Contribution of each caffeoyl residue of the pigment molecule of gentiodelphin to blue color development.
To clarify the function of each caffeoyl residue in the diacylated anthocyanin gentiodelphin, a pigment from the blue flower of Gentiana makinoi, two mono-deacyl derivatives were compared for both color development and stability. In neutral solution, 3,5-di-O-beta-D-glucopyranosyl-3'-O-(6-O-caffeoyl-beta-D- glucopyranosyl)delphinidin was both bluer and more stable than 3,3'-di-O-beta-D-glucopyranosyl-5-O-(6-O-caffeoyl-beta-D- glucopyranosyl)delphinidin. Conformational analysis of each derivative under acidic conditions revealed only the 3'-O-caffeoylglucopyranosyl derivative to demonstrate intramolecular stacking. Additionally, the acyl residue in the B-ring contributed more to blue color development than that in the A-ring.
Yoshida
K
K
School of Life Studies, Sugiyama Jogakuen University, Nagoya, Japan. yoshida@cic.nagoya-u.ac.jp
Toyama
Y
Y
Kameda
K
K
Kondo
T
T
D000215:Acylation; D000872:Anthocyanins / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism; D001578:Benzopyrans / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism; D005960:Glucosides / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism; D006863:Hydrogen-Ion Concentration; D009682:Magnetic Resonance Spectroscopy; D019684:Magnoliopsida / Q000737:chemistry* / Q000502:physiology; D008958:Models, Molecular; D016339:Spectrometry, Mass, Fast Atom Bombardment
C414933:3,5-di-O-glucopyranosyl-3'-O-(6-O-caffeoylglucopyranosyl)delphinidin; D000872:Anthocyanins; D001578:Benzopyrans; D005960:Glucosides; C414931:albireodelphin A; C414932:gentiodelphin