title: Triacylated cyanidin 3-(3X-glucosylsambubioside)-5-glucosides from the flowers of Malcolmia maritima.
abstract: Three acylated cyanidin 3-(3(X)-glucosylsambubioside)-5-glucosides (1-3) and one non-acylated cyanidin 3-(3(X)-glucosylsambubioside)-5-glucoside (4) were isolated from the purple-violet or violet flowers and purple stems of Malcolmia maritima (L.) R. Br (the Cruciferae), and their structures were determined by chemical and spectroscopic methods. In the flowers of this plant, pigment 1 was determined to be cyanidin 3-O-[2-O-(2-O-(trans-sinapoyl)-3-O-(beta-D-glucopyranosyl)-beta-D-xylopyranosyl)-6-O-(trans-p-coumaroyl)-beta-D-glucopyranoside]-5-O-[6-O-(malonyl)-(beta-D-glucopyranoside) as a major pigment, and a minor pigment 2 was determined to be the cis-p-coumaroyl isomer of pigment 1. In the stems, pigment 3 was determined to be cyanidin 3-O-[2-O-(2-O-(trans-sinapoyl)-3-O-(beta-D-glucopyranosyl)-beta-D-xylopyranosyl)-6-O-(trans-p-coumaroyl)-beta-d-glucopyranoside]-5-O-(beta-D-glucopyranoside) as a major anthocyanin, and also a non-acylated anthocyanin, cyanidin 3-O-[2-O-(3-O-(beta-D-glucopyranosyl)-beta-D-xylopyranosyl)-beta-D-glucopyranoside]-5-O-(beta-D-glucopyranoside) was determined to be a minor pigment (pigment 4). In this study, it was established that the acylation-enzymes of malonic acid has important roles for the acylation of 5-glucose residues of these anthocyanins in the flower-tissues of M. maritima; however, the similar enzymatic reactions seemed to be inhibited or lacking in the stem-tissues.
authors.affiliation: Faculty of Horticulture, Minami-Kyushu University, Takanabe, Miyazaki 884-0003, Japan. fumi@nankyudai.ac.jp
authors.forename: Fumi
authors.initials: F
authors.lastname: Tatsuzawa
authors.forename: Norio
authors.initials: N
authors.lastname: Saito
authors.forename: Kenjiro
authors.initials: K
authors.lastname: Toki
authors.forename: Koichi
authors.initials: K
authors.lastname: Shinoda
authors.forename: Atsushi
authors.initials: A
authors.lastname: Shigihara
authors.forename: Toshio
authors.initials: T
authors.lastname: Honda
mesh_terms: D000872:Anthocyanins / Q000737:chemistry / Q000302:isolation & purification*; D019607:Brassicaceae / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D035264:Flowers / Q000737:chemistry*; D005960:Glucosides / Q000737:chemistry / Q000302:isolation & purification*; D015394:Molecular Structure
chemical_list: D000872:Anthocyanins; D005960:Glucosides; C017154:cyanidin