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-1 into Cimicifugosides H-2, H-3 and H-4.

Three trinor-triterpenol glycosides were isolated from a batch of commercial Cimicifuga Rhizome : cimicifugoside H-3 (1), C32H48O9, mp 249-251 °C, [α]D -22.3°, cimicifugoside H-4 (2), C32H48O9, mp 265-267 °C, [α]D -75.0°, and cimicifugoside H-6 (3), C32H<48>O10, mp 275-276 °C, [α]D -64.3°, On the basis of chemical and spectral data, the structure of 1 was proposed to be 11β, 24-dihydroxy-3β-(β-D-xylopyranosyloxy)-25, 26, 27-trinor-9, 19-cyclolanost-7-ene-16, 23-dione. Cimicifugoside H-4 (2), 11β, 16α, 24α-trihydroxy-3β-(β-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 15α-hydroxy derivative of 2. Cimicifugoside H-2 (5), which has already been obtained from cimicifugoside H-1 (4) under an acidic condition, was found to give 1, 2 and an α-hydroxy enone (2a) under an alkaline condition.

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