62(P27) (3S,5R,6R,7E,9R)-キウイイオノサイドおよびアクチニジオイオノサイドを前駆体としたバージニアタバコの数種のC_<11>,C_<13>-ノルイソプレノイド配糖体の絶対構造(ポスター発表の部)

概要

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C_<11> and C_<13>-norisoprenoid glucosides were obtained from Vieginia Tabacco about twenty years ago, but their chemical stereostructure have not been reported so far. In this study, the absoute structures of eight glucosides (3〜5,8,9,11), as well as several C_<13>-norisoprenoid (5a〜8a) have been determined by use of C-13 NMR substitution effects of alkanes, C-13 NMR glucosidation shifts rule, and reaction of allylcation. Furthermore, two glucosides of (3S,5R,6R,7E,9R)-kiwiionol from plant of Actinidiaceae, kiwiionoside (1) (its absolute structure has been determined using X-ray crystal analysis and other methods), actiriidioionoside (2) havebeen found as the precursors. The absolute structures of eight glucosides are clarified as follow; (6S,9R)-roseoside (3), (6R,9R)-3oxo-α-ionol β-D-glucopyranoside (4), (3S,5R,6S,9R)-5,6-epoxy-actinidioionoside (5), (3S,5R)-(-)-loliolide 3-O-β-D-glucopyranoside (8), (3S)-3-hydroxy-β-damascone 3-O-β-D-glucopyranoside (9), three glucosidic isomers of (3S, 9R)-megastigma-5-en-7-yne-3,9-diol (11a-c), and the C_<13>-norisoprenoid from volatile fraction as follow; (3S,5R,6S,9R)-5,6-epoxykiwiionol (5a), (3S,5R,6R,9R)-3,6-epoxy-7-megastigmene-5,9-diol (6a), and so on.
天然有機化合物討論会の論文
1998-08-31