X-ray Structure Investigation of 20-O-beta-D-glucopyranosyl-20(S)-protopanaxadiol

作者：Zhou Wei; Li JiYang; Feng MeiQing; Zhou Pei^*

来源：Journal of Chemical Crystallography, 2009, 39(2): 99-103.

DOI：10.1007/s10870-008-9431-x

• Protopanaxadiol
• Ginsenoside
• Metabolite
• Crystal structure

20-O-beta-D-glucopyranosyl-20(S)-protopanaxadiol (I) has been isolated as a metabolite of ginseng saponins by Paecilomyces bainier. The crystal structure of (I) was also investigated by single crystal X-ray diffraction analysis. It crystallizes in the monoclinic space group P2(1), with a = 15.99 2 (3) angstrom, b = 11.960 (19) angstrom, c = 20.127 (3) angstrom, beta = 101.85 (4)degrees, and V = 3767.5 (11) angstrom(3), Z = 4, R(int) = 0.1129, omega R(F(2)) = 0.1749, F(000) = 1,448. The title compound is a dammarane-type triterpenoid, and the four rings of this compound connect with each other in trans characteristics, with the three-six-membered rings in chair conformation and the five-membered ring adopting envelope one. A beta-D-glucopyranosyl group and a 2-methyl-2-pentenyl group connect to C20 of S configuration. The space symmetrical motif is adopted and each packing unit-cell contains two symmetrical compound (I) molecules and four H(2)O molecules. The hydrogen-bonding (both intra-and inter-molecular) interactions play a major role in this structural association.

• 出版日期2009-2
• 单位复旦大学