Ginsenoside structure

Ginsenosides with a few exceptions share a similar basic structure, consisting of a saturated 1,2-cyclopentanoperhydrophenanthrene (sterane or gonane) steroid nucleus. They are classified into two groups by the skeleton of aglycones, namely dammarane-type and oleanane-type. Ginsenosides... 

Cui, M., Song, F., Liu, Z., and Liu, S. (2001). Metal ion adducts in the structural analysis of ginsenosides by electrospray ionization with multi-stage mass spectrometry. Rapid Commun. Mass Spectrom. 15, 586-595. 

Popovich, D. G., and Kitts, D. D. (2002). Structure-function relationship exists for ginsenosides in reducing cell proliferation and inducing apoptosis in the human leukaemia (THP-1) cell line. Arch. Biochem. Biophys. 406,1-8. 

Sanada, S. and Shoji, J. (1978). Studies on the saponins of ginseng. III. Structures of ginsenoside-Rb3 and 20-glucoginsenoside-Rf. Chem. Pharm. Bull. 26,1694-1697. 

Zhou, J., Wu, M., Taniyasu, S., Besso, H., Tanaka, O., Saruwatari, Y., and Fuwa, T. (1981). Dammarane-saponins of Sanchi-ginseng, roots of Panax notoginseng (Burk.) F. H. Chen (Araliaceae) Structures of new saponins, notoginsenosides-Rl and -R2, and identification of ginsenosides-Rg2 and -Rhi. Chem. Pharm. Bull. 29, 2844-2850. 

Fig. 2.2 Structures of common ginsenosides. The core damarane structure common to ginsenosides is shown along with the carbon skeletons of the 20(S)-protopanaxadiol and 20(S)-protopanaxatriol ginsenosides. The sugar decorations of the most common ginsenosides are indicated in the table below the structures. Legend Ara(/), arabinose (furanose form) Ara(p), arabinose (pyranose form) Glc, glucose...

Fig. 5.1 Chemical structures of ginsenosides. Ginsenosides can be separated into protopanaxadi-ols (a) or protopanaxatriols (b), depending on the presence or absence of a substituent group at carbon 6. Individual ginsenosides differ according to their sugar moieties, as indicated by Ri and R2 in the table...

Hao M, Zhao Y, Chen P et al (2008) Structure-activity relationship and substrate-dependent phenomena in effects of ginsenosides on activities of drug-metabolizing P450 enzymes. PloS... 

Fig. 7.1 Chemical structures of six major ginsenosides - (a) protopanaxadiol and (b) protopanax-atriol...

Figure 10 Chemical structures of ginsenosides. Abbreviations, glc, P-D-glucose rha, M-L-rhamnose ara, ot-L-arabinose p, pyranose /, furanose.

The structural elucidation of the ginsenosides was challenging, but thanks to the dedicated work of Prof. Shibata (Tokyo University)2 and of Prof. Tanaka (Hiroshima University)3 their full stereochemistry is known. The ginsenosides are saponins of the dammaran class and are of two different types ... 

Y. Nagai, O. Tanaka, and S. Shibata, Chemical studies on the Oriental plant drugs — XXTV Structure of ginsenoside Rgj, a neutral saponin of ginseng root. Tetrahedron 27, 811, 1971. 

Ginsenosides belong to a family of steroids and share their structural characteristics. They can traverse cell membranes freely similar to steroids. Moreover, their presence has been demonstrated within cells, particularly the nucleus. Steroid hormone action, steroids that bind nuclear receptors, are thought to affect primarily the transcription of mRNA and subsequent protein synthesis. Intracellular steroid-binding proteins present possible attractive targets for ginsenosides. 

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