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Short Paper | Special issue | Vol 99, No. 2, 2019, pp.1322-1329
Published online, 26th October, 2018
DOI: 10.3987/COM-18-S(F)47
Formation of an Aluminum Complex of 5-O-Caffeoylquinic Acid with Chiral Molecular Stacking under Vacuolar Condition

Kumi Yoshida,* Daisuke Ito, and Tadao Kondo

*Graduate School of Informatics, Nagoya University, Chikusa, Nagoya 464-8601, Japan


5-O-Caffeoylquinic acid (neochlorogenic acid, 5CQ) is an essential co-pigment for blue coloration of hydrangea. 5CQ solubilizes a water insoluble aluminum complex of 3-O-glucosyldelphinidin (Dp3G) to give a water-soluble blue complex, in which both Dp3G and 5CQ chelate a single Al3+ ion. However, its isomer, 3-O-caffeoylquinic acid (chlorogenic acid, 3CQ), has no such effect and does not give blue complex. It was clarified that 5CQ was complexed with Al3+ with a chiral molecular stacking under physiological vacuolar condition as aq. solution at pH 4.0. However, 3CQ did not give such complex with Al3+. The difference in aluminum complexation between the isomers may result from the difference configuration of 5-OH and 3-OH group in quinic acid.