Dimeric alkaloids of secodine-type from Amsonia tabernaemontana roots

Phytochemistry
1975.0

Abstract

Preparative chromatography of the fruit extract of Acanthopanax divaricatus (Sieb. et Zucc.) Seeman revealed the presence of two anthocyanins, one of which was a new pigment. On complete acid hydrolysis, the new anthocyanin yielded delphinidin, xylose and galactose. The absorption spectrum (in 0.01 % MeOH-HCl) of the glycoside showed A,,, (nm) 283 and 532 and a bathochromic shift of 13 nm by the addition of AlCl, indicating the presence of a free o-dihydroxylic grouping in the B-ring. The ratios of Eu.v and E440/Evis.,,, were 58 and 22 ;~~$?~~~~~ These values suggest that the pig;ent is the 3 glycoside [l]. By H,Oz oxidation the glycoside yielded the disaccharide which was identified paper chromatographically as lathyrose. On partial acid hydrolysis delphinidin 3-galactoside was detected as an intermediate. The pigment must therefore be delphinidin 3-xylosylgalactoside (3 lathyroside), which has not been reported before. Recently, cyanidin 3-lathyroside has been found in the ripe berries of Aralia elata [2] and its variety canescens [3], and A. cordata [2]. Therefore, the glycosidic similarity of the anthocyaninsin the plants in the family Araliaceae may be of systematic interest.

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