Studies on the Constituents of Aceraceae Plants. VII. : Diarylheptanoids from Acer griseum and Acer triflorum

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A diarylheptanoid glycoside, named aceroside IX (1), C_<30>H_<40>O_<12>, [α]_D -63.5°, was isolated from the stem bark of Acer griseum and A. triflorum. Another diarylheptanoid glycoside, named aceroside X (2), C_<25>H_<31>O_8,mp 121°, [α]^<21>_D -29.7°, and catechin were isolated from the stem bark of A. griseum and detected by thin layer chromatography in the case of A. triflorum. On acid hydrolysis 1 yielded a new diarylheptanoid, acerogenin G (3), C_<19>H_<22>O_3,which was identified as a ketonic derivative of (-)-centrolobol (5), and sugars, glucose and apiose. On partial hydrolysis, 1 gave aceroside X (2) and apiose. The sugar moiety of aceroside IX is bound to the phenolic hydroxyl at C-4" of acerogenin G (3) from the results of mass spectral analysis of 3 and its monomethyl ether (6), the latter of which was formed on methylation of 1 followed by acid hydrolysis. Acerosides (1) and X (2) were determined to be the 4"-O-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside and the 4"-O-β-D-glucopyranoside of acerogenin G, respectively, on the basis of carbon-13 nuclear magnetic resonancence spectral analyses in comparison with the spectrum of aceroside VIII (7).
1990-06-25