title: Noncovalent interaction of dietary polyphenols with common human plasma proteins.
abstract: Common human plasma proteins (CHPP), also called blood proteins, are proteins found in blood plasma. The molecular structure/property-affinity relationships of dietary polyphenols noncovalently binding to CHPP were investigated by comparing the binding constants obtained from the fluorescence titration method. An additional methoxy group in flavonoids increased their binding affinities for CHPP by 1.05 to 72.27 times. The hydroxylation on the 4' position (ring B) of flavones and flavonols and the 5 position (ring A) of isoflavones weakened the binding affinities; however, the hydroxylation on other positions of flavonoids slightly enhanced or little affected the binding affinities for CHPP. The glycosylation of flavonoids weakened or slightly affected the affinities for CHPP by 1 order of magnitude. The hydrogenation of the C2═C3 double bond of flavone, 6-hydroxyflavone, 6-methoxyflavone and myricetin decreased the binding affinities about 10.02 to 17.82 times. The galloylation of catechins significantly improved the binding affinities with CHPP about 10 to 1000 times. The esterification of gallic acid increased its binding affinity. The binding affinities with CHPP were strongly influenced by the structural differences of dietary polyphenols. Polyphenols with higher affinities for purified HSA also showed stronger affinities with CHPP. The hydrophobic force played an important role in binding interaction between polyphenols and CHPP.
authors.affiliation: Department of Biology, College of Life & Environment Science, Shanghai Normal University , 100 Guilin Road, Shanghai 200234, PR China. jianboxiao@yahoo.com
authors.forename: Jianbo
authors.initials: J
authors.lastname: Xiao
authors.forename: Yaru
authors.initials: Y
authors.lastname: Zhao
authors.forename: Hui
authors.initials: H
authors.lastname: Wang
authors.forename: Yongming
authors.initials: Y
authors.lastname: Yuan
authors.forename: Fan
authors.initials: F
authors.lastname: Yang
authors.forename: Chao
authors.initials: C
authors.lastname: Zhang
authors.forename: Koichiro
authors.initials: K
authors.lastname: Yamamoto
mesh_terms: D001798:Blood Proteins / Q000378:metabolism*; D004032:Diet; D004951:Esterification; D005419:Flavonoids / Q000737:chemistry / Q000378:metabolism; D006031:Glycosylation; D006801:Humans; D006865:Hydrogenation; D006900:Hydroxylation; D059808:Polyphenols / Q000737:chemistry* / Q000378:metabolism*; D011485:Protein Binding; D012709:Serum Albumin / Q000378:metabolism; D013329:Structure-Activity Relationship
chemical_list: D001798:Blood Proteins; D005419:Flavonoids; D059808:Polyphenols; D012709:Serum Albumin