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Chemical Compound Review

AC1MIVF3     (3S,8R,9R,10S,12R,13S,14S,17S) -17-[(2R)-2...

Synonyms: 7755-01-3, Protopanaxadiol
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Disease relevance of Protopanaxadiol


Psychiatry related information on Protopanaxadiol

  • We previously showed that 20-O-beta-D-glucopyranosyl-20(S)-protopanaxadiol (M1), a metabolite of protopanaxadiol-type ginseng saponins by intestinal bacteria had axonal extension activity in degenerated neurons, and improved memory disorder and synaptic loss induced by an active fragment of amyloid beta, Abeta(25-35) [5].
  • Korean red ginseng saponins with low ratios of protopanaxadiol and protopanaxatriol saponin improve scopolamine-induced learning disability and spatial working memory in mice [6].

High impact information on Protopanaxadiol


Biological context of Protopanaxadiol


Anatomical context of Protopanaxadiol


Associations of Protopanaxadiol with other chemical compounds


Gene context of Protopanaxadiol

  • In vitro inhibitory effect of protopanaxadiol ginsenosides on tumor necrosis factor (TNF)-alpha production and its modulation by known TNF-alpha antagonists [19].
  • The present study demonstrated in vivo and in vitro antimetastatic activities of a major intestinal bacterial metabolite M1 formed from protopanaxadiol saponins of ginseng (the root of Panax ginseng C. A. Meyer) in comparison with its whole standardized extract and ginsenosides Rb1, Rb2, and Rc [20].
  • A carrier protein (bovine serum albumin (BSA)) was coupled to the C-26 position on the unsaturated side chain of the protopanaxadiol moiety to prepare the immunogen [21].
  • However, protopanaxadiol glycoside ginsenosides Rb1, Rb2 and Rc isolated from ginseng were mostly not transformed to ginsenoside Rg3 by the incubation in neutral condition [3].
  • Ginseng total saponins and one of the constituents, protopanaxatriol saponin, suppressed the development of morphine tolerance in a concentration dependent manner in GPI preparation, though another constituent, protopanaxadiol saponin, did not affect the tolerance development substantially [22].

Analytical, diagnostic and therapeutic context of Protopanaxadiol


  1. Abeta(25-35)-induced memory impairment, axonal atrophy, and synaptic loss are ameliorated by M1, A metabolite of protopanaxadiol-type saponins. Tohda, C., Matsumoto, N., Zou, K., Meselhy, M.R., Komatsu, K. Neuropsychopharmacology (2004) [Pubmed]
  2. Antitumor promotional effects of a novel intestinal bacterial metabolite (IH-901) derived from the protopanaxadiol-type ginsenosides in mouse skin. Lee, J.Y., Shin, J.W., Chun, K.S., Park, K.K., Chung, W.Y., Bang, Y.J., Sung, J.H., Surh, Y.J. Carcinogenesis (2005) [Pubmed]
  3. Transformation of ginseng saponins to ginsenoside Rh2 by acids and human intestinal bacteria and biological activities of their transformants. Bae, E.A., Han, M.J., Kim, E.J., Kim, D.H. Arch. Pharm. Res. (2004) [Pubmed]
  4. Effect of ginseng saponins on a rat visceral hypersensitivity model. Kim, J.H., Lee, J.H., Jeong, S.M., Lee, B.H., Yoon, I.S., Lee, J.H., Choi, S.H., Nah, S.Y. Biol. Pharm. Bull. (2005) [Pubmed]
  5. Metabolite 1 of protopanaxadiol-type saponins, an axonal regenerative factor, stimulates teneurin-2 linked by PI3-kinase cascade. Tohda, C., Hashimoto, I., Kuboyama, T., Komatsu, K. Neuropsychopharmacology (2006) [Pubmed]
  6. Korean red ginseng saponins with low ratios of protopanaxadiol and protopanaxatriol saponin improve scopolamine-induced learning disability and spatial working memory in mice. Jin, S.H., Park, J.K., Nam, K.Y., Park, S.N., Jung, N.P. Journal of ethnopharmacology. (1999) [Pubmed]
  7. Cyclooxygenase-2 inhibits novel ginseng metabolite-mediated apoptosis. Yim, H.W., Jong, H.S., Kim, T.Y., Choi, H.H., Kim, S.G., Song, S.H., Kim, J., Ko, S.G., Lee, J.W., Kim, T.Y., Bang, Y.J. Cancer Res. (2005) [Pubmed]
  8. In vitro inhibition of adrenal catecholamine secretion by steroidal metabolites of ginseng saponins. Tachikawa, E., Kudo, K., Hasegawa, H., Kashimoto, T., Sasaki, K., Miyazaki, M., Taira, H., Lindstrom, J.M. Biochem. Pharmacol. (2003) [Pubmed]
  9. Adjuvant effects of protopanaxadiol and protopanaxatriol saponins from ginseng roots on the immune responses to ovalbumin in mice. Sun, J., Hu, S., Song, X. Vaccine (2007) [Pubmed]
  10. Relationship between haemolytic and adjuvant activity and structure of protopanaxadiol-type saponins from the roots of Panax notoginseng. Sun, H.X., Qin, F., Ye, Y.P. Vaccine (2005) [Pubmed]
  11. Platelet activating factor antagonist activity of ginsenosides. Jung, K.Y., Kim, D.S., Oh, S.R., Lee, I.S., Lee, J.J., Park, J.D., Kim, S.I., Lee, H.K. Biol. Pharm. Bull. (1998) [Pubmed]
  12. American ginseng. III. Pharmacokinetics of ginsenosides in the rabbit. Chen, S.E., Sawchuk, R.J., Staba, E.J. European journal of drug metabolism and pharmacokinetics. (1980) [Pubmed]
  13. A novel ginseng saponin metabolite induces apoptosis and down-regulates fibroblast growth factor receptor 3 in myeloma cells. Choi, H.H., Jong, H.S., Park, J.H., Choi, S., Lee, J.W., Kim, T.Y., Otsuki, T., Namba, M., Bang, Y.J. Int. J. Oncol. (2003) [Pubmed]
  14. Mechanistic studies on protopanaxadiol, Rh2, and ginseng (Panax quinquefolius) extract induced cytotoxicity in intestinal Caco-2 cells. Popovich, D.G., Kitts, D.D. J. Biochem. Mol. Toxicol. (2004) [Pubmed]
  15. Ginsenosides of the protopanaxatriol group cause endothelium-dependent relaxation in the rat aorta. Kang, S.Y., Schini-Kerth, V.B., Kim, N.D. Life Sci. (1995) [Pubmed]
  16. A non-opioid mechanism in the inhibitory effect of ginseng saponins on electrically evoked contractions of guinea-pig ileum and mouse vas deferens. Watanabe, J., Oh, K.W., Kim, H.S., Takahashi, M., Kaneto, H. J. Pharmacobio-dyn. (1988) [Pubmed]
  17. Structure-function relationship exists for ginsenosides in reducing cell proliferation and inducing apoptosis in the human leukemia (THP-1) cell line. Popovich, D.G., Kitts, D.D. Arch. Biochem. Biophys. (2002) [Pubmed]
  18. Uptake and metabolism of ginsenoside Rh2 and its aglycon protopanaxadiol by Caco-2 cells. Xie, H.T., Wang, G.J., Chen, M., Jiang, X.L., Li, H., Lv, H., Huang, C.R., Wang, R., Roberts, M. Biol. Pharm. Bull. (2005) [Pubmed]
  19. In vitro inhibitory effect of protopanaxadiol ginsenosides on tumor necrosis factor (TNF)-alpha production and its modulation by known TNF-alpha antagonists. Cho, J.Y., Yoo, E.S., Baik, K.U., Park, M.H., Han, B.H. Planta Med. (2001) [Pubmed]
  20. In vivo antimetastatic action of ginseng protopanaxadiol saponins is based on their intestinal bacterial metabolites after oral administration. Wakabayashi, C., Hasegawa, H., Murata, J., Saiki, I. Oncol. Res. (1997) [Pubmed]
  21. Studies on the enzyme immunoassay of bio-active constituents in oriental medicinal drugs. VI. Enzyme immunoassay of ginsenoside Rb1 from Panax ginseng. Kanaoka, M., Kato, H., Shimada, F., Yano, S. Chem. Pharm. Bull. (1992) [Pubmed]
  22. Distinctive effect of ginseng saponins on development of morphine tolerance in guinea-pig ileum and mouse vas deferens. Watanabe, J., Takahashi, M., Kaneto, H. J. Pharmacobio-dyn. (1988) [Pubmed]
  23. Induction of apoptosis by a novel intestinal metabolite of ginseng saponin via cytochrome c-mediated activation of caspase-3 protease. Lee, S.J., Ko, W.G., Kim, J.H., Sung, J.H., Moon, C.K., Lee, B.H. Biochem. Pharmacol. (2000) [Pubmed]
  24. Transformation of ginsenosides Rb2 and Rc from Panax ginseng by food microorganisms. Chi, H., Kim, D.H., Ji, G.E. Biol. Pharm. Bull. (2005) [Pubmed]
  25. Double staining of ginsenosides by Western blotting using anti-ginsenoside Rb1 and Rg1 monoclonal antibodies. Fukuda, N., Tanaka, H., Shoyama, Y. Biol. Pharm. Bull. (2001) [Pubmed]
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