ネジキLyonia ovalifolia DRUDE var.elliptica HAND.-MAZZ.の成分研究(第19報)Triterpenoid Glucoside, Lyofolic Acidの構造その3 Lyofoligenic Acidの構造

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The structure of lyofoligenic acid (II), obtained by acid hydrolysis of lyofolic acid^<2)> (I), was investigated in comparison with protolyofoligenic acid (III), which is the genuine aglycone of I and has already been chemically proved to possess the same carbon skeleton as cycloartenol^<5)>.(i) Acid c1eavage of the cyclopropane ring in III has been elucidated to give a 9(10→19)-abeo-lanost-5(10)-ene system (II) by preparing a cyclohexadienone derivative (VII).(ii) The conformation of 3α-OH in II and III was discussed on the basis of ^1Hnuclear magnetic resonance (^1H-NMR).(iii) Chemical behavior of the tertiary carboxylic function in II was examined and the 14α-COOH in II Was examined by using the shift reagent in the ^1H-NMR analysis of XX and by ^<13>C-NMR analysis of I, II, and III.(iv) The absolute configuration of hydroxyl groups at C-3 and C-24 was examined by applying the modified Horeau's method an XI and XIX, and both proved to be R. The structure II assigned to lyofoligenic acid is consistent with the result obtained by X-ray crystallographic study of XXII.
社団法人日本薬学会の論文
1975-08-25