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Sample records for oleanane triterpenoid cddo-me

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

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    Deeb, Dorrah; Gao, Xiaohua [Department of General Surgery, Henry Ford Health System, Detroit, MI 48202 (United States); Arbab, Ali S. [Department of Diagnostic Radiology, Henry Ford Health System, Detroit, MI 48202 (United States); Barton, Kenneth [Department of Radiation Oncology, Henry Ford Health System, Detroit, MI 48202 (United States); Dulchavsky, Scott A., E-mail: sgautam1@hfhs.org; Gautam, Subhash C., E-mail: sgautam1@hfhs.org [Department of General Surgery, Henry Ford Health System, Detroit, MI 48202 (United States)

    2010-10-13

    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.

  2. 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.

  3. The triterpenoid CDDO-Me inhibits bleomycin-induced lung inflammation and fibrosis.

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    Ajit A Kulkarni

    Full Text Available Pulmonary Fibrosis (PF is a devastating progressive disease in which normal lung structure and function is compromised by scarring. Lung fibrosis can be caused by thoracic radiation, injury from chemotherapy and systemic diseases such as rheumatoid arthritis that involve inflammatory responses. CDDO-Me (Methyl 2-cyano-3,12-dioxooleana-1,9(11dien-28-oate, Bardoxolone methyl is a novel triterpenoid with anti-fibrotic and anti-inflammatory properties as shown by our in vitro studies. Based on this evidence, we hypothesized that CDDO-Me would reduce lung inflammation, fibrosis and lung function impairment in a bleomycin model of lung injury and fibrosis. To test this hypothesis, mice received bleomycin via oropharyngeal aspiration (OA on day zero and CDDO-Me during the inflammatory phase from days -1 to 9 every other day. Bronchoalveolar lavage fluid (BALF and lung tissue were harvested on day 7 to evaluate inflammation, while fibrosis and lung function were evaluated on day 21. On day 7, CDDO-Me reduced total BALF protein by 50%, alveolar macrophage infiltration by 40%, neutrophil infiltration by 90% (p≤0.01, inhibited production of the inflammatory cytokines KC and IL-6 by over 90% (p≤0.001, and excess production of the pro-fibrotic cytokine TGFβ by 50%. CDDO-Me also inhibited α-smooth muscle actin and fibronectin mRNA by 50% (p≤0.05. On day 21, CDDO-Me treatment reduced histological fibrosis, collagen deposition and αSMA production. Lung function was significantly improved at day 21 by treatment with CDDO-Me, as demonstrated by respiratory rate and dynamic compliance. These new findings reveal that CDDO-Me exhibits potent anti-fibrotic and anti-inflammatory properties in vivo. CDDO-Me is a potential new class of drugs to arrest inflammation and ameliorate fibrosis in patients who are predisposed to lung injury and fibrosis incited by cancer treatments (e.g. chemotherapy and radiation and by systemic autoimmune diseases.

  4. Preclinical evidences toward the use of triterpenoid CDDO-Me for solid cancer prevention and treatment.

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    Wang, Yan-Yang; Zhe, Hong; Zhao, Ren

    2014-02-20

    Solid cancer remains a major cause of death in the world. As limited treatment options are currently available to patients with solid cancer, novel preventive control and effective therapeutic approaches are considered to be reasonable and decisive measures to combat this disease. The plant-derived triterpenoids, commonly used for medicinal purposes in many Asian countries, poses various pharmacological properties. A large number of triterpenoids exhibit cytotoxicity against a variety of cancer cells, and cancer preventive, as well as anticancer efficacy in preclinical animal models. To improve antitumor activity, some synthetic triterpenoid derivatives have been synthesized, including cyano-3,12-dioxooleana-1,9(11)- dien-28-oic (CDDO), its methyl ester (CDDO-Me), and imidazolide (CDDO-Im) derivatives. In this review, we will critically examine the current preclinical evidences of cancer preventive and therapeutic activity about one of the synthetic triterpenoids, CDDO-Me. Both in vitro and in vivo effects of this agent and related molecular mechanisms are presented.

  5. CDDO-Me Redirects Activation of Breast Tumor Associated Macrophages.

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    Michael S Ball

    Full Text Available Tumor-associated macrophages can account for up to 50% of the tumor mass in breast cancer patients and high TAM density is associated with poor clinical prognosis. Because TAMs enhance tumor growth, development, and metastatic potential, redirection of TAM activation may have significant therapeutic benefit. Our studies in primary human macrophages and murine breast TAMs suggest that the synthetic oleanane triterpenoid CDDO-methyl ester (CDDO-Me reprograms the activation profile of TAMs from tumor-promoting to tumor-inhibiting. We show that CDDO-Me treatment inhibits expression of IL-10 and VEGF in stimulated human M2 macrophages and TAMs but increases expression of TNF-α and IL-6. Surface expression of CD206 and CD163, which are characteristic of M2 activation, is significantly attenuated by CDDO-Me. In contrast, CDDO-Me up-regulates surface expression of HLA-DR and CD80, which are markers of M1 activation, and importantly potentiates macrophage activation of autologous T cells but inhibits endothelial cell vascularization. These results show for the first time that CDDO-Me redirects activation of M2 macrophages and TAMs from immune-suppressive to immune-stimulatory, and implicate a role for CDDO-Me as an immunotherapeutic in the treatment of breast and potentially other types of cancer.

  6. Hsp90 Is a Novel Target Molecule of CDDO-Me in Inhibiting Proliferation of Ovarian Cancer Cells.

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    Dong-Jun Qin

    Full Text Available Synthetic triterpenoid methyl-2-cyano-3, 12-dioxooleana-1, 9(11-dien-28-oate (CDDO-Me has been shown as a promising agent against ovarian cancer. However, the underlying mechanism is not well understood. Here, we demonstrate that CDDO-Me directly interacts with Hsp90 in cells by cellular thermal shift assay. CDDO-Me treatment leads to upregulation of Hsp70 and degradation of Hsp90 clients (ErbB2 and Akt, indicating the inhibition of Hsp90 by CDDO-Me in cells. Knockdown of Hsp90 significantly inhibits cell proliferation and enhances the anti-proliferation effect of CDDO-Me in H08910 ovarian cancer cells. Dithiothreitol inhibits the interaction of CDDO-Me with Hsp90 in cells and abrogates CDDO-Me induced upregulation of Hsp70, degradation of Akt and cell proliferation inhibition. This suggests the anti-ovarian cancer effect of CDDO-Me is possibly mediated by the formation of Michael adducts between CDDO-Me and reactive nucleophiles on Hsp90. This study identifies Hsp90 as a novel target protein of CDDO-Me, and provides a novel insight into the mechanism of action of CDDO-Me in ovarian cancer cells.

  7. Bardoxolone methyl (CDDO-Me) as a therapeutic agent: an update on its pharmacokinetic and pharmacodynamic properties.

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    Wang, Yan-Yang; Yang, Yin-Xue; Zhe, Hong; He, Zhi-Xu; Zhou, Shu-Feng

    2014-01-01

    Triterpenoids have been used for medicinal purposes in many Asian countries because of their anti-inflammatory, antioxidant, antiproliferative, anticancer, and anticarcinogenic properties. Bardoxolone methyl, the C-28 methyl ester of 2-cyano-3,12-dioxoolean-1,9-dien-28-oic acid (CDDO) known as CDDO-Me or RTA 402, is one of the derivatives of synthetic triterpenoids. CDDO-Me has been used for the treatment of chronic kidney disease, cancer (including leukemia and solid tumors), and other diseases. In this review, we will update our knowledge of the clinical pharmacokinetics and pharmacodynamics of CDDO-Me, highlighting its clinical benefits and the underlying mechanisms involved. The role of the Kelch-like erythroid cell-derived protein with CNC homology-associated protein 1 (Keap1)/the nuclear factor erythroid 2-related factor 2 (Nrf2) pathway in the therapeutic activities of CDDO-Me will be discussed. CDDO-Me contains α,β-unsaturated carbonyl groups on rings A and C that can generate reversible adducts with the thiol groups of Cys residues in target proteins such as Keap1 and IκB kinase. At low nanomolar concentrations, CDDO-Me protects the cells against oxidative stress via inhibition of reactive oxygen species generation, while CDDO-Me at low micromolar concentrations induces apoptosis by increasing reactive oxygen species and decreasinging intracellular glutathione levels. Through Keap1/Nrf2 and nuclear factor-κB pathways, this agent can modulate the activities of a number of important proteins that regulate inflammation, redox balance, cell proliferation and programmed cell death. In a Phase I trial in cancer patients, CDDO-Me was found to have a slow and saturable oral absorption, a relatively long terminal phase half-life (39 hours at 900 mg/day), nonlinearity (dose-dependent) at high doses (600-1,300 mg/day), and high interpatient variability. As a multifunctional agent, CDDO-Me has improved the renal function in patients with chronic kidney disease

  8. Chemical and Biological Characterization of Oleanane Triterpenoids from Soy

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    David G. Popovich

    2009-08-01

    Full Text Available Soyasaponins are a group of complex and structural diverse oleanane triterpenoids found in soy (Glycine max and other legumes. They are primarily classified into two main groups − group A and B − based on the attachment of sugar moieties at positions C-3 and C-22 of the ring structures. Group A soyasaponins are bidesmosidic, while group B soyasaponins are monodesmosidic. Group B soyasaponins are further classified into two subcategories known as 2,3-dihydro-2,5-dihydroxy-6 -methyl-4H-pyran-4-one (DDMP and non-DDMP conjugated molecules. The preparation and purification of soyasaponin molecules is complicated by the presence of bioactive soy isoflavones, which often overlap with soyasaponin in polarity and must removed from extracts before biological assessment. Soyasaponin extracts, aglycones of group A and B and individual group B soyasaponins such as soyasaponin I have been reported to posses specific bioactive properties, such as in vitro anti-cancer properties by modulating the cell cycle and inducing apoptosis. The isolation, chemical characterization and detection strategies by HPLC and HPLC-MS are reviewed, along with the reported bioactive effects of soyasaponin extracts and individual molecules in cultured cancer cell experiments.

  9. Therapeutic effects of C-28 methyl ester of 2-cyano-3,12-dioxoolean-1,9-dien-28-oic acid (CDDO-Me; bardoxolone methyl) on radiation-induced lung inflammation and fibrosis in mice.

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    Wang, Yan-Yang; Zhang, Cui-Ying; Ma, Ya-Qiong; He, Zhi-Xu; Zhe, Hong; Zhou, Shu-Feng

    2015-01-01

    The C-28 methyl ester of 2-cyano-3,12-dioxoolean-1,9-dien-28-oic acid (CDDO-Me), one of the synthetic triterpenoids, has been found to have potent anti-inflammatory and anticancer properties in vitro and in vivo. However, its usefulness in mitigating radiation-induced lung injury (RILI), including radiation-induced lung inflammation and fibrosis, has not been tested. The aim of this study was to explore the therapeutic effect of CDDO-Me on RILI in mice and the underlying mechanisms. Herein, we found that administration of CDDO-Me improved the histopathological score, reduced the number of inflammatory cells and concentrations of total protein in bronchoalveolar lavage fluid, suppressed secretion and expression of proinflammatory cytokines, including transforming growth factor-β and interleukin-6, elevated expression of the anti-inflammatory cytokine interleukin-10, and downregulated the mRNA level of profibrotic genes, including for fibronectin, α-smooth muscle actin, and collagen I. CDDO-Me attenuated radiation-induced lung inflammation. CDDO-Me also decreased the Masson's trichrome stain score, hydroxyproline content, and mRNA level of profibrotic genes, and blocked radiation-induced collagen accumulation and fibrosis. Collectively, these findings suggest that CDDO-Me ameliorates radiation-induced lung inflammation and fibrosis, and this synthetic triterpenoid is a promising novel therapeutic agent for RILI. Further mechanistic, efficacy, and safety studies are warranted to elucidate the role of CDDO-Me in the management of RILI.

  10. Bardoxolone methyl (CDDO-Me as a therapeutic agent: an update on its pharmacokinetic and pharmacodynamic properties

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    Wang YY

    2014-10-01

    Full Text Available Yan-Yang Wang,1,2 Yin-Xue Yang,3 Hong Zhe,1 Zhi-Xu He,4 Shu-Feng Zhou2,4 1Department of Radiation Oncology, General Hospital of Ningxia Medical University, Yinchuan, Ningxia, People’s Republic of China; 2Department of Pharmaceutical Sciences, College of Pharmacy, University of South Florida, Tampa, FL, USA; 3Department of Colon-rectal Surgery, General Hospital of Ningxia Medical University, Yinchuan, Ningxia, People’s Republic of China; 4Guizhou 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, Guizhou, People’s Republic of China Abstract: Triterpenoids have been used for medicinal purposes in many Asian countries because of their anti-inflammatory, antioxidant, antiproliferative, anticancer, and anticarcinogenic properties. Bardoxolone methyl, the C-28 methyl ester of 2-cyano-3,12-dioxoolean-1,9-dien-28-oic acid (CDDO known as CDDO-Me or RTA 402, is one of the derivatives of synthetic triterpenoids. CDDO-Me has been used for the treatment of chronic kidney disease, cancer (including leukemia and solid tumors, and other diseases. In this review, we will update our knowledge of the clinical pharmacokinetics and pharmacodynamics of CDDO-Me, highlighting its clinical benefits and the underlying mechanisms involved. The role of the Kelch-like erythroid cell-derived protein with CNC homology-associated protein 1 (Keap1/the nuclear factor erythroid 2-related factor 2 (Nrf2 pathway in the therapeutic activities of CDDO-Me will be discussed. CDDO-Me contains a,ß-unsaturated carbonyl groups on rings A and C that can generate reversible adducts with the thiol groups of Cys residues in target proteins such as Keap1 and IκB kinase. At low nanomolar concentrations, CDDO-Me protects the cells against oxidative stress via inhibition of reactive oxygen species generation, while CDDO-Me at low micromolar

  11. Three new oleanane triterpenoid saponins acetylated with monoterpenoid acid from Albizia julibrissin.

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    Zheng, Lu; Zheng, Jian; Zhang, Qingying; Wang, Bin; Zhao, Yuying; Wu, Lijun

    2010-10-01

    Three new minor oleanane triterpenoid saponins acetylated with monoterpenoid acid, julibroside J(32), julibroside J(35) and julibroside J(36), along with one new natural product, prosapogenin 9, were isolated from the stem bark of Albizia julibrissin. Their structures were elucidated on the basis of the chemical and spectroscopic evidences.

  12. Two New Oleanane-type Triterpenoids from Methanolyzed Saponins of Momordica cochinchinensis.

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    Fan, Rong; Cheng, Rong-Rong; Zhu, Hong-Tao; Wang, Dong; Yang, Chong-Ren; Xua, Min; Zhang, Ying-Jun

    2016-06-01

    Two new oleanane-type triterpenoid saponins (1 and 2) were isolated from the methanolyzed total saponins of the seeds of Momordica cochinchinensis (Lour.) Spreng, together with 16 known compounds (3-18). Their structures were elucidated on the basis of detailed spectroscopic, including 1D and 2D NMR, mass spectrometric, methanolysis and LC-MS analysis. All the isolates were tested for their cytotoxic activities against five human cancer cell lines (HL-60, SMMC-7721, PANC-1, A-549, and SW-480) and the glucose uptake activity. The known compound 6 exhibited toxic effects against HL-60 with an IC50 value of 18.1 μM, while 10 showed cytotoxicity against SMMC-7721 and A-549 cell lines, with IC50 values of 34.4 and 32.8 μM, respectively. In addition, the new compound 2 showed glucose uptake activity with a glucose consumption value of 0.29 μM at 10 μM concentration.

  13. Proteomic analysis shows synthetic oleanane triterpenoid binds to mTOR.

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    Mark M Yore

    Full Text Available New multifunctional drugs that target multiple disease-relevant networks offer a novel approach to the prevention and treatment of many diseases. New synthetic oleanane triterpenoids (SO, such as CDDO (2-cyano-3,12-dioxooleana-1,9-dien-28-oic acid and its derivatives, are multifunctional compounds originally developed for the prevention and treatment of inflammation and oxidative stress. However, the protein binding partners and mechanisms of action of these SO are not yet fully understood. Here we characterize the putative target profile of one SO, CDDO-Imidazolide (CDDO-Im, by combining affinity purification with mass spectroscopic proteomic analysis to identify 577 candidate binding proteins in whole cells. This SO pharmaco-interactome consists of a diverse but interconnected set of signaling networks; bioinformatic analysis of the protein interactome identified canonical signaling pathways targeted by the SO, including retinoic acid receptor (RAR, estrogen receptor (ER, insulin receptor (IR, janus kinase/signal transducers and activators of transcription (JAK/STAT, and phosphatase and tensin homolog (PTEN. Pull-down studies then further validated a subset of the putative targets. In addition, we now show for the first time that the mammalian target of rapamycin (mTOR is a direct target of CDDO-Im. We also show that CDDO-Im blocks insulin-induced activation of this pathway by binding to mTOR and inhibiting its kinase activity. Our basic studies confirm that the SO, CDDO-Im, acts on a protein network to elicit its pharmacological activity.

  14. An unusual bioactive oleanane triterpenoid from Rhododendron campanulatum D.Don

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    Mudasir Ahmad Tantry; Reehana Khan; Seema Akbar; Abdul Rouf Dar; Abdul Sami Shawl; Mohammad Sarwar Alam

    2011-01-01

    An unusual oleanane triterpene (1) was isolated from aerial parts of Rhododendron campanulatum. The compound had shown prominent antibacterial and immunomodulatory activities. The structure of the compound was determined by spectroscopic data including ID and 2D NMR spectral analysis.

  15. The effect of ex vivo CDDO-Me activation on nuclear factor erythroid 2-related factor 2 pathway in white blood cells from patients with septic shock.

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    Noel, Sanjeev; Zheng, Laura; Navas-Acien, Ana; Fuchs, Ralph J

    2014-11-01

    Nuclear factor erythroid 2-related factor 2 (NRF2) has been shown to protect against experimental sepsis in mice and lipopolysaccharide (LPS)-induced inflammation in ex vivo white blood cells from healthy subjects by upregulating cellular antioxidant genes. The objective of this study was to test the hypothesis that ex vivo methyl 2-cyano-3,12-dioxoolean-1,9-dien-28-oate (CDDO-Me) activates NRF2-regulated antioxidant genes in white blood cells from patients with septic shock and protects against LPS-induced inflammation and reactive oxidative species production. Peripheral blood was collected from 18 patients with septic shock who were being treated in medical and surgical intensive care units. Real-time polymerase chain reaction was used to quantify the expression of NRF2 target genes (NQO1, HO-1, GCLM, and FTL) and IL-6 in peripheral blood mononuclear cells (PBMCs), monocytes, and neutrophils after CDDO-Me treatment alone or after subsequent LPS exposure. Superoxide anion (O2) was measured to assess the effect of CDDO-Me pretreatment on subsequent LPS exposure. Treatment with CDDO-Me increased the gene expression of NQO1 (P = 0.04) and decreased the expression of HO-1 (P = 0.03) in PBMCs from patients with septic shock. Purified monocytes exhibited significant increases in the expression of NQO1 (P = 0.01) and GCLM (P = 0.003) after CDDO-Me treatment. Levels of other NRF2 target genes (HO-1 and FTL) remained similar to those of vehicle-treated cells. Peripheral blood mononuclear cells showed a trend toward increased IL-6 gene expression after CDDO-Me treatment, whereas purified monocytes showed a trend toward decreased IL-6. There was no discernible trend in the IL-6 expression subsequent to LPS treatment in either vehicle-treated or CDDO-Me-treated PBMCs and monocytes. Treatment with CDDO-Me significantly increased O2 production in PBMCs (P = 0.04). Although CDDO-Me pretreatment significantly attenuated O2 production to subsequent LPS exposure (P = 0.03), the

  16. The therapeutic response of CDDO-Me in the esophageal squamous cell carcinoma (ESCC) cells is mediated by CaMKIIα.

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    Wang, Yan-Yang; Zhou, Shun; Zhao, Ren; Hai, Ping; Zhe, Hong

    2016-01-01

    CDDO-Me has exhibited a potent anticancer effect in human esophageal squamous cell carcinoma (ESCC) cells in our previous study, but the molecular interactome remains elusive. We applied the approach of stable-isotope labeling by amino acids in cell culture (SILAC) to assess the proteomic responses of CDDO-Me treatment in human ESCC Ec109 cells. The data were subsequently validated using Western blot assay. The results of our study revealed that CDDO-Me increased the expression level of 543 protein molecules, but decreased the expression level of 709 protein molecules in Ec109 cells. Among these modulated protein molecules, calcium/calmodulin-dependent protein kinase type II subunit α (CaMKIIα) was highly expressed in all tested ESCC cell lines, whereas its expression levels were substantially lower in normal control cell line. Its silencing by small interfering RNA inhibited CDDO-Me induced apoptosis and autophagy in ESCC cells. Collectively, these data demonstrate that the therapeutic response of CDDO-Me in the human ESCC cells is mediated by CaMKIIα.

  17. 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.

  18. New Triterpenoid Saponins from the Rhizomes of Anemone amurensis

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    张岩; 黄晓君; 王磊; 王艳梅; 王英; 叶文才

    2012-01-01

    Five new oleanane-type saponins (1-5), together with three known ones (6-8), were isolated from the rhi- zomes of Anemone amurensis. Their structures were determined on the basis of spectroscopic analysis and chemical evidence. Compounds 2-4 are three novel sulfated oleanane-type triterpenoid glycosides.

  19. Inhibition of Lon protease by triterpenoids alters mitochondria and is associated to cell death in human cancer cells.

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    Gibellini, Lara; Pinti, Marcello; Bartolomeo, Regina; De Biasi, Sara; Cormio, Antonella; Musicco, Clara; Carnevale, Gianluca; Pecorini, Simone; Nasi, Milena; De Pol, Anto; Cossarizza, Andrea

    2015-09-22

    Mitochondrial Lon protease (Lon) regulates several mitochondrial functions, and is inhibited by the anticancer molecule triterpenoid 2-cyano-3, 12-dioxooleana-1,9(11)-dien-28-oic acid (CDDO), or by its C-28 methyl ester derivative (CDDO-Me). To analyze the mechanism of action of triterpenoids, we investigated intramitochondrial reactive oxygen species (ROS), mitochondrial membrane potential, mitochondrial mass, mitochondrial dynamics and morphology, and Lon proteolytic activity in RKO human colon cancer cells, in HepG2 hepatocarcinoma cells and in MCF7 breast carcinoma cells. We found that CDDO and CDDO-Me are potent stressors for mitochondria in cancer cells, rather than normal non-transformed cells. In particular, they: i) cause depolarization; ii) increase mitochondrial ROS, iii) alter mitochondrial morphology and proteins involved in mitochondrial dynamics; iv) affect the levels of Lon and those of aconitase and human transcription factor A, which are targets of Lon activity; v) increase level of protein carbonyls in mitochondria; vi) lead to intrinsic apoptosis. The overexpression of Lon can rescue cells from cell death, providing an additional evidence on the role of Lon in conditions of excessive stress load.

  20. Two New Triterpenoids from Lysimachia heterogenea Klatt and Evaluation of Their Cytotoxicity

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    Xin-Xin Zhou

    2011-09-01

    Full Text Available Two new 13,28-epoxy oleanane-type triterpenoids, namely heterogenoside E and F, were isolated from Lysimachia heterogenea Klatt, together with the eight known compounds: palmitic acid, β-stigmasterol, kaempferol, quercetin, hyperin, isorhamnetin, isorhamnetin-3-O-galactopyranoside and anagallisin C. Heterogenoside F possesses acetoxyl groups at the unusual C-21 and C-22 positions of its oleanane skeleton. The cytotoxic activities of anagallisin C, heterogenoside E and F were weak.

  1. New Bioactive Oleanane Type Compounds from Coriandrum sativum Linn.

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    Muhammad Iqbal

    2014-01-01

    Full Text Available Five (1–5 new bioactive oleanane type triterpenoids have been isolated from ethyl acetate soluble fraction of ethanolic extract of Coriandrum sativum Linn. of Umbelliferae family. Ethanolic extract of the whole plant was fractionated in organic solvents. Ethyl acetate fraction was subjected to column chromatography on HPLC RP-18 to get 1-oxo-11β,21β-dihydroxy-oleanane (1, 1-oxo-11β-hydroxy-21β-O-acetyloleanane (2, 1-oxo-11β-hydroxy-21β-O-angeloyloleanane (3, 1-oxo-11β-O-angeloyl-21β-O-acetyloleanane (4, and 1-oxo-11β,21β-O-dibenzoyloleanane (5. The structures were elucidated after analysis of spectroscopic data, UV, IR, NMR (1H, 13C, 1D, and 2D, and mass measurements. Suspension in water of crude ethyl acetate extract was employed to treat sheep with ringworm disease. All isolated compounds (1–5 displayed excellent activity in terms of inhibition zones, MICs, MBCs, and MFCs against both bacteria and fungi. Ethyl acetate extract showed excellent antiringworm activity in sheep.

  2. 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.

  3. Two New Triterpenoid Saponins from Gymnema sylvestre

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    Xu-Min Zhu; Ping Xie; Ying-Tong Di; Shu-Lin Peng; Li-Sheng Ding; Ming-Kui Wang

    2008-01-01

    Two new oleanane-type triterpenoid saponins, gymnemoside-W1 and W2, together with seven known compounds were isolated from the leaves of Gymnema sylvestre R. Br. By means of spectral and chemical analysis, the structures of the new compounds were elucidated as 16 β-hydroxyl olean-12-en-3-O-[β-D-glucopyranosyl (1→6)-β.D-glucopyranosyl]-28-O-β-D-glucopyranoside(1) and 16 β,21 β,28-trihydroxyl-olean-12-ene-3-O-glucoronopyranoside (2). The EtOHIH2O extracts of this plant were shown to be able to inhibit glucose absorption in rats.

  4. Two new triterpenoid saponins from Gymnema sylvestre.

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    Zhu, Xu-Min; Xie, Ping; Di, Ying-Tong; Peng, Shu-Lin; Ding, Li-Sheng; Wang, Ming-Kui

    2008-05-01

    Two new oleanane-type triterpenoid saponins, gymnemoside-W1 and W2, together with seven known compounds were isolated from the leaves of Gymnema sylvestre R. Br. By means of spectral and chemical analysis, the structures of the new compounds were elucidated as 16 beta-hydroxyl olean-12-en-3-O-[beta-D-glucopyranosyl (1-->6)-beta-D-glucopyranosyl]-28-O-beta-D-glucopyranoside(1) and 16 beta,21 beta,28-trihydroxyl-olean-12-ene-3-O-glucoronopyranoside (2). The EtOH/H(2)O extracts of this plant were shown to be able to inhibit glucose absorption in rats.

  5. Immunomodulatory triterpenoids from the oleogum resin of Boswellia carterii Birdwood.

    Science.gov (United States)

    Badria, Farid A; Mikhaeil, Botros R; Maatooq, Galal T; Amer, Mohamed M A

    2003-01-01

    The immunomodulatory bioassay-guided fractionation of the oleogum resin of frankincense (Boswellia carterii Birdwood) resulted in the isolation and identification of 9 compounds; palmitic acid and eight triterpenoids belonging to lupane, ursane, oleanane, and tirucallane skeleta were isolated form the resin. These triterpenoids are lupeol, beta-boswellic acid, 11-keto-beta-boswellic acid, acetyl beta-boswellic acid, acetyl 11-keto-beta-boswellic acid, acetyl-alpha-boswellic acid, 3-oxo-tirucallic acid, and 3-hydroxy-tirucallic acid. The structures of the isolated compounds were deduced based on spectroscopic evidences. The lymphocyte transformation assay of the isolated compounds proved that the total extract retained more activity than that of any of the purified compounds.

  6. Chemotaxonomic Approach to the Central Balkan Sedum Species Based on Distribution of Triterpenoids in Their Epicuticular Waxes.

    Science.gov (United States)

    Jovanović, Snežana Č; Zlatković, Bojan K; Stojanović, Gordana S

    2016-04-01

    Triterpenoid distribution in epicuticular waxes of 20 central Balkan Sedum L. species and four out-groups of genera: Hylotelephium H. Ohba, Crassula L., Echeveria DC., and Kalanchoe Adans. were investigated for chemotaxonomic purposes. Identification and quantification of wax triterpenoids were performed by GC/MS and GC-FID analyses. Distribution of identified triterpenoids (oleanane, lupane, and taraxerane series), as a pattern in statistical analysis, indicated very good agreement with phylogeny and systematics, except members of series Rupestria Berger, in which case the distribution of triterpenoids did not support known classification in a satisfactory manner. According to the obtained clustering, Kalanchoe is shown as similar to Sedum samples, while the other out-groups were clearly separated.

  7. Triterpenoids from Arctium lappa.

    Science.gov (United States)

    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.

  8. The molecular fossil record of oleanane and its relation to angiosperms

    Energy Technology Data Exchange (ETDEWEB)

    Moldowan, J.M.; Dahl, J.; Huizinga, J.; Fago, F.J.; Hickey, L.J.; Peakman, T.M.; Taylor, D.W. (Stanford University, Stanford, CA (United States). Dept. of Geological and Environmental Sciences)

    1994-08-05

    Oleanane has been reported in Upper Cretaceous and Tertiary source rocks and their related oils and has been suggested as a marker for flowering plants. Correspondence of oleanane concentrations relative to the ubiquitous microbial marker 17[alpha]-hopane with angiosperm diversification (Neocomian to Miocene) suggests that oleanane concentrations in migrated petroleum can be used to identify the maximum age of unknown or unavailable source rock. Rare occurrences of pre-Cretaceous oleanane suggest either that a separate lineage leads to the angiosperms well before the Early Cretaceous or that other plant groups have the rarely expressed ability to synthesize oleanane precursors. The authors also isolated 18[alpha]-oleanane from an extract of a Pennsylvanian coal ball, a calcium carbonate concretion containing well-preserved plant material from Illinois, USA. The coal ball represents localized input of vascular plants from a relatively narrow selection of species. Thus at least two samples show oleanane that predates the earliest accepted angiosperm fossil.

  9. The relationship of angiosperms and oleanane in petroleum through geologic time

    Energy Technology Data Exchange (ETDEWEB)

    Moldowan, J.M.; Dahl, J.E.; Huizinga, B.J.; Jacobson, S.R.; Taylor, D.W.

    1993-02-01

    The biological marker oleanane has been suggested as an indicator of angiosperm (flowering plant) input into source rocks and their derived oils. Parallels should therefore be evident between the angiosperm fossil record and oleanane occurrence and abundance. A global selection of more than 50 core samples from marine rocks of different ages and from different locations was quantitatively analyzed for oleanane to determine its abundance over geologic time relative to the bacterial marker hopane. Oleanane was recognized using Metastable Reaction Monitoring (MRM) GC-MS. A parallel was observed between the oleanane/hopane ratio and angiosperm diversity in the fossil record through time. The first fossil evidence of angiosperms is during the Early Cretaceous with radiation during the Late Cretaceous and Tertiary. Occurrences of oleanane are confirmed throughout the Cretaceous system. Early-to-middle Cretaceous (Berriasian-Cenomanian) occurrences are sporadic and oleanan/hopane ratios are less than 0.07. Late Cretaceous (Turonian-Maastrichtian) oleanane/hopane ratios range up to 0.15 with higher ratios in many Tertiary samples. It appears that oleanane/hopane ratios of oils can restrict the age of their unavailable or unknown source rocks. High ratios indicate Tertiary age and lower ratios can indicate Cretaceous or Tertiary age, depending on depositional environment. While these data do not rule out pre-Cretaceous oleanane, preliminary data show that oleanane/hopane ratios for Jurassic and older rock extracts are typically below our detection limits (<0.03). While oleanane precursors are abundant in angiosperms, they also occur, rarely, in other modern plant groups. We identified oleanane in low abundances in three Early Cretaceous fossil benettitialeans, an extinct plant group (Late Triassic to Late Cretaceous) thought to be related to angiosperms. These findings suggest that oleanane could be present in low abundance in some pre-Cretaceous rocks and oils.

  10. Novel triterpenoids from the aerial roots of Ficus microcarpa.

    Science.gov (United States)

    Chiang, Yi-Ming; Kuo, Yueh-Hsiung

    2002-11-01

    Three novel triterpenoids, 3beta-acetoxy-11alpha-hydroxy-11(12-->13)abeooleanan-12-al (1), 3beta-hydroxy-20-oxo-29(20-->19)abeolupane (2), and 29,30-dinor-3beta-acetoxy-18,19-dioxo-18,19-secolupane (3), and the known 4, 5a, and 5b were isolated from the aerial roots of Ficus microcarpa. Their structures were elucidated on the basis of 2D NMR and X-ray diffraction experiments. Compound 1, derived from the oleanane skeleton, has an unusual five-membered C ring. Compounds 2 and 3, derived from the lupane skeleton, have unique skeletons that may arise from the same biogenetic pathway.

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

    Directory of Open Access Journals (Sweden)

    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.

  12. Triterpenoid saponins from Argania spinosa.

    Science.gov (United States)

    Charrouf, Z; Wieruszeski, J M; Fkih-Tetouani, S; Leroy, Y; Charrouf, M; Fournet, B

    1992-06-01

    Five new oleanane saponins named arganine A, B, D, E and F and two known saponins: arganine C and mi-saponin A were isolated from the kernel of Argania spinosa. The structures of these saponins were elucidated by using 1H NMR, 1H-1H COSY NMR, 13C NMR, FAB mass spectrometry and chemical evidence.

  13. Isolation of Nematicidal Triterpenoid Saponins from Pulsatilla koreana Root and Their Activities against Meloidogyne incognita

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    Byung Soo Han

    2013-05-01

    Full Text Available Pulsatilla koreana, a species endemic to Korea, is an important herb used in traditional medicine to treat amoebic dysentery and malaria. In the present study, 23 oleanane-type triterpenoid saponins 1–23 and eight lupane-type triterpenoid saponins 24–31 were isolated from the roots of P. koreana. Their structures were elucidated on the basis of spectroscopic data. The methanol extract and isolated compounds were next assessed for nematicidal activity against the root-knot nematode (Meloidogyne incognita. The methanol extract showed strong nematicidal activity after 48 h, with a LC50 value of 92.8 μg/mL. Compounds 2, 5, 9, 20, and 21 showed significant effects, with LC50 values ranging from 70.1 to 94.7 μg/mL after 48 h. These results suggest that triterpenoid saponins from P. koreana should be explored as potential natural nematicides for developing new agents to control root-knot nematode disease

  14. Triterpenoids from Garcinia rigida

    Directory of Open Access Journals (Sweden)

    Berna Elya

    2011-01-01

    Full Text Available The leaves of Garcinia rigida afforded six triterpenoid compounds, friedelin (1, lanosta-8,25-en-3 b -ol (2, stigmasterol (3, lupeol (4, 3 b -hydroxy-20(29-en-lupan-30-al (5 and 3 b -hydroxy-20(29-en-lupan-30-ol (6. The structures of 1-6 were elucidated by IR, MS, NMR spectroscopies and comparison of their spectroscopic data with those reported in the literatures. Compound 6 showed toxicity to Artemia salina in brine shrimp lethality test (BLST with LC 50 27.72 µg/mL.

  15. Antidiabetic activity of a triterpenoid saponin isolated from Momordica cymbalaria Fenzl.

    Science.gov (United States)

    Koneri, Raju Balwanth; Samaddar, Suman; Ramaiah, Channakeshava Thimmasandra

    2014-01-01

    Glucose uptake by isolated diaphragms of both diabetic, following streptozotocin administration, and non-diabetic animals increased in presence of an oleanane-type triterpenoid saponin isolated from the roots of M. cymbalaria. Insulin release was augmented by the presence of the saponin of M. cymbalaria (1 mg/mL) in rat insulinoma cell line (RIN-5F) preexposed to adrenaline (5 microM) and nifedipine (50 microM). Pancreatic histology also indicated considerable quantitative increase in beta-cells (75%) when treated with the saponin. The results suggest that the saponin of M. cymbalaria possesses potential antidiabetic activity with respect to insulin secretion, which may be attributed to modulation of calcium channel, and beta-cell rejuvenation.

  16. 21beta-Hydroxy-oleanane-type triterpenes from Hippocratea excelsa.

    Science.gov (United States)

    Cáceres-Castillo, David; Mena-Rejón, Gonzalo J; Cedillo-Rivera, Roberto; Quijano, Leovigildo

    2008-02-01

    Stem bark of Hippocratea excelsa afforded six pentacyclic triterpenes, five oleanane and one ursane types. They were identified as 11beta,21beta-dihydroxy-olean-12-ene-3-one (2), 3alpha,11alpha,21beta-trihydroxy-olean-12-ene (3), 3alpha,21beta-dihydroxy-11alpha-methoxy-olean-12-ene (4), 3alpha,21beta-dihydroxy-olean-9(11),12-diene (5), 3alpha,21beta-dihydroxy-olean-12-ene (6) and 3alpha,21beta-dihydroxy-11alpha-methoxy-urs-12-ene, isolated as its diacetate derivative (7), as well as 3alpha,21beta-dihydroxy-olean-12-ene (1) previously isolated from the root bark. The known alpha- and beta-amyrin, oleanoic and ursolic acids, trans-polyisoprene, and the ubiquitous beta-sitosterol were also isolated. Structures were elucidated on the basis of spectroscopic analyses, including homo- and heteronuclear correlation NMR experiments (COSY, ROESY, HSQC and HMBC) and comparison with literature data. The antigiardial activity of compounds 2-5 was not significant.

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

    Science.gov (United States)

    Wang, Yan-Yang; Yang, Yin-Xue; Zhao, Ren; Pan, Shu-Ting; Zhe, Hong; He, Zhi-Xu; Duan, Wei; Zhang, Xueji; Yang, Tianxin; Qiu, Jia-Xuan; Zhou, Shu-Feng

    2015-01-01

    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), cleaved caspase-9, and cleaved poly ADP ribose polymerase (PARP) levels but increased the expression level of Bcl-2-associated X (Bax). Furthermore, CDDO-Me induced autophagy in both Ec109 and KYSE70 cells via suppression of the phosphoinositide 3-kinase/protein kinase B/mammalian target of rapamycin (PI3K/Akt/mTOR) signaling pathway. There were interactions between the autophagic and apoptotic pathways in Ec109 and KYSE70 cells subject to CDDO-Me treatment. CDDO-Me also scavenged reactive oxygen species through activation of the nuclear factor (erythroid-derived 2)-related factor 2 (Nrf2) pathway in Ec109 and KYSE70 cells. CDDO-Me inhibited cell invasion, epithelial-mesenchymal transition, and stemness in Ec109 and KYSE70 cells. CDDO-Me significantly downregulated E-cadherin but upregulated Snail, Slug, and zinc finger E-box-binding homeobox 1 (TCF-8/ZEB1) in Ec109 and KYSE70 cells. CDDO-Me significantly decreased the expression of octamer-4, sex determining region Y-box 2 (Sox-2), Nanog, and B lymphoma Mo-MLV insertion region 1 homolog (Bmi-1), all markers of cancer cell stemness, in Ec109 and KYSE70 cells. Taken together, these results indicate that CDDO-Me is a promising anticancer agent

  18. New oleanan-type triterpene and cincholic acid glycosides from Peruvian "Uña de Gato" (Uncaria tomentosa).

    Science.gov (United States)

    Kitajima, Mariko; Hashimoto, Ken-Ichiro; Sandoval, Manuel; Aimi, Norio; Takayama, Hiromitsu

    2004-10-01

    A new oleanan-type triterpene and three new cincholic acid glycosides were isolated from Peruvian "Una de Gato" (Cat's claw, plant of origin: Uncaria tomentosa), a traditional herbal medicine in Peru. Their structures were determined by spectroscopic analysis.

  19. Oleanane-type triterpene saponins from Calendula stellata.

    Science.gov (United States)

    Lehbili, Meryem; Alabdul Magid, Abdulmagid; Kabouche, Ahmed; Voutquenne-Nazabadioko, Laurence; Abedini, Amin; Morjani, Hamid; Sarazin, Thomas; Gangloff, Sophie C; Kabouche, Zahia

    2017-09-04

    Five previously undescribed bisdesmosidic triterpenoid saponins named calendustellatosides A-E, along with fifteen known compounds were isolated from the 70% ethanol whole plant extract of Calendula stellata Cav. (Asteraceae). Their structures were determined by 1D- and 2D-NMR spectroscopy as well as high resolution mass spectrometry and acid hydrolysis. The saponins comprised oleanolic acid, echinocystic acid, morolic acid or mesembryanthemoidigenic acid as the aglycones and saccharide moieties at C-3 and C-28. Like most Calendula saponins, the sugar moiety linked at C-3 was either β-d-glucose or β-d-glucuronic acid which could be substituted at C-3 by a β-d-galactose and/or C-2 by a supplementary β-d-galactose or a β-d-glucose. The sugar moiety linked to C-28 was determined as β-d-glucose. The antibacterial evaluation of compounds 1-20 by bioautography on Staphylococcus aureus followed by the determination of MIC values of active compounds by serial dilution technique against 5 bacteria revealed that; calendustellatoside D was the most active against Enterococcus faecalis with an antibacterial effect comparable to antibiotics. The cytotoxic activities of isolated compounds were evaluated against fibrosarcoma cell line (HT1080) and human lung cancer cell line (A549). Calendustellatosides B and D exhibited a low cytotoxic activity against HT1080 cell line with IC50 values of 47 ± 0.6 and 39 ± 0.5 μM, respectively. Copyright © 2017 Elsevier Ltd. All rights reserved.

  20. New oleanene triterpenoid saponins from Madhuca longifolia.

    Science.gov (United States)

    Yoshikawa, K; Tanaka, M; Arihara, S; Pal, B C; Roy, S K; Matsumura, E; Katayama, S

    2000-12-01

    Four new oleanane-type triterpene glycosides, madlongisides A-D (1-4), were isolated from the seeds of Madhuca longifolia, and their structures were elucidated on the basis of extensive NMR experiments and chemical methods. Also obtained in this investigation were the known compounds mimusopside A, Mi-saponins A, B, and C, and 3-O-beta-D-glucopyranosyl protobassic acid.

  1. Triterpenoid glycosides from Bacopa monnieri.

    Science.gov (United States)

    Sivaramakrishna, Chillara; Rao, Chirravuri V; Trimurtulu, Golakoti; Vanisree, Mulabagal; Subbaraju, Gottumukkala V

    2005-12-01

    Two triterpenoid glycosides have been isolated along with 10 known saponins from Bacopa monnieri. Structures of the compounds have been elucidated as 3-O-[beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl] jujubogenin (1) and 3-O-[beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl] pseudojujubogenin (2) by high resolution NMR spectral data and chemical correlations. Further, the chemical compositions of bacosides A and B have been delineated.

  2. 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.

  3. Derivados oleananos e ursanos e sua importância na descoberta de novos fármacos com atividade antitumoral, anti-inflamatória e antioxidante Oleanane and ursane derivatives and their importance on the discovery of potential antitumour, antiinflammatory and antioxidant drugs

    Directory of Open Access Journals (Sweden)

    Luciana Dalla Vechia

    2009-01-01

    Full Text Available Oleanolic and ursolic acids are triterpenes that exist abundantly in the plant kingdom. They show antitumor activity and their cytotoxic activity was already evaluated against a broad range of cell lines. The inhibition of enzymes involved in the metabolism of DNA and the induction of apoptosis are known events that have been related to the antitumour activity of these triterpenes. The antiinflamatory and antioxidant activities also seem to play an important role in their antitumour activity. In this review, it is presented an overview of the importance of the potential antitumour, antiinflamatory and antioxidant activities of these triterpenoid derivatives. Also, we propose a structural-activity relationship to triterpenes containing oleanane or ursane skeleton and their cytotoxic activity.

  4. 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.

  5. Triterpenoidal glycosides from Justicia betonica.

    Science.gov (United States)

    Kanchanapoom, Tripetch; Noiarsa, Pawadee; Ruchirawat, Somsak; Kasai, Ryoji; Otsuka, Hideaki

    2004-09-01

    dFrom the aerial portion of Justicia betonica L., four triterpenoidal glycosides (justiciosides A-D) were isolated. Their structures were established through chemical and NMR spectroscopic analyses as olean-12-ene-1beta,3beta,11alpha,28-tetraol 28-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranoside, olean-12-ene-1beta,3beta,11alpha,28-tetraol 28-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranoside, 11alpha-methoxy-olean-12-ene-1beta,3beta,28-triol 28-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranoside, 11alpha-methoxy-olean-12-ene-1beta,3beta,28-triol 28-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranoside, respectively.

  6. Two new triterpenoids from Psidium guajava

    Institute of Scientific and Technical Information of China (English)

    Ji Cheng Shu; Jian Qun Liu; Gui Xin Chou; Zheng Tao Wang

    2012-01-01

    Two new triterpenoids,named as 2α,3β,23-trlhydroxylurs-12,20(30)-dien-28-oic acid β-D-glucopyranoside (1),and 2α,3β,6β,20β3,23,30-hexahydroxyurs-12-en-28-oic acid (2),together with four known triterpenoids were isolated from the leaves of Psidium guajava L.Their structures were elucidated on the basis of mass and spectral evidence.

  7. 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.

  8. 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

  9. A new triterpenoid saponin from Gymnema sylvestre.

    Science.gov (United States)

    Zhang, Man-Qi; Liu, Yue; Xie, Sheng-Xu; Xu, Tun-Hai; Liu, Tong-Hua; Xu, Ya-Juan; Xu, Dong-Ming

    2012-01-01

    Besides four known compounds, a new triterpenoid saponin was isolated from the stems of Gymnema sylvestre. The structure of the new triterpenoid saponin was established as 3β,16β,22α-trihydroxy-olean-12-ene 3-O-β-D-xylopyranosyl-(1 → 6)-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranoside (1) on the basis of 1D and 2D NMR techniques, including COSY, HMBC, HMQC, and NOESY correlations. Four known compounds 2, 3, 4, and 5 were identified on the basis of spectroscopic data.

  10. Six new ursane- and oleanane-type triterpenes from the aerial roots of Ficus microcarpa.

    Science.gov (United States)

    Kuo, Y H; Chiang, Y M

    2000-05-01

    Four new ursane-type triterpenes, 3beta-acetoxy-11alpha-methoxy-12-ursene (1), 3beta-acetoxy-11alpha-ethoxy-12-ursene (2), 3beta-acetoxy-11alpha-hydroperoxy-12-ursene (3), 3beta-hydroxy-11alpha-hydroperoxy-12-ursene (4), and two new oleanane-type triterpenes, 3beta-acetoxy-11alpha-ethoxy-12-oleanene (5), 3beta-acetoxy-111alpha-hydroperoxy-12-oleanene (6), together with 3beta-acetoxy-11alpha-hydroxy-12-ursene (7), 3beta,11alpha-diacetoxy-12-ursene (8), 3beta-acetoxy-11alpha-hydroxy-12-oleanene (9), were isolated from the aerial roots of Ficus microcarpa L. f. Their structures were elucidated by spectroscopic and chemical methods.

  11. Saponins with highly hydroxylated oleanane-type aglycones from Silphium asteriscus L.

    Science.gov (United States)

    Masullo, Milena; Calabria, Lalita; Gallotta, Dario; Pizza, Cosimo; Piacente, Sonia

    2014-01-01

    Silphium asteriscus L., commonly known as starry rosinweed, is a plant found in prairies, glades, woodlands and savannas of the southeastern United States. The phytochemical investigation of the methanolic extract of S. asteriscus leaves led to the isolation of eighteen saponins with highly hydroxylated oleanane-type aglycones never reported before. Their structures were elucidated by extensive spectroscopic methods including 1D- ((1)H and (13)C) and 2D-NMR (DQF-COSY, HSQC, HMBC, TOCSY and ROESY) experiments as well as ESIMS analysis. The antiproliferative activity of the isolated compounds was evaluated against three cancer cell lines including Hela (human epitheloid cervix carcinoma), Jurkat cells (leukaemic T-cell line) and DLD-1 (colorectal adenocarcinoma). Compounds 1, 5 and 17 displayed weak activity with IC50 values ranging from 50 to 75 μM.

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

    Directory of Open Access Journals (Sweden)

    Syed Adnan Ali Shah

    2014-07-01

    Full Text Available 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.

  13. Pentacyclic triterpenoid ketones in peat from Gannan Marsh, China

    Institute of Scientific and Technical Information of China (English)

    2001-01-01

    Abundant terrigenous triterpenoid ketones and a series of hopanoid ketones were detected in a peat sample from the recent Gannan Marsh. The identifieations of pentacyclic triterpenoid ketones are discussed in detail. Based on the compositional features of pentacyclic triterpenoid ketones in the sample, it is proposed that terrigenous triterpenoid kentones originate directly from organisms or are diagenetic oxidation products of their alcohols, and hopanoid ketones are formed from hopanoids (e.g. hopanoid alcohols and hopenes) by chemical and biochemical processes. These data provide evidence for the applied studies of pentacyclic triterpenoid ketones as biomarker compounds.``

  14. A new triterpenoid saponin from Clematis ganpiniana

    Institute of Scientific and Technical Information of China (English)

    Feng Sun; Qing He; Pei Gen Xiao; Yi Yu Cheng

    2007-01-01

    A new triterpenoid saponin, named clematiganoside A (1), was isolated from the whole plant of Clematis ganpiniana. Its structure was elucidated on the basis of 1D, 2D NMR, TOF-MS and ESI-MS techniques, and physicochemical properties.

  15. A new triterpenoid saponin from Bacopa monniera

    Institute of Scientific and Technical Information of China (English)

    Yun Zhou; De Yun Kong; Ling Peng; Wei Dong Zhang

    2009-01-01

    A new triterpenoid saponin,bacopaside Ⅸ,was isolated from the whole plant of Bacopa monniera (L.) Wettst.and its structure was elucidated as 3-0-{β-d-glucopyranosyl(1 → 4)[α-1-arabinofuranosyl-(1 → 2)]-β-d-glucop-yranosyl}-20-O-α-1-axabinopyranosyljujubogenin by spectroscopic methods and some chemical transformations.

  16. Diterpenoids and triterpenoids from Euphorbia retusa.

    Science.gov (United States)

    Haba, Hamada; Lavaud, Catherine; Magid, Abdulmagid Alabdul; Benkhaled, Mohammed

    2009-07-01

    Six new ent-abietane lactones (1-6), three new esterified tetracyclic triterpenes (7-9), and seven known diterpenoids and triterpenoids were isolated from the roots of Euphorbia retusa. Their structures were elucidated by means of spectroscopic studies including 1D and 2D NMR, mass spectrometry, chemical transformation, and comparison with literature data.

  17. 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.

  18. 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)

  19. A New Triterpenoid from Teucrium viscidum

    Directory of Open Access Journals (Sweden)

    Yonghui Zhang

    2013-01-01

    Full Text Available A new ursane-type triterpenoid, 3β-hydroxy-urs-30-p-Z-hydroxycinnamoyloxy-12-en-28-oic-acid (1, together with three known triterpenoids, 3β-hydroxy-urs-30-p-E-hydroxycinnamoyloxy-12-en-28-oic-acid (2, 2α,3β,19α-trihydroxy-urs-12-en-28-oic-acid (3, and ursolic acid (4, four known lignans, pinoresinol (5, 9α-hydroxypinoresinol (6, (+-medioresinol (7, and (+-kobusin (8, and two steroids, β-sitosterol (9, and daucosterol (10, were isolated from the whole parts of Teucrium viscidum. Their structures were established by a combination of spectroscopic data analysis, besides comparison with literature data. Compounds 1–4 were evaluated for their inhibitory activities against 11β-hydroxysteroid dehydrogenase 1 (11β-HSD1.

  20. Triterpenoid glycosides from bark of Meliosma lanceolata.

    Science.gov (United States)

    Abe, F; Yamauchi, T; Shibuya, H; Kitagawa, I

    1996-06-01

    From the bark of Meliosma lanceolate, nine triterpenoid glycosides including the 28-O-beta-D-glucopyranosyl ester of bayogenin-3-O-beta-D-glucuronopyranoside, its 4'-O-beta-D-galactopyranoside and 4'-O-alpha-L-arabinopyranoside were isolated and the structures characterized along with that of 28-O-beta-D-glucopyranosyl-bayogenin-3-O-beta-D-4'-anhydro-4', 5'-didehydroglucuronopyranoside. Bisdesmosidic triosides of hederagenin were obtained as minor components.

  1. A new cucurbitane triterpenoid from Momordica charantia

    Institute of Scientific and Technical Information of China (English)

    2007-01-01

    One new cucurbitane-type triterpenoid saponin, 5β,19-epoxycucurbita-6,23-diene-3β,19,25-triol-3-O-β-D-allopyranoside (1),named momordicoside P was isolated from the fresh fruits ofMomordica charantia. The structure of the saponin was elucidated by spectral methods, including 2D-NMR spectra.(C) 2007 Yu Ying Zhao. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  2. Oleanane triterpenes as protein tyrosine phosphatase 1B (PTP1B) inhibitors from Camellia japonica.

    Science.gov (United States)

    Uddin, Mohammad Nasir; Sharma, Govinda; Yang, Jun-Li; Choi, Hong Seok; Lim, Seong-Il; Kang, Keon Wook; Oh, Won Keun

    2014-07-01

    Protein tyrosine phosphatase 1B (PTP1B) plays a key role in metabolic signaling, thereby making it an exciting drug target for type 2 diabetes and obesity. Besides, there is substantial evidence that shows its overexpression is involved in breast cancer, which suggests that selective PTP1B inhibition might be effective in breast cancer treatment. As part of our continuous research on PTP1B inhibitors from medicinal plants, four oleanane-type triterpenes were isolated from an EtOAc-soluble extract of fruit peels of Camellia japonica (Theaceae), together with 6 previously known compounds of this class. Their structures were determined on the basis of spectroscopic data analysis (UV, IR, (1)H and (13)CNMR, HMBC, HSQC, NOESY, and MS). All isolates were evaluated for their inhibitory effects on PTP1B, as well as their cytotoxic effects against human breast cancer cell lines MCF7, MCF7/ADR, and MDA-MB-231. Several compounds with OH-3 or/and COOH-28 functionalities showed strong PTP1B inhibitory activity (IC50 values ranging from 3.77±0.11 to 6.40±0.81 μM) as well as significant cytotoxicity (IC50 values ranging from 0.51±0.05 to 13.55±1.44 μM). Copyright © 2014 Elsevier Ltd. All rights reserved.

  3. Optimization of Cultivating Conditions for Triterpenoids Production from Antrodia cinnmomea.

    Science.gov (United States)

    He, Yuan-Chuan; He, Kai-Ze; Pu, Qiang; Li, Jing; Zhao, Zong-Jie

    2012-12-01

    The submerged cultivating conditions for triterpenoids production from Antrodia cinnamomea were optimized using uniform design method and the one-factor-at-a-time method was adopted to investigate the effect of plants oils and glucose supply on triterpenoids production and mycelia growth. Corn starch and culturing time were identified as more significant variables for triterpenoids production. The optimal conditions for triterpenoids production was 20.0 g/L corn starch, 20.0 g/L wheat bran, 1.85 g/L MgSO4, initial pH 3 and 16 days of cultivation. In addition, investigation of plant oils and glucose supply showed that 0.3 % (v/v) olive oil supply at the beginning of fermentation stimulated mycelia growth and significantly increased triterpenoids production; 0.2 % (w/v) glucose supplement at 10th day enhanced production of triterpenoids with slight effect on biomass, which is reported for the first time. The triterpenoids production experimentally obtained under the optimal conditions was 7.23 % (w/w). The uniform design method may be used to optimize many environmental and genetic factors such as temperature and agitation that can also affect the triterpenoids production from A. cinnamomea.

  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. Chemodiversity of ursane- and oleanane-type triterpenes in Amazonian Burseraceae oleoresins.

    Science.gov (United States)

    Rüdiger, André L; Veiga-Junior, Valdir F

    2013-06-01

    The oleoresins exuded from species of the Burseraceae family present high potential due to their biological and pharmacological properties. The evaluation of the chemodiversity of the oleoresins of 23 Amazonian species of Burseraceae provided a profile of the principal constituents, viz., the ursane-type triterpenes α-amyrin (1), α-amyrenone (3), and brein (5) and the oleanane-type triterpenes β-amyrin (2), β-amyrenone (4), and maniladiol (6), and allowed to determine which of these species have the highest biotechnological potential and which ones are rich in other, potentially new, triterpenes or volatile compounds of interest for the cosmetics industry. The oleoresin compositions obtained by GC-FID and GC/MS analyses were submitted to principal component analysis (PCA) and hierarchical clustering on principal components (HCPC), which divided the 23 samples in five clusters. Protium giganteum and Trattinnickia peruviana, constituting the first cluster, presented high oleoresin contents of 3 and 4 (28.8 and 16.3% on average, resp.). The seven species of Burseraceae composing the second cluster were potential producers of new triterpenes and volatile compounds. Dacryodes hopkinsii and five Protium species (third cluster) presented average contents for all the triterpenes analyzed. The highest contents of 5 and 6 (averages of 3.9 and 5.4%, resp.) were observed in P. heptaphyllum ssp. ullei and T. glaziovii (fourth cluster). Finally, the six Protium species forming the fifth cluster showed high contents of 1 and 2 (48.0 and 19.9% on average, resp.). Moreover, this study allowed the description of the triterpene composition of 13 not previously investigated species. Copyright © 2013 Verlag Helvetica Chimica Acta AG, Zürich.

  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 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.

  8. A triterpenoid saponin from Albizia julibrissin.

    Science.gov (United States)

    Zou, K; Zhao, Y Y; Tu, G Z; Guo, D A; Zhang, R Y; Zheng, J H

    1999-01-01

    A triterpenoid saponin (1) was obtained from the stem barks of Albizia julibrissin Durazz. Its structure was elucidated as 3-O-[beta-D-xylopyranosyl-(1 --> 2)-alpha-L-arabinopyranosyl-(1 --> 6)-beta-D-glucopyranosyl]-21-O-[(6S)-2-trans-2-hydroxymethyl-6-methyl-6-O-beta-D-quinovopyranosyl-2, 7-octadienoyl]-16-deoxy-acacic acid 28-O-beta-D-glucopyranosyl-(1 --> 3)-[alpha-L-arabinofuranosyl-(1 --> 4)]-alpha-L-rhamnopyranosyl-(1 --> 2)-beta-D-glucopyranosyl ester (1), named as Julibroside J26, based on the chemical and spectral methods.

  9. Three Novel Triterpenoids from Taraxacum officinale Roots

    Directory of Open Access Journals (Sweden)

    Takashi Kikuchi

    2016-08-01

    Full Text Available Three novel lupane-, bauerane-, and euphane-type triterpenoids (1–3, in addition to seven known triterpenoids (4–10—18β,19β-epoxy-21β-hydroxylupan-3β-yl acetate (4, 21-oxolup-18-en-3β-yl acetate (5, betulin (6, officinatrione (7, 11α-methoxyolean-12-en-3-one (8, eupha-7,24-dien-3-one (9, and 24-oxoeupha-7,24-dien-3β-yl acetate (10—were isolated from the roots of Taraxacum officinale. Their structures were elucidated on the basis of spectroscopic analyses using 1D and 2D-NMR spectra and electron ionization mass spectrometry (EIMS. The effects of compounds 1–10 on the production of nitric oxide (NO in lipopolysaccharide (LPS-activated mouse peritoneal macrophages were evaluated. Compounds 4, 6, and 10 exhibited similar NO inhibitory activities to NG-monomethyl-l-arginine acetate (l-NMMA. These compounds did not exhibit cytotoxicity at an effective concentration. The results of present study suggest that compounds 4, 6, and 10 have potential as anti-inflammatory disease agents.

  10. Three Novel Triterpenoids from Taraxacum officinale Roots.

    Science.gov (United States)

    Kikuchi, Takashi; Tanaka, Ayaka; Uriuda, Mayu; Yamada, Takeshi; Tanaka, Reiko

    2016-08-27

    Three novel lupane-, bauerane-, and euphane-type triterpenoids (1-3), in addition to seven known triterpenoids (4-10)-18β,19β-epoxy-21β-hydroxylupan-3β-yl acetate (4), 21-oxolup-18-en-3β-yl acetate (5), betulin (6), officinatrione (7), 11α-methoxyolean-12-en-3-one (8), eupha-7,24-dien-3-one (9), and 24-oxoeupha-7,24-dien-3β-yl acetate (10)-were isolated from the roots of Taraxacum officinale. Their structures were elucidated on the basis of spectroscopic analyses using 1D and 2D-NMR spectra and electron ionization mass spectrometry (EIMS). The effects of compounds 1-10 on the production of nitric oxide (NO) in lipopolysaccharide (LPS)-activated mouse peritoneal macrophages were evaluated. Compounds 4, 6, and 10 exhibited similar NO inhibitory activities to N(G)-monomethyl-l-arginine acetate (l-NMMA). These compounds did not exhibit cytotoxicity at an effective concentration. The results of present study suggest that compounds 4, 6, and 10 have potential as anti-inflammatory disease agents.

  11. Triterpenoids of Marine Origin as Anti-Cancer Agents

    Directory of Open Access Journals (Sweden)

    Yong-Xin Li

    2013-07-01

    Full Text Available Triterpenoids are the most abundant secondary metabolites present in marine organisms, such as marine sponges, sea cucumbers, marine algae and marine-derived fungi. A large number of triterpenoids are known to exhibit cytotoxicity against a variety of tumor cells, as well as anticancer efficacy in preclinical animal models. In this review efforts have been taken to review the structural features and the potential use of triterpenoids of marine origin to be used in the pharmaceutical industry as potential anti-cancer drug leads.

  12. Complete protection against aflatoxin B(1)-induced liver cancer with a triterpenoid: DNA adduct dosimetry, molecular signature, and genotoxicity threshold.

    Science.gov (United States)

    Johnson, Natalie M; Egner, Patricia A; Baxter, Victoria K; Sporn, Michael B; Wible, Ryan S; Sutter, Thomas R; Groopman, John D; Kensler, Thomas W; Roebuck, Bill D

    2014-07-01

    In experimental animals and humans, aflatoxin B1 (AFB1) is a potent hepatic toxin and carcinogen. The synthetic oleanane triterpenoid 1-[2-cyano-3-,12-dioxooleana-1,9(11)-dien-28-oyl]imidazole (CDDO-Im), a powerful activator of Keap1-Nrf2 signaling, protects against AFB1-induced toxicity and preneoplastic lesion formation (GST-P-positive foci). This study assessed and mechanistically characterized the chemoprotective efficacy of CDDO-Im against AFB1-induced hepatocellular carcinoma (HCC). A lifetime cancer bioassay was undertaken in F344 rats dosed with AFB1 (200 μg/kg rat/day) for four weeks and receiving either vehicle or CDDO-Im (three times weekly), one week before and throughout the exposure period. Weekly, 24-hour urine samples were collected for analysis of AFB1 metabolites. In a subset of rats, livers were analyzed for GST-P foci. The comparative response of a toxicogenomic RNA expression signature for AFB1 was examined. CDDO-Im completely protected (0/20) against AFB1-induced liver cancer compared with a 96% incidence (22/23) observed in the AFB1 group. With CDDO-Im treatment, integrated level of urinary AFB1-N(7)-guanine was significantly reduced (66%) and aflatoxin-N-acetylcysteine, a detoxication product, was consistently elevated (300%) after the first AFB1 dose. In AFB1-treated rats, the hepatic burden of GST-P-positive foci increased substantially (0%-13.8%) over the four weeks, but was largely absent with CDDO-Im intervention. The toxicogenomic RNA expression signature characteristic of AFB1 was absent in the AFB1 + CDDO-Im-treated rats. The remarkable efficacy of CDDO-Im as an anticarcinogen is established even in the face of a significant aflatoxin adduct burden. Consequently, the absence of cancer requires a concept of a threshold for DNA damage for cancer development.

  13. Triterpenoids from Roots and Stems of Kadsura coccinea.

    Science.gov (United States)

    Lian-Niang, L; Hong, X

    1986-12-01

    24-Methylenecycloartenone ( 1), kadsuric acid ( 2) and a new triterpenoid acid named coccinic acid ( 3A) were isolated from the ether soluble fraction of the dried roots and stems of KADSURA COCCINEA.

  14. A new triterpenoid saponin from Albizia julibrissin Durazz.

    Science.gov (United States)

    Xu, Tun-Hai; Li, Hai-Tao; Xu, Ya-Juan; Zhao, Hong-Feng; Xie, Sheng-Xu; Han, Dong; Si, Yun-Shan; Li, Yu; Niu, Jian-Zhao; Xu, Dong-Ming

    2008-01-01

    A new triterpenoid, saponin hehuanoside A, was isolated together with the known triterpenoid saponins 2, 3, and 4 from the stem bark of Albizia julibrissin. With the help of chemical and spectral analyzes (IR, MS, 1D-NMR, and 2D-NMR), the structure of the new triterpenoid saponin was elucidated as 21-O-[(6S)-2-trans-2,6-dimethyl-6-O-beta-d-quinovopyranosyl-2,7-octadienoyl]-3-O-beta-d-xylopyranosyl-(1 --> 2)-beta-d-fucopyranosyl-(1 --> 6)-beta-d-2-deoxy-2-acetamidoglucopyrasyl acacic acid 28-O-alpha-l-arabinofuranosyl-(1 --> 4)-[-beta-d-glucopyranosyl-(1 --> 3)]-alpha-l-rhamnopyranosyl-(1 --> 2)-beta-d-glucopyranosyl ester (1). Three known triterpenoid saponins 2-4 were identified on the basis of spectroscopic data.

  15. Two New Triterpenoids from Photinia serrulata

    Directory of Open Access Journals (Sweden)

    Yongxian Cheng

    2007-12-01

    Full Text Available Two new triterpenoids, 2α,3β,11α,13β-tetrahydroxy-12-ketooleanan-28-oic acid(1 and 3β-hydroxy-12-keto-9(11-ursen-28,13β-olide (2 were isolated from the leaves ofPhotinia serrulata. Their structures were identified by spectral methods. Compounds 1 and2 were assessed for cytotoxic activity against three human tumor cell lines (A-549, HCT-8,and BEL-7402, and they showed no cytotoxic effects at concentrations up to 5μg/mL.

  16. 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.

  17. Triterpenoidal constituents of the leaves of Carissa carandas.

    Science.gov (United States)

    Siddiqui, Bina S; Ghani, Usman; Ali, Syed Tahir; Usmani, Shahid Badar; Begum, Sabira

    2003-06-01

    Studies undertaken on the fresh leaves of Carissa carandas have led to the isolation of four pentacyclic triterpenoids (1-4) including one new constituent carissin (1) and two hitherto unreported compounds 2 and 3. The structure of the new triterpenoid has been elucidated as 3beta-hydroxy-27-E-feruloyloxyurs-12-en-28-oic acid. Compelete assignment of the protons of 2 has also been made based on 2D NMR studies.

  18. Kadcoccilactones A-J, triterpenoids from Kadsura coccinea.

    Science.gov (United States)

    Gao, Xue-Mei; Pu, Jian-Xin; Huang, Sheng-Xiong; Lu, Yang; Lou, Li-Guang; Li, Rong-Tao; Xiao, Wei-Lie; Chang, Ying; Sun, Han-Dong

    2008-07-01

    Ten new highly oxygenated triterpenoids, kadcoccilactones A-J (1-10), and two known triterpenoids, kadsuphilactone A and micrandilactone B, were isolated from the stems of the evergreen climbing plant Kadsura coccinea. The structures of the new compounds were elucidated by spectroscopic evidence, with that of 1 confirmed by single-crystal X-ray diffraction analysis. This is the first report on nortriterpenoids (2, 4-6, 8-10) from the genus Kadsura.

  19. Two new triterpenoids from the roots of Pinus densiflora.

    Science.gov (United States)

    Otaka, Junnosuke; Komatsu, Masabumi; Miyazaki, Yasumasa; Futamura, Yushi; Osada, Hiroyuki

    2017-03-01

    Chemical investigation of the roots of Pinus densiflora led to the isolation of two new triterpenoids, (24S)-3β-methoxy-24,25-epoxy-lanost-9(11)-ene (1) and 29-acetoxy-3α-methoxyserrat-14-en-21α-ol (2), together with three known serratene-type triterpenoids (3-5) and four known diterpenoids (6-9). Their structures were determined by spectroscopic analyses.

  20. The ancient CYP716 family is a major contributor to the diversification of eudicot triterpenoid biosynthesis

    Science.gov (United States)

    Miettinen, Karel; Pollier, Jacob; Buyst, Dieter; Arendt, Philipp; Csuk, René; Sommerwerk, Sven; Moses, Tessa; Mertens, Jan; Sonawane, Prashant D; Pauwels, Laurens; Aharoni, Asaph; Martins, José; Nelson, David R.; Goossens, Alain

    2017-01-01

    Triterpenoids are widespread bioactive plant defence compounds with potential use as pharmaceuticals, pesticides and other high-value products. Enzymes belonging to the cytochrome P450 family have an essential role in creating the immense structural diversity of triterpenoids across the plant kingdom. However, for many triterpenoid oxidation reactions, the corresponding enzyme remains unknown. Here we characterize CYP716 enzymes from different medicinal plant species by heterologous expression in engineered yeasts and report ten hitherto unreported triterpenoid oxidation activities, including a cyclization reaction, leading to a triterpenoid lactone. Kingdom-wide phylogenetic analysis of over 400 CYP716s from over 200 plant species reveals details of their evolution and suggests that in eudicots the CYP716s evolved specifically towards triterpenoid biosynthesis. Our findings underscore the great potential of CYP716s as a source for generating triterpenoid structural diversity and expand the toolbox available for synthetic biology programmes for sustainable production of bioactive plant triterpenoids. PMID:28165039

  1. [Triterpenoid sapogenins in the genus Grindelia].

    Science.gov (United States)

    Kreutzer, S; Schimmer, O; Waibel, R

    1990-08-01

    A saponin fraction has been isolated from the ethanolic extract of Grindeliae herba. The saponin fraction showed strong haemolytic activity. The saponins were detected after separation on TLC by their color reactions and Rf values as well as by their haemolytic activity on blood agar. After hydrolysis, the chemical reactions and Rf values of the sapogenins were described. The main sapogenin was isolated by preparative chromatography and its structure was elucidated by mass, 1H-NMR, 13C-NMR, IR, and UV spectra. The compound is a new natural triterpenoid sapogenin lactone and is named grindeliasapogenin D. Spectral evidence is presented to establish its structure as 2 beta,3 beta,16 alpha,23-tetrahydroxyoleanan-28,13 beta-olide. Two further sapogenins present in small amounts were identified chromatographically as oleanolic acid and bayogenin using authentic reference substances. The aerial parts of Grindelia robusta Nutt, and G. lanceolata Nutt. (Asteraceae) (as well as two commercial extracts) were also investigated with respect to their saponin fraction. The 3 sapogenins mentioned above were detected in all samples. The antibiotic potency of the crude drug is not associated with the saponin fraction but is at least partially due to the resin fraction.

  2. New bioactive triterpenoid from Oldenlandia cantonensis How

    Institute of Scientific and Technical Information of China (English)

    LAN Wenjian; LI Houjin

    2007-01-01

    A new pentacyclic triterpenoid,urs-12-en-29α-oic acid-3β-ol (1),was obtained from the ethanol extract of Chinese herb Oldenlandia cantonensis How.The structure was elucidated by spectroscopy methods,including nuclear magnetic resonance (NMR) (ID and 2D),infrared spectroscopy (IR),and mass spectrometry (MS).1 exhibited significant inhibitory activity against the human DNA topoisomerase Ⅰ (hTopo Ⅰ),the cancer cell lines BEL-7402 and MCG-803,with the IC50 values 12.0,6.5,and 8.0 μg/mL,respectively.The volatile oil,the fraction of petroleum ether:EtOAc = 20:1 (V/V) on Si gel chromatography,was also quantitatively analyzed by gas chromatography mass spectrometry (GC-MS).As a result,60 compounds were identified.Among them,the long chain aliphatics,terpenes and steroids,as the representative structure type,were found with percentages of 36.16%,6.42% and 9.28%,respectively.

  3. Diterpenoids and triterpenoids from Euphorbia guyoniana.

    Science.gov (United States)

    Haba, Hamada; Lavaud, Catherine; Harkat, Hassina; Alabdul Magid, Abdulmagid; Marcourt, Laurence; Benkhaled, Mohammed

    2007-05-01

    Two new compounds with tigliane and cycloartane skeletons: 4,12-dideoxy(4alpha)phorbol-13-hexadecanoate (1) and 24-methylenecycloartane-3,28-diol (2), respectively, in addition of four known diterpenoids and 13 triterpenoids: 3-benzoyloxy-5,15-diacetoxy-9,14-dioxojatropha-6(17),11-diene (4), ent-abieta-8(14),13(15)-dien-16,12-olide (5), ent-8alpha,14alpha-epoxyabieta-11,13(15)-dien-16,12-olide (6), ent-3-hydroxyatis-16(17)-ene-2,14-dione (7), 3beta-hydroxytaraxer-14-en-28-oic acid (8), beta-sitosteryl-3beta-glucopyranoside-6'-O-palmitate (9), multiflorenyl acetate (10), multiflorenyl palmitate (11), peplusol (12), 24-methylenecycloartanol (3), lanosterol (13), euferol (14), butyrospermol (15), cycloartenol (16), obtusifoliol (17), cycloeucalenol (18) and beta-sitosterol (19), were isolated from the roots of Euphorbia guyoniana. Their structures were established on the basis of physical and spectroscopic analysis, including 1D and 2D homo- and heteronuclear NMR experiments (COSY, HSQC, HMBC and NOESY) and by comparison with the literature data.

  4. The involvement of β-amyrin 28-oxidase (CYP716A52v2) in oleanane-type ginsenoside biosynthesis in Panax ginseng.

    Science.gov (United States)

    Han, Jung-Yeon; Kim, Min-Jun; Ban, Yong-Wook; Hwang, Hwan-Su; Choi, Yong-Eui

    2013-12-01

    Panax species are the most popular medicinal herbs. The root of these plants contains pharmacologically active triterpene saponins, also known as ginsenosides, compounds that are divided into dammarane- and oleanane-type triterpenes. Two CYP716A subfamily genes (CYP716A47 and CYP716A53v2) were recently characterized, encoding an enzyme catalyzing the hydroxylation of dammarane-type triterpenes in Panax ginseng. Herein, we report that one CYP716A subfamily gene (CYP716A52v2) isolated from P. ginseng encodes a β-amyrin 28-oxidase, which is suggested to modify β-amyrin into oleanolic acid, a precursor of an oleanane-type saponin (mainly ginsenoside Ro) in P. ginseng. The ectopic expression of both PNY1 and CYP716A52v2 in recombinant yeast resulted in erythrodiol and oleanolic acid production, respectively. In vitro enzymatic activity assays biochemically confirmed that CYP716A52v2 catalyzed the oxidation of β-amyrin to produce oleanolic acid, and the chemical structure of the oleanolic acid product was confirmed using gas chromatography-mass spectrometry (GC/MS). Transgenic P. ginseng plants were generated via Agrobacterium tumefaciens-mediated transformation: the overexpression of CYP716A52v2 greatly increased the content of oleanane-type ginsenoside (ginsenoside Ro), whereas RNA interference against CYP716A52v2 markedly reduced it. Furthermore, the levels of other dammarene-type ginsenosides were not affected in these transgenic lines. These results indicate that CYP716A52v2 is a β-amyrin 28-oxidase that plays a key role in the biosynthesis of oleanane-type triterpenes in P. ginseng.

  5. 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.

  6. Kadcotriones A-C: tricyclic triterpenoids from Kadsura coccinea.

    Science.gov (United States)

    Liang, Cheng-Qin; Shi, Yi-Ming; Li, Xing-Yao; Luo, Rong-Hua; Li, Yan; Zheng, Yong-Tang; Zhang, Hong-Bin; Xiao, Wei-Lie; Sun, Han-Dong

    2013-12-27

    Three new triterpenoids, kadcotriones A-C (1-3), together with the biogenetically related lanostane-type triterpenoid (4), were isolated from Kadsura coccinea. Compound 1 features a 12,14β-dimethyl 6/6/6-fused tricyclic skeleton, while 2 and 3 are characterized by a 6/6/5-ring system. Their structures were determined by NMR and electronic circular dichroism spectroscopic methods. Compounds 2 and 4 exhibited anti-HIV-1 activities with EC50 values of 30.29 and 54.81 μM, respectively.

  7. Triterpenoidal Saponins: Bioactive Secondary Metabolites from Zygophyllum coccineum

    Science.gov (United States)

    2011-01-22

    of the publishers only Planta Medica Journal of Medicinal Plant and Natural Product Research www.thieme.de/fz/plantamedica l www.thieme-connect.com...insecticidal activity of compounds 1, 3, 5, 6, and 9. Amin E et al. Triterpenoidal Saponins: Bioactive… Planta Med Letters Th is is a co py of th e...Amin E et al. Triterpenoidal Saponins: Bioactive… Planta Med Letters Th is is a co py of th e au th or ʼs pe rs on al re pr in t Th is is a co py of th

  8. Two New Oleanane-Type Saponins with Anti-Proliferative Activity from Camellia oleifera Abel. Seed Cake

    Directory of Open Access Journals (Sweden)

    Jian-Fa Zong

    2016-02-01

    Full Text Available Two new oleanane-type saponins, named oleiferasaponins C4 (1 and C5 (2, were isolated from Camellia oleifera Abel. seed cake residue. Their respective structures were identified as 16α-hydroxy-22α-O-angeloyl-23α-aldehyde-28-dihydroxymethylene-olean-12-ene-3β-O-[β-d-galacto-pyranosyl-(1→2]-[β-d-glucopyranosyl-(1→2-β-d-galactopyranosy-(1→3]-β-d-glucopyranosid-uronic acid methyl ester (1 and 16α-hydroxy-22α-O-angeloyl-23α-aldehyde-28-dihydroxy-methylene-olean-12-ene-3β-O-[β-d-galactopyranosyl-(1→2]-[β-d-galactopyranosyl-(1→3]-β-d-glucopyranosiduronic acid methyl ester (2 through 1D- and 2D-NMR, HR-ESI-MS, and GC-MS spectroscopic methods. The two compounds exhibited potent cytotoxic activities against five human tumor cell lines (BEL-7402, BGC-823, MCF-7, HL-60 and KB.

  9. Two New Triterpenoids from the Roots of Sanguisorba officinalis L.

    Institute of Scientific and Technical Information of China (English)

    Fan ZHANG; Tie-Jun FU; Shu-Lin PENG; Zhong-Rong LIU; Li-Sheng DING

    2005-01-01

    Two new triterpenoids, octanordammar- 1,11,13(17)-trien- 17-ol-3,16-dione (1) and lup- 12-en- 15α,19β-diol-3,11-dioxo-28-oic acid (4), as well as 13 known compounds were isolated from the roots of Sanguisorba officinalis L. (Rosaceae). Their structures were determined using spectroscopic methods.

  10. Triterpenoid glycosides from the leaves of Meliosma henryi.

    Science.gov (United States)

    Alabdul Magid, Abdulmagid; Morjani, Hamid; Harakat, Dominique; Madoulet, Claudie; Dumontet, Vincent; Lavaud, Catherine

    2015-01-01

    Seven triterpenoid glycosides, named meliosmosides A-G, were isolated from the leaves of Meliosma henryi Diels (Sabiaceae). Their structures were elucidated by different spectroscopic methods including 1D and 2D NMR experiments as well as HRESIMS analysis. Isolated compounds were evaluated for their cytotoxic activity against KB cell line.

  11. A new epidioxy-tetracyclic triterpenoid from Poria cocos Wolf.

    Science.gov (United States)

    Li, Shiping; Wang, Zhixin; Gu, Rui; Zhao, Yiwu; Huang, Wenzhe; Wang, Zhenzhong; Xiao, Wei

    2016-08-01

    A new epidioxy-tetracyclic triterpenoid, 3-(2-hydroxyacetoxy)-5α, 8α-peroxydehydrotumulosic acid (10), along with nine known compounds were isolated from Poria cocos Wolf (Polyporaceae). Their structures were determined by extensive spectroscopic analyses and comparison with literature data. The cytotoxicity of these compounds against human cancer cell lines MNK-45 was evaluated by MTT method.

  12. Fruit cuticular waxes as a source of biologically active triterpenoids.

    Science.gov (United States)

    Szakiel, Anna; Pączkowski, Cezary; Pensec, Flora; Bertsch, Christophe

    2012-06-01

    The health benefits associated with a diet rich in fruit and vegetables include reduction of the risk of chronic diseases such as cardiovascular disease, diabetes and cancer, that are becoming prevalent in the aging human population. Triterpenoids, polycyclic compounds derived from the linear hydrocarbon squalene, are widely distributed in edible and medicinal plants and are an integral part of the human diet. As an important group of phytochemicals that exert numerous biological effects and display various pharmacological activities, triterpenoids are being evaluated for use in new functional foods, drugs, cosmetics and healthcare products. Screening plant material in the search for triterpenoid-rich plant tissues has identified fruit peel and especially fruit cuticular waxes as promising and highly available sources. The chemical composition, abundance and biological activities of triterpenoids occurring in cuticular waxes of some economically important fruits, like apple, grape berry, olive, tomato and others, are described in this review. The need for environmentally valuable and potentially profitable technologies for the recovery, recycling and upgrading of residues from fruit processing is also discussed.

  13. Pentacyclic Triterpenoids from the Medicinal Herb, Centella asiatica (L. Urban

    Directory of Open Access Journals (Sweden)

    Ian A. Dubery

    2009-10-01

    Full Text Available Centella asiatica accumulates large quantities of pentacyclic triterpenoid saponins, collectively known as centelloids. These terpenoids include asiaticoside, centelloside, madecassoside, brahmoside, brahminoside, thankuniside, sceffoleoside, centellose, asiatic-, brahmic-, centellic- and madecassic acids. The triterpene saponins are common secondary plant metabolites and are synthesized via the isoprenoid pathway to produce a hydrophobic triterpenoid structure (aglycone containing a hydrophilic sugar chain (glycone. The biological activity of saponins has been attributed to these characteristics. In planta, the Centella triterpenoids can be regarded as phytoanticipins due to their antimicrobial activities and protective role against attempted pathogen infections. Preparations of C. asiatica are used in traditional and alternative medicine due to the wide spectrum of pharmacological activities associated with these secondary metabolites. Here, the biosynthesis of the centelloid triterpenoids is reviewed; the range of metabolites found in C. asiatica, together with their known biological activities and the chemotype variation in the production of these metabolites due to growth conditions are summarized. These plant-derived pharmacologically active compounds have complex structures, making chemical synthesis an economically uncompetitive option. Production of secondary metabolites by cultured cells provides a particularly important benefit to manipulate and improve the production of desired compounds; thus biotechnological approaches to increase the concentrations of the metabolites are discussed.

  14. 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.

  15. A New Isomalabaricane Triterpenoid from Sponge Jaspis sp.

    Institute of Scientific and Technical Information of China (English)

    Sheng An TANG; Zhi Wei DENG; Jun LI; Hong Zheng FU; Yue Hu PEI; Si ZHANG; Wen Han LIN

    2005-01-01

    From the marine sponge Jaspis sp., a new isomalabaricane triterpenoid 22, 23-dihydrostellettin D (1) was isolated, and its structure was established on the basis of IR, MS and extensive 2D NMR spectroscopic analysis. It is a unique skeleton compound rarely obtained from Chinese marine organisms.

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

    DEFF Research Database (Denmark)

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

    2016-01-01

    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...

  17. Triterpenoids as novel natural inhibitors of human cathepsin L.

    Science.gov (United States)

    Ramalho, Suelem D; De Sousa, Lorena R F; Nebo, Liliane; Maganhi, Stella H; Caracelli, Ignez; Zukerman-Schpector, Julio; Lima, Maria Inês S; Alves, Marcio F M; Da Silva, M Fátima das G F; Fernandes, João B; Vieira, Paulo C

    2014-09-01

    Cathepsins L (catL) and B play an important role in tumor progression and have been considered promising therapeutic targets in the development of novel anticancer agents. Using a bioactivity-guided fractionation, a series of triterpenoids was identified as a new class of competitive inhibitors towards cathepsin L with affinity values in micromolar range. Among the 14 compounds evaluated, the most promising were 3-epiursolic acid (3), 3-(hydroxyimino)oleanolic acid (9), and 3-(hydroxyimino)masticadienoic acid (13) with IC50 values of 6.5, 2.4, and 2.6 μM on catL, respectively. Most of the evaluated triterpenoids do not inhibit cathepsin B. Thus, the evaluated compounds exhibit a great potential to help in the design of new inhibitors with enhanced potency and affinity towards catL. Docking studies were performed in order to gain insight on the binding mode and SAR of these compounds.

  18. Lanostane- and cycloartane-type triterpenoids from Abies balsamea oleoresin

    Directory of Open Access Journals (Sweden)

    Serge Lavoie

    2013-07-01

    Full Text Available Phytochemical analysis of A. balsamea oleoresin led to the isolation of three new 3,4-seco-lanostane triterpenoids 1–3, one new cycloartane triterpenoid 4 along with fourteen known terpenoids. Structure determinations were based on extensive 1D/2D NMR, IR and MS spectroscopic analyses, and comparison with literature data. The isolated compounds were evaluated in vitro for their cytotoxicity against human cell lines (A549, DLD-1, WS1 and their antibacterial activity against E. coli and S. aureus. Abiesonic acid (6 exhibited weak cytotoxic activity against A549 (IC50 = 22 µM while compounds 1 and 4 were weakly active against S. aureus (MIC = 25 µM.

  19. 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.

  20. Bacoside A3--a triterpenoid saponin from Bacopa monniera.

    Science.gov (United States)

    Rastogi, S; Pal, R; KulshreshthaDK

    1994-05-01

    A new triterpenoid saponin, bacoside A3, a constituent of bacosides the saponin mixture of Bacopa monniera, was isolated and characterized. Its structure was established as 3-beta-[O-beta-D-glucopyranosyl(1-->3)-O- [alpha-L-arabinofuranosyl(1-->2) ]O-beta-D-glucopyranosyl)oxy]jujubogenin by chemical and spectral analyses. The cis-isomer of ebelin lactone was also obtained as one of the artefacts of the aglycone and its structure revised.

  1. Oxygenated lanostane-type triterpenoids from the fungus ganodermalucidum.

    Science.gov (United States)

    Akihisa, Toshihiro; Tagata, Masaaki; Ukiya, Motohiko; Tokuda, Harukuni; Suzuki, Takashi; Kimura, Yumiko

    2005-04-01

    Two new triterpenoids, 20(21)-dehydrolucidenic acid A (1) and methyl 20(21)-dehydrolucidenate A (2), and five new 20-hydroxylucidenic acids, 20-hydroxylucidenic acid D(2) (3), 20-hydroxylucidenic acid F (4), 20-hydroxylucidenic acid E(2) (5), 20-hydroxylucidenic acid N (6), and 20-hydroxylucidenic acid P (7), were isolated from the fruiting body of the fungus Ganoderma ludicum, and their structures were established on the basis of spectroscopic methods.

  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. Pigments of Staphylococcus aureus, a series of triterpenoid carotenoids.

    Science.gov (United States)

    Marshall, J H; Wilmoth, G J

    1981-01-01

    The pigments of Staphylococcus aureus were isolated and purified, and their chemical structures were determined. All of the 17 compounds identified were triterpenoid carotenoids possessing a C30 chain instead of the C40 carotenoid structure found in most other organisms. The main pigment, staphyloxanthin, was shown to be alpha-D-glucopyranosyl 1-O-(4,4'-diaponeurosporen-4-oate) 6-O-(12-methyltetradecanoate), in which glucose is esterified with both a triterpenoid carotenoid carboxylic acid and a C15 fatty acid. It is accompanied by isomers containing other hexoses and homologs containing C17 fatty acids. The carotenes 4,4'-diapophytoene, 4,4'-diapophytofluene, 4-4'-diapophytofluene, 4-4'-diapo-zeta-carotene, 4,4'-diapo-7,8,11,12-tetrahydrolycopene, and 4,4'-diaponeurosporene and the xanthophylls 4,4'-diaponeurosporenal, 4,4'-diaponeurosporenoic acid, and glucosyl diaponeurosporenoate were also identified, together with some of their isomers or breakdown products. The symmetrical 4,4'-diapo- structure was adopted for these triterpenoid carotenoids, but an alternative unsymmetrical 8'-apo-structure could not be excluded. PMID:7275936

  4. 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.

  5. Triterpenoids from Gymnema sylvestre and their pharmacological activities.

    Science.gov (United States)

    Fabio, Giovanni Di; Romanucci, Valeria; De Marco, Anna; Zarrelli, Armando

    2014-07-28

    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. Studies on the Constituents of Ficus microcarpa L.f. 1. Triterpenoids from the Leaves

    OpenAIRE

    Higa, Matsutake; Yogi, Seiichi; Hokama, Kozo; 比嘉, 松武; 与儀, 誠一; 外間, 宏三

    1987-01-01

    The following triterpenoids were isolated from the ethanol extracts of the leaves of Ficus microcarpa L.f., together with aliphatic compounds and steroids: lupenyl acetate, friedelin, glutinol, epifriedelinol, taraxerol and oleanolic acid. Two unknown pentacyclic triterpenoids were also isolated and their structures were discussed from spectroscopic evidences.

  7. Rational design of a β-glycosidase with high regiospecificity for triterpenoid tailoring.

    Science.gov (United States)

    Park, Sang Jin; Choi, Jung Min; Kyeong, Hyun-Ho; Kim, Song-Gun; Kim, Hak-Sung

    2015-03-23

    Triterpenoids with desired glycosylation patterns have attracted considerable attention as potential therapeutics for inflammatory diseases and various types of cancer. Sugar-hydrolyzing enzymes with high substrate specificity would be far more efficient than other methods for the synthesis of such specialty triterpenoids, but they are yet to be developed. Here we present a strategy to rationally design a β-glycosidase with high regiospecificity for triterpenoids. A β-glycosidase with broad substrate specificity was isolated, and its crystal structure was determined at 2.0 Å resolution. Based on the product profiles and substrate docking simulations, we modeled the substrate binding modes of the enzyme. From the model, the substrate binding cleft of the enzyme was redesigned in a manner that preferentially hydrolyzes glycans at specific glycosylation sites of triterpenoids. The designed mutants were shown to produce a variety of specialty triterpenoids with high purity.

  8. Two new cucurbitane triterpenoids from Momordica charantia L.

    Institute of Scientific and Technical Information of China (English)

    Jia Qing Cao; Yu Zhang; Jiong Mo Cui; Yu Qing Zhao

    2011-01-01

    Two new cucurbitane-type triterpenoids, (23E)-5 β,19-epoxycucurbita-6,23,25-triene-3β-ol (1) and (19R, 23E)-5β,19-epoxy-19-ethoxycucurbita-6,23-diene-3 β,25-diol (2), together with three known compounds, have been isolated from the fruit of Momordica charantia L. Their structures were determined on the basis of spectral analysis. Their cytotoxic activity was tested on 5 cancer cell lines, MCF-7, HepG2, Dul45, Colon205 and HL-60 by MTT assay. Compounds 1, 3 and 4 showed weak cytotoxicity.

  9. Lanostane triterpenoids from the inedible mushroom Fomitopsis spraguei.

    Science.gov (United States)

    Quang, Dang Ngoc; Arakawa, Yuuki; Hashimoto, Toshihiro; Asakawa, Yoshinori

    2005-07-01

    Investigation of the methanolic extract of the inedible mushroom Fomitopsis spraguei (Polyporaceae) led to the isolation of five lanostane-type triterpenoids (1-5): three new compounds named fomitopsins A-C (2-4), and two known compounds, quercinic acid C (1) and 3alpha-carboxyacetyl-12beta-hydroxyquercinic acid (5). Their structures were determined by 2D NMR, MS, IR, UV spectra, and X-ray crystallographic analyses. An X-ray crystal structure analysis of quercinic acid C (1) established its stereochemistry as 3R,12R-dihydroxy-24R-methyl-23-oxo-25S-lanost-8-en-26-oic acid.

  10. Lanostane-type triterpenoids from the roots of Kadsura coccinea.

    Science.gov (United States)

    Wang, Nan; Li, Zhanlin; Song, Dandan; Li, Wei; Fu, Hongwei; Koike, Kazuo; Pei, Yuehu; Jing, Yongkui; Hua, Huiming

    2008-06-01

    Seven new lanostane-type triterpenoids, seco-coccinic acids A-F (1- 6) and coccinilactone A (7), were isolated from the roots of Kadsura coccinea. Their structures were established on the basis of spectroscopic data analysis. The absolute configuration at C-24 of compound 5 was confirmed by the modified Mosher's method. The cell growth inhibitory effects of these compounds were determined in human leukemia HL-60 cells, and it was found that compounds 1, 2, 3, and 5 exhibited antiproliferative effects with GI 50 values ranging from 6.8 to 42.1 microM.

  11. Lactam Triterpenoids from the Bark of Toona sinensis

    Directory of Open Access Journals (Sweden)

    Qian-Qian Meng

    2016-10-01

    Full Text Available Abstract Three new limonoid-type triterpenoids, namely toonasins A–C (1–3 with a rare lactam E ring, along with six known compounds (4–9 were isolated from the barks of Toona sinensis. The structures of new compounds were elucidated by interpretation of spectroscopic data, and the relative configuration of compound 1 was further characterized by X-ray crystallographic analyses. The isolated compounds were evaluated for their cytotoxic activities against five human tumor cell lines (HL-60, SMMC-7721, A-549, MCF-7 and SW480, and compounds 3 and 5 showed weak cytotoxicities.

  12. Effects of captopril, telmisartan and bardoxolone methyl (CDDO-Me) in ischemia-reperfusion-induced acute kidney injury in rats: an experimental comparative study.

    Science.gov (United States)

    Kocak, Cengiz; Kocak, Fatma Emel; Akcilar, Raziye; Bayat, Zeynep; Aras, Bekir; Metineren, Mehmet Huseyin; Yucel, Mehmet; Simsek, Hasan

    2016-02-01

    Renal ischemia-reperfusion (IR) injury is one of the most common causes of acute kidney injury. This study investigated the effects of captopril (CAP), telmisartan (TEL) and bardoxolone methyl (BM) in animals with renal IR injury. Adult male Wistar-Albino rats were divided into six groups: control, vehicle, IR, IR with CAP, IR with TEL and IR with BM. Before IR was induced, drugs were administered by oral gavage. After a 60-min ischemia and a 120-min reperfusion period, bilateral nephrectomies were performed. Serum urea, creatinine, neutrophil gelatinase-associated lipocalin (NGAL) levels, tissue total oxidant status (TOS), total antioxidant status (TAS), total thiol (TT), asymmetric dimethylarginine (ADMA) levels, superoxide dismutase (SOD) activity and glutathione peroxidase (GSH-Px) activity were measured. Tissue mRNA expression levels of peroxisome proliferator-activated receptor-ɣ (PPAR-ɣ), nuclear factor erythroid 2-related factor 2 (Nrf2) and nuclear factor kappa-light-chain-enhancer of activated B cells (NF-κB) were analyzed. In addition, renal tissues were evaluated histopathologically and immunohistochemically. All tested drugs reduced renal damage, apoptosis, urea, creatinine, NGAL, TOS, nitric oxide (NO) and ADMA levels, NF-κB, inducible nitric oxide synthase (iNOS) and endothelin-1 (ET-1) expressions (P < 0.001). All tested drugs increased SOD activity, GSH-Px activity, TAS levels, TT levels, endothelial nitric oxide synthase (eNOS) expression, dimethylarginine dimethylaminohydrolases (DDAHs) expression, Nrf2 expression and PPAR-ɣ expression (P < 0.001, P < 0.003). These results suggest that CAP, TEL and BM pretreatment could reduce renal IR injury via anti-inflammatory, antioxidant and anti-apoptotic effects. © 2016 John Wiley & Sons Australia, Ltd.

  13. Development of phytovesicles containing triterpenoids from Samadera indica

    Directory of Open Access Journals (Sweden)

    Vidya Viswanad

    2015-01-01

    Full Text Available Introduction: Samadera indica belonging to Simaroubaceae family is being used traditionally for many diseases including arthritis, edema, itching, skin diseases, constipation, and general debility. Objective: The effectiveness of any drug delivery system depends upon its ability to deliver the active components at therapeutic level. In this study, a novel phyto vesicular formulation for the enhanced topical delivery of methanol extract of S. indica in order to treat skin infections was developed. Materials and Methods: The methanol extract fraction of leaves of S. indica which showed more antifungal activity was purified to separate an antifungal compound. Phytovesicles were formulated using the more antifungal fraction in order to treat topical and deep seated fungal infections. Pytovesicles were prepared using 1:2 molar ratio of antifungal triterpenoid from S. indica (AFTSI-phosphatidylcholine by film hydration method. Results and Discussion: Chloroform 100% fraction of methanol extract of S. indica showed more activity against the fungus Candida albicans. Further purification gave a fraction with minimum inhibitory concentration value of 15.6 mg/ml against C. albicans and showed positive test for triterpenoids. The fraction was named as AFTSI. A compound (20 mg was isolated from this fraction at an R F value. The phytovesicle gel formulated using AFTSI showed enhanced skin permeability and antifungal activity. Conclusion: The study demonstrated that the phytovesicular gel developed using methanol extract of S. indica would be beneficial for treating deep seated fungal infections.

  14. A Novel Triterpenoid Lactone, Schiprolactone A, from Schisandra propinqua (Wall.) Hook. f. et Thoms

    Institute of Scientific and Technical Information of China (English)

    陈业高; 秦国伟; 谢毓元

    2001-01-01

    Schiprolactone A, a triterpenoid lactone with a new side chanin skeleton was isolated from the stems of Schisandra propinqua together with schisanlactones A and B. Their structures were elucidated by spectral studies.

  15. Petatrichol B: A Pentacyclic Triterpenoid with Unusual Skeleton from Petasites tricholobus

    Institute of Scientific and Technical Information of China (English)

    2005-01-01

    A novel pentacyclic triterpenoid, petatrichol B, was isolated from the rhizome of Petasites tricholobus. Its structure was established by means of spectroscopic analysis (EIMS,HRSIMS, IR, 1D NMR and 2D NMR).

  16. Two new triterpenoids from fruiting bodies of fungus Ganoderma lucidum.

    Science.gov (United States)

    Zhao, Zhen-Zhu; Yin, Rong-Hua; Chen, He-Ping; Feng, Tao; Li, Zheng-Hui; Dong, Ze-Jun; Cui, Bao-Kai; Liu, Ji-Kai

    2015-01-01

    Two new triterpenoids, (24E)-9α,11α-epoxy-3β-hydroxylanosta-7,24-dien-26-al (1) and (22Z,24Z)-13-hydroxy-3-oxo-14(13 → 12)abeo-lanosta-8,22,24-trien-26,23-olide (2) were isolated from dried fruiting bodies of fungus Ganoderma lucidum. The structures of these two new compounds were elucidated on the basis of extensive spectroscopic analyses. Compound 1 possessed a lanostane skeleton, while compound 2 was based on a rare 14 (13 → 12)abeo-lanostane skeleton with a 26,23-olide moiety. Both of them were evaluated for their antifungal and cytotoxic activities. Neither of them displayed obvious inhibition on Candida albicans and five human cancer cell lines.

  17. Cytotoxic Triterpenoid Saponins from the Roots of Platycodon grandiflorum

    Directory of Open Access Journals (Sweden)

    Jing-Kui Tian

    2007-04-01

    Full Text Available Bioguided fractionation of the ethanol extracts obtained from Platycodon grandiflorum roots led to isolation of two new triterpenoid saponins, characterized as 3-O-β-D-glucopyranosyl-2β,12α,16α,23,24-pentahydroxyoleanane-28(13-lactone (1 and 3-O-β-D-glucopyranosyl-(1→3-β-D-glucopyranosyl-2β,12α,16α,23α-tetrahydroxyoleanane-28(13- lactone (2 by 1D- and 2D-NMR and MS techniques, as well as chemical means. Both compounds showed cytotoxic activity against human ECA-109 cells.

  18. [Studies on triterpenoids and their glycosides from Aralia dasyphylla Miq].

    Science.gov (United States)

    Yi, Y H; Gu, J Q; Xiao, K; Wang, Z Z; Lin, H W

    1997-10-01

    The structures of two triterpenoids and their glycosides were isolated from Aralia dasyphylla Miq. Their structures have been identified to be oleanoic acid(I), 16 beta-hydroxy-18 beta-H-oleanoic acid(II), oleanoic acid-28-O-beta-D-glucopyranoside(III) and 16 beta-hydroxy-18 beta-H-oleanoic acid-28-O-beta-D-glucopyranoside(IV), respectively, mainly through interpretation of UV, IR, MS, 1H and 13CNMR, DEPT, HMQC and HMBC spectra data. The stereochemistry of II has been confirmed by NOESY. Pharmacological experiments showed that the total saponins exerted preventative effect on CCl4-induced liver injury of male mice and hypoglycemic effect on a model of alloxan-induced diabetes in rats.

  19. A triterpenoid from wild bitter gourd inhibits breast cancer cells

    Science.gov (United States)

    Bai, Li-Yuan; Chiu, Chang-Fang; Chu, Po-Chen; Lin, Wei-Yu; Chiu, Shih-Jiuan; Weng, Jing-Ru

    2016-03-01

    The antitumor activity of 3β,7β,25-trihydroxycucurbita-5,23(E)-dien-19-al (TCD), a triterpenoid isolated from wild bitter gourd, in breast cancer cells was investigated. TCD suppressed the proliferation of MCF-7 and MDA-MB-231 breast cancer cells with IC50 values at 72 h of 19 and 23 μM, respectively, via a PPARγ-independent manner. TCD induced cell apoptosis accompanied with pleiotrophic biological modulations including down-regulation of Akt-NF-κB signaling, up-regulation of p38 mitogen-activated protein kinase and p53, increased reactive oxygen species generation, inhibition of histone deacetylases protein expression, and cytoprotective autophagy. Together, these findings provided the translational value of TCD and wild bitter gourd as an antitumor agent for patients with breast cancer.

  20. Cycloartane-type triterpenoids from Astragalus hoantchy French.

    Science.gov (United States)

    Guo, Kai; He, Xiaofeng; Lu, Dengxue; Zhang, Yanping; Li, Xiuzhuang; Yan, Zhiqiang; Qin, Bo

    2017-02-01

    A new cycloartane-type triterpenoid, 3β-acetoxy-9β,19-cyclolanost-24E-ene-1α,16β-diol-27-O-β-d-glucopyranoside (1), together with three known ones (2-4) were isolated from the aerial parts of Astragalus hoantchy. The structure of compound 1 was elucidated by detailed spectroscopic analyses including 1D and 2D NMR, HRESIMS, and IR experiments. All of the four compounds were isolated from A. hoantchy for the first time. The antifungal activities of compounds 1-4 against a phytopathogenic fungus (Alternaria solani) were evaluated with the result that compound 3 exhibited a moderate activity with an IC50 value of 284 μg/mL.

  1. Two new triterpenoids from the resin of Boswellia carterii.

    Science.gov (United States)

    Wang, Feng; Li, Zhan-Lin; Cui, Hong-Hua; Hua, Hui-Ming; Jing, Yong-Kui; Liang, Sheng-Wang

    2011-03-01

    Two new triterpenoids, 3-oxotirucalla-7,9(11),24-trien-21-oic acid (1) and 18Hα,3β,20β-ursanediol (2), along with 15 known triterpenes, α-amyrin, α-boswellic acid, β-boswellic acid, acetyl α-boswellic acid, acetyl β-boswellic acid, 9,11-dehydro-β-boswellic acid, 9,11-dehydro-α-boswellic acid, acetyl 11α-methoxy-β-boswellic acid, 11-keto-β-boswellic acid, acetyl 11-keto-β-boswellic acid, acetyl α-elemolic acid, 3β-hydroxytirucalla-8,24-dien-21-oic acid, elemonic acid, 3α-hydroxytirucalla-7,24-dien-21-oic acid, and 3α-hydroxytirucall-24-en-21-oic acid, were isolated from the resin of Boswellia carterii Birdw.

  2. New triterpenoids from the stem bark of Hypodaphnis zenkeri.

    Science.gov (United States)

    Momo, Itbert Joseph; Dufat, Thi-Hanh; Wandji, Jean; Michel, Sylvie; Chiozem, David Dako

    2013-01-01

    A new pentacyclic triterpenoid and three new derivatives based on the taraxer-14-ene skeleton with a C-28 attached a carboxylic acid group have been isolated from the stem bark of Hypodaphnis zenkeri, together with six known compounds. The new product was identified as 2α,3α-dihydroxytaraxer-14-en-28-oic acid (1). Its derivatives, 2α,3α-diacetyltaraxer-14-en-28-oic acid (2), 2α,3α-di-O-carbonyl-2α,3α-dihydroxytaraxer-14-en-28-oic acid (3) and 2α,3α-dipropionyltaraxer-14-en-28-oic acid (4) were obtained by semisynthesis. The known compounds were identified as 3β-hydroxytaraxer-14-en-28-oic acid or aleuritolic acid (5) (McPhail, A.T., McPhail, D.R., Wani, M.C., Wall, M.E. & A.W., Nicholas, A.W. (1989). Identity of maprounic acid with aleuritolic acid. Revision of the structure of maprounic acid: X-ray crystal structure of p-bromobenzyl acetylmaprounate. Journal Natural Products, 52, 212), 3α-hydroxytaraxer-14-en-28-oic acid or isoaleuritolic acid (6), 3α-acetyltaraxer-14-en-28-oic acid acetate or aleuritolic acid acetate (7) (Chaudhuri, S.K., Fullas, F., Brown, D.M., Wani, M.C., Wall, M.E., Cai, L., … Kinghorn, A.D. (1995). Isolation and structural elucidation of pentacyclic triterpenoids from Maprounea africana. Journal of Natural Products, 58, 1-9), 3-oxo-taraxer-14-ene or taraxerone (8) β-sitosterol (9) and stigmasterol (10) (Kamboj & Saluja, 2011), together with fatty acids. Their structures were established on the basis of spectroscopic studies and chemical transformations.

  3. Two new biologically active triterpenoidal saponins acylated with salicylic acid from Albizia adianthifolia

    OpenAIRE

    Haddad, Mohamed; Miyamoto, Tomofumi; Laurens, Véronique; Lacaille-Dubois, Marie-Aleth

    2003-01-01

    International audience; Two new oleanane-type triterpene saponins, adianthifoliosides A (1) and B (2), were isolated from a 95% ethanolic extract of roots of Albizia adianthifolia. Their structures were elucidated mainly by using a combination of 600 MHz 1D and 2D NMR techniques (COSY, NOESY, TOCSY, HSQC, and HMBC) and by FABMS and HRESIMS. Compounds 1 and 2 were characterized as glycosides of acacic acid acylated by an o-hydroxybenzoyl unit. The crude saponin mixture (CSM), compounds 1 and 2...

  4. Pentacyclic triterpenoids of Mentha villosa: structural identification and {sup 1}H and {sup 13}C resonance assignments; Triterpenoides pentaciclicos de Mentha villosa: identificacao estrutural e atribuicao dos deslocamentos quimicos dos atomos de hidrogenio e carbono

    Energy Technology Data Exchange (ETDEWEB)

    Monte, Francisco J. Queiroz; Oliveira, Eliete F. de [Ceara Univ., Fortaleza, CE (Brazil). Dept. de Quimica Organica e Inorganica; Braz Filho, Raimundo [Universidade Estadual do Norte Fluminense, Campos dos Goytacazes, RJ (Brazil). Setor de Quimica de Produtos Naturais

    2001-08-01

    The structures of seven oleanene and ursene triterpenoids (1-7) isolated from aerial parts of Mentha villosa were identified. In addition, the complete {sup 1} H and {sup 13} C resonance assignments of these triterpenoids were accomplished using 1D and 2D NMR spectroscopic experiments. (author)

  5. Accumulation and Dynamic Trends of Triterpenoid Saponin in Vegetative Organs of Achyranthus bidentata

    Institute of Scientific and Technical Information of China (English)

    Jinting Li; Zhenghai Hu

    2009-01-01

    The relationship between structural features of various vegetative organs and triterpenoid saponin accumulation in Achyranthus bidentata Blume was investigated using anatomy, histochemistry and phytochemistry. The results showed that the primary and secondary structures of roots, and the structures of stems and leaves of A. bidentata, were similar to those of ordinary dicotyledonous plants. The enlargement of its roots, however, was primarily associated with growth and differentiation of tertiary structures. There were collateral medullary vascular bundles in addition to the normal vascular bundles in the stem. The tertiary structure was not only main parts in the roots of A. bidentata, but also important storage region of triterpenoid saponin in its growth and development. The stem may be the essential transport organ of triterpenoid saponin, while palisade parenchyma may be the primary synthesis location. In November, the total quantity of triterpenoid saponin and overall biomass in the roots reach a maximum level. This was the best time, therefore, to harvest the roots and corresponded to the traditional harvest period. Despite the withered appearance of leaves, stems also contained substantial amounts of triterpenoid saponin, and it was recommended that the stems of A. bidentata should be used.

  6. 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.

  7. [Triterpenoid saponins from flower bud of Jasminum officinale var. grandiflorum].

    Science.gov (United States)

    Zhao, Gui-Qin; Dong, Jun-Xing

    2008-01-01

    To study the chemical constituent bud of the flowers of Jasminum officinale var. grandiflorum. The compounds were isolated and purified by recrystallization and chromatography on silica gel and Sephadex LH - 20 column. Their structures were elucidated on the basis of physicochemical properties and spectral analysis. Six triterpenoid saponins were identified as 3-O-alpha-L-rhamnopyranosyl (1 --> 2)-beta-D-xylopyranosyl- hederagenin-28-O-beta-D-galactopyranosyl (1 --> 6)-beta-D-galactopyranosyl ester (1), hederagenin-3-O-beta-D-glucopyranosyl (1 --> 3)-alpha-L-arabinopyranoside (2), 2alpha, 3beta, 23-trihydroxyolean-12-en-28-oic-O-beta-D-glucopyranosyl ester (3), hederagenin-3-O-beta-D-xylopyranosyl (1 --> 3)-alpha-L-rhamnopyranosyl (1 --> 2)-alpha-L-arabinopyranoside (4), 2alpha, 3beta, 23-trihydroxyolean-12-en-28-oic-O-alpha-L-rhamnopyranosyl (1 --> 4)-beta-D-glucopyranosyl (1 --> 6)-beta-D-glucopyranosyl ester (5), hederagenin-3-O-alpha-L-rhamnopyranosyl (1 --> 2)-alpha-L-arabinopyranoside (6). Compound 1 is a new compound. Compounds 2, 3, 4, 5, 6 were isolated from the genus Jasminum for the first time.

  8. Two New and Four Known Triterpenoids from Boswellia sacra Fluckiger

    Directory of Open Access Journals (Sweden)

    Liaqat Ali

    2014-07-01

    Full Text Available Two new O-acetyl derivatives of pentacyclic triterpenic acids, 3α-acetoxyurs -5:12-dien-24-oic acid ( 1 and 3α-acetoxylup -12:20 (29-dien-24-oic acid ( 2 were isolated from Omani frankincense of Boswellia sacra Flueckiger along with four known compounds: commic acid-D (3, 9,11-dehydro-β-boswellic acid (4, 3β-Hydroxy-11-oxours-12-ene (5, and 11β-Hydroxy-3-oxours-12-ene (6 . The structures of new compounds 1 and 2 were elucidated on the basis of detailed mass and NMR spectroscopic analysis using 1H NMR, 13C NMR, HMQC, HMBC, COSY, and HREIMS techniques. The relative configurations of 1 and 2 were assigned by comparative analysis of the NMR spectral data with the related known triterpenoids together with NOESY experiments. The structures of the known compounds 3-6 were confirmed by the comparative analysis of the reported mass and NMR data.

  9. 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.

  10. Tetracyclic triterpenoids and terpenylated coumarins from the bark of Ailanthus altissima ("Tree of Heaven").

    Science.gov (United States)

    Hong, Zhi-Lai; Xiong, Juan; Wu, Shi-Biao; Zhu, Jing-Jing; Hong, Jun-Lin; Zhao, Yun; Xia, Gang; Hu, Jin-Feng

    2013-02-01

    Tetracyclic triterpenoids (named as altissimanins A-E, 1-5) and a terpenylated coumarin (denominated as altissimacoumarin G, 6), along with fifteen known compounds (7-21) were isolated from the bark of Ailanthus altissima. Structures of compounds 1-6 were established by spectroscopic methods and chemical transformations. Altissimanin A (1) is a tirucallane-type triterpenoid bearing an uncommon oxetane ring in the side-chain, while altissimanins D (4) and E (5) are two unprecedented dimers each consisting of one tirucallane-type and one dammarane-type triterpenoid moiety. All the isolates were evaluated for their cytotoxic effects against a small panel of human cancer cell lines. Copyright © 2012 Elsevier Ltd. All rights reserved.

  11. A new biologically active triterpenoid saponin from the leaves of Lepidagathis hyalina Nees.

    Science.gov (United States)

    Yadava, R N

    2001-01-01

    A new biologically active triterpenoid saponin m.f. C42H68O13, m.p. 315 degrees-317 degrees C was isolated from the ethyl acetate soluble fraction of the methanolic extract of the leaves of Lepidagathis hyalina. Its structure was characterized as 3-beta-O-[alpha-L-rhamnopyranosyl(1-->4)O-beta-D-glucopyranosyl]16-alpha-hydroxy-olean-12-en(13)-28-oic acid by several spectral and chemical analysis. This new triterpenoid saponin showed antimicrobial activity against various plants pathogenic bacteria and fungi.

  12. Information entropy-based classification of triterpenoids and steroids from Ganoderma.

    Science.gov (United States)

    Castellano, Gloria; Torrens, Francisco

    2015-08-01

    A set of 71 triterpenoid and steroid compounds from Ganoderma were periodically classified using a procedure based on information entropy with artificial intelligence. Six features were used in hierarchical order to classify the triterpenoids and steroids structurally. The phytochemicals belonging to the same group in the periodic table present similar antioxidant activity, and those compounds belonging to the same period exhibit maximum resemblance. The periodic classification is related to the experimental bioactivity and antioxidant potency data that are available in the literature: a steroid with a three-ketone group conjugated with two carbon-carbon double bonds in the right side of the periodic table exhibits the greatest antioxidant activity.

  13. 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.

  14. The First Occurrence of A Mallotus 3,4-Seco-Taraxerane Triterpenoid from Mallotus barbatus

    Directory of Open Access Journals (Sweden)

    Phan Minh Giang

    2013-03-01

    Full Text Available The first occurrence of a 3,4-seco-taraxerane triterpenoid in Mallotus species (Euphorbiaceae is reported. The triterpenoid was isolated from the leaves of the Vietnamese medicinal plant Mallotus barbatus ( Wall. Muell.-Arg. and its structure was determined to be 3,4-seco-taraxer-14-en-3-oic acid on the basis of HR-MS and NMR spectroscopic methods. For the first time, the 1 H and 13C NMR data and stereochemistry of this compound were fully established on the basis of the 1H- 1H COSY, NOESY, HSQC, and HMBC spectroscopic data.

  15. A new triterpenoid saponin from the root of Croton lachnocarpus Benth.

    Science.gov (United States)

    Pan, Zheng-Hong; Ning, De-Sheng; Liu, Jin-Lei; Pan, Bo; Li, Dian-Peng

    2014-01-01

    A new triterpenoid saponin, 3-O-β-D-xylopyranosyl spathodic acid (1), was isolated from the EtOH extract of the root of Croton lachnocarpus Benth., together with four known compounds. These compounds were characterised on the basis of their spectral data and compatible with values in the literature. Compound 1 was the first triterpenoid glucoside isolated from the genus Croton. The known compound myriaboric acid (2) showed cytotoxic activity against human hepatocellular carcinoma SMMC-7721 cell line with an IC50 value of 42.2 μM.

  16. 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.

  17. Cytotoxic triterpenoid saponins from the fruits of Aesculus pavia L.

    Science.gov (United States)

    Zhang, Zhizhen; Li, Shiyou

    2007-08-01

    Continued chemical investigation on the fruits of North American Aesculus pavia L. resulted in the isolation and identification of 13 polyhydroxyoleanene pentacyclic triterpenoid saponins, named aesculiosides IIe-IIk (1-7), and IIIa-IIIf (8-13), together with 18 known compounds: aesculiosides Ia-Ie (14-18), IIa-IId (19-22), IVa-IVc (23-25), 3-O-[beta-D-galactopyranosyl(1-->2)]-alpha-L-arabinofuranosyl(1-->3)-beta-D-glucuronopyranosyl-21,22-O-diangeloyl-3beta,15 alpha,16 alpha,21 beta,22 alpha,28-hexahydroxyolean-12-ene (26), 3-O-[beta-D-glucopyranosyl(1-->2)]-alpha-L-arabinofuranosyl(1-->3)-beta-D-glucuronopyranosyl-21,22-O-diangeloyl-3beta,16 alpha,21 beta,22 alpha,24 beta,28-hexahydroxyolean-12-ene (27), 3-O-[beta-D-galactopyranosyl(1-->2)]-alpha-L-arabinofuranosyl(1-->3)-beta-D-glucuronopyranosyl-21,22-O-diangeloyl-3beta,16 alpha,21 beta,22 alpha,28-pentahydroxyolean-12-ene (28), R(1)-barrigenol (29), scopolin (30), and 5-methoxyscopolin (31). The structures of these compounds were elucidated by spectroscopic and chemical analyses. Compounds 14-22 and 26-28 were tested in vitro for their activity against 59 cell lines from nine different human cancers including leukemia, non-small cell lung, colon, CNS, melanoma, ovarian, renal, prostate, and breast. It was found that compounds with two-acyl groups at C-21 and C-22 had cytotoxic activity for all cell lines tested with GI(50) 0.175-8.71 microM, while compounds without acyl groups at C-21 and C-22 had weak or no cytotoxic activity. These results suggest that the acyl groups at C-21 and C-22 are essential for their activity.

  18. 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.

  19. 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 emulsio

  20. 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.

  1. Expedient preparative isolation and tandem mass spectrometric characterization of C-seco triterpenoids from Neem oil.

    Science.gov (United States)

    Haldar, Saikat; Mulani, Fayaj A; Aarthy, Thiagarayaselvam; Dandekar, Devdutta S; Thulasiram, Hirekodathakallu V

    2014-10-31

    C-seco triterpenoids are widely bioactive class of natural products with high structural complexity and diversity. The preparative isolation of these molecules with high purity is greatly desirable, although restricted due to the complexity of natural extracts. In this article we have demonstrated a Medium Pressure Liquid Chromatography (MPLC) based protocol for the isolation of eight major C-seco triterpenoids of salannin skeleton from Neem (Azadirachta indica) oil. Successive application of normal phase pre-packed silica-gel columns for the fractionation followed by reverse phase in automated MPLC system expedited the process and furnished highly pure metabolites. Furthermore, eight isolated triterpenoids along with five semi-synthesized derivatives were characterized using ultra performance liquid chromatography-electrospray ionization-quadrupole/orbitrap-MS/MS spectrometry as a rapid and sensitive identification technique. The structure-fragment relationships were established on the basis of plausible mechanistic pathway for the generation of daughter ions. The MS/MS spectral information of the triterpenoids was further utilized for the identification of studied molecules in the complex extract of stem and bark tissues from Neem. Copyright © 2014 Elsevier B.V. All rights reserved.

  2. A New Antioxidant Triterpenoid from the Stem Wood of Sorbus lanata

    Directory of Open Access Journals (Sweden)

    Abdul Latif

    2014-01-01

    Full Text Available In search for antioxidant constituents, a new triterpenoid (1 along with three known compounds (2-4 were isolated from Sorbus lanata . LCMS, HR-ESIMS, and advanced NMR (1D & 2D data were used for the determination of structures and spectral assignments. The isolated compounds were also tested for their antioxidant activities in the diphenylpicrylhydrazyl (DPPH radical scavenging assay.

  3. Fast separation of triterpenoids by supercritical fluid chromatography/evaporative light scattering detector.

    Science.gov (United States)

    Lesellier, E; Destandau, E; Grigoras, C; Fougère, L; Elfakir, C

    2012-12-14

    The screening of plant material, the chemical composition, the abundance and the biological activity of triterpenoids are of a major economical importance. The classical analytical methods, such as TLC, GC, and HPLC are either little resolutive, or require derivatization steps, or fail in sensitivity. The supercritical fluid chromatography/evaporative light scattering detector (SFC/ELSD) coupling provides high resolution, fast analysis and higher responses for the analysis of triterpenoids. After the initial screening of seven stationary phases to select the well suited one, analytical conditions (modifier percentage, from 10 to 3%; backpressure (from 12 to 18 MPa) and temperature (from 15 to 25 °C) were studied to improve the separation, and ELSD detection of a standard mixture composed of 8 triterpenoids (oleanolic acid, erythrodiol, β-amyrin, ursolic acid, uvaol, betulinic acid, betulin, lupeol). Applied to apple pomace extracts, this method allows the separation of about 15 triterpenoid compounds, in less than 20 min, with isocratic conditions. Moreover, the ELSD response is dramatically higher than the one provided by UV detection, and avoids derivatization steps. An attempt to identify some compounds was done by collecting chromatographic peaks and further analyzing them with mass spectrometry. Complete identification or molecular formula could be proposed for 11 compounds. However, due to the presence of position and orientation isomers the absolute identification remains difficult, despite some retention rules deduced from the standard analysis.

  4. Cloning and characterization of farnesyl diphosphate synthase gene involved in triterpenoids biosynthesis from Poria cocos.

    Science.gov (United States)

    Wang, Jianrong; Li, Yangyuan; Liu, Danni

    2014-12-02

    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.

  5. 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

  6. A New Triterpenoid Spaonin Isolated from the Seeds of Aesculus assamica Griff

    Institute of Scientific and Technical Information of China (English)

    Hong Wei LIU; Xin Sheng YAO; Nai Li WANG; Guo Ping CAI

    2006-01-01

    A new triterpenoid saponin, 21β-angeloylprotoaescigenin-3β-O-[α-L-rhamnopyranosyl(1-3)]β-D-glucopyranosiduronic acid 1, was isolated from the seeds of Aesculus assamica Griff. Its structure was elucidated on the basis of spectroscopic data analysis.

  7. Schisanlactone G,a new 3,4-seco-lanostane triterpenoid from Schisandra sphenanthera

    Institute of Scientific and Technical Information of China (English)

    Rong Ren; Guo Jun Luo; Hong Mei Li; Zhao Yuan Wu; Hai Zhou Li; Rong Tao Li

    2009-01-01

    A new 3,4-seco-lanostane triterpenoid,schisanlactone G (1),was isolated from the fruits of Schisandra sphenanthera.Its structure was established on the basis of extensive spectroscopic analysis.2009 Rong Tao Li.Published by Elsevier B.V.on behalf of Chinese Chemical Society.All fights reserved.

  8. Sebiferone, a New Triterpenoid from Stem Bark of Sapium sebiferum (L.) Roxb.

    Institute of Scientific and Technical Information of China (English)

    2002-01-01

    From the stem bark of Sapium sebiferum a new triterpenoid, named sebiferone (1), was isolated. The structure of the new compound was elucidated as 3β-acetoxy-D-friedoolen-14-en -1-one-28-oic acid on the basis of spectral and chemical methods.

  9. Isolation, Characterization, and Surfactant Properties of the Major Triterpenoid Glycosides from Unripe Tomato Fruits

    NARCIS (Netherlands)

    Yamanaka, T.; Vincken, J.P.; Waard, de P.; Sanders, M.G.; Takada, N.; Gruppen, H.

    2008-01-01

    Various triterpenoid glycosides were extracted from whole unripe tomato fruits (Lycopersicon esculentum cv. Cedrico), using aqueous 70% (v/v) ethanol to study their surfactant properties. Cation-exchange chromatography using a Source 15S column and subsequent semipreparative HPLC using an XTerra RP1

  10. Isolation, Characterization, and Surfactant Properties of the Major Triterpenoid Glycosides from Unripe Tomato Fruits

    NARCIS (Netherlands)

    Yamanaka, T.; Vincken, J.P.; Waard, de P.; Sanders, M.G.; Takada, N.; Gruppen, H.

    2008-01-01

    Various triterpenoid glycosides were extracted from whole unripe tomato fruits (Lycopersicon esculentum cv. Cedrico), using aqueous 70% (v/v) ethanol to study their surfactant properties. Cation-exchange chromatography using a Source 15S column and subsequent semipreparative HPLC using an XTerra

  11. Nanoencapsulation of natural triterpenoid celastrol for prostate cancer treatment

    Directory of Open Access Journals (Sweden)

    Sanna V

    2015-10-01

    Full Text Available Vanna Sanna,1,2 Jean Christopher Chamcheu,3 Nicolino Pala,1 Hasan Mukhtar,3 Mario Sechi,1,2 Imtiaz Ahmad Siddiqui3 1Department of Chemistry and Pharmacy, University of Sassari, Sassari, Italy; 2Laboratory of Nanomedicine, University of Sassari, Sassari, Italy; 3Department of Dermatology, University of Wisconsin, Madison, WI, USA Abstract: Celastrol (CL, a triterpenoid extracted from the Chinese herb Tripterygium wilfordii, has recently attracted interest for its potential antitumor effects. However, unfavorable physicochemical and pharmacokinetics properties such as low solubility, poor bioavailability, and systemic toxicity, are limiting its therapeutic application. In this context, the development of innovative nanocarriers can be useful to overcome these issues, and nanoencapsulation would represent a powerful strategy. In this study, we developed novel CL-loaded poly(ε-caprolactone nanoparticles (NPs, and investigated their antiproliferative efficacy on prostate cancer cells. CL-NPs were prepared using a nanoprecipitation method and fully characterized by physicochemical techniques. The antiproliferative effects on LNCaP, DU-145, and PC3 cell lines of CL-NPs, compared to those of free CL at different concentrations (0.5, 1.0, and 2.0 µM, were investigated. Moreover, fluorescence microscopy was utilized to examine the cellular uptake of the nanosystems. Furthermore, to elucidate impact of nanoencapsulation on the mechanism of action, Western analyses were conducted to explore apoptosis, migration, proliferation, and angiogenesis alteration of prostate cancer cells. The results confirmed that CL-NPs inhibit proliferation dose dependently in all prostate cancer cells, with inhibitory concentration50 less than 2 µM. In particular, the NPs significantly increased cytotoxicity at lower/medium dose (0.5 and 1.0 µM on DU145 and PC3 cell lines with respect to free CL, with modulation of apoptotic and cell cycle machinery proteins. To date, this

  12. Effects of triterpenoid from Schisandra chinensis on oxidative stress in alcohol-induced liver injury in rats.

    Science.gov (United States)

    Li, Bin; Zhu, Lijie; Wu, Ting; Zhang, Jiachen; Jiao, Xinyao; Liu, Xiuying; Wang, Yanqun; Meng, Xianjun

    2015-03-01

    Alcohol-induced oxidative stress plays a crucial role in the pathological development of alcoholic liver disease. The aim of this study was to investigate the effects of triterpenoid from Schisandra chinensis on oxidative stress in alcohol-induced liver injury in rats. We found that the administration of triterpenoid attenuated alcohol-induced oxidative stress in multiple organs including liver. Moreover, the impaired liver function and histological changes resulted from alcohol consumption was improved by triterpenoid treatment. Finally, we found that pretreatment with triterpenoid from Schisandra chinensis to alcohol-fed rats increased the expression level of haem oxygenase-1 (HO-1) while inhibited the induction of cytochrome P-450 2E1 (CYP2E1) in liver microsomes. Further assays revealed that the microsomal activity of HO-1 was accordingly induced whereas CYP2E1 was suppressed in rats received triterpenoid intervention. Our findings suggest that triterpenoid from Schisandra chinensis may protect against alcohol-induced liver injury through ameliorating oxidative stress in rats.

  13. Δ2-Triterpenes: Early intermediates in the diagenesis of terrigenous triterpenoids

    Science.gov (United States)

    ten Haven, H. L.; Peakman, T. M.; Rullkötter, J.

    1992-05-01

    A series of Δ2-triterpenoids (oleana-2,12-diene, oleana-2,13(18)-diene, oleana-2,18-diene, ursa-2, 12-diene, and taraxera-2,14-diene) has been identified in Holocene buried mangrove sediments (Florida, USA) by comparison of the mass spectra of and by co-injections with authentic standards. In the Oligocene Brandon lignite (Vermont, USA) oleana-2,12-diene and oleana-2,13(18)-diene were also identified, along with two A-ring contracted amyrin derivatives. By comparison with the sedimentary occurrence of related analogues of oxyallobetulin and betulin and the demonstrated diagenetic formation of lup-2-ene from lupan-3-one, these novel terrigenous biological markers are considered diagenetic products formed by dehydration of precursor molecules, such as α- and β-amyrin, and taraxerol. The identification of these early intermediates brings us one step closer to the full understanding of the diagenetic fate of terrigenous triterpenoids.

  14. 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.

  15. Tubiferic acid, a new 9,10-secocycloartane triterpenoid acid isolated from the myxomycete Tubulifera arachnoidea.

    Science.gov (United States)

    Ippongi, Yukihito; Ohtsuki, Takashi; Toume, Kazufumi; Arai, Midori A; Yamamoto, Yukinori; Ishibashi, Masami

    2011-01-01

    Tubiferic acid (1), a new triterpenoid acid having a 2,6-dimethyl-4,5-dihydroxy-2-hexenoic acid moiety as a side chain, was isolated from field-collected fruit bodies of the myxomycete Tubulifera arachnoidea, and its structure was elucidated by spectral data. Tubiferic acid (1) had the same unique 9,10-secocycloartane carbon skeleton as tubiferal A (2). © 2011 Pharmaceutical Society of Japan

  16. Highly oxygenated triterpenoids from the roots of Schisandra chinensis and their anti-inflammatory activities.

    Science.gov (United States)

    Song, Qiu-Yan; Gao, Kun; Nan, Zhi-Biao

    2016-01-01

    A new highly oxygenated triterpenoid, schinchinenlactone D (1), and three known compounds (2-4) were isolated from the roots of Schisandra chinensis. Their structures were determined by combining the spectroscopic analysis with the theoretical computations. The anti-inflammatory activities of compounds 1-4 were evaluated, and compound 3 exhibits the most significant activity in the inhibition of NO production with an IC50 value of 10.6 μM.

  17. A New Triterpenoid Saponin and Antimicrobial Activity of Ethanolic Extract from Sapindus mukorossi Gaertn.

    OpenAIRE

    Amita Sharma; Satish Chandra Sati; Om Prakash Sati; Maneesha Dobhal Sati; Sudhir Kumar Kothiyal; Deepak Kumar Semwal; Anil Mehta

    2013-01-01

    A new acetylated triterpenoid saponin elucidated as hederagenin-3-O-β-D-xylopyranosyl (2→1)-[3-O-acetyl-α-L-arabinopyranosyl-28-O-α-L-rhamnopyranosylester has been isolated from pericarps of Sapindus mukorossi Gaertn. The structure of the compound was determined by means of chemical and spectral analysis including advanced 2D NMR studies. The ethanolic extract from pericarps of the plant showed significant in vitro antimicrobial activity against various test organisms by Agar well diffusion m...

  18. Isolation and Simultaneous Quantification of Nine Triterpenoids from Rosa davurica Pall.

    Science.gov (United States)

    Huo, Yayu; Gao, Yang; Mi, Jie; Wang, Xinrui; Jiang, Huimin; Zhang, Hailong

    2017-02-01

    Rosa davurica Pall. has been used as a traditional Oroqen medicine to treat dyspepsia, gastroenterologia, menoxenia and other diseases. In this study, the chemical constituents research on the fruit pulp of R. davurica led to the isolation and identification of nine bioactive pentacyclic triterpenoids and five of them were isolated from the plant for the first time. Subsequently a simple and rapid high-performance liquid chromatography (HPLC) method was established for the simultaneous quantification of the nine triterpenoids. The separation was performed on a Merges reverse phase (RP) C18 (250 × 4.6 mm, 5 μm) column through 40 min gradient delivery of 0.05% phosphoric acid aqueous solution and acetonitrile at a flow rate of 1.2 mL/min at 30°C and the detection wavelength selected was 210 nm. All of the calibration curves showed good linearity (R(2) > 0.9990) in the tested ranges. The limit of detection and the limit of quantitation were in the range of 0.21-1.27 μg/mL and 0.63-3.80 μg/mL, respectively. The established method also showed good precision, repeatability and recovery and can be used to the routine quality control of R. davurica and other herbs containing pentacyclic triterpenoids.

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

    Directory of Open Access Journals (Sweden)

    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.

  20. 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.

  1. 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.

  2. Analysis of three types of triterpenoids in tetraploid white birches (Betula platyphylla Suk.) and selection of plus trees

    Institute of Scientific and Technical Information of China (English)

    Sui Wang; Hui Zhao; Jing Jiang; Guifeng Liu; Chuanping Yang

    2015-01-01

    Betulin, oleanolic acid, and betulinic acid are naturally occurring pentacyclic triterpenoids that have significant medicinal value. Considerable amounts of these triterpenoids are available in the outer bark of white birch. In this study, we used ultrasound-assisted extraction (UAE) to extract triterpenoids from birch bark rapidly and with high efficiency. Using high performance liquid chro-matography (HPLC), three types of triterpenoids were separated and detected. We examined the differences among triterpenoids extracted from diploid versus tetra-ploid white birch. Then, we used factor analysis to screen out tetraploid white birches with comprehensively excel-lent performance. The results indicate that the optimum conditions for extraction include the use of ethanol as an extraction solvent, a solid-to-liquid ratio of 0.1 g/10 ml, ultrasonic power set at 100 W, a temperature of 60 ?C and an extraction time of 15 min. A reversed-phase C18 col-umn (4.6 mm 9 250 mm 9 5 lm) with a column tem-perature of 30 ?C and the mobile phase composed of A (acetonitrile) and B (0.1% aqueous phosphoric acid, v/v) at a flow rate of 0.5 ml/min were used, and the detection wavelength was 195 nm. No significant difference was observed between diploid and tetraploid white birch in terms of the content of three types of triterpenoids (at a confidence level of 0.05). As triterpenoid content, height, and DBH (diameter at breast height) are strongly interre-lated, we used factor analysis to evaluate all individuals, and we screened out six plus trees with excellent com-prehensive characters.

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

    Science.gov (United States)

    Zou, Li-Wei; Dou, Tong-Yi; Wang, Ping; Lei, Wei; Weng, Zi-Miao; Hou, Jie; Wang, Dan-Dan; Fan, Yi-Ming; Zhang, Wei-Dong; Ge, Guang-Bo; Yang, Ling

    2017-01-01

    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 simulations

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

    Directory of Open Access Journals (Sweden)

    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

  5. Triterpenoids isolated from apple peels have potent antiproliferative activity and may be partially responsible for apple's anticancer activity.

    Science.gov (United States)

    He, Xiangjiu; Liu, Rui Hai

    2007-05-30

    Bioactivity-guided fractionation of apple peels was used to determine the chemical identity of bioactive constituents. Thirteen triterpenoids were isolated, and their chemical structures were identified. Antiproliferative activities of the triterpenoids against human HepG2 liver cancer cells, MCF-7 breast cancer cells, and Caco-2 colon cancer cells were evaluated. Most of the triterpenoids showed high potential anticancer activities against the three human cancer cell lines. Among the compounds isolated, 2alpha-hydroxyursolic acid, 2alpha-hydroxy-3beta-{[(2E)-3-phenyl-1-oxo-2-propenyl]oxy}olean-12-en-28-oic acid, and 3beta-trans-p-coumaroyloxy-2alpha-hydroxyolean-12-en-28-oic acid showed higher antiproliferative activity toward HepG2 cancer cells. Ursolic acid, 2alpha-hydroxyursolic acid, and 3beta-trans-p-coumaroyloxy-2alpha-hydroxyolean-12-en-28-oic acid exhibited higher antiproliferative activity against MCF-7 cancer cells. All triterpenoids tested showed antiproliferative activity against Caco-2 cancer cells, especially 2alpha-hydroxyursolic acid, maslinic acid, 2alpha-hydroxy-3beta-{[(2E)-3-phenyl-1-oxo-2-propenyl]oxy}olean-12-en-28-oic acid, and 3beta-trans-p-coumaroyloxy-2alpha-hydroxyolean-12-en-28-oic acid, which displayed much higher antiproliferative activities. These results showed the triterpenoids isolated from apple peels have potent antiproliferative activity and may be partially responsible for the anticancer activities of whole apples.

  6. Hepatoprotective Effects and Mechanisms of Action of Triterpenoids from Lingzhi or Reishi Medicinal Mushroom Ganoderma lucidum (Agaricomycetes) on α-Amanitin-Induced Liver Injury in Mice.

    Science.gov (United States)

    Wu, Huihui; Tang, Shanshan; Huang, Zhaoqin; Zhou, Qian; Zhang, Ping; Chen, Zuohong

    2016-01-01

    Most fatal mushroom poisonings are caused by species of the genus Amanita; the amatoxins are responsible for acute liver failure and death in humans. Ganoderma lucidum is a well-known traditional medicinal mushroom that has been shown to have obvious hepatoprotective effects. This study evaluated the hepatoprotective effects of triterpenoids from G. lucidum on liver injury induced by a-amanitin (α-AMA) in mice and the mechanisms of action of these triterpenoids, including radical scavenging and antiapoptosis activities. Mice were treated with α-AMA, followed by G. lucidum total triterpenoids or individual triterpenoids, and their hepatoprotective effects were compared with those of the reference drug silibinin (SIL). Treatment with SIL, G. lucidum total triterpenoids, and each of the 5 individual triterpenoids significantly reduced serum alanine aminotransaminase and aspartate ami- notransaminase concentrations and reduced mortality rates 20-40%. Moreover, triterpenoids and SIL significantly enhanced superoxide dismutase and catalase activity and reduced malondialdehyde content in livers. Treatment with ganoderic acid C2 significantly inhibited DNA fragmentation and decreased caspase-3, -8, and -9 activities. The results demonstrated that triterpenoids have hepatoprotective effects on α-AMA-induced liver injury and that their hepatoprotective mechanisms may be the result of their antioxidative and radical scavenging activities and their inhibition of apoptosis.

  7. Inhibitory Effects of seco-Triterpenoids from Acanthopanax sessiliflorus Fruits on HUVEC Invasion and ACE Activity.

    Science.gov (United States)

    Lee, Jin-Won; Baek, Nam-In; Lee, Dae-Young

    2015-09-01

    This study was conducted to investigate the effects of the crude extract from Acanthopanax sessiliflorus fruits and the isolated seco-triterpenoids from the crude extract on blood flow in human umbilical vein endothelial cell (HUVEC) invasion assay and angiotensin converting enzyme (ACE) inhibitory activity assay. On the basis of DMSO, the extent of HUVECs' invasion was remarkably decreased with crude extract concentrations of 400 and 1000 pg/mL. Additionally, the extent of the HUVEC invasion inhibitory effect in 400 and 1000 µg/mL of acanthosessilioside F were 55.8% and 72.4%, respectively. In addition, the maximum extent of the HUVEC invasion inhibitory effect of 22-α-hydroxychiisanoside was 88.9%. The IC50 value of the inhibitory effect on ACE activity in the crude extract was 4 µg/mL. The isolated seco-triterpenoids, 22α-hydroxychiisanogenin, 3,4-seco-lupan-20(30)-en-3,28-dioic acid, (lR)-1,4-epoxy-11α,22α-hydroxy-3,4-seco-lupan-20(30)-en-3,28-dioicacid, (+)-divaroside, and chiisanosidehad showed very high inhibitory effects on ACE activity, ranging from 1.8 to 2.9 µg/mL, which is much higher than the 150.0 µg/mL effect of aspirin. These results suggest that the crude extract from Acanthopanax sessiliflorus fruits and the isolated seco-triterpenoids from the crude extract enhance the blood flow effect by decreasing ACE activity.

  8. Kadcoccinones A-F, New Biogenetically Related Lanostane-Type Triterpenoids with Diverse Skeletons from Kadsura coccinea.

    Science.gov (United States)

    Hu, Zheng-Xi; Shi, Yi-Ming; Wang, Wei-Guang; Li, Xiao-Nian; Du, Xue; Liu, Miao; Li, Yan; Xue, Yong-Bo; Zhang, Yong-Hui; Pu, Jian-Xin; Sun, Han-Dong

    2015-09-18

    Six new lanostane-related triterpenoids, kadcoccinones A-F (1-6), were isolated from Kadsura coccinea. Compound 3 possesses a novel 6/6/9-fused carbocyclic core containing a rare oxabicyclo[4.3.1]decane system. Compounds 4 and 5 are isomers representing the first example of the 18(13 → 12)-abeo-26-norlanostane triterpenoid. The absolute configurations of 1 and 4-6 were defined by X-ray diffraction and experimental ECD spectra, and that of 3 was elucidated by quantum chemical calculations. The plausible biogenetic pathway of 1-6 is postulated.

  9. Triterpenoids from the Roots of Rhaphiolepis indica var. tashiroi and Their Anti-Inflammatory Activity

    Directory of Open Access Journals (Sweden)

    Ian-Lih Tsai

    2013-04-01

    Full Text Available Two new triterpenoids, 2α,3β-dihydroxyolean-11,13(18-dien-19β,28-olide (1 and 3β,5β-dihydroxyglutinol (2, together with eight known compounds (3–10 were isolated from the roots of Rhaphiolepis indica var. tashiroi (Rosaceae. The structures of 1–10 were determined by spectroscopic techniques. Among these isolates, 2α,3β-dihydroxyolean-13(18-en-28-oic acid (9 exhibited inhibitory effect on N-formyl-methionyl-leucyl-phenylalanine (fMLP-induced superoxide production, with an IC50 value of 16.50 μM.

  10. A new bioactive ursane-type triterpenoid from Croton bonplandianum Bail

    Indian Academy of Sciences (India)

    Pranab Ghosh; Amitava Mandal; Mohammad Golam Rasul

    2013-03-01

    A new triterpenoid 3-hydroxy-urs-12,15-dien (1) of ursane skeleton along with three others, viz. oleanolic acid (2) and ursolic acid (3) and -sitosterol (4) were isolated from the root of Croton bonplandianum Bail. Their chemical structures were established on the basis of spectroscopic analysis (IR, 1D NMR, 2D NMR, Mass, etc.) and by chemical means. A probable biosynthetic pathway of compound 1 was also proposed. Preliminary investigation with the new compound showed potent activity against a series of fungal pathogens.

  11. 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)

  12. 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.

  13. Identification of triterpenoid compounds of Centella asiatica by thin-layer chromatography and mass spectrometry.

    Science.gov (United States)

    Bonfill, Mercè; Mangas, Susana; Cusidó, Rosa M; Osuna, Lidia; Piñol, M Teresa; Palazón, Javier

    2006-02-01

    The identification of the four principal triterpenoid components of Centella asiatica has been achieved by TLC on silica gel plates and mass spectrometry, as a modification of the method described in the European Pharmacopoeia (5th edn). A combination of ethyl acetate and methanol as the mobile phase was found to be successful in separating these compounds from the rest of the main components of the extract. The spots were detected with anisaldehyde solution. The separated compounds were confirmed by MALDI -TOF mass spectrometry.

  14. Isolation and Structure Elucidation of a New Triterpenoid from Prunus cerasoides D. Don

    Directory of Open Access Journals (Sweden)

    Liaqat Ali

    2013-03-01

    Full Text Available One new metabolite, prunol (1, belonging to the pentacyclic triterpenoid skeleton was purified from the dichloromethane soluble fraction of the crude ethanolic extract of Prunus cerasoides D. Don. The structure elucidation was accomplished on the basis of one dimensional 1H and 13C NMR and two dimensional HMQC, HMBC, and COSY experiments. The molecular mass was determined by HRFAB-MS, while the major fragments were observed in the EI-MS. The comparative analysis of the NMR spectral data with the known analogues and the NOESY experiments were helpful in assigning the stereo centers in the molecule.

  15. Antifungal activity of bioactive triterpenoid saponin from the seeds of Cassia angustifolia.

    Science.gov (United States)

    Khan, Noor Afshan; Srivastava, Ashutosh

    2009-01-01

    A novel oleanen type triterpenoid glycoside has been isolated from butanolic seed extracts of Cassia angustifolia. Its structure was elucidated as 3-O-{beta-D-glucuronopyranosyl-(1 --> 4)-[beta-D-galactopyranosyl-(1 --> 2)]-beta-D-xylopyranosyl-(1 --> 3)-beta-D-glucopyranosyl}-2, 16alpha-dihydroxy-4, 20-hydroxy methyl olean-12-ene-28-oic acid on the basis of spectral evidence (i.e. FTIR, (1)H NMR, (13)C NMR and FAB-MS data). The isolated saponin was tested for its antifungal activity, where the maximum inhibition was found in Colletotrichium dematium.

  16. A New Triterpenoid Saponin and Antimicrobial Activity of Ethanolic Extract from Sapindus mukorossi Gaertn.

    Directory of Open Access Journals (Sweden)

    Amita Sharma

    2013-01-01

    Full Text Available A new acetylated triterpenoid saponin elucidated as hederagenin-3-O-β-D-xylopyranosyl (2→1-[3-O-acetyl-α-L-arabinopyranosyl-28-O-α-L-rhamnopyranosylester has been isolated from pericarps of Sapindus mukorossi Gaertn. The structure of the compound was determined by means of chemical and spectral analysis including advanced 2D NMR studies. The ethanolic extract from pericarps of the plant showed significant in vitro antimicrobial activity against various test organisms by Agar well diffusion method.

  17. A new triterpenoid saponin and an oligosaccharide isolated from the fruits of Sapindus mukorossi.

    Science.gov (United States)

    Zhang, Xuan-Ming; Yang, De-Po; Xie, Zhi-Yong; Xue, Xue; Zhu, Long-Ping; Wang, Dong-Mei; Zhao, Zhi-Min

    2014-01-01

    A new triterpenoid saponin (1) and a new oligosaccharide (2), together with three known saponins (3-5), have been isolated from n-BuOH extract of the fruits of Sapindus mukorossi Gaertn. The structures were elucidated using detailed analysis of one- and two-dimensional nuclear magnetic resonance spectra along with their mass spectrometric data and the results of acid hydrolysis. Of the isolated compounds 1 and 3-5 displayed cytotoxic effects against human cancer cell lines in A-549 (lung carcinoma), MDA-231 (breast carcinoma) and PC-3 (prostatic carcinoma).

  18. 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.

  19. Novel lanostane and rearranged lanostane-type triterpenoids from Abies sachalinensis - II -.

    Science.gov (United States)

    Gao, Hui Yuan; Wu, Li Jun; Nakane, Takahisa; Shirota, Osamu; Kuroyanagi, Masonori

    2008-04-01

    In the previous work we reported five A-seco-rearranged lanostane triterpenoids as antibacterial constituents from the ethyl acetate soluble fraction of Abies sachalinensei leaves. In further study on the isolation of constituents from the ethyl acetate soluble fraction, two new rearranged lanostane and lanostane-type triterpenoids (3, 4) and three reported compound (1, 2, 5) were isolated. The structures of new compound 3 and 4 were determined to be 3,4-seco-4(28),6,8(14),24-mariesatetraen-26,23-olide-23-hydroxy-3-oic acid and 3,4-seco-4(28),7,24-lanostatrien-26,23-olide-23-hydroxy-3-oic acid, respectively, by spectral studies on HR-MS, (1)H-NMR, (13)C-NMR, and 2D-NMR spectra. Compound 1 was identified with pindrolactone and its structure was revised as 7,14,22Z,24-mariesatetraen-26,23-olide-3alpha-ol. Structures of 2 and 5 were determined as 7,14,24-mariesatrien-26,23-olide-3alpha,23-diol and 3alpha-hydroxy-7,14,24E-mariesatrien-23-oxo-26-oic acid. Of these compounds, 2, 3 and 4 were obtained as lactol tautomer mixtures at gamma-lactone structures of side chains.

  20. Eight pairs of epimeric triterpenoids involving a characteristic spiro-E/F ring from Abies faxoniana.

    Science.gov (United States)

    Wang, Guo-Wei; Lv, Chao; Fang, Xin; Tian, Xin-Hui; Ye, Ji; Li, Hui-Liang; Shan, Lei; Shen, Yun-Heng; Zhang, Wei-Dong

    2015-01-23

    Five pairs of new epimeric lanostane-type triterpenoids, abiespirones A-D (1-4) and G (7), two pairs of new epimeric cycloartane-type triterpenoids, abiespirones E and F (5, 6), and a pair of new epimeric 7(8→9)abeo-spirolanostane abiespirones H (8) with spiro-B/C and -E/F ring systems were isolated from Abies faxoniana as inseparable mixtures of C-23 epimers in a specific proportion. The HPLC plots showed that each purified isomer rapidly equilibrated with the C-23 epimer in solution. The structures of compounds 1-8 were elucidated by analysis of the NMR spectra and single-crystal X-ray diffraction. Compound 6 showed cytotoxicity against three hepatoma cell lines, namely, HepG2, Huh7, and SMMC7721, with IC50 values of 9.8, 7.5, and 10.7 μM, respectively, but exerted low cytotoxicity on normal QSG7701 hepatic cells, indicating its selective cytotoxicity for hepatoma cells. Compound 6 arrests the cell cycle at G2/M and induces cell apoptosis in Huh7 cells. In addition, the generation of reactive oxygen species (ROS) was detected in Huh7 cells when treated with compound 6, and a ROS scavenger partly blocked the effects of compound 6-induced Huh7 cell death, suggesting that compound 6-induced apoptosis is associated with elevated levels of ROS in Huh7 cells.

  1. 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.

  2. PHYTOCHEMICAL SCREENING AND DIURETIC ACTIVITY OF ALLIUM SATIVUM STEROIDAL AND TRITERPENOID SAPONIN FRACTION

    Directory of Open Access Journals (Sweden)

    Dr. Papiya Bigoniya et al

    2012-09-01

    Full Text Available Allium sativum L. (Liliacea is a perennial bulb with a tall, erect flowering stem. The bulb of the plant has been used in many parts of the world as a stimulant, carminative, antiseptic, expectorant, anthelmintic and diuretic. This study has been planned to assess the diuretic activity of fresh garlic bulb extract targeting the steroidal and triterpenoidal saponin content. The rats were randomly divided into 4 groups of 5 animal each as vehicle control (2 % tragacanth suspension, standard drug frusemide (20 mg/kg, p.o, and n-butanol extract (10 mg/kg and 20 mg/kg, p.o treated. Urine was collected in a graduated cylinder and its volume was measured for next 5 hr. Na+, K+ and Cl- concentrations were measured. Phytochemical analysis of A. sativum n-butanol fraction showed presence of steroids, triterpenoidal saponins and carbohydrates. At 20 mg/kg dose onset of diuresis and total volume of urine formed was significantly (P<0.01-0.05 higher. Fifth hour urine volume at 20 mg/kg dose was 9.3 ml as compared to 5.5 ml of control. Extract at 20 mg/kg dose produced 24.57% increase in Na+ excretion against 132.65% increase by frusemide when compared to control signifying natriuretic and aquaretic response. The study confirmed the ethnopharmacological and Ayurvedic use of A. sativum as a diuretic agent.

  3. Antibacterial and Synergistic Activity of Pentacyclic Triterpenoids Isolated from Alstonia scholaris.

    Science.gov (United States)

    Wang, Chao-Min; Chen, Hsiao-Ting; Wu, Zong-Yen; Jhan, Yun-Lian; Shyu, Ching-Lin; Chou, Chang-Hung

    2016-01-25

    (1) BACKGROUND: Alstonia scholaris (Apocynaceae) is an important medicinal plant that has been historically used in "Dai" ethnopharmacy to treat infectious diseases in China. Although various pharmacological activities have been reported, the antimicrobial constitutes of A. scholaris have not yet been identified. The objective of this study is to evaluate the antibacterial constitutes from the leaf extract of A. scholaris and to assess the synergistic effects of isolated compounds with antibiotics against bacterial pathogens.; (2) METHODS: The chemical constitutes isolated from the leaf extract of A. scholaris were structurally identified by NMR. The antibacterial and synergistic effect of compounds was assessed by calculating the minimal inhibitory concentration (MIC), checkerboard dilution test, and time-kill assay.; (3) RESULTS: Six pentacyclic triterpenoids were structurally identified as (1) lupeol, (2) betulin, (3) 3-hydroxy-11-ursen-28,13-olide, (4) betulinic acid, (5) oleanolic acid and (6) ursolic acid. Both oleanolic and ursolic acid showed antibacterial activity but were limited to Gram-positive bacteria. Ursolic acid showed a synergistic effect with ampicillin and tetracycline against both Bacillus cereus and S. aureus.; (4) CONCLUSION: These findings reflect that pentacyclic triterpenoids are the antibacterial chemicals in A. scholaris. The ability of ursolic acid to enhance the activity of antibiotics can constitute a valuable group of therapeutic agents in the future.

  4. Transcriptome Sequencing of Gynostemma pentaphyllum to Identify Genes and Enzymes Involved in Triterpenoid Biosynthesis

    Directory of Open Access Journals (Sweden)

    Qicong Chen

    2016-01-01

    Full Text Available G. pentaphyllum (Gynostemma pentaphyllum, a creeping herbaceous perennial with many important medicinal properties, is widely distributed in Asia. Gypenosides (triterpenoid saponins, the main effective components of G. pentaphyllum, are well studied. FPS (farnesyl pyrophosphate synthase, SS (squalene synthase, and SE (squalene epoxidase are the main enzymes involved in the synthesis of triterpenoid saponins. Considering the important medicinal functions of G. pentaphyllum, it is necessary to investigate the transcriptomic information of G. pentaphyllum to facilitate future studies of transcriptional regulation. After sequencing G. pentaphyllum, we obtained 50,654,708 unigenes. Next, we used RPKM (reads per kilobases per million reads to calculate expression of the unigenes and we performed comparison of our data to that contained in five common databases to annotate different aspects of the unigenes. Finally, we noticed that FPS, SS, and SE showed differential expression of enzymes in DESeq. Leaves showed the highest expression of FPS, SS, and SE relative to the other two tissues. Our research provides transcriptomic information of G. pentaphyllum in its natural environment and we found consistency in unigene expression, enzymes expression (FPS, SS, and SE, and the distribution of gypenosides content in G. pentaphyllum. Our results will enable future related studies of G. pentaphyllum.

  5. Transcriptome Sequencing of Gynostemma pentaphyllum to Identify Genes and Enzymes Involved in Triterpenoid Biosynthesis.

    Science.gov (United States)

    Chen, Qicong; Ma, Chengtong; Qian, Jieying; Lan, Xiuwan; Chao, Naixia; Sun, Jian; Wu, Yaosheng

    2016-01-01

    G. pentaphyllum (Gynostemma pentaphyllum), a creeping herbaceous perennial with many important medicinal properties, is widely distributed in Asia. Gypenosides (triterpenoid saponins), the main effective components of G. pentaphyllum, are well studied. FPS (farnesyl pyrophosphate synthase), SS (squalene synthase), and SE (squalene epoxidase) are the main enzymes involved in the synthesis of triterpenoid saponins. Considering the important medicinal functions of G. pentaphyllum, it is necessary to investigate the transcriptomic information of G. pentaphyllum to facilitate future studies of transcriptional regulation. After sequencing G. pentaphyllum, we obtained 50,654,708 unigenes. Next, we used RPKM (reads per kilobases per million reads) to calculate expression of the unigenes and we performed comparison of our data to that contained in five common databases to annotate different aspects of the unigenes. Finally, we noticed that FPS, SS, and SE showed differential expression of enzymes in DESeq. Leaves showed the highest expression of FPS, SS, and SE relative to the other two tissues. Our research provides transcriptomic information of G. pentaphyllum in its natural environment and we found consistency in unigene expression, enzymes expression (FPS, SS, and SE), and the distribution of gypenosides content in G. pentaphyllum. Our results will enable future related studies of G. pentaphyllum.

  6. Antibacterial properties of zeylasterone, a triterpenoid isolated from Maytenus blepharodes, against Staphylococcus aureus.

    Science.gov (United States)

    de León, L; López, M R; Moujir, L

    2010-10-20

    The anti-staphylococcal properties of zeylasterone and demethylzeylasterone, two 6-oxophenolic triterpenoids isolated from Maytenus blepharodes, were investigated. Zeylasterone was more active than demethylzeylasterone on Staphylococcus aureus cells, showing bactericidal activity at 30 μg/ml (6 × MIC) in less than three hours and bacteriostatic at lower concentrations. At the same cell density, a more drastic reduction in CFU count was obtained when the triterpenoid was incorporated into cultures growing actively. Zeylasterone at 3 × MIC added on S. aureus cultures showed an early inhibitory effect on incorporation of radiolabeled thymidine, uridina and N-acetyl-glucosamine, and later on leucine. It also caused cell membrane disruption in S. aureus, as shown by the inhibition of radiolabeled precursor uptake, rapid potassium leakage, inhibition of NADH oxidation, and formation of mesosome-like structures around the septa. The structural features of the molecule, the blockage of solute transport through the membrane and changes in its permeability, suggest that zeylasterone acts mainly on cytoplasmic membrane.

  7. Submerged fermentation production and characterization of intracellular triterpenoids from Ganoderma lucidum using HPLC-ESI-MS.

    Science.gov (United States)

    Cui, Mei-lin; Yang, Huan-yi; He, Guo-qing

    2015-12-01

    As the main bioactive metabolites of Ganoderma lucidum, triterpenoids have various pharmacological effects. In this paper, the nutritional requirements and culture conditions of a submerged culture of G. lucidum were optimized using the response surface methodology; maximum mycelia biomass and intracellular triterpenoid production reached 1.87 g/100 ml and 93.21 mg/100 ml, respectively, for a culture consisting of wort 4.10% (0.041 g/ml) and yeast extract 1.89% (0.0189 g/ml), pH 5.40. For the first time, we established that wort, which is cheap and abundant, can replace the more commonly used glucose as the sole source of carbohydrate. Using high-performance liquid chromatography-electrospray ionization-mass spectrometry (HPLC-ESI-MS), 10 major ganoderic acids were tentatively identified based on the predominant fragmentation pathways with the elimination of H2O and CO2, as well as cleavage of the D-ring.

  8. A New Triterpenoid from "Gualou-xiebai-baijiu-tang" Consisting of Fructus trichosanthis and Bulbus allii mtacrostemi

    Institute of Scientific and Technical Information of China (English)

    2002-01-01

    A new triterpenoid saponin was isolated by bioactivity-guided isolation from "Gualou-xiebai-baijiu-tang" consisting ofFructus trichosanthisi and Bulbus allii macrostemi. Its structure was determined as 3-O-β-D-galactopyranosyl-hederagenin 28-O-β-D-xylopyranosyl (1→6)- β-D-galactopyranosyl ester by means of chemical evidences and spectral analysis.

  9. A New Triterpenoid from “Gualou—xiebai—baijiu—tang” Consisting of Fructus trichosanthis and Bulbus allii macrostemi

    Institute of Scientific and Technical Information of China (English)

    XiangJiuHE; FengQIU; 等

    2002-01-01

    A new triterpenoid saponin ws isolated by bioactivity-guided isolation from “Gualou-xiebai-Baijun-tang” consisting of Fructus trichosanthisi and Bulbus allii macrostemi. Its structure was determined as 3-O-β-D-galactopyranosyl-hederagenin 28-O-β-D-xylopyranosyl (1→6)-β-D-galactopyranosyl ester by means of chemical evidences and spectral analysis.

  10. Bioengineering of plant (tri)terpenoids: from metabolic engineering of plants to synthetic biology in vivo and in vitro.

    Science.gov (United States)

    Moses, Tessa; Pollier, Jacob; Thevelein, Johan M; Goossens, Alain

    2013-10-01

    Terpenoids constitute a large and diverse class of natural products that serve many functions in nature. Most of the tens of thousands of the discovered terpenoids are synthesized by plants, where they function as primary metabolites involved in growth and development, or as secondary metabolites that optimize the interaction between the plant and its environment. Several plant terpenoids are economically important molecules that serve many applications as pharmaceuticals, pesticides, etc. Major challenges for the commercialization of plant-derived terpenoids include their low production levels in planta and the continuous demand of industry for novel molecules with new or superior biological activities. Here, we highlight several synthetic biology methods to enhance and diversify the production of plant terpenoids, with a foresight towards triterpenoid engineering, the least engineered class of bioactive terpenoids. Increased or cheaper production of valuable triterpenoids may be obtained by 'classic' metabolic engineering of plants or by heterologous production of the compounds in other plants or microbes. Novel triterpenoid structures can be generated through combinatorial biosynthesis or directed enzyme evolution approaches. In its ultimate form, synthetic biology may lead to the production of large amounts of plant triterpenoids in in vitro systems or custom-designed artificial biological systems.

  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. Immunomodulatory activity of a lupane triterpenoid ester isolated from the eastern Nigeria mistletoe,Loranthus micranthus(Linn)

    Institute of Scientific and Technical Information of China (English)

    Omeje Edwin Ogechukwu; Osadebe Patience Ogoamaka; Nworu Chukwuemeka Sylvester; Akira Kawamura; Peter Proksch

    2011-01-01

    Objective:To provide further evidence for the ethnomedicinal use of the Eastern Nigeria mistletoe,Loranthus micranthus (L. micranthus), as an immunostimulant.Methods: Solvent fractions from the crude extract of the mistletoe plant was obtained and screened by the cell mediated delayed type hypersensitivity reaction(DTHR) model in mice. Then the immunomodulatory potentials of a major lupane triterpenoid ester isolated from an active hexane fraction of the Eastern Nigeria mistletoe was investigated. Three lupeol-based triterpenoid esters:7β 15α-dihydroxyl-lup-20(29)-ene-3β-palmitate (Ⅰ), 7β, 15α-dihydroxyl-lup-20(29)-ene-3β-stearate(Ⅱ) and7β, 15α-dihydroxyl-lup-20(29)-ene-3β-decadecanoate(Ⅲ) were isolated from the plant leaves epiphyting on a local kola nut tree and were characterized. Compound 1 was subjected to cell proliferation studies usingC57Bl/6splenocytes at three dose levels (5, 25and100 μg/mL) in presence of controls. Furthermore, the effect of this compound on IL-8 receptor expression was evaluated at three doses (1, 5and10μg/mL) using the real time polymerase chain reaction assay.Results: This triterpenoid ester produced some enhancement of the splenocytes at the tested doses but at doses higher than5μg/mL caused inhibition of the IL-8 receptor expression.Conclusions:The present findings support the ethnomedicinal use of the Eastern Nigeria Mistletoe in the management of diseases affecting the immune system. The triterpenoid(s) have some immunomodulatory abilities on splenocytes andIL-8receptors and may partly account for the overall immunomodulatory activity of this plant.

  13. Novel anti-tumour barringenol-like triterpenoids from the husks of Xanthoceras sorbifolia Bunge and their three dimensional quantitative structure activity relationships analysis.

    Science.gov (United States)

    Wang, Da; Su, Dan; Yu, Bin; Chen, Chuming; Cheng, Li; Li, Xianzhe; Xi, Ronggang; Gao, Huiyuan; Wang, Xiaobo

    2017-01-01

    The high edible oil content of Xanthoceras sorbifolia Bunge seeds contributes to its economic value. In this study, we analysed the barrigenol-like triterpenoids derived from X. sorbifolia husks. We also identified anti-tumour agents that could enhance the health benefits and medicinal value of X. sorbifolia. We isolated 10 barrigenol triterpenoids, including six new compounds (1-6) and four known compounds (7-10). New compounds 3 and 5 showed significant inhibitory activity against the proliferation of three human tumour cell lines, namely, HepG2, HCT-116 and U87-MG. We determined the relationship between the structures and inhibitory activity of 25 barrigenol triterpenoids and 15 penta-cyclic triterpenoids through analysis of three-dimensional quantitative structure activity relationships (3D-QSAR). The isolation of novel barrigenol derivatives with anti-tumour activity from X. sorbifolia implied that husks of this plant may be a good source of anti-tumour agents.

  14. New ursane triterpenoids from Salvia urmiensis Bunge: Absolute configuration and anti-proliferative activity.

    Science.gov (United States)

    Farimani, Mahdi Moridi; Bahadori, Mir Babak; Koulaei, Sheyda Ahmadi; Salehi, Peyman; Ebrahimi, Samad Nejad; Khavasi, Hamid Reza; Hamburger, Matthias

    2015-10-01

    Two new triterpenoids, urmiensolide B (1) and urmiensic acid (2), with rare carbon skeletons together with three known compounds were isolated from the aerial parts of Salvia urmiensis Bunge, an endemic species of Iran. The structures were established by a combination of 1D and 2D NMR, and HRESIMS, and in the case of 2 and 3, their structures were confirmed by single-crystal X-ray analysis. The absolute configuration of 2 was established by electronic circular dichroism (ECD) spectra. The new compounds were evaluated for their anti-proliferative activities against A549 and MCF-7 human cancer cell lines. Compounds 1 and 2 showed IC50 values of 2.8 and 1.6 μM against MCF-7 cells, respectively.

  15. Triterpenoid saponin content and the expression level of some related genes in calli of Centella asiatica.

    Science.gov (United States)

    Mangas, Susana; Moyano, Elisabeth; Osuna, Lidia; Cusido, Rosa M; Bonfill, Mercedes; Palazón, Javier

    2008-10-01

    Centella asiatica has been extensively studied but there has been no report to date that relates gene expression and centelloside production in non-differentiated tissues. We have determined the content of the four principal triterpenoid bioactive compounds of C. asiatica (asiaticoside, madecassoside, asiatic acid and madecassic acid) in calli grown in different media and checked the expression level of some of the genes in the centelloside biosynthetic pathway. The results when compared with data from in vitro plant cultures showed a significantly lower expression of the gene encoding beta-amyrin synthase in calli, which is consistent with the observed lower production of centellosides (less than 900 microg/g DW), while in the plants the production was around 1.5-2 mg/g DW. Moreover, we find an efficient housekeeping gene for this plant. The biosynthesis of phytosterols is also discussed.

  16. Bioactive barrigenol type triterpenoids from the leaves of Xanthoceras sorbifolia Bunge.

    Science.gov (United States)

    Xiao, Wan; Wang, Ying; Zhang, Peng; Li, Ning; Jiang, Sheng; Wang, Jin-hui; Huang, Jian; Li, Xian

    2013-02-01

    In order to find out new natural barrigenol type triterpenenoids as antitumor agent and reveal the difference on material basis of different parts of Xanthoceras sorbifolia Bunge, the bioassay-directed separation of the saponin fraction from leaves of X. sorbifolia Bunge was carried out to afford 5 new barrigenol type triterpenoids (1-5), together with 2 known ones. The antitumor activities were evaluated and compounds 2 and 7 showed significant cytotoxic activity. Furthermore, the SAR was discussed briefly. On the basis of our research work and related literature, the difference of chemical constituents from different parts of X. sorbifolia was analyzed and concluded. The result can be a useful reference for phytochemistry taxology and safe and rational drug use of X. sorbifolia.

  17. 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.

  18. Synthesis of novel triterpenoid (lupeol) derivatives and their in vivo antihyperglycemic and antidyslipidemic activity.

    Science.gov (United States)

    Papi Reddy, K; Singh, A B; Puri, A; Srivastava, A K; Narender, T

    2009-08-01

    The triterpenoid, lupeol (1) has been isolated from the leaves extract of Aegle marmelos. Few novel derivatives (2-13) were synthesized from the naturally occurring lupeol (1) and screened for their antihyperglycemic activity (2-11) and antidyslipidemic activity (2-4 and 12-13). The derivative 4 lowered the blood glucose levels by 18.2% and 25.0% at 5h and 24h, respectively, in sucrose challenged streptozotocin induced diabetic rats (STZ-S) model at the dose of 100mg/kg body weight. The compound 4 also significantly lowered 40% (P <0.001) in triglycerides, 30% (P <0.05) in glycerol, 24% (P <0.05) in cholesterol quantity and also improved the HDL-cholesterol by 5% in dyslipidemic hamster model at the dose of 50mg/kg b.wt.

  19. In Vitro Antioxidant Activity Potential of Lantadene A, a Pentacyclic Triterpenoid of Lantana Plants

    Directory of Open Access Journals (Sweden)

    Chong Grace-Lynn

    2012-09-01

    Full Text Available Lantadenes are pentacyclic triterpenoids present in the leaves of the plant Lantana camara. In the present study, in vitro antioxidant activity and free radical scavenging capacity of lantadene A was evaluated using established in vitro models such as ferric reducing antioxidant power (FRAP, 2,2-diphenyl-1-picryl-hydrazyl (DPPH•, hydroxyl radical (OH•, nitric oxide radical (NO•, superoxide anion scavenging activities and ferrous ion chelating assay. Interestingly, lantadene A showed considerable in vitro antioxidant, free radical scavenging capacity activities in a dose dependant manner when compared with the standard antioxidant in nitric oxide scavenging, superoxide anion radical scavenging and ferrous ion chelating assay. These findings show that the lantadene A possesses antioxidant activity with different mechanism of actions towards the different free radicals tested. Since lantadene A is a very popular drug in modern medicine, it is a promising candidate for use as an antioxidant and hepatoprotective agent.

  20. Ailanthusins A-G and nor-lupane triterpenoids from Ailanthus triphysa.

    Science.gov (United States)

    Thongnest, Sanit; Boonsombat, Jutatip; Prawat, Hunsa; Mahidol, Chulabhorn; Ruchirawat, Somsak

    2017-02-01

    Bioactivity-guided chemical investigation of the CH2Cl2 and CH2Cl2MeOH extracts of the stem and stem bark material of Ailanthus tryphysa (Simaroubaceae) led to the isolation of five cycloapotirucallanes, ailanthusins A-E, two malabaricanes, ailanthusins F-G, and one nor-lupane triterpenoid, 29-nor-lup-1-ene-3,20-dione along with twenty known compounds. Their structures were elucidated through the application of extensive spectroscopic methods, and the structure of ailanthusin A was further confirmed by single crystal X-ray analysis. Several malabaricane derivatives were prepared from malabaricol and, together with some of the isolates, were evaluated for their cytotoxic activities against human cancer and normal cell lines. Copyright © 2016 Elsevier Ltd. All rights reserved.

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

    Science.gov (United States)

    Ruan, Jingya; Zheng, Chang; Qu, Lu; Liu, Yanxia; Han, Lifeng; Yu, Haiyang; Zhang, Yi; Wang, Tao

    2016-08-12

    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.

  2. 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.

  3. Anti-inflammatory properties of a triterpenoidal glycoside from Momordica cochinchinensis in LPS-stimulated macrophages.

    Science.gov (United States)

    Jung, Kiwon; Chin, Young-Won; Yoon, Kee dong; Chae, Hee-Sung; Kim, Chul Young; Yoo, Hunseung; Kim, Jinwoong

    2013-02-01

    Two triterpenoidal saponins were isolated from the seeds of Momordica cochinchinensis Sprenger (Cucurbitaceae). Identification of chemical structures has been performed by (1)H- and (13)C-NMR spectroscopy and gas chromatography (GC). One of the saponins is a new gypsogenin glycoside, named as gypsogenin 3-O-β-D-galactopyranosyl(1→2)-[α-L-rhamnopyranosyl(1→3)]-β-D-glucuronopyranoside (compound 1), which is reported for the first time from natural resources. The other saponin is a quillaic acid glycoside (compound 2), which showed anti-inflammatory activities in RAW 264.7 cells. The mechanistic understanding of anti-inflammatory activities demonstrates that compound 2 inhibits lipopolysaccharide-induced expression of nitric oxide and IL-6 via NF-κB pathway.

  4. Triterpenes and triterpenoidal glycosides from the fruits of Ilex paraguariensis (Maté

    Directory of Open Access Journals (Sweden)

    Taketa Alexandre T. C.

    2004-01-01

    Full Text Available A new triterpenoid glycoside, 3b-O-a-L-arabinopyranosyl rotundic acid, named here mateside (4, and the known triterpenes ursolic acid (1, acetylursolic acid (2, 23-hydroxyursolic acid (3, the saponins ziyu-glycoside I (5 and ilexoside II (6, were isolated from fruits of Ilex paraguariensis. Their structures were established on the basis of 1D and 2D NMR spectroscopic methods. The threshold bitterness values for mateside and ilexoside II were also determined and compared with saponins obtained from leaves of I. paraguariensis and other Ilex species. The high bitterness of Ilexoside II, one of the main saponins found the fruits, but not in the leaves of I. paraguariensis, suggests that the utilization of the fruits in the Maté production can produce a strong taste variation and unknown physiological effects.

  5. Analysis of lichen substances including triterpenoids by high performance liquid chromatography with a differential refractive index detector and a photodiode array detector

    Institute of Scientific and Technical Information of China (English)

    Hikari SATO; Kojiro HARA; Masashi KOMINE; Yoshikazu YAMAMOTO

    2011-01-01

    A new method for analysis of lichen triterpenoids was established using high performance liquid chromatography with the combination of a differential refractive index detector (RID) and a photodiode array detector (PDA).It is proved that this method was convenient to detect and identify aromatic and aliphatic lichen substances; it enabled quantitative analysis of substances having no or less absorption of ultraviolet rays such as triterpenoids.In addition,they can be measured in high accuracy compared with the TLC method.

  6. 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.

  7. Advanced ultra-performance liquid chromatography-photodiode array-quadrupole time-of-flight mass spectrometric methods for simultaneous screening and quantification of triterpenoids in Poria cocos.

    Science.gov (United States)

    Xia, Bing; Zhou, Yan; Tan, Hong Sheng; Ding, Li Sheng; Xu, Hong Xi

    2014-01-01

    A sensitive, precise and accurate method was developed to screen and quantify triterpenoids based on ultra-performance liquid chromatography-photodiode array-quadrupole time-of-flight mass spectrometry (UPLC-PDA-QTOF-MS). An exact neutral loss scan of 62.0004 Da (CH2O3) was used to selectively detect triterpenoids in Poria cocos, followed by a survey scan for exact masses of precursor and fragment ions of these triterpenoids. The developed method was applied to quantify seven major triterpenoids in 40 P. cocos samples of different origins within 18 min, and a total of 31 triterpenoids were unequivocally or tentatively identified. Principal component analysis of these samples showed a clear separation of three groups, and ten triterpenoids play key roles in differentiating these samples were obtained from the OPLS-DA variable influence on projection (VIP) plot and then unequivocally or tentatively identified. The developed method can be applied for rapid bitterness evaluation, quality control and authenticity establishment of P. cocos.

  8. Sterols and triterpenoids as potential anti-inflammatories: Molecular docking studies for binding to some enzymes involved in inflammatory pathways.

    Science.gov (United States)

    Loza-Mejía, Marco A; Salazar, Juan Rodrigo

    2015-11-01

    Triterpenes and sterols are good candidates for the development of anti-inflammatory drugs and use in chemoprevention or chemotherapy of cancer via the interaction with therapeutic targets related to inflammation, such as COX-1 and -2; LOX-5; MPO, PLA2 and i-NOS. In this study, we use molecular docking to evaluate the potential binding of a database of selected sterol and triterpenoid compounds with several skeletons against enzymes related to inflammation to propose structural requirements beneficial for anti-inflammatory activity that can be used for the design of more potent and selective anti-inflammatory and antitumor drugs. Our results suggest that the substitution pattern is important and that there is an important relationship between the class of sterol or triterpenoid skeleton and enzyme binding.

  9. New dammarane-type triterpenoids from the leaves of Panax notoginseng and their protein tyrosine phosphatase 1B inhibitory activity

    Directory of Open Access Journals (Sweden)

    Dawei Li

    2014-01-01

    Results and Conclusion: Three new dammarane-type triterpenoids, notoginsenoside-LX (1, notoginsenoside-LY (2, and notoginsenoside-FZ (3 together with eighteen known compounds were isolated from the Panax notoginseng leaves. The structure-activity relationship of the compounds with dammarane-type triterpenoids and their PTP1B inhibitory activity were also reported. Results showed that compounds 2, 15, 20, and 21 can significantly inhibit the enzyme activity of PTP1B in a dose-dependent manner, with inhibitory concentration 50 (IC50 values of 29.08 μM, 21.27 μM, 28.12 μM, and 26.59 μM, respectively. The results suggested that Panax notoginseng leaves might have potential as a new therapeutic agent for the treatment of diabetes.

  10. Studies on Triterpenoids and Flavones in Glycyrrhiza uralensis Fisch. By HPLC-ESI-MSn and FT-ICR-MSn

    Institute of Scientific and Technical Information of China (English)

    MENG Xiangyu; LI Huilin; SONG Fengrui; LIU Chunming; LIU Zhiqiang; LIU Shuying

    2009-01-01

    Seven compounds, four flavones and three triterpenoids from Glycyrrhiza uralensis Fisch. Extract are identified by high performance liquid chromatography coupled with electrospray ionization multi-tandem mass spectrometry (HPLC-ESI-MSn). The fragmentation pathways of these compounds are investigated by ESI-MSn and Fourier transform ion cyclotron resonance multiple-stage tandem mass spectrometry (FT-ICR-MSn). Comparing the reten-tion times (tR) and mass spectra with those of reference compounds, seven components are identified in Glycyrrhiza uralensis Fisch. And their MSn data proposed plausible schemes for their fragmentation. All the experimental results show that ESI-MSn and FT-ICR-MSn are powerful tools for the structural characterization of triterpenoids and fla-vones.

  11. Karakterisasi Simplisia Dan Skrining Fitokimia Serta Isolasi Steroid/Triterpenoid Dari Ekstrak Etanol Pucuk Labu Siam (Sechium edule (Jacq.) Sw.)

    OpenAIRE

    Tarziah

    2013-01-01

    One of the Cucurbitaceou plans is chayote (Sechium edule (Jacq.) Sw.). used to treat kidney stone disease, arteriosclerosis and high blood pressure that contains saponin, flavonoid, polyphenol, and steroid/triterpenoid. Simplex characterization and chemical content contained in chayote shoots are not listed in the book Materia Medika Indonesia. The purpose of this study was to determine the simplex characterization, phytochemical screening for compounds that contained in chayote shoots and is...

  12. Triterpenoid Saponin Biosynthetic Pathway Profiling and Candidate Gene Mining of the Ilex asprella Root Using RNA-Seq

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    Xiasheng Zheng

    2014-04-01

    Full Text Available Ilex asprella, which contains abundant α-amyrin type triterpenoid saponins, is an anti-influenza herbal drug widely used in south China. In this work, we first analysed the transcriptome of the I. asprella root using RNA-Seq, which provided a dataset for functional gene mining. mRNA was isolated from the total RNA of the I. asprella root and reverse-transcribed into cDNA. Then, the cDNA library was sequenced using an Illumina HiSeq™ 2000, which generated 55,028,452 clean reads. De novo assembly of these reads generated 51,865 unigenes, in which 39,269 unigenes were annotated (75.71% yield. According to the structures of the triterpenoid saponins of I. asprella, a putative biosynthetic pathway downstream of 2,3-oxidosqualene was proposed and candidate unigenes in the transcriptome data that were potentially involved in the pathway were screened using homology-based BLAST and phylogenetic analysis. Further amplification and functional analysis of these putative unigenes will provide insight into the biosynthesis of Ilex triterpenoid saponins.

  13. Anti-human immunodeficiency virus-1 protease activity of new lanostane-type triterpenoids from Ganoderma sinense.

    Science.gov (United States)

    Sato, Naoto; Zhang, Qun; Ma, Chao-Mei; Hattori, Masao

    2009-10-01

    Five new highly oxygenated lanostane-type triterpenoids [ganoderic acid GS-1 (1), ganoderic acid GS-2 (2), ganoderic acid GS-3 (3), 20(21)-dehydrolucidenic acid N (4) and 20-hydroxylucidenic acid A (5)] were isolated from the fruiting body of Ganoderma sinense, together with known compounds including 6 triterpenoids and 3 sterols. The structures of the new triterpenoids determined by spectroscopic means including 2D NMR were 7beta-hydroxy-3,11,15-trioxo-lanosta-8,24(E)-dien-26-oic acid (1), 7beta,15alpha-dihydroxy-3,11-dioxo-lanosta-8,24(E)-dien-26-oic acid (2), 12beta-acetoxy-3beta,7beta-dihydroxy-11,15-dioxo-lanosta-8,24(E)-dien-26-oic acid (3), 3beta,7beta-dihydroxy-11,15-dioxo-25,26,27-trinorlanosta-8,20-dien-24-oic acid (4), and 7beta,20xi-dihydroxy-3,11,15-trioxo-25,26,27-trinorlanost-8-en-24-oic acid (5), respectively. Among these, ganoderic acid GS-2, 20-hydroxylucidenic acid N, 20(21)-dehydrolucidenic acid N and ganoderiol F inhibited human immunodeficiency virus-1 protease with IC(50) values of 20-40 microM.

  14. Growth inhibitory, apoptotic and anti-inflammatory activities displayed by a novel modified triterpenoid, cyano enone of methyl boswellates

    Indian Academy of Sciences (India)

    Palaniyandi Ravanan; Sanjay K Singh; G S R Subba Rao; Paturu Kondaiah

    2011-06-01

    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, anti-inflammatory, prodifferentiative and anti-tumour triterpenoid compound called cyano enone of methyl boswellates (CEMB). This compound showed cytotoxic activity on a number of cancer cell lines with IC50 ranging from 0.2 to 0.6 M. CEMB inhibits DNA synthesis and induces apoptosis in A549 cell line at 0.25 M and 1 M concentrations, respectively. CEMB induces adipogenic differentiation in 3T3-L1 cells at a concentration of 0.1 M. Finally, administration of CEMB intra-tumourally significantly inhibited the growth of C6 glioma tumour xenograft in immuno-compromised mice. Collectively, these results suggest that CEMB is a very potent anti-tumour compound.

  15. Influence of triterpenoids present in apple peel on inflammatory gene expression associated with inflammatory bowel disease (IBD).

    Science.gov (United States)

    Mueller, Dolores; Triebel, Sven; Rudakovski, Olga; Richling, Elke

    2013-08-15

    Various ursanic, oleanic and lupanic pentacyclic triterpenoids found in apple peel were studied for anti-inflammatory effects in vitro using T84 colon carcinoma cells. After pretreatment with single triterpenoids, cells were stimulated with pro-inflammatory cytokines (TNF-α, INF-γ, IL-1β). Regulation of mRNA expression was analysed for three specific inflammation-associated marker genes (TNF-α, IL-8, IP-10) using qRT-PCR. Furthermore, the effects of ursolic acid (UA) and oleanolic acid (OA) on the synthesis of certain pro-inflammatory proteins were examined. IP-10 expression was inhibited in a dose-dependent manner by all the tested compounds at concentrations ≥25 μM. The mRNA expression of TNF-α was slightly affected and the IL-8 level was increased. At the protein level, UA and OA (25 μM) reduced the synthesis of IP-10; sICAM-1, IL-23 and GROα were slightly repressed. The TNF-α level was not modulated, whereas induction of IL-8 was increased. UA also enhanced the synthesis of IL-1ra, while OA suppressed the level of I-TAC. The present study confirms that triterpenoids present in apple peel and β-damascone may be implicated in the anti-inflammatory properties of apple constituents, suggesting that these substances might be helpful in the treatment of IBD as nutrient supplements.

  16. Triterpenoids isolated from the rhizomes and roots of Gentiana scabra and their inhibition of indoleamine 2,3-dioxygenase.

    Science.gov (United States)

    Li, Wei; Li, Lin Ying; Zhou, Wei; Hwang, Inkyu; Ma, Jin Yeul; Kim, Young Ho

    2015-12-01

    Gentiana scabra Bunge (Gentianaceae) is an important traditional Chinese medicine commonly used as a stomachic or appetite stimulant. In this study, 21 triterpenoids (1-21) were isolated from a methanol extract of the rhizomes and roots of G. scabra. Their structures were elucidated by comparing spectroscopic data with reported values. Among the isolated triterpenoids, scabanol (2) was firstly isolated from natural sources. All isolated compounds were evaluated for their inhibitory activity against indoleamine 2,3-dioxygenase (IDO), which catalyzes the rate limiting reaction for the conversion of tryptophan to kynurenine. Compounds 10 and 11 showed significant inhibitory activities, with IC(50) values of 12.5 and 9.5 μM, respectively. Compound 12 showed a moderate inhibitory effect, with an IC(50) value of 18.7 μM. Compounds 2 and 13 showed weaker inhibitory effects, with IC(50) values of 56.8 and 60.6 μM, respectively. Kynurenine is a potent immune modulator to suppress the functions of a variety of immune cells including T cells and natural killer cells. Given that, our results that a few selected triterpenoids inhibit IDO warrant further studies on their effects on the host immune system as natural immune stimulators.

  17. Distribution and carbon isotope patterns of diterpenoids and triterpenoids in modern temperate C3 trees and their geochemical significance

    Science.gov (United States)

    Diefendorf, Aaron F.; Freeman, Katherine H.; Wing, Scott L.

    2012-05-01

    Tricyclic diterpenoids and pentacyclic triterpenoids are nearly exclusively produced by gymnosperms and angiosperms, respectively. Even though both classes of terpenoids have long been recognized as plant biomarkers, their potential use as phylogenetically specific δ13C proxies remains largely unexplored. Little is known of how terpenoid abundance and carbon isotope composition vary either with plant phylogenetic position, functional group, or during synthesis. Here, we report terpenoid abundances and isotopic data for 44 tree species in 21 families, representing both angiosperms and gymnosperms, and both deciduous and evergreen leaf habits. Di- and triterpenoid abundances are significantly higher in evergreens compared to deciduous species, reflecting differences in growth strategies and increased chemical investment in longer-lived leaves. Carbon isotope abundances of terpenoid lipids are similar to leaf tissues, indicating biosynthetic isotope effects are small for both the MVA (-0.4‰) and MEP (-0.6‰) pathways. Leaf and molecular isotopic patterns for modern plants are consistent with observations of amber, resins and plant biomarkers in ancient sediments. The δ13C values of ancient diterpenoids are higher than triterpenoids by 2-5‰, consistent with observed isotopic differences between gymnosperms and angiosperms leaves, and support the relatively small lipid biosynthetic effects reported here. All other factors being equal, evergreen plants will dominate the abundance of terpenoids contributed to soils, sediments and ancient archives, with similar inputs estimated for angiosperm and gymnosperm trees when scaled by litter flux.

  18. Anti-vascular inflammatory effects of pentacyclic triterpenoids from Astilbe rivularis in vitro and in vivo.

    Science.gov (United States)

    Kang, Hyejin; Ku, Sae-Kwang; Kim, Jongdoo; Chung, Jiwoo; Kim, Sang Chan; Zhou, Wei; Na, MinKyun; Bae, Jong-Sup

    2017-01-05

    Sepsis is a systemic inflammatory condition resulting from bacterial infections. It is associated with high mortality rates, and its therapeutic options are limited. Transforming growth factor β induced protein (TGFBIp) is an extracellular matrix protein that functions as a mediator of experimental sepsis. C-27-carboxylated pentacyclic triterpenoids are specifically found in species of the genus Astilbe, and show several biological effects. Given the anti-inflammatory effects of pentacyclic triterpenoids, we investigated the effects of 3β-trans-p-coumaroyloxy-olean-12-en-27-oic acid (1) and 6β-hydroxy-3-oxoolean-12-en-27-oic acid (2) on TGFBIp-mediated vascular inflammatory responses. The anti-inflammatory activities of compounds 1 and 2 were determined by measuring the permeability, leukocyte adhesion and migration, and activation of pro-inflammatory proteins in TGFBIp-activated human umbilical vein endothelial cells (HUVECs) and mice. We found that compounds 1 and 2 inhibited lipopolysaccharide (LPS)-induced TGFBIp secretion, TGFBIp-induced barrier disruption, expression of cell adhesion molecules (CAMs), and the adhesion/transendothelial migration of the neutrophils to the human endothelial cells. Compounds 1 and 2 also suppressed TGFBIp-induced hyperpermeability and leukocyte migration in vivo. These results suggested that C-27-carboxylated pentacyclic triterpenoids 1 and 2 have anti-inflammatory functions by inhibiting hyperpermeability, CAM expression, and leukocyte adhesion/migration. Therefore, these compounds can be considered as a potential therapy for vascular inflammatory diseases. Copyright © 2016 Elsevier Ireland Ltd. All rights reserved.

  19. 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

  20. 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

  1. Triterpenoid Saponins from Clematis graveolens and Evaluation of their Insecticidal Activities.

    Science.gov (United States)

    Rattan, Rajeev; Reddy, S G Eswara; Dolma, Shudh Kirti; Fozdar, Bharat Inder; Gautam, Veena; Sharma, Ritika; Sharma, Upendra

    2015-09-01

    A new hederagenin based triterpenoid saponin, clematograveolenoside A (1), along with three known saponins, tomentoside A (2), huzhangoside D (3) and clematoside S (4), were isolated from the roots and rhizomes of Clematis graveolens. The structure of new compound was elucidated on the basis of detailed analysis of chemical and spectroscopic data including 1D- and 2D NMR spectra. Compound 2 was found the most effective against aphid (Aphis craccivora) with an LC50 of 1.2 and 0.5 mg/mL after treatment for 72 and 96 h, respectively and was followed by compound 4 (LC50 = 2.3 and 1.9 mg/mL) and 1 (LC50 = 3.2 and 2.6 mg/mL). In case of termite (Coptotermis homii), compound 1 was found more toxic with an LC50 of 0.1 mg/L after 24 h of treatment followed by compound 2, 3 and 4 (LC50 = 0.1, 0.2 and 0.2 mg/mL, respectively).

  2. Nanostructured lipid carrier based topical gel of Ganoderma Triterpenoids for frostbite treatment.

    Science.gov (United States)

    Shen, Cheng-Ying; Dai, Ling; Shen, Bao-De; Zhou, Xu; Bai, Jin-Xia; Xu, He; Lv, Qing-Yuan; Han, Jin; Yuan, Hai-Long

    2015-06-01

    The objective of this study was to prepare nanostructured lipid carrier (NLC)-based topical gel of Ganoderma Triterpenoids (GTs) and evaluate their effects on frostbite treatment. GT-NLCs was prepared by the high pressure homogenization method and then characterized by morphology and analyses of particle size, zeta potential, entrapment efficiency (EE), and drug loading (DL). The NLCs was suitably gelled for skin permeation studies in vitro and pharmacodynamic evaluation in vivo, compared with the GT emulgel. The GT-NLC remained within the colloidal range and was uniformly dispersed after suitably gelled by carbopol preparation. Transmission electron microscopy (TEM) study showed GT-NLCs was spherical in shape. The EE (%) and DL (%) could reach up to (81.84 ± 0.60)% and (2.13 ± 0.12)%, respectively. The result of X-ray diffractograms (XRD) showed that GTs were in an amorphous state in the NLC-gel. In vitro permeation studies through rat skin indicated that the amount of GTs permeated through skin of GT-NLCs after 24 h was higher than that of GT emulsion, and GT-NLCs increased the accumulative amounts of GTs in epidermis 7.76 times greater than GT emulsion. GT-NLC-gel was found to possess superior therapeutic effect for frostbite, compared with the GT emulgel. The NLC based topical gel of GTs could improve -their therapeutic effect for frostbite.

  3. 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.

  4. Simultaneous estimation of three triterpenoids from Carissa carandas using validated high performance liquid chromatography

    Directory of Open Access Journals (Sweden)

    Sunita Shailajan

    2012-01-01

    Full Text Available Background : Carissa carandas L. (Apocynaceae, an important fruit of tropical and subtropical arid region, has a great potential for the development of a new phytotherapeutic medicine. Due to an increase in commercial products of this fruit in the global market, an extensive phytochemical comparison seems imperative to understand its internal quality. Aims and Objective : To develop and validate an HPLC-DAD method for simultaneous estimation of three triterpenoids from C. carandas. Materials and Methods : A simple, sensitive and rapid HPLC-DAD method was developed for simultaneous estimation of lupeol, stigmasterol, and β-sitosterol from C. carandas fruits. Isocratic elution at a flow rate of 1.0 mL/min was employed on C 18 Cosmosil column with PDA detection at 210 nm using acetonitrile and ethanol. Different parts of C. carandas and its fruits collected from different geographical region were screened for lupeol, stigmasterol, and β-sitosterol contents. Results : Proposed method for simultaneous estimation of lupeol, stigmasterol and β-sitosterol was found highly specific, reliable, and sensitive which allowed good recovery of all analytes. It was validated as per ICH guidelines and proved to have good linearity, precision, repeatability, and stability. It was efficiently applied to screen different samples of C. carandas providing a mean to assess the quality and authenticity. Conclusion : The HPLC method could be an effective technique for routine analysis of lupeol, stigmasterol, and β-sitosterol simultaneously and monitoring the quality of fruit and its available products in cosmetic and pharmaceutical companies.

  5. A Natural Triterpenoid Saponin as Multifunctional Stabilizer for Drug Nanosuspension Powder.

    Science.gov (United States)

    Chen, Yingchong; Liu, Yang; Xu, Junnan; Xie, Yuanbiao; Zheng, Qin; Yue, Pengfei; Yang, Ming

    2017-03-24

    The objective of this study is to prepare a novel drug nanosuspension modified by a natural triterpenoid saponin (glycyrrhizin (GZ)) and evaluate its stability and redispersibility. A poorly soluble drug (andrographolide (AGE)) was used as a model drug. AGE nanosuspensions (AGE-NS) using GZ as natural stabilizer with mean particle size of 487 nm were firstly prepared by homogenization and converted into dried AGE nanosuspension powder (AGE-NP) by freeze-drying. It was found that GZ was able to prevent the aggregation of AGE nanocrystals and the freeze-dried AGE-NP could easily redisperse back to AGE-NS. It was related with special properties of GZ that possessed the interfacial property (37.02 ± 0.29 N/m) and electrostatic effect (-43.6 ± 0.9 mV) and could entrap AGE nanocrystals into its network structure. The freeze-dried AGE-NP/GZ exhibited excellent performance, compared with those combined with trehalose as matrix formers. The powder X-ray diffraction result demonstrated that GZ did not alter the AGE crystal state. The dissolution of AGE-NP/GZ (99.87%) was significantly enhanced, compared with the coarse AGE (42.35%). This study demonstrated that GZ could be used as a novel multifunctional stabilizer for production of drug nanosuspensions and provided a promising basis for further formulation development of poorly soluble drug.

  6. 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.

  7. Anti-inflammatory activities, triterpenoids, and diarylheptanoids of Alnus acuminata ssp. arguta.

    Science.gov (United States)

    Aguilar, María I; Rovelo, Ricardo; Verjan, Juan G; Illescas, Oscar; Baeza, Ana E; De La Fuente, Marcela; Avila, Ileana; Navarrete, Andrés

    2011-10-01

    The main use of stem bark infusions of Alnus acuminata ssp. arguta (Schlecht.) Furlow (Betulaceae) includes treatments for acute inflammation in Mexican traditional medicine. n-Hexane (CHE), chloroform (CCE), and methanol (CME) extracts of the stem bark were investigated for anti-inflammatory activity and its safety. The anti-inflammatory effects of the orally administered CME, CCE, and CHE extracts, using carrageenan-induced rat hind paw edema model, and acute oral toxicity in mice, using Lorke's method, were determined. The column chromatographic fraction (CME-3) showed a higher anti-inflammatory activity (92.2%) (IC(50): 60.8 mg/mL) as compared with CME (76.9%); both were in the same order of magnitude as that of indomethacin, the positive control drug. Safety parameters for acute oral toxicity test showed that CME was not toxic (LD(50): >5000). Several triterpenoids (1-7) from hexane extracts and diarylheptanoids (10-14) from methanol extracts of A. acuminata ssp. arguta were isolated and characterized. These results confirm the traditional uses of A. acuminata in acute inflammatory conditions and its safety for consumption.

  8. New triterpenoid saponins from cacti and anti-type I allergy activity of saponins from cactus.

    Science.gov (United States)

    Kakuta, Kazutaka; Baba, Masaki; Ito, Satoru; Kinoshita, Kaoru; Koyama, Kiyotaka; Takahashi, Kunio

    2012-07-15

    The research in our laboratory focuses on the isolation of saponins from cactus. In this study, we report five new triterpenoid saponins, dumortierinoside A methyl ester (1), pachanoside I1 (2), pachanoside D1 (3), gummososide A (4), and gummososide A methyl ester (5). Compounds 1-3 isolated from Isolatocereus dumortieri Backbg., and compounds 4 and 5 were isolated from Stenocereus alamosensis A. C. Gibson & K. E. Horak. Compound 2 possessed a new pachanane-type triterpene skeleton, pachanol I, in its aglycon. The aglycon of 3 was pachanol D, while those of 4 and 5 were both gummosogenin, which we have previously reported, but this is the first report of pachanol D and gummosogenin in their aglycon forms. Additionally, we evaluated the anti-type I allergy activity of the saponins with RBL-2H3 (Rat basophilic leukemia) cells by measuring the β-hexosaminidase release inhibitory activity. As a result of these studies, gummososide A methyl ester (5) was found to show activity (IC(50)=99.5 μM) and thurberoside A exhibited mild activity (IC(50)=166.9 μM).

  9. Hydrocarbon geochemistry of the Puget Sound region. II. Sedimentary diterpenoid, steroid and triterpenoid hydrocarbons

    Energy Technology Data Exchange (ETDEWEB)

    Barrick, R.C.; Hedges, J.I.

    1981-03-01

    Cyclic components of the aliphatic hydrocarbon mixtures extracted from Puget Sound sediment cores include a suite of C/sub 19/ and C/sub 20/ diterpenoid hydrocarbons of which fichtelite, sandaracopimaradiene, and isopimaradiene have been identified. Although apparently also derived from vascular plants, these diterpenoid hydrocarbons have relative abundances distinctly different from the co-existing plant wax n-alkane suite. Five C/sub 27/, C/sub 28/ and C/sub 29/ diasteranes and four C/sub 29/, C/sub 30/ and C/sub 31/ 17..cap alpha..(H), 21..beta..(H) hopanes occur in relatively constant proportion as components of a highly weathered fossil hydrocarbon assemblage. These chromatographically resolved cycloalkanes, along with the strongly covarying unresolved complex mixture, have been introduced to Puget Sound sediments from adjacent urban centres at increasing levels over the last 100 yr in the absence of any major oil spill. Naturally-occurring triterpenoid hydrocarbons, including hop-22(29)-ene (diploptene), are also present. A new group of C/sub 30/ polyenes has been detected which contains compounds apparently structurally related to a co-existing bicyclic C/sub 25/ diene and to C/sub 20/ and C/sub 25/ acyclic multibranched hydrocarbons described in a previous paper (Barrick et al., 1980).

  10. Hydrocarbon geochemistry of the Puget Sound region - II. Sedimentary diterpenoid, steroid and triterpenoid hydrocarbons

    Science.gov (United States)

    Barrick, Robert C.; Hedges, John I.

    1981-03-01

    Cyclic components of the 'aliphatic' hydrocarbon mixtures extracted from Puget Sound sediment cores include a suite of C 19 and C 20 diterpenoid hydrocarbons of which fichtelite. sandaracopimaradiene, and isopimaradiene have been identified. Although apparently also derived from vascular plants, these diterpenoid hydrocarbons have relative abundances distinctly different from the co-existing plant wax n-alkane suite. Five C 27, C 28 and C 29 diasteranes and four C 29, C 30 and C 31 17α(H), 21β(H) hopanes occur in relatively constant proportion as components of a highly weathered fossil hydrocarbon assemblage. These chromatographically resolved cycloalkanes. along with the strongly covarying unresolved complex mixture, have been introduced to Puget Sound sediments from adjacent urban centres at increasing levels over the last 100 yr in the absence of any major oil spill. Naturally-occurring triterpenoid hydrocarbons, including hop-22(29)-ene (diploptene), are also present. A new group of C 30 polyenes has been detected which contains compounds apparently structurally related to a co-existing bicyclic C 25 diene and to C 20 and C 25 acyclic multibranched hydrocarbons described in a previous paper ( BARRICK et al., 1980).

  11. Total triterpenoids from Ganoderma Lucidum suppresses prostate cancer cell growth by inducing growth arrest and apoptosis.

    Science.gov (United States)

    Wang, Tao; Xie, Zi-ping; Huang, Zhan-sen; Li, Hao; Wei, An-yang; Di, Jin-ming; Xiao, Heng-jun; Zhang, Zhi-gang; Cai, Liu-hong; Tao, Xin; Qi, Tao; Chen, Di-ling; Chen, Jun

    2015-10-01

    In this study, one immortalized human normal prostatic epithelial cell line (BPH) and four human prostate cancer cell lines (LNCaP, 22Rv1, PC-3, and DU-145) were treated with Ganoderma Lucidum triterpenoids (GLT) at different doses and for different time periods. Cell viability, apoptosis, and cell cycle were analyzed using flow cytometry and chemical assays. Gene expression and binding to DNA were assessed using real-time PCR and Western blotting. It was found that GLT dose-dependently inhibited prostate cancer cell growth through induction of apoptosis and cell cycle arrest at G1 phase. GLT-induced apoptosis was due to activation of Caspases-9 and -3 and turning on the downstream apoptotic events. GLT-induced cell cycle arrest (mainly G1 arrest) was due to up-regulation of p21 expression at the early time and down-regulation of cyclin-dependent kinase 4 (CDK4) and E2F1 expression at the late time. These findings demonstrate that GLT suppresses prostate cancer cell growth by inducing growth arrest and apoptosis, which might suggest that GLT or Ganoderma Lucidum could be used as a potential therapeutic drug for prostate cancer.

  12. Distinct Responses of Cytotoxic Ganoderma lucidum Triterpenoids in Human Carcinoma Cells.

    Science.gov (United States)

    Ruan, Weimei; Wei, Ying; Popovich, David G

    2015-11-01

    The medicinal mushroom Ganoderma lucidum is well recognized for its effective cancer-preventative and therapeutic properties, while specific components responsible for these anticancer effects are not well studied. Six triterpenoids that are ganolucidic acid E, lucidumol A, ganodermanontriol, 7-oxo-ganoderic acid Z, 15-hydroxy-ganoderic acid S, and ganoderic acid DM were isolated and identified from an extract of the mushroom. All compounds reduced cell growth in three human carcinoma cells (Caco-2, HepG2, and HeLa cells) dose dependently with LC50s from 20.87 to 84.36 μM. Moreover, the six compounds induced apoptosis in HeLa cells with a maximum increase (22%) of sub-G1 accumulations and 43.03% apoptotic cells in terminal deoxynucleotidyl transferase dUTP nick end labeling (TUNEL) assay (15-hydroxy-ganoderic acid S treatment). Apoptosis was further confirmed by annexin-V staining. Four of the compounds also caused apoptosis in Caco-2 cells with maximum 9.5% increase of sub-G1 accumulations (7-oxo-ganoderic acid Z treatment) and maximum 29.84% apoptotic cells in TUNEL assay (ganoderic acid DM treatment). Contrarily, none of the compounds induced apoptosis in HepG2 cells. The different responses of the three cell lines following these treatments indicated that the bioactive properties of these compounds may vary from cells of different sites of origin and are likely acting under diverse regulatory mechanisms.

  13. Pristimerin, a Triterpenoid, Inhibits Tumor Angiogenesis by Targeting VEGFR2 Activation

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    Luyong Zhang

    2012-06-01

    Full Text Available Pristimerin is a triterpenoid isolated from Celastrus and Maytenus spp. that has been shown to possess a variety of biological activities, including anti-cancer activity. However, little is known about pristimerin’s effects on tumor angiogenesis. In this study, we examined the function and the mechanism of this compound in tumor angiogenesis using multiple angiogenesis assays. We found that pristimerin significantly reduced both the volume and weight of solid tumors and decreased angiogenesis in a xenograft mouse tumor model in vivo. Pristimerin significantly inhibited the neovascularization of chicken chorioallantoic membrane (CAM in vivo and abrogated vascular endothelial growth factor (VEGF-induced microvessel sprouting in an ex vivo rat aortic ring assay. Furthermore, pristimerin inhibited the VEGF-induced proliferation, migration and capillary-like structure formation of human umbilical vascular endothelial cells (HUVECs in a concentration-dependent manner. Mechanistic studies revealed that pristimerin suppressed the VEGF-induced phosphorylation of VEGF receptor 2 kinase (KDR/Flk-1 and the activity of AKT, ERK1/2, mTOR, and ribosomal protein S6 kinase. Taken together, our results provide evidence for the first time that pristimerin potently suppresses angiogenesis by targeting VEGFR2 activation. These results provide a novel mechanism of action for pristimerin which may be important in the treatment of cancer.

  14. Src/Syk-Targeted Anti-Inflammatory Actions of Triterpenoidal Saponins from Gac (Momordica cochinchinensis) Seeds.

    Science.gov (United States)

    Yu, Jae Sik; Kim, Jun Ho; Lee, Seulah; Jung, Kiwon; Kim, Ki Hyun; Cho, Jae Youl

    2017-01-01

    Momordica cochinchinensis Spreng (family Cucurbitaceae), also known as gac, or red melon, is an edible Southeast Asian fruit valued for its nutritional and medicinal properties. Specifically, Momordicae Semen, the seeds of the gac fruit, is used in traditional Chinese medicine to treat boils, rheumatic pain, muscle spasm, hemorrhoids, and hemangiomas. In this study, a chemical investigation into a gac seed ethanol (EtOH) extract resulted in the identification of three triterpenoidal saponins (1-3), which were investigated for their anti-inflammatory effects. Among the saponins, momordica saponin I (compound 3) reduced the production of nitric oxide (NO) in LPS-activated RAW264.7 cells without inducing cytotoxicity. The mRNA levels of inducible NO synthase (iNOS) and cyclooxygenase (COX)-2 were decreased by momordica saponin I. Additionally, the translocation of p65 and p50 (subunits of the transcription factor NF-[Formula: see text]B) into the nucleus was remarkably inhibited. Furthermore, the phosphorylation levels of inflammatory signaling proteins (I[Formula: see text]B[Formula: see text], Src, and Syk) known to be upstream regulatory molecules of p65 were decreased under momordica saponin I-treated conditions. The molecular targets of momordica saponin I were confirmed in overexpression experiments and through immunoblot analyses with Src and Syk. This study provides evidence that momordica saponin I could be beneficial in treating inflammatory diseases, and should be considered a bioactive immunomodulatory agent with anti-inflammatory properties.

  15. 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.

  16. Submerged fermentation production and characterization of intracellular triterpenoids from Ganoderma lucidum using HPLC-ESI-MS

    Institute of Scientific and Technical Information of China (English)

    Mei-lin CUI; Huan-yi YANG; Guo-qing HE

    2015-01-01

    As the main bioactive metabolites of Ganoderma lucidum, triterpenoids have various pharmacological effects. In this paper, the nutritional requirements and culture conditions of a submerged culture of G. lucidum were optimized using the response surface methodology;maximum mycelia biomass and intracel ular triterpenoid produc-tion reached 1.87 g/100 ml and 93.21 mg/100 ml, respectively, for a culture consisting of wort 4.10%(0.041 g/ml) and yeast extract 1.89%(0.0189 g/ml), pH 5.40. For the first time, we established that wort, which is cheap and abundant, can replace the more commonly used glucose as the sole source of carbohydrate. Using high-performance liquid chromatography-electrospray ionization-mass spectrometry (HPLC-ESI-MS), 10 major ganoderic acids were tenta-tively identified based on the predominant fragmentation pathways with the elimination of H2O and CO2, as well as cleavage of the D-ring.%题目:利用液体发酵提高灵芝三萜产量及HPLC-ESI-MS鉴定灵芝菌丝中灵芝酸成分  目的:通过优化液体发酵培养基提高灵芝三萜产量,并对其三萜成分进行初步鉴定。  创新点:麦芽作为啤酒生产原料,含有丰富的糖类及其他营养物质,并且价格低廉,来源广泛。本文首次将麦芽汁作为碳源物质以提高灵芝三萜产量,并对其所含灵芝酸成分进行初步鉴定。  方法:以灵芝菌丝生物量和胞内三萜产量为检测指标,对其液体发酵培养基中的碳(C)源和氮(N)源进行筛选,并利用单因素实验确定其相应浓度,再经响应面法优化液体发酵培养基(C源、N源、pH)(表1)。另一方面,酸碱转化法纯化灵芝三萜提取物后,利用高效液相色谱-电喷雾-质谱(HPLC-ESI-MS)法初步鉴定灵芝所含灵芝酸成分(表2)。  结论:本实验响应面结果显示:当培养基含麦芽汁4.1%,酵母浸出粉1.89%,pH为5.40时,灵芝液体发酵菌丝生物

  17. Kadcoccitones A and B, two new 6/6/5/5-fused tetracyclic triterpenoids from Kadsura coccinea.

    Science.gov (United States)

    Liang, Cheng-Qin; Shi, Yi-Ming; Luo, Rong-Hua; Li, Xing-Yao; Gao, Zhong-Hua; Li, Xiao-Nian; Yang, Liu-Meng; Shang, Shan-Zhai; Li, Yan; Zheng, Yong-Tang; Zhang, Hong-Bin; Xiao, Wei-Lie; Sun, Han-Dong

    2012-12-21

    A pair of new triterpenoid epimers, kadcoccitones A (1) and B (2), together with a new biogenetically related compound kadcoccitone C (3), were isolated from Kadsura coccinea. The epimers featured an unprecedented carbon skeleton with a 6/6/5/5-fused tetracyclic ring system unit and a C(9) side chain. Their structures were determined by spectroscopic data, ECD calculation, and single-crystal X-ray diffraction. Compounds 1 and 3 showed anti-HIV-1 activity with an EC(50) value of 47.91 and 32.66 μg/mL, respectively.

  18. Two New Tirucallane-Type Triterpenoids from the Stem Barks of Aphanamixis grandifolia and Their Cytotoxic Activities

    Institute of Scientific and Technical Information of China (English)

    张耀; 汪俊松; 王朋然; 孔令义

    2012-01-01

    Two new tirucallane-type triterpenoids, 3a,24β',25-trihydroxy-21,21-dimethoxy-23-oxo-tirucall-7-ene (I) and 3a-acetoxy-21fl-methoxy-24,25,26,27-tetranortirucall-7-ene-23(21)-lactone (2), were isolated from the stem barks ofAphanamixis grandifblia, and their structures were elucidated on the basis of spectroscopic data analysis includ- ing ID, 2D NMR, IR, and ESI-MS spectral methods. The two isolates were evaluated for their cytotoxicities using NCI-H460 and HeLa cell lines.

  19. Triterpenoids and Steroids from Ganoderma mastoporum and Their Inhibitory Effects on Superoxide Anion Generation and Elastase Release

    Directory of Open Access Journals (Sweden)

    Tran Dinh Thang

    2013-11-01

    Full Text Available The methanol extracts of the fruiting bodies of Ganoderma mastoporum collected in Vietnam was purified to afford eight compounds, including three triterpenoids and five steroids. The purified compounds were examined for their inhibitory effects against superoxide anion generation and elastase release. Among the tested compounds, ergosta-4,6,8(14,22-tetraen-3-one (3 exhibited the most significant inhibition towards superoxide anion generation and elastase release with IC50 values of 2.30 ± 0.38 and 1.94 ± 0.50 µg/mL, respectively.

  20. Transcriptional profiles of the response of methicillin-resistant Staphylococcus aureus to pentacyclic triterpenoids.

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    Pooi Yin Chung

    Full Text Available Staphylococcus aureus is an important human pathogen in both hospital and the community that has demonstrated resistance to all currently available antibiotics over the last two decades. Multidrug-resistant isolates of methicillin-resistant S. aureus (MRSA exhibiting decreased susceptibilities to glycopeptides has also emerged, representing a crucial challenge for antimicrobial therapy and infection control. The availability of complete whole-genome nucleotide sequence data of various strains of S. aureus presents an opportunity to explore novel compounds and their targets to address the challenges presented by antimicrobial drug resistance in this organism. Study compounds α-amyrin [3β-hydroxy-urs-12-en-3-ol (AM], betulinic acid [3β-hydroxy-20(29-lupaene-28-oic acid (BA] and betulinaldehyde [3β-hydroxy-20(29-lupen-28-al (BE] belong to pentacyclic triterpenoids and were reported to exhibit antimicrobial activities against bacteria and fungi, including S. aureus. The MIC values of these compounds against a reference strain of methicillin-resistant S. aureus (MRSA (ATCC 43300 ranged from 64 µg/ml to 512 µg/ml. However, the response mechanisms of S. aureus to these compounds are still poorly understood. The transcription profile of reference strain of MRSA treated with sub-inhibitory concentrations of the three compounds was determined using Affymetrix GeneChips. The findings showed that these compounds regulate multiple desirable targets in cell division, two-component system, ABC transporters, fatty acid biosynthesis, peptidoglycan biosynthesis, aminoacyl-tRNA synthetase, ribosome and β-lactam resistance pathways which could be further explored in the development of therapeutic agents for the treatment of S. aureus infections.

  1. Macromolecular interactions of triterpenoids and targeted toxins: role of saponins charge.

    Science.gov (United States)

    Thakur, Mayank; Weng, Alexander; Pieper, Alexandra; Mergel, Katharina; von Mallinckrodt, Benedicta; Gilabert-Oriol, Roger; Görick, Cornelia; Wiesner, Burkhard; Eichhorst, Jenny; Melzig, Matthias F; Fuchs, Hendrik

    2013-10-01

    Macromolecular interaction of protein toxins with certain plant triterpenoids holds potential for application in tumor therapy. The ability of only certain saponins to enhance the endosomal escape of toxins specifically in tumor cells was evaluated and set into correlation with the electrophoretic mobility. Saponins from Saponaria officinalis Linn, were selected as a lead to understand this evolutionarily conserved principle in detail. Agarose gel electrophoresis was utilized to procure pure saponin fractions with different electrophoretic mobility, which were tested for their ability to enhance the toxicity by live cell monitoring. Five fractions (SOG1-SOG5) were isolated with a relative electrophoretic mobility of (-0.05, 0.41, 0.59, 0.75 and 1.00) and evaluated using thin layer chromatography, HPLC, and mass spectroscopic analysis. Cytotoxicity experiments revealed highest effectiveness with SOG3. Live cell imaging experiments with SOG3 revealed that this saponin with a specific REM of 0.59 could assist in the lyso/endosomal release of the toxic payload without affecting the integrity of plasma membrane and could lead to the induction of apoptosis. This charge dependent enhancement was also found to be highly specific to type I ribosome inactivating proteins compared to bacterial toxins. Charge interaction of plant toxins and saponins with tumor cells, plays a major role in toxin specific modulation of response. The finding opens up newer ways of finding protein saponin interaction conserved evolutionarily and to test their role in endosomal escape of therapeutic molecules. Copyright © 2013 Elsevier B.V. All rights reserved.

  2. RTA 408, A Novel Synthetic Triterpenoid with Broad Anticancer and Anti-Inflammatory Activity.

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    Brandon L Probst

    Full Text Available Semi-synthetic triterpenoids are antioxidant inflammation modulator (AIM compounds that inhibit tumor cell growth and metastasis. Compounds in the AIM class bind to Keap1 and attenuate Nrf2 degradation. In the nucleus, Nrf2 increases antioxidant gene expression and reduces pro-inflammatory gene expression. By increasing Nrf2 activity, AIMs reduce reactive oxygen species and inflammation in the tumor microenvironment, which reverses tumor-mediated immune evasion and inhibits tumor growth and metastasis. AIMs also directly inhibit tumor cell growth by modulating oncogenic signaling pathways, such as IKKβ/NF-κB. Here, we characterized the in vitro antioxidant, anti-inflammatory, and anticancer activities of RTA 408, a novel AIM that is currently being evaluated in patients with advanced malignancies. At low concentrations (≤ 25 nM, RTA 408 activated Nrf2 and suppressed nitric oxide and pro-inflammatory cytokine levels in interferon-γ-stimulated RAW 264.7 macrophage cells. At higher concentrations, RTA 408 inhibited tumor cell growth (GI50 = 260 ± 74 nM and increased caspase activity in tumor cell lines, but not in normal primary human cells. Consistent with the direct effect of AIMs on IKKβ, RTA 408 inhibited NF-κB signaling and decreased cyclin D1 levels at the same concentrations that inhibited cell growth and induced apoptosis. RTA 408 also increased CDKN1A (p21 levels and JNK phosphorylation. The in vitro activity profile of RTA 408 is similar to that of bardoxolone methyl, which was well-tolerated by patients at doses that demonstrated target engagement. Taken together, these data support clinical evaluation of RTA 408 for cancer treatment.

  3. RTA 408, A Novel Synthetic Triterpenoid with Broad Anticancer and Anti-Inflammatory Activity.

    Science.gov (United States)

    Probst, Brandon L; Trevino, Isaac; McCauley, Lyndsey; Bumeister, Ron; Dulubova, Irina; Wigley, W Christian; Ferguson, Deborah A

    2015-01-01

    Semi-synthetic triterpenoids are antioxidant inflammation modulator (AIM) compounds that inhibit tumor cell growth and metastasis. Compounds in the AIM class bind to Keap1 and attenuate Nrf2 degradation. In the nucleus, Nrf2 increases antioxidant gene expression and reduces pro-inflammatory gene expression. By increasing Nrf2 activity, AIMs reduce reactive oxygen species and inflammation in the tumor microenvironment, which reverses tumor-mediated immune evasion and inhibits tumor growth and metastasis. AIMs also directly inhibit tumor cell growth by modulating oncogenic signaling pathways, such as IKKβ/NF-κB. Here, we characterized the in vitro antioxidant, anti-inflammatory, and anticancer activities of RTA 408, a novel AIM that is currently being evaluated in patients with advanced malignancies. At low concentrations (≤ 25 nM), RTA 408 activated Nrf2 and suppressed nitric oxide and pro-inflammatory cytokine levels in interferon-γ-stimulated RAW 264.7 macrophage cells. At higher concentrations, RTA 408 inhibited tumor cell growth (GI50 = 260 ± 74 nM) and increased caspase activity in tumor cell lines, but not in normal primary human cells. Consistent with the direct effect of AIMs on IKKβ, RTA 408 inhibited NF-κB signaling and decreased cyclin D1 levels at the same concentrations that inhibited cell growth and induced apoptosis. RTA 408 also increased CDKN1A (p21) levels and JNK phosphorylation. The in vitro activity profile of RTA 408 is similar to that of bardoxolone methyl, which was well-tolerated by patients at doses that demonstrated target engagement. Taken together, these data support clinical evaluation of RTA 408 for cancer treatment.

  4. Triterpenoids from Momordica balsamina: Reversal of ABCB1-mediated multidrug resistance.

    Science.gov (United States)

    Ramalhete, Cátia; Mulhovo, Silva; Molnar, Joseph; Ferreira, Maria-José U

    2016-11-01

    The ability as P-glycoprotein (P-gp, ABCB1) modulators of thirty (1-30) triterpenoids of the cucurbitane-type was evaluated on human L5178 mouse T-lymphoma cell line transfected with the human MDR1 gene, through the rhodamine-123 exclusion assay. Compounds (1-26, and 29, 30) were previously obtained from the African medicinal plant Momordica balsamina, through both isolation (1-15) and molecular derivatization (16-26 and 29, 30). Compounds 27-28 are two new karavilagenin C (34) derivatives having succinic acid moieties. Apart from 4, 6, 8, 10 and 11, most of the isolated compounds (1-15) displayed strong MDR reversing activity in a dose-dependent mode, exhibiting a many-fold activity when compared with verapamil, used as positive control. At the lowest concentration tested, compounds 2 and 7 were the most active. However, a decrease of activity was found for the acyl derivatives (16-30). In a chemosensitivity assay, the MDR reversing activity of some of the most active compounds (1-3, 5, 7, 12-15) was further assessed on the same cell model. All the tested compounds, excepting 15, corroborated the results of the transport assay, revealing to synergistically interact with doxorubicin. Structure-activity relationship studies, taking into account previous results, showed that different substitution patterns, at both the tetracyclic nucleus and the side chain, play important role in ABCB1 reversal activity. An optimal lipophilicity was also recognized. Copyright © 2016 Elsevier Ltd. All rights reserved.

  5. 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.

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

    Directory of Open Access Journals (Sweden)

    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.

  7. 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.

  8. Antileishmanial activity of semisynthetic lupane triterpenoids betulin and betulinic acid derivatives: synergistic effects with miltefosine.

    Directory of Open Access Journals (Sweden)

    Maria C Sousa

    Full Text Available Leishmaniasis is a neglected tropical disease (NTDs, endemic in 88 countries, affecting more than 12 million people. The treatment consists in pentavalent antimony compounds, amphotericin B, pentamidine and miltefosine, among others. However, these current drugs are limited due to their toxicity, development of biological resistance, length of treatment and high cost. Thus, it is important to continue the search for new effective and less toxic treatments. The anti-Leishmania activity of sixteen semisynthetic lupane triterpenoids derivatives of betulin (BT01 to BT09 and betulinic acid (AB10 to AB16 were evaluated. Drug interactions between the active compounds and one current antileishmanial drug, miltefosine, were assessed using the fixed ratio isobologram method. In addition, effects on the cell cycle, apoptosis/necrosis events, morphology and DNA integrity were studied. The derivatives BT06 (3β-Hydroxy-(20R-lupan-29-oxo-28-yl-1H-imidazole-1-carboxylate and AB13 (28-(1H-imidazole-1-yl-3,28-dioxo-lup-1,20(29-dien-2-yl-1H-imidazole-1-carboxylate were found to be the most active, with IC50 values of 50.8 µM and 25.8 µM, respectively. Interactions between these two compounds and miltefosine were classified as synergistic, with the most effective association being between AB13 and miltefosine, where decreases of IC50 values to 6 µM were observed, similar to the miltefosine activity alone. AB13 induced significant morphological changes, while both derivatives produced anti-proliferative activity through cell cycle arrest at the G0/G1 phase. Neither of these derivatives induced significant apoptosis/necrosis, as indicated by phosphatidylserine externalization and DNA fragmentation assays. In addition, neither of the derivatives induced death in macrophage cell lines. Thus, they do not present any potential risk of toxicity for the host cells. This study has identified the betulin derivative BT06 and the betulinic acid derivative AB13 as promising

  9. Antiplasmodial and Cytotoxic Triterpenoids from the Bark of the Cameroonian Medicinal Plant Entandrophragma congoënse.

    Science.gov (United States)

    Happi, Gervais Mouthé; Kouam, Simeon Fogue; Talontsi, Ferdinand Mouafo; Lamshöft, Marc; Zühlke, Sebastian; Bauer, Jonathan O; Strohmann, Carsten; Spiteller, Michael

    2015-04-24

    Eight new triterpenoids, prototiamins A-G (1-6, 9) and seco-tiaminic acid A (10), were isolated along with four known compounds from the bark of Entandrophragma congoënse. Their structures were elucidated by means of HRMS and different NMR techniques and chemical transformations. Assignments of relative and absolute configurations for the new compounds were achieved using NOESY experiments and by chemical modification including the advanced Mosher's method. Additionally, the structure and relative configuration of compound 3 were confirmed by single-crystal X-ray diffraction analysis. Compounds 1, 3, and 5 displayed significant in vitro antiplasmodial activity against the erythrocytic stages of chloroquine-sensitive Plasmodium falciparum strain NF54. Prototiamin C (3) was the most potent of the compounds isolated, with an IC50 value of 0.44 μM. All compounds tested showed low cytotoxicity for the L6 rat skeletal myoblast cell line.

  10. Triterpenoidal alkaloids from Buxus hyrcana and their enzyme inhibitory, anti-fungal and anti-leishmanial activities.

    Science.gov (United States)

    Ata, Athar; Iverson, Chad D; Kalhari, Kosmulalage S; Akhter, Sarfraz; Betteridge, Jordan; Meshkatalsadat, Mohammad Hadi; Orhan, Ilkay; Sener, Bilge

    2010-10-01

    From the aerial parts of Buxus hyrcana, three triterpenoidal alkaloids, 17-oxo-3-benzoylbuxadine (1), buxhyrcamine (2), and 31-demethylcyclobuxoviridine (3), along with 16 known compounds, cyclobuxoviridine (4), N(b)-dimethylcyclobuxoviricine (5), E-buxenone (6), Z-buxenone (7), moenjodaramine (8), homomoenjodarmine (9), buxamine A (10), buxamine B (11), 31-hydroxybuxamine B (12), N(20)-formylbuxaminol E (13), papillozine C (14), buxmicrophylline F (15), buxrugulosamine (16), cyclobuxophylline O (17), spirofornabuxine (18) and arbora-1,9(11)-dien-3-one (19) were isolated. Their structures were elucidated by using NMR spectroscopic methods. All of the compounds exhibited moderate to weak acetylcholinesterase, butyrylcholinesterase and glutathione S-transferase inhibitory activities. Compounds 1-19 also exhibited modest anti-fungal activities against Candidaalbicans. Compounds 1, 2, 8, 9 and 18 also exhibited weak anti-leishmanial activity.

  11. Triterpenoid Saponins from Cortex Albiziae%合欢皮中的三萜皂苷

    Institute of Scientific and Technical Information of China (English)

    邹坤; 赵玉英; 张如意

    2008-01-01

    Cortex Albiziae, the dried stem bark of a leguminous plant, Albizia julibrissin Durazz, was specified in Chinese Pharmacopoeia (1995 edit.) as a traditional Chinese medicine to be used to relieve melancholia and uneasiness of body and mind, to invigorate the circulation of blood and subside a swelling. In a course of our quality assessment of traditional Chinese medicines, the n-BuOH soluble part of 95% EtOH extracts from the stem barks of Albizia julibrissin was subjected to a series of solvent treatment and chromatographic separations, including Rp-HPLC methods, giving rise to 28 pentacyclic triterpenoid saponins. Based on chemical methods and spectroscopic evidences, the structures of saponins were identified, which included six pairs of diastereoisomers, five pairs of position isomers, and 26 of them were new compounds. All the saponins are trisdesmosidic saponins, which are composed of an acacic acid moiety, 7-9 monosaccharide moieties, 1-2 monoterpenic acid moieties, and exhibited their molecular ion peaks around m/z 2 000. Their carbon-13 signals and most of proton signals were assigned based on 1D and 2D NMR experiments. The proton and carbon signals of several known saponins were revised and reassigned. The spectroscopic properties related to these saponins were analyzed and summarized. The cytotoxic activity and other activities of these saponins and their analogues were discussed also.%合欢皮作为传统中药,为豆科植物合欢的干燥茎皮.在1995年版中国药典中记载合欢皮具有解郁安神、活血化瘀的作用.在我们对传统中药品质进行研究的过程中,通过对合欢皮95%乙醇提取物的正丁醇可溶部位进行一系列溶剂处理和层析分离,分离获得28个五环三萜皂苷.基于化学和波谱证据,我们鉴定了它们的结构,包括6对非对映异构体、5对位置异构体,其中26个皂苷为新化合物.所有分离皂苷均为三糖链皂苷,含有金合欢酸皂苷元,7~9个单糖和1~2

  12. Inhibition of botulinum toxin's association with rat brain synaptosomes by toosendanin,an antibotulismic triterpenoid

    Institute of Scientific and Technical Information of China (English)

    Jianying Zhou; Yuliang Shi

    2006-01-01

    BACKGROUND:Toosendanin(TSN),a triterpenoid derivative extracted from the bark of Melia toosendanin Sieb et Zucc,has been demonstrated to be an effective drug for treatment of experimental botulism.OBJECTIVE:To explore its antibotulismic mechanism by observing the effect of toosendanin on association of botulinum toxin(BoTx)with rat brain synaptosomes under different conditions.DESIGN:A randomized controlled experiment.SETTING:Shanghai Institutes for Biological Sciences,Chinese Academy of Sciences.MATERIALS:Sprague-Dawley rats,weighing(220±12)g,were involved.TSN was a sample recrystallized in ethanol with a purity>98%.BoTx/A and BoTx/C of 500 ku(1.8x107mouse LD50/mg)were purchased from Wako(Japan),Horse antitoxins to BoTx/A and/C(pdmary antibodies)were purchased from Lanzhou Institute of Biological Products(China).METHODS:Major experiments were finished between March 2005 and October 2005 in key laboratory of neurobiology,Shanghai Institutes for Biological Sciences,Chinese Academy of Sciences.①Preparation of synaptosome of rats:one aliquot of synaptosome was pre-incubated with TSN(17μmol/L)for 20 minutes at 4℃or 37℃(another aliquot of synaptosome which was untouched was used as control).Then,BoTx was respectively added for another 20-minute incubation.②A homochronous experiment was still Derformed at 37℃.Differently,high level of K+ was used to stimulate synaptosome for 25 minutee.Two aliquots of synaptosomes with or without TSN(17 μmol/L)were preincubated for 15 minutes.Then,30 mmol/L KCl was separately added in two aliquots,5 minutes later,13 nmol/L BoTx/C was separately added followed by 20-minute incubation.[3]The effect of TSN on BoTx binding was observed by Western blot and synchronization method.③ttest was used for comparing the difference of measurement data.MAIN OUTCOME MEASURES:The gray value of BoTx bands from westem blot was used to estimate the bound amount of BoTx.RESULTS:①Preincubation of synaptosomes with TSN(17 μmol/L)at 4

  13. Epigenetic modifications of triterpenoid ursolic acid in activating Nrf2 and blocking cellular transformation of mouse epidermal cells.

    Science.gov (United States)

    Kim, Hyuck; Ramirez, Christina N; Su, Zheng-Yuan; Kong, Ah-Ng Tony

    2016-07-01

    Ursolic acid (UA), a well-known natural triterpenoid found in abundance in blueberries, cranberries and apple peels, has been reported to possess many beneficial health effects. These effects include anticancer activity in various cancers, such as skin cancer. Skin cancer is the most common cancer in the world. Nuclear factor E2-related factor 2 (Nrf2) is a master regulator of antioxidative stress response with anticarcinogenic activity against UV- and chemical-induced tumor formation in the skin. Recent studies show that epigenetic modifications of Nrf2 play an important role in cancer prevention. However, the epigenetic impact of UA on Nrf2 signaling remains poorly understood in skin cancer. In this study, we investigated the epigenetic effects of UA on mouse epidermal JB6 P+ cells. UA inhibited cellular transformation by 12-O-tetradecanoylphorbol-13-acetate at a concentration at which the cytotoxicity was no more than 25%. Under this condition, UA induced the expression of the Nrf2-mediated detoxifying/antioxidant enzymes heme oxygenase-1, NAD(P)H:quinone oxidoreductase 1 and UDP-glucuronosyltransferase 1A1. DNA methylation analysis revealed that UA demethylated the first 15 CpG sites of the Nrf2 promoter region, which correlated with the reexpression of Nrf2. Furthermore, UA reduced the expression of epigenetic modifying enzymes, including the DNA methyltransferases DNMT1 and DNMT3a and the histone deacetylases (HDACs) HDAC1, HDAC2, HDAC3 and HDAC8 (Class I) and HDAC6 and HDAC7 (Class II), and HDAC activity. Taken together, these results suggest that the epigenetic effects of the triterpenoid UA could potentially contribute to its beneficial effects, including the prevention of skin cancer.

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

    Directory of Open Access Journals (Sweden)

    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.

  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. Characterization of triterpenoid profiles and triterpene synthase expression in the leaves of eight Vitis vinifera cultivars grown in the Upper Rhine Valley.

    Science.gov (United States)

    Pensec, Flora; Szakiel, Anna; Pączkowski, Cezary; Woźniak, Agnieszka; Grabarczyk, Marta; Bertsch, Christophe; Fischer, Marc J C; Chong, Julie

    2016-05-01

    Plant triterpenoids are a diverse group of secondary metabolites with wide distribution, high chemical diversity and interesting pharmacological and antimicrobial properties. The first step in the biosynthesis of all triterpenoids is the cyclization of the 2,3-oxidosqualene precursor, catalyzed by oxidosqualene cyclases (OSCs), which have characteristic product specificities. Biosynthesis and functions of pentacyclic triterpenes have been poorly studied in grapevine. In this study, we first investigated the profile of triterpenoids present in leaf cuticular waxes from eight Vitis vinifera cultivars cultivated in the Upper Rhine Valley. Further quantification of triterpenoids showed that these cultivars can be divided into two groups, characterized by high levels of lupeol (e.g., Pinot noir) or taraxerol (e.g., Gewurztraminer) respectively. We further analyzed the OSC family involved in the synthesis of pentacyclic triterpenes (called VvTTPSs) in the sequenced V. vinifera 40024 genome and found nine genes with similarity to previously characterized triterpene synthases. Phylogenetic analysis further showed that VvTTPS1-VvTTPS3 and VvTTPS5-VvTTPS9 belong to the β-amyrin synthase and multifunctional triterpene synthase clade, whereas VvTTPS10 belongs to the lupeol synthase clade. We studied the expression of several members of the VvTTPS family following biotic and abiotic stresses in V. vinifera 40024 as well as in the eight healthy cultivars. This study further revealed that one candidate gene, VvTTPS5, which does not belong to the lupeol synthase clade, is highly expressed in lupeol-rich cultivars. VvTTPS3, VvTTPS5, VvTTPS6, VvTTPS7 and VvTTPS10 were highly upregulated by UV stress, but only VvTTPS3, VvTTPS5, VvTTPS6 and VvTTPS10 were upregulated following downy mildew and gray mold infections respectively. These results suggest differential roles of VvTTPS against environmental stresses in grape leaves.

  17. Simultaneous estimation of three triterpenoids-ursolic acid, β-sitosterol and lupeol from flowers, leaves and formulations of Rhododendron arboreum Smith. using validated HPTLC method

    OpenAIRE

    Sunita Shilajan; Gauri Swar

    2013-01-01

    Background: This paper enfolds a rapid and sensitive high-performance thin-layer chromatographic (HPTLC) method for the simultaneous estimation of three triterpenoids namely ursolic acid, β-sitosterol and lupeol from the leaves, flowers and herbal formulations of Rhododendron arboreum Smith., an ethnomedicinal Himalayan tree. All the three phytoconstituents have high therapeutic value. Aims and Objectives: The main aim is to separate, resolve and simultaneously quantitate the three markers-ur...

  18. Major triterpenoids in Chinese hawthorn "Crataegus pinnatifida" and their effects on cell proliferation and apoptosis induction in MDA-MB-231 cancer cells.

    Science.gov (United States)

    Wen, Lingrong; Guo, Ruixue; You, Lijun; Abbasi, Arshad Mehmood; Li, Tong; Fu, Xiong; Liu, Rui Hai

    2017-02-01

    The cytotoxicity and antiproliferative effect of phytochemicals presenting in the fruits of Chinese hawthorn (Crataegus pinnatifida) were evaluated. Shanlihong (Crataegus pinnatifida Bge. var. major N.E.Br.) variety possessed significant levels of flavonoids and triterpenoids, and showed potent antiproliferative effect against HepG2, MCF-7 and MDA-MB- 231 human cancer cells lines. Triterpenoids-enriched fraction (S9) prepared by Semi-preparative HPLC, and its predominant ingredient ursolic acid (UA) demonstrated remarkably antiproliferative activities for all the tested cancer cell lines. DNA flow cytometric analysis showed that S9 fraction and UA significantly induced G1 arrest in MDA-MB-231 cells in a dose-dependent manner. Western blotting analysis revealed that S9 fraction and UA significantly induced PCNA, CDK4, and Cyclin D1 downregulation in MDA-MB-231 cells, followed by p21(Waf1/Cip1) up-regulation. Additionally, flow cytometer and DNA ladder assays indicated that S9 fraction and UA significantly induced MDA-MB-231 cells apoptosis. Mitochondrial death pathway was involved in this apoptosis as significantly induced caspase-9 and caspase-3 activation. These results suggested that triterpenoids-enriched fraction and UA exhibited antiproliferative activity through the cell cycle arrest and apoptosis induction, and was majorly responsible for the potent anticancer activity of Chinese hawthorn. Copyright © 2016 Elsevier Ltd. All rights reserved.

  19. 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.

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

    Directory of Open Access Journals (Sweden)

    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.

  1. Bioassay-Guided Isolation of Cytotoxic Cycloartane Triterpenoid Glycosides from the Traditionally Used Medicinal Plant Leea indica

    Directory of Open Access Journals (Sweden)

    Yau Hsiung Wong

    2012-01-01

    Full Text Available Leea indica is a medicinal plant used traditionally to cure cancer. In this study, the cytotoxic compounds of L. indica were isolated using bioassay-guided approach. Two cycloartane triterpenoid glycosides, mollic acid arabinoside (MAA and mollic acid xyloside (MAX, were firstly isolated from L. indica. They inhibited the growth of Ca Ski cervical cancer cells with IC50 of 19.21 μM (MAA and 33.33 μM (MAX. MRC5 normal cell line was used to calculate selectivity index. MAA and MAX were about 8 and 4 times more cytotoxic to Ca Ski cells compared to MRC5. The cytotoxicity of MAA was characterized by both cytostatic and cytocidal effects. MAA decreased the expression of proliferative cell nuclear antigen, increased sub-G1 cells, and arrested cells in S and G2/M phases. This study provides the evidence for the ethnomedicinal use of L. indica and paves the way for future mechanism studies on the anticancer effects of MAA.

  2. Glycyrrhizic acid (GA), a triterpenoid saponin glycoside alleviates ultraviolet-B irradiation-induced photoaging in human dermal fibroblasts.

    Science.gov (United States)

    Afnan, Quadri; Adil, Mushtaq Dar; Nissar-Ul, Ashraf; Rafiq, Ahmad Rather; Amir, Hussian Faridi; Kaiser, Peerzada; Gupta, Vijay Kumar; Vishwakarma, Ram; Tasduq, Sheikh Abdullah

    2012-05-15

    Glycyrrhizic acid (GA), a triterpenoid saponin glycoside from the roots and rhizomes of licorice is used in traditional and modern medicine for the treatment of numerous medical conditions including skin diseases and beauty care product. In the present study, we investigated the effect of GA against ultraviolet B (UVB) irradiation-induced photoaging in human dermal fibroblasts (HDFs) and its possible mechanism of action. HDFs were subjected to photoaging by sub-toxic dose of UVB (10 mj/cm(2)) irradiation. Cell viability, matrix metalloproteinase 1 (MMP1), pro-collagen 1, cellular and nuclear morphology, cell cycle, intracellular reactive oxygen species (ROS), caspase 3 and hyaluronidase inhibition assays were performed. Western blotting was used to evaluate the expression of NF-kappa B (NF-κB) and cytochrome-C proteins. GA treatment significantly inhibited photoaging. It achieved this by reducing ROS, NF-κB, cytochrome c, caspase 3 levels and inhibiting hyaluronidase enzyme. The main mechanism seems to be, most likely by blocking MMP1 activation by modulating NF-κB signaling. These findings may be useful for development of natural and safe photoprotective agents against UVB irradiation. Copyright © 2012 Elsevier GmbH. All rights reserved.

  3. Metabolomic Analysis of Methyl Jasmonate-Induced Triterpenoid Production in the Medicinal Herb Centella asiatica (L. Urban

    Directory of Open Access Journals (Sweden)

    Ian A. Dubery

    2013-04-01

    Full Text Available Centella asiatica is an important source of biologically active pentacyclic triterpenoids. The enhancement of the biosynthesis of the centellosides by manipulation of associated metabolic pathways is receiving much attention. Jasmonates play critical roles in plant metabolism by up-regulating the expression of genes related to secondary metabolites. Here, we investigated the effect of methyl jasmonate (MeJa in C. asiatica through targeted metabolomic profiling of asiaticoside and madecassoside 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 qualitatively and quantitatively. Principal component analysis (PCA-derived scores plots revealed clusters of sample replicates for control and treated samples at 2, 4 and 6 days while loading plots aided in identifying signatory biomarkers (asiatic acid and madecassic acid, as well as asiaticoside and madecassoside that clearly demonstrate the variability between samples. In addition to increased biosynthesis of the targeted centelloids, other differential changes in the intracellular metabolite profiles reflected the response of the C. asiatica cells to the MeJa-treatment as a reprogramming of the metabolome.

  4. Three hydroxylated lupeol-based triterpenoid esters isolated from the Eastern Nigeria mistletoe parasitic on Kola acuminata.

    Science.gov (United States)

    Omeje, Edwin Ogechukwu; Osadebe, Patience Ogoamaka; Esimone, Charles Okechukwu; Nworu, Chukwuemeka Sylvester; Kawamura, Akira; Proksch, Peter

    2012-01-01

    Column fractionation and purification of an n-hexane fraction led to the isolation of three lupeol-based triterpenoid esters from the leaves of the Eastern Nigeria mistletoe, Loranthus micranthus Linn parasitic on a local kola nut tree, Kola acuminata. These three compounds were adequately characterised using a combination of UV/visible, IR, NMR (¹³C-NMR and ¹H-NMR), DEPT, MS and two-dimensional correlation (H-H COSY, Hetero-nuclear Single Quantum Correlation (HSQC), HMBC, NOE and NOESY) studies as 7β,15α-dihydroxyl-lup-20(29)-ene-3β-esters of palmitic (I), stearic (II) and eicosanoic acids (III). The characterisation of other isolated compounds is ongoing. Remarkably, this is the first report of the existence of fatty acid esters of an unusual 7β,15α-dihydroxylated lupeol in the Eastern Nigeria mistletoe. These isolated compounds might contribute in part to the numerous established bio-activities of the Eastern Nigeria mistletoes.

  5. Conformational energetics of cationic backbone rearrangements in triterpenoid biosynthesis provide an insight into enzymatic control of product.

    Science.gov (United States)

    Kürti, László; Chein, Rong-Jie; Corey, E J

    2008-07-16

    2,3-( S)-Oxidosqualene (C 30H 50O) serves as a versatile starting point for the remarkable biosynthesis of many isomeric naturally occurring triterpenoids of formula C 30H 50O. These biosyntheses all involve polycyclization via cationic intermediates. The fully cyclized primary products then are converted to various structures by cationic rearrangements involving the polycyclic backbone. The energetics of these rearrangements has been examined by B3LYP 6-31 G* DFT calculations and by ab initio Hartree-Fock calculations at the 6-31G* or 3-21G(*) level. The results have led to the conclusion that the biosynthesis of friedelin, the most drastically rearranged of the pentacyclic triterpenes, involves a complex nonstop process, with no stable intermediates between 2,3-( S)-oxidosqualene and friedelin. It is proposed that this single-reaction biosynthesis consists of pentacyclization to the lupanyl cation followed directly by a sequence of 10 suprafacial 1,2-shifts of carbon and hydrogen, driven by the large exergonicity of the pentacyclization and electrostatic acceleration of the rearrangement steps.

  6. Purification of two triterpenoids from Schisandra chinensis by macroporous resin combined with high-speed counter-current chromatography.

    Science.gov (United States)

    Zhu, Lijie; Li, Bin; Liu, Xiuying; Meng, Xianjun

    2014-10-01

    A method for preparative purification of corosolic acid and nigranoic acid from Schisandra chinensis (SC) was established using a combination of macroporous absorption resin column separation and high-speed counter-current chromatography (HSCCC). The crude extracts obtained from SC using 70% ethanol were separated on a macroporous resin column and then eluted with a graded ethanol series. The 70% ethanol fraction was used as the sample for separation of the two triterpenoids by HSCCC. The two-phase solvent system used for HSCCC separation was chloroform-n-butanol-methanol-water (10:0.5:7:4, v/v/v/v). The upper phase was used as the stationary phase of HSCCC. Corosolic acid (16.4 mg) of 96.3% purity and nigranoic acid (9.5 mg) of 98.9% purity were obtained in a one-step HSCCC separation from 100 mg of the sample. The structures of corosolic acid and nigranoic acid were identified by (1)H-nuclear magnetic resonance (NMR) and (13)C-NMR.

  7. 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, Pmemory. 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.

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

    Science.gov (United States)

    Liu, Tao; Zhao, Jun; Ma, Long; Ding, Yusong; Su, Deqi

    2012-01-01

    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.

  9. Inhibition of efflux pumps in methicillin-resistant Staphylococcus aureus and Enterococcus faecalis resistant strains by triterpenoids from Momordica balsamina.

    Science.gov (United States)

    Ramalhete, Cátia; Spengler, Gabriella; Martins, Ana; Martins, Marta; Viveiros, Miguel; Mulhovo, Silva; Ferreira, Maria-José U; Amaral, Leonard

    2011-01-01

    Six cucurbitane-type triterpenoids (1-6) isolated from the aerial parts of Momordica balsamina were evaluated for their ability to inhibit the activity of bacterial efflux pumps of methicillin-resistant Staphylococcus aureus (MRSA) COL(OXA), Enterococcus faecalis ATCC 29212, Salmonella enterica subsp. I serovar Typhimurium 5408 and S. Typhimurium 5408CIP strains. The latter strain overproduces the AcrB transporter of the AcrAB-TolC efflux pump six-fold compared with its parent. Compounds 4-6 were also tested for similar activity against Escherichia coli AG100 wild-type strain and E. coli AG100TET8 that overproduces the AcrAB-TolC efflux pump. Evaluation of efflux activity was performed using a semi-automated method that measures accumulation of the universal efflux pump substrate ethidium bromide (EtBr). Some of the compounds significantly inhibited efflux of EtBr by MRSA COL(OXA) and E. faecalis ATCC 29212. A correlation between activity and the topological polar surface area of the compounds was found for MRSA COL(OXA). Copyright © 2010 Elsevier B.V. and the International Society of Chemotherapy. All rights reserved.

  10. 腺花香茶菜中的三萜化合物%Triterpenoids from Isodon adenanthus

    Institute of Scientific and Technical Information of China (English)

    姜北; 韩全斌; 项伟; 林中文; 孙汉董

    2002-01-01

    Further investigation on the leaves of Isodon adenanthus afforded a new triterpenoid, isodonadenanthin (1), together with three known ones, ursolic acid, 2αhydroxylursolic acid and 2α, 24dihydroxylursolic acid. Structures of 14 were elucidated on the basis of their spectral properties. The cytotoxicities of the new compound against three kinds of human tumor cells K562, A549, and T24 were also tested. And1showed a certain antitumor activities toward all three kinds of cells.%对云南大理产腺花香茶菜(Isodon adenanthus)进行了系统的研究.从中分离得到了包括1个新三萜(1)在内的一系列乌索烷型三萜类化合物,其结构通过现代波谱分析方法确定.活性筛选结果表明,化合物1对肿瘤细胞株K562,A549以及T24具有一定的细胞毒活性.

  11. 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

  12. 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.

  13. Lupeol, a pentacyclic triterpenoid isolated from Vernonia cinerea attenuate selenite induced cataract formation in Sprague Dawley rat pups.

    Science.gov (United States)

    Asha, Radha; Gayathri Devi, V; Abraham, Annie

    2016-02-05

    This study investigated the inhibitory effects of active component isolated from flavonoid fraction of Vernonia cinerea (FVC), lupeol on selenite induced cataract formation. Previous reports suggest that phytochemicals or natural plant products retard the process of cataractogenesis by scavenging free oxygen radicals. Hence, the present study sought to assess the potential of lupeol on in vivo selenite induced cataract models. Lupeol, a pentacyclic triterpenoid, was isolated from the ethyl acetate fraction of methanolic extract of Vernonia cinerea, follows standard chromatographic techniques. Structural elucidation of the compound was carried out using (1)H NMR, (13)C NMR, Mass spectrometry together with other complementary techniques (UV and IR). From these, the isolated compound was identified as Lupeol (3'-hydroxylup-20(29)-ene). The antioxidant activity was comparatively studied using DPPH radical scavenging and FRAP assay. Lupeol exhibited higher DPPH radical scavenging activity as well as reducing power assay. In this study, cataract was induced by a single subcutaneous injection of sodium selenite (4 μg/g body weight) on rat pups. Lupeol was administered orally from 8th day upto 21st day at a concentration 25 μg/g body weight. Cataract was visualized on 16th day with the help of an ophthalmoscope and later on with the naked eye. On the 30th day, rats were euthanized by sodium pentothal injection, lenses were excised and the biochemical parameters such as activity of superoxide dismutase (SOD), catalase (CAT), Glutathione peroxidase (GPx), Glutathione reductase (GR), Glutathione-S-transferase (GST), Ca(2+) ATPase, glutathione content (GSH), reactive oxygen species (ROS), lipid peroxidation products (malondialdehyde) were estimated and found effective in the treatment of cataract by lupeol.

  14. Antivenom activity of triterpenoid (C34H68O2) from Leucas aspera Linn. against Naja naja naja venom induced toxicity: antioxidant and histological study in mice.

    Science.gov (United States)

    Venkatesan, C; Sarathi, M; Balasubramanian, G; Thomas, John; Balachander, V; Babu, V Sarath; Bilal, S Mohammed Yusuf; Majeed, S Abdul; Madan, N; Raj, N Sundar; Vimal, S; Nambi, K S N; Hameed, A S Sahul

    2014-04-01

    The isolated and identified triterpenoid, 1-hydroxytetratriacontane-4-one (C34H68O2), obtained from the methanolic leaf extract of Leucas aspera Linn. was explored for the first time for antisnake venom activity. The plant (L. aspera Linn.) extract significantly antagonized the spectacled cobra (Naja naja naja) venom induced lethal activity in a mouse model. It was compared with commercial antiserum obtained from King Institute of Preventive Medicine (Chennai, Tamil Nadu, India). N. naja naja venom induced a significant decrease in antioxidant superoxide dismutase, glutathione (GSH) peroxidase, catalase, reduced GSH and glutathione-S-transferase activities and increased lipid peroxidase (LPO) activity in different organs such as heart, liver, kidney and lungs. The histological changes following the antivenom treatment were also evaluated in all these organs. There were significant alterations in the histology. Triterpenoid from methanol extract of L. aspera Linn. at a dose level of 75 mg per mouse significantly attenuated (neutralized) the venom-induced antioxidant status and also the LPO activity in different organs.

  15. 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.

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

    Science.gov (United States)

    Villar-Lorenzo, Andrea; Ardiles, Alejandro E; Arroba, Ana I; Hernández-Jiménez, Enrique; Pardo, Virginia; López-Collazo, Eduardo; Jiménez, Ignacio A; Bazzocchi, Isabel L; González-Rodríguez, Águeda; Valverde, Ángela M

    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 25μM 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.

  17. A Novel Strategy for Inducing the Antitumor Effects of Triterpenoid Compounds: Blocking the Protumoral Functions of Tumor-Associated Macrophages via STAT3 Inhibition

    Directory of Open Access Journals (Sweden)

    Yukio Fujiwara

    2014-01-01

    Full Text Available There are many types of nontumor cells, including leukocytes, fibroblasts, and endothelial cells, in the tumor microenvironment. Among these cells, infiltrating macrophages have recently received attention as novel target cells due to their protumoral functions. Infiltrating macrophages are called tumor-associated macrophages (TAMs. TAMs polarized to the M2 phenotype are involved in tumor development and are associated with a poor clinical prognosis. Therefore, the regulation of TAM activation or M2 polarization is a new strategy for antitumor therapy. We screened natural compounds possessing an inhibitory effect on the M2 polarization of human macrophages. Among 200 purified natural compounds examined, corosolic acid (CA and oleanolic acid (OA, both are categorized in triterpenoid compounds, inhibited macrophage polarization to M2 phenotype by suppressing STAT3 activation. CA and OA also directly inhibited tumor cell proliferation and sensitized tumor cells to anticancer drugs, such as adriamycin and cisplatin. The in vivo experiments showed that CA significantly suppressed subcutaneous tumor development and lung metastasis in a murine sarcoma model. The application of triterpenoid compounds, such as CA and OA, is a potential new anticancer therapy targeting macrophage activation, with synergistic effects with anticancer agents.

  18. 从单条草中分得一个新的三萜皂苷%A new triterpenoid saponin from Lysimachia candida

    Institute of Scientific and Technical Information of China (English)

    张晓瑢; 彭树林; 王明奎; 丁立生

    2002-01-01

    目的对报春花科珍珠菜属药用植物单条草Lysimachia candida的化学成分进行研究.方法采用硅胶柱层析进行分离和纯化,通过波谱和化学方法进行结构鉴定.结果从正丁醇萃取部分分离出1个三萜皂苷类化合物,结构鉴定为:3β,16a-二羟基齐墩果-12-烯-28-醛-3-O-β-D-吡喃葡萄糖基-23-O-a-D-呋喃核糖苷,命名为单条草苷甲(I).结论单条草苷甲是新结构的三萜皂苷.%Object To investigate the chemical constituents from the whole plant of Lysimachia candida Ldl.. Methods The constituents were isolated and purified on silica gel column chromatography.Their structures were elucidated by chemical and spectroscopic evidence. Results A triterpenoid saponin,named candidoside A ( Ⅰ ), was isolated from the extract of n-BuOH. Its structure was shown to be 3β,16α-dihydroxy-olean-12-en-28-al-3-O-β-D-glucopyranosyl-23-O-α-D-ribofuranoside. Conclusion Candidoside A was a new triterpenoid saponin.

  19. 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

    Directory of Open Access Journals (Sweden)

    Hua-Gang Liu

    2013-03-01

    Full Text Available 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.

  20. Anti-platelet aggregation triterpene saponins from the galls of Sapindus mukorossi.

    Science.gov (United States)

    Huang, Hui-Chi; Tsai, Wei-Jern; Liaw, Chia-Ching; Wu, Shih-Hsiung; Wu, Yang-Chang; Kuo, Yao-Haur

    2007-09-01

    Bioassay-directed fractionation of an ethanolic extract of the galls of Sapindus mukorossi has resulted in the isolation of two new tirucallane-type triterpenoid saponins, sapinmusaponins Q (1) and R (2), along with three known oleanane-type triterpenoid saponins (3-5). Their structures were elucidated on the basis of spectroscopic analysis and chemical hydrolysis. Biological evaluation showed that both sapinmusaponins Q and R demonstrated more potent anti-platelet aggregation activity than aspirin.

  1. 不同产地灵芝中三萜及甾醇的含量考察%Determination of Triterpenoids and Sterol Content of Glossy ganoderma of different origin

    Institute of Scientific and Technical Information of China (English)

    林绍瑜; 胡晓文

    2016-01-01

    Objective To analyse the triterpenoids and sterol content of Glossy ganoderma of different origin,such as Shandong, Anhui, Zhejiang and so on.Methods Oleanolic acid was used as a reference substance and ultraviolet-visible spec trophotometry was used to determine the triterpenoids and sterol content of Glossy ganoderma.Results The highest triterpenoids and sterol content of Glossy ganoderma is Shandong, next is Zhejiang and next is Anhui.Conclusion There are significant differences in the contents of triterpenoids and sterol of Glossy ganoderma in Shandong,Anhui and Zhejiang.%目的:分析测定山东、安徽、浙江不同产地灵芝的三萜及甾醇含量。方法:以齐墩果酸为对照品,用紫外-可见分光光度法测定三萜及甾醇含量。结果:三萜及甾醇含量最高的为山东灵芝,其次为浙江灵芝,再次为安徽灵芝。结论:山东、安徽、浙江三产地灵芝中三萜及甾醇含量存在明显的差异。

  2. A new dammarane saponin and other triterpenoids from Siolmatra brasiliensis and evaluation of the antidiabetic activity of its extract.

    Science.gov (United States)

    Dos Santos, Carlos Henrique Corrêa; Borges, Izabeau Pontes; da Silva, Virgínia Claudia; de Sousa, Paulo Teixeira; Kawashita, Nair Honda; Baviera, Amanda Martins; Carvalho, Mario Geraldo de

    2016-09-01

    Context Siolmatra brasiliensis (Cogn.) Baill (Cucurbitaceae) is a climbing plant widely used for the treatment of diabetes mellitus symptoms. Objective This work evaluates the antidiabetic activity of an extract of S. brasiliensis in streptozotocin-diabetic rats and promotes the phytochemical investigation to isolate the major compounds of the same extract. Materials and methods Male Wistar rats were divided into normal (N) and diabetic rats (DC) treated with water; diabetic rats treated with 3U insulin (DI) or with 250 (DSb250) or 500 mg/kg (DSb500) of hydroalcoholic extract of the stalks of S. brasiliensis, via oral gavage, for 21 days. Physiological and biochemical parameters classically altered in diabetes were monitored. The triterpenoids were isolated from the ethyl acetate fraction under silica gel column chromatography and Sephadex-LH20 methods and their structures were determined by NMR, HR-ESI-MS and DC analysis. Results When compared with DC, DSb250 rats showed a reduction in the hyperglycemia (DC: 26.46 ± 0.69 versus DSb250: 19.67 ± 1.06 mmol/L) and glycosuria (DC: 43.02 ± 3.19 versus DSb250: 28.46 ± 2.14 mmol/24 h) and increase in hepatic glycogen (DC: 14.44 ± 1.26 versus DSb250: 22.08 ± 4.26 mg/g). Three known cucurbitacins were isolated from a hydroalcoholic extract of S. brasiliensis, i.e., cayaponosides A1, B4, D, and a new dammarane saponin 3-O-β-d-gentiobiosyl-26-O-β-d-glucopyranosyl-20-hydroxydammar-24-ene. The structures of these compounds were elucidated by spectral data analysis of the natural products and their acetyl derivatives. Discussion and conclusion The known cucurbitacins and/or the new identified saponin may be related with the antidiabetic activity of S. brasiliensis.

  3. 紫外分光光度-比色法检测柿蒂中三萜类化合物的含量%Detection of Triterpenoid Content in Persimmon Calyx by Ultraviolet Spectrophotometry-colorimetry

    Institute of Scientific and Technical Information of China (English)

    蒋莺; 钟晓红; 陆英; 程建宇; 张双; 何艳君

    2013-01-01

    The conditions for detecting triterpenoid content in persimmon calyx by ultraviolet spectrophotometry-colorimetry were optimized,and the triterpenoid content in different varieties of persimmon calyx in different harvest periods was detected.The results showed that the optimal colorimetry conditions were 0.4 mL of 5% vanillin-glacial acetic acid,0.8 mL of perchloric acid,detecting absorbency within 20-60 min.With the optimal colorimetry conditions,the RSD was 1.66%,the absorbency was relatively stable,and the precision was great.The testing results for triterpenoid content in of different varieties persimmon calyx in different harvest periods showed that all of the harvested varieties had the highest triterpenoid content in May; the triterpenoid content showed a decreasing trend with growth period developed; the triterpenoid content had the hug difference between different varieties at the same harvest period; the triterpenoid content in Sandaijin,Shuishi and Niuxinshi in different harvest periods all was relatively high,and that in Cilang was the lowest.%对紫外分光光度-比色法检测柿蒂三萜类化合物含量的条件进行了优化,并对不同品种不同采收时期柿蒂中的三萜类化合物含量进行了检测.结果表明:最佳的比色条件为5%香草醛-冰醋酸0.4 mL,高氯酸0.8 mL,在20~60 min内测定吸光度,此时相对标准偏差RSD为1.66%,吸光度较稳定,精密度好.对不同采收时期不同品种柿蒂中三萜类化合物含量的检测结果表明,所有采收品种在5月时三萜类化合物含量最高,随着生长期的延长均呈下降趋势,同一时期不同品种间三萜类化合物含量相差较大,三代斤、水柿和牛心柿不同采收时期三萜类化合物含量均较高,次郎含量最低.

  4. 18, 19-Secooleanane Type Triterpene Glycosyl Esters from the Bark of Terminalia arjuna

    Science.gov (United States)

    Five novel 18,19-secooleanane type triterpene glycosides, 1-5, were isolated from the MeOH extract of the bark of Teminalia arjuna, along with nine known oleanane triterpenoids. The structures of the new compounds were determined by spectroscopic analyses, including 2D NMR, HRESIMS and CD spectra....

  5. Holophyllane A: A Triterpenoid Possessing an Unprecedented B-nor-3,4-seco-17,14-friedo-lanostane Architecture from Abies holophylla

    Science.gov (United States)

    Kim, Chung Sub; Oh, Joonseok; Subedi, Lalita; Kim, Sun Yeou; Choi, Sang Un; Lee, Kang Ro

    2017-01-01

    A novel triterpenoid, holophyllane A (1), featuring a B-nor-3,4-seco-17,14-friedo-lanostane, along with its putative precursor, compound 2 were isolated from the methanol extract of the trunks of Abies holophylla. The 2D structure and relative configuration of 1 were initially determined via analysis of 1D and 2D NMR spectroscopic data and the assignment was confirmed by quantum mechanics-based NMR chemical shift calculations. The absolute configuration was established by comparison of the experimental and simulated ECD data generated at different theory levels. Compounds 1 and 2 exhibited moderate to weak cytotoxicity and significant inhibitory activity against nitric oxide (NO) production. PMID:28252664

  6. 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.

  7. Five new 3,4-seco-lanostane-type triterpenoids with antiproliferative activity in human leukemia cells isolated from the roots of Kadsura coccinea.

    Science.gov (United States)

    Wang, Nan; Li, Zhan-lin; Song, Dan-dan; Li, Wei; Pei, Yue-hu; Jing, Yong-kui; Hua, Hui-ming

    2012-10-01

    Five new 3,4-seco-lanostane-type triterpenoids, seco-coccinic acids G-K (1-5), and a known compound, seco-coccinic F, were isolated from the roots of Kadsura coccinea (Lem.) A. C. Sm. Their structures were elucidated by spectroscopic methods, including 2D-NMR and HR-MS techniques. The cell growth inhibitory effects of these compounds were assayed in human leukemia HL-60 cells, and it was found that 1, 5, and 6 showed antiproliferative effects with GI₅₀ values of 28.4, 15.2, and 16.6 µM, respectively. Georg Thieme Verlag KG Stuttgart · New York.

  8. The effect of drought stress on the expression of key genes involved in the biosynthesis of triterpenoid saponins in liquorice (Glycyrrhiza glabra).

    Science.gov (United States)

    Nasrollahi, Vida; Mirzaie-asl, Asghar; Piri, Khosro; Nazeri, Sonbol; Mehrabi, Rahim

    2014-07-01

    Glycyrrhiza glabra is an important medicinal plant throughout the world. Glycyrrhizin is a triterpenoid that is among the most important secondary metabolites produced by liquorice. Drought stress is proposed to enhance the levels of secondary metabolites. In this study, the effect of drought stress on the expression of important genes involved in the glycyrrhizin biosynthetic pathway was examined. Drought stress at the seedling stage was applied to 8-day-old plants using polyethylene glycol. Subsequently, the samples were collected 0, 4, 8 or 24 h post-treatment. At the adult plant stage, 10-month-old plants were subjected to drought stress by discontinuing irrigation. Subsequently, samples were collected at 2, 16 and 28 days after drought imposition (S(2d), S(16d) and S(28d), respectively). We performed semi-quantitative RT-PCR assays to evaluate the gene expression levels of sequalene synthase (SQS), β-amyrin synthase (bAS), lupeol synthase (LUS) and cycloartenol synthase (CAS) during stress. Finally, the glycyrrhizin content of stolons was determined via HPLC. The results revealed that due to osmotic stress, the gene expression levels of SQS and bAS were increased, whereas those of CAS were relatively unchanged at the seedling stage. At the adult plant stage, the expression levels of SQS and bAS were increased under drought stress conditions, whereas the gene expression level of CAS remained relatively constant. The glycyrrhizin content in stolons was increased only under severe drought stress conditions (S(28d)). Our results indicate that application of controlled drought stress up-regulates the expression of key genes involved in the biosynthesis of triterpenoid saponins and directly enhances the production of secondary metabolites, including glycyrrhizin, in liquorice plants.

  9. 灵芝三萜类化合物提取纯化及检测技术研究进展%Research Progress on Extraction, Purification and Determination Technology for GANODERMA Triterpenoids

    Institute of Scientific and Technical Information of China (English)

    吕超田; 曾卫国; 柯春林; 杨贤松

    2011-01-01

    Triterpenoids was one of the major medicinal effective ingredients in GANODERMA. The research status on extraction, purification and determination techniques for triterpenoids from fruiting body, mycelium and fermentation broth of GANODERMA were summarized in the paper, so as to provide basis for the quality control of GANODERMA products.%三萜类化合物是灵芝的主要活性成分之一,该文就灵芝子实体、菌丝体及发酵液中三萜类物质的提取、纯化及检测技术的研究现状进行了综述,为灵芝制品的质量控制奠定基础.

  10. Chemical shift assignments of two oleanane triterpenes from Euonymus hederaceus

    Institute of Scientific and Technical Information of China (English)

    HU He-jiao; WANG Kui-wu; WU Bin; SUN Cui-rong; PAN Yuan-jiang

    2005-01-01

    1H-NMR and 13C-NMR assignments of 12-oleanene-3,11-dione (compound 1) were completely described for the first time through conventional 1D NMR and 2D shift-correlated NMR experiments using 1H-1HCOSY, HMQC, HMBC techniques.Based on its NMR data, the assignments of 28-hydroxyolean-12-ene-3,11-dione (compound 2) were partially revised.

  11. Assignment of the absolute configuration of hepatoprotective highly oxygenated triterpenoids using X-ray, ECD, NMR J-based configurational analysis and HSQC overlay experiments.

    Science.gov (United States)

    Wang, Xiaojuan; Liu, Jiabao; Pandey, Pankaj; Chen, Jiabao; Fronczek, Frank R; Parnham, Stuart; Qi, Xinzhu; Doerksen, Robert J; Ferreira, Daneel; Sun, Hua; Li, Shuai; Hamann, Mark T

    2017-09-14

    The plants of the genus Kadsura are widely distributed in China, South Korea, and Japan. Their roots and stems are traditionally used to treat blood diseases and pain. The main bioactive constituents of Kadsura longipedunculata comprise highly oxygenated triterpenoids. Schiartane-type nortriterpenoids showed anti-HIV, anti-HBV, and cytotoxic bioactivities. For such compounds, the absolute configuration influences the bioactivities, and hence its unambiguous determination is essential. In this work, the absolute configurations of three highly oxygenated schiartane-type nortriterpenoids were unequivocally assigned using X-ray, ECD, and J-based configuration analysis and HSQC overlay data. The ethanol extract of Kadsura longipedunculata Finet et Gagnep was purified by column chromatography using silica, Sephadex LH-20, and ODS as substrates. To help assign the absolute configuration of schiartane-type nortriterpenoids, X-ray diffraction analysis, ECD experiment compared to ab initio computed data, DP4+ analysis, HSQC overlay, NOESY, and J-based configuration analysis were carried out. Hetero- and homo-nuclear coupling constants were extracted from HETLOC experiments. Three new highly oxygenated triterpenoids, micrandilactone I (1), micrandilactone J (2), and 22, 23-di-epi-micrandilactone J (3) were isolated. Their 2D structures were solved using NMR and HRESIMS data and their absolute configurations were elucidated using X-ray diffraction analysis, ECD experimental results compared to ab initio computed spectra, HSQC overlay, DP4 plus, NOESY, and J-based configuration analysis. Micrandilactone I (1) and 22, 23-di-epi-micrandilactone J (3) showed moderate hepatoprotective activity against APAP-induced toxicity in HepG2 cells with cell survival rates of 53.0 and 50.2%, respectively, at 10μM (bicyclol, 49.0%), while micrandilactone J (2) was inactive. This is the first comprehensive stereochemical assignment of a non-crystalline schiartane-type nortriterpenoid like 3

  12. A synthetic triterpenoid CDDO-Im inhibits tumorsphere formation by regulating stem cell signaling pathways in triple-negative breast cancer.

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    Jae Young So

    Full Text Available Triple-negative breast cancer is associated with poor prognosis because of a high rate of tumor recurrence and metastasis. Previous studies demonstrated that the synthetic triterpenoid, CDDO-Imidazolide (CDDO-Im induced cell cycle arrest and apoptosis in triple-negative breast cancer. Since a small subpopulation of cancer stem cells has been suggested to be responsible for drug resistance and metastasis of tumors, our present study determined whether the effects of CDDO-Im in triple-negative breast cancer are due to the inhibition of a cancer stem cell subpopulation. CDDO-Im treatment markedly induced cell cycle arrest at G2/M-phase and apoptosis in the triple-negative breast cancer cell lines, SUM159 and MDA-MB-231. Because SUM159 cells were more sensitive to CDDO-Im than MDA-MB-231 cells, the effects of CDDO-Im on the cancer stem cell subpopulation were further investigated in SUM159 cells. SUM159 cells formed tumorspheres in culture, and the cancer stem cell subpopulation, CD24-/EpCAM+ cells, was markedly enriched in SUM159 tumorspheres. The CD24-/EpCAM+ cells in SUM159 tumorspheres were significantly inhibited by CDDO-Im treatment. CDDO-Im also significantly decreased sphere forming efficiency and tumorsphere size in both primary and secondary sphere cultures. PCR array of stem cell signaling genes showed that expression levels of many key molecules in the stem cell signaling pathways, such as Notch, TGF-β/Smad, Hedgehog and Wnt, were significantly down-regulated by CDDO-Im in SUM159 tumorspheres. Protein levels of Notch receptors (c-Notch1, Notch1 and Notch3, TGF-β/Smad (pSmad2/3 and Hedgehog downstream effectors (GLI1 also were markedly reduced by CDDO-Im. In conclusion, the present study demonstrates that the synthetic triterpenoid, CDDO-Im, is a potent anti-cancer agent against triple-negative breast cancer cells by targeting the cancer stem cell subpopulation.

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

    Institute of Scientific and Technical Information of China (English)

    Fatiany Pierre Ruphin; Robijaona Baholy; Randrianarivo Emmanuel; Raharisololalao Amelie; Marie-Therese Martin; Ngbolua Koto-te-Nyiwa

    2013-01-01

    Objective: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. Methods: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. Results: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. Conclusions:The results suggest that furthers studies involving antineoplastic activity is needed for the development of this lead compound as anticancer drug.

  14. A Triterpenoid Inhibited Hormone-Induced Adipocyte Differentiation and Alleviated Dexamethasone-Induced Insulin Resistance in 3T3-L1 adipocytes.

    Science.gov (United States)

    Qin, Ji-Huan; Ma, Jun-Zeng; Yang, Xing-Wei; Hu, Ying-Jie; Zhou, Juan; Fu, Lin-Chun; Tian, Ru-Hua; Liu, Shan; Xu, Gang; Shen, Xiao-Ling

    2015-06-01

    6α-Hydroxylup-20(29)-en-3-on-28-oic acid (1), a natural triterpenoid, was found to possess the ability in a dose-dependent manner inhibiting hormone-induced adipocyte differentiation in 3T3-L1 preadipocytes, and restoring glucose consuming ability in dexamethasone (DXM)-induced insulin resistant 3T3-L1 adipocytes. Compound 1 was also found to ameliorate DXM-induced adipocyte dysfunction in lipolysis and adipokine secretion. Mechanistic studies revealed that 1 inhibited adipocyte differentiation in 3T3-L1 preadipocytes via down-regulating hormone-stimulated gene transcription of peroxisome proliferator-activated receptor γ and CCAAT-enhancer-binding protein alpha which are key factors in lipogenesis, and restored DXM-impaired glucose consuming ability in differentiated 3T3-L1 adipocytes via repairing insulin signaling pathway and activating down-stream signaling transduction by phosphorylation of signaling molecules PI3K/p85, Akt2 and AS160, thus leading to increased translocation of glucose transporter type 4 and transportation of glucose.

  15. Triterpenoid saponin flaccidoside II from Anemone flaccida triggers apoptosis of NF1-associated malignant peripheral nerve sheath tumors via the MAPK-HO-1 pathway

    Directory of Open Access Journals (Sweden)

    Han LT

    2016-04-01

    Full Text Available Lin-tao Han,1 Yin Fang,1 Yan Cao,2 Feng-hua Wu,1 E Liu,2 Guo-yan Mo,2 Fang Huang1 1China Key Laboratory of TCM Resource and Prescription, Ministry of Education, 2Department of Pharmacy, Hubei University of Chinese Medicine, Wuhan, Hubei, People’s Republic of China Abstract: Malignant peripheral nerve sheath tumors (MPNSTs are highly aggressive soft tissue neoplasms that are extremely rare and are frequently associated with neurofibromatosis type 1 patients. MPNSTs are typically fatal, and there is no effective treatment so far. In our previous study, we showed that flaccidoside II, one of the triterpenoid saponins isolated from Anemone flaccida Fr. Schmidt, has antitumor potential by inducing apoptosis. In the present study, we found that flaccidoside II inhibits proliferation and facilitates apoptosis in MPNST cell lines ST88-14 and S462. Furthermore, this study provides a mechanism by which the downregulation of heme oxygenase-1 via extracellular signal-regulated kinase-1/2 and p38 mitogen-activated protein kinase pathways is involved in the apoptotic role of flaccidoside II. This study suggested the potential of flaccidoside II as a novel pharmacotherapeutic approach for MPNSTs. Keywords: flaccidoside II, malignant peripheral nerve sheath tumors, apoptosis, MAPK, HO-1

  16. 土贝母中一个新的三萜皂苷%A novel triterpenoid saponin from bulbs of Bolbostemma paniculatum

    Institute of Scientific and Technical Information of China (English)

    马挺军; 李军; 屠鹏飞; 吕飞杰

    2006-01-01

    Objective To study the triterpenoid saponin from bulbs of Bolbostemma paniculatum.Methods The compound was isolated by repeated silica gel chromatographies and its strcuture was eluci-dated on the basis of physico chemical property and spectral analysis. Results A novel triterpenoidsaponin was isolated and determined as olean 12-en-28-oic acid, 3- {[2-O-[6-O-[(3R)-4-carboxy-3-hydrox-y-3-methyl-1-oxobutyl]-β-D-glucopyranosyl]-β-D-glucopyranosyl] oxy}-2, 16, 23-trihydroxy-28-[2-O-α-L-rhamnose (1→2)-α-L-arabinopyranosyl] ester ( I φ. Conclusion Compound I is a novel compoundnamed as dexylosyltubeimoside Ⅲ.%目的对土贝母Bolbostemma paniculatum的三萜皂苷成分进行分离和结构鉴定.方法采用反复柱色谱方法进行分离,通过理化性质和波谱分析鉴定结构.结果从土贝母中分离并鉴定了1个新的三萜皂苷脱木糖土贝母苷丙(dexylosyltubeimoside Ⅲ).结论化合物Ⅰ为新化合物.

  17. Montecrinanes A-C: Triterpenes with an Unprecedented Rearranged Tetracyclic Skeleton from Celastrus vulcanicola. Insights into Triterpenoid Biosynthesis Based on DFT Calculations.

    Science.gov (United States)

    Purino, Martín; Ardiles, Alejandro E; Callies, Oliver; Jiménez, Ignacio A; Bazzocchi, Isabel L

    2016-05-23

    Three new triterpenoids with an unprecedented 6/6/6/6-fused tetracyclic carbon skeleton, montecrinanes A-C (1-3), were isolated from the root bark of Celastrus vulcanicola, along with known D:B-friedobaccharanes (4-6), and lupane-type triterpenes (7-12). The stereostructures of the new metabolites were elucidated based on spectroscopic (1D and 2D NMR) and spectrometric (HR-EIMS and HR-ESIMS) techniques. Their absolute configurations were determined by both NMR spectroscopy, with (R)-(-)-α-methoxyphenylacetic acid as a chiral derivatizing agent, and biogenetic considerations. Biogenetic pathways for montecrinane and D:B-friedobaccharane skeletons were proposed and studied by DFT methods. The theoretical results support the energetic feasibility of the putative biogenetic pathways, in which the 1,2-methyl shift from the secondary baccharenyl cation represents a novel and key reaction step for a new montecrinane skeleton. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  18. Qualitative and Quantitative Analysis of Major Triterpenoids in Alismatis Rhizoma by High Performance Liquid Chromatography/Diode-Array Detector/Quadrupole-Time-of-Flight Mass Spectrometry and Ultra-Performance Liquid Chromatography/Triple Quadrupole Mass Spectrometry

    Directory of Open Access Journals (Sweden)

    Wanli Zhao

    2015-07-01

    Full Text Available Alismatis Rhizoma (AMR is a well-known natural medicine with a long history in Chinese medicine and has been commonly used for treating a wide range of ailments related to dysuria, edema, nephropathy, hyperlipidaemia, diabetes, inflammation as well as tumors in clinical applications. Most beneficial effects of AMR are attributed to the presence of protostane terpenoids, the major active ingredients of Alismatis Rhizoma (AMR. In this study, a systematic high performance liquid chromatography/diode-array detector/quadrupole-time-of-flight mass spectrometry (HPLC-DAD-Q-TOF MS and ultra-performance liquid chromatography/triple quadrupole mass spectrometry (UPLC-QqQ MS method was developed for qualitative and quantitative analyses of the major AMR triterpenoids. First, a total of 25 triterpenoid components, including 24 known compounds and one new compound were identified by comparison with UV spectra, molecular ions and fragmentation behaviors of reference standards or the literature. Second, an efficient method was established for the rapid simultaneous determination of 14 representative triterpenoids by UPLC-QqQ MS. Forty-three batches of AMR were analyzed with linearity (r, 0.9980–0.9999, intra-day precision (RSD, 1.18%–3.79%, inter-day precision (RSD, 1.53%–3.96%, stability (RSD, 1.32%–3.97%, repeatability (RSD, 2.21%–4.25%, and recovery (98.11%–103.8%. These results indicated that new approaches combining HPLC-DAD-Q-TOF MS and UPLC-QqQ MS are applicable in the qualitative and quantitative analysis of AMR.

  19. 响应面法优化微波辅助提取山楂核三萜的研究%Optimization of Microwave-assisted Extraction of Triterpenoid in Hawthorn Seed by Response Surface Methodology

    Institute of Scientific and Technical Information of China (English)

    寇云云; 杜彬; 王同坤; 杨越冬

    2011-01-01

    The optimal conditions for hawthorn seed were evaluated by means of response surface methodology.Microwave-assisted extraction was applied to extract triterpenoid from hawthorn seed.The effects of four independents variables in terms of methanol concentration,ratio of solvent-to-solid,microwave power and microwave processing time on the triterpenoid yield were determined.On the basis of single-factor experiments,a quadratic polynomial regression equation of the forecasting model was set up by using Box-Behnken design.The optimal extraction parameters to obtain the highest triterpenoid yield were ratio of solvent-to-solid 17 mL/g,methanol concentration 60%,microwave treatment time 97 s,microwave power 640 W.The average experimental triterpenoid yield under the optimum conditions was found to(1.143±0.008)%,which agreed with the predicted value of 1.12%.%利用响应面分析法优山楂核三萜的提取工艺。以山楂核三萜的得率为考核指标,研究甲醇体积分数、液料比、微波功率、微波时间对山楂核三萜提取的影响,在单因素试验的基础上,根据Box-Benhnken设计原理,设计四因素三水平响应面分析法,建立二次多项式回归方程的预测模型,获得最佳工艺参数:液料比17 mL/g、甲醇体积分数60%、微波功率640 W、微波时间97 s。在此条件下获得山楂核三萜的理论得率为1.12%,实际测得山楂核三萜得率为(1.143±0.008)%,与理论预测值基本相符。

  20. Determination of Total Triterpenoids of Different Apple Varieties in Apple Peel and Apple Flesh%不同品种苹果果皮和果肉中总三萜含量的测定

    Institute of Scientific and Technical Information of China (English)

    李志华; 宋晓凯; 赵艳敏; 刘岱琳

    2014-01-01

    To establish a method for the determination of total triterpenoids from apple peel and apple flesh by folin-ciocalteu colorimetry. With ursolic acid as reference substance, total triterpenoids of apple peel and apple flesh from different apple varieties was measured by UV-VIS spectrophotometry method. The linear equation was y=0.007x-0.035(R2=0.999 3), and the calibration curve was linear in the range of 21μg-136μg. The average recovery was 100.32 %. The content of total triterpenoids in apple peel and apple flesh of different cultivars were in the range of 13.2 mg/g-23.9 mg/g and 8.0 mg/g-15.0 mg/g respectively. The method is simple and reliable, also had the advantages of stableness and repeatability,and can be used to detect the content of apple total triterpenoids.%建立测定苹果中总三萜含量的方法。以熊果酸为标准品,用紫外-可见分光光度法测定不同品种苹果果皮和果肉中总三萜的含量。熊果酸的质量在21μg~136μg范围内与吸光度呈良好的线性关系,线性回归方程为y=0.007x-0.035(R2=0.9993),平均回收率为100.32%。不同品种苹果果皮的总三萜的含量范围为13.2 mg/g~23.9 mg/g,苹果果肉的总三萜的含量范围为8.0 mg/g~15.0 mg/g。该方法简单、可靠、稳定性好、重复性高,可用于苹果中功能营养成分总三萜含量的检测。

  1. Novel triterpenoid AECHL-1 induces apoptosis in breast cancer cells by perturbing the mitochondria-endoplasmic reticulum interactions and targeting diverse apoptotic pathways.

    Science.gov (United States)

    Sawant, Mithila A; Dasgupta, Aparajita; Lavhale, Manish S; Sitasawad, Sandhya L

    2016-06-01

    The modus operandi for an anti-cancer drug must allow for an efficient discrimination system between tumorigenic and non-tumorigenic cells. Targeting ER stress and mitochondrial function in cancer cells appears to be a suitable option, as these processes are dysregulated in tumor cells. AECHL-1, a novel triterpenoid, exhibits potent anticancer activity against an array of cancer cell lines however, its mechanism of action remains elusive. Molecular targets of AECHL-1 were investigated using breast adenocarcinoma cells MCF-7, MDA-MB-231 and mammary epithelial cell line MCF 10A in vitro and xenograft tumors in SCID mice in vivo. Western blotting, flow cytometry, and immunohistochemical studies were employed to delineate the molecular pathways. AECHL-1 caused a transient elevation of ER stress proteins along with a prolonged phosphorylation of eIF2α in breast cancer cells. This was accompanied by a simultaneous release of calcium from ER stores and subsequent mitochondrial accumulation. These effects could be reversed by using ER stress inhibitors. AECHL-1 brings about mitochondria mediated, caspase independent cell death via AIF in MCF-7 cells; MDA-MB-231 succumbed to caspase dependent extrinsic pathway. Xenograft studies closely echoed our in vitro results. AECHL-1 did not alter cellular and molecular parameters in MCF 10A. These findings reveal that, AECHL-1 targets the Achilles Heel of cancer cell, namely dysfunctional ER and mitochondria while being non toxic to normal parenchyma and can thus be further explored as a potential chemotherapeutic intervention. Aggravation of ER stress by AECHL-1 uncovers a novel pathway for selective elimination of cancer cells. Copyright © 2016 The Authors. Published by Elsevier B.V. All rights reserved.

  2. New triterpene and triterpenoid glycosides from Ilex brevicuspis Novos triterpenos e glicosídeos triterpenóides de Ilex brevicuspis

    Directory of Open Access Journals (Sweden)

    Alexandre T. Cardoso Taketa

    2002-06-01

    Full Text Available From the leaves of Ilex brevicuspis were isolated a new triterpene, 20(S-3β, 19α-dihydroxyurs-12-en-23, 28-dioic acid, named here brevicuspic acid, and two new triterpenoid glycosides, 3-O-α-Larabinopyranosyl-20(S-pomolic acid-28-O-β-D-glucopyranosyl ester, named brevicuspisaponin 3, and the 23-sodium salt of (20S3β, 19α, 24-trihydroxyurs-12-en-23, 28-dioic acid-28β-O-β-Dglucopyranosyl ester, along with the known compound 3-O-α-Larabinopyranosyl-20(S-19α, 24-dihydroxyursolic acid- 28-O-β-Dglucopyranosyl ester, already described for Ilex argentina. Their structures were established on the basis of chemical and spectroscopic methods.Das folhas de Ilex brevicuspis foram isolados e identificados um novo triterpeno, ácido 20(S-3β, 19α-diidroxiurs-12-en-23, 28-dióico, denominado ácido brevicúspico, e dois novos glicosídeos, éster 28-O-β-Dglicopiranosil do ácido 3β-O-α-L-arabinopiranosil 20(S-pomólico e o sal sódico em C-23 do ester 28β-O-β D-glicopiranosil do ácido (20S- 3β, 19α, 24-triidroxiurs-12-en-23, 28-dióico. Foi isolado ainda o éster 28-O-β-D-glicopiranosil do ácido 3β-O-α-L-arabinopiranosil-20(S-19α, 24-diidroxiursólico, já descrito anteriormente para a espécie Ilex argentina. As estruturas foram estabelecidas por métodos espectroscópicos e químicos.

  3. Apoptosis-mediated antiproliferative activity of friedolanostane triterpenoid isolated from the leaves of Garcinia celebica against MCF-7 human breast cancer cell lines

    Science.gov (United States)

    SUBARNAS, ANAS; DIANTINI, AJENG; ABDULAH, RIZKY; ZUHROTUN, ADE; NUGRAHA, PATRIA A.; HADISAPUTRI, YUNI E.; PUSPITASARI, IRMA M.; YAMAZAKI, CHIHO; KUWANO, HIROYUKI; KOYAMA, HIROSHI

    2016-01-01

    The leaves of Garcinia celebica strongly inhibit the proliferation of MCF-7 human breast adenocarcinoma cell lines. The present study focused on investigating the active anticancer and antiproliferative compound from the G. celebica leaves and assessing its mechanism of action. Ethanol extracts of G. celebica were fractionated based on their polarity using n-hexane, ethyl acetate and water. The antiproliferative properties were tested in vitro against MCF-7 human breast cancer cell lines using the 3-(4,5-dimethylthiazolyl-2)-2,5-diphenyltetrazolium bromide assay. The active compound was subsequently isolated using column chromatography and identified by nuclear magnetic resonance. The characterized compound was also tested for its antiproliferative properties and the mechanism by which it induces apoptosis in MCF-7 cells by western blot analysis of the activated apoptotic proteins. This resulted in the isolation of a friedolanostane triterpenoid, which was determined to be methyl-3α, 23-dihydroxy-17,14-friedolanstan-8,14,24-trien-26-oat. This compound inhibited MCF-7 cell proliferation in a time- and dose-dependent manner with IC50 values of 82 and 70 µM for the 24 and 48 h treatments, respectively. Furthermore, the western blot analysis suggested that the compound exerted its anticancer activities by promoting apoptosis through the inhibition of the oncogenic protein Akt, thereby increasing the expression of poly (ADP-ribose) polymerase (PARP) protein. These results suggest that methyl-3α,23-dihydroxy-17,14-friedolanstan-8,14,24-trien-26-oat is the anticancer compound found in G. celebica, providing a basis for its potential use in cancer disease management. PMID:26870339

  4. 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

  5. A novel triterpenoid isolated from the root bark of Ailanthus excelsa Roxb (Tree of Heaven), AECHL-1 as a potential anti-cancer agent.

    Science.gov (United States)

    Lavhale, Manish S; Kumar, Santosh; Mishra, Shri Hari; Sitasawad, Sandhya L

    2009-01-01

    We report here the isolation and characterization of a new compound Ailanthus excelsa chloroform extract-1 (AECHL-1) (C(29)H(36)O(10); molecular weight 543.8) from the root bark of Ailanthus excelsa Roxb. The compound possesses anti-cancer activity against a variety of cancer cell lines of different origin. AECHL-1 treatment for 12 to 48 hr inhibited cell proliferation and induced death in B16F10, MDA-MB-231, MCF-7, and PC3 cells with minimum growth inhibition in normal HEK 293. The antitumor effect of AECHL-1 was comparable with that of the conventional antitumor drugs paclitaxel and cisplatin. AECHL-1-induced growth inhibition was associated with S/G(2)-M arrests in MDA-MB-231, MCF-7, and PC3 cells and a G(1) arrest in B16F10 cells. We observed microtubule disruption in MCF-7 cells treated with AECHL-1 in vitro. Compared with control, subcutaneous injection of AECHL-1 to the sites of tumor of mouse melanoma B16F10 implanted in C57BL/6 mice and human breast cancer MCF-7 cells in athymic nude mice resulted in significant decrease in tumor volume. In B16F10 tumors, AECHL-1 at 50 microg/mouse/day dose for 15 days resulted in increased expression of tumor suppressor proteins P53/p21, reduction in the expression of the oncogene c-Myc, and downregulation of cyclin D1 and cdk4. Additionally, AECHL-1 treatment resulted in the phosphorylation of p53 at serine 15 in B16F10 tumors, which seems to exhibit p53-dependent growth inhibitory responses. The present data demonstrate the activity of a triterpenoid AECHL-1 which possess a broad spectrum of activity against cancer cells. We propose here that AECHL-1 is a futuristic anti-cancer drug whose therapeutic potential needs to be widely explored for chemotherapy against cancer.

  6. Simultaneous estimation of three triterpenoids-ursolic acid, β-sitosterol and lupeol from flowers, leaves and formulations of Rhododendron arboreum Smith. using validated HPTLC method

    Directory of Open Access Journals (Sweden)

    Sunita Shilajan

    2013-01-01

    Full Text Available Background: This paper enfolds a rapid and sensitive high-performance thin-layer chromatographic (HPTLC method for the simultaneous estimation of three triterpenoids namely ursolic acid, β-sitosterol and lupeol from the leaves, flowers and herbal formulations of Rhododendron arboreum Smith., an ethnomedicinal Himalayan tree. All the three phytoconstituents have high therapeutic value. Aims and Objectives: The main aim is to separate, resolve and simultaneously quantitate the three markers-ursolic acid, β-sitosterol and lupeol from R. arboreum using normal phase HPTLC. Materials and Methods: Separation was performed on TLC aluminium plates precoated with silica 60 F 254 followed by detection of ursolic acid, β-sitosterol and lupeol carried out by derivatizing the plate with 10% methanolic sulphuric acid reagent followed by heating at 110΀C for 7 min. Camag TLC scanner 4 equipped with winCATS software was used for densitrometric scanning at 366 nm. The proposed method was further validated in terms of linearity, precision, accuracy and sensitivity as per the International Conference on Harmonisation (ICH guidelines. Results: A good linear relationship was obtained for the calibration plots with r 2 = 0.999, 0.993 and 0.995 for ursolic acid, β-sitosterol and lupeol, respectively. Accuracy of the method was checked by recovery study conducted at three different levels with the average recovery between 95% and 98% for all the three markers. Conclusion: The developed method can be used for the assessment of the quality of botanicals in terms of bioactive content.

  7. 狭叶南五味子中的抗生育活性三萜酸(英文)%Antifertility Triterpenoid Acids from Kadsura angustifolia

    Institute of Scientific and Technical Information of China (English)

    陈业高; 林中文; 曹霖; 孙汉董; 秦国伟; 谢毓元

    2002-01-01

    To isolate and characterize bioactive compounds from the stems of Kadsura angustifolia.METHOD:The compounds were extracted with solvent ,isolated by column chromatography and identified by the spectroscopic methods. RESULTS :eight compounds and a mixture of two triterpenoid acids were isolated and identified as epi-anwuweizic acid ( 1 ), shikimic acid (2), ( + )-catechin ( 3 ), po riferast- 5-en- 3β, 7α-diol (4), β-sitosterol ( 5 ), daucosterol ( 6 ), cerotic acid 1-monoglyceride (7) and behenic acid 1-monoglyceride (8),and mixiture of coccinic acid (9) and anwuweizonic acid (10). CONCLUSION :Mixture of 9 and 10 showed significant inhibitory activity against human decidual cells and rat luteal cells in vitro.Compounds 2~4,7 and 8 were first reported in the family Schisandraceae,and compounds 1,5,6,9 and 10 were isolated from K. angustifolia for the first time.%目的:从狭叶南五味子茎中分离鉴定生物活性成分.方法:采用溶剂提取及柱色谱法进行分离,光谱技术鉴定化合物的结构.结果:分得8个已知化合物及两个三萜酸的混合物,结构鉴定为表安五酸(epi-anwuweizic acid,1),莽草酸(shikimicacid,2),儿茶精((+)-catechin,3),poriferast-5-en-3β,7a-diol(4),β-谷甾醇(5),胡萝卜甙(6),cerotic acid l-monoglyceride(7),behenic acid l-monoglyceride(8)及coccinic acid(9)和安五酸(anwuweizonic acid,10)的混合物.结论:9和10的混合物体外时人蜕膜细胞和鼠黄体细胞有显著抑制作用.化合物2~4,7和8首次自五味子科植物中分得,化合物1,5,6,9和10首次分自本植物.

  8. A novel triterpenoid isolated from the root bark of Ailanthus excelsa Roxb (Tree of Heaven, AECHL-1 as a potential anti-cancer agent.

    Directory of Open Access Journals (Sweden)

    Manish S Lavhale

    Full Text Available BACKGROUND: We report here the isolation and characterization of a new compound Ailanthus excelsa chloroform extract-1 (AECHL-1 (C(29H(36O(10; molecular weight 543.8 from the root bark of Ailanthus excelsa Roxb. The compound possesses anti-cancer activity against a variety of cancer cell lines of different origin. PRINCIPAL FINDINGS: AECHL-1 treatment for 12 to 48 hr inhibited cell proliferation and induced death in B16F10, MDA-MB-231, MCF-7, and PC3 cells with minimum growth inhibition in normal HEK 293. The antitumor effect of AECHL-1 was comparable with that of the conventional antitumor drugs paclitaxel and cisplatin. AECHL-1-induced growth inhibition was associated with S/G(2-M arrests in MDA-MB-231, MCF-7, and PC3 cells and a G(1 arrest in B16F10 cells. We observed microtubule disruption in MCF-7 cells treated with AECHL-1 in vitro. Compared with control, subcutaneous injection of AECHL-1 to the sites of tumor of mouse melanoma B16F10 implanted in C57BL/6 mice and human breast cancer MCF-7 cells in athymic nude mice resulted in significant decrease in tumor volume. In B16F10 tumors, AECHL-1 at 50 microg/mouse/day dose for 15 days resulted in increased expression of tumor suppressor proteins P53/p21, reduction in the expression of the oncogene c-Myc, and downregulation of cyclin D1 and cdk4. Additionally, AECHL-1 treatment resulted in the phosphorylation of p53 at serine 15 in B16F10 tumors, which seems to exhibit p53-dependent growth inhibitory responses. CONCLUSIONS: The present data demonstrate the activity of a triterpenoid AECHL-1 which possess a broad spectrum of activity against cancer cells. We propose here that AECHL-1 is a futuristic anti-cancer drug whose therapeutic potential needs to be widely explored for chemotherapy against cancer.

  9. Comparative analysis of triterpenoids from Mikania cordifolia collected from four different locations Análise comparativa de triterpenóides de Mikania cordifolia coletada em quatro locais diferentes

    Directory of Open Access Journals (Sweden)

    Patrícia Abrão de Oliveira

    2006-12-01

    Full Text Available The species Mikania cordifolia is distributed across America and widely found throughout Brazilian territory, where is popularly used against snake bites. Methanolic and dichloromethanic extracts prepared from M. cordifolia Robinson collected from four different locations in Brazil were submitted to liquid-liquid extraction and the hexanic phase and residues obtained from this step were analyzed for triterpenoids by gas chromatography. The specimens from Ribeirão Preto-SP and São Carlos-SP showed similar triterpenoid composition: alpha-amyrin, lupeol, lupenone, alpha-amyrin acetate, beta-amyrin acetate, lupeol acetate, taraxasterol acetate, campesterol and beta-sitosterol. Besides these triterpenoids, the specimen from Campos de Jordão-SP presented 11-oxours-12-ene, 11-oxoolean-12-ene and taraxerol acetate, and from Monte Verde, epitaraxerol e taraxerol acetate. The triterpene friedelin could be found in specimens from Ribeirão Preto and São Carlos.A espécie Mikania cordifolia distribui-se por toda a América e é amplamente encontrada em quase todo o território brasileiro, onde é utilizada popularmente contra mordidas de serpentes. Extratos metanólicos e diclorometânicos preparados a partir e M. cordifolia Robinson coletadas em quatro locais diferentes do Brasil foram submetidos à extração líquido-líquido e os extratos hexânicos e resíduos obtidos nesta etapa foram analisados para a pesquisa de triterpenóides por cromatografia em fase gasosa. Os espécimes coletados em Ribeirão Preto-SP e São Carlos-SP apresentaram os triterpenóides beta-amirina, lupeol, lupenona, acetato de alfa-amirina, acetato de beta-amirina, acetato de lupeol, acetato de taraxasterol, campesterol e beta-sitosterol na suas composições. Além destes trierpenóides, o espécime de Campos de Jordão-SP apresentou 11-oxours-12-eno, 11-oxoolean-12-eno e acetato de taraxerol e, o de Monte verde-MG, epitaraxerol e acetato de taraxerol. A friedelina foi

  10. Gymnemic Acid Stimulates In Vitro Splenic Lymphocyte Proliferation.

    Science.gov (United States)

    Singh, Vineet Kumar; Dwivedi, Padmanabh; Chaudhary, B R; Singh, Ramesh

    2016-02-01

    Gymnemic acid is a mixture of triterpenoid saponins of oleanane class, isolated from Gymnema sylvestre Wild R.Br (family: Asclepidaceae), an herbal plant used in traditional medicine to treat diabetes. Effect of gymnemic acid (0.1-20 µg/mL) on in vitro mitogen (concanavalin A and lipopolysaccharide)-induced splenic lymphocyte proliferation was studied using rat as model. Significant (p sylvestre is scientifically supplemented with its immunomodulatory properties.

  11. Terpenoids and Steroids from Euphorbia hypericifolia.

    Science.gov (United States)

    Zhao, Jin-Xin; Shi, Shan-Shan; Sheng, Li; Li, Jia; Yue, Jian-Min

    2015-12-01

    Two new triterpenoids and two new sterols, named euphyperins A-D (1-4), including an oleanane-type triterpenoid (1), a lupane-type nortriterpenoid (2), and two cholestane-type steroids (3 and 4), along with five known compounds (5-9) were isolated from the twigs and leaves of Euphorbia hypericifolia. Euphyperin B (2) represents a rare lupane-type nortriterpenoid, and euphyperin C (3) is a novel 8,14-secocholestane-type steroid. Euphyperin A (1) exhibited moderate PTP1B inhibitory activity with an IC50 = 17.05 ± 1.12 μg/mL.

  12. Rapid profiling and identification of triterpenoid saponins in crude extracts from Albizia julibrissin Durazz. by ultra high-performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry.

    Science.gov (United States)

    Han, Lifeng; Pan, Guixiang; Wang, Yuefei; Song, Xinbo; Gao, Xiumei; Ma, Baiping; Kang, Liping

    2011-07-15

    Ultra high-performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry (UHPLC/ESI-Q-TOF-MS/MS) was applied to separate and identify triterpenoid saponins in crude extract from the stem bark of Albizia julibrissin Durazz. The molecular weights were determined by comparing quasi-molecular ions [M+NH(4)](+) in positive mode and [M-H](-) and [M-2H](2-) ions in negative mode. The MS/MS spectra of the [M-H](-) ions for saponins provided a wealth of structural information related to aglycone skeletons, sugar types and linked sequence. On the basis of the fragmentation behavior of known saponins isolated before, saponins from this plant were identified, even though references were not available. As a result, a total of twenty-eight saponins in the crude extract were identified, which all had a common basic skeleton of the triterpene oleanolic acid and eight of them were new compounds.

  13. Study on extraction technology and antioxidative activity of polysaccharides and triterpenoids from peel of Poria cocos%茯苓皮多糖和三萜类物质提取及其抗氧化活性研究

    Institute of Scientific and Technical Information of China (English)

    陈红梅

    2015-01-01

    采用超声辅助提取法分别从茯苓皮中提取多糖和三萜类物质。考察提取溶剂、超声功率、液料比、提取温度、提取时间等对茯苓皮多糖和三萜类物质的影响。结果表明,选用乙醇提取多糖,选用乙酸乙酯浸提三萜类物质,最佳提取条件为:超声功率450 W,液料比为45 mL/g,提取温度80℃,提取时间35 min。通过对DPPH自由基清除作用、还原力、羟基自由基清除作用的测定,评价茯苓皮中多糖和三萜类物质的抗氧化活性。结果表明,抗氧化能力与质量浓度存在量效关系。在质量浓度达到0.4 mg/mL时,茯苓皮多糖和三萜类物质提取液对DPPH和羟基自由基的清除能力均高于VC;茯苓皮三萜类物质提取液还原力与VC相当。茯苓皮提取物作为一种天然的抗氧化剂具有良好的应用前景。%Microwave assisted extracting conditions of polysaccharides and triterpenoids from peel of Poria cocos were studied.The in-fluence of extraction solvent , solvent-material ratio , ultrasonic power , temperature , extraction time was evaluated by single factor ex-periments.The results showed that the polysaccharides were obtained by ethanol , while the triterpenoids was obtained by ethyl acetate . The optimal conditions were as follows .Ultrasonic power 450 W;solvent-material ratio , 45 mL/g;temperature , 80℃;and extraction time, 35 min.The antioxidant activity was evaluated based on DPPH radical scavenging capacity , reducing power and hydroxyl free radical scavenging capacity .The ability of antioxidative activity was increased with the inerease concentrations of polysaccharides and triterpenoids.When extracted at the concentration of 0.4 mg/mL, polysaccharides and triterpenoids revealed relatively better DPPH radical scavenging capacity and hydroxyl free radical scavenging capacity than V C .Reducing power of riterpenoids was comparable to those of V C .Therefore , the peel of Poria cocos

  14. Chemical constituents of triterpenoid saponins from Glycyrrhiza uralensis%乌拉尔甘草皂苷类成分研究

    Institute of Scientific and Technical Information of China (English)

    陶伟伟; 段金廒; 杨念云; 李建萍; 唐于平; 严辉

    2013-01-01

    目的 研究乌拉尔甘草Glycyrrhiza uralensis根及根茎的化学成分.方法 应用溶剂法和色谱法进行分离纯化,利用波谱技术鉴定化合物结构;并测试化合物的细胞毒活性.结果 从乌拉尔甘草50%乙醇提取物中分离得到14个皂苷类化合物,分别鉴定为uralsaponin C(1)、uralsaponin D(2)、licorice-saponin A3 (3)、uralsaponin F (4)、22β-acetoxyl-glycyrrizin (5)、24-hydroxyl-licorice-saponin E2 (6)、licorice-saponin E2 (7)、licorice-saponin G2 (8)、22β-acetoxyl-glyrrhaldehyde (9)、3β-O-[β-D-glucuronopyranosyl-(1→2)-β-D-glucuronopyranosyl]-glycyrretol (10)、araboglycyrrhizin(11)、licorice-saponin J2 (12)、甘草酸(13)、单葡糖醛酸基甘草次酸(14).化合物1~14对3种人源肿瘤细胞MGC-803、SW620、SMMC-7721的半数抑制率(IC50)均大于100 μmol/L,化合物2、6~8、13的水解后苷元对3种人源肿瘤细胞的抑制率为18.3~41.6 μmol/L.结论 化合物14是一个新的天然产物,化合物11为首次从该植物中分离得到;化合物1~14对3种人源肿瘤细胞MGC-803、SW620、SMMC-7721均无显著的细胞毒活性,化合物2、6~8、13水解后苷元细胞毒活性增强.%Objective To study the chemical constituents from the roots and rhizomes of Glycyrrhiza uralensis.Methods The compounds were separated and purified by solvent and chromatographic methods.Their structures were identified by spectroscopic techniques.Results Fourteen triterpenoid saponins isolated from 50% ethanol extract of the roots and rhizomes of G uralensis were identified as uralsaponin C (1),uralsaponin D (2),licorice-saponin A3 (3),uralsaponin F (4),22β-acetoxyl-glycyrrizin (5),24-hydroxyl-licorice-saponin E2 (6),licorice-saponin E2 (7),licorice-saponin G2 (8),22β-acetoxyl-glyrrhaldehyde (9),3β-O-[β-D-glucuronopyranosyl-(1→2)-β-D-glucuronopyranosyl]-glycyrretol (10),araboglycyrrhizin (11),licorice-saponin J2 (12),glycyrrhizin (13),and glycyrrhetic acid monoglucuronide (14

  15. 翼茎羊耳菊三萜类化学成分研究%Studies on Triterpenoid Saponins from Inula Pterocaula

    Institute of Scientific and Technical Information of China (English)

    太志刚; 陈安逸; 秦本逵; 蔡乐; 徐艳群

    2014-01-01

    To obtain a more comprehensive understanding on its effective components,triterpenoidal saponins are studied from the root of inula pterocaula.The chemical constituents are isolated by silica gel,Sephadex LH-20, and Rp-18 column chromatographies.Their structures are then elucidated by chemical and spectral methods. Twelve compounds are isolated,and their structures are identified asβ-amyrin(1),erythordiol(2),Ursolic acid (3),oleanolic acid(4),2β,3β,23α-trihyroxyolean-12-en-28 -acid(5),oleanoic acid 28 -O-β-D-glucopyranosyl ester(6),oleanoic acid 3-O-β-D-glucopyranoside(7),oleanoic acid 3-O-(β-D-glu-copyranosyl)-28-O-β-D-glucopyranosyl ester(8 ),2β-hydroxyolean-3 -O-(β-D-glucopyranosy-loxy)-12-en-23,28-dioicacid(9),3 -O-β-glucopyranosyl-(1→4)-β-D-glucuronopyranoside -23-hydroxyolean-12-en-28-oic acid 28-O-β-D-glucopyranosyl ester(10),3-O-β-D-glucopyr-anosyl pomolic acid-28-O-β-D-glucopyranosylester(11),and 3 -O-α-L-arabinpyranosyl-20,19, 24-trihydroxy ursolic acid(12).All above compounds are obtained from this plant for the first time.Results of the trial can provide references for further study of inula pterocaula.%研究翼茎羊耳菊(Inula pterocaula)根部三萜类化学成分,阐明其药效物质基础。采用Sepha-dex LH-20凝胶材料、Rp-18反向材料和硅胶进行化合物分离,利用现代光谱技术和理化性质鉴定化合物结构。并从中分离得到12个三萜类化学成分,分别鉴定为β-香树脂醇(1)、赤藓糖醇(2)、乌苏酸(3)、齐墩果酸(4)、2β,3β,23α-三羟基-28-齐墩果酸(5)、齐墩果酸-28-O-β-D-吡喃葡萄糖苷(6)、齐墩果酸-3-O-β-D-吡喃葡萄糖苷(7)、齐墩果酸-3-O-(β-D-吡喃葡萄糖)-28-O-β-D-吡喃葡萄糖苷(8)、2β-羟基-3-O-β-D-吡喃葡萄糖-23,28-二齐墩果酸(9)、3-O-β-吡喃葡萄糖-(1→4)-β-D-吡喃葡萄糖醛基-23-羟基-齐墩果酸-28-O-β-D-吡喃葡萄糖苷(10)、3-O

  16. Triterpenoid saponins from Gynostemma pentaphyllum.

    Science.gov (United States)

    Shi, Lin; Cao, Jia-Qing; Shi, Sheng-Ming; Zhao, Yu-Qing

    2011-02-01

    Four new dammarane-type triterpene saponins, 1-4, were isolated from the aerial parts of Gynostemma pentaphyllum (Thunb.) Makino. Their structural elucidations were accomplished mainly on the basis of spectroscopic methods, such as IR, HR-TOF-MS, and NMR. Compounds 1-4 showed moderate cytotoxic activities against cancer cell lines HL-60, Colon205, and Du145 in vitro.

  17. Triterpenoid saponins from Cortex Albiziae

    OpenAIRE

    Zou, Kun; Zhao, Yuying

    2004-01-01

    Cortex Albiziae, the dried stem bark of a leguminous plant, Albizia julibrissin Durazz, was specified in Chinese Pharmacopoeia (1995 edit.) as a traditional Chinese medicine to be used.to relieve melancholia and uneasiness of body and mind, to invigorate the circulation of blood and subside a swelling. In a course of our quality assessment of traditional Chinese medicines, the n-BuOH soluble part of 95% EtOH extracts from the stem barks of Albizia julibrissin was subjected to a series of sol...

  18. 光照和种源对青钱柳叶三萜类化合物积累的影响%Influence of illumination intensity and provenance on triterpenoid accumulation in the leaves of Cyclocarya paliurus seedlings

    Institute of Scientific and Technical Information of China (English)

    李彦; 周晓东; 方升佐; 邓波; 尚旭岚; 杨万霞

    2015-01-01

    Based on the seedlings of Cyclocarya paliurus ( 1-year stem with 2 year root system) , split-split plot design with three C. paliurus provenances ( Wufeng, Yuanling and Muchuan) and three light conditions ( full sunlight, 50%full sunlight and 15% full sunlight) was adopted to compare the content variation of total triterpenoid, arjunolic acid and cyclocarioside I in the leaves of C. paliurus seedlings under different treatments. Meanwhile, the seasonal variation of triterpenoid contents in the leaves was also discussed. The results showed that there were significant differences in triter?penoid accumulation in leaves of C. paliurus seedlings among different treatments when October is defined as leaf harvest time. The highest content of total triterpenoids (42.03 mg/g) was obtained in the treatment of Yuanling provenance with full sunlight, while the greatest contents of arjunolic acid and cyclocarioside I were achieved under the treatments of Mu?chuan provenance with 15% of full sunlight and Muchuan provenance with full sunlight, reaching 4.42 mg/g and 2.52 mg/g, respectively. The greatest production of total triterpenoids and cyclocarioside I was obtained in the treatment of Muchuan provenance with full sunlight, reaching 2 907. 2 and 264.4 mg/plant respectively. However, the highest pro?duction of arjunolic acid was observed in the treatments of Yuanling provenance with 50% of full sunlight, hitting to 208. 6 mg/plant. The accumulation of triterpenoids in the leaves of Cyclocarya paliurus are closely related to provenance, illumination intensity and the harvest time of leaves. Results from this study would provide some important practical and theoretical bases for effectively managing the plantations of C. paliurus.%以青钱柳二根一干苗为研究对象,采用裂区设计研究了3种光照条件(全光照、50%全光照、15%全光照)和3个种源(五峰、沅陵、沐川)对青钱柳叶中总三萜、阿江榄仁酸和青钱柳甙Ⅰ含量的影响,探

  19. 黑灵芝中性提取物三萜含量测定及抗氧化作用研究%Triterpenoids Content and Antioxidant Activity of Neutral Components from Ganoderma Atrum

    Institute of Scientific and Technical Information of China (English)

    刘晓珍; 聂少平; 李文娟; 陈奕; 谢明勇

    2011-01-01

    采用分光光度法在550 nm波长下以齐墩果酸为对照品测定黑灵芝中性提取物中总三萜含量,测得黑灵芝中性组分中三萜含量为40.92%,RSD为3.28%,平均加标回收率为103.9%.通过对DPPH自由基清除作用、总还原能力、对β-胡萝卜素-亚油酸的抑制作用和对亚铁离子螯合能力的测定,评估了黑灵芝中性组分的抗氧化性.结果表明:它具有较强的抗氧化性.另外,用Folin-Ciocalteu酚方法测得黑灵芝中性组分的总酚含量为31 mg/g中性组分.据此,为黑灵芝质量评价及其中性组分开发应用提供一定的理论指导.%Triterpenoids content of neutral components extracted from Ganoderma atrum was determined by spectrophotometry at 550 nm. The triterpenoids content of the neutral components was 40. 92% with RSD =3. 32% , and its recovery was 103. 9% . The antioxidant capacity of the extract was assessed by scavenging effects on 2,2-di-phenyl-1-picrylhydrazyl radicals ( DPPH), reducing power assay, f$-carotene bleaching assay and metal chelating activity on ferrous ions. The results indicated that the neutral components isolated from Ganoderma atrum had significant antioxidant activity. Total phenols content determined by Folin-Ciocalteu colorimetric method was 0. 31 mg/g neutral components. It will provide certain theoretical guidance for the quality evaluation and application of Ganoderma atrum.

  20. Pseudomonas aeruginosa Biofilm Formation and Persistence, along with the Production of Quorum Sensing-Dependent Virulence Factors, Are Disrupted by a Triterpenoid Coumarate Ester Isolated from Dalbergia trichocarpa, a Tropical Legume

    Science.gov (United States)

    Pottier, Laurent; Huet, Joelle; Rabemanantsoa, Christian; Kiendrebeogo, Martin; Andriantsimahavandy, Abel; Rasamindrakotroka, Andry; Stévigny, Caroline; Duez, Pierre; El Jaziri, Mondher

    2015-01-01

    Recently, extracts of Dalbergia trichocarpa bark have been shown to disrupt P. aeruginosa PAO1 quorum sensing (QS) mechanisms, which are key regulators of virulence factor expression and implicated in biofilm formation. One of the active compounds has been isolated and identified as oleanolic aldehyde coumarate (OALC), a novel bioactive compound that inhibits the formation of P. aeruginosa PAO1 biofilm and its maintenance as well as the expression of the las and rhl QS systems. Consequently, the production of QS-controlled virulence factors including, rhamnolipids, pyocyanin, elastase and extracellular polysaccharides as well as twitching and swarming motilities is reduced. Native acylhomoserine lactones (AHLs) production is inhibited by OALC but exogenous supply of AHLs does not restore the production of virulence factors by OALC-treated cultures, indicating that OALC exerts its effect beyond AHLs synthesis in the QS pathways. Further experiments provided a significant inhibition of the global virulence factor activator gacA by OALC. OALC disorganizes established biofilm structure and improves the bactericidal activity of tobramycin against biofilm-encapsulated PAO1 cells. Finally, a significant reduction of Caenorhabditis elegans paralysis was recorded when the worms were infected with OALC-pre-treated P. aeruginosa. Taken together, these results show that triterpenoid coumarate esters are suitable chemical backbones to target P. aeruginosa virulence mechanisms. PMID:26186595

  1. Microcrystalline cellulose based matrix solid phase dispersion microextration for isomeric triterpenoid acids in loquat leaves by ultrahigh-performance liquid chromatography and quadrupole time-of-flight mass spectrometry.

    Science.gov (United States)

    Cao, Jun; Peng, Li-Qing; Xu, Jing-Jing

    2016-11-11

    An analytical procedure based on matrix solid phase dispersion (MSPD) microextration and ultrahigh-performance liquid chromatography coupled with quadrupole time-of-flight tandem mass spectrometry was developed for the determination of isomeric triterpenoid acids (maslinic acid, corosolic acid, oleanolic acid and ursolic acid) in loquat leaves. Microcrystalline cellulose was used for the first time as a solid sorbent in MSPD microextration. Compared with the traditional extraction methods, the proposed method possessed the advantages of shorter extraction time, and lower consumption of sample, sorbent and organic solvent. The MSPD parameters that influenced the extraction efficiency of isomeric analytes were investigated and optimized in detail. Under the optimized conditions, good linearity was obtained with correlation coefficients higher than 0.9990. The limits of detection and quantification were 19.6-51.6μg/kg and 65.3-171.8μg/kg, respectively. Meanwhile, the recoveries obtained for all the analytes were ranging from 90.1% to 107.5%. Finally, the optimized method was successfully applied for analyzing these isomeric acids in loquat leaves samples obtained from different cultivated areas.

  2. Ursolic acid, a natural pentacyclic triterpenoid, inhibits intracellular trafficking of proteins and induces accumulation of intercellular adhesion molecule-1 linked to high-mannose-type glycans in the endoplasmic reticulum

    Directory of Open Access Journals (Sweden)

    Satoshi Mitsuda

    2014-01-01

    Full Text Available Ursolic acid (3β-hydroxy-urs-12-en-28-oic acid is a natural pentacyclic triterpenoid that is present in many plants, including medicinal herbs, and foods. Ursolic acid was initially identified as an inhibitor of the expression of intercellular adhesion molecule-1 (ICAM-1 in response to interleukin-1α (IL-1α. We report here a novel biological activity: ursolic acid inhibits intracellular trafficking of proteins. Ursolic acid markedly inhibited the IL-1α-induced cell-surface ICAM-1 expression in human cancer cell lines and human umbilical vein endothelial cells. By contrast, ursolic acid exerted weak inhibitory effects on the IL-1α-induced ICAM-1 expression at the protein level. Surprisingly, we found that ursolic acid decreased the apparent molecular weight of ICAM-1 and altered the structures of N-linked oligosaccharides bound to ICAM-1. Ursolic acid induced the accumulation of ICAM-1 in the endoplasmic reticulum, which was linked mainly to high-mannose-type glycans. Moreover, in ursolic-acid-treated cells, the Golgi apparatus was fragmented into pieces and distributed over the cells. Thus, our results reveal that ursolic acid inhibits intracellular trafficking of proteins and induces the accumulation of ICAM-1 linked to high-mannose-type glycans in the endoplasmic reticulum.

  3. 响应面法优化超声辅助提取宣木瓜总皂苷提取工艺研究%Optimization of Ultrasound-assisted Extraction of Total Triterpenoid Saponins from Chaenomeles speciosa Using Response Surface Analysis

    Institute of Scientific and Technical Information of China (English)

    潘国波; 杨小明; 丁艳; 李媛媛; 韩邦兴

    2012-01-01

    对宣木瓜总皂苷的超声辅助提取工艺优化进行研究.在单因素试验基础上,选择提取时间、温度、乙醇浓度和料液比为自变量,以宣木瓜总皂苷得率为响应值,采用Central Composite Design试验设计方法,研究各自变量及其交互作用对宣木瓜总皂苷提取率的影响.利用Design Expert软件得到回归方程的预测模型并进行响应面分析,确定超声辅助提取宣木瓜总皂苷的最佳条件为时间61.69 min,温度62.34℃,乙醇浓度70.49%,料液比1∶30.57 g/mL,在此条件下,总皂苷提取率达到1.55%.验证实验表明,所得模型方程能较好地预测实验结果.%Response surface methodology was used to optimize the ultrasound-assisted extraction of total triterpenoid saponins from Chaenomeles speciosa. The extraction efficiency of total triterpenoid saponins was investigated with respecting to four variables including time, temperature, ethanol concentration and liquid-to-solid ratio. On the basis of a series of one-factor-at-a-tirrje experiments, a polynomial regression model equation was fitted by the combined use of Box-Behnken experimental design and regression analysis. By analyzing the regression model using response surface analysis,the optimum extraction conditions of total triterpenoid saponins from C. speciosa were identified as follows ;61.69 min extraction time,62. 34 ^extraction temperature,70. 49% ethanol concentration and 1 = 30.57 g/mL solid-to-liquid ratio,and the extration efficiency of total triterpenoid saponins was up to 1. 55% under the optimized conditions. Confirmatory experiments indicated the good prediction ability of the established model.

  4. 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.

  5. 灵芝三萜类化合物对AD衰老模型大鼠学习记忆能力和脑能量代谢的影响%Protective Effects and Mechanism of Ganoderma Lucidum Triterpenoids on Learning and Memory Function of Alzheimer Disease Model Animals

    Institute of Scientific and Technical Information of China (English)

    张玥; 罗俊; 黄能慧; 张小毅

    2012-01-01

    探讨了灵芝三萜类化合物(Ganoderma Lucidum Triterpenoids,GLT)对阿尔茨海默病(Alzheimer disease,AD)的防治作用及作用机制,为临床新药的开发和应用提供参考依据.结果表明AD自然衰老模型大鼠Morris水迷宫检测显示学习记忆障碍,脑组织Na+ -K+ -AT-Pase活力降低,GLT灌胃2月后,学习记忆成绩明显提高,Na+-K+-ATPase活力增加.提示GLT能提高AD自然衰老模型大鼠的学习记忆能力,其作用可能与改善脑内能量代谢有关.%In order to elucidate the protective effects and mechanism of Ganoderma Lucidum Triterpenoids (GLT) on Alzheimer Disease model animals, two different groups rats was divided, it was found that the model animals exhibited the worse ability in learning and memory and a lower Na+ - K+ - ATPase activity . The addition of GLT significantly improved the a-bove indexes(P<0. 05). GLT can protect AD model animals, GLT improved the learning and memory dysfunction in aging model rats, the following mechanism may be improving energy metabolism in brain.

  6. Optimization of Extraction Technology and Determina-tion of Total Triterpenoidic Acid from Sabia limonia-cea Wall.%瑶药毛萼清风藤中总三萜酸的提取工艺优化及含量测定

    Institute of Scientific and Technical Information of China (English)

    黄艳; 张春来; 刘布鸣

    2015-01-01

    Objective]To optimize extraction technology of total triterpenoidic acid from Sabia limoniacea Wall.and establish its content determination method.[Methods]The content of total triterpenoidic acid was determined by UV with the oleanoic acid as reference.The influ-ence of extracting method,concentration of ethanol,radio of liquid to material and extracting time on the total triterpenoidic acid of yield were evaluated by single factor experiments and orthogonal experiments.[Results]The optimum extraction were carried out at room tempera-ture with 50 times of the amount of 70% ethanol,5% vanillin 0.2 mL and perchloric acid 0.6 mL.After 15 min water bath at 70℃,the extracts were cooled,added 4 mL of acetic acid and determined at 545 nm.The content of total triterpenoidic acid was 13.76 mg/g.[Conclusion]The content of total triterpenoidic acid from Sabia limoniacea Wall.was relatively high,and this optimized technology was stable and feasi-ble.%【目的】优化瑶药毛萼清风藤(Sabia limoniacea wall.)中总三萜酸的提取工艺,并建立其含量测定方法。【方法】以齐墩果酸为对照品,采用紫外分光光度法测定瑶药毛萼清风藤中总三萜酸的含量。通过单因素试验和正交试验相结合的方法考察提取方法、提取溶剂、乙醇浓度、料液比、提取时间对毛萼清风藤中总三萜酸提取的影响。【结果】试验所用比色条件为5%香草醛溶液0.2 mL,高氯酸0.6 mL,水浴温度70℃,水浴时间15 min,检测波长545 nm;最佳提取工艺为50倍量70%乙醇,于常温下超声提取40 min;在此条件下所提取得到的平均总三萜酸含量为13.76 mg/g。【结论】瑶药毛萼清风中总三萜酸含量相对较高,所得的优选工艺稳定可行。

  7. 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)

  8. Five new terpenoids from the rhizomes of Isodon adenantha.

    Science.gov (United States)

    Zhou, Xing-Li; Xiao, Chao-Jiang; Wu, La-Bin; Huang, Bo; Dong, Xiang; Jiang, Bei

    2014-01-01

    Five new terpenoids including 2 labdane diterpenoids (1 and 2), 2 ent-kaurane diterpenoids (3 and 4), and a new oleanane triterpenoid (5), along with 13 known compounds (6-18), were isolated from the ethyl acetate fraction of 70% acetone extract of the rhizomes of Isodonadenantha. Their structures were elucidated based on the analyses of spectroscopic data and comparison of their physicochemical properties. The structure of 1 was further confirmed by single-crystal X-ray diffraction. Cytotoxicity and antibacterial activities of the samples were measured by MTT method and the filter paper disk agar diffusion method. But none of them showed significant activities.

  9. Triterpenoids and an alkamide from Ganoderma tsugae.

    Science.gov (United States)

    Lin, Kai-Wei; Maitraie, Dravidum; Huang, A-Mei; Wang, Jih-Pyang; Lin, Chun-Nan

    2016-01-01

    Ganoderma tsugae is a medicinal mushroom. In a continual study on the bioactive constituents of this fungus, a new lanostanoid, 3β-acetoxy-16α-hydroxy-24ξ-methyl-5α-lanosta-8,25-dien-21-oic acid, named tsugaric acid F (1) and a novel palmitamide, N-(3'α,4'β-dihydroxy-2'β-(hydroxymethyl)-1'β-(cyclobutyl)palmitamide (2) were isolated and characterized from the fruit bodies of G. tsugae, and three novel seco-lanostanoids, 3,4-seco-8α,9α-epoxy-5α-lanosta-21-oic acid 3,4 lactone (5), 3,4-seco-5β-lanosta-7,9(11),4(29)-trien-3,21-dioic acid-3-methyl ester (6), 3,4-seco-5β-lanosta-7,9(11),4(29)-trien-3,21-dioic acid (7), and a known compound, 3-oxo-5α-lanosta-8-en-21-oic acid (4) were prepared from 3. The structures of new compounds, 1, 2, 5-7 were determined by spectroscopic methods. Compounds 1 and 4 showed inhibitory effects on xanthine oxidase (XO) with an IC50 values of 313.3 ± 80.0 and 43.9 ± 29.9 μM, respectively when 7 exhibited potent inhibitory effect on superoxide anion generation in rat neutrophils stimulated with formyl-Met-Leu-Phe (fMLP)/cytochalasin B (CB) with an IC50 values of 1.3 ± 0.2 μM. Compounds 4-7 showed weak cytotoxic activities against PC3 cells. These results indicated that 4 and 7 may be used as cancer chemopreventive agents.

  10. Triterpenoids and Prevention of Prostate Cancer

    Science.gov (United States)

    2001-10-01

    constituents of rose-bay willow- herb . J. Chem. Soc. (C) biosynthesis of nitric oxide. J. Biol. Chem. 1994, 269, 13725- 1967, 510-515. 13728. (c) Anggard, E...cells were obtained from Dr. Gustav Lienhard (Dart- 1. Tang W, Eisenbrand G 1992 Chinese Drugs of Plant mouth Medical School, Hanover, NH). Cells were...2711-2714 tion of diabetic and obese mice to insulin by retinoid X 8. Suh N, Wang Y, Honda T, Gribble GW, Dmitrovsky E, receptor agonists. Nature 386

  11. Steroidal and triterpenoidal glucosides from Passiflora alata

    Directory of Open Access Journals (Sweden)

    Reginatto Flávio H.

    2001-01-01

    Full Text Available Five glycosides were isolated from leaves of P. alata. The structures 1-5 were obtained through extensive spectral analyses as 3-O-beta-D-glucopyranosyl-stigmasterol (1, 3-O-beta-D-glucopyranosyl-oleanolic acid (2, 3-O-beta-D-glucopyranosyl-(1->3-beta-D-glucopyranosyl-oleanolic acid (3, 3-O-beta-D-glucopyranosyl-(1->2-beta-D-glucopyranosyl-oleanolic acid (4 and 9,19-cyclolanost-24Z-en-3beta,21,26-trihydroxy-3,26-di-O-gentiobiose (5. Comparison of the TLC profiles of the hydroethanolic extracts from leaves of other Passiflora species found in the south of Brazil (P. actinia, P. caerulea, P. edulis var. flavicarpa, P. elegans, P. foetida, P. misera and P. tenuifila showed that only P. alata presented saponin accumulation.

  12. Two New Antioxidant Triterpenoids from Lonicera quinquelocularis

    Directory of Open Access Journals (Sweden)

    Dilfaraz Khan

    2014-03-01

    Full Text Available Two new tri terpenoids namely, 3α - hydroxyferna-7, 9(11,22-trien-12-one (1 and 3α - acetoxyferna-7, 9(11-dien-22-ol (2 along with two known compounds 3α,16α-dihydroxyferna-7,9(11-dien-12-one (3 and 3α,16α-dihydroxyfern a -8-en-11-one (4 were isolated from Lonicera quinquelocularis . Their structures were elucidated by chemical and modern spectroscopic techniques. All the compounds showed good antioxidant activities in the DPPH radical scavenging assay.

  13. A New Triterpenoid Saponin from Aidi Injection

    Institute of Scientific and Technical Information of China (English)

    ZHANG Miao-miao; LIU Yan-li; CHEN Zhong; LI Xiao-ran; XU Qiong-ming; YANG Shi-lin

    2012-01-01

    Objective To investigate the chemical constituents from Aidi Injection.Methods The chemical constituents were isolated by chromatography on Sephadex LH-20 gel columns and reverse phase semi-preparative HPLC repeatedly.Their structures were identified by spectroscopic analysis (NMR and MS).Results Twenty-two compounds were isolated and identified to be 3-O-3',4'-diacetyl-β-D-xylopyranosyl-6-O-β-D-glucopyranosylcycloastragenol (1),astragaloside IV (2),astragaloside Ⅱ (3),astragaloside I (4),isoastragaloside I (5),acetylastragaloside I (6),ginsenosid Re (7),ginsenoside Rf (8),ginsenoside Rg1 (9),ginsenoside Rb3 (10),notoginsenoside R4 (11),ginsenoside Rb1 (12),ginsenoside Rc (13),ginsenoside Rb2 (14),ginsenoside Rd (15),lucyoside H (16),3-O-ββ-D-glucopyranosyl(l→4)-β-D-glucopyranosyl(l→3)-α-L-rhamnopyranosyl (1→2)-α-Larabinopyranosyl oleanolic acid 28-O-α-L-rhamnopyranosyl(l→4)-β-D-glucopyranosyl(1→6)-β-D-glucopyranoside (17),3-O-β-D-glucopyranosyl(1→3)-α-L-rhamnopyranosyl [β-D-glucopyranosyl-(l→4)]-(l→2)-αt-L-arabinopyranosyl oleanolic acid 28-O-α-L-arabinopyranosyl(1→4)-β-D-glucopyranosyl(1→6)-β-D-glucopyranoside (18),syringin (19),elentheroside E (20),4-(1,2,3-trihydroxypropyl)-2,6-dimethoxyphenyl-I-O-β-D-glucopyranoside (21),and coniferin (22).Conclusion Compounds 1-6 are originated from Astragalus membranceus,compounds 7-18 are originated from Panax ginseng,and compounds 19-22 are originated from Acanthopanax senticosus by LC-MS analysis.Compound 1 is a new compound.

  14. A new triterpenoid saponin from Gynostemma pentaphyllum.

    Science.gov (United States)

    Shi, Lin; Meng, Xian-Jun; Cao, Jia-Qing; Zhao, Yu-Qing

    2012-01-01

    A new dammarane-type triterpene saponin was isolated from the aerial parts of Gynostemma pentaphyllum (Thunb.) Makino. Its structural elucidation was accomplished mainly on the basis of the interpretation of spectroscopic data, such as IR, HR-TOF-MS and NMR. Its cytotoxic activity was evaluated against one human cancer cell line HL-60 using MTT assay.

  15. Two New Triterpenoids from Saussurea petrovii

    Institute of Scientific and Technical Information of China (English)

    2001-01-01

    Two new taraxastane-type triterpenes, 3b, 21b-dihydroxyl-20(30)-en-taraxastane 1 and 3b, 30-dihydroxy-20(21)-en-taraxastane 2, were isolated from Saussurea petrovii. Their structures were elucidated by spectral methods (EIMS, IR, 1D and 2DNMR).

  16. SIGMOISIDE E: A NEW ANTIBACTERIAL TRITERPENOID ...

    African Journals Online (AJOL)

    Sigmoiside E exhibited antibacterial activity against gram-negative bacteria. ... The ethyl acetate extract after successive column chromatography and .... JEOLJMS-DX 303 mass spectrometer, collision gas Xe (ion gun conditions 6 kV and 10 ...

  17. Triterpenoids from the Herbs of Salicornia bigelovii

    Directory of Open Access Journals (Sweden)

    Yu Shan

    2015-11-01

    Full Text Available A new nortriterpene saponin, 3-O-β-d-glucuronopyranosyl-30-norolean-12,20(29-dien-23- oxo-28-oic acid, namely bigelovii D (11, was isolated from the hydroalcoholic extract of herbs of Salicornia bigelovii along with 10 known saponins (1–10. Their chemical structures were identified on the basis of spectroscopic analyses including two-dimensional NMR and a comparison with literature data. Some of these compounds showed potent antifungal activities in vitro. Compounds 3, 4, 5, 6, 7, 10 and 11 demonstrated potent inhibitory activities against Colletotrichum gloeosporioides and compound 11 displayed broad-spectrum inhibitory activity against Alternaria alternata, A. solani, Botrytis cinerea, C. gloeosporioides, Fusarium graminearum, F. verticilloides, Thanatephorus cucumeris and Sclerotinia sclerotiorum, with EC50 values ranging from 13.6 to 36.3 μg/mL.

  18. Inhibitory activities of 3-O-β-chacotriosyl pentacyclic triterpenoids against the entry of H5 N1 influenza viruses in vitro%马铃薯三糖五环三萜类化合物体外抗H5N1流感病毒的活性评价

    Institute of Scientific and Technical Information of China (English)

    宋高鹏; 申新田; 李素梅; 黎奕斌; 范继鸿; 梁倩倩; 刘叔文

    2015-01-01

    Aim To study the inhibitory activities of potential new anti-influenza virus agents,3-O-β-chaco-triosyl pentacyclic triterpenoids against the entry of H5N1influenza viruses.Methods Three target com-pounds were designed and synthesized structurally re-lated to the lead compound 3-O-β-chacotriosyl dioscin derivative (1 )with inhibitory activities against H5N1 influenza viruses.The inhibitory activities of these tar-get compounds were tested at a cellular level pseudo vi-rus system targeting H5N1 influenza viruse entry.Re-sults All the compounds 1 a,1 b and 1 c showed po-tent inhibitory activities against the entry of A/Thai-land/Kan353/2004 pseudo virus into the target cells, of which compound 1 b showed the best inhibitory activ-ity with an IC50 value of (1.25 ±0.22)μmol·L-1. Conclusion The SARs analysis of these compounds indicated that replacement of the aglycone moiety of compound 1 with pentacyclic triterpenoids could in-crease antiviral activity.Different types of pentacyclic triterpen as aglycone residue had the significant influ-ence on the inhibitory activity (1 b >1 c >1 a),sug-gesting ursane type of triterpenes was superior to the two other kinds of triterpenes as aglycone residue.%目的:研究3种不同类型的马铃薯三糖五环三萜能否通过抑制H5 N 1流感病毒进入靶细胞,作为潜在的新型抗流感药物进行研发。方法以马铃薯三糖薯蓣皂苷衍生物1为先导化合物,设计并合成3个目标化合物,利用建立的H5 N 1假病毒活性检测方法,测试化合物的抑制活性。结果目标化合物1 a、1 b和1 c对源自A/Thailand/Kan353/2004的H5N1假病毒毒株均具有明显的抑制作用,且化合物1b的活性最好,其IC50达到(1.25±0.22)μmol·L-1。结论初步构效关系研究表明,将先导化合物1结构中的薯蓣皂苷苷元替换成五环三萜苷元后可提高其抗病毒活性;五环三萜的苷元类型对抗病毒活性有重要影响,乌苏烷型

  19. 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.

  20. Triterpenes as α-glucosidase inhibitors from Fagus hayatae.

    Science.gov (United States)

    Lai, Yi-Chun; Chen, Chien-Kuang; Tsai, Sheng-Fa; Lee, Shoei-Sheng

    2012-02-01

    Triterpenoids, 1-3, 8 and 9, along with 24 known compounds were isolated from leaves and twigs of Fagus hayatae. Of these, compound 1, 1,10-seco-3β,10α,23-trihydroxyolean-12-ene-1,28-dioic acid 1,23-lactone, possesses a hitherto unknown 1,10-seco-oleanane skeleton. In addition, 2,3-seco-20(29)-lupene-2,3-dioic acid (16), previously described as a synthetic product, is now established as a plant natural product; the neolignan-9'-O-rhamnoside 19 is also characterized herein. Their structures were deduced mainly by 1D and 2D NMR spectroscopic analyses. Seven of these compounds possess moderate inhibitory activity against α-glucosidase type IV (Bacillus stearothermophilus).

  1. Phytochemical analysis of Pfaffia glomerata inflorescences by LC-ESI-MS/MS.

    Science.gov (United States)

    Felipe, Daniele F; Brambilla, Lara Z S; Porto, Carla; Pilau, Eduardo J; Cortez, Diógenes A G

    2014-09-29

    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.

  2. 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.

  3. Selective solid-phase extraction of a triterpene acid from a plant extract by molecularly imprinted polymer.

    Science.gov (United States)

    Claude, Bérengère; Morin, Philippe; Lafosse, Michel; Belmont, Anne-Sophie; Haupt, Karsten

    2008-04-15

    A molecularly imprinted polymer (MIP) has been prepared by a thermal polymerisation method using methacrylic acid as functional monomer, ethylene glycol dimethacrylate as cross-linking agent, chloroform as porogenic solvent and an oleanane triterpene compound (18-beta-glycyrrhetinic acid) as imprinted molecule (template). Equilibrium ligand binding experiments were done to assess the performance of the MIP relative to non-imprinted polymer (NIP). After optimisation of SPE protocol (CHCl3 as washing solvent and MeOH as elution solvent), successful imprinting was confirmed by comparison of the recoveries between NIP (5%) and MIP (97%) cartridges. The binding capacity of the MIP for 18-beta-glycyrrhetinic acid was determined to be 0.94 mg g(-1). Four structurally related oleanane triterpenes (18-alpha-glycyrrhetinic acid, oleanolic acid, echinocystic acid, erythrodiol) were selected to assess the MIP selectivity. Experimental data illustrated the influence of functional groups on the triterpene skeleton. The MIP was applied to the solid-phase extraction of triterpenoids from a plant extract prior HPLC analysis. However, CHCl3 was replaced by ACN during the washing step in order to suppress non-specific interactions due to polar matrix components. A selective extraction of 18-beta-glycyrrhetinic acid from hydrolyzed extract of liquorice roots was achieved with a good extraction yield (98%).

  4. Control of autoimmune inflammation by celastrol, a natural triterpenoid.

    Science.gov (United States)

    Venkatesha, Shivaprasad H; Dudics, Steven; Astry, Brian; Moudgil, Kamal D

    2016-08-01

    Celastrol is a bioactive compound derived from traditional Chinese medicinal herbs of the Celastraceae family. Celastrol is known to possess anti-inflammatory and anti-oxidant activities. Our studies have highlighted the immunomodulatory attributes of celastrol in adjuvant-induced arthritis (AA), an experimental model of human rheumatoid arthritis (RA). RA is an autoimmune disease characterized by chronic inflammation of the synovial lining of the joints, leading eventually to tissue damage and deformities. Identification of the molecular targets of celastrol such as the NF-κB pathway, MAPK pathway, JAK/STAT pathway and RANKL/OPG pathway has unraveled its strategic checkpoints in controlling arthritic inflammation and tissue damage in AA. The pathological events that are targeted and rectified by celastrol include increased production of pro-inflammatory cytokines; an imbalance between pathogenic T helper 17 and regulatory T cells; enhanced production of chemokines coupled with increased migration of immune cells into the joints; and increased release of mediators of osteoclastic bone damage. Accordingly, celastrol is a promising candidate for further testing in the clinic for RA therapy. Furthermore, the results of other preclinical studies suggest that celastrol might also be beneficial for the treatment of a few other autoimmune diseases besides arthritis.

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

    African Journals Online (AJOL)

    The NCI 60 human cancer cell line panel was used to .... human lung carcinoma of an IC50 of 46.2 µM ... respectively, non-small lung cancer cell line ... Table 2: Growth percentage of compound 1-3 in the NCI in vitro 60-cell Drug Screen ...

  6. Triterpenoid saponins from the shells of Argania spinosa seeds.

    Science.gov (United States)

    Alaoui, Asma; Charrouf, Zoubida; Soufiaoui, Mohamed; Carbone, Virginia; Malorni, Antonio; Pizza, Cosimo; Piacente, Sonia

    2002-07-31

    Two new oleanene saponins were isolated from the MeOH extract of the shell of Argania spinosa. They possess protobassic acid and 16alpha-protobassic acid as aglycons. The disaccharide moiety linked to C-3 of the aglycon is made up of two glucose units; the pentasaccharide moiety linked to C-28 is made up of arabinose, xylose, and three rhamnose units. Their structures were elucidated by 1D and 2D NMR experiments including (1)H-(1)H (DQF-COSY, 1D TOCSY, and 2D HOHAHA) and (1)H-(13)C (HSQC and HMBC) spectroscopy along with mass spectrometry.

  7. Triterpenoids from Argania spinosa: 20 years of research.

    Science.gov (United States)

    Chafchaouni-Moussaoui, Imane; Charrouf, Zoubida; Guillaume, Dom

    2013-01-01

    During the last two decades, the argan tree has been the subject of intensive phytochemical investigation. If argan oil is the most known argan derivative, argan saponins are frequently considered as molecules presenting a strong economic potential. This review presents an update of the current research efforts on argan saponins from around the world. Research evidence suggests that arganine C can be considered as a lead compound for new antivirals.

  8. A New Taraxastane-type Triterpenoid from Potentilla multicaulis

    Institute of Scientific and Technical Information of China (English)

    Ping Lin LI; Zhan Xin ZHANG; Zhong Jian JIA

    2006-01-01

    A new taraxastane-20β, 28β-epoxy-28-hydroxy-3β, 11α-diol- 11-p-hydroxylbenzoate was isolated from the roots of Potentilla multicaulis. Its structure was elucidated by spectroscopic methods, especially 2D NMR techniques.

  9. 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)

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

    African Journals Online (AJOL)

    IR and GC-MS. Keywords: ... recorded on a Bruker AMX-400 spectrometer and chemical shifts are ... gas chromatography that was equipped with a. 25m fused ... analytical 70-250S mass spectrometer. Thin-layer .... Thesis summary. Sule M.I. ...

  11. 乌拉尔甘草中的化学成分%Chemical constituents from root of Glycyrrhiza uralensis

    Institute of Scientific and Technical Information of China (English)

    朱绪民; 邸迎彤; 彭树林; 王明奎; 丁立生

    2003-01-01

    Object To investigate the chemical constituents from the roots of Glycyrrhiza uralensis Fisch. Methods The constituents were isolated on normal and reversed silica gel column chromatography and their structures were identified by spectral evidence. Results A new oleanane-type triterpenoid saponin and twelve known compounds, including two triterpenoid saponins, two cumarins and eight flavonoids, were isolated. Conclusion The new compound was elucidated as 3-O-[β-D-(6-methyl) glucuronopyranosyl (1→2)-D-glucuronopyranosyl]-24-hydroxy-glabrolide on the basis of ESI-MS, 1HNMR,13CNMR, HMQC and HMBC spectral evidence.%目的分析乌拉尔甘草Glycyrrhiza uralensis的化学成分.方法采用正、反相硅胶柱层析分离,应用波谱方法进行结构鉴定.结果从甘草中共分离出3个三萜皂苷、2个香豆素和8个黄酮类化合物,其中一个三萜皂苷为新化合物.结论通过ESI-MS,1HNMR,13CNMR,HMQC和HMBC分析,将新三萜皂苷的结构鉴定为3-O-[β-D-葡萄糖醛酸甲酯-(1→2)-β-D-葡萄糖醛酸]-24-羟基-甘草内酯.

  12. 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

    2015-01-01

    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.

  13. Saponins from Swartzia langsdorffii: biological activities

    Directory of Open Access Journals (Sweden)

    Magalhães Aderbal Farias

    2003-01-01

    Full Text Available The presence of saponins and the molluscicidal activity of the roots, leaves, seeds and fruits of Swartzia langsdorffii Raddi (Leguminosae against Biomphalaria glabrata adults and eggs were investigated. The roots, seeds and fruits were macerated in 95% ethanol. These extracts exerted a significant molluscicidal activity against B. glabrata, up to a dilution of 100 mg/l. Four mixtures (A2, B2, C and D of triterpenoid oleanane type saponins were chromatographically isolated from the seed and fruit extracts. Two known saponins (1 and 2 were identified as beta-D-glucopyranosyl-[alpha-L-rhamnopyranosyl-(1->3- beta-D-glucuronopyranosyl-(1->3]-3beta-hydroxyolean-12-ene-28 -oate, and beta-D-glucopyranosyl-(1->3-beta-D-glucuronopyranosyl-(1 ->3]-3beta-hydroxyolean-12-ene-28-oate, respectively. These two saponins were present in all the mixtures, together with other triterpenoid oleane type saponins, which were shown to be less polar, by reversed-phase HPLC. The saponin identifications were based on spectral evidence, including ¹H-¹H two-dimensional correlation spectroscopy, nuclear Overhauser and exchange spectroscopy, heteronuclear multiple quantum coherence, and heteronuclear multiple-bond connectivity experiments. The toxicity of S. langsdorffii saponins to non-target organisms was prescreened by the brine shrimp lethality test.

  14. Diagenesis of higher plant triterpenes in evaporitic sediments

    Science.gov (United States)

    Poinsot, J.; Adam, P.; Trendel, J. M.; Connan, J.; Albrecht, P.

    1995-11-01

    Several samples from a Tertiary carbonated evaporitic series (Sainte-Cécile, Camargue, France) were investigated. Their analysis revealed a high abundance of new or uncommon hydrocarbons and organic S compounds related to higher plant triterpenes. Several of them, in particular, 12,29-cyclolupa-12,18,20(29)-triene 1, could be positively identified. These triterpenoids are generally absent from non-evaporitic sediments which contain essentially aromatic triterpenoids resulting from microbially mediated aromatization processes starting in ring A (or in ring B when preceded by the loss of ring A). The uncommon transformations undergone by higher plant triterpenes in the highly anoxic sediments from Sainte-Cécile are specific for each series of triterpenes (i.e., oleanane, ursane, lupane) and are probably linked with the rapid disappearance of the functionality located in ring A by reduction or by the incorporation of the triterpenes in S-rich macromolecules by reaction with inorganic S species. These biological markers represent new source parameters which may be quite useful as indicators of terrestrial inputs in evaporitic deposits.

  15. Paleoclimate influence on early diagenesis of plant triterpenes in the Dajiuhu peatland, central China

    Science.gov (United States)

    Huang, Xianyu; Xue, Jiantao; Wang, Xinxin; Meyers, Philip A.; Huang, Junhua; Xie, Shucheng

    2013-12-01

    Aromatic derivatives of vascular plant triterpenoids are common in recent and ancient sediments, coal, and petroleum. Understanding their early diagenetic alterations and their relation with environmental conditions can facilitate their applications in paleoenvironmental reconstructions. Here we present a high-resolution record of aromatic triterpenes in a Holocene peat core collected in the Dajiuhu peatland, central China. These aromatic triterpenes are derivatives of plant triterpenoids with oleanane, ursane and lupane carbon skeletons and exist in three different structural groups: aromatic des-A-triterpenes, aromatic pentacyclic triterpenes, and C-ring cleaved aromatic triterpenes. Such a high diversity of aromatic triterpenes in a young peat deposit is compelling evidence for rapid microbial mediation of these important degradation pathways during very early diagenesis. Of particular importance is the occurrence of C-ring cleaved aromatic triterpene and aromatic des-A-triterpenes in the Dajiuhu peat samples, which until now have not been identified in recent sediments. The downcore profile shows that the microbial aromatization process of oleanoids positively correlates with paleoclimate change. During dry or warm intervals, highly aromatized products such as tetraaromatic triterpenes become predominant over their triaromatic homologs. In contrast, triaromatic triterpenes become dominant during wet or cold intervals. In addition, this study provides further evidence to support that the climate pattern in the middle reaches of the Yangtze River is different from that in north China during 13-9.4 ka. These findings suggest that aromatic triterpenes can be valuable tools for Holocene paleoenvironmental reconstructions.

  16. 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

    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. 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. 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. 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.

  17. 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.

  18. Biomarkers in a peat deposit in Northern Spain (Huelga de Bayas, Asturias) as proxy for climate variation.

    Science.gov (United States)

    López-Días, V; Borrego, A G; Blanco, C G; Arboleya, M; López-Sáez, J A; López-Merino, L

    2010-05-21

    Peatlands are peculiar ecosystems in which well-adapted communities grow and develop, recording the variation in climate and hydrological conditions inland. In addition necromass is well preserved and therefore peatlands can be used as palaeo-archives for environmental variation. In this work a peat core of depth 60 cm dated at the bottom of the peat deposit as ca. 250cal AD from Huelga de Bayas (Asturias, Northern Spain) was studied to a resolution of 2-4 cm to investigate the evolution of the environmental conditions in the area. Samples were extracted with a dichloromethane/methanol ratio of 3:1 and studied by means of gas chromatography (GC) and mass spectrometry (GC-MS) in order to identify possible biomarkers of climatic variation during the period of peat formation. Lipid biomarker study allows the identification of periods in which Sphagnum or higher plants preferentially contributed to the peat profile. The absolute dating of the profile combined with the n-alkane record displayed five episodes of wetter conditions around ca. 250 cal AD (Roman Warm Period), 1080 and 1270 cal AD (Medieval Warm Period), 1460 cal AD (Little Ice Age) and 1920 cal AD (Recent warming), which are consistent with climate evolution in the region. Pentacyclic triterpenoids with hopane skeleton derived from microorganisms and with oleanane skeleton derived from higher plants were identified. The presence of their ketone and acetyl-derivatives, along with the presence of unstable hopane configurations indicates a low maturity of the peat profile. A tendency for the functionalised triterpenoids to decrease with depth was observed in the profile.

  19. Fragment ion diagnostic strategies for the comprehensive identification of chemical profile of Gui-Zhi-Tang by integrating high-resolution MS, multiple-stage MS and UV information.

    Science.gov (United States)

    Wang, Shufang; Chen, Lulin; Leng, Jing; Chen, Pinghong; Fan, Xiaohui; Cheng, Yiyu

    2014-09-01

    Gui-Zhi-Tang was considered to be the most famous formula in Shang-Han-Lun, treating 32 symptoms of disease after adding up or cutting down crude drugs. The chemical constituents in Gui-Zhi-Tang were comprehensively studied by rapid resolution liquid chromatography quadrupole time-of-flight mass spectrometry (RRLC-Q-TOF-MS) combined with rapid resolution liquid chromatography - diode array detector - ion trap mass spectrometry (RRLC-DAD-IT-MS) in this work, and a total number of 187 compounds were detected. Systematic diagnostic ion filtering strategies were recommended for flavonoids and oleanane-type triterpenoids, respectively. On the basis of the summarized strategies, compounds in Glycyrrhizae could be easily classified into flavones, isoflavones, flavanones or chalcones with special structures, and triterpene saponins with different sugar moieties. Consequently, among 187 compounds, 144 ones were confirmed or assumed tentatively. In addition, nine potential novel compounds were reported for the first time. This approach provided a rapid method for characterizing the constituents in Gui-Zhi-Tang, and would be also helpful in other TCM formulae analysis.

  20. 柴胡皂苷类药效分子机制研究最新进展%The latest progress on the molecular mechanisms of pharmacological activity of saikosaponins

    Institute of Scientific and Technical Information of China (English)

    程玉鹏; 马爱萍; 陈琦; 林进华; 李天聪; 李弘琨

    2016-01-01

    柴胡皂苷为齐墩果烷型三萜皂苷,是传统中药柴胡的主要化学和生物活性成分,具有解热、镇静、止痛、镇咳等作用。近期,柴胡皂苷药效分子机制的新研究成果不断涌现,所以总结了现代药理药效学关于柴胡皂苷在逆转多药耐药、防治肝病和保护肝脏、抗炎、抗肿瘤方面的分子机制研究最新进展情况,为其在临床的进一步应用提供参考。%The main bioactive chemical ingredients of traditional Chinese medicine Bupleurum are saikos-aponins, oleanane-type triterpenoid saponins, which are applied in the functions of antipyretic, sepative, analgesic, antibechic. The molecular mechanisms of pharmacological activity of saikosaponins have constantly been revealed. This article reviews recent advances in the effects of saikosaponins on reversing multiple drug resistance (MDR), hepatopretection, anti-inflammatory and anti-tumor. It will provide reference for further application of saikos-aponins in clinical practice.

  1. Oleanonic acid, a 3-oxotriterpene from Pistacia, inhibits leukotriene synthesis and has anti-inflammatory activity.

    Science.gov (United States)

    Giner-Larza, E M; Máñez, S; Recio, M C; Giner, R M; Prieto, J M; Cerdá-Nicolás, M; Ríos, J L

    2001-09-28

    One of the best known bioactive triterpenoids is oleanolic acid, a widespread 3-hydroxy-17-carboxy oleanane-type compound. In order to determine whether further oxidation of carbon 3 affects anti-inflammatory activity in mice, different tests were carried out on oleanolic acid and its 3-oxo-analogue oleanonic acid, which was obtained from Pistacia terebinthus galls. The last one showed activity on the ear oedema induced by 12-deoxyphorbol-13-phenylacetate (DPP), the dermatitis induced by multiple applications of 12-O-tetradecanoyl-13-acetate (TPA) and the paw oedemas induced by bradykinin and phospholipase A2. The production of leukotriene B4 from rat peritoneal leukocytes was reduced by oleanonic acid with an IC50 of 17 microM. Negligible differences were observed in the response of both triterpenes to DPP, bradykinin, and phospholipase A2, while oleanonic acid was more active on the dermatitis by TPA and on the in vitro leukotriene formation. In conclusion, the presence of a ketone at C-3 implies an increase in the inhibitory effects on models related to 5-lipoxygenase activity and on associated in vivo inflammatory processes.

  2. 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.

  3. New Enzyme-Inhibitory Triterpenoid from Marine Macro Brown Alga Padina boergesenii Allender & Kraft

    Science.gov (United States)

    Ali, Liaqat; Khan, Abdul Latif; Al-Broumi, Muhammad; Al-Harrasi, Rashid; Al-Kharusi, Lubna; Hussain, Javid; Al-Harrasi, Ahmed

    2017-01-01

    In continuation to our study of the chemical and biological potential of the secondary metabolites isolated from Omani seaweeds, we investigated a marine brown alga, Padina boergesenii. The phytochemical investigation resulted in the isolation of a new secondary metabolite, padinolic acid (1), along with some other semi-pure fractions and sub-fractions. The planar structure was confirmed through MS and NMR (1D and 2D) spectral data. The NOESY experiments coupled with the biogenetic consideration were helpful in assigning the stereochemistry in the molecule. Compound 1 was subjected to enzyme inhibition studies using urease, lipid peroxidase, and alpha-glucosidase enzymes. Compound 1 showed low to moderate α-glucosidase and urease enzyme inhibition, respectively, and moderate anti-lipid peroxidation activities. The current study indicates the potential of this seaweed and provides the basis for further investigation. PMID:28106757

  4. A Comprehensive Review of the Structure Elucidation and Biological Activity of Triterpenoids from Ganoderma spp.

    Directory of Open Access Journals (Sweden)

    Qing Xia

    2014-10-01

    Full Text Available Ganoderma triterpenes (GTs are the major secondary metabolites of Ganoderma lucidum, a traditional Chinese medicine, popularly used for complementary cancer therapy. GTs are lanostane-tetracyclic triterpenes. They have been reported to possess anti-tumor, anti-inflammation, antioxidant, antimicrobial and blood fat reducing effects. To date, 316 GTs have been found and their similar chemical structures have proved difficult to elucidate. This paper compiles 316 naturally occurring triterpenes from Ganoderma based on the literature published through January 2013 along with their structures, physiological activities and 13C-NMR spectral data.

  5. A comprehensive review of the structure elucidation and biological activity of triterpenoids from Ganoderma spp.

    Science.gov (United States)

    Xia, Qing; Zhang, Huazheng; Sun, Xuefei; Zhao, Haijuan; Wu, Lingfang; Zhu, Dan; Yang, Guanghui; Shao, Yanyan; Zhang, Xiaoxue; Mao, Xin; Zhang, Lanzhen; She, Gaimei

    2014-10-30

    Ganoderma triterpenes (GTs) are the major secondary metabolites of Ganoderma lucidum, a traditional Chinese medicine, popularly used for complementary cancer therapy. GTs are lanostane-tetracyclic triterpenes. They have been reported to possess anti-tumor, anti-inflammation, antioxidant, antimicrobial and blood fat reducing effects. To date, 316 GTs have been found and their similar chemical structures have proved difficult to elucidate. This paper compiles 316 naturally occurring triterpenes from Ganoderma based on the literature published through January 2013 along with their structures, physiological activities and 13C-NMR spectral data.

  6. Triterpenoid-Rich Extract from Antrodia camphorata Improves Physical Fatigue and Exercise Performance in Mice

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    Chi-Chang Huang

    2012-01-01

    Full Text Available Antrodia camphorata (AC is an endemic mushroom that grows in Taiwan. We investigated the fatigue-alleviating effects of AC on endurance capacity in swim-exercised and weight-loading mice. Male Institute of Cancer Research (ICR strain mice from 3 groups (n=10 per group in each test were orally administered AC fruiting body extract for 7 days at 0, 50, and 200 mg/kg/day, designated vehicle, AC-50, and AC-200, respectively. Trend analysis revealed that AC treatments increased grip strength. AC dose-dependently increased swim time, blood glucose, and muscular and hepatic glycogen levels and dose-dependently decreased plasma lactate and ammonia levels and creatine kinase activity. The increase in swimming endurance with AC administration was caused by an increase in liver and muscle glycogen deposition. A. camphorata may have potential for use in ergogenic and antifatigue activities.

  7. New cyclopropyl-triterpenoids from the aerial roots of Ficus microcarpa.

    Science.gov (United States)

    Chiang, Y M; Su, J K; Liu, Y H; Kuo, Y H

    2001-05-01

    Four new cyclopropyl-triterpenes, 27-nor-3beta-hydroxy-25-oxocycloartane (1), (22E)-25,26,27-trinor-3beta-hydroxycycloart-22-en-24-al (2), 3beta-acetoxy-15alpha-hydroxy-13,27-cyclours-11-ene (3), 3beta-acetoxy-12alpha-formyloxy-13,27-cycloursan-11alpha-ol (4), together with (23E)-27-nor-3beta-hydroxycycloart-23-en-25-one (5) were isolated from the aerial roots of Ficus microcarpa. Compounds 3 and 4 are rare 13,27-cycloursane-type triterpenes. Their structures were elucidated by spectroscopic and chemical methods.

  8. 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...

  9. 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”.

  10. New Enzyme-Inhibitory Triterpenoid from Marine Macro Brown Alga Padina boergesenii Allender & Kraft.

    Science.gov (United States)

    Ali, Liaqat; Khan, Abdul Latif; Al-Broumi, Muhammad; Al-Harrasi, Rashid; Al-Kharusi, Lubna; Hussain, Javid; Al-Harrasi, Ahmed

    2017-01-18

    In continuation to our study of the chemical and biological potential of the secondary metabolites isolated from Omani seaweeds, we investigated a marine brown alga, Padina boergesenii. The phytochemical investigation resulted in the isolation of a new secondary metabolite, padinolic acid (1), along with some other semi-pure fractions and sub-fractions. The planar structure was confirmed through MS and NMR (1D and 2D) spectral data. The NOESY experiments coupled with the biogenetic consideration were helpful in assigning the stereochemistry in the molecule. Compound 1 was subjected to enzyme inhibition studies using urease, lipid peroxidase, and alpha-glucosidase enzymes. Compound 1 showed low to moderate α-glucosidase and urease enzyme inhibition, respectively, and moderate anti-lipid peroxidation activities. The current study indicates the potential of this seaweed and provides the basis for further investigation.

  11. 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.

  12. 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.

  13. Ursolic acid from apple pomace and traditional plants: A valuable triterpenoid with functional properties.

    Science.gov (United States)

    Cargnin, Simone Tasca; Gnoatto, Simone Baggio

    2017-04-01

    Apple juice production generates a large amount of residue comprising mainly peels, seeds, and pulp, known as apple pomace. In the global context, Brazil ranks 11th in apple production and thousands of tons of apple pomace are produced every year. This by-product is little explored, since it is a rich and heterogeneous mixture, containing interesting phytochemical groups. Among them, ursolic acid (UA) has attracted attention because of its therapeutic potential. UA is a pentacyclic triterpene found too in several traditional plants, and has shown several functional properties such as antibacterial, antiprotozoal, anti-inflammatory and antitumor. Therefore, this review attempts to shed some light on the economical viability of apple and apple pomace as sources of bioactive compounds, highlighting the UA extraction, and its main functional properties published in the last 5years (2010-2015).

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

    DEFF Research Database (Denmark)

    Erthmann, Pernille Østerbye

    are identified and found to be responsible for resistance towards flea beetles (Phyllotreta nemorum) and diamondback moths (Plutella xylostella). Genes involved in the biosynthesis of these saponins were recently identified, however the complete biosynthetic pathway is not known to date. These findings set...

  15. α,β-amyrin, a natural triterpenoid ameliorates L-arginine-induced acute pancreatitis in rats

    Institute of Scientific and Technical Information of China (English)

    Caroline; Mouro; Melo; Karine; Maria; Martins; Bezerra; Carvalho; Julliana; Catharina; de; Sousa; Neves; Talita; Cavalcante; Morais; Vietla; Satyanarayana; Rao; Flávia; Almeida; Santos; Gerly; Anne; de; Castro; Brito; Mariana; Helena; Chaves

    2010-01-01

    AIM: To study the benef icial effects of triterpene α,β-amyrin and the underlying mechanisms in an experimental pancreatitis model. METHODS: Acute pancreatitis was induced in five groups of rats (n = 8) by L-arginine (2 × 2.5 g/kg, intraperitoneal, 1 h apart) and 1 h later, they received a single oral dose of α,β-amyrin (10, 30 and 100 mg/kg),methylprednisolone (30 mg/kg) and vehicle (3% Tween 80). A saline (0.9% NaCl) treated group served as a normal control. Efficacy was assessed at 24 h by determination ...

  16. Constituents of catha edulis (alkaloids, triterpenoids and related substances and saponins)

    OpenAIRE

    Rizk, A.M.; Mobarak, Z. M.; El-Shihi, T.

    1989-01-01

    The study of the alkaloids of khat samples from Egypt and Yemen revealed qualitative and quantitative differences. Cathine and the dimer of cathinone occured in both samples, while norephedine was detected only in Yemen samples. Investigation of certain other constituents viz. triterpenes, sterols, fatty alcohols, hydrocarbons, fatty acids and saponins resulted in the isolation and identification of several components أسفرت دراسة القلويدات فتي عينتين من القات المنزرع في مصر واليمن عن وجود ...

  17. First ever isolation of cytotoxic triterpenoid 2-hydroxydiplopterol from plant source

    Science.gov (United States)

    Arisaema jacquemontii have shown medicinal importance and biological activities particularly, its anticancer activity, so we have decided to keep on investigating the plant in term of its chemical constituents. A chemical investigation on the chloroform extract of A. jacquemontii have resulted in th...

  18. Structure of the BTB domain of Keap1 and its interaction with the triterpenoid antagonist CDDO.

    Directory of Open Access Journals (Sweden)

    Anne Cleasby

    Full Text Available The protein Keap1 is central to the regulation of the Nrf2-mediated cytoprotective response, and is increasingly recognized as an important target for therapeutic intervention in a range of diseases involving excessive oxidative stress and inflammation. The BTB domain of Keap1 plays key roles in sensing environmental electrophiles and in mediating interactions with the Cul3/Rbx1 E3 ubiquitin ligase system, and is believed to be the target for several small molecule covalent activators of the Nrf2 pathway. However, despite structural information being available for several BTB domains from related proteins, there have been no reported crystal structures of Keap1 BTB, and this has precluded a detailed understanding of its mechanism of action and interaction with antagonists. We report here the first structure of the BTB domain of Keap1, which is thought to contain the key cysteine residue responsible for interaction with electrophiles, as well as structures of the covalent complex with the antagonist CDDO/bardoxolone, and of the constitutively inactive C151W BTB mutant. In addition to providing the first structural confirmation of antagonist binding to Keap1 BTB, we also present biochemical evidence that adduction of Cys 151 by CDDO is capable of inhibiting the binding of Cul3 to Keap1, and discuss how this class of compound might exert Nrf2 activation through disruption of the BTB-Cul3 interface.

  19. 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 (Cmax and AUC0-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.

  20. New Enzyme-Inhibitory Triterpenoid from Marine Macro Brown Alga Padina boergesenii Allender & Kraft

    Directory of Open Access Journals (Sweden)

    Liaqat Ali

    2017-01-01

    Full Text Available In continuation to our study of the chemical and biological potential of the secondary metabolites isolated from Omani seaweeds, we investigated a marine brown alga, Padina boergesenii. The phytochemical investigation resulted in the isolation of a new secondary metabolite, padinolic acid (1, along with some other semi-pure fractions and sub-fractions. The planar structure was confirmed through MS and NMR (1D and 2D spectral data. The NOESY experiments coupled with the biogenetic consideration were helpful in assigning the stereochemistry in the molecule. Compound 1 was subjected to enzyme inhibition studies using urease, lipid peroxidase, and alpha-glucosidase enzymes. Compound 1 showed low to moderate α-glucosidase and urease enzyme inhibition, respectively, and moderate anti-lipid peroxidation activities. The current study indicates the potential of this seaweed and provides the basis for further investigation.

  1. The Sg-1 glycosyltransferase locus regulates structural diversity of triterpenoid saponins of soybean.

    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

    2012-05-01

    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-1(a) allele encodes the xylosyltransferase UGT73F4, whereas Sg-1(b) encodes the glucosyltransferase UGT73F2. Homology models and site-directed mutagenesis analyses showed that Ser-138 in Sg-1(a) and Gly-138 in Sg-1(b) proteins are crucial residues for their respective sugar donor specificities. Transgenic complementation tests followed by recombinant enzyme assays in vitro demonstrated that sg-1(0) 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.

  2. 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

  3. Isolation of two triterpenoids and a biflavanone with anti-Inflammatory activity from Schinus molle fruits.

    Science.gov (United States)

    Yueqin, Zeng; Recio, M Carmen; Máñez, Salvador; Giner, Rosa M; Cerdá-Nicolás, M; Ríos, José-Luis

    2003-10-01

    Three compounds with anti-inflammatory activity were isolated from Schinus molle fruits. Two of the compounds were identified as 3- epi-isomasticadienolalic acid ( 1), isomasticadienonalic acid ( 2) and chamaejasmin ( 3). Triterpenes 1 and 2, and biflavanone 3 were tested on two models of mice paw inflammation: one of acute inflammation, induced by subcutaneous injection of either phospholipase A (2) (PLA (2)) or carrageenan in the paws of mice, and one of chronic inflammation in the form of eczema, provoked by repeated administration of TPA to the ears of mice. On the PLA (2)-induced mouse paw oedema, only 2 was active (30 mg/kg, 66 % inhibition at 60 min), whereas all compounds reduced the chronic model of inflammation (48 to 26 % of swelling reduction), but only triterpenes reduced the leukocyte infiltration, measured as tissue peroxidase activity. In the case of the carrageenan-induced mouse paw oedema, only 3 led to a reduction of the swelling 3 h after challenge (50 mg/kg, 46 % oedema inhibition). In addition, 3 inhibited the LTB (4) production in rat peritoneal polymorphonuclear leukocytes with an IC (50) value of 29.8 microM, while triterpenes showed toxicity against cells at 100 microM.

  4. 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.

  5. Triterpenoids with acetylcholinesterase inhibition from Chuquiraga erinacea D. Don. subsp. erinacea (Asteraceae).

    Science.gov (United States)

    Gurovic, María Soledad; Castro, María Julia; Richmond, Victoria; Faraoni, María Belén; Maier, Marta S; Murray, Ana Paula

    2010-04-01

    A bioactivity-guided approach was taken to identify the acetylcholinesterase (AChE) inhibitory agents in the ethanolic extract of Chuquiraga erinacea D. Don. subsp. erinacea leaves using a bioautographic method. This permitted the isolation of the pentacyclic triterpenes calenduladiol (1), faradiol (2), heliantriol B2 (3), lupeol (4), and a mixture of alpha-and beta-amyrin ( 5A and 5B) as active constituents. Pseudotaraxasterol (6) and taraxasterol (7) were also isolated from this extract and showed no activity at the same analytical conditions. Compound 1 showed the highest AChE inhibitory activity with 31.2 % of inhibition at 0.5 mM. Looking forward to improve the water solubility of the active compounds, the sodium sulfate ester of 1 was prepared by reaction with the (CH3)3N.SO3 complex. The semisynthetic derivative disodium calenduladiol disulfate (8) elicited higher AChE inhibition than 1 with 94.1 % of inhibition at 0.5 mM (IC (50) = 0.190 +/- 0.003 mM). Compounds 1, 2, 3, 5, 6, and 7 are reported here for the first time in C. erinacea. This is the first report of AChE inhibition from calenduladiol (1) as well as from a sulfate derived from a natural product.

  6. The anticancer plant triterpenoid, avicin D, regulates glucocorticoid receptor signaling: implications for cellular metabolism.

    Directory of Open Access Journals (Sweden)

    Valsala Haridas

    Full Text Available Avicins, a family of apoptotic triterpene electrophiles, are known to regulate cellular metabolism and energy homeostasis, by targeting the mitochondria. Having evolved from "ancient hopanoids," avicins bear a structural resemblance with glucocorticoids (GCs, which are the endogenous regulators of metabolism and energy balance. These structural and functional similarities prompted us to compare the mode of action of avicin D with dexamethasone (Dex, a prototypical GC. Using cold competition assay, we show that Avicin D competes with Dex for binding to the GC receptor (GR, leading to its nuclear translocation. In contrast to Dex, avicin-induced nuclear translocation of GR does not result in transcriptional activation of GC-dependent genes. Instead we observe a decrease in the expression of GC-dependent metabolic proteins such as PEPCK and FASN. However, like Dex, avicin D treatment does induce a transrepressive effect on the pro-inflammatory transcription factor NF-κB. While avicin's ability to inhibit NF-κB and its downstream targets appear to be GR-dependent, its pro-apoptotic effects were independent of GR expression. Using various deletion mutants of GR, we demonstrate the requirement of both the DNA and ligand binding domains of GR in mediating avicin D's transrepressive effects. Modeling of avicin-GR interaction revealed that avicin molecule binds only to the antagonist confirmation of GR. These findings suggest that avicin D has properties of being a selective GR modulator that separates transactivation from transrepression. Since the gene-activating properties of GR are mainly linked to its metabolic effects, and the negative interference with the activity of transcription factors to its anti-inflammatory and immune suppressive effects, the identification of such a dissociated GR ligand could have great potential for therapeutic use.

  7. Triterpenoid glycosides from Medicago sativa as antifungal agents against Pyricularia oryzae.

    Science.gov (United States)

    Abbruscato, Pamela; Tosi, Solveig; Crispino, Laura; Biazzi, Elisa; Menin, Barbara; Picco, Anna M; Pecetti, Luciano; Avato, Pinarosa; Tava, Aldo

    2014-11-19

    The antifungal properties of saponin mixtures from alfalfa (Medicago sativa L.) tops and roots, the corresponding mixtures of prosapogenins from tops, and purified saponins and sapogenins against the causal agent of rice blast Pyricularia oryzae isolates are presented. In vitro experiments highlighted a range of activities, depending upon the assayed metabolite. The antifungal effects of the most promising prosapogenin mixture from alfalfa tops were confirmed by means of in planta tests using three different Italian cultivars of rice (Oryza sativa L. ssp. japonica), known to possess high, medium, and low blast resistance. The evidenced antifungal properties of the tested metabolites allowed some considerations on their structure-activity relationship. Results indicate that prosapogenins are active compounds to prevent the fungal attack of P. oryzae on different rice cultivars. Therefore, if properly formulated, these substances could represent a promising and environmentally friendly treatment to control rice blast.

  8. The anticancer plant triterpenoid, avicin D, regulates glucocorticoid receptor signaling: implications for cellular metabolism.

    Science.gov (United States)

    Haridas, Valsala; Xu, Zhi-Xiang; Kitchen, Doug; Jiang, Anna; Michels, Peter; Gutterman, Jordan U

    2011-01-01

    Avicins, a family of apoptotic triterpene electrophiles, are known to regulate cellular metabolism and energy homeostasis, by targeting the mitochondria. Having evolved from "ancient hopanoids," avicins bear a structural resemblance with glucocorticoids (GCs), which are the endogenous regulators of metabolism and energy balance. These structural and functional similarities prompted us to compare the mode of action of avicin D with dexamethasone (Dex), a prototypical GC. Using cold competition assay, we show that Avicin D competes with Dex for binding to the GC receptor (GR), leading to its nuclear translocation. In contrast to Dex, avicin-induced nuclear translocation of GR does not result in transcriptional activation of GC-dependent genes. Instead we observe a decrease in the expression of GC-dependent metabolic proteins such as PEPCK and FASN. However, like Dex, avicin D treatment does induce a transrepressive effect on the pro-inflammatory transcription factor NF-κB. While avicin's ability to inhibit NF-κB and its downstream targets appear to be GR-dependent, its pro-apoptotic effects were independent of GR expression. Using various deletion mutants of GR, we demonstrate the requirement of both the DNA and ligand binding domains of GR in mediating avicin D's transrepressive effects. Modeling of avicin-GR interaction revealed that avicin molecule binds only to the antagonist confirmation of GR. These findings suggest that avicin D has properties of being a selective GR modulator that separates transactivation from transrepression. Since the gene-activating properties of GR are mainly linked to its metabolic effects, and the negative interference with the activity of transcription factors to its anti-inflammatory and immune suppressive effects, the identification of such a dissociated GR ligand could have great potential for therapeutic use.

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

    Directory of Open Access Journals (Sweden)

    Carlos Areche

    2009-01-01

    Full Text Available 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.

  10. Epoxides, cyclic sulfites, and sulfate from natural pentacyclic triterpenoids: theoretical calculations and chemical transformations.

    Science.gov (United States)

    García-Granados, Andrés; López, Pilar E; Melguizo, Enrique; Moliz, Juan N; Parra, Andrés; Simeó, Yolanda; Dobado, José A

    2003-06-13

    Several triterpenic derivatives, with the A-ring functionalized, were semisynthesized from oleanolic and maslinic acids. The reactivities of sulfites, sulfate, and epoxides in these triterpene compounds were investigated under different reaction conditions. Moreover, contracted A-ring triterpenes (five-membered rings) were obtained, by different treatments of the sulfate 7. From the epoxide 8, deoxygenated and halohydrin derivatives were semisynthesized with several nucleophiles. Ozonolysis and Beckmann reactions were used to yield 4-aza compounds, from five-membered ring olanediene triterpenes. The X-ray structure of sulfate 7 is given and compared with density functional theory geometries. Theoretical (13)C and (1)H chemical shifts (gauge-invariant atomic orbital method at the B3LYP/6-31G*//B3LYP/6-31G* level) and (3)J(H,H) coupling constants were calculated for compounds 5-9 and 34-36, identifying the (R)- or (S)-sulfur and alpha- or beta-epoxide configurations together with 4-aza or 3-aza structures.

  11. 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.

  12. Neuroprotective effect of a triterpenoid saponin isolated from Momordica cymbalaria Fenzl in diabetic peripheral neuropathy.

    Science.gov (United States)

    Koneri, Raju B; Samaddar, Suman; Simi, S M; Rao, Srinivas T

    2014-01-01

    To investigate the neuroprotective potential of a saponin isolated from the roots of Momordica cymbalaria against peripheral neuropathy in streptozotocin-induced diabetic rats. A steroidal saponin (SMC) was isolated from M. cymbalaria Fenzl and purified by preparative high-performance liquid chromatography. Diabetes was induced in male Wister rats by injecting streptozotocin 45 mg/kg. Diabetic rats were divided into six groups for neuroprotective effect--three each for preventive and curative groups. Neuropathic analgesia was assessed by tail-flick and hot-plate methods. Dorsal root ganglion (DRG) neurons and sciatic nerves were isolated, and histopathological analysis was performed. Antioxidant activity (superoxide dismutase, catalase, and inhibition of lipid peroxidation) of the saponin was also carried out on the isolated DRG neurons and sciatic nerves to assess total oxidative stress. In both preventive and curative protocols, rats administered with SMC showed significant decrease in tail immersion latency time and increase in pain sensitivity when compared to diabetic control group. There was improvement in the myelination and degenerative changes of the nerve fiber in both the groups, and an obvious delay in the progression of neuropathy was evident. SMC treatment showed significant decrease in superoxide dismutase, catalase activity, and lipid peroxidation in the nerves. The steroidal saponin of M. cymbalaria (SMC) possesses potential neuroprotective effect in diabetic peripheral neuropathy with respect to neuropathic analgesia, improvement in neuronal degenerative changes, and significant antioxidant activity.

  13. 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)

  14. A new friedelane triterpenoid and saponin with moderate antimicrobial activity from the stems of Drypetes laciniata

    Institute of Scientific and Technical Information of China (English)

    Simone Veronique Fannang; Victor Kuete; Celine Mbazoa Djama; Marlise Diane J. Dongfack; Jean Duplex Wansi; Francois Tillequin; Elisabeth Seguin; Elizabeth Chosson; Jean Wandji

    2011-01-01

    A new friedelane-type triterpene named 3β-hydroxyfriedelane-7,12,22-trione, as well as nine known compounds were isolated from the whole stems of Drypetes laciniata Hutch. (Euphorbiaceae). Their structures were established on the basis of spectroscopic methods. The new triterpene derivative and a known saponin were tested for antimicrobial and antifungal activities and they appeared to be moderate active.

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

    African Journals Online (AJOL)

    GREGORY

    2010-09-20

    Sep 20, 2010 ... pubescens P. F. Li or Phyllostachys nigra (Lodd.) Munro .... The ion source temperature was 230°C. Full scan mode was used with the MS scan ... evaluated the growth inhibitory effect of the adherent tumor cells. (P388 mouse ...

  16. The structures of four triterpenoid saponins isolated from the seed of Trifolium incarnatum

    Directory of Open Access Journals (Sweden)

    Marian Jurzysta

    2014-02-01

    Full Text Available A novel bisdesmosidic saponin, 3-0-[α-L-rhamnopyranosyl(1 - 2-β-D-galactopyranosyl (1-2-β-D-glucuronopyranosyl]-22-O-[β-D-glucopyranosyl(1-2-β-D-glucopyranosyl] ole­an-l2-ene-24-ol has been isolated from the seed of the clover, Trifolium incarnatum. The structure of this and of three other structurally related saponins, 3-0-(β-D-glucuronopyra-nosylolean-l2-ene-22, 24-diol, soyasaponin I and soyasaponin III have been assigned on the basis of spectral and chemical evidence.

  17. D:C-friedooleanane-type triterpenoids from Lagenaria siceraria and their cytotoxic activity.

    Science.gov (United States)

    Chen, Chiy-Rong; Chen, Hung-Wei; Chang, Chi-I

    2008-03-01

    Four new D:C-friedooleanane-type triterpenes, 3 beta-O-(E)-feruloyl-D:C-friedooleana-7,9(11)-dien-29-ol (1), 3 beta-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-ol (2), 3 beta-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-oic acid (3), and methyl 2 beta,3 beta-dihydroxy-D:C-friedoolean-8-en-29-oate (6), together with five known triterpenes with the same skeleton, 3-epikarounidiol (4), 3-oxo-D:C-friedoolena-7,9(11)-dien-29-oic acid (5), bryonolol (7), bryononic acid (8), and 20-epibryonolic acid (9), were isolated from the methanol extract of the stems of Lagenaria siceraria. The structures of those compounds were elucidated using spectroscopic methods. Compounds 3 and 9 showed significant cytotoxic activity against the SK-Hep 1 cell line with IC50 values of 4.8 and 2.1 microg/ml, respectively. Based on these initially promising results, the two D:C-friedooleanane triterpenes merit further study as potential anticancer agents.

  18. Isoflavone and triterpenoid isolated from an endemic plant Genista microcephala Coss et Dur.

    Directory of Open Access Journals (Sweden)

    Ilhem Bouakaz

    2015-02-01

    Full Text Available Context: Genista microcephala Coss et Dur is a plant that grows in northern of Algeria. The Genista species show interesting biological properties. Aims: To study phytochemically of the aerial parts of G. microcephala and search new compounds with pharmacological interest. Methods: Aerial parts of G. microcephala were extracted using chloroform. The extract was purified by several chromatography processes. Isolated compounds were analyzed by the usual spectroscopic methods and 2D NMR technics. Results: From the chloroformic extract of the air parts of Genista microcephala (Leguminosae two known components were obtained. The structures of these compounds were oleanolic acid (1, alpinum isoflavone (2 elucidated by the usual spectroscopic methods and 2D NMR technics and by comparison with literature data. Conclusions: Two known components were obtained from the chloroformic extract of the air parts of Genista microcephala but they have not previously been reported from this species.

  19. Biotransformation and metabolic profile of American ginseng saponins with human intestinal microflora by liquid chromatography quadrupole time-of-flight mass spectrometry.

    Science.gov (United States)

    Wan, Jin-Yi; Liu, Peng; Wang, Huai-You; Qi, Lian-Wen; Wang, Chong-Zhi; Li, Ping; Yuan, Chun-Su

    2013-04-19

    American ginseng is a widely used natural product. Ginseng products are usually taken orally, and human intestinal microflora may metabolize ginsenosides. Existing publications report the metabolite fates of ginsenosides. However, investigations on the comprehensive metabolic profile of American ginseng extract are absent because of the chemical complexity and limitation of analytical methods. In this work, we studied the biotransformation and metabolic profile of American ginseng extract by human intestinal microflora. Human fecal microflora was prepared from a healthy Chinese man and then anaerobically incubated with American ginseng sample at 37 °C for 24 h. A rapid and simple liquid-liquid extraction method was used for sample pretreatment. A highly sensitive and selective liquid chromatography/quadrupole time-of-flight mass spectrometry (LC-Q-TOF-MS) method was used to characterize ginsenosides and related metabolites in the reaction samples. The LC-Q-TOF-MS provides superior data quality and advanced analytical capabilities for profiling, identifying, and characterizing complex metabolites in matrix-based biological samples. A total of 25 metabolites were detected, 13 of which were undoubtedly assigned by comparison with reference compounds, and 12 others were tentatively identified. The three most abundant metabolites are 20S-ginsenoside Rg3, ginsenoside F2 and compound K. The main metabolic pathways of ginseng saponins are deglycosylation reactions by intestinal microflora through stepwise cleavage of sugar moieties. Subsequent dehydration reactions also occur. Protopanaxadiol- and oleanane-type triterpenoids are easy to metabolize. The intestinal microbiota may play an important role in mediating the metabolism bioactivity of American ginseng. Copyright © 2013 Elsevier B.V. All rights reserved.

  20. The pentacyclic triterpenoid, plectranthoic acid, a novel activator of AMPK induces apoptotic death in prostate cancer cells.

    Science.gov (United States)

    Akhtar, Nosheen; Syed, Deeba N; Khan, Mohammad Imran; Adhami, Vaqar M; Mirza, Bushra; Mukhtar, Hasan

    2016-01-26

    Epidemiologic studies indicated that diabetics treated with metformin had a lower incidence of cancer than those taking other anti-diabetes drugs. This led to a surge in the efforts for identification of safer and more effective metformin mimetic compounds. The plant Ficus microcarpa is widely used for the treatment of type 2 diabetes in traditional medicine in South Asia. We obtained extracts from this plant and identified a small molecule, plectranthoic acid (PA), with potent 5'AMP-activated kinase (AMPK) activating properties far superior than metformin. AMPK is the central hub of metabolic regulation and a well-studied therapeutic target for metabolic syndrome, type-2 diabetes and cancer. We observed that treatment of prostate cancer (PCa) cells with PA inhibited proliferation and induced G0/G1 phase cell cycle arrest that was associated with up-regulation of cyclin kinase inhibitors p21/CIP1 and p27/KIP1. PA treatment suppressed mTOR/S6K signaling and induced apoptosis in PCa cells in an AMPK-dependent manner. Interestingly, PA-induced autophagy in PCa cells was found to be independent of AMPK activation. Combination studies of PA and metformin demonstrated that metformin had an inhibitory effect on PA-induced AMPK activation and suppressed PA-mediated apoptosis. Given the anti-proliferative role of PA in cancer and its potent anti-hyperglycemic activity, we suggest that PA should be explored further as a novel activator of AMPK for its ultimate use for the prevention of cancers and treatment of type 2 diabetes.

  1. Determinación de ácidos grasos y compuestos triterpenoides del cuerpo fructifero de suillus luteus.

    OpenAIRE

    Ivonne Nieto; Iris Avila

    2009-01-01

    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, ...

  2. Cimicifoetisides A and B, two cytotoxic cycloartane triterpenoid glycosides from the rhizomes of Cimicifuga foetida, inhibit proliferation of cancer cells

    Directory of Open Access Journals (Sweden)

    Qiu Ming-Hua

    2007-01-01

    Full Text Available Abstract Two new cycloartane-type triterpene glycosides, namely cimicifoetisides A (1 and B (2, along with seven known compounds cimigenol, 25-O-acetylcimigenol, cimigenol 3-O-β-D-xylopyranoside, 12β-hydroxycimigenol 3-O-β-D-xylopyranoside, cimigenol 3-O-α-L-arabinopyranoside, 25-deoxyshengmanol 3-O-β-D-xylopyranoside and cimilactone A, were isolated from the rhizomes of Cimicifuga foetida. Their structures were elucidated as cimigenol 3-O-(2'-O-acetyl-α-L-arabinopyranoside (1 and 25-O-acetylcimigenol 3-O-(2'-O-acetyl-α-L-arabinopyranoside (2. Both compounds 1 and 2 exhibited potent cytotoxicity against rat EAC (Ehrlich ascites carcinoma and MDA-MB-A231 (human breast cancer cells with IC50 values of 0.52 and 6.74 μM for 1, and 0.19 and 10.21 μM for 2, suggesting their potential for further investigation as anti-cancer agents.

  3. 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.

  4. Hawthorn ethanolic extracts with triterpenoids and flavonoids exert hepatoprotective effects and suppress the hypercholesterolemia-induced oxidative stress in rats

    Directory of Open Access Journals (Sweden)

    Ali Rezaei-Golmisheh

    2015-07-01

    Results: The highest phenol content, oleanolic acid, quercetin and lupeol levels and free radical scavenging potency were found in the bark extract, and the highest ursolic acid level was found in the berries extract. Orlistat and extracts significantly (P

  5. 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......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 (Ha......CaT) by about 18% while other extract components were ineffective. A panel of biochemical and cell-based assays testing the antioxidative and cytoprotective activites of α-amyrin indicated no antioxidative activity of this compound. α-Amyrin did not protect HaCaT cells against the damage caused by UVB radiation....

  6. Wound healing activity and docking of glycogen-synthase-kinase-3-beta-protein with isolated triterpenoid lupeol in rats.

    Science.gov (United States)

    Harish, B G; Krishna, V; Santosh Kumar, H S; Khadeer Ahamed, B M; Sharath, R; Kumara Swamy, H M

    2008-09-01

    A triterpene compound lupeol isolated from petroleum ether extract of leaves of Celastrus paniculatus was screened for wound healing activity (8 mg/ml of 0.2% sodium alginate gel) by excision, incision and dead space wound models on Swiss Albino rats (175-225 g). In lupeol treated groups wound healing activity was more significant (17.83+/-0.48) than the standard skin ointment nitrofurazone (18.33+/-0.42). Epithelialization of the incision wound was faster with a high rate of wound contraction (571.50+/-5.07) as compared with the control group. In dead space wound model also the weight of the granulation tissue of the lupeol treated animal was increased indicating increase of collagenation and absence of monocytes. The comparative docking of isolated lupeol molecule and standard drug nitrofurazone to glycogen synthase kinase 3-beta protein by Wnt signaling pathway also supported the wound healing property of lupeol. The activation domain of GSK3-beta consisted of Tyr216, with residues Asn64, Gly65, Ser66, Phe67, Gly68, Val70, Lys85, Leu132, Val135, Asp181 in the active pocket docked with lupeol at the torsional degree of freedom 0.5 units with Lamarckian genetic algorithm showed the inhibition constant of 1.38 x 10(-7). The inhibition constant of nitrofurazone was only 1.35 x 10(-4).

  7. 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 . Palazón, J.; Bonfill, R.M.C.M.; Mallol, A.; Moyano, E.; Morales, C.; Pinol, M.T. Elicitation of different Panax ginseng transformed root phenotypes for an improved ginsenoside production. Plant Physiol. Biochem. 2003, 41, 1019–1025. 22. Fritz, V... 19. Kim, O.T.; Kim, S.H.; Ohyama, K.; Muranaka, T.; Choi, Y.E.; Lee, H.Y.; Kim, M.Y.; Hwang, B. Upregulation of phytosterol and triterpene biosynthesis in Centella asiatica hairy roots overexpressed ginseng farnesyl diphosphate synthase. Plant Cell...

  8. [Effect of triterpenoid glycosides on alpha- and beta-amylase activity and total protein content in wheat seedlings].

    Science.gov (United States)

    Davidiants, E S

    2011-01-01

    Influence of the aleanolic acid glycosides from Silphium perfoliatum L. (silphioside B, C, E and G) and their progenins on the amylase activity and total protein content in wheat seedlings was studied. Treatment of the Triticum aestivum L. seeds with 1-10 microM water solutions of mono- and diglycosides (mono- and bisdesmosines) elevated the alpha-amylase and total amylase activities in seedlings. Silphioside E containing three glucose moieties in its molecule did not change alpha-amylase activity, but it did if bis-triglycoside acetylated carbohydrate (as in silphioside C). Effects of 5-10 microM solutions of the active glycosides was comparable with that of exogenous gibberellin A3 and 6-benzylaminopurine.

  9. 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.

  10. Isolation and biological evaluation of novel Tetracosahexaene hexamethyl, an acyclic triterpenoids derivatives and antioxidant from Justicia adhatoda.

    Science.gov (United States)

    Dhankhar, Sandeep; Dhankhar, Seema; Ruhil, Sonam; Balhara, Meenakshi; Malik, Vinay; Chhillar, Anil K

    2014-01-01

    Forty five extracts fraction of nine selected Indian medicinal plants, based on their use in traditional systems of medicine were analyzed for their antioxidant potential. All the extracts were investigated for phenol content value calculated in Gallic acid equivalents (% of GAE) and antioxidant potential. Moreover, total phenolic content (% dw equivalents to gallic acid) of all plant extracts were found in the range of 3.04 to 24.03, which correlated with antioxidant activity. The findings indicated a promising antioxidant activity of crude extracts fractions of three plants (Justicia adhatoda, Capparis aphylla and Aegle marmelos) and required the further exploration for their effective utilization. Results indicated that petroleum ether fraction of J. adhatoda out of three plants also possesses the admirable antioxidant abilities with high total phenolic content. Following, in vitro antioxidant activity-guided phytochemical separation procedures, twelve fractions of petroleum ether extract of J. adhatoda were isolated by silica gel column chromatography. One fraction (Rf value: 0.725) showed the noticeable antioxidant activity with ascorbic acid standard in hydroxyl radical scavenging assays. The molecular structures elucidations of purified antioxidant compound were carried out using spectroscopic studies ((1)H NMR, (13)C NMR and MS). This compound was reported from this species for the first time. The results imply that the J. adhatoda might be a potential source of natural antioxidants and 2,6,10,14,18,22-Tetracosahexaene, 2,6,10,15,19,23-hexamethyl is an antioxidant ingredient in J. adhatoda.

  11. 牛膝中的三萜皂苷类成分%Triterpenoid saponins in roots of Achyranthese bidentata

    Institute of Scientific and Technical Information of China (English)

    魏焕莉; 李艳静; 陈君; 李萍

    2012-01-01

    目的:对牛膝(Achyranthese bidentata B1.)根中的化学成分进行研究.方法:采用D101大孔树脂柱、硅胶柱、反相中压柱、凝胶柱和制备液相进行化学分离和纯化,并利用各种波谱技术进行结构鉴定.结果:从牛膝中分离并鉴定了5个皂苷类化合物,分别为:牛膝皂苷C(1)、牛膝皂苷D(2)、竹节参皂苷Ⅳ(3)、人参皂苷Ro(4)和姜状三七苷R1(5).结论:化合物1为首次从自然界中获得,化合物3为首次从苋科植物中分离得到.%AIM:To study the constituents in the roots of Achyranthese bidentata B1.METHODS:D-101 porous polymer resin column,normal-phase silica gel column chromatography,revised-phase medium pressure column chromatography,Sephadex LH-20 and prep-HPLC were used for the separation,and spectroscopic techniques were employed for the identification of the isolated compounds.RESULTS:Five saponins were isolated and elucidated as achyranthoside C (1),achyranthoside D (2),chikusetsusaponin Ⅳ(3),ginsenoside Ro (4) and zingibroside R1 (5).CONCLUSION:Compound 1 was obtained from natural source for the first time,and compound 3 was reported from the family of Amaranthaceae for the first time.

  12. Hyaluronidase Inhibitory Activity of Pentacylic Triterpenoids from Prismatomeris tetrandra (Roxb. K. Schum: Isolation, Synthesis and QSAR Study

    Directory of Open Access Journals (Sweden)

    Nor Hayati Abdullah

    2016-02-01

    Full Text Available The mammalian hyaluronidase degrades hyaluronic acid by the cleavage of the β-1,4-glycosidic bond furnishing a tetrasaccharide molecule as the main product which is a highly angiogenic and potent inducer of inflammatory cytokines. Ursolic acid 1, isolated from Prismatomeris tetrandra, was identified as having the potential to develop inhibitors of hyaluronidase. A series of ursolic acid analogues were either synthesized via structure modification of ursolic acid 1 or commercially obtained. The evaluation of the inhibitory activity of these compounds on the hyaluronidase enzyme was conducted. Several structural, topological and quantum chemical descriptors for these compounds were calculated using semi empirical quantum chemical methods. A quantitative structure activity relationship study (QSAR was performed to correlate these descriptors with the hyaluronidase inhibitory activity. The statistical characteristics provided by the best multi linear model (BML (R2 = 0.9717, R2cv = 0.9506 indicated satisfactory stability and predictive ability of the developed model. The in silico molecular docking study which was used to determine the binding interactions revealed that the ursolic acid analog 22 had a strong affinity towards human hyaluronidase.

  13. 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......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 (Ha...

  14. 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.

  15. Elicitation of gymnemic acid production in cell suspension cultures of Gymnema sylvestre R.Br. through endophytic fungi.

    Science.gov (United States)

    Netala, Vasudeva Reddy; Kotakadi, Venkata Subbaiah; Gaddam, Susmila Aparna; Ghosh, Sukhendu Bikash; Tartte, Vijaya

    2016-12-01

    The enhancement of plant secondary metabolite production in cell suspension cultures through biotic or abiotic elicitation has become a potential biotechnological approach for commercialization or large-scale production of bioactive compounds. Gymnema sylvestre R.Br. is an important medicinal plant, rich in a group of oleanane triterpenoid saponins called gymnemic acid, well known for its anti-diabetic activity. Two endophytic fungal strains were isolated from the leaves of G. sylvestre and identified as Polyancora globosa and Xylaria sp. based on the PCR amplification and internal transcribed spacer (ITS 1-5.8S-ITS 2) sequencing of 18S rRNA gene. The process of elicitation of cell suspension cultures of G. sylvestre with dried powder of fungal mycelia (DPFM) and extracellular culture filtrate (ECF) of endophytic fungi consistently enhanced the accumulation of gymnemic acid and the DPFM was proved to be an effective elicitor when compared to the ECF. The DPFM elicited the gymnemic acid content in the range of 2.57-10.45-fold, while the ECF elicited the gymnemic acid content in the range of 2.39-7.8-fold. P. globosa, a novel and a rare endophytic fungal strain, has shown a great influence on the production of gymnemic acid. Cell suspension cultures elicited with DPFM of P. globosa produced higher amount of gymnemic acid content (124.23 mg/g dried cell weight) compared to the cultures elicited with DPFM of Xylaria sp. (102.24 mg/g DCW). But the cultures treated with consortium of DPFM of both fungi showed great influence on the production of gymnemic acid (139.98 mg/g DCW) than the cultures treated with DPFM alone. Similarly, cultures treated with consortium of ECF of both fungi produced more gymnemic acid content (94.86 mg/g DCW) compared with cultures treated with ECF of Xylaria sp. (77.93 mg/g DCW) and ECF of P. globosa (78.65 mg/g DCW) alone.

  16. Diffusion dynamics of the Keap1–Cullin3 interaction in single live cells

    Energy Technology Data Exchange (ETDEWEB)

    Baird, Liam [Jacqui Wood Cancer Centre, Division of Cancer Research, Medical Research Institute, University of Dundee, Dundee, Scotland (United Kingdom); Dinkova-Kostova, Albena T., E-mail: a.dinkovakostova@dundee.ac.uk [Jacqui Wood Cancer Centre, Division of Cancer Research, Medical Research Institute, University of Dundee, Dundee, Scotland (United Kingdom); Department of Pharmacology and Molecular Sciences, Johns Hopkins University School of Medicine, Baltimore, MD (United States)

    2013-03-29

    Highlights: ► We developed a quantitative FRAP-based system to study the Keap1–Cul3 interaction. ► We show that Keap1–EGFP and mCherry–Cul3 interact in single live cells. ► We used inducers which target distinct cysteine sensors of Keap1 and differ 4000-fold in potency. ► Inducers cause Nrf2 stabilization, nuclear translocation, and target gene expression. ► Inducers of four different types do not dissociate the Keap1–EGFP:mCherry–Cul3 complex. -- Abstract: Transcription factor NF-E2 p45-related factor 2 (Nrf2) regulates the expression of a network of genes encoding drug-detoxification, anti-inflammatory, and metabolic enzymes, as well as proteins involved in the regulation of cellular redox homeostasis. Under basal conditions, Kelch-like ECH associated protein 1 (Keap1) targets Nrf2 for ubiquitination and proteasomal degradation via association with Cullin3 (Cul3)-based Rbx1 E3 ubiquitin ligase. Various small molecules (inducers) activate Nrf2 leading to upregulation of cytoprotective gene expression. Inducers chemically modify specific cysteine residues of Keap1 which ultimately loses its ability to target Nrf2 for degradation. Dissociation of the Keap1–Cul3 complex by inducers is one possible mechanism, but evidence in single live cells is lacking. To investigate the diffusion dynamics of the Keap1–Cul3 interaction and the effect of inducers, we developed a quantitative fluorescence recovery after photobleaching (FRAP)-based system using Keap1–EGFP and mCherry–Cul3 fusion proteins. We show that Keap1–EGFP and mCherry–Cul3 interact in single live cells. Exposure for 1 h to small-molecule inducers of 4 different types, the oleanane triterpenoid CDDO, the isothiocyanate sulforaphane, the sulfoxythiocarbamate STCA, and the oxidant hydrogen peroxide which target distinct cysteine sensors within Keap1 with potencies which differ by nearly 4000-fold, does not dissociate the Keap1–Cul3 complex. As inducers cause conformational changes

  17. A liquid chromatography-atmospheric pressure photoionization tandem mass spectrometric (LC-APPI-MS/MS) method for the determination of triterpenoids in medicinal plant extracts.

    Science.gov (United States)

    Gobo, Luciana Assis; Viana, Carine; Lameira, Osmar Alves; de Carvalho, Leandro Machado

    2016-08-01

    An analytical method using liquid chromatography-atmospheric pressure photoionization tandem mass spectrometry with toluene as a dopant was developed for the determination of triterpenes in medicinal plant extracts. The 12 compounds determined have been shown to exhibit biological activity, such as gastroprotective, hepatoprotective, anti-inflammatory, antiviral and anti-tumor effects. The parameters of the atmospheric pressure photoionization interface were optimized to obtain the highest possible sensitivity for all of the compounds. The limits of detection and quantification ranged from 0.4 to 157.9 µg l(-1) and 1.3 to 526.4 µg l(-1) , respectively. The method was validated and applied to extracts of five medicinal plants species (Mansoa alliacea (Lam.) A.H.Gentry, Bauhinia variegata var variegata, Bauhinia variegata var alboflava, Cecropia obtuse Trécul and Cecropia palmate Willd) from the Amazonian region. The concentrations of the six triterpenes quantified in the samples ranged from 0.424 mg kg(-1) for ursolic acid to 371.96 mg kg(-1) for β-amyrin, which were quantified by using the standard addition method (n = 3). Copyright © 2016 John Wiley & Sons, Ltd.

  18. Lupeol, a triterpenoid isolated from Calotropis gigantea latex ameliorates the primary and secondary complications of FCA induced adjuvant disease in experimental rats.

    Science.gov (United States)

    Saratha, Venkatesan; Subramanian, Sorimuthu Pillai

    2012-02-01

    Rheumatoid arthritis (RA) is a chronic inflammatory autoimmune disorder that affects 1% of the adult population worldwide. Calotropis gigantea is a xerophytic, latex producing medicinal plant widely distributed in nature. Different parts of the plant have been traditionally used for the treatment of various ailments including arthritis. In the present study, we have isolated and characterized lupeol, a pentacyclic triterpene from the dialyzable fraction of the latex and evaluated the anti-arthritic properties of lupeol in Freund's Complete Adjuvant (FCA) induced arthritis in rats. Lupeol (50 mg/kg b.w/day) was administered orally to AA rats for 4 weeks. The alterations in body weight gain, paw volume, RBC, WBC, Hb, EPO, ESR, platelets and PCV were recorded. The activities of serum AST, ALT and ALP were also assayed. The levels of lipid profile were estimated. The levels of pro-inflammatory cytokines as well as anti-inflammatory cytokines such as TNF-α, IL-1β, IL-6 and IL-10 were also analyzed. The results of present study indicate the anti-inflammatory and anti-arthritic activity of lupeol present in the C. gigantea latex.

  19. Biflavones and triterpenoids isolated from Ouratea castaneifolia (DC. Engl., Ochnaceae Biflavonas e triterpenóides isolados de Ouratea castaneifolia (DC. Engl., Ochnaceae

    Directory of Open Access Journals (Sweden)

    Luís Adriano S. do Nascimento

    2009-12-01

    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.O presente trabalho trata da investigação química das folhas e caule da espécie Ouratea castaneifolia (DC. Engl., sobre a qual não há registros de estudos químicos ou farmacológicos anteriores. O estudo fitoquímico clássico dos extratos orgânicos do caule e das folhas de O. castaneifolia foi aliado à técnica da cromatografia líquida de alta eficiência (CLAE e resultou na identificação de dezessete metabólitos: sete triperpenos (friedelina, 3β-friedelinol, α-amirina, β-amirina, lupeol, taraxerol e germanicol, quatro esteróides (sitosterol, estigmasterol e os glucosídeos sitosteril 3-O-β-D-glicopiranosídeo e estigmasteril 3-O-β-D-glicopiranosídeo, uma isoflavona (5,7,4´-trimetoxiisoflavona, uma flavona (5,4´-diidroxi-7,3´,5´-trimetoxiflavona, quatro biflavonas (amentoflavona, 7,7"-O-dimetil-amentoflavona, heveaflavona e tetrametilamentoflavona. A identificação das substâncias foi feita com base na análise de espectros de RMN de ¹H, 13C e técnicas bidimensionais. As classes dos metabólitos identificados estão de acordo com aquelas citadas em estudos químicos do gênero Ouratea.

  20. Studies on triterpenoids and steroids from Balanophora involucrata%筒鞘蛇菰的三萜及甾醇成分研究

    Institute of Scientific and Technical Information of China (English)

    夏新中; 韩宏星; 屠鹏飞

    2001-01-01

    Object The chemical constituents of Balanophora involucrata Hook.f. (Balanophoraceae) were studied. Methods Individual constituent was isolated and repeatedly purified on silica gel column, identified by physico-chemical constants and structurally elucidated by spectral analysis. Results From the petroleum ether and ethylacetate extracts, 8 compounds were obtained, 6 of them were identified as: ursa-12-ene-11-one-3-ol-octocosate (Ⅰ),β-amyrin hexadecanate (Ⅱ),β-amyrin (Ⅲ),lupeol (Ⅳ),β-sitosterol (Ⅴ) and β-sitosterol glucoside (Ⅵ). Conclusion All of these compounds, with the exception of Ⅴ, were obtained from this plant for the first time, and compound I was a new one.%目的 研究蛇菰科筒鞘蛇菰Balanophora involicrataHook.f.的化学成分。方法 采用反复硅胶柱层析分离纯化,通过理化常数测定和光谱分析鉴定其化学结构。结果 从筒鞘蛇菰的石油醚和乙酸乙酯萃取部分共分得8个化合物,鉴定了其中的6个,即:熊果烷-12-烯-11-羰基-3-醇正二十八酸酯(ursa-12-ene-11-one-3-ol octocosate,Ⅰ)、β-香树酯醇正十六酸酯(β-amyrin hexadecanate,Ⅱ)、β-香树脂醇(β-amyrin,Ⅲ)、羽扇豆醇(lupeol,Ⅳ)、β-谷甾醇(β-sitosterol,Ⅴ)和β-谷甾醇葡萄糖苷(β-sitosterol glucoside,Ⅵ)。结论 除Ⅴ外,各化合物均为首次从该植物中分得,其中化合物Ⅰ为新化合物。

  1. A new lanostane-type triterpenoid from Cymbopogon citratus%香茅中一个新羊毛脂烷类三萜化合物

    Institute of Scientific and Technical Information of China (English)

    张孟孟; 孙丽丽; 利程; 高万; 杨建波; 王爱国; 苏亚伦; 吉腾飞

    2014-01-01

    研究香茅Cymbopogon citratus的化学成分.采用硅胶,Sephadex LH-20和高效液相色谱法从中分离得到8个化合物,包括1个新化合物,通过理化性质和波谱数据分析鉴定其结构分别为3β-甲氧基羊毛甾-9(11)-烯-27-醇(1),3β-羟基羊毛脂-9(11)-烯(2),(24S)-3β-甲氧基羊毛甾-9(11),25-二烯-24-醇(3),8-羟基-新薄荷醇(4),(2E)-3,7-二甲基-2,7-辛二烯-1,6-二醇(5),(+)-香茅醇(6),7-羟基薄荷醇(7)和十九烷酸乙酯(8).其中化合物1为新化合物,化合物2~3为首次从该植物中分离得到.

  2. 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.

  3. 19a-hydroxy-3-oxo-ursa-1,12-dien-28-oic acid, an antiplasmodial triterpenoid isolated from Canthium multiflorum

    DEFF Research Database (Denmark)

    Traore, Maminata; Ziegler, Hanne Lindvig; Olsen, C Erik

    2009-01-01

    A bioactivity guided fractionation of roots of Canthium multiflorum led to the isolation of the new ursenoic acid derivative 19alpha-hydroxy-3-oxo-ursa-1,12-dien-28-oic acid (1), which showed antiplasmodial effect without inducing change of the shape of membranes of erythrocytes....

  4. Synthesis and cytotoxicity of 28-carboxymethoxy lupane triterpenoids. Preference of 28-O-acylation over 28-O-alkylation of betulin by ethyl bromoacetate

    Institute of Scientific and Technical Information of China (English)

    Aye Aye Mar; Ali Koohang; Nathan D. Majewski; Erika L. Szotek; David A. Eiznhamer; Michael T. Flavin; Ze Qi Xu

    2009-01-01

    28-Carboxymethoxy lupane tritepenoids 3 and 4 were synthesized by alkylation of betulin with the THP protected 2-hydroxyethyl iodide followed by oxidation and reduction. Direct reaction of betulin (5) or betulone (10) with ethyl bromoacetate led to 28-O-acylation, instead of 28-O-alkylation. The targeted compounds 3 and 4 were not cytotoxic at the highest concentration tested (75 μmol/L), suggesting that elongation of the chain length at the 28-position in both betulinic acid (1) and betulonic acid (2) was detrimental to the cytotoxicity. The acylation products 28-O-bromoacetates (8a, 8b and 11) and 28-O-methoxyacetate 13 exhibited cytotoxicity against several cancer cell lines tested.

  5. Antcin K, a Triterpenoid Compound from Antrodia camphorata, Displays Antidiabetic and Antihyperlipidemic Effects via Glucose Transporter 4 and AMP-Activated Protein Kinase Phosphorylation in Muscles

    Directory of Open Access Journals (Sweden)

    Yueh-Hsiung Kuo

    2016-01-01

    Full Text Available The purpose of this study was to screen firstly the potential effects of antcin K (AnK, the main constituent of the fruiting body of Antrodia camphorata, in vitro and further evaluate the activities and mechanisms in high-fat-diet- (HFD- induced mice. Following 8-week HFD-induction, mice were treated with AnK, fenofibrate (Feno, metformin (Metf, or vehicle for 4 weeks afterward. In C2C12 myotube cells, the membrane GLUT4 and phospho-Akt expressions were higher in insulin and AnK-treated groups than in the control group. It was observed that AnK-treated mice significantly lowered blood glucose, triglyceride, total cholesterol, and leptin levels in AnK-treated groups. Of interest, AnK at 40 mg/kg/day dosage displayed both antihyperglycemic effect comparable to Metf (300 mg/kg/day and antihypertriglyceridemic effect comparable to Feno (250 mg/kg/day. The combination of significantly increased skeletal muscular membrane expression levels of glucose transporter 4 (GLUT4 but decreased hepatic glucose-6-phosphatase (G6 Pase mRNA levels by AnK thus contributed to a decrease in blood glucose levels. Furthermore, AnK enhanced phosphorylation of AMP-activated protein kinase (phospho-AMPK expressions in the muscle and liver. Moreover, AnK treatment exhibited inhibition of hepatic fatty acid synthase (FAS but enhancement of fatty acid oxidation peroxisome proliferator-activated receptor α (PPARα expression coincident with reduced sterol response element binding protein-1c (SREBP-1c mRNA levels in the liver may contribute to decreased plasma triglycerides, hepatic steatosis, and total cholesterol levels. The present findings indicate that AnK displays an advantageous therapeutic potential for the management of type 2 diabetes and hyperlipidemia.

  6. Study on triterpenoid and flavonoid contents of Rabdosia japonica%蓝萼香茶菜的三萜和黄酮类化学成分

    Institute of Scientific and Technical Information of China (English)

    刘洪川; 金永生; 陈海生

    2013-01-01

    目的 对蓝萼香茶菜(Rabdosia japonica)的化学成分进行分离及鉴定.方法 利用硅胶色谱、Sephadex LH-20色谱以及反相高效液相色谱等手段进行分离纯化,应用质谱、磁共振等光谱方法对分得的化合物进行结构鉴定.结果 共分离并鉴定10个化合物,其中包括4个三萜:齐墩果酸(oleanolic acid,1)、熊果酸(ursolic acid,2)、2α-羟基熊果酸(2α-hydroxyursolic acid,3)、2α,23-二羟基熊果酸(2α,23-dihydroxyursolic acid,4);6个黄酮类化合物:槲皮素(quercetin,5)、芹菜素(apiginin,6)、木犀草素(luteolin,7)、芦丁(rutin,8)、异鼠李素(isorhamnetin,9)、小麦黄素(tricin,10).结论 化合物9、10为首次从该植物中分离得到.

  7. 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.

  8. Isolation of degraded pentacyclic triterpenoid acids in a Nigerian crude oil and their identification as tetracyclic carboxylic acids resulting from ring A cleavage

    Science.gov (United States)

    Schmitter, J. M.; Arpino, P. J.; Guiochon, G.

    1981-10-01

    Three tetracyclic acids were identified in a Nigerian crude oil, after reduction and deuterium labelling followed by GC/MS investigation. Two of them are identical to 3:4 seco acids previously identified in sediments. The third one is a novel C 24 acid that has not been reported up to now. These geochemical markers are assumed to belong to the class of photochemical tetracyclic triterpenes formed by decay of pentacyclic 3-ketoterpenoids.

  9. 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.

  10. Characterization of 3alpha-acetyl-11-keto-alpha-boswellic acid, a pentacyclic triterpenoid inducing apoptosis in vitro and in vivo.

    Science.gov (United States)

    Büchele, Berthold; Zugmaier, Waltraud; Estrada, Aidee; Genze, Felicitas; Syrovets, Tatiana; Paetz, Christian; Schneider, Bernd; Simmet, Thomas

    2006-11-01

    3Alpha-acetyl-11-keto-alpha-boswellic acid (3alpha-acetoxy-11-oxo-olean-12-en-24-oic acid, 1) was synthesized by a radical-type reaction using bromine and 3alpha-acetyl-alpha-boswellic acid isolated from the oleo-gum-resin of Boswellia carterii. 1D and 2D NMR (COSY, HMBC, ROESY) at 500 MHz were used for shift assignments and structure verification. The compound investigated is present in a herbal preparation extracted from Boswellia serrata oleo-gum-resin, it inhibits the growth of chemotherapy-resistant human PC-3 prostate cancer cells in vitro and induces apoptosis as shown by activation of caspase 3 and the induction of DNA fragmentation. In addition, compound 1 is active IN VIVO as shown by inhibition of proliferation and induction of apoptosis in PC-3 prostate cancer cells xenotransplanted onto the chick chorioallantoic membrane.

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

    Science.gov (United States)

    Mishra, Smrati; Bansal, Shilpi; Mishra, Bhawana; Sangwan, Rajender Singh; Asha; Jadaun, Jyoti Singh; Sangwan, Neelam S

    2016-01-01

    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.

  12. Optimization of Ultrasound Extraction of Total Triterpenoids from Synsepalum dulcificum Leaf by Response Surface Methodology%响应面法优化神秘果叶总三萜的超声波提取工艺

    Institute of Scientific and Technical Information of China (English)

    卢圣楼; 刘红; 臧文霞; 李芸; 张强; 王子欢

    2013-01-01

    采用响应面法优化超声波提取海南产神秘果叶总三萜的最佳工艺条件.在单因素试验的基础上,选取乙醇体积分数、提取温度、液料比和超声波作用时间作为影响因子,根据BoxBehnken中心组合原理设计4因素3水平试验,以神秘果叶总三萜的得率为响应值进行响应面分析.得到超声波提取神秘果叶总三萜的最优工艺条件为:1.0g神秘果叶,乙醇体积分数70%,提取温度50℃,液料比30∶ 1(mL∶g)和超声波作用时间33 min,实际得率0.92%,与模型预测值(0.94%)基本相符.

  13. 灵芝三萜类化合物抗癌作用机制的研究进展%Mechanisms of anticancer action of triterpenoids from Ganoderma lucidum: A review of recent researches

    Institute of Scientific and Technical Information of China (English)

    刘高强; 丁重阳; 王晓玲

    2007-01-01

    @@ INTRODUCTION Ganoderma lucidum (Fr.) P. Karst., a species of higher fungus called "Lingzhi" in China or "Reishi" and "Mannendake" in Japan, has been used in the traditional Chinese medicine (TCM) for prevention and treatment of various kinds of diseases, such as cancer, hepatopathy, arthritis, hypertension, neurasthenia, chronic hepatitis,and gastric ulcer (Yang et al., 2000; Hsieh & Yang 2004; Song et al., 2004).

  14. Remarks on Sasidharan et al. “Evaluation of the Hepatoprotective Effects of Lantadene A, a Pentacyclic Triterpenoid of Lantana Plants against Acetaminophen-induced Liver Damage”. Molecules 2012, 17, 13937-13947

    Directory of Open Access Journals (Sweden)

    Manu Sharma

    2013-03-01

    Full Text Available An article by Sasidharan et al. recently published in the journal Molecules [1] claimed to show the hepatoprotective effects of lantadene A against acetaminophen-induced liver damage in mice. While reading this paper, I came across certain points that need to be clarified and taken up in the interest of science and other scientists working in this area.

  15. Preparation of nanosuspension-based gel of Ganoderma lucidum triterpenoids and its in vitro transdermal diffusion characteristics%灵芝三萜纳米混悬凝胶剂的制备及其体外透皮研究

    Institute of Scientific and Technical Information of China (English)

    沈成英; 申宝德; 徐平华; 李晓荣; 闵红燕; 韩晋; 袁海龙

    2014-01-01

    目的 研制灵芝三萜纳米混悬凝胶剂(GT-NS-gel),并进行体外透皮研究.方法 采用高压均质法制备灵芝三萜纳米混悬剂(GT-NS),然后进一步制成凝胶剂.以24 h体外累积释放率和24 h后皮肤中的滞留量为指标,通过效应面法优化GT-NS-gel的处方;比较优化后的GT-NS-gel和灵芝三萜凝胶剂(GT-gel)的体外经皮渗透量及滞留量.结果 以最优处方:5 mg/g卡波姆940、30 mg/g GT、47.2 mg/g卵磷脂制得的GT-NS-gel在24 h时的体外累积释放率为(56.28±2.16)%,24 h皮肤滞留量为(472.89±8.74) μg/cm2,理论预测值与实测值接近,模型具有良好的预测性;GT-NS-gel 24 h药物累积渗透量和皮肤滞留量分别为(50.73±4.97)和(475.89±10.74) μg/cm2,明显高于GT-gel的(14.79±3.45)和(101.32±7.02) μg/cm2(P<0.05).结论 将灵芝三萜制成纳米混悬凝胶剂,能够增加药物的皮肤滞留量,提高药物在皮肤局部的生物利用度.

  16. Determination of total triterpenoid saponin in Albizia julibrissin Durazz. By UV%紫外分光光度法测定合欢皮总皂苷的含量

    Institute of Scientific and Technical Information of China (English)

    冯磊; 陈爽; 邱丽颖; 金坚

    2009-01-01

    目的 建立测定合欢皮总皂苷含量的方法.方法 采用紫外分光光度法,以齐墩果酸为对照品,测定合欢皮总皂苷的含量,并分析方法的可行性.结果 合欢皮提取物中总皂苷的含量可达63.49%,加样同收率为107.86%.结论 新建方法操作简便,精密度、准确度、重复性均好,可用于合欢皮总皂苷的含量测定及质量控制.

  17. Separation and characterization of phenolic compounds and triterpenoid saponins in licorice (Glycyrrhiza uralensis) using mobile phase-dependent reversed-phase×reversed-phase comprehensive two-dimensional liquid chromatography coupled with mass spectrometry.

    Science.gov (United States)

    Qiao, Xue; Song, Wei; Ji, Shuai; Wang, Qi; Guo, De-an; Ye, Min

    2015-07-10

    Licorice is one of the most popular herbal medicines worldwide. It contains a big array of phenolic compounds (flavonoids, coumarins, and diphenylethanones). Due to high structural diversity, low abundance, and co-elution with licorice saponins, these phenolic compounds are difficult to be separated by conventional chromatography. In this study, a mobile phase-dependent reversed-phase×reversed phase comprehensive two-dimensional liquid chromatography (RP×RP 2DLC) method was established to separate phenolic compounds in licorice (the roots of Glycyrrhiza uralensis). Organic solvents in the mobile phase were optimized to improve orthogonality of the first and second dimensions, and a synchronized gradient mode was used to improve chromatographic resolution. Finally, licorice extracts were eluted with methanol/water/formic acid in the first dimension (Acquity CSH C18 column), and acetonitrile/water/formic acid in the second dimension (Poroshell Phenyl-Hexyl column). By using this 2DLC system, a total of 311 compounds were detected within 40min. The practical and effective peak capacity was 1329 and 524, respectively, and the orthogonality was 79.8%. The structures of 21 selected unknown compounds were tentatively characterized by mass spectrometry, and 8 of them were discovered from G. uralensis for the first time. The mobile phase-dependent 2DLC/MS system could benefit the separation and characterization of natural products in complicated herbal extracts.

  18. Extracting triterpenoids from Hyptis suaveolens( L. ) Piot.by two steps of release and hot-extraction%解吸-热提两步法提取毛老虎中的三萜酸研究

    Institute of Scientific and Technical Information of China (English)

    黄秀香; 韦瑞松; 赖红芳

    2008-01-01

    用解吸-热提两步提取法,以乙醇为解吸剂和热提剂提取毛老虎茎中的三萜酸.考察了乙醇浓度和用量对提取率的影响.结果表明,两步法提取毛老虎中三萜酸的最佳操作参数为:解吸剂乙醇浓度为50%,用量为样品量的3倍,解吸时间4 min;热提乙醇浓度50%,用量为样品量的7.5倍,热提时间24 min,三萜酸得率0.292%.

  19. Orthogonal Experiment of the Extraction of Triterpenoids from Stems of Hyptis suaveolens with Microwave%微波提取毛老虎茎中总三萜酸的正交实验研究

    Institute of Scientific and Technical Information of China (English)

    黄秀香; 林翠梧; 陈丽芬; 袁霞; 宁自华

    2008-01-01

    目的:研究微波法提取毛老虎茎中总三萜酸的最佳工艺.方法:采用正交实验,考察时间(A)、温度(B)、固液比(C)、NaOH浓度(D)4个因素的影响.结果:微波提取优化工艺条件是A1B2C3D2.结论:微波提取具有提取率高,提取速率快,提取温度低,能量消耗小等特点,用于中草药的提取应用前景广阔.

  20. 分光光度法测定毛老虎茎中三萜酸的总含量%Determination of Total Content of Triterpenoids in Stems of Hyptis suaveolens (L.) Piot by Spectrophotometry

    Institute of Scientific and Technical Information of China (English)

    黄秀香; 袁霞; 林翠梧; 陈丽芬

    2007-01-01

    目的 建立香草醛-冰醋酸体系分光光度法测定毛老虎中总三萜酸的方法.方法 利用在高氯酸的条件下香草醛-冰醋酸与三萜酸的反应测定总三萜酸.结果 总三萜酸在2.53~13.14 μg/ml呈良好的线性关系,测定样品回收率为99.07%.结论 该法简便、快速、灵敏.

  1. Loading of erythrocyte membrane with pentacyclic triterpenes inhibits Plasmodium falciparum invasion.

    Science.gov (United States)

    Ziegler, Hanne L; Staalsø, Trine; Jaroszewski, Jerzy W

    2006-06-01

    Lupeol and betulinic acid inhibit the proliferation of Plasmodium falciparum parasites by inhibition of the invasion of merozoites into erythrocytes. This conclusion is based on experiments employing parasite cultures synchronized by magnetic cell sorting (MACS). Identical inhibitory effects were observed upon incubation of synchronous parasite cultures in the presence of the triterpenoids, and when the parasite cultures were grown in a triterpenoid-free medium with erythrocytes preloaded with the triterpenoids.

  2. A Novel Triterpenic Acid from Gymnema sylvestre

    Institute of Scientific and Technical Information of China (English)

    Shu Lin PENG; Xu Min ZHU; Ming Kui WANG; Li Sheng DING

    2005-01-01

    A novel oleanane-type triterpenic acid was isolated from the leaves of Gymnema sylvestre (Asclepiadaceae). The structure was characterized as 3β, 16β, 22β, 28-tetrahydroxy- olean-12-en-30-oic acid on the basis of spectral evidence, including 1D- and 2D-NMR (HMQC, HMBC, 1H-1H COSY and NOESY).

  3. Efektivitas Ekstrak Daun Jambu Biji Buah Putih Terhadap Pertumbuhan Staphylococcus aureus Dari Abses Dan Staphylococcus aureus (ATCC® 29213™)

    OpenAIRE

    Sinurat, Jojor

    2016-01-01

    Daun jambu biji mengandung senyawa aktif seperti tanin, triterpenoid, flavonoid, saponin yang mempunyai efek antibakteri. Mekanisme tanin sebagai antibakteri dengan mengkerutkan dinding sel dan membran sel, inaktivasi enzim, inaktivasi fungsi materi genetik bakteri. Flavonoid merusak sel bakteri, denaturasi protein, inaktivasi enzim dan menyebabkan lisis. Triterpenoid dan saponin menghambat pertumbuhan Staphylococcus aureus dengan cara merusak struktur membran sel. Staphylococcus aureus adala...

  4. 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

  5. Two New Saponins from Lysimachia capillipes Hemsl

    Institute of Scientific and Technical Information of China (English)

    Jing-Kui TIAN; Zhong-Mei ZOU; Li-Zhen XU; Shi-Lin YANG

    2005-01-01

    To investigate the saponins from whole plants of Lysimachia capillipes Hemsl., two new saponins, named capilliposide E (1) and capilliposide F (2), were isolated. The structures of the new sa ponins were elucidated as 3 β, 22α-dihydroxy- 16α-acetat-28→ 13 -lactone-oleanane-3 -O- [β-D-glucopyranosyl(1→2)-α-L-arabinpyranoyl]-22-O-β-D-glucopyranoside (1) and 3 β, 22α-dihydroxy- 16α-acetat-28→ 13-1actone-oleanane-3-O- { [β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl-(1→4)]-α-L-arabinpyranoyl }-22-O-βD-glucopyranoside (2). The structures of these compounds were determined by 1D- and 2D-NMR, MS techniques, and chemical methods.

  6. Beckmann rearrangement within the ring C of oleanolic acid lactone: Synthesis, structural study and reaction mechanism analysis

    Science.gov (United States)

    Froelich, Anna; Bednarczyk-Cwynar, Barbara; Zaprutko, Lucjusz; Gzella, Andrzej

    2017-05-01

    Synthesis, spectral and X-ray analysis of three compounds, i.e. 3β-acetoxy-12-hydroxyimino-18β-oleanan-28,13β-olide (substrate) and 3β-acetoxy-12-nitrile-12,13-seco-15(14 → 13)-abeoolean-14(27)-en-28,13β-olide and 3β-acetoxy-12-oxo-12a-aza-C-homoolean-13(18)-en-28-oic acid (Beckmann rearrangement reaction products) are described. Structural analysis revealed that the oxime group in the ring C in substrate molecule had an E-configuration. The nitrile product with retained lactone group was a result of major transformations within rings C and D of oleanane skeleton. In lactam product free carboxyl group and a double bond in ring D instead of lactone system were formed in Beckmann rearrangement reaction.

  7. Age correlation of petroleum of unknown source using biological markers

    Energy Technology Data Exchange (ETDEWEB)

    Moldowan, J.M.; Jacobson, S.R.; Lee, C.Y. (Chevron Oil Field Research Co., Richmond, CA (USA)); Huizinga, B.J. (Chevron Overseas Petroleum, Inc., San Ramon, CA (USA))

    1990-05-01

    Determination of age constraints on petroleums from unknown sources provides a means of choosing among possible source rock candidates, predicting migration scenarios for oil, and determining the timing of its emplacement in the reservoir. A number of parameters used to assign such age constraints to petroleum have been suggested by geochemists. However, any constraining marker, regardless of age, may not be found in a particular facies because the parent organisms are absent in those sediments. Thus, the presence of a specific age correlation marker may be significant whereas its absence may not. The authors have investigated two markers for their age-correlation significance. Oleanane, a marker related to pentacyclic triterpanes in flowering plants (angiosperms) occurs in many Late Cretaceous or younger rocks and oils, even though angiosperm fossils are known in older rocks. A survey of a sequence of middle to upper Cretaceous rocks from Wyoming provides an example of a Late Cretaceous age for the onset of oleanane. However, a level of uncertainty exists for older Cretaceous rocks where a trace component with many similarities to oleanane (which could in fact be oleanane) can occur. C{sub 30}-steranes (24-n-propylcholestanes) have been used as a widely occurring marker for marine organic input to petroleum. A recent report postulates the origin of C{sub 30}-steranes from marine Sarcinochrysidales order of Chrysophycase (golden brown algae). Although the fossil record of these algae has not been recorded, their sample base indicates that C{sub 30} steranes, and therefore their parent organisms, originate in the Middle Ordovician.

  8. Pentacyclic Triterpene Distribution in Various Plants – Rich Sources for a New Group of Multi-Potent Plant Extracts

    OpenAIRE

    Armin Scheffler; Laszczyk, Melanie N.; Holger Trojan; Thomas Kopp; Sebastian Jäger

    2009-01-01

    Pentacyclic triterpenes are secondary plant metabolites widespread in fruit peel, leaves and stem bark. In particular the lupane-, oleanane-, and ursane triterpenes display various pharmacological effects while being devoid of prominent toxicity. Therefore, these triterpenes are promising leading compounds for the development of new multi-targeting bioactive agents. Screening of 39 plant materials identified triterpene rich (> 0.1% dry matter) plant parts. Plant materials with high triterp...

  9. 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.

  10. New terpenoids, olibanumols D-G, from traditional Egyptian medicine olibanum, the gum-resin of Boswellia carterii.

    Science.gov (United States)

    Morikawa, Toshio; Oominami, Hideo; Matsuda, Hisashi; Yoshikawa, Masayuki

    2011-01-01

    A new prenylaromadendrane-type diterpene, olibanumol D (1), and three new oleanane- and lupane-type triterpenes, olibanumols E (2), F (3), and G (4), were isolated from the traditional Egyptian medicine olibanum, the exuded gum-resin from Boswellia carterii Birdw. Their structures were established mainly on the basis of 1D and 2D NMR spectral data. Compounds 1 and 2 exhibited nitric oxide production inhibitory activity in lipopolysaccharide-activated mouse peritoneal macrophages.

  11. Reference: 69 [Arabidopsis Phenome Database[Archive

    Lifescience Database Archive (English)

    Full Text Available nts. Pleiotropic phenotypes were rescued by feeding with squalene, the precursor of sterols...ggest that HMG1 plays a critical role in triterpene biosynthesis, and that sterols and/or triterpenoids cont

  12. Inhibitory effects of constituents from Morus alba var. multicaulis on differentiation of 3T3-L1 cells and nitric oxide production in RAW264.7 cells

    National Research Council Canada - National Science Library

    Yang, Zhi-Gang; Matsuzaki, Keiichi; Takamatsu, Satoshi; Kitanaka, Susumu

    2011-01-01

    .... multicaulis Perro. (Moraceae). Their structures were determined by spectroscopic methods. The prenyl-flavonoids 11-14, 16, triterpenoids 17,18 and 20 showed significant inhibitory activity towards the differentiation of 3T3-L1 adipocytes...

  13. Phytochemical Observation on Leaf of Justicia Tranquebariesis. L.F.

    Science.gov (United States)

    Akilandeswari, S.; Mainmaran, S.; Valarmathi, R.; Kumara, S. Karpagam; Loganathan, Sundari V.

    2001-01-01

    Photochemical studies of leaf of the herbs Justicia tranquebariensis. (Acanthaceae) carried out in the presence of phytosterols, flavonoids, Glycosides and absence of triterpenoids, alkaloids, saponins tannins have been reported in this herb for the first time. PMID:22557013

  14. Enlightening the past: analytical proof for the use of Pistacia exudates in ancient Egyptian embalming resins.

    Science.gov (United States)

    Nicholson, Tim M; Gradl, Manuela; Welte, Beatrix; Metzger, Michael; Pusch, Carsten M; Albert, Klaus

    2011-12-01

    Mastic, the resinous exudate of the evergreen shrub Pistacia lentiscus, is frequently discussed as one of the ingredients used for embalming in ancient Egypt. We show the identification of mastic in ancient Egyptian embalming resins by an unambiguous assignment of the mastic triterpenoid fingerprint consisting of moronic acid, oleanonic acid, isomasticadienonic and masticadienonic acid through the consolidation of NMR and GC/MS analysis. Differences in the observed triterpenoid fingerprints between mummy specimens suggest that more than one plant species served as the triterpenoid resin source. Analysis of the triterpenoid acids of ancient embalming resin samples in the form of their methyl- and trimethylsilyl esters is compared. In addition we show a simple way to differentiate between residues of mastic from its use as incense during embalming or from direct mastic application in the embalming resin.

  15. 太白银莲花皂苷-A诱导人胶质瘤U87细胞凋亡及其机制研究%A novel triterpenoid taipaienoside A induces human glioma U87ceils apoptosis and the mechanism research

    Institute of Scientific and Technical Information of China (English)

    刘宁; 程光; 汤海峰; 费舟

    2013-01-01

    目的 探讨太白银莲花皂苷A诱导胶质瘤U87细胞株细胞凋亡作用及机制.方法 以四甲基偶氮唑蓝(MTT)比色法检测太白银莲花皂苷A对U87细胞和VEC304细胞存活率的影响;Hoechst 33342核染色后荧光显微镜下观察细胞核形态学变化;透射电子显微镜观察太白银莲花皂苷A处理后U87细胞超微结构;流式细胞仪AnnexinV/IP双染检测太白银莲花皂苷A处理后U87细胞凋亡比率;免疫印迹法(Western blot)检测致凋亡分子Fas、Fas-L、Pro-Caspase8、Pro-Caspase3、Bcl-2、Bax等表达情况.结果 板低浓度(<5 rmg/L)下太白银莲花皂苷A处理后U87细胞生存率明显下降,同比正常EVC304细胞生存率影响不显著;Hoechst 33342核染色及透射电镜下均可见典型细胞凋亡形态学变化;流式细胞仪分析显示低浓度太白银莲花皂苷A(1.75 mg/L IC50)处理后U87细胞系早期凋亡细胞比率随时间递增,呈明显时间依赖性;免疫印迹实验发现太白银莲花皂苷A处理U87细胞6,12,24h后细胞Fas及Fas-L表达递增,Pro-Casosse8、ProCaspase3递减,活化Caspase-3片段12h达到峰值,Bcl-2表达差别不显著,Bax表达未测出.结论 太白银莲花皂苷A能够诱导U87细胞凋亡,并且其机制与Fas介导的表面受体凋亡通路有关.%Objective It is to investigate the potential apoptosis-inducing effect and the mechanisms of a novel triterpe-noid-taipaienoside A on human glioma U87 cell lines. Methods The viability of U87 and VEC304 cells treated by taipaienoside A was detected by methyl thiazolyl tetrazolium ( MIT) chromatometry; Cytomorphology changes was observed on fluorescence microscope after staining cell chromosome by Hoechst33342. Transmission electron microscope (TEM) was also applied to reveal infrastructure of U87 cells treated by taipaienoside A. The proportions of apoptotic cells were evaluated by flow cyto-metric Annexin V/IP staining analysis. To probe the apoptotic mechanisms induced by taipaienoside A, expressions of Fas, Fas - L, Pro - caspase8, Pro - caspase3, Bel - 2, and Bax in U87 cells were examined via Western Blot analysis. Results The viability of U87 cells declined significantly after treated with taipaienoside A at extremely low concentrations ( <5 mg/L) , and normal cells VEC304 were not influenced significantly in compare; Typical apoptosis morphology changes were observed both in Hoechst33342 staining assay and TEM; The proportions of apoptosis in U87 cells at early stage increased time-depend-ently after treated with taipaienoside A (1.75 mg/L) for indicate time in Annexin V/PI staining assay; Fas and Fas - L expression was up-regulated in U87 cells after treated with taipaienoside A for 6,12 or 24h, accompanied with Pro-caspase8 and Pro - caspase3 decline, cleaved caspase3 peaking at 12h, Bel -2 expressing no significant difference, Bax undetectable in western blot assays. Conclusion Taipaienoside A possesses potent ability of inducing U87 cells apoptosis, and the mechanisms was at least involved by Fas/FasL-associated cascade-dependent apoptotic mechanisms.

  16. 一测多评法测定假马齿苋中间体中的5种三萜皂苷类成分含量%Simultaneous determination of five triterpenoid saponins in Bacopa monnieri extract by quantitative analysis of multi-components with a single marker

    Institute of Scientific and Technical Information of China (English)

    崔雨晴; 张继全; 吴飞; 阮克锋

    2016-01-01

    目的 利用一测多评法建立假马齿苋中间体中5种三萜皂苷类成分的高效液相色谱分析方法.方法 以Bacopaside Ⅰ为内参物,建立Bacoside A3、BacopasideⅡ、Bacopasaponin C isomer、Bacopasaponin C的相对校正因子,从而计算各成分含量,并将一测多评结果与外标法实测值用相对误差评价,验证一测多评法的准确性.结果 Bacopaside Ⅰ与Bacoside A3、BacopasideⅡ、BacopasaponinC isomer、Bacopasaponin C的相对校正因子分别为0.980、0.747、1.046、0.836,一测多评法计算结果与外标法无显著差异,相对误差小于5%.结论 该方法准确可靠,简便可行,可作为假马齿苋中间体多指标成分测定质量控制方法.

  17. Triterpenoid acids from sporophore of Ganoderma lucidum and their inhibition on proliferatin of SKBR3 human breast cancer cells%赤芝子实体中三萜酸类成分及其抗人乳腺癌SKBR3细胞增殖活性

    Institute of Scientific and Technical Information of China (English)

    董虹玲; 赵娜夏; 商倩; 夏广萍; 白秀秀; 邵泽艳; 韩英梅

    2013-01-01

    目的 研究赤芝Ganoderma lucidum子实体中三萜酸类成分及其抗肿瘤活性.方法 用硅胶柱色谱、反相ODS柱色谱、反相HPLC等方法分离得到13个化合物,利用波谱学方法鉴定它们的化学结构,并进一步确定各化合物对乳腺癌SKBR3细胞的生物活性.结果 分离得到13个三萜酸类的化合物,分别鉴定为灵芝烯酸C(1)、灵芝酸C2 (2)、灵赤酸A(3)、灵芝酸G(4)、灵芝烯酸B(5)、灵芝酸B(6)、灵芝酸H(7)、灵芝烯酸A(8)、灵芝酸Ⅰ(9)、灵芝酸A (10)、灵芝烯酸K (11)、灵芝烯酸D(12)、灵芝酸D(13).化合物6在20 μmol/L浓度下对人乳腺癌细胞SK-BR-3的抑制率为40.3%.结论 化合物11是首次从该植物中分离得到的,化合物6对人乳腺癌细胞SK-BR-3显示了一定的抑制活性,其他化合物在该浓度下未显示活性.

  18. Protective effects of triterpenoids from vitis viniferal L. on immunological liver injury in vitro%琐琐葡萄三萜类成分在体外对大鼠免疫性肝损伤的保护作用

    Institute of Scientific and Technical Information of China (English)

    刘涛; 马龙; 赵军; 马琪; 姬风彩; 李涛; 丁玉松; 苏德奇

    2007-01-01

    目的:观察琐琐葡萄三萜类成分总三萜(VTT)和齐墩果酸(OA)在体外对大鼠免疫性肝损伤的保护作用,为阐明维药琐琐葡萄抗病毒作用的物质基础及其可能的作用机制提供理论依据,也为充分利用新疆葡萄的资源优势开发出安全、价廉、有效的抗病毒民族新药奠定基础.方法:Sprague-Dawley (SD)雄性大鼠6只,随机分为正常组与模型组,模型组采用卡介苗(BCG)整体致敏,脂多糖(LPS)离体攻击法建立大鼠原代肝细胞免疫损伤模型,模型组肝细胞分别加入DMEM培养液配制的200 μg/ml二甲基亚砜溶液(DMSO),5、10、20 μg/ml联苯双酯(DDB)溶液,5、20、80 μg/ml VTT溶液或OA溶液,测定并比较不同培养时间(3、6、12、24 h)各组肝细胞培养上清液中谷丙转氨酶(ALT)、谷草转氨酶(AST)的活性和一氧化氮(NO)的含量.结果:正常大鼠肝细胞上清ALT、AST和NO基本未见改变,BCG+LPS损伤后大鼠肝细胞上清ALT、AST和NO在6、12和24 h较正常大鼠明显升高(P<0.01),而VTT和OA (5、20、80 μg/ml)均可程度不同地使升高的ALT、AST和NO明显下降(P<0.01).琐琐葡萄三萜类成分VTT和OA的以上作用与阳性对照药物DDB相似.结论:琐琐葡萄三萜类成分VTT和OA在体外对大鼠免疫性肝损伤具有明显的保护作用.

  19. Avaliação da atividade larvicida de saponinas triterpênicas isoladas de Pentaclethra macroloba (Willd. Kuntze (Fabaceae e Cordia piauhiensis Fresen (Boraginaceae sobre Aedes aegypti Evaluation of larvicidal activity of triterpenoid saponins isolated of Pentaclethra macroloba (Willd. Kuntze (Fabaceae and Cordia piauhiensis Fresen (Boraginaceae against Aedes aegypti

    Directory of Open Access Journals (Sweden)

    G.M.P. Santiago

    2005-09-01

    Full Text Available A atividade larvicida de quatro saponinas monodesmosídicas (1-4 isoladas de Pentaclethra macroloba e de uma saponina bidesmosídica (5 isolada de Cordia piauhiensis foi avaliada sobre larvas de estágio 3 de Aedes aegypti. As larvas foram expostas a várias concentrações (500, 250, 100, 50, 25 e 12,5 mg/mL das saponinas por um período de 24 h. Os resultados indicam que somente as saponinas 1-3 mostraram alta atividade larvicida, com CL50 variando de 18,6 a 27,9 mg/mL. Estes resultados ressaltam as potencialidades destas saponinas como possíveis agentes larvicidas naturais.The larvicidal activity of the four monodesmoside saponins (1-4 isolated from Pentaclethra macroloba and one bidesmoside saponin (5 from Cordia piauhiensis was evaluated on 3rd instar larvae of Aedes aegypti. The larvae were exposed to serial concentrations (500, 250, 100, 50, 25 and 12.5 mg/mL saponins for a period of 24 h. The results indicate that, only the saponins 1-3 showed high larvicidal activity, with LC50 ranging of 18,6-27,9 mg/mL. These results suggest that these can be used as natural larvicidal agents.

  20. Non-Saponifiable Lipid Composition of Four Salt-Secretor and Non-Secretor Mangrove Species from North Sumatra, Indonesia

    Directory of Open Access Journals (Sweden)

    Julayha

    2012-08-01

    Full Text Available Non-saponifiable lipid (NSL of the fresh leaves and roots from two salt-secretor mangrove species, namely Aegiceras corniculatum (L. Blanco and Avicennia alba Bl. and two non-secretor mangroves, i.e. Acrostichum aureum L. and Excoecaria agallocha L. was analyzed with special emphasize to triterpenoids and phytosterols. Identification of the triterpenoids and phytosterols was confirmed by comparison of their retention time on the GC column with those of authentic standards and on the interpretation of GC-MS spectra. Triterpenoids and phytosterols comprised the major proportion of NSL. The triterpenoids and phytosterols mainly consisted of 7 and 4 compounds. Triterpenoids were the largest constituent of Ac. aureum and Ae. corniculatum leaves and roots, and E. agallocha roots. In contrast to these triterpenoids-rich species, phytosterols were relatively dominant in the roots of Av. alba. The species of Av. alba and E. agallocha in the leaves were distinguished from the others in that both species contained a larger quantity of phytol. Ae. corniculatum contained a large amount of betulin and α-amyrin in the roots, as well as lupeol in the roots of Av. alba. The diversity in the NSL composition noted with mangrove species in both the leaves and roots suggested that NSL of mangrove leaves and roots can be used as chemotaxonomical character to differentiate species.

  1. Field evaluation of in vitro-induced tetraploid and diploid Centella asiatica (L.) Urban.

    Science.gov (United States)

    Thong-On, Wachiraporn; Arimatsu, Panida; Pitiporn, Supaporn; Soonthornchareonnon, Noppamas; Prathanturarug, Sompop

    2014-04-01

    Centella asiatica-a medicinal plant that produces high-value active triterpenoids-is in increasing demand by the pharmaceutical and cosmetic industries. The aim of this study was to field-test one induced tetraploid and three diploid C. asiatica lines for the selection of high-quality plants with high phytomass and triterpenoid content and to determine their optimal harvesting time. All tested C. asiatica were micropropagated using an established protocol. One-month-old plantlets were acclimatized for the field experiment. The plants were grown in a randomized complete block design (RCBD) with three replications, ten plantlets per replication, and the experimental bed site was 0.6 × 1.0 m. Growth parameters, phytomass and the amounts of four active triterpenoids were evaluated. All lines exhibited the highest growth, yields and triterpenoids at 4 months after cultivation. The tetraploid line showed significantly better characteristics, i.e., larger leaf area, leaf width, petiole length, and greater yields, than diploid lines. Dry weight per cultivated area (77.53 ± 3.07 g/m(2)) and total triterpenoids (15.38 ± 0.76 % dry weight) were increased significantly in tetraploid plants of C. asiatica. Furthermore, the harvesting time had an effect on the yield and triterpenoid content (P tetraploid and diploid lines, the yields and triterpenoid content per cultivated area reached their maximum at 4 months after planting. Our results demonstrated that polyploidy induction is a beneficial tool that can be used to improve the medicinal value of C. asiatica.

  2. 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)

  3. Plant-derived terpenoids as paleovegetation proxies: evaluation of the proxy with Paleocene and Eocene megafloras and plant biomarkers in the Bighorn Basin, USA

    Science.gov (United States)

    Diefendorf, A. F.; Freeman, K. H.; Wing, S. L.

    2012-12-01

    Plant terpenoids (defense compounds synthesized from the 5-carbon building block isoprene) have a long history of use as geochemical plant biomarkers, and potentially can be used to reconstruct changes in the abundances of major land plant groups in rocks and sediments that do not preserve plant megafossils or pollen. Pentacyclic triterpenoids are synthesized almost exclusively by angiosperms whereas conifers produce the tricyclic diterpenoids. Many previous studies have focused on the use of di- to triterpenoid ratios to reconstruct floral changes in the geologic past, however few studies have compared terpenoid-based paleoflora proxies to pollen or megafossils. Prior reconstructions also did not take into account differences in biomarker production between plant functional types, such as deciduous and evergreen plants, which can be quite large. To investigate the use of terpenoids as paleoflora proxies, we examined sediments from the Bighorn Basin (Wyoming, USA) where ancient megafloras have been studied in detail. We analyzed di- and triterpenoid abundances as well as plant leaf waxes (n-alkanes) and other biomarkers in a total of 75 samples from 15 stratigraphic horizons from the late Paleocene (62 Ma) to early Eocene (52.5 Ma). By comparing terpenoid ratios with abundances estimated from plant megafossils, we can evaluate the utility of terpenoids as paleovegetation proxies. In nearly all samples, angiosperm triterpenoids are significantly lower in abundance than conifer diterpenoids. This contrasts with leaf fossil data that indicate paleofloras were dominated by angiosperms in both abundance and diversity. Traditional use of terpenoid paleovegetation proxies would therefore significantly overestimate the abundance of conifers, even when accounting for plant production differences. To determine if this overestimate is related to the loss of angiosperm triterpenoids (rather than enhanced production of diterpenoids in the geologic past), we compared angiosperm

  4. Inhibition of pro-inflammatory mediators: role of Bacopa monniera (L.) Wettst.

    Science.gov (United States)

    Viji, Vijayan; Helen, Antony

    2011-10-01

    Bacopa monniera (L.) Wettst is a renowned plant in the Ayurvedic system of medicine. The present study seeks to identify the anti-inflammatory activity of two fractions from the methanolic extract of Bacopa, viz. the triterpenoid and bacoside-enriched fractions. The ability of these two fractions to inhibit the production of pro-inflammatory cytokines such as tumor necrosis factor-α (TNF-α) and interleukin-6 was tested using lipopolysaccharide (LPS)-activated peripheral blood mononuclear cells and peritoneal exudate cells in vitro. We found that triterpenoid and bacoside-enriched fractions significantly inhibited LPS-activated TNF-α, IL-6 and nitrite production in mononuclear cells. Significant antioxidant activity was exhibited by the bacoside enriched fraction compared to the triterpenoid fraction. Carrageenan-induced hind paw oedema assay revealed that triterpenoid and bacoside-enriched fractions exerted anti-oedematogenic effect, while in the arthritis model only the triterpenoid fraction exerted an anti-arthritic potential. The present study provides an insight into the ability of Bacopa monniera to inhibit inflammation through modulation of pro-inflammatory mediator release.

  5. 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.

  6. A New Cytotoxic Friedelane Acid – Pluricostatic Acid – and Other Compounds from the Leaves of Marila pluricostata

    Directory of Open Access Journals (Sweden)

    Mahabir P. Gupta

    2008-11-01

    Full Text Available Bioassay-guided fractionation of the dichloromethane extract of the leaves of Marila pluricostata led to the isolation of 2α,3β-dihydroxy-D:A-friedoolean-28-oic acid (pluricostatic acid, a new friedelane triterpenoid, (1, ten known triterpenoids and three sterols. Their chemical structures were elucidated through spectroscopic analysis. The less polar fractions, on GC/MS analysis and comparison with a MS library, resulted in the identification of twenty four sesquiterpenoids. The new triterpenoid acid 1 showed cytotoxicity against the MCF-7, H-460, and SF-268 human cancer cell lines with GI50 values from 1.2 to 3.3 μg/mL.

  7. Anti-inflammatory Terpenoids from the Leaves and Twigs of Dysoxylum gotadhora.

    Science.gov (United States)

    Jiang, Kan; Chen, Lu-Lin; Wang, Shu-Fang; Wang, Yi; Li, Ya; Gao, Kun

    2015-05-22

    Nine new terpenoids (1-3, 5-10), including three cyclolanostane triterpenoids (1-3) and six isopimarane diterpenoids (5-10), along with six known terpenoids (4, 11-15), were isolated from the leaves and twigs of Dysoxylum gotadhora. Compound 1 represents a class of rare natural 21,24-epoxy cyclolanostane-type triterpenoids, and compounds 2 and 3 are the first examples of 21,25-epoxy cyclolanostane-type triterpenoids. Compounds 1, 2, 4, 8, and 15 exhibited noteworthy inhibition of nitric oxide production induced by lipopolysaccharide in RAW 264.7 cells with IC50 values of 25.5, 41.5, 27.4, 14.5, and 45.2 μM, respectively.

  8. 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.

  9. Origin of the Tertiary reservoired hydrocarbons along the central Texas and Louisiana Gulf Coast rim

    Energy Technology Data Exchange (ETDEWEB)

    Cole, G.A.; Sassen, R. (BP Exploration, Inc., Houston, TX (USA)); Chinn, E.W. (Louisiana State Univ., Baton Rouge (USA)); Piggott, N.; Gibbons, M.J.

    1990-05-01

    Tertiary reservoired hydrocarbons along the central Texas and Louisiana Gulf Coast rim were most likely derived from Paleocene/Eocene Wilcox Group and Sparta Formation marine shales. Sixteen total soluble extracts and >200 oil samples were analyzed using carbon isotopic techniques ({delta}{sup 13}C) and gas chromatography-mass spectometry (GC-MS). Results demonstrated that interpretations must use all types of data because Cretaceous derived and Tertiary derived oils overlap in southern Louisiana. When isotopic, sterane, hopane, and light hydrocarbon data are combined separation of classes become possible. Cretaceous oils and extracts have a full range of extended hopanes, a characteristic peak eluting immediately after C{sub 30} hopane and no oleanane. Paleogene oils and extracts have oleanane and a restricted range of extended hopanes. Regional trends indicate that eastern Louisiana oils were derived from the Sparta or a Sparta/Wilcox mix, the Mississippi delta oils from a Cretaceous clastic source, and western Louisiana and Texas oils from the Wilcox source. Regional variations in GOR/CGR are a function of timing and mechanism of migration.

  10. Antidiabetic potential and secondary metabolites screening of mangrove gastropod Cerithidea obtusa

    Institute of Scientific and Technical Information of China (English)

    Reni Tri Cahyani; Sri Purwaningsih; Azrifitria

    2015-01-01

    Objective: To study the possible effects of Cerithidea obtusa extract as antidiabetic and to screen the secondary metabolites presence. Methods: Antidiabetic activity of Cerithidea obtusa extract was measured in vitro usingα-glucosidase inhibition method. Whereas, secondary metabolites screening was measured qualitatively. Results: The methanol extract had antidiabetic activity (IC50 = 36.40 mg/mL). However, the control drug acarbose had significantly higher antidiabetic activity (IC50 = 0.32 mg/mL). Secondary metabolites screening showed the presence of alkaloids, flavonoids, triterpenoids and saponins. Conclusions: The methanol extract had antidiabetic activity and the presence of alkaloids, flavonoids and triterpenoids might contribute to the activity.

  11. Methyl jasmonate mediates upregulation of bacoside A production in shoot cultures of Bacopa monnieri.

    Science.gov (United States)

    Sharma, Poojadevi; Yadav, Sheetal; Srivastava, Anshu; Shrivastava, Neeta

    2013-07-01

    Methyl jasmonate (MJ) enhances the production of a range of secondary metabolites including triterpenoid saponins in a variety of plant species. Here, it enhanced production of bacoside A, a valuable triterpenoid saponin having nootropic therapeutic activity in in vitro shoot cultures of Bacopa monnieri, the only known source of bacoside A. The highest yield was with 50 μM MJ giving 4.4 mg bacoside A/g dry wt; an 1.8-fold increase (compared to control) after 1 week.

  12. Saponins from Chinese Medicines as Anticancer Agents

    Directory of Open Access Journals (Sweden)

    Xiao-Huang Xu

    2016-10-01

    Full Text Available Saponins are glycosides with triterpenoid or spirostane aglycones that demonstrate various pharmacological effects against mammalian diseases. To promote the research and development of anticancer agents from saponins, this review focuses on the anticancer properties of several typical naturally derived triterpenoid saponins (ginsenosides and saikosaponins and steroid saponins (dioscin, polyphyllin, and timosaponin isolated from Chinese medicines. These saponins exhibit in vitro and in vivo anticancer effects, such as anti-proliferation, anti-metastasis, anti-angiogenesis, anti-multidrug resistance, and autophagy regulation actions. In addition, related signaling pathways and target proteins involved in the anticancer effects of saponins are also summarized in this work.

  13. 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....../L and total triterpenoid concentrations of 854 mg/L, the highest concentrations reported so far. Purification of lupane-type triterpenoids with high selectivity and yield was achieved by solid-liquid extraction without prior cell disruption using polar aprotic solvents such as acetone or ethyl acetate...

  14. CONSTITUENTS FROM LIMONIA CRENULATA

    Institute of Scientific and Technical Information of China (English)

    XUE-MEI NIU; SHENG-HONG LI; LI-YAN PENG; ZHONG-WEN LIN; GAO-XIONG RAO; HAN-DONG SUN

    2001-01-01

    A new indole alkaloid, crenulatine (1), along with twenty known compounds, was isolated from the stems of Lirnonia Crenulata. Their structures were identified by spectral means. Those compounds include four alkaloids, four coumarins, two flavanones, three tetranortriterpenoids,one triterpenoid, three steroids, two lignans and two aromatic compounds.

  15. 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 gene

  16. 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.

  17. 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

  18. Saponins, classification and occurrence in the plant kingdom

    NARCIS (Netherlands)

    Vincken, J.P.; Heng, L.; Groot, de Æ.; Gruppen, H.

    2007-01-01

    Saponins are a structurally diverse class of compounds occurring in many plant species, which are characterized by a skeleton derived of the 30-carbon precursor oxidosqualene to which glycosyl residues are attached. Traditionally, they are subdivided into triterpenoid and steroid glycosides, or into

  19. A cytotoxic saponin from Albizia julibrissin.

    Science.gov (United States)

    Zou, Kun; Zhao, Yu-Ying; Zhang, Ru-Yi

    2006-08-01

    A new triterpenoidal saponin (1: Julibroside J(21)) with a xylopyranosyl moiety located at its C-21 side chain was isolated from Albizia julibrissin DURAZZ. (Leguminosae), and its structure was determined on the basis of comprehensive spectroscopic analyses. Compound 1 showed marked inhibitory action against Bel-7402 cancer cell line at 10 microg/ml.

  20. An antitumor compound julibroside J28 from Albizia julibrissin.

    Science.gov (United States)

    Liang, Hong; Tong, Wen-yong; Zhao, Yu-ying; Cui, Jing-rong; Tu, Guang-zhong

    2005-10-15

    A new triterpenoid saponin, julibroside J(28) (1), was isolated from the stem bark of Albizia julibrissin Durazz (Leguminosae) by using chromatographic method. The structure of 1 was established by spectroscopic methods. 1 displayed significant antitumor activity in vitro against PC-3M-1E8, Bel-7402, and HeLa cancer cell lines at 10 microM assayed by SRB method.

  1. Diastereoisomeric saponins from Albizia julibrissin.

    Science.gov (United States)

    Zou, Kun; Tong, Wen-yong; Liang, Hong; Cui, Jing-rong; Tu, Guang-zhong; Zhao, Yu-ying; Zhang, Ru-yi

    2005-05-23

    The structures of four new diastereoisomeric triterpenoidal saponins Julibroside J5, J8, J12 and J13 (1-4) isolated from Albizia julibrissin Durazz. (Leguminosae) have been determined on the basis of comprehensive spectroscopic analysis and chemical degradation. Julibroside, J8 and J13 showed marked cytotoxic activities against Bel-7402 cancer cell line at 100 microg/mL.

  2. 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)

  3. Antitubercular Lanostane Triterpenes from Cultures of the Basidiomycete Ganoderma sp. BCC 16642.

    Science.gov (United States)

    Isaka, Masahiko; Chinthanom, Panida; Sappan, Malipan; Danwisetkanjana, Kannawat; Boonpratuang, Thitiya; Choeyklin, Rattaket

    2016-01-22

    Sixteen new lanostane triterpenoids (1-16), together with 26 known compounds (17-42), were isolated from cultures of the basidiomycete Ganoderma sp. BCC 16642. Antitubercular activities of these Ganoderma lanostanoids against Mycobacterium tuberculosis H37Ra were evaluated, and structure-activity relationships are proposed.

  4. Environ: E00205 [KEGG MEDICUS

    Lifescience Database Archive (English)

    Full Text Available noid [CPD:C06085], Friedelin [CPD:C08626], Shionone, Triterpenoid saponin, Astersaponin, Quercetin [CPD:C00389], Prosapo...genin, epi-Friedelanol [CPD:C17123], Lachnophyllol [CPD:C17965], Anethole [CPD:C10428], Lachnophyllol acetate, Astersapo

  5. Drug: D09138 [KEGG MEDICUS

    Lifescience Database Archive (English)

    Full Text Available rpenoid [CPD:C06085], Friedelin [CPD:C08626], Shionone, Triterpenoid saponin, Astersaponin, Quercetin [CPD:C00389], Prosapo...genin, epi-Friedelanol [CPD:C17123], Lachnophyllol [CPD:C17965], Anethole [CPD:C10428], Lachn...ophyllol acetate, Astersaponin, Essential oil Aster tataricus [TAX:588669] Same a

  6. Drug: D10236 [KEGG MEDICUS

    Lifescience Database Archive (English)

    Full Text Available D10236 Crude, Drug Melia fruit (non-JP); Meliae fructus Modified triterpenoid, Toosenda...nin, Tannin, Organic acid, Malic acid [CPD:C00711] Melia toosendan [TAX:71608], Melia azedarach [TAX:155...640 Same as: E00317 Meliaceae (mahogany family) Melia toosendan, Melia azedarach fruit; Standards for non-ph

  7. Environ: E00317 [KEGG MEDICUS

    Lifescience Database Archive (English)

    Full Text Available E00317 Melia fruit (non-JP) Meliae fructus Crude drug Modified triterpenoid, Toosenda...nin, Tannin, Organic acid, Malic acid [CPD:C00711] Melia toosendan [TAX:71608], Melia azedarach [TAX:155640] Same as: D10236 Meliaceae (mahogany family) Chinaberry fruit ...

  8. Saponins, classification and occurrence in the plant kingdom

    NARCIS (Netherlands)

    Vincken, J.P.; Heng, L.; Groot, de Æ.; Gruppen, H.

    2007-01-01

    Saponins are a structurally diverse class of compounds occurring in many plant species, which are characterized by a skeleton derived of the 30-carbon precursor oxidosqualene to which glycosyl residues are attached. Traditionally, they are subdivided into triterpenoid and steroid glycosides, or into

  9. Guayule resin detection and influence on guayule rubber

    Science.gov (United States)

    Guayule (Parthenium argentatum) is a natural rubber (cis-1,4-polyisoprene) producing crop, native to North America. Guayule also produces organic resins, complex mixtures of terpenes, triglycerides, guayulins, triterpenoids and other components. During natural rubber extraction, guayule resins can b...

  10. 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

  11. Cytostatic activity of some compounds from the unsaponifiable fraction obtained from virgin olive oil.

    Science.gov (United States)

    Saenz, M T; Garcia, M D; Ahumada, M C; Ruiz, V

    1998-06-30

    Oleuropein, tyrosol, squalene and the fraction of sterols and triterpenoid dialcohols from the unsaponifiable fraction obtained from virgin olive oil have been tested for possible cytostatic activity against McCoy cells, using 6-mercaptopurine as a positive control. The samples of sterols and triterpenic dialcohols showed a strong activity.

  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. New Cytotoxic Saponins from Lysimachia davurica Ledeb.

    Institute of Scientific and Technical Information of China (English)

    2006-01-01

    To investigate the saponins from whole plants of Lysimachia davurica Ledeb., two new saponins named davuricoside I (compound 1) and E (compound 2) were isolated. Their chemical structures were elucidated as 3β,16α, 28, 29-tetrihydroxy-olean-12-en-3-O-β-D-glucopyranosyl-(1-→2)-β-D-glucuronopyranoside (compound 1)and 3β,16α, 29-trihydroxy-13, 28-epoxy-oleanane-3-O-β-D-glucopyranosyl-(1→2)-β-D-glucuronopyranoside (compound 2) on the basis of their one- and two-dimensional nuclear magnetic resonance and mass spectrometry data, and chemical methods. Compound 1 showed significant cytotoxic activity against human A2780 cells.

  14. The bioguided fractionation and pharmacological activity of an endemic Salix canariensis species

    Directory of Open Access Journals (Sweden)

    Gutiérrez Sandra Dévora

    2017-06-01

    Full Text Available The present study was designed to confirm the wide traditional use of treating pain with Salix canariensis, an endemic species of the Macaronesian region. The active compounds were identified. Pharmacological activities were explored in experimental animals by acetic acid-induced writhing, formalin and Levy’s tests, and bioactive compounds were identified after a bio-guided fractionation of the most active organic extract. S. canariensis extract, orally administrated at different doses, led to a significant reduction in writhing, caused a moderate decrease of formalin-induced pain and revealed an excellent dose-dependent anti-inflammatory effect. Bioassay-guided fractionation of the ethyl acetate extract suggested the possible presence of pentacyclic triterpenes from oleanane and ursane series. These findings allow the conclusion that S. canariensis exerts analgesic and anti-inflammatory activities, documenting its traditional use in the treatment of pain and inflammatory diseases.

  15. Oleanene Glycosides from the Leaves of Acanthopanax seiboldianus forma albeofolium Yook%异柱五加叶中齐墩果烷型皂苷的研究

    Institute of Scientific and Technical Information of China (English)

    刘向前; 金寅钐; 陆昌洙; 南相吉; 李龙燮

    2008-01-01

    Four known oleanane glycosides were isolated for the first time from the MeOH extract of the leaves of Acanthopanax sieboldianus forma albeofolium Yook by using column chromatography.They were identified as kalopanax-saponin B (1),acanthopanax saponin CP3 (2),kalopanax-saponin A (3) and sieboldianoside A (4) on the basis of physicochemical and spectroscopic data (1H NMR,13C NMR,2D NMR and FAB-MS).%利用柱色谱从异柱五加 (Acanthopanax sieboldianus forma albeofolium Yook) 叶的甲醇提取液中分离出四个齐墩果烷型皂苷类化合物.通过波谱方法(1H NMR、13C NMR、2D NMR和FAB-MS)鉴定它们分别为kalopanax-saponin B (1)、acanthopanax saponin CP3(2)、kalopanax-saponin A (3) 和sieboldianoside A (4).

  16. Pentacyclic triterpene distribution in various plants - rich sources for a new group of multi-potent plant extracts.

    Science.gov (United States)

    Jäger, Sebastian; Trojan, Holger; Kopp, Thomas; Laszczyk, Melanie N; Scheffler, Armin

    2009-06-04

    Pentacyclic triterpenes are secondary plant metabolites widespread in fruit peel, leaves and stem bark. In particular the lupane-, oleanane-, and ursane triterpenes display various pharmacological effects while being devoid of prominent toxicity. Therefore, these triterpenes are promising leading compounds for the development of new multi-targeting bioactive agents. Screening of 39 plant materials identified triterpene rich (> 0.1% dry matter) plant parts. Plant materials with high triterpene concentrations were then used to obtain dry extracts by accelerated solvent extraction resulting in a triterpene content of 50 - 90%. Depending on the plant material, betulin (birch bark), betulinic acid (plane bark), oleanolic acid (olive leaves, olive pomace, mistletoe sprouts, clove flowers), ursolic acid (apple pomace) or an equal mixture of the three triterpene acids (rosemary leaves) are the main components of these dry extracts. They are quantitatively characterised plant extracts supplying a high concentration of actives and therefore can be used for development of phytopharmaceutical formulations.

  17. Pentacyclic Triterpene Distribution in Various Plants – Rich Sources for a New Group of Multi-Potent Plant Extracts

    Directory of Open Access Journals (Sweden)

    Armin Scheffler

    2009-06-01

    Full Text Available Pentacyclic triterpenes are secondary plant metabolites widespread in fruit peel, leaves and stem bark. In particular the lupane-, oleanane-, and ursane triterpenes display various pharmacological effects while being devoid of prominent toxicity. Therefore, these triterpenes are promising leading compounds for the development of new multi-targeting bioactive agents. Screening of 39 plant materials identified triterpene rich (> 0.1% dry matter plant parts. Plant materials with high triterpene concentrations were then used to obtain dry extracts by accelerated solvent extraction resulting in a triterpene content of 50 - 90%. Depending on the plant material, betulin (birch bark, betulinic acid (plane bark, oleanolic acid (olive leaves, olive pomace, mistletoe sprouts, clove flowers, ursolic acid (apple pomace or an equal mixture of the three triterpene acids (rosemary leaves are the main components of these dry extracts. They are quantitatively characterised plant extracts supplying a high concentration of actives and therefore can be used for development of phytopharmaceutical formulations.

  18. Antisweet saponins from Gymnema sylvestre.

    Science.gov (United States)

    Ye, W; Liu, X; Zhang, Q; Che, C T; Zhao, S

    2001-02-01

    Three new oleanane-type triterpene glycosides (1-3), along with the sodium salt of alternoside II (4), were isolated from an ethanol extract of the leaves of Gymnema sylvestre. The structures of these new saponins were identified as 21 beta-O-benzoylsitakisogenin 3-O-beta-D-glucopyranosyl(1-->3)-beta-D-glucuronopyranoside (1), the potassium salt of longispinogenin 3-O-beta-D-glucopyranosyl(1-->3)-beta-D-glucuronopyranoside (2), and the potassium salt of 29-hydroxylongispinogenin 3-O-beta-D-glucopyranosyl(1-->3)-beta-D-glucuronopyranoside (3). The aglycon of 3, gymnemagenol (3a), was characterized as 3 beta,16 beta,28, 29-tetrahydroxyolean-12-ene. Structure elucidation was accomplished by interpretation of NMR (DQF-COSY, HMQC, and HMBC) results, FABMS, and hydrolysis. Saponin 1 and the sodium salt of alternoside II (4) exhibited antisweet activity.

  19. 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.

  20. Anti-inflammatory triterpenes from Pistacia terebinthus galls.

    Science.gov (United States)

    Giner-Larza, Eva M; Máñez, Salvador; Giner, Rosa M; Recio, M Carmen; Prieto, José M; Cerdá-Nicolás, Miguel; Ríos, José Luis

    2002-04-01

    From the galls of Pistacia terebinthus we obtained an extract that proved to be effective against chronic and acute inflammation. Now we report on the isolation and identification of three triterpenes: two tirucallane-type lanostanoids and one oleanane, which we have identified as masticadienonic acid (1), masticadienolic acid (2), and morolic acid (3), respectively. All of them showed effectiveness on the mouse ear inflammation induced by repeated applications of 12-O-tetradecanoylphorbol 13-acetate and on the phospholipase A2-induced foot paw edema. The pharmacological activity of the compounds was ratified by a histological study of the ear samples. In addition, they inhibited leukotriene B4 production in rat polymorphonuclear leukocytes stimulated with calcium ionophore A 23187.