Three new cyclolanostanol xylosides were isolated from a batch of commercial Cimicifuga Rhizome, cimicifugoside H-1 (1), C_<35>H_<52>O_9,mp 260-262℃, [α]_D -43.5°, cimicifugoside H-2 (2), C_<35>H_<54>O_<10>, mp 227-229℃, [α]_D -38.8°, and cimicifugoside H-5 (3), C_<35>H_<52>O_<10>, mp 262-264℃, [α]_D -22.9°, together with known glycosides, actein and 27-deoxyactein. Their structures were determined on the basis of chemical and spectrometric evidence including an X-ray crystallographic analysis. The structure of cimicifugoside H-1 (1) was established as (20R, 24R)-24,25-epoxy-11β-hydroxy-3-β-(β-D-xylopyranosyloxy)-9,19-cyclolanost-7-ene-16,23-dione. Cimicifugoside H-5 (3) is the 15-hydroxylated derivative of 1. Since 1 changed into cimicifugoside H-2 (2) on treatment with p-toluenesulfonic acid, 2 has a 24R, 25-diol structure derived from 1 by opening its epoxy ring.
9, cimicifugoside H-1, cimicifugoside H-2, cimicifugoside H-5, Cimicifuga Rhizome, 19-cyclolanostanol, triterpenol glycoside
NCBI PubMed ID: 7553963Publication DOI: 10.1248/cpb.43.771Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Institutions: Faculty of Phrmaceutical Sciences, Hoshi University, Japan
Methods: 13C NMR, 1H NMR, EI-MS, IR, FAB-MS, X-ray, TLC, HPLC, UV, enzymatic digestion, CC, acetylation analysis
Found