2 DIASTEREOMERIC 3-OXO-ALPHA-IONOL BETA-D-GLUCOSIDES FROM RASPBERRY FRUIT

被引：142

作者：

PABST, A

BARRON, D

SEMON, E

SCHREIER, P

机构：

[1] UNIV WURZBURG, LEHRSTUHL LEBENSMITTELCHEM, AM HUBLAND, W-8700 WURZBURG, GERMANY

[2] UNIV JOSEPH FOURIER GRENOBLE I, PHARMACOGNOSIE LAB, UFR PHARM, F-38706 LA TRONCHE, FRANCE

[3] INRA, RECH AROMES LAB, F-21034 DIJON, FRANCE

来源：

PHYTOCHEMISTRY | 1992年 / 31卷 / 05期

关键词：

RUBUS-IDAEUS; ROSACEAE; RASPBERRY FRUIT; 3-OXO-ALPHA-IONOL GLUCOSIDES; 4-[3'(BETA-D-GLUCOPYRANOSYLOXY)-1'-BUTENYL]-3,5,5-TRIMETHYL-2-CYCLOHEXEN-1-ONE;

D O I：

10.1016/0031-9422(92)83121-E

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

From a methanolic extract of raspberry fruit two 3'-O-beta-D-glucopyranosides of diastereomeric 4-(3'-hydroxy-1'-butenyl)-3,5,5-trimethyl-2-cyclohexen-1-one(3-oxo-alpha-ionol)were isolated by adsorption chromatography on XAD-2 followed by LC on Sephadex LH-20, MPLC on RP-18, and flash chromatography on silica gel as well as by HPLC on diol and RP-18 phases. Their structures were determined by H-1 and C-13 NMR spectroscopy. The absolute configurations of the diastereomeric aglycones were established as (6R,9R) and (6R,9S), respectively, by CD correlation as well as H-1 NMR analysis of their corresponding (R)-(-)-alpha-phenylpropionic acid esters.

引用

页码：1649 / 1652

页数：4

共 17 条

[1] OXIDATION OF SECONDARY ALCOHOLS IN DIETHYL ETHER WITH AQUEOUS CHROMIC ACID - CONVENIENT PROCEDURE FOR PREPARATION OF KETONES IN HIGH EPIMERIC PURITY [J].