Reinvestigation of absolute stereostructure of (-)-rosiridol: structures of monoterpene glycosides, rosiridin, rosiridosides A, B, and C, from Rhodiola sachalinensis.
Three new (-)-rosiridol glycosides, rosiridosides A, B, and C, were isolated from the roots of Rhodiola sachalinensis together with rosiridin [(-)-rosiridol 1-O-beta-D-glucopyranoside]. In the course of the structure elucidation of those new glycosides, the absolute configuration of the 4-position in (-)-rosiridol was reinvestigated. On the basis of the application of the modified Mosher's method for (-)- and (+)-rosiridol derivatives, the absolute configuration of the 4-position in (-)-rosiridol should be revised to be S orientation from the recently assigned R form, so that the absolute stereostructures of rosiridosides A, B, and C and rosiridin were determined.
Yoshikawa
Masayuki
M
Kyoto Pharmaceutical University, Kyoto, Japan. myoshika@mb.kyoto-phu.ac.jp
Nakamura
Seikou
S
Li
Xuezheng
X
Matsuda
Hisashi
H
D002236:Carbohydrate Conformation; D002851:Chromatography, High Pressure Liquid; D006026:Glycoside Hydrolases / Q000737:chemistry; D006027:Glycosides / Q000737:chemistry* / Q000302:isolation & purification; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D039821:Monoterpenes / Q000737:chemistry* / Q000302:isolation & purification; D009097:Multienzyme Complexes / Q000737:chemistry; D010084:Oxidation-Reduction; D018517:Plant Roots / Q000737:chemistry; D029771:Rhodiola / Q000737:chemistry*; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013055:Spectrophotometry, Infrared; D001617:beta-Glucosidase / Q000737:chemistry
D006027:Glycosides; D039821:Monoterpenes; D009097:Multienzyme Complexes; D006026:Glycoside Hydrolases; C039827:naringinase; D001617:beta-Glucosidase