• Title/Summary/Keyword: Triterpene saponins

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Two New Antiinflammatory Triterpene Saponins from the Egyptian edicinal Food Black Cumin (Seeds of Nigella sativa)

  • Elbandy, Mohamed;Kang, Ok-Hwa;Kwon, Dong-Yeul;Rho, Jung-Rae
    • Bulletin of the Korean Chemical Society
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    • v.30 no.8
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    • pp.1811-1816
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    • 2009
  • An extensive phytochemical investigation of the polar fractions of a methanolic extract of Egyptian medicinal food, black cumin (seeds of Nigella sativa L.) led to the isolation of two new triterpene saponins, named sativosides A and B (1-2), along with four known saponins (3-6). Sativoside A (1) is the first example of saponins containing 18-ene triterpene aglycon not only in this Nigella genus but also in the family Ranunculaceae. The structure of the new saponins was elucidated mainly by a combination of 1D and 2D NMR data, together with HRFABMS and acid hydrolysis. Three compounds (1-3) showed the significant inhibition effect of phorbol 12-myristate 13-acetate (PMA) plus calcium ionophore A23187-induced production of IL-6 in a human mast cell (HMC-1) line.

Three New Oleanane-Type Triterpene Saponins from Gladiolus gandavensis

  • Tai, Zhi-Gang;Cai, Le;Yang, Ya-Bin;Liu, Chuan-Shui;Xia, Jian-Jun;Ding, Zhong-Tao
    • Bulletin of the Korean Chemical Society
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    • v.31 no.10
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    • pp.2786-2790
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    • 2010
  • Three new oleanane-type triterpene saponins (1, 2 and 3) were isolated from aerial parts of Gladiolus gandavensis, along with two known compounds (4 and 5). Their structures were elucidated as 29-O-($\beta$-D-glucopyranosyl)-$2{\beta}$,$3{\beta}$-dihydroxyolean-12-en-28-oicacid(1), 3-O-($\beta$-D-xylopyranosyl)-29-O-($\beta$-D-glucopyranosyl)-12-en-28-oic acid (2), and $2{\beta}$,$3{\beta}$,29-trihydroxyolean-12-en-28-oic acid 28-O-[$\beta$-D-glucopyranosyl($1{\rightarrow}2$)-($\alpha$-L-rhamnopyranosyl($1{\rightarrow}6$))-$\beta$-D-glucopyranosyl] ester (3), by spectroscopic methods, and by comparison with known analogues. These oleanane-type triterpene saponins glycosidated at C-29 were not obtained frequently.

Dammarane-type triterpene oligoglycosides from the leaves and stems of Panax notoginseng and their antiinflammatory activities

  • Li, Juan;Wang, Ru-Feng;Zhou, Yue;Hu, Hai-Jun;Yang, Ying-Bo;Yang, Li;Wang, Zheng-Tao
    • Journal of Ginseng Research
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    • v.43 no.3
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    • pp.377-384
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    • 2019
  • Background: Inflammation is widespread in the clinical pathology and closely associated to the progress of many diseases. Triterpenoid saponins as a key group of active ingredients in Panax notoginseng (Burk.) F.H. Chen were demonstrated to show antiinflammatory effects. However, the chemical structures of saponins in the leaves and stems of Panax notoginseng (PNLS) are still not fully clear. Herein, the isolation, purification and further evaluation of the antiinflammatory activity of dammarane-type triterpenoid saponins from PNLS were conducted. Methods: Silica gel and reversed-phase C8 column chromatography were used. Furthermore, preparative HPLC was used as a final purification technique to obtain minor saponins with high purities. MS, NMR experiments, and chemical methods were used in the structural identifications. The antiinflammatory activities of the isolated saponins were assessed by measuring the nitric oxide production in RAW 264.7 cells stimulated by lipopolysaccharides. Real-time reverse transcription polymerase chain reaction was used to measure the gene expressions of inflammation-related gene. Results: Eight new minor dammarane-type triterpene oligoglycosides, namely notoginsenosides LK1-LK8 (1-8) were obtained from PNLS, along with seven known ones. Among the isolated saponins, gypenoside IX significantly suppressed the nitric oxide production and inflammatory cytokines including tumor necrosis $factor-{\alpha}$, interleukin 10, interferon-inducible protein 10 and $interleukin-1{\beta}$. Conclusion: The eight saponins may enrich and expand the chemical library of saponins in Panax genus. Moreover, it is reported for the first time that gypenoside IX showed moderate antiinflammatory activity.

Effects of Precursor and Thidiazuron on Triterpene Saponin Biosynthesis in Centella asiatica (L.) Urban

  • Kim, Ok-Tae;Kim, Min-Young;Ahn, Jun-Cheul;Li, Mei-Yang;Hwang, Baik
    • Korean Journal of Medicinal Crop Science
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    • v.13 no.2
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    • pp.91-94
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    • 2005
  • Plants have been known to accumulate a very diverse range of triterpene saponins. We have investigated the regulation of saponin biosynthesis in higher plants using Centella asiatica (L.) Urban as a model plant. Effects of a feeding precursor on asiaticoside production from leaves and on the level of two-type OSCs mRNA were investigated. As a feeding precursor, squalene negatively affected the levels of CYS and bAS mRNA, but it also decreased the production of asiaticoside from whole plants. Plant hormones regulate secondary metabolism, and in plant tissue cultures they could affect both culture growth and secondary metabolite production. Although enhancement of asiaticoside production from whole plant cultures by addition of TDZ (thidiazuron) has been reported, the positive effect of TDZ on the levels of OSCs transcripts was not observed.

Chemical diversity of ginseng saponins from Panax ginseng

  • Shin, Byong-Kyu;Kwon, Sung Won;Park, Jeong Hill
    • Journal of Ginseng Research
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    • v.39 no.4
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    • pp.287-298
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    • 2015
  • Ginseng, a perennial plant belonging to the genus Panax of the Araliaceae family, is well known for its medicinal properties that help alleviate pathological symptoms, promote health, and prevent potential diseases. Among the active ingredients of ginseng are saponins, most of which are glycosides of triterpenoid aglycones. So far, numerous saponins have been reported as components of Panax ginseng, also known as Korean ginseng. Herein, we summarize available information about 112 saponins related to P. ginseng; >80 of them are isolated from raw or processed ginseng, and the others are acid/base hydrolysates, semisynthetic saponins, or metabolites.

Triterpenoid Saponin Contents of the Leaf, Stem and Root of Codonopsis lanceolata (더덕 잎, 줄기, 뿌리 부위의 Triterpenoid 사포닌 함량)

  • Kim, Ji Ah;Moon, Heung Kyu;Choi, Yong Eui
    • Korean Journal of Medicinal Crop Science
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    • v.22 no.1
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    • pp.1-7
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    • 2014
  • Codonopsis lanceolata (Campanulaceae) has been used in traditional medicines, as its roots contain several kinds of 3,28-bidesmosidic triterpenoid saponin with high medicinal values. In this study, we induced hairy root-derived transgenic plants of C. lanceolata and analyzed triterpenoid saponins from the leaf, stem and root. Transgenic plants were regenerated from the hairy roots via somatic embryogenesis. The saponins are lancemaside A, B and E, foetidissimoside A, and aster saponin Hb. Transgenic plants contained richer triterpenoids saponin than wild-type plants. Major saponin lancemaside A was the most abundant saponin in the stem from transgenic-plant, $4.76mg{\cdot}1^{-1}dry$ stem. These results suggest that transgenic plants of C. lanceolata could be used as medicinal materials for the production of triterpene saponins.

Chemical Composition and Pharmacological Activities of Vietnamese Ginseng, Panax viehamensis

  • Duc, Nguyen-Minh;Nham, Nguyen-Thoi
    • Proceedings of the Ginseng society Conference
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    • 1998.06a
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    • pp.127-137
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    • 1998
  • From the underground part of Panax vietnamensis Ha et Grushv., commonly known as Vietnamese ginseng, 50 triterpene glycosides including 24 new dammarane saponins named visa-ginsenosides-Rl-24 were isolated and identified. The structure of the new saponins was elucidated based on chemical and spectroscopic evidence. The saponin composition of Vietnamese ginseng is almost similar to that of ginseng (Panax ginseng C.A. Meyer) and other cultivated Panax spp. However, the content of ocotillos-type saponins, especially that of the major saponin, majonoside-R2 (5.29% yield), was surprisingly very high. The pharmacological activities of Vietnamese ginseng are essentially similar to those of ginseng. In addition, it has marked antibacterial activity against pathogenic Streptococcus app. and is effective in treatment of granular angina. The chemical composition and pharmacological activities have made Vietnamese ginseng an interesting member of Panax spp. from chemotaxonomical and pharmacological points of view,

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Phytochemical Studies on Astragalus Root(1) - Saponins

  • Kim, Ju-Sun;Yean, Min-Hye;Lee, Eun-Ju;Kang, Sam-Sik
    • Natural Product Sciences
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    • v.14 no.1
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    • pp.37-46
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    • 2008
  • From the 70% EtOH extract of the roots of Astragalus membranaceus (Leguminosae), fifteen saponins were isolated and identified as astragaloside I (1), isoastragaloside II (2), astragaloside II (3), agroastragaloside I (4), cyclogaleginoside B (5), cycloaraloside A (6), brachyoside B (7), agroastragaloside II (8), astragaloside III (9), astragaloside IV (10), astramembranoside A (11), astramembranoside B (12), cylocanthoside E (13), cyclounifolioside B (14) and azukisaponin V methyl ester (15) by spectroscopic methods. Ten compounds 1 - 3, 5 - 7, 9 - 11 and 14 have cycloastragenol as an aglycon, and four compounds 4, 8 , 12, and 13 have cyclocanthogenin as an aglycon. The hairy roots of A. membranaceus were shown to produce previously unreported cycloartane-type saponins such as agroastragalosides I (4) and II (8) and cycloastragenol $3-O-{\beta}-D-xyloside$ (5), together with the known saponins. This is the first report of these saponins (4, 5, and 8) from the intact plant. Although the occurrence of the oleanane-type triterpene saponin, azukisaponin V methyl ester (15), in Astragalus plants has been demonstrated by others, this is the first report of the azukisaponin V methyl ester (15) from the Astragalus plants.