Antioxidant properties of catechins and proanthocyanidins: effect of polymerisation, galloylation and glycosylation.
A range of catechins and oligomeric procyanidins was purified by high performance liquid chromatography (HPLC) from grape seed, apple skin, lentil and almond flesh. Catechins, galloylated epicatechin, glycosylated catechin, procyanidin dimers, galloylated dimers, trimer, and tetramer species were all identified, purified and quantified by HPLC, LC-MS and NMR. The antioxidant properties of these compounds were assessed using two methods: (a) inhibition of ascorbate/iron-induced peroxidation of phosphatidylcholine liposomes; (b) scavenging of the radical cation of 2,2'-azinobis(3-ethyl-benzothiazoline-6-sulphonate) (ABTS) relative to the water-soluble vitamin E analogue Trolox C (expressed as Trolox C equivalent antioxidant capacity, TEAC). Antioxidant activity in the lipid phase decreased with polymerisation in contrast with antioxidant action in the aqueous phase which increased from monomer to trimer and then decreased from trimer to tetramer. Galloylation of catechin and dimeric procyanidins decreased lipid phase and increased aqueous phase antioxidant activity. Glycosylation of catechin demonstrated decreased activity in both phases.
Plumb
G W
GW
Biochemistry Department, Institute of Food Research, Norwich Research Park, Colney, UK. geoff.plumb@bbsrc.ac.uk
De Pascual-Teresa
S
S
Santos-Buelga
C
C
Cheynier
V
V
Williamson
G
G
D000872:Anthocyanins / Q000378:metabolism / Q000494:pharmacology*; D000975:Antioxidants / Q000378:metabolism / Q000494:pharmacology*; D052160:Benzothiazoles; D044946:Biflavonoids; D002392:Catechin / Q000031:analogs & derivatives / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D002839:Chromans; D019281:Dimerization; D005638:Fruit; D005707:Gallic Acid / Q000378:metabolism*; D006031:Glycosylation; D020128:Inhibitory Concentration 50; D015227:Lipid Peroxidation / Q000187:drug effects; D008081:Liposomes / Q000187:drug effects / Q000378:metabolism; D010713:Phosphatidylcholines / Q000378:metabolism; D010944:Plants; D011108:Polymers / Q000378:metabolism*; D044945:Proanthocyanidins; D012639:Seeds; D012995:Solubility; D013451:Sulfonic Acids / Q000378:metabolism
D000872:Anthocyanins; D000975:Antioxidants; D052160:Benzothiazoles; D044946:Biflavonoids; D002839:Chromans; D008081:Liposomes; D010713:Phosphatidylcholines; D011108:Polymers; D044945:Proanthocyanidins; D013451:Sulfonic Acids; C013221:proanthocyanidin; C002502:2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid; C017674:procyanidin; D005707:Gallic Acid; D002392:Catechin; C010643:6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid