• Title/Summary/Keyword: Dammarane-type triterpenes

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Ginsenoside Rg12, a new dammarane-type triterpene saponin from Panax ginseng root

  • Lee, Dong Gu;Lee, Jaemin;Cho, Ik-Hyun;Kim, Hak-Jae;Lee, Sang-Won;Kim, Young-Ock;Park, Chun-Gun;Lee, Sanghyun
    • Journal of Ginseng Research
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    • v.41 no.4
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    • pp.531-533
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    • 2017
  • Background: Panax ginseng has been used as Korean medicine for various diseases. It has antioxidant, hypotensive, sedative, analgesic, and endocrine activities. Dammarane-type triterpenes from the plant have various beneficial effects. Methods: A dammarane-type triterpene saponin was isolated from P. ginseng root through chromatography such as repeated column chromatography and medium pressure liquid chromatography. Results and conclusion: New dammarane-type triterpene saponin was isolated for the first time from nature. The structure was elucidated as ginsenoside Rg12 (1) based on spectral data. There may be good materials from P. ginseng for the development of industrial applications such as nutraceutical, pharmaceutical, and cosmeceutical purposes.

New hydroperoxylated and 20,24-epoxylated dammarane triterpenes from the rot roots of Panax notoginseng

  • Shang, Jia-Huan;Sun, Wen-Jie;Zhu, Hong-Tao;Wang, Dong;Yang, Chong-Ren;Zhang, Ying-Jun
    • Journal of Ginseng Research
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    • v.44 no.3
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    • pp.405-412
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    • 2020
  • Background: Root rot is a serious destructive disease of Panax notoginseng, a famous cultivated araliaceous herb called Sanqi or Tianqi in Southwest China. Methods: The chemical substances of Sanqi rot roots were explored by chromatographic techniques. MS, 1D/2D-NMR, and single crystal X-ray diffraction were applied to determine the structures. Murine macrophage RAW264.7 and five human cancer cell lines were used separately for evaluating the antiinflammatory and cytotoxic activities. Results and Conclusion: Thirty dammarane-type triterpenes and saponins were isolated from the rot roots of P. notoginseng. Among them, seven triterpenes, namely, 20(S)-dammar-25-ene-24(S)-hydroperoxyl-3β,6α,12β,20-tetrol (1), 20(S)-dammar-3-oxo-23-ene-25-hydroperoxyl-6α,12β,20-triol (2), 20(S)-dammar-12-oxo-23-ene-25-hydroperoxyl-3β,6α,20-triol (3), 20(S)-dammar-3-oxo-23-ene-25-hydroperoxyl-12β,20-diol (4), 20(S),24(R)-epoxy-3,4-seco-dammar-25-hydroxy-12-one-3-oic acid (5), 20(S),24(R)-epoxy-3,4-seco-dammar-25-hydroxy-12-one-3-oic acid methyl ester (6), and 6α-hydroxy-22,23,24,25,26,27-hexanordammar-3,12,20-trione (7), are new compounds. In addition, 12 known ones (12-16 and 19-25) were reported in Sanqi for the first time. The new Compound 1 showed comparable antiinflammatory activity on inhibition of NO production to the positive control, whereas the known compounds 9, 12, 13, and 16 displayed moderate cytotoxicities against five human cancer cell lines. The results will provide scientific basis for understanding the chemical constituents of Sanqi rot roots and new candidates for searching antiinflammatory and antitumor agents.

Tertiary Structure of Ginsenoside Re Studied by NMR Spectroscopy

  • Kang, Dong-Il;Jung, Ki-Woong;Kim, Seoung-Keum;Lee, Sung-Ah;Jhon, Gil-Ja;Kim, Yang-Mee
    • Bulletin of the Korean Chemical Society
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    • v.28 no.12
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    • pp.2209-2213
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    • 2007
  • Ginseng has long been used as a traditional medicine in Asian countries including Korea and China. In recent years, it has been reported that the biological activities of ginseng are due to its active components, ginsenosides. Ginsenosides are represented by triterpenes of the dammarane type. Ginsenoside Re consists of two glucose rings, one rhamnose ring, and the triterpene ring. In the present study ginsenoside Re has been isolated from the Korean ginseng (Panax ginseng) and the tertiary structure has been determined using NMR spectroscopy. Flexibilities around each linkages described by seven torsion angles were considered. The structures of ginsenoside Re obtained by NMR spectroscopy show the rigidity around the glucopyranosyl ring II and alkene side chain. The dihedral angles of φ5, φ6, φ7 are about 150o, 50o and 45o, respectively. In addition, flexibility exists around rhamnopyranosyl and glucopyronosyl moiety. The linkage around the rhamnopyranosyl and glucopyranosyl ring I, are divided into three groups. This flexibility seems to play important role in regulation of the hydrophobic surface exposed to the solvent. Because of the growing need for the structural determination of ginsenoside, this result can help to understand their well-accepted pharmacological effects of ginsenoside Re.