Journal
TETRAHEDRON
Volume 70, Issue 45, Pages 8657-8664Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2014.09.046
Keywords
Blue flower color development; Circular dichroism; Tecophilaea cyanocrocus; Tecophilin; Molecular stacking; Polyacylated anthocyanin
Categories
Funding
- Ministry of Education, Science, Sports, Culture, Technology, Japan [16370021, 16GS0206, 18032037, 19039012]
- Global COE in Chemistry, Nagoya University
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The pigment, tecophilin, in blue flowers of Tecophilaea cyanocrocus was isolated and the structure was determined to be 3-O-(6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranosyl)-7-O-(6-O-(4-O-(2-O-(4-O-beta-D-glucopyranosyl-(E)-caffeoyl)-6-O-(4-O-beta-D-glucopyranosyl-(E)-caffeoyl)-beta-D-glucopyranosyl)-(E)-caffeoyl)-beta-D-glucopyranosyl)delphinidin. The reproduction experiment of the same color as petals according to the results of chemical analysis and measurement of vacuolar pH of blue cells clarified that the blue color solely develops by tecophilin without interaction of metal ions nor co-pigments. H-1 NMR analysis and CD spectrum indicate the co-existence of clockwise intermolecular self-association of the delphinidin nuclei and intramolecular pi-pi stacking between the chromophore and caffeoyl residues to derive bathochromic shift of the absorption spectrum and stabilize the color by preventing hydration reaction. (C) 2014 Elsevier Ltd. All rights reserved.
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