Studies on the Constituents of Cimicifuga Species. XXVII. Malonyl Cyclolanostanol Glycosides from the Underground Parts of Cimicifuga simplex WORMSK.

Four new cycloart-7-ene triterpenol arabinosides, bugbanosides C-F, were isolated from the underground parts of Cimicifuga simplex WORMSK. (Ranunculaceae). The structures were elucidated as 12β-acetoxy-3β, 15α, -24R, 25-tetrahydroxy-16, 23-dione-cycloart-7-ene 3-O-α-L-arabinopyranoside, 12β-acetoxy-24R, 25-epoxy-3β, 15α-dihydroxy-16, 23-dione-cycloart-7-ene 3-O-α-L-arabinopyranoside, 12β-acetoxy-24R, 25-epoxy-3β-hydroxy-16, 23-dione-cycloart-7-ene 3-O-α-L-arabinopyranoside, and 16, 23R: 16, 24S-diepoxy-3β, 12β, 15α, 25-tetrahydroxy-cycloart-7-ene 3-O-α-L-arabinopyranoside on the basis of spectral and chemical evidence. The circular dichroism (CD) of bugbanosides C-F showed strong negative maxima at 214-217 nm due to a cycloart-7-ene system, as well as other cycloart-7-ene triterpenes. The CD data showed to be useful in determining basic skeletons, including absolute stereostructures of cycloart-7-ene triterpenes.