An unusual metabolite of cimicidol-3-O-beta-D-xyloside from Cimicifugae rhizoma by rat intestinal bacteria.
Cimicidol-3-O-beta-D-xyloside (1), one of the main components isolated from Cimicifugae rhizoma, is an active component with antiosteoporotic effect. The metabolism of 1 by rat intestinal bacteria was investigated, and two metabolites, 11beta-hydroxycimigenol (2) and foetidinol (3), were isolated and characterized by spectroscopic means including two-dimensional NMR. Furthermore, the structures of six intermediates in the bacterial incubation were proposed on the basis of LC/MS analyses, and the possible metabolic pathway of the formation of 2, which passes through a unique sequence including hydrolysis, hydroxylation, and reduction, is discussed in detail.
Li
Jian-Xin
JX
Key Lab of Analytical Chemistry for Life Science, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, PR China. lijxnju@nju.edu.cn
Li
Jun-Feng
JF
Chen
Song-Jie
SJ
Yu
Zhi-Yong
ZY
D000818:Animals; D001419:Bacteria / Q000378:metabolism*; D031885:Cimicifuga / Q000737:chemistry*; D005243:Feces / Q000737:chemistry / Q000382:microbiology; D005766:Gastrointestinal Contents / Q000382:microbiology*; D006027:Glycosides / Q000737:chemistry* / Q000302:isolation & purification* / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy / Q000379:methods / Q000592:standards; D008297:Male; D013058:Mass Spectrometry / Q000379:methods; D008968:Molecular Conformation; D051381:Rats; D017208:Rats, Wistar; D012015:Reference Standards; D013237:Stereoisomerism; D014315:Triterpenes / Q000737:chemistry* / Q000302:isolation & purification
C475454:22-hydroxycimigenol; D006027:Glycosides; D014315:Triterpenes; C532081:cimicidol-3-O-beta-D-xyloside