Studies on the Chinese Crude Drug 'Shoma.' X. Three New Trinor-9,19-cyclolanostanol Xylosides, Cimicifugosides H-3, H-4 and H-6, from Cimicifuga Rhizome and Transformation of Cimicifugoside H-l into Cimicifugosides H-2, H-3 and H-4

摘要

Three trinor-triterpenol glycosides were isolated from a batch of commercial Cimicifuga Rhizome: cimicifugoside H-3 (1), C32H48Oa, mp 249—251 °C, [a]D -22.3°, cimicifugoside H-4 (2), C32H48O9, mp 265—267°C, [a]D -75.0°, and cimicifugoside H-6 (3), C32H48O10, mp 275—276°C, [?]D -64.3°. On the basis of chemical and spectral data, the structure of 1 was proposed to be ll^,24-dihydroxy-3/J-(j3-D-xylopyranosyloxy)-25,26,27-trinor-9,19-cyclolanost-7-ene-16,23-dione. Cimicifugoside H-4 (2), ll/?,16a,24ot-trihydroxy-30-(/S-D-xylopyranosyloxy)-25,26,27-trinor-9,19:16,24-dicyclolanost-7-en-23-one, seems to be generated from intramolecular aldol condensation between C-16 and C-24 of 1. Cimicifugoside H-6 (3) is the 15a-hydroxy derivative of 2. Cimicifugoside H-2 (5), which has already been obtained from cimicifugoside H-l (4) under an acidic condition, was found to give 1, 2 and an oc-hydroxy cnone (2a) under an alkaline condition.