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Sample records for monotetrahydrofuran annonaceous acetogenins

  1. New cytotoxic monotetrahydrofuran annonaceous acetogenins from Annona muricata.

    Science.gov (United States)

    Liaw, Chih-Chuang; Chang, Fang-Rong; Lin, Chih-Yuan; Chou, Chi-Jung; Chiu, Hui-Fen; Wu, Ming-Jung; Wu, Yang-Chang

    2002-04-01

    Three new monotetrahydrofuran annonaceous acetogenins, muricin H (1), muricin I (2), and cis-annomontacin (3), along with five known acetogenins, annonacin, annonacinone, annomontacin, murisolin, and xylomaticin, were isolated from the seeds of Annona muricata. Additionally, two new monotetrahydrofuran annonaceous acetogenins, cis-corossolone (4) and annocatalin (5), together with four known ones, annonacin, annonacinone, solamin, and corossolone, were isolated from the leaves of this species. The structures of all new isolates were elucidated and characterized by spectral and chemical methods. These new acetogenins exhibited significant activity in in vitro cytotoxic assays against two human hepatoma cell lines, Hep G(2) and 2,2,15. Compound 5 showed a high selectivity toward the Hep 2,2,15 cell line.

  2. Muricatocins A and B, two new bioactive monotetrahydrofuran Annonaceous acetogenins from the leaves of Annona muricata.

    Science.gov (United States)

    Wu, F E; Zeng, L; Gu, Z M; Zhao, G X; Zhang, Y; Schwedler, J T; McLaughlin, J L; Sastrodihardjo, S

    1995-06-01

    The leaves of Annona muricata have yielded the novel monotetrahydrofuran Annonaceous acetogenins, muricatocins A [1] and B [2]. Each compound possesses five hydroxyl groups, with two hydroxyl groups at the C-10 and C-12 positions. The absolute configurations of 1 and 2 (except for positions C-10 and C-12) were determined by Mosher ester methodology. The C-10, C-12 acetonides (1c, 2c) suggested relative stereochemistry and significantly enhanced cytotoxicity against the A-549 human lung tumor cell line. Three known monotetrahydrofuran acetogenins, annonacin A, (2,4-trans)-isoannonacin, and (2,4-cis)-isoannonacin, were also found.

  3. Two new cytotoxic monotetrahydrofuran Annonaceous acetogenins, annomuricins A and B, from the leaves of Annona muricata.

    Science.gov (United States)

    Wu, F E; Gu, Z M; Zeng, L; Zhao, G X; Zhang, Y; McLaughlin, J L; Sastrodihardjo, S

    1995-06-01

    The leaves of Annona muricata have yielded eight monotetrahydrofuran Annonaceous acetogenins. Two of them, annomuricins A [1] and B [2], whose chemical structures were deduced by ms, nmr, ir, and uv spectral and chemical methods, are novel and unusual. Compounds 1 and 2 each possess five hydroxyl groups; two hydroxyl groups are vicinal, with the vicinal group of 1 threo and that of 2 erythro. The absolute configurations of 1 and 2 were determined by Mosher ester methodology. Six monotetrahydrofuran acetogenins, previously described in the seeds, were found in the leaves; these are gigantetrocin A, annonacin-10-one, muricatetrocins A and B, annonacin, and goniothalamicin.

  4. New bioactive monotetrahydrofuran Annonaceous acetogenins, annomuricin C and muricatocin C, from the leaves of Annona muricata.

    Science.gov (United States)

    Wu, F E; Zeng, L; Gu, Z M; Zhao, G X; Zhang, Y; Schwedler, J T; McLaughlin, J L; Sastrodihardjo, S

    1995-06-01

    The leaves of Annona muricata have yielded two additional monotetrahydrofuran Annonaceous acetogenins, annomuricin C [1] and muricatocin C [2]. Compounds 1 and 2 each possess five hydroxyl groups; two hydroxyl groups are at the C-10/C-11 and C-10/C-12 positions in 1 and 2, respectively. The absolute configurations of 1 and 2, except for positions C-10 and C-11 or C-12, were determined by Mosher ester methodology. The C-10/C-11 and C-10/C-12 acetonides (1c, 2c) suggested relative stereochemistry and significantly enhanced the cytotoxicities against the A-549 human lung and the MCF-7 human beast solid tumor cell lines. One known monotetrahydrofuran acetogenin, gigantetronenin, not described previously from this plant, was also found.

  5. Three new anti-proliferative Annonaceous acetogenins with mono-tetrahydrofuran ring from graviola fruit (Annona muricata).

    Science.gov (United States)

    Sun, Shi; Liu, Jingchun; Kadouh, Hoda; Sun, Xiuxiu; Zhou, Kequan

    2014-06-15

    Bioassay-guided fractionation of the fruit powder of graviola (Annona muricata) yielded three novel compounds: muricins J, K, and L. The compounds are all C35 Annonaceous acetogenins with a mono-tetrahydrofuran ring and four hydroxyls. Their structures were elucidated by spectral methods and chemical modification after isolation via chromatographic techniques and HPLC purification. These three acetogenins demonstrated an antiproliferative against human prostate cancer PC-3 cells.

  6. Novel cytotoxic annonaceous acetogenins from Annona muricata.

    Science.gov (United States)

    Chang, F R; Wu, Y C

    2001-07-01

    Seven new annonaceous acetogenins, muricins A-G (1-7), as well as five known compounds, a mixture of muricatetrocin A (8) and muricatetrocin B (9), longifolicin (10), corossolin (11), and corossolone (12), were isolated from the seeds of Annona muricata. The structures of all isolates were elucidated and characterized by spectral and chemical methods. These acetogenins showed significantly selective in vitro cytotoxicities toward the human hepatoma cell lines Hep G(2) and 2,2,15.

  7. Divergence en Route to Nonclassical Annonaceous Acetogenins

    DEFF Research Database (Denmark)

    Strand, Daniel; Norrby, Per-Ola; Rein, Tobias

    2006-01-01

    Syntheses of the nonclassical annonaceous acetogenins, pyranicin, and pyragonicin from common latestage intermediates are presented. The construction of key elements relies on asymmetric HWE reactions, including the desymmetrization of a meso-dialdehyde and a parallel kinetic resolution of a race...

  8. Two new mono-tetrahydrofuran ring acetogenins, annomuricin E and muricapentocin, from the leaves of Annona muricata.

    Science.gov (United States)

    Kim, G S; Zeng, L; Alali, F; Rogers, L L; Wu, F E; McLaughlin, J L; Sastrodihardjo, S

    1998-04-01

    Bioactivity-directed fractionation of the leaf extract of Annona muricata L. (Annonaceae) has resulted in the isolation of two new Annonaceous acetogenins, annomuricine (1) and muricapentocin (2). Compounds 1 and 2 are monotetrahydrofuran ring acetogenins bearing two flanking hydroxyl groups; however, each has three additional hydroxyl groups. Compound 1 has an erythro 1,2-diol, and 2 has a 1,5,9-triol moiety. Both 1 and 2 showed significant cytotoxicities against six types of human tumors, with selectivities to the pancreatic carcinoma (PACA-2) and colon adenocarcinoma (HT-29) cell lines.

  9. Isolation of three new annonaceous acetogenins from Graviola fruit (Annona muricata) and their anti-proliferation on human prostate cancer cell PC-3.

    Science.gov (United States)

    Sun, Shi; Liu, Jingchun; Zhou, Ninghui; Zhu, Wenjun; Dou, Q Ping; Zhou, Kequan

    2016-09-01

    Bioassay-guided fractionation of the fruit powder of Graviola (Annona muricata) was continued to be conducted and yielded three more novel bioactive compounds: C-35 annonaceous acetogenins, muricins M and N, and C-37 annonaceous acetogenins, muricenin. They all contain a mono-tetrahydrofuran ring and four hydroxyl groups. The structures were elucidated by spectral methods and chemical modification after isolation via open column chromatographic separation and HPLC purification. Especially, murices M and N demonstrated more potent anti-proliferative activities against human prostate cancer PC-3 cells.

  10. New adjacent Bis-tetrahydrofuran Annonaceous acetogenins from Annona muricata.

    Science.gov (United States)

    Chang, Fang-Rong; Liaw, Chih-Chuang; Lin, Chih-Yuan; Chou, Chi-Jung; Chiu, Hui-Fen; Wu, Yang-Chang

    2003-03-01

    Bioactivity-guided fractionation led to the isolation of two new Annonaceous acetogenins, annocatacin A ( 1). and annocatacin B ( 2). from the seeds and the leaves, respectively, of Annona muricata. Compounds 1 and 2 are the first examples where the adjacent bis-tetrahydrofuran ring system is located at C-15. The new structures were elucidated and characterized by spectral and chemical methods. Both Annonaceous acetogenins 1 and 2 showed significant in vitro cytotoxicity toward the human hepatoma cell lines, Hep G2 and 2,2,15, and were compared with the known adjacent bis-tetrahydrofuran acetogenins, neoannonin ( 3). desacetyluvaricin ( 4). bullatacin ( 5). asimicin ( 6). annoglaucin ( 7). squamocin ( 8). and rollimusin ( 9).

  11. Apolar Annonaceous acetogenins from the fruit pulp of Annona muricata.

    Science.gov (United States)

    Melot, Alice; Fall, Djibril; Gleye, Christophe; Champy, Pierre

    2009-11-02

    A methylene chloride extract of the pulp of Annona muricata L. was fractionated in search for scarcely functionalized Annonaceous acetogenins (type E). Previously known C-35 and C-37 mono-epoxy unsaturated compounds, epomuricenins-A and -B (1+2) and epomusenins-A and -B (3+4), were obtained. Two new mono-epoxy saturated C-35 representatives, epomurinins-A and -B (5+6) were also isolated.

  12. Chemical Biology Studies on Molecular Diversity of Annonaceous Acetogenins

    Institute of Scientific and Technical Information of China (English)

    Yao Zhu-Jun

    2004-01-01

    Annonaceous acetogenins, isolated from the Annonaceae plants, have been attracting worldwide attention in recent years due to their biological activities, especially as growth inhibitors of certain tumor ceils [ 1 ]. They have been shown to function by blocking complex I in mitochondria [2] as well as ubiquinone-linked NADPH oxidase in the cells of specific tumor cell lines, including some multidrug-resistant ones [3]. These features make these acetogenins excellent leads for the new antitumor agents. In our previous work, the compounds 1a to 1d (Figure 1), which relies on structure simplification while maintaining all essential functionalities of the acetogenins, was in vitro tested against several human solid tumor cell lines and showed interesting cell selectivity [4]. All four analogues show remarkable activity against the HCT-8 and HT-29 cell lines, while compound 1c was found the best [4bi. In order to further investigate the effects of key structural features, a convergent parallel fragments assembly strategy was developed [4e]. In addition, the biological relevancies of typical annonaceous acetogenin mimetics were also studied [4f].

  13. Calamistrin E, the First Annonaceous Acetogenin with Double Bond in Aliphatic Chain from Genus Uvaria

    Institute of Scientific and Technical Information of China (English)

    2000-01-01

    Calamistrin E, the first Annonaceous acetogenin with C=C bond in the aliphatic chain from the genus Uvaria was isolated from U. calamistrata. Its structure including relative and absolute configurations was determined by chemical derivation and spectral analysis.

  14. Muricoreacin and murihexocin C, mono-tetrahydrofuran acetogenins, from the leaves of Annona muricata.

    Science.gov (United States)

    Kim, G S; Zeng, L; Alali, F; Rogers, L L; Wu, F E; Sastrodihardjo, S; McLaughlin, J L

    1998-09-01

    Bioactivity-directed fractionation of the leaves of Annona muricata L. (Annonaceae) resulted in the isolation of two new Annonaceous acetogenins, muricoreacin (1) and murihexocin C (2). Compounds 1 and 2 showed significant cytotoxicities among six human tumor cell lines with selectivities to the prostate adenocarcinoma (PC-3) and pancreatic carcinoma (PACA-2) cell lines.

  15. Five new monotetrahydrofuran ring acetogenins from the leaves of Annona muricata.

    Science.gov (United States)

    Zeng, L; Wu, F E; Oberlies, N H; McLaughlin, J L; Sastrodihadjo, S

    1996-11-01

    Bioactivity-directed fractionation of the leaves of Annona muricata resulted in the isolation of annopentocins A (1), B (2), and C(3), and cis- and trans-annomuricin-D-ones (4, 5). Compounds 1-3 are the first acetogenins reported bearing a mono-tetrahydrofuran (THF) ring with one flanking hydroxyl, on the hydrocarbon side, and another hydroxyl, on the lactone side, that is one carbon away from the THF ring. Compounds 4 and 5 were obtained in a mixture and are new mono-THF ring acetogenins bearing two flanking hydroxyls and an erythro-diol located between the THF and the ketolactone rings. Compound 1 was selectively cytotoxic to pancreatic carcinoma cells (PACA-2), and 2 and 3 were selectively cytotoxic to lung carcinoma cells (A-549); the mixture of 4 and 5 was selectively cytotoxic for the lung (A-549), colon (HT-29), and pancreatic (PACA-2) cell lines with potencies equal to or exceeding those of Adriamycin.

  16. Five novel mono-tetrahydrofuran ring acetogenins from the seeds of Annona muricata.

    Science.gov (United States)

    Rieser, M J; Gu, Z M; Fang, X P; Zeng, L; Wood, K V; McLaughlin, J L

    1996-02-01

    Bioactivity-directed fractionation of the seeds of Annona muricata L. (Annonaceae) resulted in the isolation of five new compounds: cis-annonacin (1), cis-annonacin-10-one (2), cis-goniothalamicin (3), arianacin (4), and javoricin (5). Three of these (1-3) are among the first cis mono-tetrahydrofuran ring acetogenins to be reported. NMR analyses of published model synthetic compounds, prepared cyclized formal acetals, and prepared Mosher ester derivatives permitted the determinations of absolute stereochemistries. Bioassays of the pure compounds, in the brine shrimp test, for the inhibition of crown gall tumors, and in a panel of human solid tumor cell lines for cytotoxicity, evaluated relative potencies. Compound 1 was selectively cytotoxic to colon adenocarcinoma cells (HT-29) in which it was 10,000 times the potency of adriamycin.

  17. Cohibins C and D, two important metabolites in the biogenesis of acetogenins from Annona muricata and Annona nutans.

    Science.gov (United States)

    Gleye, C; Raynaud, S; Fourneau, C; Laurens, A; Laprévote, O; Serani, L; Fournet, A; Hocquemiller, R

    2000-09-01

    Two new annonaceous acetogenins, cohibins C (1a) and D (1b), have been isolated by extensive chromatography of a hexane extract of Annona muricata seeds and a cyclohexane extract of Annona nutans root bark. Their structures have been established on the basis of spectral evidence (NMR, MS) and confirmed by chemical transformation into a pair of monotetrahydrofuran (mono-THF) acetogenins. The role of these compounds in the biogenesis of mono-THF acetogenins is discussed.

  18. MALDI-TOF MS profiling of annonaceous acetogenins in Annona muricata products for human consumption.

    Science.gov (United States)

    Champy, Pierre; Guérineau, Vincent; Laprévote, Olivier

    2009-12-15

    Annonaceous acetogenins are proposed as environmental neurotoxicants consumed through medicinal and alimentary habits and responsible for atypical parkinsonian syndromes observed in tropical areas. Potential sources of exposure still have to be determined, as, to date, only a few batches of products for human consumption were searched for these compounds. To assess the presence of acetogenins, we propose a fast, sensitive and accurate method of screening, using MALDI-TOF MS, with minimal sample preparation. Development of the technique is discussed. Its application to leaves of herbal tea, pulp and bottled nectar of Annona muricata is presented.

  19. MALDI-TOF MS Profiling of Annonaceous Acetogenins in Annona muricata Products for Human Consumption

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    Vincent Guérineau

    2009-12-01

    Full Text Available Annonaceous acetogenins are proposed as environmental neurotoxicants consumed through medicinal and alimentary habits and responsible for atypical parkinsonian syndromes observed in tropical areas. Potential sources of exposure still have to be determined, as, to date, only a few batches of products for human consumption were searched for these compounds. To assess the presence of acetogenins, we propose a fast, sensitive and accurate method of screening, using MALDI-TOF MS, with minimal sample preparation. Development of the technique is discussed. Its application to leaves of herbal tea, pulp and bottled nectar of Annona muricata is presented.

  20. Two New Bis-tetrahydrofuran Ring Annonaceous Acetogenins from the Roots of Uvaria calamistrata

    Institute of Scientific and Technical Information of China (English)

    2000-01-01

    Two mild-cytotoxic bistetrahydrofuran (THF) ring annonaceous acetogenins named calamistrins F (1) and G (2) were isolated from the ethanolic extract of the roots of U. calamistrata Hance. Their structures including the relative and absolute configurations were determined by chemical derivation and spectral analysis. Calamistrins F and G were a pair of epimers at C-26 which both had THF ring from C-18 to C-25 and three OH groups at C-5, C-17 and C-26.

  1. ANNONACEOUS ACETOGENINS OF THE SEEDS FROM ANNONA MURICATA

    Institute of Scientific and Technical Information of China (English)

    DE-YU LI; JING-GUANG YU; JIU-XIANG ZHU; DONG-LEI YU; XIU-ZHEN LUO; LAN SUN; SHI-LIN YANG

    2001-01-01

    Muricatenol (1) is a new C37 non-THF ring acetogenin with four hydroxyls and one isolated double bond in the long aliphatic chain. 2,4-cis-Gigantetrocinone (2) and 2,4-trans gigantetrocinone (3) have been isolated as their acetates by preparative TLC. 2,4-trans Isoannonacin-10-one (4) and 2,4-trans-isoannonacin (5) have been isolated as only 2,4-trans-form for the first time (no cis-form). Also four known acetogenins, gigantetrocin-A (6), gigantetrocin-B (7), annomontacin (8), gigantetronenin (9) and a mixture of N-fatty acyl tryptamines have been isolated (10). Their structures have been established on the basis of spectral analyses. The CHC13 fraction of the seeds showed strong antitumor activities.

  2. Annonaceous acetogenins of the seeds from Annona muricata.

    Science.gov (United States)

    Li, D Y; Yu, J G; Zhu, J X; Yu, D L; Luo, X Z; Sun, L; Yang, S L

    2001-01-01

    Muricatenol (1) is a new C37 non-THF ring acetogenin with four hydroxyls and one isolated double bond in the long aliphatic chain. 2,4-cis-Gigantetrocinone (2) and 2,4-trans-gigantetrocinone (3) have been isolated as their acetates by preparative TLC. 2,4-trans-Isoannonacin-10-one (4) and 2,4-trans-isoannonacin (5) have been isolated as only 2,4-trans-form for the first time (no cis-form). Also four known acetogenins, gigantetrocin-A (6), gigantetrocin-B (7), annomontacin (8), gigantetronenin (9) and a mixture of N-fatty acyl tryptamines have been isolated (10). Their structures have been established on the basis of spectral analyses. The CHCl3 fraction of the seeds showed strong antitumor activities.

  3. Characterization of the Annonaceous acetogenin, annonacinone, a natural product inhibitor of plasminogen activator inhibitor-1

    Science.gov (United States)

    Pautus, Stéphane; Alami, Mouad; Adam, Fréderic; Bernadat, Guillaume; Lawrence, Daniel A.; de Carvalho, Allan; Ferry, Gilles; Rupin, Alain; Hamze, Abdallah; Champy, Pierre; Bonneau, Natacha; Gloanec, Philippe; Peglion, Jean-Louis; Brion, Jean-Daniel; Bianchini, Elsa P.; Borgel, Delphine

    2016-11-01

    Plasminogen activator inhibitor-1 (PAI-1) is the main inhibitor of the tissue type and urokinase type plasminogen activators. High levels of PAI-1 are correlated with an increased risk of thrombotic events and several other pathologies. Despite several compounds with in vitro activity being developed, none of them are currently in clinical use. In this study, we evaluated a novel PAI-1 inhibitor, annonacinone, a natural product from the Annonaceous acetogenins group. Annonacinone was identified in a chromogenic screening assay and was more potent than tiplaxtinin. Annonacinone showed high potency ex vivo on thromboelastography and was able to potentiate the thrombolytic effect of tPA in vivo in a murine model. SDS-PAGE showed that annonacinone inhibited formation of PAI-1/tPA complex via enhancement of the substrate pathway. Mutagenesis and molecular dynamics allowed us to identify annonacinone binding site close to helix D and E and β-sheets 2A.

  4. Annonaceous acetogenins nanosuspensions stabilized by PCL–PEG block polymer: significantly improved antitumor efficacy

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    Hong JY

    2016-07-01

    Full Text Available Jingyi Hong,1,* Yanhong Li,1,2,* Yijing Li,1 Yao Xiao,1,2 Haixue Kuang,2 Xiangtao Wang1 1Key Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine, Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences, Peking Union Medical College, Beijing, 2School of Pharmacy, Heilongjiang University of Chinese Medicine, Harbin, People’s Republic of China *These authors contributed equally to this work Abstract: Annonaceous acetogenins (ACGs have shown superior antitumor activity against a variety of cancer cell lines, but their clinical application has been limited by their poor solubility. In this study, ACGs-nanosuspensions (NSps were successfully prepared by a precipitation ultrasonic method using monomethoxypoly (ethylene glycol2000–poly (ε-caprolactone2000 (mPEG2000–PCL2000 as a stabilizer. The resultant ACGs-NSps had a mean particle size of 123.2 nm, a zeta potential of -20.17 mV, and a high drug payload of 73.68%. ACGs-NSps were quite stable in various physiological solutions, and they exhibited sustained drug release. Compared to free drug, ACGs-NSps exhibited stronger cytotoxicity against 4T1, MCF-7, and HeLa cells. An in vivo real-time biodistribution investigation after labeling with 1,1'-dioctadecyltetramethyl indotricarbocyanine iodide, a noninvasive near-infrared fluorescence probe, demonstrated that ACGs-NSps could effectively accumulate in tumor. An in vivo antitumor activity study in 4T1 tumor-bearing mice revealed that ACGs-NSps achieved much better therapeutic efficacy than the traditional dosage form (oil solution even at 1/10 of the dose (74.83% vs 45.53%, P<0.05, demonstrating that NSp was a good dosage form for ACGs to treat cancer. Keywords: annonaceous acetogenins, mPEG2000–PCL2000, near–infrared fluorescence, biodistribution, antitumor efficacy

  5. Annonaceous acetogenins nanosuspensions stabilized by PCL-PEG block polymer: significantly improved antitumor efficacy

    Science.gov (United States)

    Hong, Jingyi; Li, Yanhong; Li, Yijing; Xiao, Yao; Kuang, Haixue; Wang, Xiangtao

    2016-01-01

    Annonaceous acetogenins (ACGs) have shown superior antitumor activity against a variety of cancer cell lines, but their clinical application has been limited by their poor solubility. In this study, ACGs-nanosuspensions (NSps) were successfully prepared by a precipitation ultrasonic method using monomethoxypoly (ethylene glycol)2000–poly (ε-caprolactone)2000 (mPEG2000–PCL2000) as a stabilizer. The resultant ACGs-NSps had a mean particle size of 123.2 nm, a zeta potential of −20.17 mV, and a high drug payload of 73.68%. ACGs-NSps were quite stable in various physiological solutions, and they exhibited sustained drug release. Compared to free drug, ACGs-NSps exhibited stronger cytotoxicity against 4T1, MCF-7, and HeLa cells. An in vivo real-time biodistribution investigation after labeling with 1,1′-dioctadecyltetramethyl indotricarbocyanine iodide, a noninvasive near-infrared fluorescence probe, demonstrated that ACGs-NSps could effectively accumulate in tumor. An in vivo antitumor activity study in 4T1 tumor-bearing mice revealed that ACGs-NSps achieved much better therapeutic efficacy than the traditional dosage form (oil solution) even at 1/10 of the dose (74.83% vs 45.53%, P<0.05), demonstrating that NSp was a good dosage form for ACGs to treat cancer. PMID:27486323

  6. HPLC Method for the Simultaneous Determination of Ten Annonaceous Acetogenins after Supercritical Fluid CO2 Extraction.

    Science.gov (United States)

    Yang, Haijun; Zhang, Ning; Zeng, Qingqi; Yu, Qiping; Ke, Shihuai; Li, Xiang

    2010-09-01

    Annonaceous acetogenins (ACGs) isolated from Annonaceae plants exhibited a broad range of biological bioactivities such as cytotoxic, antitumoral, antiparasitic, pesticidal and immunosuppresive activities. However, their structures were liable to change at more than 60°C and their extraction yields were low using traditional organic solvent extraction. In the present study, all samples from Annona genus plant seeds were extracted by supercritical carbon dioxide under optimized conditions and a high-performance liquid chromatography (HPLC) method was established for simultaneously determining ten ACGs. All of the ten compounds were simultaneously separated on reversed-phase C18 column (250 mm × 4.6 mm, 5 μm) with the column temperature at 30°C. The mobile phase was composed of (A) methanol and (B) distilled water, the flow rate was 1.0 ml/min and the detection wavelength was set at 220 nm. All calibration curves showed good linear regression (γ>0.9995) within the test range. The established method showed good precision and accuracy with overall intra-day and inter-day variations of 0.99-2.56% and 1.93-3.65%, respectively, and overall recoveries of 95.16-105.01% for the ten compounds analyzed. The established method can be applied to evaluate the intrinsic quality of Annonaceae plant seeds. The determination results recover the content-variation regularities of various ACGs in different species, which are helpful to choose the good-quality Annonaceae plant seeds for anticancer lead compound discovery.

  7. Acetogenins from Annonaceae.

    Science.gov (United States)

    Liaw, Chih-Chuang; Liou, Jing-Ru; Wu, Tung-Ying; Chang, Fang-Rong; Wu, Yang-Chang

    2016-01-01

    In recent decades, annonaceous acetogenins have become highly studied plant secondary metabolites in terms of their isolation, structure elucidation, synthesis, biological evaluation, mechanism of action, and toxicity. The aim of the present contribution is to summarize chemical and biological reports published since 1997 on annonaceous acetogenins and synthetic acetogenin mimics. The compounds are considered biologically in terms of their cytotoxicity for cancer cell lines, neurotoxicity, pesticidal effects, and miscellaneous activities.

  8. Additional bioactive acetogenins, annomutacin and (2,4-trans and cis)-10R-annonacin-A-ones, from the leaves of Annona muricata.

    Science.gov (United States)

    Wu, F E; Zhao, G X; Zeng, L; Zhang, Y; Schwedler, J T; McLaughlin, J L; Sastrodihardjo, S

    1995-09-01

    In a continuation of our research on bioactive components from the leaves of Annona muricata, three novel monotetrahydrofuran Annonaceous acetogenins, namely, annomutacin [1], (2,4-trans)-10R-annonacin-A-one [2], and (2,4-cis)-10R- annonacin-A-one [3], have been identified. Their structures were deduced by ms, nmr, ir, and uv spectral and chemical methods, and the absolute configurations were determined by Mosher ester methodology. A known bioactive amide, N-p-coumaroyl tyramine, was also found. Compound 1 and the mixture of compounds 2 and 3 showed selective cytotoxicities against the human A-549 lung tumor cell line.

  9. Comprehensive characterization of Annonaceous acetogenins within a complex extract by HPLC-ESI-LTQ-Orbitrap® using post-column lithium infusion.

    Science.gov (United States)

    Le Ven, Jessica; Schmitz-Afonso, Isabelle; Lewin, Guy; Laprévote, Olivier; Brunelle, Alain; Touboul, David; Champy, Pierre

    2012-11-01

    Annonaceous acetogenins (AAGs) are a homogenous class of polyketides proposed as environmental neurotoxins. Previous dereplication studies of AAGs were limited by the use of low-resolution mass spectrometers. Only poor information in terms of structures was provided due to the limited fragmentation of protonated or sodium cationized species. An innovative approach, using reversed-phase high-performance liquid chromatography coupled to a hybrid linear ion trap/orbitrap mass spectrometer (LTQ-Orbitrap®), was therefore performed. Sensitivity was enhanced by post-column infusion of lithium, since AAGs have a high affinity for this cation. High level of structural information was obtained from low-energy-collision-induced dissociation fragmentation experiments of lithium-cationized AAGs ([M + Li](+) ions) as demonstrated with purified standards. The method was then applied to a total ethyl-acetate extract prepared from commercial soursop nectar (Annona muricata L.). The sensitivity, mass accuracy and specific fragmentation patterns proved to be particularly useful for characterization of the AAGs. Typical structural identification procedure and unexpected observations for specific structural types are illustrated, with major and minor compounds.

  10. Anti-tumor effects of annonaceous acetogenins%番荔枝内酯抗肿瘤作用研究进展

    Institute of Scientific and Technical Information of China (English)

    张丹; 王晓文; 岳秉飞; 唐劲天

    2009-01-01

    Annonaceous anetogenins(ACG) are a large family of fatty acid-derivednatural products ex-tracted from annonacea with broad spectrum of anticancer activity. ACG are rich in resources and have broad prospects for development and application. In vivo studies show that ACG have great toxicity, which inhibites their applications and drug development. Chemical modification and structure reformation can improve the anti-tumor activity and bioavailability of ACG, which will be the direction for ACG anti-tumor drugs research.%番荔枝内酯(ACG)是一类从多种番荔枝科植物中提取的长碳链脂肪酸内酯,具有广谱抗肿瘤作用.番荔枝内酯来源丰富,具有广阔开发应用前景.动物实验发现,番荔枝内酯毒性较大.目前通过化学修饰或结构改造,提高其抗肿瘤活性、生物利用度并降低毒性,是番荔枝内酯药物的研发方向.

  11. A New Cytotoxic Acetogenin from the Seeds ofAnnona squamosa

    Institute of Scientific and Technical Information of China (English)

    2003-01-01

    A new Annonaceous acetogenin, squamostolide (1), was isolated from the seeds ofAnnona squamosa. Its structure was elucidated based on spectroscopic methods and comparisonwith known compounds. It is the first example of Annonaceous acetogenin with each of the twoends of the aliphatic chain bearing a γ-lactone. The new compound exhibited cytotoxic activity invitro against bel-7402 and CNE2 human tumor cell lines.

  12. Alkaloids and acetogenins in Annonaceae development: biological considerations

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    Alma Rosa González-Esquinca

    2014-01-01

    Full Text Available Chemical studies of the plant family Annonaceae have intensified in the last several decades due to the discovery of annonaceous molecules with medicinal potential (e.g., benzylisoquinoline alkaloids and acetogenins. Approximately 500 alkaloids have been identified in 138 Annonaceae species in 43 genera. In addition, until 2004, 593 annonaceous acetogenins (ACGs had been identified, from 51 species in 13 genera.This suggests that plants from this family allocate important resources to the biosynthesis of these compounds. Despite the diversity of these molecules, their biological roles, including their physiological and/or ecological functions, are not well understood. In this study, it was provided new data describing the variety and distribution of certain alkaloids and ACGs in annonaceous plants in distinct stages of development. The potential relationships among some of these compounds and the seasonally climatic changes occurring in the plant habitat are also discussed. These data will improve our understanding of the secondary metabolism of these pharmacologically important molecules and their expression patterns during development, which will help to determine the optimal growth conditions and harvest times for their production.

  13. Quantification of acetogenins in Annona muricata linked to atypical parkinsonism in guadeloupe.

    Science.gov (United States)

    Champy, Pierre; Melot, Alice; Guérineau Eng, Vincent; Gleye, Christophe; Fall, Djibril; Höglinger, Gunter U; Ruberg, Merle; Lannuzel, Annie; Laprévote, Olivier; Laurens, Alain; Hocquemiller, Reynald

    2005-12-01

    Atypical parkinsonism in Guadeloupe has been associated with the consumption of fruit and infusions or decoctions prepared from leaves of Annona muricata L. (Annonaceae), which contains annonaceous acetogenins, lipophilic inhibitors of complex I of the mitochondrial respiratory chain. We have determined the concentrations of annonacin, the major acetogenin in A. muricata, in extracts of fruit and leaves by matrix-assisted laser desorption-ionization mass spectrometry. An average fruit is estimated to contain about 15 mg of annonacin, a can of commercial nectar 36 mg, and a cup of infusion or decoction 140 microg. As an indication of its potential toxicity, an adult who consumes one fruit or can of nectar a day is estimated to ingest over 1 year the amount of annonacin that induced brain lesions in rats receiving purified annonacin by intravenous infusion.

  14. Annona muricata (Annonaceae): A Review of Its Traditional Uses, Isolated Acetogenins and Biological Activities.

    Science.gov (United States)

    Moghadamtousi, Soheil Zorofchian; Fadaeinasab, Mehran; Nikzad, Sonia; Mohan, Gokula; Ali, Hapipah Mohd; Kadir, Habsah Abdul

    2015-07-10

    Annona muricata is a member of the Annonaceae family and is a fruit tree with a long history of traditional use. A. muricata, also known as soursop, graviola and guanabana, is an evergreen plant that is mostly distributed in tropical and subtropical regions of the world. The fruits of A. muricata are extensively used to prepare syrups, candies, beverages, ice creams and shakes. A wide array of ethnomedicinal activities is contributed to different parts of A. muricata, and indigenous communities in Africa and South America extensively use this plant in their folk medicine. Numerous investigations have substantiated these activities, including anticancer, anticonvulsant, anti-arthritic, antiparasitic, antimalarial, hepatoprotective and antidiabetic activities. Phytochemical studies reveal that annonaceous acetogenins are the major constituents of A. muricata. More than 100 annonaceous acetogenins have been isolated from leaves, barks, seeds, roots and fruits of A. muricata. In view of the immense studies on A. muricata, this review strives to unite available information regarding its phytochemistry, traditional uses and biological activities.

  15. Annona muricata (Annonaceae: A Review of Its Traditional Uses, Isolated Acetogenins and Biological Activities

    Directory of Open Access Journals (Sweden)

    Soheil Zorofchian Moghadamtousi

    2015-07-01

    Full Text Available Annona muricata is a member of the Annonaceae family and is a fruit tree with a long history of traditional use. A. muricata, also known as soursop, graviola and guanabana, is an evergreen plant that is mostly distributed in tropical and subtropical regions of the world. The fruits of A. muricata are extensively used to prepare syrups, candies, beverages, ice creams and shakes. A wide array of ethnomedicinal activities is contributed to different parts of A. muricata, and indigenous communities in Africa and South America extensively use this plant in their folk medicine. Numerous investigations have substantiated these activities, including anticancer, anticonvulsant, anti-arthritic, antiparasitic, antimalarial, hepatoprotective and antidiabetic activities. Phytochemical studies reveal that annonaceous acetogenins are the major constituents of A. muricata. More than 100 annonaceous acetogenins have been isolated from leaves, barks, seeds, roots and fruits of A. muricata. In view of the immense studies on A. muricata, this review strives to unite available information regarding its phytochemistry, traditional uses and biological activities.

  16. Infrared spectral evidence and DFT calculations of hydrogen-bonding and molecular structures of acetogenins

    Science.gov (United States)

    Afonso, Sabrina; Silva, Fabiano B.; Silva, Arnaldo F.; Scarminio, Ieda S.; Bruns, Roy E.

    2017-02-01

    FTIR spectra have been measured for 31 different five component - simplex centroid design solvent mixture extracts of shaded and sun-exposed Annonaceous leaves harvested in all four seasons. The spectral frequencies are characteristic of anonnaceous acetogenins known to be a major component of these leaves. Osbnd H stretching spectral bands in the 3100-3600 cm-1 region provide evidence of notable intensity changes for the shaded and sun-exposed leaves. Chemometric principal component analysis involving 264 spectra show that shaded samples tend to have more intense Osbnd H stretching bands than those grown in the sun. B3LYP density functional calculations indicate significant Osbnd H stretching band changes in this region owing to hydrogen bond formation. Weak Osbnd H intensity enhancements, around 40 km mol-1, occur when an Osbnd H group forms a hydrogen bond with the oxygen atom of an adjacent tetrahydrofuran ring oxygen atom. Much more intense enhancements, 400-500 km mol-1, are predicted to occur for acetogenins with two tetrahydrofuran rings for which the Osbnd H group hydrogen bonds with its fartherest removed tetrahydrofuran ring oxygen. Whereas weak or moderate H-bond stretching intensities are obtained for acetogenins with slightly bent carbon chain structures the strongest hydrogen bond intensities are calculated for molecules with a 45° V-type backbone structure. These important structural modifications as well as significant changes in bond lengths and angles owing to hydrogen bonding are detailed.

  17. Synergistic interactions among flavonoids and acetogenins in Graviola (Annona muricata) leaves confer protection against prostate cancer.

    Science.gov (United States)

    Yang, Chunhua; Gundala, Sushma Reddy; Mukkavilli, Rao; Vangala, Subrahmanyam; Reid, Michelle D; Aneja, Ritu

    2015-06-01

    Phytochemical complexity of plant extracts may offer health-promoting benefits including chemotherapeutic and chemopreventive effects. Isolation of 'most-active fraction' or single constituents from whole extracts may not only compromise the therapeutic efficacy but also render toxicity, thus emphasizing the importance of preserving the natural composition of whole extracts. The leaves of Annona muricata, commonly known as Graviola, are known to be rich in flavonoids, isoquinoline alkaloids and annonaceous acetogenins. Here, we demonstrate phytochemical synergy among the constituents of Graviola leaf extract (GLE) compared to its flavonoid-enriched (FEF) and acetogenin-enriched (AEF) fractions. Comparative quantitation of flavonoids revealed enrichment of rutin (~7-fold) and quercetin-3-glucoside (Q-3-G, ~3-fold) in FEF compared to GLE. In vivo pharmacokinetics and in vitro absorption kinetics of flavonoids revealed enhanced bioavailability of rutin in FEF compared to GLE. However, GLE was more effective in inhibiting in vitro prostate cancer proliferation, viability and clonogenic capacity compared to FEF. Oral administration of 100mg/kg bw GLE showed ~1.2-fold higher tumor growth-inhibitory efficacy than FEF in human prostate tumor xenografts although the concentration of rutin and Q-3-G was more in FEF. Contrarily, AEF, despite its superior in vitro and in vivo efficacy, resulted in death of the mice due to toxicity. Our data indicate that despite lower absorption and bioavailability of rutin, maximum efficacy was achieved in the case of GLE, which also comprises of other phytochemical groups including acetogenins that make up its natural complex environment. Hence, our study emphasizes on evaluating the nature of interactions among Graviola leaf phytochemcials for developing favorable dose regimen for prostate cancer management to achieve optimal therapeutic benefits.

  18. Murihexol, a linear acetogenin from Annona muricata.

    Science.gov (United States)

    Yu, Jing Guang; Gui, Hua Qing; Luo, Xiu Zhen; Sun, Lan

    1998-11-20

    Murihexol (1), a novel acetogenin, and three known ones, donhexocin (2), annonacin A and annonacin, have been isolated from the seeds of Annona muricata. Compound 1 is a C(35) acetogenin without any THF rings, with six hydroxyls in the long aliphatic chain. The hydroxyls of 1 and 2 are all located at C-4, C-10, C-15, C-16, C-19 and C-20, but their stereochemistries are different. The vicinal diol at C-15/C-16 in 1 is threo and C-19/C-20 has the erythro configuration; in 2 C-15/C-16 and C-19/C-20 all have the same threo configuration.

  19. Muricatenol, a Linear Acetogenin from Annona muricata (Annonaceae)

    Institute of Scientific and Technical Information of China (English)

    2000-01-01

    Muricatenol 1, a new acetogenin, has been isolated from the seeds of Annona muricata L.. Compound 1 is a C37 acetogenin without any THF rings, with four hydroxyls and one double bond in the long aliphatic chain. The hydroxyls of 1 are located at C-4, C-10, C-18 and C-19, respectively. The vicinal diol at C-18/C-19 is threo-configuration, and the double bond at C-14/C-15 is cis-configuration.

  20. C-15 ACETOGENINS FROM THE MARINE ALGA Chondria

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    Antonius R.B. Ola

    2010-06-01

    Full Text Available (- Z-Pinnatifidenyne, a novel C-15 acetogenin has been isolated along with the known compound (+-3Z,6R,7R-obtusenyne and (+ (3Z-laurenyne from the Australian red alga Chondria armata. The structures of the compounds were elucidated based on spectral data analysis including 2D NMR spectroscopic experiment.   Keywords: Chondria armata, C-15 acetogenin, 2D NMR

  1. C15 acetogenins from the Laurencia complex: 50 years of research – an overview

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    Tauana Wanke

    2015-12-01

    Full Text Available Abstract Acetogenins are secondary metabolites derived from the polyketide pathway and their potential role as chemotaxonomical markers for red algae belonging to the Laurencia complex has been long pointed out. C15 acetogenins from algae are quite different from plant acetogenins: they are usually halogenated, and have an enyne or a bromoallene terminal group. Since they were first reported, laurencin and other algal acetogenins have inspired great curiosity among natural product chemists and also those working with synthesis. This paper reviews the literature about C15 acetogenins, focusing on their distribution, chemical and biological aspects, including their reported biological activities.

  2. Biological screening of Annonaceous Brazilian Medicinal Plants using Artemia salina (brine shrimp test).

    Science.gov (United States)

    Santos Pimenta, L P; Pinto, G B; Takahashi, J A; e Silva, L G F; Boaventura, M A D

    2003-03-01

    Eighteen different extracts from five Annona species collected in Minas Gerais state, Brazil, were submitted to the brine shrimp lethality test in order to detect potential sources of novel cytotoxic, antitumor, pesticidal and anti-Trypanosoma cruzi compounds. All of the Annonaceous species tested showed good larvicidal activity as compared to a reference compounds and literature data.

  3. Coronin from roots of Annona muricata, a putative intermediate in acetogenin biosynthesis (1).

    Science.gov (United States)

    Gleye, C; Akendengue, B; Laurens, A; Hocquemiller, R

    2001-08-01

    A novel acetogenin, coronin, was isolated from the roots of Annona muricata L. The structure was elucidated by a combination of chemical and spectral methods including MS and NMR measurements. Coronin is probably an intermediate in the biosynthetic pathway of bis-tetrahydrofuran acetogenins, and is proposed as a biogenetic precursor of neoannonin-B.

  4. Acetogenins in Annona muricata L. (annonaceae) leaves are potent molluscicides.

    Science.gov (United States)

    Luna, J De S; De Carvalho, J M; De Lima, M R F; Bieber, L W; Bento, Edson De S; Franck, X; Sant'ana, A E G

    2006-03-01

    An ethanolic extract of the leaves of Annona muricata was shown to be toxic to adult forms of the snail Biomphalaria glabrata (LC50 9.32 microg mL(-1)) and to larvae of the brine shrimp Artemia salina (LC50 0.49 microg mL(-1)). Activity-guided fractionation of the extract gave rise to a sample with high molluscicidal activity that contained the acetogenins, annonacin (90%), isoannonacin (6%) and goniothalamicin (4%).

  5. DETERMINATION OF ANNONACEOUS ACETOGENINS IN ANNONACEAE PLANTS BY HPLC%HPLC法测定番荔枝科植物中番荔素含量

    Institute of Scientific and Technical Information of China (English)

    孙兰; 余竞光; 李德宇; 李进; 杨学东; 杨世林

    2001-01-01

    目的建立番荔枝科植物中抗肿瘤活性成分番荔素的HPLC含量测定方法.方法 Squamostatin-B (1),squamocin (2 )和annonin-VI (3)为标准品.色谱柱:反相C18柱;流动相:甲醇-水(90∶10);流速:1.0 mL*min-1;检测波长:220 nm.结果进样量在2.3-13.8 μg有良好的线性关系.(1),(2)和(3)的回收率分别为100.3%,100.3%和100.0%.结论本法快速、简便、灵敏和分离度好,适用于番荔枝科植物中抗肿瘤活性成分番荔素的含量测定.

  6. In vitro antileishmanial activity of acetogenins from Annonaceae.

    Science.gov (United States)

    Raynaud-Le Grandic, S; Fourneau, C; Laurens, A; Bories, C; Hocquemiller, R; Loiseau, P M

    2004-01-01

    Twelve acetogenins from Annonaceae were evaluated in vitro for their antileishmanial activities in order to search for new lead-compounds having antileishmanial properties. The compounds were comparatively evaluated by the 50% inhibitory concentrations (IC50) determination on promastigote forms of wild-type and four drug-resistant lines of Leishmania donovani. In addition, after testing the toxicity on mouse peritoneal macrophages, the compounds were evaluated on amastigote infected macrophages and a therapeutic index was calculated. The IC50 of the acetogenins against promastigote forms of L. donovani was in a range 4.7-47.3 microM. The most active compound was Rolliniastatin 1 (IC50 at 4.7 microM). On the intramacrophage amastigote in vitro model, only seven compounds exhibited measurable antileishmanial activity with IC50 values in a range 2.5-29.7 microM. Rollinistatin 1 was the most interesting compound with IC50 of 2.5 microM and it appears as the most promising one on the basis of therapeutic index (18.08). Isoannonacin, which is active against intramacrophagic amastigotes (IC50 of 6.2 microM) with a therapeutic index of 2.05, exhibited a strong action on drug-resistant strains (IC50 from 5.1 to 9.8 microM). Acetogenins are a new chemical series with interesting in vitro antileishmanial activity and further studies will be focused on the understanding of this selectivity in regard to the membrane and mitochondrial action using specific probes.

  7. Cytotoxic acetogenins from Annona glabra cultivated in Egypt

    Directory of Open Access Journals (Sweden)

    Ahmed Abdel-lateff

    2009-01-01

    Full Text Available Bio-assay guided fraction of the methanolic extract of Annona glabra seeds (Annonaceae, cultivated in Egypt, revealed to the isolation of three bis-tetrahydrofuran acetogenins; squamocin-C (1 , squamocin-D (2 , and annonin I (3 . Compounds 1 and 2 were obtained as stereoisomeric mixture. All isolates were assayed for their cytotoxicity twards brine shrimp and five in vitro cancer cell lines (A549, HT29, MCF 7, RPMI, and U251, and showed significant activity The structures of all compounds were determined by interpretation of their NMR and MS analyses.

  8. Cardiotoxicity of acetogenins from Persea americana occurs through the mitochondrial permeability transition pore and caspase-dependent apoptosis pathways.

    Science.gov (United States)

    Silva-Platas, Christian; García, Noemí; Fernández-Sada, Evaristo; Dávila, Daniel; Hernández-Brenes, Carmen; Rodríguez, Dariana; García-Rivas, Gerardo

    2012-08-01

    Acetogenins are cell-membrane permeable, naturally occurring secondary metabolites of plants such as Annonaceae, Lauraceae and other related phylogenic families. They belong to the chemical derivatives of polyketides, which are synthesized from fatty acid precursors. Although acetogenins have displayed diverse biological activities, the anti-proliferative effect on human cancer cells has been widely reported. Acetogenins are inhibitors of complex I in the electron transport chain therefore they interrupt ATP synthesis in mitochondria. We tested a new acetogenins-enriched extract from the seed of Persea americana in order to investigate if any toxicity was induced on cardiac tissue and determine the involved mechanism. In isolated perfused heart we found that contractility was completely inhibited at an accumulative dose of 77 μg/ml. In isolated cardiomyocytes, the acetogenins-enriched extract induced apoptosis through the activation of the intrinsic pathway at 43 μg/ml. In isolated mitochondria, it inhibited complex I activity on NADH-linked respiration, as would be expected, but also induced permeability transition on succinate-linked respiration. Cyclosporine A, a known blocker of permeability transition, significantly prevented the permeability transition triggered by the acetogenins-enriched extract. In addition, our acetogenins-enriched extract inhibited ADP/ATP exchange, suggesting that an important element in phosphate or adenylate transport was affected. In this manner we suggest that acetogenins-enriched extract from Persea americana could directly modulate permeability transition, an entity not yet associated with the acetogenins' direct effects, resulting in cardiotoxicity.

  9. Activity-guided identification of acetogenins as novel lipophilic antioxidants present in avocado pulp (Persea americana).

    Science.gov (United States)

    Rodríguez-Sánchez, Dariana; Silva-Platas, Christian; Rojo, Rocío P; García, Noemí; Cisneros-Zevallos, Luis; García-Rivas, Gerardo; Hernández-Brenes, Carmen

    2013-12-30

    Avocado fruit is a rich source of health-related lipophilic phytochemicals such as monounsaturated fatty acids, tocopherols, carotenes, acetogenins and sterols. However, limited information is available on the contribution of specific phytochemicals to the overall antioxidant capacity (AOC) of the fruit. Centrifugal partition chromatography was used as fractionation tool, guided by an in vitro chemical assay of oxygen radical absorbance capacity (ORAC). Subsequent experiments focused on isolation and characterization of the chemical nature of the main contributors to lipophilic AOC of avocado pulp. ORAC values obtained for acetogenins were contrasted with results from an isolated kidney mitochondria membrane lipid peroxidation bioassay. The present study established that lipophilic AOC of the pulp was significantly higher than its hydrophilic AOC. Our results confirmed the presence of acetogenins in the fractions with highest lipophilic AOC, and for the first time linked them as contributors to lipophilic-ORAC values. Further HPLC-PDA/MS-TOF analysis led to structural elucidation of two novel acetogenins, not previously reported as present in avocado pulp, along with five already known related-compounds. Antioxidant properties observed for avocado pulp acetogenins by the ORAC assay suggested that, in the presence of an emulsifying agent, acetogenins could serve as novel lipophilic antioxidants in a food matrix. Results from isolated mitochondria lipid peroxidation bioassay, indicated that L-ORAC values which may have relevance for food matrix applications, should not be interpreted to have a direct relevance in health-related claims, compounds need to be evaluated considering the complexity of biological systems.

  10. Sesquiterpene and Acetogenin Derivatives from the Marine Red Alga Laurencia okamurai

    Directory of Open Access Journals (Sweden)

    Bin-Gui Wang

    2012-12-01

    Full Text Available In addition to 13 known compounds, four new bisabolane sesquiterpenes, okamurenes A–D (1–4, a new chamigrane derivative, okamurene E (5, and a new C12-acetogenin, okamuragenin (6, were isolated from the marine red alga Laurencia okamurai. The structures of these compounds were determined through detailed spectroscopic analyses. Of these, okamurenes A and B (1 and 2 are the first examples of bromobisabolane sesquiterpenes possessing a phenyl moiety among Laurencia-derived sesquiterpenes, while okamuragenin (6 was the first acetogenin aldehyde possessing a C12-carbon skeleton. Each of the isolated compounds was evaluated for the brine shrimp (Artemia salina lethal assay and 7-hydroxylaurene displayed potent lethality with LD50 1.8 μM.

  11. Acetogenins from Annonaceae: recent progress in isolation, synthesis and mechanisms of action.

    Science.gov (United States)

    Bermejo, Almudena; Figadere, Bruno; Zafra-Polo, Maria-Carmen; Barrachina, Isabel; Estornell, Ernesto; Cortes, Diego

    2005-04-01

    The aim of the present review is to summarise the knowledge about newly isolated acetogenins (ACGs) in the last six years. It will also report the total syntheses that have allowed either the confirmation or the revision of some structures, together with the biological activities and mechanism of action of such interesting natural products. In fact, of the 417 isolated compounds reviewed, over 176 have been added during the period from 1998 to 2004.

  12. Acetogenins from Annona muricata as potential inhibitors of antiapoptotic proteins: a molecular modeling study

    Science.gov (United States)

    Antony, Priya; Vijayan, Ranjit

    2016-01-01

    Apoptosis is a highly regulated process crucial for maintaining cellular homeostasis and development. The B-cell lymphoma 2 (Bcl-2) family of proteins play a crucial role in regulating apoptosis. Overexpressed Bcl-2 proteins are associated with the development and progression of several human cancers. Annona muricata is a tropical plant that belongs to the Annonaceae family and is well known for its anticancer properties. In this study, molecular docking and simulations were performed to investigate the inhibitory potential of phytochemicals present in A. muricata against antiapoptotic proteins of the Bcl-2 family including Bcl-2, B-cell lymphoma extra-large (Bcl-Xl), and Mcl-1. Docking results revealed that the acetogenins, such as annomuricin A, annohexocin, muricatocin A, annomuricin-D-one, and muricatetrocin A/B, exhibited strong binding interactions with Bcl-Xl when compared to Bcl-2 and Mcl-1. Binding score and interactions of these acetogenins were notably better than those of currently available synthetic and natural inhibitors. Molecular dynamics simulations of the top-scoring lead molecules established that these molecules could bind strongly and consistently in the active site of Bcl-Xl. These results suggest that acetogenins could be explored as selective natural inhibitors of Bcl-Xl that could assist in promoting the intrinsic pathway of apoptosis. PMID:27110097

  13. Acetogenins from Annona muricata as potential inhibitors of antiapoptotic proteins: a molecular modeling study.

    Science.gov (United States)

    Antony, Priya; Vijayan, Ranjit

    2016-01-01

    Apoptosis is a highly regulated process crucial for maintaining cellular homeostasis and development. The B-cell lymphoma 2 (Bcl-2) family of proteins play a crucial role in regulating apoptosis. Overexpressed Bcl-2 proteins are associated with the development and progression of several human cancers. Annona muricata is a tropical plant that belongs to the Annonaceae family and is well known for its anticancer properties. In this study, molecular docking and simulations were performed to investigate the inhibitory potential of phytochemicals present in A. muricata against antiapoptotic proteins of the Bcl-2 family including Bcl-2, B-cell lymphoma extra-large (Bcl-Xl), and Mcl-1. Docking results revealed that the acetogenins, such as annomuricin A, annohexocin, muricatocin A, annomuricin-D-one, and muricatetrocin A/B, exhibited strong binding interactions with Bcl-Xl when compared to Bcl-2 and Mcl-1. Binding score and interactions of these acetogenins were notably better than those of currently available synthetic and natural inhibitors. Molecular dynamics simulations of the top-scoring lead molecules established that these molecules could bind strongly and consistently in the active site of Bcl-Xl. These results suggest that acetogenins could be explored as selective natural inhibitors of Bcl-Xl that could assist in promoting the intrinsic pathway of apoptosis.

  14. In situ histochemical localisation of alkaloids and acetogenins in the endosperm and embryonic axis of Annona macroprophyllata Donn. Sm. seeds during germination.

    Science.gov (United States)

    Brechú-Franco, A E; Laguna-Hernández, G; De la Cruz-Chacón, I; González-Esquinca, A R

    2016-02-01

    Currently, the Annonaceae family is characterised by the production of acetogenins (ACGs), and also by the biosynthesis of alkaloids, primarily benzylisoquinolines derived from tyrosine. The objective of this study was to confirm the presence of alkaloids and acetogenins in the idioblasts of the endosperm and the embryonic axis of A. macroprophyllata seeds in germination. The Dragendorff, Dittmar, Ellram, and Lugol reagents were used to test for alkaloids, and Kedde's reagent was used to determine the presence of acetogenins in fresh sections of the endosperm and embryonic axis of seeds after twelve days of germination. A positive reaction was observed for all the reagents, and the presence of alkaloids and acetogenins was confirmed in the idioblasts of the endosperm and those involved in the differentiation of the embryonic axis of the developing seedling. We concluded that the idioblasts store both metabolites, acetogenins and alkaloids. Beginning at differentiation, the idioblasts of the embryonic axis simultaneously biosynthesise acetogenins and alkaloids that are characteristic of the species during the development of the seedling. The method used here can be applied to histochemically confirm the presence of acetogenins and alkaloids in tissues and structures of the plant in different stages of its life cycle.

  15. In situ histochemical localisation of alkaloids and acetogenins in the endosperm and embryonic axis of Annona macroprophyllata Donn. Sm. seeds during germination

    Directory of Open Access Journals (Sweden)

    A.E. Brechú-Franco

    2016-02-01

    Full Text Available Currently, the Annonaceae family is characterised by the production of acetogenins (ACGs, and also by the biosynthesis of alkaloids, primarily benzylisoquinolines derived from tyrosine. The objective of this study was to confirm the presence of alkaloids and acetogenins in the idioblasts of the endosperm and the embryonic axis of A. macroprophyllata seeds in germination. The Dragendorff, Dittmar, Ellram, and Lugol reagents were used to test for alkaloids, and Kedde’s reagent was used to determine the presence of acetogenins in fresh sections of the endosperm and embryonic axis of seeds after twelve days of germination. A positive reaction was observed for all the reagents, and the presence of alkaloids and acetogenins was confirmed in the idioblasts of the endosperm and those involved in the differentiation of the embryonic axis of the developing seedling. We concluded that the idioblasts store both metabolites, acetogenins and alkaloids. Beginning at differentiation, the idioblasts of the embryonic axis simultaneously biosynthesise acetogenins and alkaloids that are characteristic of the species during the development of the seedling. The method used here can be applied to histochemically confirm the presence of acetogenins and alkaloids in tissues and structures of the plant in different stages of its life cycle.

  16. Isolaurenidificin and Bromlaurenidificin, Two New C15-Acetogenins from the Red Alga Laurencia obtusa.

    Science.gov (United States)

    Bawakid, Nahed O; Alarif, Walied M; Alburae, Najla A; Alorfi, Hajer S; Al-Footy, Khalid O; Al-Lihaibi, Sultan S; Ghandourah, Mohamed A

    2017-05-15

    Chromatographic fractionation of the CH₂Cl₂/MeOH extract of the Red Sea red alga Laurencia obtusa gave two new hexahydrofuro[3,2-b]furan-based C15-acetogenins, namely, isolaurenidificin (1) and bromlaurenidificin (2). The chemical structures were elucidated based on extensive analyses of their spectral data. Compounds 1 and 2 showed no toxicity (LC50 > 12 mM) using Artemia salina as test organism. Both compounds showed weak cytotoxicity against A549, HepG-2, HCT116, MCF-7, and PC-3 cells, however, they exhibited a relatively potent cytotoxic activity against peripheral blood neutrophils. This can be attributed partly to induction of apoptosis.

  17. Different susceptibilities of Leishmania spp. promastigotes to the Annona muricata acetogenins annonacinone and corossolone, and the Platymiscium floribundum coumarin scoparone.

    Science.gov (United States)

    Vila-Nova, Nadja Soares; de Morais, Selene Maia; Falcão, Maria José Cajazeiras; Alcantara, Terezinha Thaize Negreiros; Ferreira, Pablito Augusto Travassos; Cavalcanti, Eveline Solon Barreira; Vieira, Icaro Gusmão Pinto; Campello, Cláudio Cabral; Wilson, Mary

    2013-03-01

    Leishmaniasis is a zoonotic disease that can manifest itself in visceral and cutaneous form. The aim of this study was to search for new leishmanicidal compounds. Preliminarily, Artemia salina assay was applied to compounds from two plants found in Northeastern Brazil, Platymiscium floribundum and Annona muricata. Then these compounds were tested against three Leishmania species (Leishmania donovani, Leishmania mexicana and Leishmania major). A screening assay using luciferase-expressing promastigote form were used to measure the viability of promastigote One coumarin, scoparone, isolated from P. floribundum and two acetogenins, annonacinone and corossolone isolated from A. muricata showed leishmanicidal activity in all species tested. Nevertheless, Leishmania species indicated different susceptibilities in relation to the tested compounds: L. mexicana was more sensitive to scoparone followed by L. major and L. donovani. The three species presented similar inhibition to corossolone and annonacinone. Acetogenin annonacinone (EC(50)=6.72-8.00 μg/mL) indicated high leishmanicidal activity; corossolone (EC(50)=16.14-18.73 μg/mL) and scoparone (EC(50)=9.11-27.51 μg/mL) moderate activity. A. saline larvae were less sensitive to the coumarin scoparone and acetogenin corossolone was the most toxic. In conclusion, the leishmanicidal activity demonstrated by the coumarin and acetogenins indicate these compounds for further studies aiming the development of new leishmanicidal agents.

  18. Dynamic Function of the Alkyl Spacer of Acetogenins as Potent Inhibitors of Mitochondrial Complex I. A Molecular Dynamics Simulation Approach

    NARCIS (Netherlands)

    Abel Bombasaro, Jose; Barrera Guisasola, Exequiel Ernesto; Masman, Marcelo Fabricio; Angel Zamora, Miguel; Maria Rodriguez, Ana

    2013-01-01

    Acetogenins are among the most potent of the known inhibitors of complex I (NADH-ubiquinone oxidoreductase) in mitochondrial electron transfer system. Elucidation of the dynamic function of the alkyl spacer linking the two toxophores (i.e., the hydroxylated tetrahydrofuran and the gamma-lactone

  19. Halogenated Terpenes and a C15-Acetogenin from the Marine Red Alga Laurencia saitoi

    Directory of Open Access Journals (Sweden)

    Xiao-Ming Li

    2008-11-01

    Full Text Available Seven parguerane diterpenes: 15-bromo-2,7,19-triacetoxyparguer-9(11-en-16-ol (1, 15-bromo-2,7,16,19-tetraacetoxyparguer-9(11-ene (2, 15-bromo-2,19-diacetoxyparguer-9(11-en-7,16-diol (3, 15-bromo-2,16,19-triacetoxyparguer-9(11-en-7-ol (4, 15-bromo-2,16-diacetoxyparguer-9(11-en-7-ol (5, 15-bromoparguer-9(11-en-16-ol (6, 15-bromoparguer-7-en-16-ol (7, two polyether triterpenes: thyrsiferol (8 and thyrsiferyl 23-acetate (9, and one C15-acetogenin, neolaurallene (10, were isolated from a sample of marine red alga Laurencia saitoi collected off the coast of Yantai. Their structures were established by detailed NMR spectroscopic analysis and comparison with literature data.

  20. [Studies on the chemical constituents of Annona muricata].

    Science.gov (United States)

    Yu, J G; Gui, H Q; Luo, X Z; Sun, L; Zhu, P; Yu, Z L

    1997-06-01

    Annonaceous acetogenin (or polyketide) is a kind of potential antineoplastic agents from Annonaceae plants. Two new acetogenins, Muricatalicin (I) and muricatalin (VI), a mesitoate of a new acetogenin, annonacin-B mesitoate (Vb), and three known acetogenins, annonacin (II), annonacin-A (III) and annonacin-10-one (IV) have been isolated from Annona muricata L. The structures and relative stereochemistry of I, VI and Vb were elucidated on the basis of spectral analysis and examination of their acetates and/or mesitoate.

  1. Isolation of Montecristin, a Key Metabolite in Biogenesis of Acetogenins from Annona muricata and Its Structure Elucidation by Using Tandem Mass Spectrometry.

    Science.gov (United States)

    Gleye, C.; Laurens, A.; Hocquemiller, R.; Cavé, A.; Laprévote, O.; Serani, L.

    1997-02-07

    During the course of our continuing search for acetogenins from Annonaceae, a new metabolite, montecristin, possibly involved in the biogenesis of acetogenins, was isolated from the roots of Annona muricata. Its structure was elucidated on the basis of UV, IR, (1)H and (13)C NMR, and mass spectrometry. The identification of the main stuctural features of montecristin (1) was obtained from the NMR spectra whereas their locations on the alkyl chain were evidenced by using mass spectrometry. The attribution of each carbon and location of substituents on the alkyl chain of this fatty acid gamma-lactone was evidenced by using tandem mass spectrometry (MS/MS) and high-energy collisional activation of [M + Li](+) lithium complexes. Finally, the structure determination of montecristin was strengthened by epoxidation and transformation leading to a known adjacent bis-tetrahydrofuran acetogenin.

  2. Aliphatic acetogenin constituents of avocado fruits inhibit human oral cancer cell proliferation by targeting the EGFR/RAS/RAF/MEK/ERK1/2 pathway

    Energy Technology Data Exchange (ETDEWEB)

    D' Ambrosio, Steven M. [Department of Radiology, College of Medicine, The Ohio State University, Columbus, OH 43210 (United States); Comprehensive Cancer Center, The Ohio State University, Columbus, OH 43210 (United States); Han, Chunhua [Department of Radiology, College of Medicine, The Ohio State University, Columbus, OH 43210 (United States); Pan, Li; Douglas Kinghorn, A. [Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, OH 43210 (United States); Ding, Haiming, E-mail: ding.29@osu.edu [Department of Radiology, College of Medicine, The Ohio State University, Columbus, OH 43210 (United States)

    2011-06-10

    Highlights: {yields} The aliphatic acetogenins [(2S,4S)-2,4-dihydroxyheptadec-16-enyl acetate] (1) and [(2S,4S)-2,4-dihydroxyheptadec-16-ynyl acetate] (2) isolated from avocado fruit inhibit phosphorylation of c-RAF (Ser338) and ERK1/2 (Thr202/Tyr204). {yields} Aliphatic acetogenin 2, but not 1, prevents EGF-induced activation of EGFR (Tyr1173). {yields} Combination of both aliphatic acetogenins synergistically inhibits c-RAF (Ser338) and ERK1/2 (Thr202/Tyr204) phosphorylation and human oral cancer cell proliferation. {yields} The potential anticancer activity of avocado fruits is due to a combination of specific aliphatic acetogenins targeting two key components of the EGFR/RAS/RAF/MEK/ERK1/2 cancer pathway. {yields} Providing a double hit on a critical cancer pathway such as EGFR/RAS/RAF/MEK/ERK1/2 by phytochemicals like those found in avocado fruit could lead to more effective approach toward cancer prevention. -- Abstract: Avocado (Persea americana) fruits are consumed as part of the human diet and extracts have shown growth inhibitory effects in various types of human cancer cells, although the effectiveness of individual components and their underlying mechanism are poorly understood. Using activity-guided fractionation of the flesh of avocado fruits, a chloroform-soluble extract (D003) was identified that exhibited high efficacy towards premalignant and malignant human oral cancer cell lines. From this extract, two aliphatic acetogenins of previously known structure were isolated, compounds 1 [(2S,4S)-2,4-dihydroxyheptadec-16-enyl acetate] and 2 [(2S,4S)-2,4-dihydroxyheptadec-16-ynyl acetate]. In this study, we show for the first time that the growth inhibitory efficacy of this chloroform extract is due to blocking the phosphorylation of EGFR (Tyr1173), c-RAF (Ser338), and ERK1/2 (Thr202/Tyr204) in the EGFR/RAS/RAF/MEK/ERK1/2 cancer pathway. Compounds 1 and 2 both inhibited phosphorylation of c-RAF (Ser338) and ERK1/2 (Thr202/Tyr204). Compound 2, but not

  3. Highly cytotoxic and neurotoxic acetogenins of the Annonaceae: new putative biological targets of squamocin detected by activity-based protein profiling.

    Science.gov (United States)

    Derbré, Séverine; Gil, Sophie; Taverna, Myriam; Boursier, Céline; Nicolas, Valérie; Demey-Thomas, Emmanuelle; Vinh, Joëlle; Susin, Santos A; Hocquemiller, Reynald; Poupon, Erwan

    2008-11-01

    Acetogenins of the Annonaceae are strong inhibitors of mitochondrial complex I but discrepancies in the structure/activity relationships pled the search for other targets within the whole cell proteome. Combining hemisynthetic work, Cu-catalyzed Huisgen cycloaddition and proteomic techniques we have identified new putative protein targets of squamocin ruling out the previously accepted 'complex I dogma'. These results give new insights into the mechanism of action of these potent neurotoxic molecules.

  4. Aliphatic acetogenin constituents of avocado fruits inhibit human oral cancer cell proliferation by targeting the EGFR/RAS/RAF/MEK/ERK1/2 pathway

    Science.gov (United States)

    D’Ambrosio, Steven M.; Han, Chunhua; Pan, Li; Kinghorn, A. Douglas; Ding, Haiming

    2011-01-01

    Avocado (Persea americana) fruits are consumed as part of the human diet and extracts have shown growth inhibitory effects in various types of human cancer cells, although the effectiveness of individual components and their underlying mechanism are poorly understood. Using activity-guided fractionation of the flesh of avocado fruits, a chloroform-soluble extract (D003), was identified that exhibited high efficacy towards premalignant and malignant human oral cancer cell lines. From this extract, two aliphatic acetogenins of previously known structure were isolated, compounds 1 [(2S,4S)-2,4-dihydroxyheptadec-16-enyl acetate] and 2 [(2S,4S)-2,4-dihydroxyheptadec-16-ynyl acetate]. In this study, we show for the first time that the growth inhibitory efficacy of this chloroform extract is due to blocking the phosphorylation of EGFR (Tyr1173), c-RAF (Ser338), and ERK1/2 (Thr202/Tyr204) in the EGFR/RAS/RAF/MEK/ERK1/2 cancer pathway. Compound 1 and 2 both inhibited phosphorylation of c-RAF (Ser338) and ERK1/2 (Thr202/Tyr204). Compound 2, but not compound 1, prevented EGF-induced activation of EGFR (Tyr1173). When compounds 1 and 2 were combined they synergistically inhibited c-RAF (Ser338) and ERK1/2 (Thr202/Tyr204) phosphorylation, and human oral cancer cell proliferation. The present data suggest that the potential anticancer activity of avocado fruits is due to a combination of specific aliphatic acetogenins that target two key components of the EGFR/RAS/RAF/MEK/ERK1/2 cancer pathway. PMID:21596018

  5. Anti-fungal activities of constituents from Uvaria scheffleri and Artabotrys brachypetalus

    Directory of Open Access Journals (Sweden)

    Odebode A.C.

    2006-01-01

    Full Text Available The anti-fungal activity of schefflone, a mixture of dimmer, 3,5 dimethoxy carvacrol and annonaceous acetogenin, extracted from stem-bark and root of Uvaria scheffleri and Artabotrys bruchypetalus against Fusarium solani, Botryodiplodia theobromae, Asperillus niger and Aspergillus flavus was determined. An in-vitro bioassay showed that the minimum inhibitory effect of the compounds to the fungal pathogens occurred at 200 ppm in both radial growth and mycelia dry weight measurements. Acetogenin from A brachypetalus had a very strong anti-fungal effect on all the test fungi. The effects of the compounds were more pronounced on F solani than on the other. The bioassay methods also play a significant role in the sensitivity of the samples on the pathogens. .

  6. New acetogenin peroxides from the Indian sponge Acarnus bicladotylota

    Digital Repository Service at National Institute of Oceanography (India)

    Fontana, A.; d'Ippolito, G.; DeSouza, L.; Mollo, E.; Parameswaran, P.S.; Cimino, G.

    on the basis of a parent ion in the CIMS (m/z 440 [M + NH 4 ] + ) consistent with the 13 C NMR data (Table 1). The 1 H NMR spectrum of 1a showed two well-defined double- doublets at 2.39 and 2.52 (H 2 -2) that were both coupled to the downshifted methine... conulose. The ectosomal skeleton showed a felt-work of tylotes (tylota head spined terminally), whereas the endosomal skeleton showed plumose bands of styles in thicker parts of the specimen and erect in encrusting parts. Spongin, pale yellow in color...

  7. Kaurenoic acid from pulp of Annona cherimolia in regard to Annonaceae-induced Parkinsonism.

    Science.gov (United States)

    Guillopé, R; Escobar-Khondiker, M; Guérineau, V; Laprévote, O; Höglinger, G U; Champy, P

    2011-12-01

    Guadeloupean Parkinsonism has been linked epidemiologically to the consumption of Annonaceae fruits. These were proposed to be etiological agents for sporadic atypical Parkinsonism worldwide, because of their content of neurotoxins such as isoquinolinic alkaloids and Annonaceous acetogenins. The pulp of Annona cherimolia Mill. from Spain was screened for these toxic molecules using Matrix-Assisted Laser Desorption Ionisation - Time of Flight mass spectrometry (MALDI-TOF MS) and it was found not to be a source of exposure. However, kaurenoic acid, a diterpene considered to be cytotoxic, was detected in high amounts (66 mg/fresh fruit). Treatment of rat embryonic striatal primary cultures, up to a high concentration (50 µM), did not cause neuronal death nor astrogliosis, suggesting that this molecule is not at risk of implication in human neurodegenerative diseases.

  8. Multiple Modes of Action of the Squamocin in the Midgut Cells of Aedes aegypti Larvae

    Science.gov (United States)

    de Paula, Sérgio Oliveira; Martins, Gustavo Ferreira; Zanuncio, José Cola

    2016-01-01

    Annonaceous acetogenins are botanical compounds with good potential for use as insecticides. In the vector, Aedes aegypti (L.) (Diptera: Culicidae), squamocin (acetogenin) has been reported to be a larvicide and cytotoxic, but the modes of action of this molecule are still poorly understood. This study evaluated the changes in the cell morphology, and in the expression of genes, for autophagy (Atg1 and Atg8), for membrane ion transporter V-ATPase, and for water channel aquaporin-4 (Aqp4) in the midgut of A. aegypti larvae exposed to squamocin from Annona mucosa Jacq. (Annonaceae). Squamocin showed cytotoxic action with changes in the midgut epithelium and digestive cells of A. aegypti larvae, increase in the expression for autophagy gene Atg1 and Atg8, decrease in the expression of V-ATPase, decrease in the expression of Aqp4 gene in LC20 and inhibition of Apq4 genes in the midgut of this vector in LC50. These multiple modes of action for squamocin are described for the first time in insects, and they are important because different sites of action of squamocin from A. mucosa may reduce the possibility of resistance of A. aegypti to this molecule. PMID:27532504

  9. Morphologie et palynologie des Annonacées africaines: interrelations phylogéniques

    Directory of Open Access Journals (Sweden)

    A. LE Thomas

    1983-12-01

    Full Text Available MORPHOLOGY AND PALYNOLOGY OF THE AFRICAN ANNONACEAE: PHYLOGENETICINTER-RELATIONS Taxonomy not only the practice of plant classification, but also a science of synthesis attempting to outline the possible stages followed by the evolution of a group. It attempts, therefore, to re-create and to explain the dynamics of the evolution of plants through the analysis of all their characters and of the relationships existing between them. Consequently, it can only benefit from the birth or development of all disciplines that analyse fresh aspects of plants or study them in time and space. For these reasons, palynology has developed considerably within taxonomy, revealing new morphological characters that permit a comparison with many fossil examples. In the family Annonaceae, of which the different classifications are admittedly artificial, pollen studies have shown that evolution is expressed in continuous morphological series along parallel lines. The established correlations with other morphological characters throw some light on certain phenomena of parallel evolution within the family, showing that the flower of the Annonaceae is in the process of reduction and the correlations contribute to a better knowledge of the affinities between generic taxa and their respective evolutionary levels.

  10. Annona muricata (Annonaceae): A Review of Its Traditional Uses, Isolated Acetogenins and Biological Activities

    OpenAIRE

    Soheil Zorofchian Moghadamtousi; Mehran Fadaeinasab; Sonia Nikzad; Gokula Mohan; Hapipah Mohd Ali; Habsah Abdul Kadir

    2015-01-01

    Annona muricata is a member of the Annonaceae family and is a fruit tree with a long history of traditional use. A. muricata, also known as soursop, graviola and guanabana, is an evergreen plant that is mostly distributed in tropical and subtropical regions of the world. The fruits of A. muricata are extensively used to prepare syrups, candies, beverages, ice creams and shakes. A wide array of ethnomedicinal activities is contributed to different parts of A. muricata, and indigenous communiti...

  11. Differential cytotoxic effects of Annona squamosa seed extracts on human tumour cell lines: Role of reactive oxygen species and glutathione

    Indian Academy of Sciences (India)

    B V V Pardhasaradhi; Madhurima Reddy; A Mubarak Ali; A Leela Kumari; Ashok Khar

    2005-03-01

    Annonaceous acetogenins are a new class of compounds that have been reported to have potent pesticidal, parasiticidal, anti-microbial, cell growth inhibitory activities. In this study, organic and aqueous extracts from the defatted seeds of Annona squamosa (custard apple) were tested on different human tumour cell lines for antitumoural activity. While organic and aqueous extracts induced apoptosis in MCF-7 and K-562 cells, they failed to do so in COLO-205 cells. Treatment of MCF-7 and K-562 cells with organic and aqueous extracts resulted in nuclear condensation, DNA fragmentation, induction of reactive oxygen species (ROS) generation and reduced intracellular glutathione levels. In addition downregulation of Bcl-2 and PS externalization by Annexin-V staining suggested induction of apoptosis in MCF-7 and K-562 cells by both the extracts through oxidative stress. On the contrary, COLO-205 cells showed only PS externalization but no change in ROS and glutathione levels. These observations suggest that the induction of apoptosis by A. squamosa extracts can be selective for certain types of cancerous cells.

  12. Desacetyluvaricin induces S phase arrest in SW480 colorectal cancer cells through superoxide overproduction.

    Science.gov (United States)

    Xue, Jun-Yi; Zhou, Guang-Xiong; Chen, Tianfeng; Gao, Si; Choi, Mei-Yuk; Wong, Yum-Shing

    2014-03-01

    Annonaceous acetogenins (ACGs) are a group of fatty acid-derivatives with potent anticancer effects. In the present study, we found desacetyluvaricin (Dau) exhibited notable in vitro antiproliferative effect on SW480 human colorectal carcinoma cells with IC50 value of 14 nM. The studies on the underlying mechanisms revealed that Dau inhibited the cancer cell growth through induction of S phase cell cycle arrest from 11.3% (control) to 33.2% (160 nM Dau), which was evidenced by the decreased protein expression of cyclin A Overproduction of superoxide, intracellular DNA damage, and inhibition of MEK/ERK signaling pathway, were also found involved in cells exposed to Dau. Moreover, pre-treatment of the cells with ascorbic acid significantly prevented the Dau-induced overproduction of superoxide, DNA damage and cell cycle arrest. Taken together, our results suggest that Dau induces S phase arrest in cancer cells by firstly superoxide overproduction and subsequently the involvement of various signaling pathways.

  13. Assessment of toxic potential of Cerrado fruit seeds using Artemia salina bioassay

    Directory of Open Access Journals (Sweden)

    Raíza Cavalcante Fonseca

    2013-06-01

    Full Text Available Artemia salina bioassay was used to assess toxicity of seeds and kernels of Brazilian fruits from cerrado (central high plains region and other inner regions of the country. Water extracts of the kernels were filtered and added to Artemia cultures containing ten individuals per mL. Dose - response curves were constructed, and LD50 values were calculated. Pure potassium cyanide standard was used to draw a calibration curve for comparison to detect the presence of cyanide in the samples tested. Extracts of the seeds of araticum, mangaba, cagaita, jatobá, and tucumã were found toxic to Artemia salina, and some of the dose - response curves were very similar in shape to those obtained with pure potassium cyanide standards, while the samples of baru, cajá-manga, siriguela, trauma, and veludo showed no toxicity at all. The Guignard test, specific for cyanide detection, showed negative results in all toxic samples, suggesting the presence of other toxic compounds rather than cyanide. The comparison of araticum dose - response curve with those of other annonaceous fruits suggests the presence acetogenins as the main toxic compounds in the seeds. These results could be useful to prevent poisoning by industrial derivatives of the fruits studied.

  14. Avaliação da atividade citotóxica das sementes de Annona cornifolia A. St.-Hil. (Annonaceae Evaluation of the cytotoxic activity of seeds of Annona cornifolia A. St.-Hil. (Annonaceae

    Directory of Open Access Journals (Sweden)

    L.A.R.S. Lima

    2012-01-01

    Full Text Available Na família Annonaceae, especialmente o gênero Annona é muito apreciado por fornecer frutos comestíveis. Espécies desse gênero são utilizadas na medicina popular contra diabetes, malária e infecções. Muitas dessas atividades biológicas têm sido relacionadas às acetogeninas de anonáceas. O objetivo deste estudo foi avaliar a atividade citotóxica dos grupos e de uma acetogenina pura (cornifolina obtidos a partir do extrato etanólico das sementes de Annona cornifolia A. St.-Hil. (Annonaceae. Esta atividade foi avaliada pelo ensaio colorimétrico MTT. Cornifolina (1, a única substância pura testada, apresentou citotoxicidade positiva sobre todas as linhagens tumorais avaliadas. Os grupos testados, todos caracterizados por espectroscopia no infravermelho (IV, apresentaram 68,7% dos valores de CI50 menores que 20,0 µg mL-1, sendo também considerados citotóxicos. As amostras testadas foram mais ativas que o taxol sobre melanoma humano (MeWo e, ainda, o grupo G10-5 apresentou melhor atividade sobre fibroblasto tumorigênico de camundongo (L929. Além disso, os grupos mostraram menor citotoxidade do que o taxol sobre a linhagem normal (CHO.The family Annonaceae, especially the genus Annona, is greatly appreciated for providing edible fruits. Species of this genus are used in folk medicine against diabetes, malaria and infections. Many of these biological activities have been related to annonaceous acetogenins. The aim of this study was to evaluate the cytotoxic activity of groups and a pure acetogenin (cornifolin obtained from the ethanol extract of the seeds of Annona cornifolia A. St.-Hil. (Annonaceae. This activity was evaluated by using MTT colorimetric assay. Cornifolin (1, the only tested substance that was pure, showed positive cytotoxicity on all evaluated tumor cell lines. The tested groups, all characterized by infrared spectroscopy (IR, showed 68.7% of the IC50 values lower than 20.0 µg mL-1, also considered cytotoxic. The

  15. Squamocin modulates histone H3 phosphorylation levels and induces G1 phase arrest and apoptosis in cancer cells

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    Wu Yang-Chang

    2011-02-01

    Full Text Available Abstract Background Histone modifications in tumorigenesis are increasingly recognized as important epigenetic factors leading to cancer. Increased phosphorylation levels of histone H3 as a result of aurora B and pMSK1 overexpression were observed in various tumors. We selected aurora B and MSK1 as representatives for testing various compounds and drugs, and found that squamocin, a bis-tetrahydrofuran annonaceous acetogenin, exerted a potent effect on histone H3 phosphorylation. Methods GBM8401, Huh-7, and SW620 cells were incubated with 15, 30, and 60 μM squamocin for 24 h. The expressions of mRNA and proteins were analyzed by qRT-PCR and Western blotting, respectively. The cell viability was determined by an MTT assay. Cell cycle distribution and apoptotic cells were analyzed by flow cytometry. Results Our results showed that squamocin inhibited the proliferation of GBM8401, Huh-7, and SW620 cells, arrested the cell cycle at the G1 phase, and activated both intrinsic and extrinsic pathways to apoptosis. In addition, we demonstrated that squamocin had the ability to modulate the phosphorylation levels of H3S10 (H3S10p and H3S28 (H3S28p in association with the downregulation of aurora B and pMSK1 expressions. Conclusions This study is the first to show that squamocin affects epigenetic alterations by modulating histone H3 phosphorylation at S10 and S28, providing a novel view of the antitumor mechanism of squamocin.

  16. The chemopotential effect of Annona muricata leaves against azoxymethane-induced colonic aberrant crypt foci in rats and the apoptotic effect of Acetogenin Annomuricin E in HT-29 cells: a bioassay-guided approach.

    Science.gov (United States)

    Zorofchian Moghadamtousi, Soheil; Rouhollahi, Elham; Karimian, Hamed; Fadaeinasab, Mehran; Firoozinia, Mohammad; Ameen Abdulla, Mahmood; Abdul Kadir, Habsah

    2015-01-01

    Annona muricata has been used in folk medicine for the treatment of cancer and tumors. This study evaluated the chemopreventive properties of an ethyl acetate extract of A. muricata leaves (EEAML) on azoxymethane-induced colonic aberrant crypt foci (ACF) in rats. Moreover, the cytotoxic compound of EEAML (Annomuricin E) was isolated, and its apoptosis-inducing effect was investigated against HT-29 colon cancer cell line using a bioassay-guided approach. This experiment was performed on five groups of rats: negative control, cancer control, EEAML (250 mg/kg), EEAML (500 mg/kg) and positive control (5-fluorouracil). Methylene blue staining of colorectal specimens showed that application of EEAML at both doses significantly reduced the colonic ACF formation compared with the cancer control group. Immunohistochemistry analysis showed the down-regulation of PCNA and Bcl-2 proteins and the up-regulation of Bax protein after administration of EEAML compared with the cancer control group. In addition, an increase in the levels of enzymatic antioxidants and a decrease in the malondialdehyde level of the colon tissue homogenates were observed, suggesting the suppression of lipid peroxidation. Annomuricin E inhibited the growth of HT-29 cells with an IC50 value of 1.62 ± 0.24 μg/ml after 48 h. The cytotoxic effect of annomuricin E was further substantiated by G1 cell cycle arrest and early apoptosis induction in HT-29 cells. Annomuricin E triggered mitochondria-initiated events, including the dissipation of the mitochondrial membrane potential and the leakage of cytochrome c from the mitochondria. Prior to these events, annomuricin E activated caspase 3/7 and caspase 9. Upstream, annomuricin E induced a time-dependent upregulation of Bax and downregulation of Bcl-2 at the mRNA and protein levels. In conclusion, these findings substantiate the usage of A. muricata leaves in ethnomedicine against cancer and highlight annomuricin E as one of the contributing compounds in the anticancer activity of A. muricata leaves.

  17. The chemopotential effect of Annona muricata leaves against azoxymethane-induced colonic aberrant crypt foci in rats and the apoptotic effect of Acetogenin Annomuricin E in HT-29 cells: a bioassay-guided approach.

    Directory of Open Access Journals (Sweden)

    Soheil Zorofchian Moghadamtousi

    Full Text Available Annona muricata has been used in folk medicine for the treatment of cancer and tumors. This study evaluated the chemopreventive properties of an ethyl acetate extract of A. muricata leaves (EEAML on azoxymethane-induced colonic aberrant crypt foci (ACF in rats. Moreover, the cytotoxic compound of EEAML (Annomuricin E was isolated, and its apoptosis-inducing effect was investigated against HT-29 colon cancer cell line using a bioassay-guided approach. This experiment was performed on five groups of rats: negative control, cancer control, EEAML (250 mg/kg, EEAML (500 mg/kg and positive control (5-fluorouracil. Methylene blue staining of colorectal specimens showed that application of EEAML at both doses significantly reduced the colonic ACF formation compared with the cancer control group. Immunohistochemistry analysis showed the down-regulation of PCNA and Bcl-2 proteins and the up-regulation of Bax protein after administration of EEAML compared with the cancer control group. In addition, an increase in the levels of enzymatic antioxidants and a decrease in the malondialdehyde level of the colon tissue homogenates were observed, suggesting the suppression of lipid peroxidation. Annomuricin E inhibited the growth of HT-29 cells with an IC50 value of 1.62 ± 0.24 μg/ml after 48 h. The cytotoxic effect of annomuricin E was further substantiated by G1 cell cycle arrest and early apoptosis induction in HT-29 cells. Annomuricin E triggered mitochondria-initiated events, including the dissipation of the mitochondrial membrane potential and the leakage of cytochrome c from the mitochondria. Prior to these events, annomuricin E activated caspase 3/7 and caspase 9. Upstream, annomuricin E induced a time-dependent upregulation of Bax and downregulation of Bcl-2 at the mRNA and protein levels. In conclusion, these findings substantiate the usage of A. muricata leaves in ethnomedicine against cancer and highlight annomuricin E as one of the contributing compounds in the anticancer activity of A. muricata leaves.

  18. In vitro sensitivity of Plasmodium falciparum field isolates to extracts from Cameroonian Annonaceae plants.

    Science.gov (United States)

    Kemgne, Eugénie Aimée Madiesse; Mbacham, Wilfred Fon; Boyom, Fabrice Fekam; Zollo, Paul Henri Amvam; Tsamo, Etienne; Rosenthal, Philip J

    2012-01-01

    In a search for new plant-derived antimalarial extracts, 19 fractions were obtained from three Annonaceae species, Uvariopsis congolana (leaf, stem), Polyalthia oliveri (stem bark), and Enantia chlorantha (stem, stem bark) with yields ranging from 0.33% to 4.60%. The extracts were prepared from 500 g of each plant part, using organic solvents to afford five methanolic fractions (acetogenin rich), five water fractions, five hexane fractions, and four interface precipitates. Evaluation of the activity of fractions in vitro against field isolates of the malaria parasite Plasmodium falciparum showed that acetogenin-rich fractions and interface precipitates were the most potent, with IC(50) values ranging from 0.05 to 8.09 μg/ml. Sensitivity of parasite isolates to plant extracts varied greatly, with over 100-fold difference from isolate to isolate in some cases. The active acetogenin-rich fractions and interface precipitates were assessed in combination with chloroquine in the same conditions, and showed additive interaction in the huge majority of cases. Synergistic interactions were found in some cases with acetogenin-rich fractions. Acute toxicity of promising fractions was evaluated through oral administration in Swiss albino mice. Tested fractions appeared to be safe, with LD(50) values higher than 2 g/kg. In summary, acetogenin-rich fractions from Annonaceae species showed high potency against P. falciparum field isolates and safety by oral administration in mice, supporting their detailed investigation for antimalarial drug discovery.

  19. Studies in Annonaceae XXXII. A peculiar new species of Malmea (Annonaceae) from Panama and Colobia

    NARCIS (Netherlands)

    Chatrou, L.W.

    1997-01-01

    In the framework of the multidisciplinary Annonaceae Project, a monograph of the neotropical genus Malmea is being prepared by the author. A new species of Malmea with dimerous flowers, exceptional for Annonaceae, is here described. An overview of deviations from the typical trimerous annonaceous pe

  20. Acetogeninas de anonáceas isoladas de folhas de Rollinia laurifolia

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    Nascimento Francisco das Chagas do

    2003-01-01

    Full Text Available Phytochemical investigation of hexanic extract of leaves of Rollinia laurifolia afforded three known acetogenins, uvariamicin-I (1, solamin(2 and gonionenin(3, for the first time isolated from Rollinia genus. The structures of 1, 2 and 3 were elucidated by spectroscopic methods.

  1. Antiparasitic activity of Annona muricata and Annona cherimolia seeds.

    Science.gov (United States)

    Bories, C; Loiseau, P; Cortes, D; Myint, S H; Hocquemiller, R; Gayral, P; Cavé, A; Laurens, A

    1991-10-01

    Methanolic extracts of Annona muricata and A. cherimolia (Annonaceae) seeds were tested for antiparasitic activity against E. histolytica, N. brasiliensis, M. dessetae and A. salina. The acetogenins isolated from these extracts are found to be responsible for the important activity on infective larvae of Molinema desetae.

  2. Cytotoxicity and antileishmanial activity of Annona muricata pericarp.

    Science.gov (United States)

    Jaramillo, M C; Arango, G J; González, M C; Robledo, S M; Velez, I D

    2000-04-01

    Hexane, ethyl acetate and methanol extracts of Annona muricata pericarp were tested in vitro against Leishmania braziliensis and L. panamensis promastigotes, and against cell line U-937. The ethyl acetate extract was more active than the other extracts and even of Glucantime used as reference substance. Its fractionation led to the isolation of three acetogenins--annonacin, annonacin A and annomuricin A.

  3. Leishmanicidal activity and cytotoxicity of compounds from two Annonacea species cultivated in Northeastern Brazil

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    Nadja Soares Vila-Nova

    2011-10-01

    Full Text Available INTRODUCTION: Visceral leishmaniasis is endemic in 88 countries, with a total of 12 million people infected and 350 million at risk. In the search for new leishmanicidal agents, alkaloids and acetogenins isolated from leaves of Annona squamosa and seeds of Annona muricata were tested against promastigote and amastigote forms of Leishmania chagasi. METHODS: Methanol-water (80:20 extracts of A. squamosa leaves and A. muricata seeds were extracted with 10% phosphoric acid and organic solvents to obtain the alkaloid and acetogenin-rich extracts. These extracts were chromatographed on a silica gel column and eluted with a mixture of several solvents in crescent order of polarity. The compounds were identified by spectroscopic analysis. The isolated compounds were tested against Leishmania chagasi, which is responsible for American visceral leishmaniasis, using the MTT test assay. The cytotoxicity assay was evaluated for all isolated compounds, and for this assay, RAW 264.7 cells were used. RESULTS: O-methylarmepavine, a benzylisoquinolinic alkaloid, and a C37 trihydroxy adjacent bistetrahydrofuran acetogenin were isolated from A. squamosa, while two acetogenins, annonacinone and corossolone, were isolated from A. muricata. Against promastigotes, the alkaloid showed an IC50 of 23.3 µg/mL, and the acetogenins showed an IC50 ranging from 25.9 to 37.6 µg/mL; in the amastigote assay, the IC50 values ranged from 13.5 to 28.7 µg/mL. The cytotoxicity assay showed results ranging from 43.5 to 79.9 µg/mL. CONCLUSIONS: These results characterize A. squamosa and A. muricata as potential sources of leishmanicidal agents. Plants from Annonaceae are rich sources of natural compounds and an important tool in the search for new leishmanicidal therapies.

  4. Evaluation of cytotoxicity of aqueous extract of Graviola leaves on squamous cell carcinoma cell-25 cell lines by 3-(4,5-dimethylthiazol-2-Yl) -2,5-diphenyltetrazolium bromide assay and determination of percentage of cell inhibition at G2M phase of cell cycle by flow cytometry: An in vitro study

    OpenAIRE

    Visveswaraiah Paranjyothi Magadi; Venkatadasappa Ravi; Anantharaju Arpitha; Litha; Kikkerilakshminarayana Kumaraswamy; Krishnappa Manjunath

    2015-01-01

    Introduction: Malignancies constitute a wide variety of disorders having high mortality and morbidity rates. Current protocols for management include surgical intervention, chemotherapy, and radiation which possess numerous adverse effects. Many phytochemicals are available with anticancer properties similar to anticancer drugs. Major benefit of these compounds is apparent lack of toxicity to normal tissues. Graviola (botanical name: Annona Muricata) contain bioactive compound “annonaceous ac...

  5. Isolation and chemical identification of lipid derivatives from avocado (Persea americana) pulp with antiplatelet and antithrombotic activities.

    Science.gov (United States)

    Rodriguez-Sanchez, Dariana Graciela; Flores-García, Mirthala; Silva-Platas, Christian; Rizzo, Sheryl; Torre-Amione, Guillermo; De la Peña-Diaz, Aurora; Hernández-Brenes, Carmen; García-Rivas, Gerardo

    2015-01-01

    Platelets play a pivotal role in physiological hemostasis. However, in coronary arteries damaged by atherosclerosis, enhanced platelet aggregation, with subsequent thrombus formation, is a precipitating factor in acute ischemic events. Avocado pulp (Persea americana) is a good source of bioactive compounds, and its inclusion in the diet as a source of fatty acid has been related to reduced platelet aggregability. Nevertheless, constituents of avocado pulp with antiplatelet activity remain unknown. The present study aims to characterize the chemical nature of avocado constituents with inhibitory effects on platelet aggregation. Centrifugal partition chromatography (CPC) was used as a fractionation and purification tool, guided by an in vitro adenosine diphosphate (ADP), arachidonic acid or collagen-platelet aggregation assay. Antiplatelet activity was initially linked to seven acetogenins that were further purified, and their dose-dependent effects in the presence of various agonists were contrasted. This process led to the identification of Persenone-C (3) as the most potent antiplatelet acetogenin (IC₅₀=3.4 mM) among the evaluated compounds. In vivo evaluations with Persenone A (4) demonstrated potential protective effects against arterial thrombosis (25 mg kg⁻¹ of body weight), as coagulation times increased (2-fold with respect to the vehicle) and thrombus formation was attenuated (71% versus vehicle). From these results, avocado may be referred to as a functional food containing acetogenin compounds that inhibit platelet aggregation with a potential preventive effect on thrombus formation, such as those that occur in ischaemic diseases.

  6. Neurotoxicity of Dietary Supplements from Annonaceae Species.

    Science.gov (United States)

    Höllerhage, Matthias; Rösler, Thomas W; Berjas, Magda; Luo, Rensheng; Tran, Kevin; Richards, Kristy M; Sabaa-Srur, Armando U; Maia, José Guilherme S; Moraes, Maria Rosa de; Godoy, Helena T; Höglinger, Günter U; Smith, Robert E

    2015-01-01

    Dietary supplements containing plant materials of Annonaceae species (Annona muricata L., A. squamosa L., A. mucosa JACQ., A. squamosa × cherimola Mabb.) were extracted by hot, pressurized ethyl acetate and analyzed for their effect in vitro on Lund human mesencephalic neurons. Cell viability was measured by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay, and cell death was determined by lactate dehydrogenase levels. Three supplements strongly decreased the cell viability at extract concentrations of 1 µg/mL, of which 1 decreased cell viability at 0.1 µg/µL. Also, strong neuronal toxicities of these supplements were found. Cell death was observed at concentrations of 10 µg/mL. The degree of toxicity was comparable to the ones found in Annonaceous fruit extracts. Two fruit pulps of Annonaceae (A. muricata and A. squamosa) showed a reduction in cell viability at lower concentrations. The fruit pulp extract of A. muricata revealed the strongest neurotoxic effect, with 67% cell death at a concentration of 1 µg/mL. A high reduction in cell viability coupled with pronounced cell death was found at 0.1 µg/mL for an Annonaceous seed extract. These results demonstrate that the intake of dietary supplements containing plant material from Annonaceae may be hazardous to health in terms of neurotoxicity.

  7. Goniothalamus: Phytochemical and Ethnobotanical Review

    Directory of Open Access Journals (Sweden)

    Muhammad Shahzad Aslam

    2016-07-01

    Full Text Available Goniothalamus species are used in widespread medicines to cause abortion, antiaging, body pains, rheumatism, skin complaints, typhoid fever, tympanites, stomach ache and fever. The present study reviews the distribution of species along with their synonyms, their traditional usage, and correlated chemical compounds of Goniothalamus species with stress on the authentication of their ethnobotanical uses. The findings in some Goniothalamus species suggest that the chemical nature of their derivatives, such as acetogenins and styryl lactones, may justify the uses of these species against cancer in Asian traditional medicines due to their cytotoxic potential.

  8. NOTES ON NEW GUINEA PLANTS—IV* Saccopetalum koolsii Kostermans, sp. nov. (Annonaceae

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    A. J. G. H. KOSTERMANS

    2015-11-01

    Full Text Available During the exploration of the Momi-Ransiki region, about 80 km south of Manokwari on the west coast of the Geelvink Bay in Netherlands New Guinea in 1948, our party collected several specimens of a rather common, although scattered Annonaceous tree, which was locally called mies (pronounce: meece. I was lucky to find one tree in flower in the neighbourhood of the Warnapi (war = river, north of Ransiki. After examination the species appeared to belong to the genus Saccopetalum Benn., hitherto unknown from New Guinea. In honour of Dr. J. Kools,'at that time in charge of the Division of Planning (nowadays Professor at the State Agricultural University of Wageningen, The Netherlands, who took a lively interest in the exploration of this area, this species is called

  9. Notes on the floral anatomy of Deeringothamnus Small (Annonaceae: cortical vascular systems in a chaotic pattern

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    Thierry Deroin

    2016-06-01

    Full Text Available Floral anatomy of Deeringothamnus Small, an endemic and endangered annonaceous genus from Florida comprising 2 species, was studied. It is mainly distinguished by missing any sclerenchyma at anthesis – apart from anthers – and by a chaotic vasculature exhibiting a partial perianth-stamen cortical vascular system, appearing as an over-evolution of the pattern previously described in the neighbouring Asimina and other paracarpous and pseudosyncarpous genera. Such a pattern is amazingly similar to that previously recognized in the most basal annonaceaous genera, as e.g. Ambavia, and might be considered as a reversion to an ancestral state. These alterations toward decrease are related to the receptacle flatness and lack of pollination chamber, and seem parallel with the dwarf habit of this genus.

  10. Tryptamine-derived alkaloids from Annonaceae exerting neurotrophin-like properties on primary dopaminergic neurons.

    Science.gov (United States)

    Schmidt, Fanny; Le Douaron, Gael; Champy, Pierre; Amar, Majid; Séon-Méniel, Blandine; Raisman-Vozari, Rita; Figadère, Bruno

    2010-07-15

    N-fatty acyl tryptamines constitute a scarce group of natural compounds mainly encountered in Annonaceous plants. No biological activity was reported so far for these rare molecules. This study investigated the neurotrophic properties of these natural tryptaminic derivatives on dopaminergic (DA) neurons in primary mesencephalic cultures. A structure-activity relationships study led us to precise the role of a nitrogen atom into the aliphatic chain conferring to the compounds a combined neuroprotective and neuritogenic activity in the nanomolar range. The potent antioxidant activity of these natural products seems to be involved in part of their mechanism of action. This study provides the first description of natural neurotrophin mimetics present in Annonaceae extracts, and led to the biological characterization of compounds, which present a potential interest in neurodegenerative diseases such as Parkinson's disease.

  11. FIRST REPORT OF Phytophthora nicotianae CAUSING ROOT ROT OF SOURSOP IN NORTHEASTERN BRAZIL

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    JAQUELINE FIGUEREDO DE OLIVEIRA COSTA

    Full Text Available ABSTRACT In 2013, soursop trees showing symptoms of root rot were observed in a field in Maceió, state of Alagoas, Brazil. It was isolated Phytophthora sp. which pathogenicity was confirmed in the host seedlings. Morphological and physiological characteristics in carrot-agar modified medium were consistent with Phytophthora nicotianae description. The PCR sequences products obtained with ITS1/ITS4 primers were compared to sequences of ribosomal DNA of Phytophthora species from the GenBank database observing high identity with other P. nicotianae isolates. A phylogenetic tree was performed to compare the isolate with other sequences of P. nicotianae, which clustering has been verified with 99% of bootstrap, confirming the morphophysiological studies. This is the first report of this pathogen on annonaceous plants in the Northeastern Brazil.

  12. Antibacterial activity of eight Brazilian annonaceae plants.

    Science.gov (United States)

    Takahashi, Jacqueline A; Pereira, Cássia R; Pimenta, Lúcia P S; Boaventura, Maria Amélia D; Silva, Luiz G F E

    2006-01-01

    Sixteen extracts, obtained from eight Brazilian plants of Annonaceae family, were screened for their antibacterial activity: Xylopia frutescens, X. aromatica, X. amazonica, X. benthamii, Annona ambotay, A. crassiflora, A. muricata and A. cherimolia. Amongst the investigated extracts, six showed antibacterial activity against at least one of the tested organisms at the concentration of 100 microg/mL. The most active extracts were those prepared from X. frutescens, X. amazonica, and A. ambotay. A phytochemical screening showed the presence of anonaceus acetogenins in some active extracts. Eleven diterpenoids were also tested for comparison purposes. Six were natural products, previously isolated from Xylopia sp. (kaurenoic, frutoic, xylopic, 15beta-hydroxy-kaurenoic and trachylobanic acids plus kaurenol) and five were derivatives of such compounds, obtained by esterification or reduction reactions. Trachylobanic acid showed antibacterial activity against B. subtilis and S. aureus.

  13. Advances in research of cytotoxic chemical constituents of Annonaceae plants%番荔枝科植物细胞毒成分的研究概况Ⅷ

    Institute of Scientific and Technical Information of China (English)

    顾关云; 蒋昱

    2010-01-01

    番荔枝科植物固其特异性成分乙酰精宁(acetogenins)具有低毒、高效、广谱的生物活性和药理作用而备受关注,且该科植物资源十分丰富.续报近年来番荔枝科植物细胞毒成分的研究概况,介绍番荔枝属、依兰属、哥纳香属、野独活属、暗罗属、紫玉盘属、木瓣属等30余种植物的具细胞毒活性的乙酰精宁、苯乙烯内酯等化学成分及其药理活性研究进展.

  14. Plant latex: A natural source of pharmaceuticals and pesticides

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    Ravi K Upadhyay

    2011-01-01

    Full Text Available In recent times use of plant natural products has increased tremendously, and there is a very high demand of herbal products for therapeutic, clinical, agricultural purposes. Plant latex is a rich source of pharmaceuticals, pesticides and immune allergens. It also contains important biomolecules such as glycosides, tannins, phytosterols, Flavonoids, acetogenins and saponins, which show diverse biolgical activities against bacteria, fungi, viruses, protozoans, nematodes, insects, and cancer and tumours. It is also used as disinfectant, anticoagulant, anti-inflammatory, antioxidant and antiproliferative agent that provides protection in wounds. It contains wide variety of industrially important metabolic substances which can be harvested, modified, quenched, and polymerized easily for making goods and materials by up-gradation of technology. No doubt it is a future raw material for many bioengineering and biotechnological industries.

  15. Bryophytes: liverworts, mosses, and hornworts: extraction and isolation procedures.

    Science.gov (United States)

    Asakawa, Yoshinori; Ludwiczuk, Agnieszka

    2013-01-01

    There are more than 20,000 species of bryophytes in the world. Among them, almost of liverworts (Marchantiophyta) possess beautiful blue, yellow colored or colorless cellular oil bodies from which over several hundred new terpenoids, acetogenins, and aromatic compounds including flavonoids with more than 40 new carbon skeletons have been isolated. Some of the isolated compounds from liverworts show antimicrobial, antifungal, antiviral, allergenic contact dermatitis, cytotoxicity, insect antifeedant and mortality, antioxidant, nitric oxide (NO) production and plant growth inhibitory, neurotrophic and piscicidal activity, tublin polymerization inhibitory, muscle relaxing, and liver X-receptor (LXR)α agonist and (LXR)β antagonist activities, among others. The bio- and chemical diversity, chemical analysis of bryophytes including extraction, distillation, purification, TLC, GC and GC-MS, and HPLC analysis of oil bodies of liverworts are surveyed.

  16. Phytochemical and biological studies of bryophytes.

    Science.gov (United States)

    Asakawa, Yoshinori; Ludwiczuk, Agnieszka; Nagashima, Fumihiro

    2013-07-01

    The bryophytes contain the Marchantiophyta (liverworts), Bryophyta (mosses) and Anthocerotophyta (hornworts). Of these, the Marchantiophyta have a cellular oil body which produce a number of mono-, sesqui- and di-terpenoids, aromatic compounds like bibenzyl, bis-bibenzyls and acetogenins. Most sesqui- and di-terpenoids obtained from liverworts are enantiomers of those found in higher plants. Many of these compounds display a characteristic odor, and can have interesting biological activities. These include: allergenic contact dermatitis, antimicrobial, antifungal and antiviral, cytotoxic, insecticidal, insect antifeedant, superoxide anion radical release, 5-lipoxygenase, calmodulin, hyaluronidase, cyclooxygenase, DNA polymerase β, and α-glucosidase and NO production inhibitory, antioxidant, piscicidal, neurotrophic and muscle relaxing activities among others. Each liverwort biosynthesizes unique components, which are valuable for their chemotaxonomic classification. Typical chemical structures and biological activity of the selected liverwort constituents as well as the hemi- and total synthesis of some biologically active compounds are summarized.

  17. Soursop Leaves (Annona muricata Folium on Mice (Mus musculus Fetus

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    Yunita Suryani

    2014-02-01

    Full Text Available Background: Soursop leaf ethanol extract (Annona muricata (L Folium contains acetogenins which are cytotoxic and have the ability to halt cell growth. This study aimed to understand whether acetogenins have teratogenic effects on mice fetus (Mus musculus. Methods: This study was performed at the Pharmacology and Therapy Laboratory of the Faculty of Medicine, Universitas Padjadjaran, Bandung, between October and November 2012. The study was an experimental laboratory study utilizing 27 pregnant mice which were divided into 3 groups. The first group was the negative control, the second was given soursop leaf ethanol extract at pre-implantation phase (day 1 to 5 and the third had the extract provided in the organogenesis phase (day 6 to 15. Laparotomy was performed on the 19th day of pregnancy. The parameters used were the number of implantation, the number of live and dead or resorbed fetus, the weight and length of the fetus, as well as the macroscopic external morphology abnormalities. The data gained from test subjects were compared to those of the control group. The statistical test used was the normality tes with the Kolmogorov-Smirnov method which was then followed by T-test or Mann-Whitney statistical tests. Results: The experiment exhibited significant differences in the weight and length of the fetus (p-value 0.000, proving that soursop leaf ethanol extract could inhibit intrauterine growth. Aside from that, external morphological abnormalities such as hemorrhage on the head, face, neck, back, forelimbs, hindlimbs, and microcephaly were also found. Conclusion: The soursop leaf ethanol extract (Annona muricata (L Folium has a teratogenic effect on mouse (Mus musculus fetus. [AMJ.2014;1(1:48–53

  18. 番荔枝果皮提取物对HL60肿瘤细胞的抑制作用

    Institute of Scientific and Technical Information of China (English)

    张文生; 聂云

    2009-01-01

    番荔枝(A Squamosa Linn)属番荔枝科番荔枝属植物,又称林檎、释迦果,俗称甜荔枝、甜果。我国数省均有种植,尤以海南、广东和福建等省有较大面积的引种栽培。从番荔枝科(Annonaceae)植物中分离得到的大多数番荔枝内脂(Annonaceous acetogenins)类化合物具有很强的抗肿瘤作用,且抗瘤谱广。已有研究证明,番荔枝果皮提取物对S180肿瘤细胞具有一定的抑制作用,为了验证其对早幼粒白血病细胞(Hk)是否也具有抗癌活性,我们进行了如下实验。

  19. Plants of the Annonaceae traditionally used as antimalarials: a review

    Directory of Open Access Journals (Sweden)

    Gina Frausin

    2014-01-01

    Full Text Available Species of the Annonaceae family are used all over the tropics in traditional medicine in tropical regions for the treatment of malaria and other illnesses. Phytochemical studies of this family have revealed chemical components which could offer new alternatives for the treatment and control of malaria. Searches in scientific reference sites (SciFinder Scholar, Scielo, PubMed, ScienceDirect and ISI Web of Science and a bibliographic literature search for species of Annonaceae used traditionally to treat malaria and fever were carried out. This family contains 2,100 species in 123 genera. We encountered 113 articles reporting medicinal use of one or more species of this family including 63 species in 27 genera with uses as antimalarials and febrifuges. Even though the same species of Annonaceae are used by diverse ethnic groups, different plant parts are often chosen for applications, and diverse methods of preparation and treatment are used. The ethanol extracts of Polyalthia debilis and Xylopia aromatica proved to be quite active against Plasmodium falciparum in vitro (median inhibition concentration, IC50 < 1.5 µg/mL. Intraperitoneal injection of Annickia chlorantha aqueous extracts (cited as Enantia chlorantha cleared chloroquine-resistant Plasmodium yoelii nigeriensis from the blood of mice in a dose-dependant manner. More phytochemical profiles of Annonaceous species are required; especially information on the more commonly distributed antimalarial compounds in this family.

  20. Anti cancer activity on Graviola, an exciting medicinal plant extract vs various cancer cell lines and a detailed computational study on its potent anti-cancerous leads.

    Science.gov (United States)

    Paul, Jeno; Gnanam, R; Jayadeepa, R M; Arul, L

    2013-01-01

    Nature is the world's best chemist: Many naturally occurring compounds have very complicated structures that present great challenges to chemists wishing to determine their structures or replicate them. The plant derived herbal compounds have a long history of clinical use, better patient tolerance and acceptance. Their high ligand binding affinity to the target introduce the prospect of their use in chemo preventive applications; in addition they are freely available natural compounds that can be safely used to prevent various ailments. Plants became the basis of traditional medicine system throughout the world for thousands of years and continue to provide mankind with new remedies. Here, we present a research study on a medicinal plant, Graviola, a native of North America but rarely grown in India. It has a wide potent anticancerous agents coined as Acetogenins which play a key role towards many varieties of cancer, Acetogenins are potent inhibitors of NADH oxidase of the plasma membranes of cancer cells. Potent leads were taken for the study through literature survey, major types of cancer targets were identified, the natureceuticals and the cancer protein were subjected to docking analysis, further with the help of the dock score and other descriptor properties top ranked molecules were collected, commercial drug was also selected and identified as a Test compound for the study. Later, the phytochemicals were subjected to toxicity analysis. Those screened compounds were then considered for active site analysis and to find the best binding site for the study. R Programming library was used to find the best leads. Phytochemicals such as Anonaine, Friedelin, Isolaureline, Annonamine, Anomurine, Kaempferol, Asimilobine, Quercetin, Xylopine were clustered and the highly clustered compounds such as Annonamine , Kaempferol termed to be a potential lead for the study. Further study on experimental analysis may prove the potentiality of these compounds. In the

  1. Isolation and structure elucidation of avocado seed (Persea americana) lipid derivatives that inhibit Clostridium sporogenes endospore germination.

    Science.gov (United States)

    Rodríguez-Sánchez, Dariana Graciela; Pacheco, Adriana; García-Cruz, María Isabel; Gutiérrez-Uribe, Janet Alejandra; Benavides-Lozano, Jorge Alejandro; Hernández-Brenes, Carmen

    2013-07-31

    Avocado fruit extracts are known to exhibit antimicrobial properties. However, the effects on bacterial endospores and the identity of antimicrobial compounds have not been fully elucidated. In this study, avocado seed extracts were tested against Clostridium sporogenes vegetative cells and active endospores. Bioassay-guided purification of a crude extract based on inhibitory properties linked antimicrobial action to six lipid derivatives from the family of acetogenin compounds. Two new structures and four compounds known to exist in nature were identified as responsible for the activity. Structurally, most potent molecules shared features of an acetyl moiety and a trans-enone group. All extracts produced inhibition zones on vegetative cells and active endospores. Minimum inhibitory concentrations (MIC) of isolated molecules ranged from 7.8 to 15.6 μg/mL, and bactericidal effects were observed for an enriched fraction at 19.5 μg/mL. Identified molecules showed potential as natural alternatives to additives and antibiotics used by the food and pharmaceutical industries to inhibit Gram-positive spore-forming bacteria.

  2. Polyketide Derivatives from Annona muricata Linn Leaves as Potencial Anticancer Material by Combination Treatment With Doxorubicin on Hela Cell Line

    Science.gov (United States)

    Artanti, A. N.; Astirin, O. P.; Prayito, A.; Widiyaningsih, R. F.; Prihapsara, F.

    2017-02-01

    One of the compounds found effication as an anticancer agent on cervical cancer is acetogenin, a polyketide compound that is abundant in Annona muricata L. leaves. This study has been done to examine polyketide derivatives was isolated from Annona muricata L. which has potency to induce apoptosis by p53 expression on hela cell line. An approach recently develop to overcome side effect of chemoterapeutic agent is used of combined chemoterapeutic agent, i.e doxorubicin. The determination of cytotoxic combination activity from polyketide derivative and doxorubicin was evaluated using MTT assay to obtain the value of CI (combination index). The expression of p53 profile was evaluated by immunohistochemistry on hela cell line. Data analysis showed that combination of polyketide derivative from Annona muricata L. (38,5 µg/ml) and doxorubicin with all of concentration performed synergistic effect on hela cell line with CI value from 0,33 – 0,65. The analysis on immucytochemistry showed that polyketide derivative from Annona muricata L. leaves could enhance p53 pathway significantly on hela cell line.

  3. Antibacterial activity of halophilic bacterial bionts from marine invertebrates of Mandapam-India

    Directory of Open Access Journals (Sweden)

    Sheryanne Velho-Pereira

    2012-01-01

    Full Text Available Marine ecosystem and its organisms, particularly the invertebrates are recent targets of bioprospecting and mining for a large group of structurally unique natural products encompassing a wide variety of chemical classes such as terpenes, polyketides, acetogenins, peptides and alkaloids of varying structures, having pronounced pharmacological activities. In view of the limited reports on the antibacterials produced by bacteria, isolated from marine sponges, corals and bivalves of Indian origin, the present study is aimed at investigating the antagonistic activities of 100 heterotrophic, halophilic bacterial bionts isolated from 9 sponges, 5 corals and one bivalve. Culture broths of 46 of these bionts were active against human pathogenic bacteria namely Staphylococcus citreus, Proteus vulgaris, Serratio marcesans, Salmonella typhi, Aerobacter aerogenes and Escherichia coli. Further, the ethyl acetate extracts of cell free supernatant confirmed the presence of extracellular bioactive factor, by agar cup diffusion method. Interestingly, highest number of bionts having activity was isolated from corals followed by sponges and bivalve. The study clearly demonstrates that bacterial bionts of marine invertebrates are a rich source of bioactive secondary metabolites against human bacterial pathogens.

  4. Graviola inhibits hypoxia-induced NADPH oxidase activity in prostate cancer cells reducing their proliferation and clonogenicity.

    Science.gov (United States)

    Deep, Gagan; Kumar, Rahul; Jain, Anil K; Dhar, Deepanshi; Panigrahi, Gati K; Hussain, Anowar; Agarwal, Chapla; El-Elimat, Tamam; Sica, Vincent P; Oberlies, Nicholas H; Agarwal, Rajesh

    2016-03-16

    Prostate cancer (PCa) is the leading malignancy among men. Importantly, this disease is mostly diagnosed at early stages offering a unique chemoprevention opportunity. Therefore, there is an urgent need to identify and target signaling molecules with higher expression/activity in prostate tumors and play critical role in PCa growth and progression. Here we report that NADPH oxidase (NOX) expression is directly associated with PCa progression in TRAMP mice, suggesting NOX as a potential chemoprevention target in controlling PCa. Accordingly, we assessed whether NOX activity in PCa cells could be inhibited by Graviola pulp extract (GPE) that contains unique acetogenins with strong anti-cancer effects. GPE (1-5 μg/ml) treatment strongly inhibited the hypoxia-induced NOX activity in PCa cells (LNCaP, 22Rv1 and PC3) associated with a decrease in the expression of NOX catalytic and regulatory sub-units (NOX1, NOX2 and p47(phox)). Furthermore, GPE-mediated NOX inhibition was associated with a strong decrease in nuclear HIF-1α levels as well as reduction in the proliferative and clonogenic potential of PCa cells. More importantly, GPE treatment neither inhibited NOX activity nor showed any cytotoxicity against non-neoplastic prostate epithelial PWR-1E cells. Overall, these results suggest that GPE could be useful in the prevention of PCa progression via inhibiting NOX activity.

  5. Modular and Stereodivergent Approach to Unbranched 1,5,9,n-Polyenes: Total Synthesis of Chatenaytrienin-4.

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    Adrian, Juliane; Stark, Christian B W

    2016-09-16

    An iterative strategy for the stereodivergent synthesis of unbranched 1,5,9,n-polyenes (and -polyynes) was investigated. Starting from a terminal alkyne the iteration cycle consists of a C3 extension (allylation), a chemoselective hydroboration, an alkyne reduction, and an oxidation of the associated alcohol with subsequent C1 homologation. Double bond geometry is controlled using stereoselective alkyne reductions, employing either the Lindlar hydrogenation protocol or an aluminum hydride reduction. In a model sequence it was demonstrated that the strategy is applicable to the synthesis of 1,5,9,n-polyenes with any possible double bond configuration accessible in equally high efficiency and selectivity. It is worth noting that our approach does not require any protecting group chemistry. Furthermore, using the same strategy, the first total synthesis of chatenaytrienin-4, the proposed unsaturated biosynthetic precursor of the bis-THF acetogenin membranacin, was examined. Thus, the all-cis 1,5,9-triene natural product was prepared in 15 steps from commercially available starting materials in 6% overall yield.

  6. CONSTITUINTES QUÍMICOS E ATIVIDADE FITOTÓXICA DAS FOLHAS DE Annona nutans

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    Nathália Lucca Silva

    2015-05-01

    Full Text Available The phytochemical investigation and evaluation of the phytotoxic effect of the extract and fractions obtained from the leaves of Annona nutans (R. E. Fr. R. E. Fr. were performed. Phytotoxic activity was assessed on radicle and hypocotyl of Allium cepa and Lactuca sativa, where chloroform and ethyl acetate fractions proved active. Phytochemical investigation of the chloroform fraction was allowed identification of polyketides derivatives: triacontanal, 16-hentriacontane, octacosanol and triacontanol, using the 1H NMR technique associated with data from GC/MS. Using ethyl acetate fraction, with low activity, flavonoids 3-O-β-D-galactopyranosyl-isorhamnetin, 3-O-β-D-galactopyranosyl-quercetin and 3-O-β-D-apiofuranosyl-(1→2-galactopyranosyl-quercetin were identified, determined by spectrometric techniques one and two-dimensional NMR, combined with mass spectral data. All substances are being reported for the first time in Annona nutans. The phytotoxic activity of chloroform fraction may be related to the presence of triacontanol and similar substances. Triacontanol stimulates growth at very low concentrations, but can have an inhibitory effect at higher concentrations, such as those reported for auxin analogs. The toxicity assay using Artemia salina (BST was also performed, with the chloroform fraction showing a negligible lethal dose, LD50 = 500 mg mL-1, while the other fractions and extracts showed no activity. Thus, the presence of acetogenins was ruled out.

  7. The combined action of phytolarvicides for the control of dengue fever vector, Aedes aegypti

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    Adelia Grzybowski

    2012-06-01

    Full Text Available Amongst other botanical sources, Annona muricata L., Annonaceae, seeds and Piper nigrum L., Piperaceae, fruits are particularly enriched with acetogenins and piperine-related amides, respectively. These crude ethanolic extracts are potent Aedes aegypti bioactives that can kill Aedes aegypti larvae (dengue fever mosquito. A. muricata displayed a 93.48 µg/mL LC50 and P. nigrum an 1.84 µg/mL LC50. An uncommon pharmacognostical/toxicological approach was used, namely different combinations of both extracts to achieve an improved lethal effect on the larvae. The independence test (χ² was utilized to evaluate the combination of the two crude extracts. All of the tested combinations behaved synergistically and these novel results were attributed to the completely different biochemical mechanisms of the differentiated chemical substances that were present in the two botanical sources. Besides the two above selected plants, Melia azedarach L., Meliaceae, Origanum vulgare L., Lamiaceae, and Ilex paraguariensis A. St.-Hil., Aquifoliaceae, in order of decreasing toxicity, may also be sought as potential extracts for the sake of synergic combinations.

  8. Antimicrobial activity of some seaweeds species from Red sea, against multidrug resistant bacteria

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    Shimaa M. El Shafay

    2016-03-01

    Full Text Available This study evaluates the antibacterial activity of diethyl ether, methanol, ethanol and chloroform extracts of red algae Ceramium rubrum (Rhodophyta, Sargassum vulgare, Sargassum fusiforme and Padina pavonia (Phaeophyta collected from Red sea, Egypt. The algal extracts were tested for their antibacterial activity against ten multidrug resistant clinical isolates of Gram positive and Gram negative bacteria. The highest inhibition activity among all extracts was obtained with 100 μl diethyl ether extract S. fusiforme against Staphylococcus aureus 2 and 50 μl ethanol extract of S. vulgare against Klebsiella pneumoniae. The algal extract of S. fusiforme and S. vulgare was characterized by Gas chromatography–mass spectrometry (GC–MS. The compounds with antimicrobial activity were identified, such as phenols, terpenes, acetogenins, indoles, fatty acids and volatile halogenated hydrocarbons. Transmission electron microscopy was applied for determining the morphological changes in S. aureus 2 and K. pneumonia treated with 100 μl diethyl ether extract of S. fusiforme and 50 μl ethanol extract of S. vulgare, respectively. Perforation of cell wall, leakage of cytoplasmic contents, severe distortion of outer cell shape, inner chromatin mild scattered cytoplasmic vacuolation, rupture of cell wall, and decreased cell size for both bacterial isolates treated with 100 μl diethyl ether of S. fusiforme extract and 50 μl S. vulgare ethanolic extract were recorded.

  9. Larvicidal and Cytotoxic Potential of Squamocin on the Midgut of Aedes aegypti (Diptera: Culicidae

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    Marilza S. Costa

    2014-03-01

    Full Text Available Acetogenins are secondary metabolites exclusively produced by Annonaceae, which have antitumor, cytotoxic, and pesticide activities. In this study, we evaluated the larvicidal and cytotoxic effect of squamocin from Annona squamosa on Aedes aegypti (Diptera: Culicidae midgut. The compound was solubilized in 2% Tween 20 at 10, 20, 50, 80 and 100 ppm. The assay was conducted in a completely randomized design with four replications, each with 20 third-instar larvae. Larval mortality was assessed every hour until total mortality, and the data were subjected to Probit analysis. Cellular damage was evaluated every 30 min in groups comprising five larvae subjected to squamocin at 50 and 100 ppm for 240 min. The total larval mortality occurred after 360 min following application of 50, 80, and 100 ppm squamocin, and 600 min after applying other concentrations with LC50 at 6.4 ppm. Both 50 and 100 ppm of squamocin showed cytotoxic activity in the midgut epithelium of A. aegypti after 240 min with 50 ppm resulting in midgut cells with light cytoplasm containing small vacuoles, whereas at 100 ppm were found cells with cytoplasm highly vacuolated, damaged apical surface and cell protrusion toward the gut lumen. In conclusion, squamocin has the potential to control A. aegypti.

  10. Evaluation of cytotoxicity of aqueous extract of Graviola leaves on squamous cell carcinoma cell-25 cell lines by 3-(4,5-dimethylthiazol-2-Yl -2,5-diphenyltetrazolium bromide assay and determination of percentage of cell inhibition at G2M phase of cell cycle by flow cytometry: An in vitro study

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    Visveswaraiah Paranjyothi Magadi

    2015-01-01

    Full Text Available Introduction: Malignancies constitute a wide variety of disorders having high mortality and morbidity rates. Current protocols for management include surgical intervention, chemotherapy, and radiation which possess numerous adverse effects. Many phytochemicals are available with anticancer properties similar to anticancer drugs. Major benefit of these compounds is apparent lack of toxicity to normal tissues. Graviola (botanical name: Annona Muricata contain bioactive compound “annonaceous acetogenins” known for anticancer activity on cancer cell lines. Aims: To determine cytotoxicity of Graviola and percentage cell inhibition at G2M phase of cell cycle. Settings and Design: The cytotoxicity of aqueous extract of Graviola leaves on squamous cell carcinoma (SCC-25 cell lines at various concentrations evaluated using 3-(4,5-dimethylthiazol-2-Yl-2,5-diphenyltetrazolium bromide (MTT assay. The percentage of SCC-25 cell inhibition at G2M phase of cell cycle determined using flow cytometry. Methods: Graviola Leaves, American Type Culture Collection SCC-25 cell lines were procured from Skanda Laboratories, Bengaluru. The cytotoxicity of aqueous extract of Graviola on SCC-25 cells at various concentrations evaluated using MTT assay. The percentage of SCC-25 cell inhibition at G2M phase of cell cycle determined using flow cytometry. Statistical Analysis: Statistical analysis was done using one-way ANOVA. Results: MTT assay showed statistically significant (P < 0.001 dose-dependent inhibition of SCC-25 cell lines by Graviola with IC50 value of 12.42 μg/ml. Flow cytometry revealed that Graviola at 25 and 50 g/ml arrested 53.39% and 52.09% cells in G2M phase of cell cycle respectively, which was statistically significant. Conclusion: Graviola showed significant cytotoxic activity and percentage of cell inhibition at G2M phase cell cycle against SCC-25 cell lines.

  11. Evaluation of cytotoxicity of aqueous extract of Graviola leaves on squamous cell carcinoma cell-25 cell lines by 3-(4,5-dimethylthiazol-2-Yl) -2,5-diphenyltetrazolium bromide assay and determination of percentage of cell inhibition at G2M phase of cell cycle by flow cytometry: An in vitro study

    Science.gov (United States)

    Magadi, Visveswaraiah Paranjyothi; Ravi, Venkatadasappa; Arpitha, Anantharaju; Litha; Kumaraswamy, Kikkerilakshminarayana; Manjunath, Krishnappa

    2015-01-01

    Introduction: Malignancies constitute a wide variety of disorders having high mortality and morbidity rates. Current protocols for management include surgical intervention, chemotherapy, and radiation which possess numerous adverse effects. Many phytochemicals are available with anticancer properties similar to anticancer drugs. Major benefit of these compounds is apparent lack of toxicity to normal tissues. Graviola (botanical name: Annona Muricata) contain bioactive compound “annonaceous acetogenins” known for anticancer activity on cancer cell lines. Aims: To determine cytotoxicity of Graviola and percentage cell inhibition at G2M phase of cell cycle. Settings and Design: The cytotoxicity of aqueous extract of Graviola leaves on squamous cell carcinoma (SCC-25) cell lines at various concentrations evaluated using 3-(4,5-dimethylthiazol-2-Yl)-2,5-diphenyltetrazolium bromide (MTT) assay. The percentage of SCC-25 cell inhibition at G2M phase of cell cycle determined using flow cytometry. Methods: Graviola Leaves, American Type Culture Collection SCC-25 cell lines were procured from Skanda Laboratories, Bengaluru. The cytotoxicity of aqueous extract of Graviola on SCC-25 cells at various concentrations evaluated using MTT assay. The percentage of SCC-25 cell inhibition at G2M phase of cell cycle determined using flow cytometry. Statistical Analysis: Statistical analysis was done using one-way ANOVA. Results: MTT assay showed statistically significant (P < 0.001) dose-dependent inhibition of SCC-25 cell lines by Graviola with IC50 value of 12.42 μg/ml. Flow cytometry revealed that Graviola at 25 and 50 g/ml arrested 53.39% and 52.09% cells in G2M phase of cell cycle respectively, which was statistically significant. Conclusion: Graviola showed significant cytotoxic activity and percentage of cell inhibition at G2M phase cell cycle against SCC-25 cell lines. PMID:26681860

  12. Atividade biológica de metabólitos secundários de algas marinhas do gênero Laurencia Biological activity of the secondary metabolite from marine algae of the genus Laurencia

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    Fernanda L. da S. Machado

    2010-07-01

    Full Text Available As algas vermelhas do gênero Laurencia são conhecidas como uma riquíssima fonte de metabólitos secundários. As principais classes químicas já isoladas são terpenos - sesquiterpenos, diterpenos, triterpenos - e acetogeninas. Estudos apontam que estas substâncias apresentam importantes atividades biológicas, principalmente citotóxica e antibacteriana. Existem ainda alguns poucos trabalhos com informações sobre atividade antiparasitária, antiviral e antifúngica dos metabólitos de Laurencia. O forte perfil bioativo observado em alguns estudos sugere que alguns destes metabólitos podem ser futuramente utilizados como fármacos ou como protótipos de novos agentes antitumorais e antibacterianos. Muitos dos metabólitos de Laurencia ainda não foram avaliados sob o ponto de vista farmacológico, o que representa um grande potencial a ser explorado por diversos campos da farmacologia.The red alga of the genus Laurencia is known as an endless source of metabolites. The main substances produced are sesquiterpenes, diterpenes, triterpenes and acetogenins. Many studies reveal that these metabolites are active, especially cytotoxic and antibacterial. There are few other studies that describe the antiparasital, antifungal and antiviral actions of the metabolites produced by the alga of the genus Laurencia. The results observed in some studies suggest that these metabolites may be used in the future as drugs or lead compounds as antitumoral and/or antibacterial agents. Many metabolites have not been submitted to pharmacological studies which still represents an area to be explored.

  13. UPLC–QTOF–MS and NMR analyses of graviola (Annona muricata leaves

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    Ingrid Vieira Machado de Moraes

    2016-04-01

    Full Text Available ABSTRACT Graviola leaves (Annona muricata L., Annonaceae are used by some people to try to treat or even cure cancer, even though over-consumption of the fruit, which contains the neurotoxins annonacin and squamocin has caused an atypical form of Parkinson's disease. In previous analyses, the fruits were extracted with methanol under ambient conditions before analyses. In the present study, UPLC–QTOF–MS and NMR were used to analyze freeze-dried graviola leaves that were extracted using dry methanol and ethanol at 100 ºC and 10 MPa (100 atm pressure in a sealed container. Methanol solubilized 33% of the metabolites in the lyophilized leaves. Ethanol solubilized 41% of metabolites in the lyophilized leaves. The concentrations of total phenolic compounds were 100.3 ± 2.8 and 93.2 ± 2.0 mg gallic acid equivalents per g of sample, for the methanolic and ethanolic extracts, respectively. Moreover, the toxicophore (unsaturated γ-lactone that is present in neurotoxic acetogenins was found in the lipophilic portion of this extract. The concentrations of the neurotoxins annonacin and squamocin were found by UPLC–QTOF–MS to be 305.6 ± 28.3 and 17.4 ± 0.89 µg/g-dw, respectively, in the dried leaves. Pressurized methanol solubilized more annonacin and squamocin than ethanol. On the other hand, a hot, aqueous infusion solubilized only 0.213% of the annonacin and too little of the squamocin to be detected. So, graviola leaves contain significant amounts of the neurotoxins annonacin and squamocin, as well as some potentially healthy phenolic compounds. Finally, the potential neurotoxicity of whole leaves in dietary supplements could be much higher than that of a tea (hot aqueous infusion that is made from them.

  14. Actividad tripanomicida en el Tripanosoma cruzi del extracto etanólico de las semillas de la Xylopia aromatica Trypanomicidal activity of etanol extract from Xylopia aromatica on Tripasonoma cruzi

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    José Luís Tenorio Vergara

    2006-12-01

    Full Text Available La enfermedad de Chagas afecta a las comunidades más desfavorecidas en el Departamento del Tolima-Colombia; el tratamiento poco asequible y la resistencia del parasito a los medicamentos tradicionales, hacen necesario la búsqueda de tratamientos alternativos en la actualidad. En este estudio se evaluó la actividad tripanomicida de la fracción metanólica del extracto etanólico de las semillas de Xylopia aromatica (Annonaceae, la cual presentó actividad citotóxica y en la que se detectó la presencia de Acetogeninas. La fracción fue probada a diferentes concentraciones frente a formas epimastigotas del Tripanosoma cruzi y se utilizó el Benznidazol® como medicamento referencia. La fracción metanólica presentó actividad antiparasitaria, con más efectividad que el medicamento de referencia a concentraciones mayores de 211,6 µg/mL en la cual se alcanza el 70 % de organismos muertos.Chagas´s disease affects the most underprivileged communities in Departamento de Tolima, Colombia; the poorly accessible treatment and the parasite´s resistance to traditional drugs make it necessary to search for alternative therapies at present. This study assessed the trypanomicidal activity of methanol fraction of ethanol extract from Xylkopia aromatica seeds(Annonaceae that had cytotoxic activity,with presence of Acetogenins being detected. This fraction was tested at different concentrations to Trypanosoma cruzi epimastigotes, and Benzanidazol® was used as reference drug. Methanol fraction showed parasiticidal properties, being more effective than the reference drug at concentrations over 211,6 µg/mL at which 70 % of organisms die.

  15. Comparative analysis of the corps en cerise in several species of Laurencia (Ceramiales, Rhodophyta from the Atlantic Ocean

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    Mutue T. Fujii

    2012-08-01

    Full Text Available Different species of Laurencia have proven to be a rich source of natural products yielding interesting bioactive halogenated secondary metabolites, such as terpenoids and acetogenins. It is shown that such compounds are accumulated in the spherical, reniform to claviform refractive inclusions called corps en cerise (CC, which are intensively osmiophilic and located mainly in the cortical cells of the thalli and also in trichoblast cells. Up to now, it was believed that CC were present only in these two kinds of cells. Recently, however, a species of Laurencia, L. marilzae, with CC in all cells of the thallus, i.e., cortical, medullary, including the pericentral and axial cells, as well as in the trichoblasts, was described from the Canary Islands, and subsequently also reported to Brazil and Mexico. Within the Laurencia complex, only Laurencia species produce CC. Since the species of Laurencia are targets of interest for the prospection of bioactive substances due to their potential antibacterial, antifungal, anticholinesterasic, antileishmanial, cytotoxic, and antioxidant activities, the present paper carries out a comparative analysis of the corps en cerise in several species of Laurencia from the Atlantic Ocean to obtain basic information that can support natural product bioprospection projects. Our results show that the number and size of the CC are constant within a species, independent of the geographical distribution, corroborating their use for taxonomical purposes to differentiate groups of species that present a lower number from those that have a higher number. In this regard, there was a tendency for the number of CC to be higher in some species of Laurencia from the Canary Islands. The presence of CC can also be used to distinguish species in which these organelles are present in all cells of the thallus from those in which CC are restricted to the cortical cells. Among the species analyzed, L. viridis displayed the most varied

  16. Metabólitos secundários presentes na Annona muricata L e suas propriedades nutricionais e funcionais em oncologia

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    Erlania Carmo Freitas

    2017-01-01

    Full Text Available A nutrição funcional tem ganhado espaço nos últimos anos por sua ação terapêutica, com destaque para o fruto graviola. Vários estudos bem conduzidos sugerem que o fruto possui quantidades consideráveis de minerais, fibras, compostos antioxidantes e substancias que atuam contra células cancerígenas, com destaque para a ação das acetogeninas. Contudo objetivou-se realizar a quantificação dos compostos fenólicos presentes em polpas da graviola in natura e congelada e realizar uma revisão de trabalhos que justifiquem o uso da graviola na diminuição da proliferação do câncer. Foram identificadas quantidades bastante significativas de compostos fenólicos nas amostras de graviola, porém sem diferenciação do tratamento congelado ou in natura. Logo sugere seu uso na prevenção do câncer e necessitam de mais estudos para a sua utilização no tratamento de pacientes oncológicos. ABSTRACT Secondary Metabolitics Present at Annona Muricata L and Its Nutritional and Functional Properties in Oncology Functional nutrition has gained ground in recent years for its therapeutic action, especially the soursop fruit. Several well-conducted studies suggest that the fruit has considerable amounts of minerals, fiber, antioxidants and substances that act against cancer cells, highlighting the action of acetogenins. However it aimed to perform the quantification of the phenolic compounds present in soursop pulp of fresh and frozen and conduct a review of studies that justify the use of soursop in reducing cancer proliferation. They were identified fairly significant amounts of phenolic compounds in the samples of soursop, however no differentiation of treatment or frozen raw. Logo suggests its use in preventing cancer and need further studies for its use in the treatment of cancer patients.

  17. Toxicity of an Annonin-Based Commercial Bioinsecticide Against Three Primary Pest Species of Stored Products.

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    Ribeiro, L P; Zanardi, O Z; Gonçalves, G L P; Ansante, T F; Yamamoto, P T; Vendramim, J D

    2017-03-28

    The effects of a bioinsecticide formulation based on extract of Annona squamosa L. (Annonaceae) containing 10,000 mg L(-1) of acetogenin annonin as the main active ingredient were investigated against three primary pest species of stored grains in Brazil [maize weevil Sitophilus zeamais Motschulsky (Coleoptera: Curculionidae), Mexican bean weevil Zabrotes subfasciatus (Boheman) (Coleoptera: Chrysomelidae: Bruchinae), and cowpea weevil Callosobruchus maculatus (Fabricius) (Coleoptera: Chrysomelidae: Bruchinae)] by means of residual contact bioassays. In a concentration-dependent manner, the annonin-based commercial bioinsecticide caused significant adult mortality of C. maculatus (LC50 = 6890 μL kg(-1)), S. zeamais (LC50 = 2781 μL kg(-1)), and Z. subfasciatus (LC50 = 2120 μL kg(-1)) after 120 h of residual contact exposure. In addition to acute toxicity, the tested bioinsecticide also promoted a significant reduction of the number of eggs laid by females of C. maculatus (EC50 = 5949.7 μL kg(-1)) and Z. subfasciatus (EC50 = 552.7 μL kg(-1)). Moreover, the bioinsecticide significantly reduced the number of emerged insects (F1 generation) of C. maculatus (EC50 = 2763.0 μL kg(-1)), S. zeamais (EC50 = 1380.8 μL kg(-1)), and Z. subfasciatus (EC50 = 561.5 μL kg(-1)). The bioinsecticide also reduced the percentage of damaged grains for the three pest species studied, and its grain-protectant properties are comparable to or superior in efficacy in relation to a diatomaceous earth-based insecticide (Insecto® at 1000 mg kg(-1)) used as a positive control. Thus, this standardized formulation has promising bioactivity against stored insect species and can be a useful component for IPM of stored grains in Brazil and elsewhere.