Oxidation and epimerization of epigallocatechin in banana fruits.
To examine the metabolism of proanthocyanidins in banana fruit, (-)-epigallocatechin was treated with the homogenate of the fruit flesh to yield (-)-gallocatechin and an oxidation product, 1-(3,4,5-trihydroxyphenyl)-3-(2,4,6-trihydroxyphenyl)-2-hydroxy-1-propan one. The latter product is a stable form of a key intermediate in the oxidative metabolism of flavan-3-ols, and is also related to the biogenesis of A-type proanthocyanidins. In addition, treatment of the reaction mixture with o-phenylenediamine afforded monomeric and dimeric phenazine derivatives generated by condensation with the o-quinone form of the oxidation product.
Tanaka
T
T
School of Pharmaceutical Sciences, Nagasaki University, Japan.
Kondou
K
K
Kouno
I
I
D001711:Biotransformation; D002392:Catechin / Q000031:analogs & derivatives*; D005419:Flavonoids / Q000737:chemistry / Q000378:metabolism*; D005638:Fruit / Q000378:metabolism*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D005419:Flavonoids; D002392:Catechin; C057580:gallocatechol