterized as a 22α-hydroxy derivative. The structure of this hydroxylated saponin was elucidated based on interpretation of MS/MS data and NMR spectra. (author)

  11. Screening Some Plants for their Antiproliferative Compounds

    Directory of Open Access Journals (Sweden)

    Ufuk Kolak

    2012-03-01

    Full Text Available This paper covers the screening of the secondary plant products to find a cure against cancer which were piled up during the years. In early stages of these studies highly active antitumor glycoproteins were obtained from native Arizona (USA plants. Later smaller molecules were isolated showing antitumor activity in different test systems. Among these compounds sesquiterpene lactones with an exo-methylene group in the lactone ring, unsaturated diterpenoids and some triterpenoids exhibited activity in vivo and in vitro test systems. A few Colchicum alkaloids showed high activity against murine lymphocytic leukemia (P388. Activity also established in some flavonoidal compounds. Today all around the world research on Natural Products is still going on.

  12. A new iridoid and effect on the rat aortic vascular smooth muscle cell proliferation of isolated compounds from Buddleja officinalis.

    Science.gov (United States)

    Tai, Bui Huu; Nhiem, Nguyen Xuan; Quang, Tran Hong; Ngan, Nguyen Thi Thanh; Tung, Nguyen Huu; Kim, Yohan; Lee, Jung-Jin; Myung, Chang-Seon; Cuong, Nguyen Manh; Kim, Young Ho

    2011-06-01

    A new iridoid, named methylscutelloside (1) together with 19 known compounds belonging to the iridoids (2-4), monoterpenoids (5), flavonoids (6-8), triterpenoids (9-14), and phenylethanoids (15-20) were isolated from the flowers of Buddleja officinalis. Their chemical structures were elucidated on the basis of physicochemical properties, and by spectroscopic methods including 1D, 2D NMR, and MS. All isolated compounds were tested in vitro for their effects on the proliferation of rat aortic vascular smooth muscle cells (VSMCs). Among them, iridoids were the main active components and showed significant inhibitory effects on PDGF-BB-induced proliferation in rat aortic VSMCs. Copyright © 2011 Elsevier Ltd. All rights reserved.

  13. Medicinal uses, chemistry and pharmacology of Dillenia species (Dilleniaceae).

    Science.gov (United States)

    Sabandar, Carla W; Jalil, Juriyati; Ahmat, Norizan; Aladdin, Nor-Ashila

    2017-02-01

    The genus Dillenia is comprised of about 100 species of evergreen and deciduous trees or shrubs of disjunct distribution in the seasonal tropics of Madagascar through South and South East Asia, Malaysia, North Australia, and Fiji. Species from this genus have been widely used in medicinal folklore to treat cancers, wounds, jaundice, fever, cough, diabetes mellitus, and diarrhea as well as hair tonics. The plants of the genus also produce edible fruits and are cultivated as ornamental plants. Flavonoids, triterpenoids, and miscellaneous compounds have been identified in the genus. Their extracts and pure compounds have been reported for their antimicrobial, anti-inflammatory, cytotoxic, antidiabetes, antioxidant, antidiarrheal, and antiprotozoal activities. Mucilage from their fruits is used in drug formulations. Copyright © 2016 Elsevier Ltd. All rights reserved.

  14. A new ferulic acid ester and other constituents from Tamarix nilotica leaves.

    Science.gov (United States)

    Abouzid, Sameh Fekry; Ali, Sajjad Ahmed; Choudhary, Muhammad Iqbal

    2009-07-01

    Phytochemical investigation of the leaves of Tamarix nilotica (Tamaricaceae) has led to isolation of methyl ferulate 3-O-sulphate (1) for the first time from natural sources. In addition, coniferyl alcohol 4-O-sulphate (2), kaempferol 4'-methyl ether (3), tamarixetin (4) and quercetin 3-O-beta-D-glucupyranuronide (5) were isolated from the n-butanol soluble fraction of the extract. The pentacyclic triterpenoid, 3alpha-(3'',4''-dihydroxy-trans-cinnamoyloxy)-D-friedoolean-14-en-28-oic acid (6) was isolated from the n-hexane soluble fraction of the extract. The structures of these compounds were determined on the basis of spectroscopic analyses including 2 dimensional NMR. Compounds 3, 4 and 6 exhibited 1,1-diphenyl-2-picrylhydrazyl radical scavenging activity with IC(50) values of 35.2, 37.0 and 21.2 muM, respectively.

  15. Study of the utilization of propolis local propolis from Konawe, Southeast Sulawesi, as preservative natural preservative for beef

    Science.gov (United States)

    Natsir, Muh.; Kurniawati, Desy; kurniasih, Yeti

    2017-03-01

    The utilization of Propolis Trigona spp from Konawe, Southeast Sulawesi as a preservative naturally in beef has been done. The purpose of this research is to determine the ability of Propolis Trigona spp as a preservative. This study includes three stages, extraction of Propolis and analysis of phytochemicals, preserving a beef by soaking, as well as the microbes test. The rendemen extracts ethanol propolis be obtained in 19,15%. Based on analysis of phytochemicals it extracts Propolis of the class of compounds alkaloids, flavonoids, triterpenoid, tannins, saponins and essential oil. The best Curing of the beef can be obtained in the treatment Propolis 2.5 %. The result shows that Propolis Trigona spp from Konawe can be used as an alternative natural preservatives for the beef.

  16. Bases moleculares da ação anti-inflamatória dos ácidos oleanólico e ursólico sobre as isoformas da ciclo-oxigenase por docking e dinâmica molecular

    Directory of Open Access Journals (Sweden)

    Wendell Santos Magalhães

    2012-01-01

    Full Text Available The triterpenoids oleanolic (OA and ursolic (UA acids show non-selective antiinflamatory activity in vitro for cyclooxygenase (COX isoforms. 3D conformations of OA and UA, with three possible orientations (1, 1' and 2 in the active site of isoforms COX, obtained by docking, were submitted to molecular dynamics. The results show that orientation 2 of the OA in COX-2 is more favorable because orientation 1 moved away from the active site. The carboxylate group of OA interact by hydrogen bonds with Ser353 and with Phe357 and Leu359, mediated by water, while hydroxyl in C-3 interact by hydrogen bond, mediated by water, with Tyr385.

  17. Octadecanoides como reguladores de la defensa de las plantas

    Directory of Open Access Journals (Sweden)

    G. Camarena Gutiérrez

    2002-01-01

    Full Text Available En años recientes muchas moléculas lipoides muy potentes han sido identificadas, comprenden compuestos lipofílicos no derivados de lípidos como los brasinoesteroides triterpenoides, otros que parcialmente son de origen lipídico como los lipo-oligosacáridos, factores de nodulación de especies de Rhizobium que pueden tener parientes endógenos en las plantas, y un tercer grupo, los octadecanoides, cuyas estructuras son derivadas de ácidos grasos vegetales. Las señales mediadas por lípidos son un aspecto importante de la vida de las plantas y un área de investigación en rápido crecimiento.

  18. Chemical constituents of the stems of Spathelia excelsa (rutaceae) and activity against Aedes aegypti; Constituintes quimicos do caule de Spathelia excelsa (rutaceae) e atividade contra Aedes aegypti

    Energy Technology Data Exchange (ETDEWEB)

    Freitas, Aline Carvalho de; Lima, Maria da Paz [Instituto Nacional de Pesquisas da Amazonia (INPA), Manaus, AM (Brazil). Coordenacao de Pesquisas em Produtos Naturais], e-mail: mdapaz@inpa.gov.br; Ferreira, Antonio Gilberto [Universidade Federal de Sao Carlos (UFSCAR), SP (Brazil). Dept. de Quimica; Tadei, Wanderli Pedro; Pinto, Ana Cristina da Silva [Instituto Nacional de Pesquisas da Amazonia (INPA), Manaus, AM (Brazil). Lab. de Vetores de Malaria e Dengue

    2009-07-01

    Phytochemical investigation from the stems of Spathelia excelsa (Rutaceae) collected in Amazonas yielded deacetylspathelin (1), 7,8-dimethoxyflindersine (2), new glabretal-type triterpenoid 3{beta}-angeloyl-21,24-epoxy-7{alpha}, 21{alpha}, 23{alpha}, 25-tetrahydroxy-4{alpha}, 4{beta}, 8{beta}, 10{beta}-tetramethyl-25-dimethyl-14,18-cyclo-5{alpha}, 13{alpha}, 14{alpha}, 17{alpha}-cholestane (3), in addition to the known steroids s-sitosterol and stigmasterol. Their structures were established on the basis of spectral data. The compounds 1 and 3 were assayed on Aedes aegypti (larvicidal and adulticidal activities and compound 3 exhibited larvicidal properties with LC{sub 50} of 4,8 {mu}g/mL. (author)

  19. Chemical constituents of the stems of Spathelia excelsa (rutaceae) and activity against Aedes aegypti

    International Nuclear Information System (INIS)

    Freitas, Aline Carvalho de; Lima, Maria da Paz; Ferreira, Antonio Gilberto; Tadei, Wanderli Pedro; Pinto, Ana Cristina da Silva

    2009-01-01

    Phytochemical investigation from the stems of Spathelia excelsa (Rutaceae) collected in Amazonas yielded deacetylspathelin (1), 7,8-dimethoxyflindersine (2), new glabretal-type triterpenoid 3β-angeloyl-21,24-epoxy-7α, 21α, 23α, 25-tetrahydroxy-4α, 4β, 8β, 10β-tetramethyl-25-dimethyl-14,18-cyclo-5α, 13α, 14α, 17α-cholestane (3), in addition to the known steroids s-sitosterol and stigmasterol. Their structures were established on the basis of spectral data. The compounds 1 and 3 were assayed on Aedes aegypti (larvicidal and adulticidal activities and compound 3 exhibited larvicidal properties with LC 50 of 4,8 μg/mL. (author)

  20. Anacardic acid derivatives from Brazilian propolis and their antibacterial activity

    International Nuclear Information System (INIS)

    Silva, M.S.S.; Lima, S.G. de; Lopes, J.A.D.; Chaves, M.H.; Cito, A.M.G.L.; Oliveira, E.H.; Reis, F.A.M.

    2008-01-01

    Propolis is a sticky, gummy, resinous substance collected by honeybees (Apis mellifera L.) from various plant sources, which has excellent medicinal properties. This paper describes the isolation and identification of triterpenoids and anacardic acid derivatives from Brazilian propolis and their antibacterial activity. Their structures were elucidated by 1 H and 13 C NMR, including uni- and bidimensional techniques; in addition, comparisons were made with data from academic literature. These compounds were identified as: cardanols (1a + 1b), cardols (2a + 2b), mono ene anacardic acid (3), alpha-amirine (4), beta-amirine (5), cycloartenol (6), 24-methylene-cycloartenol (7) and lupeol (8). The determination of the position of the double bond after a reaction with Dimethyl disulfide (DMDS) is described for the phenol derivatives. The ethanolic extract was tested in vitro for antimicrobial activity by using the disc diffusion method and it showed significant results against Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa and Shigella spp. (author)

  1. C-4 Gem-Dimethylated Oleanes of Gymnema sylvestre and Their Pharmacological Activities

    Directory of Open Access Journals (Sweden)

    Giovanni Di Fabio

    2013-12-01

    Full Text Available Gymnema sylvestre R. Br., one of the most important medicinal plants of the Asclepiadaceae family, is a herb distributed throughout the World, predominantly in tropical countries. The plant, widely used for the treatment of diabetes and as a diuretic in Indian proprietary medicines, possesses beneficial digestive, anti-inflammatory, hypoglycemic and anti-helmentic effects. Furthermore, it is believed to be useful in the treatment of dyspepsia, constipation, jaundice, hemorrhoids, cardiopathy, asthma, bronchitis and leucoderma. A literature survey revealed that some other notable pharmacological activities of the plant such as anti-obesity, hypolipidemic, antimicrobial, free radical scavenging and anti-inflammatory properties have been proven too. This paper aims to summarize the chemical and pharmacological reports on a large group of C-4 gem-dimethylated pentacyclic triterpenoids from Gymnema sylvestre.

  2. Hybrid Compounds Strategy in the Synthesis of Oleanolic Acid Skeleton-NSAID Derivatives

    Directory of Open Access Journals (Sweden)

    Anna Pawełczyk

    2016-04-01

    Full Text Available The current study focuses on the synthesis of several hybrid individuals combining a natural oleanolic acid skeleton and synthetic nonsteroidal anti-inflammatory drug moieties (NSAIDs. It studied structural modifications of the oleanolic acid structure by use of the direct reactivity of hydroxyl or hydroxyimino groups at position C-3 of the triterpenoid skeleton with the carboxylic function of anti-inflammatory drugs leading to new perspective compounds with high potential pharmacological activities. Novel ester- and iminoester-type derivatives of oleanolic unit with the different NSAIDs, such as ibuprofen, aspirin, naproxen, and ketoprofen, were obtained and characterized. Moreover, preliminary research of compounds obtaining structure stability under acidic conditions was examined and the PASS method of prediction of activity spectra for substances was used to estimate the potential biological activity of these compounds.

  3. Impact of industrial hammer mill rotor speed on extraction efficiency and quality of extra virgin olive oil.

    Science.gov (United States)

    Polari, Juan J; Garcí-Aguirre, David; Olmo-García, Lucía; Carrasco-Pancorbo, Alegría; Wang, Selina C

    2018-03-01

    Crushing is a key step during olive oil extraction. Among commercial crushers, the hammer mill is the most widely used due to its robustness and high throughput. In the present work, the impact of hammer mill rotor speed on extraction yield and overall quality of super-high-density Arbosana olive oils were assessed in an industrial facility. Our results show that increasing the rotor speed from 2400rpm to 3600rpm led to a rise in oil yield of 1.2%, while conserving quality parameters. Sensory analysis showed more pungency with increased rotation speed, while others attributes were unaffected. Volatile compounds showed little variation with the differences in crusher speed; however, total phenols content, two relevant secoiridoids, and triterpenoids levels increased with rotor speed. Hammer mill rotor speed is a processing variable that can be tuned to increase the extraction efficiency and modulate the chemical composition of extra virgin olive oil. Copyright © 2017 Elsevier Ltd. All rights reserved.

  4. A cadinene biopolymer in fossil and extant dammar resins as a source for cadinanes and bicadinanes in crude oils from South East Asia

    Science.gov (United States)

    Van Aarssen, B. G. K.; Cox, H. C.; Hoogendoorn, P.; De Leeuw, J. W.

    1990-11-01

    The chemical composition of a fossil resin from a Miocene outcrop in Brunei, South East Asia, is compared with its extant counterpart dammar, obtained from trees of the family Dipterocarpaceae, to establish the nature of the precursor of bicadinanes. The alcohol soluble fractions of the resins consist of functionalised triterpenoids and a small amount of sesquiterpenoids. None of the compounds present in this fraction bears any structural relation to bicadinanes. The alcohol insoluble fractions of the resins consist of a polymer based on cadinene. A structure for this polymer is proposed. Heating the polymer in dammar resin resulted in the formation of monomeric, dimeric, and trimeric cadinenes. It is thought that the naturally occurring bicadinanes result from dimeric cadinenes upon cyclisation.

  5. Lateral transfer of tetrahymanol-synthesizing genes has allowed multiple diverse eukaryote lineages to independently adapt to environments without oxygen

    Directory of Open Access Journals (Sweden)

    Takishita Kiyotaka

    2012-02-01

    Full Text Available Abstract Sterols are key components of eukaryotic cellular membranes that are synthesized by multi-enzyme pathways that require molecular oxygen. Because prokaryotes fundamentally lack sterols, it is unclear how the vast diversity of bacterivorous eukaryotes that inhabit hypoxic environments obtain, or synthesize, sterols. Here we show that tetrahymanol, a triterpenoid that does not require molecular oxygen for its biosynthesis, likely functions as a surrogate of sterol in eukaryotes inhabiting oxygen-poor environments. Genes encoding the tetrahymanol synthesizing enzyme squalene-tetrahymanol cyclase were found from several phylogenetically diverged eukaryotes that live in oxygen-poor environments and appear to have been laterally transferred among such eukaryotes. Reviewers This article was reviewed by Eric Bapteste and Eugene Koonin.

  6. Anti-cancer activity of tectona hamiltoniana-an endemic plant of Myanmar

    International Nuclear Information System (INIS)

    Mya, K.M.; Shyaula, S.L.

    2012-01-01

    Summary: The ethanolic extracts of barks and leaves of Tectona hamiltoniana (Verbenaceae) were tested for anti-cancer activity against MCF-7 (Human breast cancer) and NCI-H460 (Lung cancer) cell lines employing sulpho rhodamine B (SRB) bioassay. These extracts demonstrated cytotoxicity with GI/sub 50/ values ranging between 24-33 macro g/mL against both cell lines. Upon further fractionation, dichloromethane fraction appeared to be most active against the MCF-7 cell line (GI/sub 50/ value of 3.4+-0.9 macro g/mL) leading to the isolation of lupane type triterpenoids, betulinic acid (1), betulin aldehyde ( 2 ) and betulin (3). Compound 2 and 3, both showed significant cytotoxic effect against both cancerous cell lines (GI/sub 50/ value range 6-11 macro M). (author)

  7. Ninety-day oral toxicity study of rice-derived γ-oryzanol in Sprague-Dawley rats.

    Science.gov (United States)

    Moon, Seol-Hee; Kim, Duyeol; Shimizu, Norihito; Okada, Tadashi; Hitoe, Shoketsu; Shimoda, Hiroshi

    2017-01-01

    A 90-day oral toxicity study of γ-oryzanol, a rice-derived triterpenoid ferulate, was performed by oral gavage administration to male and female Sprague-Dawley rats at doses of 0, 1000, and 2000 mg/kg body weight/day. All rats administered γ-oryzanol survived throughout the study period. Both male and female rats showed no toxicologically significant changes of the general signs, examination findings, body weight, food consumption, functional observational battery results, ophthalmological findings, urinalysis, hematology tests, clinical chemistry tests, organ weights, and necropsy findings. Moreover, there were no histopathological changes related to administration of γ-oryzanol in males and females from the 2000 mg/kg body weight/day group. In conclusion, the no observed adverse effect level (NOAEL) of γ-oryzanol exceeded 2000 mg/kg body weight/day for both male and female rats under the conditions of this study.

  8. Investigations on some metabolites of Tecoma stans Juss. callus tissue. Part III. Chromatographical search for iridoids, phenolic acids, terpenoids and sugars

    Directory of Open Access Journals (Sweden)

    Barbara Dohnal

    2015-01-01

    Full Text Available Tissus cultures of Tecoma stans Juss. cultivated on modified Murashige-Skoog medium (RT-k were phytochemically analysed by means of chromatographical methods (PC, TLC. The following products were found as metabolites: phenolic acids - chlorogenics, caffeic, ferulic, vanillic, o-coumaric and sinapic; steroids - β-sitosterol; triterpenes - ursolic and oleanolic acids, α-amyrine; sugars - glucose, fructose, sucrose, xylose. Meso-inositol was isolated in 0.8% yield. In intact plant leaves, some differences concerning the content and/or number of individual compounds were observed, namely: lack of sinapic acid and occurrence of p-coumaric acid, lower content of β-sitosterol, lack of oleanolic acid, occurrence of β-amyrine and of one unidentified triterpenoid, lack of xylose, occurrence of maltose, raffinose, and stachiose. The level of mesoinositol inn leaves was distincly lower than in the callus tissues. Neither in callus tissues nor in leaves iridoid glycosides were found.

  9. Synthesis and antiproliferative properties of new hydrophilic esters of triterpenic acids.

    Science.gov (United States)

    Eignerova, Barbara; Tichy, Michal; Krasulova, Jana; Kvasnica, Miroslav; Rarova, Lucie; Christova, Romana; Urban, Milan; Bednarczyk-Cwynar, Barbara; Hajduch, Marian; Sarek, Jan

    2017-11-10

    To improve the properties of cytotoxic triterpenoid acids 1-5, a large set of hydrophilic esters was synthesized. We choose betulinic acid (1), dihydrobetulinic acid (2), 21-oxoacid 3 along with highly active des-E lupane acids 4 and 5 as a model set of compounds for esterification of which the properties needed to be improved. As ester moieties were used - methoxyethanol and 2-(2-methoxyethoxy)ethanol and glycolic unit (type a-d), pyrrolidinoethanol, piperidinoethanol and morpholinoethanol (type f-h), and monosaccharide groups (type i-l). As a result, 56 triterpenic esters (49 new compounds) were obtained and their cytotoxicity on four cancer cell lines and normal human fibroblasts was tested. All new compounds were fully soluble at all tested concentrations, which used to be a problem of the parent compounds 1 and 2. 16 compounds had IC 50  acids 1-5. Copyright © 2017 Elsevier Masson SAS. All rights reserved.

  10. Codonopilate A, a Triterpenyl Ester as Main Autotoxin in Cultivated Soil of Codonopsis pilosula (Franch.) Nannf.

    Science.gov (United States)

    Xie, Min; Yan, Zhiqiang; Ren, Xia; Li, Xiuzhuang; Qin, Bo

    2017-03-15

    Codonopilate A (1), a triterpenyl ester, was isolated from monocultivated soil of annual Codonopsis pilosula and identified as the main autotoxin. The yield ratio of codonopilate A in dried soil was calculated as 2.04 μg/g. Other two triterpenoids, taraxeryl acetate (2) and 24-methylenecycloartanol (3), were isolated and identified as well showing weaker autotoxity. This was the first time that the potential allelochemicals and autotoxins in the cultivated soil of Codonopsis pilosula were reported. Accumulation of reactive oxygen species (ROS) induced by the autotoxins in the root tips of Codonopsis pilosula was considered as an important factor for the phytotoxic effect. This work systematically investigates the allelopathic and autotoxic effect of Codonopsis pilosula, and the preliminary autotoxic action mode of the three autotoxins. These findings are helpful to understand the molecular mechanism of autotoxicity and conducive to explore proper ways to degrade the autotoxins and eliminate the replanting problems of Codonopsis pilosula.

  11. Preparation of Conjugates of Cytotoxic Lupane Triterpenes with Biotin.

    Science.gov (United States)

    Soural, Miroslav; Hodon, Jiri; Dickinson, Niall J; Sidova, Veronika; Gurska, Sona; Dzubak, Petr; Hajduch, Marian; Sarek, Jan; Urban, Milan

    2015-12-16

    To better understand the mechanism of action of antitumor triterpenes, we are developing methods to identify their molecular targets. A promising method is based on combination of quantitative proteomics with SILAC and uses active compounds anchored to magnetic beads via biotin-streptavidin interaction. We developed a simple and fast solid-phase synthetic technique to connect terpenes to biotin through a linker. Betulinic acid was biotinylated from three different conjugation sites for use as a standard validation tool since many molecular targets of this triterpene are already known. Then, a set of four other cytotoxic triterpenoids was biotinylated. Biotinylated terpenes were similarly cytotoxic to their nonbiotinylated parents, which suggests that the target identification should not be influenced by linker or biotin. The developed solid-phase synthetic approach is the first attempt to use solid-phase synthesis to connect active triterpenes to biotin and is applicable as a general procedure for routine conjugation of triterpenes with other molecules of choice.

  12. Cucurbitacin: Ancient Compound Shedding New Light on Cancer Treatment

    Directory of Open Access Journals (Sweden)

    Dhong Hyun Lee

    2010-01-01

    Full Text Available Cucurbitacins and their derivatives are triterpenoids found in medicinal plants known for their diverse pharmacological and biological activities, including anticancer effects, throughout human history. Although initial attention to cucurbitacin as a potential anticancer drug withered for decades, recent discoveries showing that cucurbitacin is a strong STAT3 (Signal Transducers and Activators of Transcription-3 inhibitor have reclaimed the attention of the drug industry one more time. There is increasing evidence showing that some cucurbitacins not only inhibit the JAK-STAT pathway, but also affect other signaling pathways, such as the MAPK pathway, which are also known to be important for cancer cell proliferation and survival. Moreover, some reports have shown the synergistic effect of cucurbitacins with known chemotherapeutic agents, such as doxorubicin and gemcitabine. In this review, we will summarize the recent discoveries regarding molecular mechanisms of action of cucurbitacins in human cancer cells and discuss the possibilities of cucurbitacin as a future anticancer drug in clinical settings.

  13. Ragged Robin (Lychnis flos-cuculi - a plant with potential medicinal value

    Directory of Open Access Journals (Sweden)

    Michał P. Maliński

    Full Text Available Lychnis flos-cuculi L., Caryophyllaceae, contains a number of active compounds belonging to several chemical groups. Previous studies have led to the identification of phytoecdysteroids, triterpenoids saponins, volatile compounds, fatty acid derivatives, phenolic acids and flavonoids. Research on pharmacological activity showed that plant extracts inhibited the growth of bacteria and fungi. The antimitotic properties of preparations from the herb L. flos-cuculi were also reported. The phytochemical analyses demonstrated that this taxon contains pharmaceutically promising compounds, but more phytochemical and pharmacological studies of L. flos-cuculi are needed for further information regarding this plant. This review summarizes reports regarding chemical composition and biological activity of L. flos-cuculi as well as several cognate species, which pose opportunities related to in vitro propagation and cell and tissue cultures. In vitro-regenerated plantlets could be a good source of genetically uniform plant material for future research.

  14. Estudo fitoquímico da madeira de Guarea macrophylla (Meliaceae Phytochemical study of the wood from Guarea macrophylla (Meliaceae

    Directory of Open Access Journals (Sweden)

    João Henrique G. Lago

    2009-01-01

    Full Text Available In the present work, the crude ethanol extract from wood of G. macrophylla was submitted to liquid/liquid partition between hexane, CH2Cl2, EtOAc and n-BuOH. Each phase was individually chromatographed over silica gel, Sephadex LH-20 or Amberlite XAD-2 to give eight terpene derivatives, such as five sesquiterpenoids (caryophyllene oxide, guai-6-en-10β-ol, spathulenol, aromadendrane-4β,10α-diol and aloaromadendrane-4α,10β-diol as well as three triterpenoids (cicloart-24-ene-3β,23(R*-diol, cicloart-24-ene-3β,23(S*-diol, and cicloart-23E-ene-3β,25-diol. Additionally, were isolated three fatty acids (linolenic, linoleic and stearic, two steroids (sitosterol and stigmasterol and sacarose. The structures of all these compounds were characterized by spectrometric analysis, mainly mass spectrometry and NMR and comparison of these data described in the literature.

  15. Kaempferitrin from Uncaria guianensis (Rubiaceae) and its potential as a chemical marker for the species

    International Nuclear Information System (INIS)

    Valente, Ligia M.M.; Liechocki, Sally; Barboza, Rodolfo S.; Paixao, Djavan da; Bizarri, Carlos H.B.; Almeida, M. Beatriz S.; Benevides, Paulo J.C.; Siani, Antonio C.; Magalhaes, Alvicler

    2009-01-01

    Uncaria tomentosa (Willd.) DC. and U. guianensis (Aubl.) Gmel., known as cat's claw, are large woody vines native to the Amazonian and Central American rain forests. The species contain, in different proportions, indole and oxindole alkaloids, triterpenoid glycosides, sterols and proanthocyanidins. U. tomentosa can be chemically identified by its oxindole alkaloid profile and content, whereas U. guianensis has no satisfactorily established chemical markers. This work describes, for the first time, the isolation of kaempferol-3,7-O-(a)-dirhamnoside (kaempferitrin) in Uncaria species. Screening for this compound in leaves, stems or bark of both species through TLC and HPLC-DAD-MS showed the presence of kaempferitrin only in the leaves and stems of U. guianensis, at a ratio almost thirty six times greater in the leaves than in the stems. These results reveal the selectivity of U. guianensis to produce this bioactive flavonoid glycoside, and suggest this compound as a potential chemical marker for the species.(author)

  16. Improved anti-inflammatory activity of three new terpenoids derived, by systematic chemical modifications, from the abundant triterpenes of the flowery plant Calendula officinalis.

    Science.gov (United States)

    Neukirch, Hannes; D'Ambrosio, Michele; Sosa, Silvio; Altinier, Gianmario; Della Loggia, Roberto; Guerriero, Antonio

    2005-05-01

    Rings A, D and E of faradiol (1), and ring E of both arnidiol (10) and calenduladiol (4) have been subjected to various selective chemical manipulations to modify polarity, water affinity, H-bonding, sterics, and number of aromatic groups of these anti-inflammatory natural compounds. A total of 15 new and four known pentacyclic triterpenoids have been obtained in this way. Some 13 terpenoids were evaluated for their topical anti-inflammatory activities with respect to inhibition of croton oil induced ear oedema in mouse. Three derivatives of 1, the C(16) benzyl ether 15, the C(30) aldehyde 24, and the C(30) primary alcohol 25 showed significantly improved anti-inflammatory potencies, which is relevant for (future) structure-activity-relationship (SAR) studies.

  17. Improvement of Nutritional and Bioactive Compound Production by Lion's Mane Medicinal Mushroom, Hericium erinaceus (Agaricomycetes), by Spraying Growth Regulators.

    Science.gov (United States)

    Vi, Minhthuan; Yang, Xueqin; Zeng, Xianlu; Chen, Rui'an; Guo, Liqiong; Lin, Junfang; He, Qianyun; Zheng, Qianwang; Wei, Tao

    2018-01-01

    Hericium erinaceus is a popular culinary and medicinal mushroom in China because of its broad beneficial effects. In this study we evaluated the effects of stimulation with 7 growth regulators at 5 different concentrations on improving the production of nutritional and bioactive compounds by H. erinaceus. Results showed that among all the tested regulators, gibberellic acid (GA) increased protein content (165%), free amino acids (100%), polysaccharides (108%), and polyphenols (26%). Spraying nephthyl acetic acid increased polysaccharides and triterpenoids to 4.37 and 17.27 g/100 g, respectively. Spraying chitosan significantly increased polyphenols by 42%. The addition of triacontanol, indole acetic acid, and 2,4-dichlorophenoxyacetic acid improved the production of proteins, free amino acids, polysaccharides, and polyphenols, but not to the extent that GA did. These results indicate that adding certain growth regulators can effectively improve the production of nutritional and bioactive compounds in H. erinaceus.

  18. Evolutionary diversity among Atlantic coast mangroves

    Science.gov (United States)

    Dodd, Richard S.; Rafii, Zara A.; Fromard, François; Blasco, François

    1998-06-01

    Current knowledge of intraspecific variation of mangrove species is limited in terms of rangewide distributions and is mostly restricted to morphological analyses, which have indicated a high degree of homogeneity. However, our analyses of the aliphatic hydrocarbon and triterpenoid fraction of foliar waxes (by gas chromatography and mass spectroscopy) of mangrove species ( Rhizophora mangle, Avicennia germinans and Laguncularia racemosa) from Gabon in West Africa and French Guiana in South America show significant genetic differentiation between eastern and western Atlantic provenances. The greater diversity in lipid composition, and the tendency for longer carbon chain lengths in all taxa from Africa, may suggest that American mangroves exhibit derived characteristics. A consequence of this hypothesis would be that Atlantic mangroves are unlikely to have dispersed from the Tethys via the Pacific, as has been proposed by some authors. More widespread sampling within the Atlantic and east Pacific region is needed to support and confirm these results.

  19. An insight into medicinal and ethnopharmacological potential of Crotalaria burhia

    Directory of Open Access Journals (Sweden)

    Saboon

    2015-07-01

    Full Text Available Crotalaria burhia Buch.-Ham. (C. burhia (Fabaceae, is an undershurb found distributed in arid parts of the world. It extensively grows in Pakistan, India and Afghanistan. It is a highly medicinal plant. The leaves, branches and roots can be used as a cooling medicine. Plant juice is useful for treatments of gout, eczema, hydrophobia, pain and swellings, wounds and cuts, infection, kidney pain, abdominal problems, rheumatism and joint pain in traditional medicine system. The medicinal activity is the result of the presence of various important phytochemicals like alkaloids, flavonoids, phenols, polyphenols, tannins, steroids, triterpenoids, anthraquinones, crotalarine, monocrotaline, croburhine, crosemperine, quercetins and β-sitosterol. C. burhia is also known to possess antimicrobial, anti-inflammatory and antinociceptive activities, which supports its traditional uses. In this article, a comprehensive account of phytochemical constituents and pharmacological activities is presented along with traditional uses of C. burhia.

  20. Inhibition of Proliferation of Vascular Smooth Muscle Cells by Cucurbitanes from Momordica charantia.

    Science.gov (United States)

    Tuan, Nguyen Quoc; Lee, Do-Hyung; Oh, Joonseok; Kim, Chung Sub; Heo, Kyung-Sun; Myung, Chang-Seon; Na, MinKyun

    2017-07-28

    The cucurbitaceous plant Momordica charantia L., named "bitter melon", inhabits Asia, Africa, and South America and has been used as a traditional medicine. The atypical proliferation of vascular smooth muscle cells (VSMCs) plays an important role in triggering the pathogenesis of cardiovascular diseases. Platelet-derived growth factor (PDGF) is regarded as the most powerful growth factor in promoting the intimal accumulation of VSMCs. The current study features the identification of six new cucurbitane-type triterpenoids (1-6) from the fruits of M.  charantia, utilizing diverse chromatographic and spectroscopic techniques. In particular, the 2D structure of 1 was confirmed utilizing the long-range HSQMBC NMR pulse, capable of measuring heteronuclear long-range correlations ( 4-6 J CH ). The cucurbitanes were also assessed for their inhibitory activity against PDGF-induced VSMC proliferation. This current study may constitute a basis for developing those chemotypes into sensible pharmacophores alleviating cardiovascular disorders.

  1. Radix Bupleuri: A Review of Traditional Uses, Botany, Phytochemistry, Pharmacology, and Toxicology.

    Science.gov (United States)

    Yang, Fude; Dong, Xiaoxv; Yin, Xingbin; Wang, Wenping; You, Longtai; Ni, Jian

    2017-01-01

    Radix Bupleuri (Chaihu) has been used as a traditional medicine for more than 2000 years in China, Japan, Korea, and other Asian countries. Phytochemical studies demonstrated that this plant contains essential oils, triterpenoid saponins, polyacetylenes, flavonoids, lignans, fatty acids, and sterols. Crude extracts and pure compounds isolated from Radix Bupleuri exhibited various biological activities, such as anti-inflammatory, anticancer, antipyretic, antimicrobial, antiviral, hepatoprotective, neuroprotective, and immunomodulatory effects. However, Radix Bupleuri could also lead to hepatotoxicity, particularly in high doses and with long-term use. Pharmacokinetic studies have demonstrated that the major bioactive compounds (saikosaponins a, b 2 , c, and d) were absorbed rapidly in rats after oral administration of the extract of Radix Bupleuri . This review aims to comprehensively summarize the traditional uses, botany, phytochemistry, pharmacology, toxicology, and pharmacokinetics of Radix Bupleuri reported to date with an emphasis on its biological properties and mechanisms of action.

  2. Acanthopanax senticosus: review of botany, chemistry and pharmacology.

    Science.gov (United States)

    Huang, Linzhang; Zhao, Hongfang; Huang, Baokang; Zheng, Chengjian; Peng, Wei; Qin, Luping

    2011-02-01

    Acanthopanax senticosus (Rupr. et Maxim) Harms (Araliaceae), also called Siberian Ginseng, Eleutherococcus senticosus, and Ciwujia in Chinese, is a widely used traditional Chinese herb that could invigorate qi, strengthen the spleen, and nourish kidney in the theory of Traditional Chinese Medicine. With high medicinal value, Acanthopanax senticosus (AS, thereafter) is popularly used as an "adaptogen" like Panax ginseng. In recent decades, a great number of chemical, pharmacological, and clinical studies on AS have been carried out worldwide. Several kinds of chemical compounds have been reported, including triterpenoid saponins, lignans, coumarins, and flavones, among which, phenolic compounds such as syringin and eleutheroside E, were considered to be the most active components. Considerable pharmacological experiments both in vitro and in vivo have persuasively demonstrated that AS possessed anti-stress, antiulcer, anti-irradiation, anticancer, anti-inflammatory and hepatoprotective activities, etc. The present review is an up-to-date and comprehensive analysis of the botany, chemistry, pharmacology, toxicity and clinical trials of AS.

  3. Influence of the addition and storage time of crude extract of tea leaves (camellia sinensis l.) toward value of free fatty acid in crude palm oil

    Science.gov (United States)

    Erwin; Wahifiyah, E.; Hairani, R.; Panggabean, A. S.

    2018-04-01

    The purpose of this study was to determine the effect of the crude extract of tea leaves (Camellia sinensis L.) and storage time on the content of free fatty acid in palm oil. The dried tea leaves were macerated and concentrated by rotary evaporator. The extract obtained was added to crude palm oil with various added mass of the extract and various storage times. Phytochemical tests indicated the presence of secondary metabolites including alkaloids, triterpenoids, steroids, phenolics and flavonoids. The ANOVA test showed a decrease in free fatty acid content in crude palm oil with the addition of tea leaves extract. The LSD (Least Significant Difference) test showed the best influence on ALB of palm oil is on the total extract mass of 2 grams and the storage time of 20 days.

  4. Anti-inflammatory effects of seeds of the tropical fruit camu-camu (Myrciaria dubia).

    Science.gov (United States)

    Yazawa, Kazunaga; Suga, Katsumi; Honma, Atsushi; Shirosaki, Miyuki; Koyama, Tomoyuki

    2011-01-01

    The methanolic extract of seeds of the tropical fruit camu-camu was screened for its anti-inflammatory activity in carrageenan-induced paw edema model mice. The extract significantly suppressed both the formation of edema in mice by oral administration and the release of nitric oxide from macrophage-derived RAW 264.7 cells in vitro. Based on the results of a spectroscopic analysis, the active compound was identified by in vivo bioassay-guided fractionation to be 3β-hydroxy-lup-20(29)-en-28-oic acid, betulinic acid, known as an anti-inflammatory triterpenoid. These findings suggest that camu-camu seed extract is a potentially useful material as a source of betulinic acid and as a functional food for prevention of immune-related diseases.

  5. Analgesic and Anti-inflammatory Activity of Teucrium chamaedrys Leaves Aqueous Extract in Male Rats

    Directory of Open Access Journals (Sweden)

    Ali Pourmotabbed

    2010-06-01

    Full Text Available Objective(sCurrent study was undertaken to investigate the analgesic and anti-inflammatory effects of the aqueous extract of Teucrium chamaedrys in mice and rats. Materials and MethodsFor evaluating of analgesic and anti-inflammatory activity, we used the carrageenan- and dextran-induced paw oedema, acetic acid-induced writhing, tail flick and formalin pain tests.ResultsThe extract of T. chamaedrys (50–200 mg/kg and acetylsalicylic acid (100 mg/kg produced a significant (P< 0.01 inhibition of the second phase response in the formalin pain model, while only the high dose (200 mg/kg of the extract showed an analgesic effect in the first phase. The extract also inhibited acetic acid-induced abdominal writhes in a dose-dependent manner. The tail flick latency was dose dependently enhanced by the extract but this was significantly (P< 0.05 lower than that produced by morphine (10 mg/kg. The extract (25–250 mg/kg administered 1 hr before carrageenan-induced paw swelling produced a dose dependent inhibition of the oedema. No effect was observed with the dextran-induced oedema model. Results of the phytochemical screening show the presence of alkaloids, flavonoids and triterpenoids in the extract.ConclusionThe data obtained also suggest that the anti-inflammatory and analgesic effects of the extract may be mediated via both peripheral and central mechanisms. The role of alkaloids, flavonoids and triterpenoids will evaluate in future studies.

  6. Manipulation of saponin biosynthesis by RNA interference-mediated silencing of β-amyrin synthase gene expression in soybean.

    Science.gov (United States)

    Takagi, Kyoko; Nishizawa, Keito; Hirose, Aya; Kita, Akiko; Ishimoto, Masao

    2011-10-01

    Soybean seeds contain substantial amount of diverse triterpenoid saponins that influence the seed quality, although little is known about the physiologic functions of saponins in plants. We now describe the modification of saponin biosynthesis by RNA interference (RNAi)-mediated gene silencing targeted to β-amyrin synthase, a key enzyme in the synthesis of a common aglycon of soybean saponins. We identified two putative β-amyrin synthase genes in soybean that manifested distinct expression patterns with regard to developmental stage and tissue specificity. Given that one of these genes, GmBAS1, was expressed at a much higher level than the other (GmBAS2) in various tissues including the developing seeds, we constructed two RNAi vectors that encode self-complementary hairpin RNAs corresponding to the distinct regions of GmBAS1 under the control of a seed-specific promoter derived from the soybean gene for the α' subunit of the seed storage protein β-conglycinin. These vectors were introduced independently into soybean. Six independent transgenic lines exhibited a stable reduction in seed saponin content, with the extent of saponin deficiency correlating with the β-amyrin synthase mRNA depletion. Although some transgenic lines produced seeds almost devoid of saponins, no abnormality in their growth was apparent and the antioxidant activity of their seeds was similar to that of control seeds. These results suggest that saponins are not required for seed development and survival, and that soybean seeds may therefore be amenable to the modification of triterpenoid saponin content and composition through molecular biologic approaches.

  7. Effects of medium components and culture conditions on mycelial biomass and the production of bioactive ingredients in submerged culture of Xylaria nigripes (Ascomycetes), a Chinese medicinal fungus.

    Science.gov (United States)

    Chen, Jian-Zhi; Lo, Hui-Chen; Lin, Fang-Yi; Chang, Shih-Liang; Hsieh, Changwei; Liang, Zeng-Chin; Ho, Wai-Jane; Hsu, Tai-Hao

    2014-01-01

    The optimal culture conditions were investigated to maximize the production of mycelial biomass and bioactive ingredients in submerged cultivation of Xylaria nigripes, a Chinese medicinal fungus. The one-factor-at-a-time method was used to explore the effects of medium components, including carbon, nitrogen, mineral sources, and initial pH of the medium and environmental factors, such as culture temperature and rotation speed, on mycelial growth and production of bioactive ingredients. The results indicated that the optimal culture temperature and rotation speed were 25°C and 100 rpm in a medium with 20 g fructose, 6 g yeast extract, and 2 g magnesiun sulfate heptahydrate as carbon, nitrogen, and mineral sources, respectively, in 1 L distilled water with an initial medium pH of 5.5. With optimal medium components and conditions of cultivation, the maximal production of mycelial biomass was 6.64 ± 0.88 g/L, with maximal production of bioactive ingredients such as extracellular polysaccharides (2.36 ± 0.18 mg/mL), intracellular polysaccharides (2.38 ± 0.07 mg/g), adenosine (43.27 ± 2.37 mg/g), total polyphenols (36.57 ± 1.36 mg/g), and triterpenoids (31.29 ± 1.17 mg/g) in a shake flask culture. These results suggest that different bioactive ingredients including intracellular polysaccharides, adenosine, total polyphenols and triterpenoids in mycelia and extracellular polysaccharides in broth can be obtained from one simple medium for submerged cultivation of X. nigripes.

  8. Raddeanin A induces human gastric cancer cells apoptosis and inhibits their invasion in vitro

    International Nuclear Information System (INIS)

    Xue, Gang; Zou, Xi; Zhou, Jin-Yong; Sun, Wei; Wu, Jian; Xu, Jia-Li; Wang, Rui-Ping

    2013-01-01

    Highlights: •Raddeanin A is a triterpenoid saponin in herb medicine Anemone raddeana Regel. •Raddeanin A can inhibit 3 kinds of gastric cancer cells’ proliferation and invasion. •Caspase-cascades’ activation indicates apoptosis induced by Raddeanin A. •MMPs, RECK, Rhoc and E-cad are involved in Raddeanin A-induced invasion inhibition. -- Abstract: Raddeanin A is one of the triterpenoid saponins in herbal medicine Anemone raddeana Regel which was reported to suppress the growth of liver and lung cancer cells. However, little was known about its effect on gastric cancer (GC) cells. This study aimed to investigate its inhibitory effect on three kinds of different differentiation stage GC cells (BGC-823, SGC-7901 and MKN-28) in vitro and the possible mechanisms. Proliferation assay and flow cytometry demonstrated Raddeanin A’s dose-dependent inhibitory effect and determined its induction of cells apoptosis, respectively. Transwell assay, wounding heal assay and cell matrix adhesion assay showed that Raddeanin A significantly inhibited the abilities of the invasion, migration and adhesion of the BGC-823 cells. Moreover, quantitative real time PCR and Western blot analysis found that Raddeanin A increased Bax expression while reduced Bcl-2, Bcl-xL and Survivin expressions and significantly activated caspase-3, caspase-8, caspase-9 and poly-ADP ribose polymerase (PARP). Besides, Raddeanin A could also up-regulate the expression of reversion inducing cysteine rich protein with Kazal motifs (RECK), E-cadherin (E-cad) and down-regulate the expression of matrix metalloproteinases-2 (MMP-2), MMP-9, MMP-14 and Rhoc. In conclusion, Raddeanin A inhibits proliferation of human GC cells, induces their apoptosis and inhibits the abilities of invasion, migration and adhesion, exhibiting potential to become antitumor drug

  9. Structural characterization and discrimination of Chinese medicinal materials with multiple botanical origins based on metabolite profiling and chemometrics analysis: Clematidis Radix et Rhizoma as a case study.

    Science.gov (United States)

    Guo, Lin-Xiu; Li, Rui; Liu, Ke; Yang, Jie; Li, Hui-Jun; Li, Song-Lin; Liu, Jian-Qun; Liu, Li-Fang; Xin, Gui-Zhong

    2015-12-18

    Traditional Chinese medicines (TCMs)-based products are becoming more and more popular over the world. To ensure the safety and efficacy, authentication of Chinese medicinal materials has been an important issue, especially for that with multiple botanical origins (one-to-multiple). Taking Clematidis Radix et Rhizoma (CRR) as a case study, we herein developed an integrated platform based on metabolite profiling and chemometrics analysis to characterize, classify, and predict the "one-to-multiple" herbs. Firstly, the predominant constituents, triterpenoid saponins, in three Clematis CRR were rapid characterized by a novel UPLC-QTOF/MS-based strategy, and a total of 49 triterpenoid saponins were identified. Secondly, metabolite profiling was performed by UPLC-QTOF/MS, and 4623 variables were extracted and aligned as dataset. Thirdly, by using pattern recognition analysis, a clear separation of the three Clematis CRR was achieved as well as a total number of 28 variables were screened as the valuable variables for discrimination. By matching with identified saponins, these 28 variables were corresponding to 10 saponins which were identified as marker compounds. Fourthly, based on the relative intensity of the marker compounds-related variables, genetic algorithm optimized support vector machines (GA-SVM) was employed to predict the species of CRR samples. The obtained model showed excellent prediction performance with a prediction accuracy of 100%. Finally, a heatmap visualization was employed for clarifying the distribution of identified saponins, which could be useful for phytochemotaxonomy study of Clematis herbs. These results indicated that our proposed platform was a powerful tool for chemical profiling and discrimination of herbs with multiple botanical origins, providing promising perspectives in tracking the formulation processes of TCMs products. Copyright © 2015 Elsevier B.V. All rights reserved.

  10. Kindia (Pavetteae, Rubiaceae, a new cliff-dwelling genus with chemically profiled colleter exudate from Mt Gangan, Republic of Guinea

    Directory of Open Access Journals (Sweden)

    Martin Cheek

    2018-04-01

    Full Text Available A new genus Kindia (Pavetteae, Rubiaceae is described with a single species, Kindia gangan, based on collections made in 2016 during botanical exploration of Mt Gangan, Kindia, Republic of Guinea in West Africa. The Mt Gangan area is known for its many endemic species including the only native non-neotropical Bromeliaceae Pitcairnia feliciana. Kindia is the fourth endemic vascular plant genus to be described from Guinea. Based on chloroplast sequence data, the genus is part of Clade II of tribe Pavetteae. In this clade, it is sister to Leptactina sensu lato (including Coleactina and Dictyandra. K. gangan is distinguished from Leptactina s.l. by the combination of the following characters: its epilithic habit; several-flowered axillary inflorescences; distinct calyx tube as long as the lobes; a infundibular-campanulate corolla tube with narrow proximal section widening abruptly to the broad distal section; presence of a dense hair band near base of the corolla tube; anthers and style deeply included, reaching about mid-height of the corolla tube; anthers lacking connective appendages and with sub-basal insertion; pollen type 1; pollen presenter (style head winged and glabrous (smooth and usually hairy in Leptactina; orange colleters producing a vivid red exudate, which encircle the hypanthium, and occur inside the calyx and stipules. Kindia is a subshrub that appears restricted to bare, vertical rock faces of sandstone. Fruit dispersal and pollination by bats is postulated. Here, it is assessed as Endangered EN D1 using the 2012 IUCN standard. High resolution LC-MS/MS analysis revealed over 40 triterpenoid compounds in the colleter exudate, including those assigned to the cycloartane class. Triterpenoids are of interest for their diverse chemical structures, varied biological activities, and potential therapeutic value.

  11. Anti-Inflammatory Effects and Mechanisms of Fatsia polycarpa Hayata and Its Constituents

    Directory of Open Access Journals (Sweden)

    Hsueh-Ling Cheng

    2013-01-01

    Full Text Available Fatsia polycarpa, a plant endemic to Taiwan, is an herbal medicine known for treating several inflammation-related diseases, but its biological function needs scientific support. Thus, the anti-inflammatory effects and mechanisms of the methanolic crude extract (MCE of F. polycarpa and its feature constituents, that is, brassicasterol (a phytosterol, triterpenoids 3α-hydroxyolean-11,13(18-dien-28-oic acid (HODA, 3α-hydroxyolean-11-en-28,13β-olide (HOEO, fatsicarpain D, and fatsicarpain F, were investigated. MCE and HOEO, but not brassicasterol, dose-dependently inhibited lipopolysaccharide- (LPS-induced expression of inducible nitric oxide synthase and cyclooxygenase-2 in RAW 264.7 macrophage line, whereas HODA, fatsicarpain D and fatsicarpain F were toxic to RAW cells. Additionally, MCE and HOEO suppressed LPS-induced production of nitric oxide, prostaglandin E2, and interleukin-1β and interfered with LPS-promoted activation of the inhibitor kappa B kinase (IKK/nuclear factor-κB (NF-κB pathway, and that of the mitogen-activated protein kinases (MAPKs extracellular signal regulated kinase (ERK, c-Jun N-terminal kinase (JNK, and p38. In animal tests, MCE and HOEO effectively ameliorated 12-O-tetradecanoylphorobol-13 acetate- (TPA-induced ear edema of mice. Thus, MCE of F. polycarpa exhibited an obvious anti-inflammatory activity in vivo and in vitro that likely involved the inhibition of the IKK/NF-κB pathway and the MAPKs, which may be attributed by triterpenoids such as HOEO.

  12. Raddeanin A induces human gastric cancer cells apoptosis and inhibits their invasion in vitro

    Energy Technology Data Exchange (ETDEWEB)

    Xue, Gang [Department of Oncology, Nanjing University of Chinese Medicine, Nanjing (China); Zou, Xi [Department of Oncology, Affiliated Hospital of Nanjing University of Chinese Medicine, Jiangsu Province Hospital of Traditional Chinese Medicine, Nanjing (China); Zhou, Jin-Yong [Laboratory Center, Affiliated Hospital of Nanjing University of Chinese Medicine, Jiangsu Province Hospital of Traditional Chinese Medicine, Nanjing (China); Sun, Wei [Department of Oncology, Affiliated Hospital of Nanjing University of Chinese Medicine, Jiangsu Province Hospital of Traditional Chinese Medicine, Nanjing (China); Wu, Jian [Laboratory Center, Affiliated Hospital of Nanjing University of Chinese Medicine, Jiangsu Province Hospital of Traditional Chinese Medicine, Nanjing (China); Xu, Jia-Li [Department of Oncology, Nanjing University of Chinese Medicine, Nanjing (China); Wang, Rui-Ping, E-mail: ruipingwang61@hotmail.com [Department of Oncology, Affiliated Hospital of Nanjing University of Chinese Medicine, Jiangsu Province Hospital of Traditional Chinese Medicine, Nanjing (China)

    2013-09-20

    Highlights: •Raddeanin A is a triterpenoid saponin in herb medicine Anemone raddeana Regel. •Raddeanin A can inhibit 3 kinds of gastric cancer cells’ proliferation and invasion. •Caspase-cascades’ activation indicates apoptosis induced by Raddeanin A. •MMPs, RECK, Rhoc and E-cad are involved in Raddeanin A-induced invasion inhibition. -- Abstract: Raddeanin A is one of the triterpenoid saponins in herbal medicine Anemone raddeana Regel which was reported to suppress the growth of liver and lung cancer cells. However, little was known about its effect on gastric cancer (GC) cells. This study aimed to investigate its inhibitory effect on three kinds of different differentiation stage GC cells (BGC-823, SGC-7901 and MKN-28) in vitro and the possible mechanisms. Proliferation assay and flow cytometry demonstrated Raddeanin A’s dose-dependent inhibitory effect and determined its induction of cells apoptosis, respectively. Transwell assay, wounding heal assay and cell matrix adhesion assay showed that Raddeanin A significantly inhibited the abilities of the invasion, migration and adhesion of the BGC-823 cells. Moreover, quantitative real time PCR and Western blot analysis found that Raddeanin A increased Bax expression while reduced Bcl-2, Bcl-xL and Survivin expressions and significantly activated caspase-3, caspase-8, caspase-9 and poly-ADP ribose polymerase (PARP). Besides, Raddeanin A could also up-regulate the expression of reversion inducing cysteine rich protein with Kazal motifs (RECK), E-cadherin (E-cad) and down-regulate the expression of matrix metalloproteinases-2 (MMP-2), MMP-9, MMP-14 and Rhoc. In conclusion, Raddeanin A inhibits proliferation of human GC cells, induces their apoptosis and inhibits the abilities of invasion, migration and adhesion, exhibiting potential to become antitumor drug.

  13. Steroid-like compounds in Chinese medicines promote blood circulation via inhibition of Na+/K+ -ATPase.

    Science.gov (United States)

    Chen, Ronald J Y; Chung, Tse-yu; Li, Feng-yin; Yang, Wei-hung; Jinn, Tzyy-rong; Tzen, Jason T C

    2010-06-01

    To examine if steroid-like compounds found in many Chinese medicinal products conventionally used for the promotion of blood circulation may act as active components via the same molecular mechanism triggered by cardiac glycosides, such as ouabain. The inhibitory potency of ouabain and the identified steroid-like compounds on Na(+)/K(+)-ATPase activity was examined and compared. Molecular modeling was exhibited for the docking of these compounds to Na(+)/K(+)-ATPase. All the examined steroid-like compounds displayed more or less inhibition on Na(+)/K(+)-ATPase, with bufalin (structurally almost equivalent to ouabain) exhibiting significantly higher inhibitory potency than the others. In the pentacyclic triterpenoids examined, ursolic acid and oleanolic acid were moderate inhibitors of Na(+)/K(+)-ATPase, and their inhibitory potency was comparable to that of ginsenoside Rh2. The relatively high inhibitory potency of ursolic acid or oleanolic acid was due to the formation of a hydrogen bond between its carboxyl group and the Ile322 residue in the deep cavity close to two K(+) binding sites of Na(+)/K(+)-ATPase. Moreover, the drastic difference observed in the inhibitory potency of ouabain, bufalin, ginsenoside Rh2, and pentacyclic triterpenoids is ascribed mainly to the number of hydrogen bonds and partially to the strength of hydrophobic interaction between the compounds and residues around the deep cavity of Na(+)/K(+)-ATPase. Steroid-like compounds seem to contribute to therapeutic effects of many cardioactive Chinese medicinal products. Chinese herbs, such as Prunella vulgaris L, rich in ursolic acid, oleanolic acid and their glycoside derivatives may be adequate sources for cardiac therapy via effective inhibition on Na(+)/K(+)-ATPase.

  14. Effect of aqueous extracts of Achyranthes aspera Linn. on experimental animal model for inflammation.

    Science.gov (United States)

    Bhosale, Uma A; Yegnanarayan, Radha; Pophale, Prachi; Somani, Rahul

    2012-04-01

    Achyranthes aspera is known as Chirchita (Hindi), Apamarga (Sanskrit), Aghedi (Gujarati), Apang (Bengali), Nayurivi (Tamil), Kalalat (Malyalam) and Agadha (Marathi) in our country. It possesses valuable medicinal properties and used in treatment of cough, bronchitis and rheumatism, malarial fever, dysentery, asthma, hypertension and diabetes in Indian folklore. Present study was designed to evaluate anti-inflammatory activity of an aqueous extracts of Achyranthes aspera (AEAA). AEAA leaves and whole plant (i.e. Aqueous extracts of Achyranthes aspera leaves (AEAAL)/Aqueous extracts of A. aspera whole plant (AEAAW) were studied in albino mice using carrageenan induced left hind paw edema. Both extracts were subjected to preliminary phytochemical analysis and acute toxicity of the extracts was also studied using Organization for Economic Co-operation and Development OECD guidelines 423. Acute toxicity study confirmed toxic dose of AEAA to be more than 2,000 mg/kg. Flavonoids, alkaloids, saponins and triterpenoids were the major constituents found in extracts. AEAA reduced the edema induced by carrageenan by 35.71-54.76% on intraperitoneally administration of 400 mg/kg and 800 mg/kg as compared to the untreated control group. Diclofenac sodium at 10 mg/kg inhibited the edema volume by 42.85%. The results indicated that the AEAA 800 mg/kg body weight shows more significant (P < 0.01, P < 0.001) anti-inflammatory activity when compared with the standard and untreated control respectively. Both AEAA exhibit promising anti-inflammatory activity attributed to flavonoids, alkaloids, saponins and triterpenoids phytoconstituents.

  15. Identification and genome organization of saponin pathway genes from a wild crucifer, and their use for transient production of saponins in Nicotiana benthamiana.

    Science.gov (United States)

    Khakimov, Bekzod; Kuzina, Vera; Erthmann, Pernille Ø; Fukushima, Ery Odette; Augustin, Jörg M; Olsen, Carl Erik; Scholtalbers, Jelle; Volpin, Hanne; Andersen, Sven Bode; Hauser, Thure P; Muranaka, Toshiya; Bak, Søren

    2015-11-01

    The ability to evolve novel metabolites has been instrumental for the defence of plants against antagonists. A few species in the Barbarea genus are the only crucifers known to produce saponins, some of which make plants resistant to specialist herbivores, like Plutella xylostella, the diamondback moth. Genetic mapping in Barbarea vulgaris revealed that genes for saponin biosynthesis are not clustered but are located in different linkage groups. Using co-location with quantitative trait loci (QTLs) for resistance, transcriptome and genome sequences, we identified two 2,3-oxidosqualene cyclases that form the major triterpenoid backbones. LUP2 mainly produces lupeol, and is preferentially expressed in insect-susceptible B. vulgaris plants, whereas LUP5 produces β-amyrin and α-amyrin, and is preferentially expressed in resistant plants; β-amyrin is the backbone for the resistance-conferring saponins in Barbarea. Two loci for cytochromes P450, predicted to add functional groups to the saponin backbone, were identified: CYP72As co-localized with insect resistance, whereas CYP716As did not. When B. vulgaris sapogenin biosynthesis genes were transiently expressed by CPMV-HT technology in Nicotiana benthamiana, high levels of hydroxylated and carboxylated triterpenoid structures accumulated, including oleanolic acid, which is a precursor of the major resistance-conferring saponins. When the B. vulgaris gene for sapogenin 3-O-glucosylation was co-expressed, the insect deterrent 3-O-oleanolic acid monoglucoside accumulated, as well as triterpene structures with up to six hexoses, demonstrating that N. benthamiana further decorates the monoglucosides. We argue that saponin biosynthesis in the Barbarea genus evolved by a neofunctionalized glucosyl transferase, whereas the difference between resistant and susceptible B. vulgaris chemotypes evolved by different expression of oxidosqualene cyclases (OSCs). © 2015 The Authors The Plant Journal © 2015 John Wiley & Sons

  16. Tannin diagenesis in mangrove leaves from a tropical estuary: a novel molecular approach

    Science.gov (United States)

    Hernes, Peter J.; Benner, Ronald; Cowie, Gregory L.; Goñi, Miguel A.; Bergamaschi, Brian A.; Hedges, John I.

    2001-09-01

    Molecular-level condensed tannin analyses were conducted on a series of mangrove (Rhizophora mangle) leaves at various stages of decomposition in a tropical estuary. Total molecular tannin yields ranged from 0.5% ash-free dry weight (AFDW) in the most highly degraded black leaves (6-7 weeks in the water) up to >7% AFDW in fresh leaves (80% procyanidin (PC) with the remainder being prodelphinidin (PD). PD tannin, with its higher degree of hydroxylation, proved to be more labile than PC tannin. Average chain length of condensed tannin (degree of polymerization) exhibited an initial increase in response to leaching, but later decreased in the subsequent shift toward abiotic or microbially mediated chemical reactions. Several trends point toward a possible condensation reaction in which tannin plays a role in nitrogen immobilization. These include an apparent inverse correlation between molecular tannin and nitrogen, a positive correlation between molecular tannin and percent basic amino acids, 13C-NMR data indicating transformation of tannin as opposed to remineralization, and 13C-NMR data showing loss of condensed tannin B-ring phenolic carbons coupled with preservation of A-ring phenolic carbon. In addition to condensed tannin, the molecular method used also yielded several triterpenoids. Triterpenoids accounted for up to 3.5% AFDW of the leaf material and exhibited a threefold increase between yellow senescent leaves entering the estuary and black leaves. This trend is likely due to the weakening of protective cuticular membranes during leaf decomposition, which leads to increased yields in the acidic conditions used for tannin analyses.

  17. Ursolic acid improves domoic acid-induced cognitive deficits in mice

    Energy Technology Data Exchange (ETDEWEB)

    Wu, Dong-mei [School of Environment and Spatial Informatics, China University of Mining and Technology, Xuzhou 221008, Jiangsu Province (China); Key Laboratory for Biotechnology on Medicinal Plants of Jiangsu Province, School of Life Science, Xuzhou Normal University, Xuzhou 221116, Jiangsu Province (China); Lu, Jun, E-mail: lu-jun75@163.com [Key Laboratory for Biotechnology on Medicinal Plants of Jiangsu Province, School of Life Science, Xuzhou Normal University, Xuzhou 221116, Jiangsu Province (China); Zhang, Yan-qiu [School of Environment and Spatial Informatics, China University of Mining and Technology, Xuzhou 221008, Jiangsu Province (China); Zheng, Yuan-lin, E-mail: ylzheng@xznu.edu.cn [Key Laboratory for Biotechnology on Medicinal Plants of Jiangsu Province, School of Life Science, Xuzhou Normal University, Xuzhou 221116, Jiangsu Province (China); Hu, Bin [Key Laboratory for Biotechnology on Medicinal Plants of Jiangsu Province, School of Life Science, Xuzhou Normal University, Xuzhou 221116, Jiangsu Province (China); Cheng, Wei [School of Environment and Spatial Informatics, China University of Mining and Technology, Xuzhou 221008, Jiangsu Province (China); Zhang, Zi-feng; Li, Meng-qiu [Key Laboratory for Biotechnology on Medicinal Plants of Jiangsu Province, School of Life Science, Xuzhou Normal University, Xuzhou 221116, Jiangsu Province (China)

    2013-09-01

    Our previous findings suggest that mitochondrial dysfunction is the mechanism underlying cognitive deficits induced by domoic acid (DA). Ursolic acid (UA), a natural triterpenoid compound, possesses many important biological functions. Evidence shows that UA can activate PI3K/Akt signaling and suppress Forkhead box protein O1 (FoxO1) activity. FoxO1 is an important regulator of mitochondrial function. Here we investigate whether FoxO1 is involved in the oxidative stress-induced mitochondrial dysfunction in DA-treated mice and whether UA inhibits DA-induced mitochondrial dysfunction and cognitive deficits through regulating the PI3K/Akt and FoxO1 signaling pathways. Our results showed that FoxO1 knockdown reversed the mitochondrial abnormalities and cognitive deficits induced by DA in mice through decreasing HO-1 expression. Mechanistically, FoxO1 activation was associated with oxidative stress-induced JNK activation and decrease of Akt phosphorylation. Moreover, UA attenuated the mitochondrial dysfunction and cognitive deficits through promoting Akt phosphorylation and FoxO1 nuclear exclusion in the hippocampus of DA-treated mice. LY294002, an inhibitor of PI3K/Akt signaling, significantly decreased Akt phosphorylation in the hippocampus of DA/UA mice, which weakened UA actions. These results suggest that UA could be recommended as a possible candidate for the prevention and therapy of cognitive deficits in excitotoxic brain disorders. - Highlights: • Ursolic acid (UA) is a naturally triterpenoid compound. • UA attenuated the mitochondrial dysfunction and cognitive deficits. • Mechanistically, UA activates PI3K/Akt signaling and suppresses FoxO1 activity. • UA could be recommended as a possible candidate for anti-excitotoxic brain disorders.

  18. Ursolic acid improves domoic acid-induced cognitive deficits in mice

    International Nuclear Information System (INIS)

    Wu, Dong-mei; Lu, Jun; Zhang, Yan-qiu; Zheng, Yuan-lin; Hu, Bin; Cheng, Wei; Zhang, Zi-feng; Li, Meng-qiu

    2013-01-01

    Our previous findings suggest that mitochondrial dysfunction is the mechanism underlying cognitive deficits induced by domoic acid (DA). Ursolic acid (UA), a natural triterpenoid compound, possesses many important biological functions. Evidence shows that UA can activate PI3K/Akt signaling and suppress Forkhead box protein O1 (FoxO1) activity. FoxO1 is an important regulator of mitochondrial function. Here we investigate whether FoxO1 is involved in the oxidative stress-induced mitochondrial dysfunction in DA-treated mice and whether UA inhibits DA-induced mitochondrial dysfunction and cognitive deficits through regulating the PI3K/Akt and FoxO1 signaling pathways. Our results showed that FoxO1 knockdown reversed the mitochondrial abnormalities and cognitive deficits induced by DA in mice through decreasing HO-1 expression. Mechanistically, FoxO1 activation was associated with oxidative stress-induced JNK activation and decrease of Akt phosphorylation. Moreover, UA attenuated the mitochondrial dysfunction and cognitive deficits through promoting Akt phosphorylation and FoxO1 nuclear exclusion in the hippocampus of DA-treated mice. LY294002, an inhibitor of PI3K/Akt signaling, significantly decreased Akt phosphorylation in the hippocampus of DA/UA mice, which weakened UA actions. These results suggest that UA could be recommended as a possible candidate for the prevention and therapy of cognitive deficits in excitotoxic brain disorders. - Highlights: • Ursolic acid (UA) is a naturally triterpenoid compound. • UA attenuated the mitochondrial dysfunction and cognitive deficits. • Mechanistically, UA activates PI3K/Akt signaling and suppresses FoxO1 activity. • UA could be recommended as a possible candidate for anti-excitotoxic brain disorders

  19. Impressic acid from Acanthopanax koreanum, possesses matrix metalloproteinase-13 down-regulating capacity and protects cartilage destruction.

    Science.gov (United States)

    Lim, Hyun; Min, Dong Suk; Yun, Han Eul; Kim, Kil Tae; Sun, Ya Nan; Dat, Le Duc; Kim, Young Ho; Kim, Hyun Pyo

    2017-09-14

    Acanthopanax koreanum (Araliaceae) has been used in traditional medicine for enhancing vitality, rheumatism, and bone-related pains. But its activity on cartilage protection has not been known yet. Matrix metalloproteinase (MMP)-13 has an important role in degrading cartilage materials under pathologic conditions such as arthritis. The present study was designed to find the inhibitory activity of impressic acid on MMP-13 expression and cartilage protective action. 70% ethanol extract of Acanthopanax koreanum leaves and impressic acid, a major constituent isolated from the same plant materials, were examined on MMP-13 down-regulating capacity in IL-1β-treated human chondrocyte cell line (SW1353) and rabbit cartilage explants. In IL-1β-treated SW1353 cells, impressic acid significantly and concentration-dependently inhibited MMP-13 expression at 0.5-10μM. Impressic acid was found to be able to inhibit MMP-13 expression by blocking the phosphorylation of signal transducer and activator of transcription-1/-2 (STAT-1/-2) and activation of c-Jun and c-Fos among the cellular signaling pathways involved. Further, impressic acid was found to inhibit the expression of MMP-13 mRNA (47.7% inhibition at 10μM), glycosaminoglycan release (42.2% reduction at 10μM) and proteoglycan loss in IL-1-treated rabbit cartilage explants culture. In addition, a total of 21 lupane-type triterpenoids structurally-related to impressic acid were isolated from the same plant materials and their suppressive activities against MMP-13 expression were also examined. Among these derivatives, compounds 2, 3, 16, and 18 clearly down-regulated MMP-13 expression. However, impressic acid was more potent than these derivatives in down-regulating MMP-13 expression. Impressic acid, its related triterpenoids, and A. koreanum extract have potential as therapeutic agents to prevent cartilage degradation by inhibiting matrix protein degradation. Copyright © 2017 Elsevier Ireland Ltd. All rights reserved.

  20. Petrographic and biomarker analysis of xylite-rich coal from the Kolubara and Kostolac lignite basins (Pannonian Basin, Serbia)

    Science.gov (United States)

    Đoković, Nataša; Mitrović, Danica; Životić, Dragana; Bechtel, Achim; Sachsenhofer, Reinhard F.; Stojanović, Ksenija

    2018-02-01

    The maceral and biomarker characteristics of 4 sublithotypes of xylite-rich coal (SXCs), pale yellow, dark yellow, brown and black, originating from the Kolubara and Kostolac lignite basins were determined. Based on these results, differences in sources and changes of organic matter (OM) resulting in formation of 4 SXCs were established. Conifers (particularly Cupressaceae, Taxodiaceae and Pinacea) had a significant impact on the precursor OM of all SXCs. The contribution of gymnosperm vs. angiosperm vegetation decreased in order pale yellow SXC>dark yellow SXC>brown SXC>black SXC. The distribution of non-hopanoid triterpenoids indicates that change of SXC colour from yellow to black is associated with reduced input of angiosperm plants from the Betulacea family. Differences in hopane distribution, bitumen content, proportion of short-chain n-alkanes and degree of aromatization of di- and triterpenoids of pale yellow SXC are controlled by microbial communities which took part in the diagenetic alteration of OM. The content of total huminites increased from black to pale yellow SXC, whereas contents of total liptinite and inertinite macerals showed the opposite trend. SXCs differ according to textinite/ulminite ratio, which sharply decreased from pale yellow to black SXC, reflecting increase in gelification of woody tissue. Regarding the composition of liptinite macerals, the SXCs mostly differ according to resinite/liptodetrinite and resinite/suberinite ratios, which are higher in yellow than in brown and black SXC. This result along with values of TOC/N ratio and Carbon Preference Index indicate that the contribution of well preserved woody material, including lignin tissue vs. the impact of epicuticular waxes decreased from yellow to black SXC.