High Molecular Weight Persimmon (Diospyros kaki L.) Proanthocyanidin: A Highly Galloylated, A-Linked Tannin with an Unusual Flavonol Terminal Unit, Myricetin
- 27 July 2010
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Agricultural and Food Chemistry
- Vol. 58 (16), 9033-9042
- https://doi.org/10.1021/jf102552b
Abstract
MALDI-TOF MS suggested that the high molecular weight proanthocyanidin (condensed tannin) from persimmon (Diospyros kaki L.) pulp comprised a heteropolyflavanol series with flavan-3-O-galloylated extenders, flavan-3-ol and flavonol terminal units, and A-type interflavan linkages. Thiolysis-HPLC-ESI-MS with DAD, electrochemical, and ESI-MS detection confirmed a previously unreported terminal unit, the flavonol myricetin, in addition to the typical flavan-3-ols catechin and epigallocatechin gallate. The extender units were epicatechin, epigallocatechin, (epi)gallocatechin-3-O-gallate, and (epi)catechin-3-O-gallate. The crude tannin had a high prodelphinidin content (65%) and a high degree of 3-O-galloylation (72%). The material was fractionated on Toyopearl TSK-HW-50-F to yield fractions distinguished by degree of polymerization (DP). Thiolysis suggested that the persimmon tannin was composed of polymers ranging from 7 to 20 kDa (DP 19−47), but sizes estimated by GPC were 50−70% smaller. The crude material was chemically degraded with acid to yield products that were amenable to NMR and ESI-MS analysis, which were used to establish for the first time that persimmon tannin has a mixture of B-type and A-type linkages.Keywords
This publication has 38 references indexed in Scilit:
- MALDI-TOF MS analysis of plant proanthocyanidinsJournal of Pharmaceutical and Biomedical Analysis, 2010
- INHIBITORY EFFECT OF WATER EXTRACT AND ITS MAIN CONTENTS OF PERSIMMON LEAVES ON STIMULUS-INDUCED SUPEROXIDE GENERATION IN HUMAN NEUTROPHILSJournal of Food Biochemistry, 2009
- Characterization of Polyphenolics in the Seed Coat of Black Jamapa Bean (Phaseolus vulgaris L.)Journal of Agricultural and Food Chemistry, 2005
- Proanthocyanidin Composition in the Seed Coat of Lentils (Lens culinarisL.)Journal of Agricultural and Food Chemistry, 2003
- Matrix-Assisted Laser Desorption/Ionization Time-of-Flight Mass Spectrometry of Heteropolyflavan-3-ols and Glucosylated Heteropolyflavans in Sorghum [Sorghum bicolor (L.) Moench]Journal of Agricultural and Food Chemistry, 2002
- The effects of diets, supplemented with either whole persimmon or phenol-free persimmon, on rats fed cholesterolFood Chemistry, 2000
- A-type proanthocyanidins from pericarp of Litchi chinensisPhytochemistry, 1998
- Prolongation of life span of stroke-prone spontaneously hypertensive rats(SHRSP) ingesting persimmon tannin.CHEMICAL & PHARMACEUTICAL BULLETIN, 1990
- Molecular weight profiles of proanthocyanidin polymersPhytochemistry, 1983
- Plant proanthocyanidins. Part II. Proanthocyanidin-A2 and its derivativesJournal of the Chemical Society, Perkin Transactions 1, 1974