Steroid Saponins and Sapogenins of Underground Parts of Trillium kamtschaticum PALL. III. On the Structure of a Novel Type of Steroid Glycoside, Trillenoside A, an 18-Norspirostanol Oligoside

抄録

A glycoside, mp 209-220° (decomp), [α] D-142°, C₄₇H₇₀O₂₄, named trillenoside A (I), was isolated from the rhizomes of Trillium kamtschaticum PALL (Liliaceae). The structure of its aglycone (designated trillenogenin, II), mp 250-251°, [α] D-198°, C₂₆H₃₆O₈, was determined by X-ray crystallographic analysis of the tetraacetyl monobrosyl derivative, mp 242-244° (dec.), [α] D-112°, C₄₀H₄₇BrO₁₄S, and I was characterized as 15-oxo-18-nor-25 R-spirosta-5, 13-diene-1β, 3β, 21, 23α, 24β-pentaol 1-O-β-D-apiofuranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-α-L-arabinopyranoside. I is thus a novel type of steroid glycoside, noteworthy in that the aglycone is an 18-norspirostane derivative having an enone system in the D-ring and hydroxyl groups at C₂₁ and in the F-ring, and also in that the sugar moiety is a branched-chain tetrasaccharide containing apiose.