104109-45-7Relevant articles and documents
Studies on the Constituents of Aceraceae Plants. VI. Revised Stereochemistry of (-)-Centrolobol, and New Glycosides from Acer nikoense
Nagai, Masahiro,Kenmochi, Naoki,Fujita, Masao,Furukawa, Naoko,Inoue, Takao
, p. 1056 - 1060 (2007/10/02)
Two diarylheptanoid glycosides, named aceroside VII (8), C25H34O8, mp 144-145 deg C, 15D -28.4 deg, and aceroside VIII (9), C30H42O12, 15D -64.8 deg were isolated from the stem bark of Acer nikoense MAXIM (Aceraceae).On acid hydrolysis 8 yielded (-)-centrolobol (10) and glucose, while 9, on partial hydrolysis, gave 8 and apiose.Acerosides VII (8) and VIII (9) were determined to be the 3-O-β-D-glucopyranoside and the 3-O-β-apiofuranosyl-(1->6)-β-D-glucopyranoside of (-)-centrolobol (10), respectively, on the basis of carbon-13 nuclear magnetic resonance (13C-NMR) spectral analyses and additional chemical data.The absolute configuration S for (-)-centrolobol (10) has been claimed, but the authors propose its revision to R(-) on the basis of Brewster's empirical rule on the correlation between absolute configuration and optical rotation.The stereochemistries of some compounds related to 10 such as acerogenin A (1) and (-)-centrolobin should also be revised.At the same time, partial revision of the 13C-NMR signal assignments for acerosides III (3) and VI (4) is also necessary.Keywords - Acer nikoense; diarylheptanoid; R(-)-centrolobol; aceroside (VII, VIII); Brewster empirical rule; absolute configuration revision
