7-Polyacylated delphinidin 3,7-diglucosides from the blue flowers of Leschenaultia cv. Violet Lena.
The triacyl anthocyanins, Leschenaultia blue anthocyanins 1 and 2 (LBAs 1 and 2) were isolated from the blue flowers of Leschenaultia R. Br. cv. Violet Lena (Goodeniaceae), in which LBA 1 was present as a dominant pigment. The structure of LBA 1 was elucidated to be delphinidin 3-O-[6-O-(malonyl)-beta-D-glucopyranoside]-7-O-[6-O-(4-O-(6-O-(4-O-(beta-D-glucopyranosyl)-trans-caffeoyl)-beta-D-glucopyranosyl)-trans-caffeoyl)-beta-D-glucopyranoside] by application of chemical and spectroscopic methods. Since LAB 2 was isolated in small amount, its structure was tentatively assigned as either delphinidin 3-(malonylglucoside)-7-[(glucosyl-p-coumaroyl)-(glucosylcaffeoyl)-glucoside] or delphinidin 3-(malonyl-glucoside)-7-[(glucosyl-caffeoyl)(glucosyl-p-coumaroyl)-glucoside]. This is the first report of the occurrence of 7-polyacylated anthocyanins in the family of Goodeniaceae, although others have been found in the families of the Ranunculaceae, Campanulaceae, and Compositae. Moreover, delphinidin 3-glycoside-7-di-(glucosylcaffeoyl)-glucoside has been reported only in the flowers of Platycodon grandiflorum (Campanulaceae). From a chemotaxonomical viewpoint, the Goodeniaceae may be closely related to the Campanulaceae.
Saito
Norio
N
Hoshi University, Shinagawa, Tokyo 142-8501, Japan.
Tatsuzawa
Fumi
F
Yazaki
Yoshikazu
Y
Shigihara
Atsushi
A
Honda
Toshio
T
D000215:Acylation; D000872:Anthocyanins / Q000032:analysis* / Q000737:chemistry / Q000302:isolation & purification; D019659:Asteraceae / Q000737:chemistry*; D002109:Caffeic Acids / Q000032:analysis; D035264:Flowers / Q000737:chemistry*; D005960:Glucosides / Q000737:chemistry* / Q000302:isolation & purification; D008314:Malonates / Q000032:analysis; D008958:Models, Molecular; D008968:Molecular Conformation
D000872:Anthocyanins; D002109:Caffeic Acids; D005960:Glucosides; D008314:Malonates; C030290:malonic acid; C017185:delphinidin; C040048:caffeic acid