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Characterization of Lipophilized Monomeric and Oligomeric Grape Seed Flavan-3-ol Derivatives.
J Agric Food Chem. 2017 Oct 11; 65(40):8875-8883.JA

Abstract

Grape seed proanthocyanidins, composed of flavan-3-ols of different degrees of polymerization, are natural food antioxidants. Flavan-3-ols in grape seed are usually polyhydroxy derivatives which exhibit hydrophilic character. Monomeric and oligomeric flavan-3-ols were modified structurally to improve their lipophilicity, expand their application in lipophilic media, and enhance their cellular absorption in the body. The esterification of the water-soluble flavan-3-ols was prepared by Lipozyme TL IM with lauric acid, and their enhanced lipophilicity was confirmed by a 1-octanol/water partition coefficient. The chemical structures of monomeric and oligomeric flavan-3-ol derivatives, identified by HPLC-MS-MS and 1H and 13C NMR, were 3'-O-lauroyl catechin, 3'-O-lauroyl epicatechin, 3',5'-2-O-lauroyl epigallocatechin, 3',3″,5″-3-O-lauroyl epicatechin gallate, 3',3″-2-O-lauroyl procyanidin A2, 3',3″-2-O-lauroyl procyanidin B1, and 3',3″,3‴-3-O-lauroyl procyanidin C1. Flavan-3-ol derivatives exhibited the highest 1,1-diphenyl-2-picrylhydrazyl and 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) radical scavenging activities compared to that of parent flavan-3-ols, butylated hydroxytoluene and tert-butyl hydroquinone. The results suggest that flavan-3-ol derivatives may be used as potential lipophilic antioxidants in the food industry.

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Authors+Show Affiliations

Chen M
School of Food Science and Engineering, ‡Guangdong Province Key Laboratory for Green Processing of Natural Products and Product Safety, South China University of Technology , Guangzhou 510640, China.
Yu S
School of Food Science and Engineering, ‡Guangdong Province Key Laboratory for Green Processing of Natural Products and Product Safety, South China University of Technology , Guangzhou 510640, China.

MeSH

AntioxidantsFlavonoidsMass SpectrometryMolecular StructurePlant ExtractsSeedsVitis

Pub Type(s)

Journal Article

Language

eng

PubMed ID

28936872

Citation

Chen, Mingshun, and Shujuan Yu. "Characterization of Lipophilized Monomeric and Oligomeric Grape Seed Flavan-3-ol Derivatives." Journal of Agricultural and Food Chemistry, vol. 65, no. 40, 2017, pp. 8875-8883.
Chen M, Yu S. Characterization of Lipophilized Monomeric and Oligomeric Grape Seed Flavan-3-ol Derivatives. J Agric Food Chem. 2017;65(40):8875-8883.
Chen, M., & Yu, S. (2017). Characterization of Lipophilized Monomeric and Oligomeric Grape Seed Flavan-3-ol Derivatives. Journal of Agricultural and Food Chemistry, 65(40), 8875-8883. https://doi.org/10.1021/acs.jafc.7b03530
Chen M, Yu S. Characterization of Lipophilized Monomeric and Oligomeric Grape Seed Flavan-3-ol Derivatives. J Agric Food Chem. 2017 Oct 11;65(40):8875-8883. PubMed PMID: 28936872.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Characterization of Lipophilized Monomeric and Oligomeric Grape Seed Flavan-3-ol Derivatives. AU - Chen,Mingshun, AU - Yu,Shujuan, Y1 - 2017/09/29/ PY - 2017/9/25/pubmed PY - 2017/12/15/medline PY - 2017/9/23/entrez KW - antioxidant activity KW - esterification KW - flavan-3-ols KW - lipase KW - lipophilicity SP - 8875 EP - 8883 JF - Journal of agricultural and food chemistry JO - J Agric Food Chem VL - 65 IS - 40 N2 - Grape seed proanthocyanidins, composed of flavan-3-ols of different degrees of polymerization, are natural food antioxidants. Flavan-3-ols in grape seed are usually polyhydroxy derivatives which exhibit hydrophilic character. Monomeric and oligomeric flavan-3-ols were modified structurally to improve their lipophilicity, expand their application in lipophilic media, and enhance their cellular absorption in the body. The esterification of the water-soluble flavan-3-ols was prepared by Lipozyme TL IM with lauric acid, and their enhanced lipophilicity was confirmed by a 1-octanol/water partition coefficient. The chemical structures of monomeric and oligomeric flavan-3-ol derivatives, identified by HPLC-MS-MS and 1H and 13C NMR, were 3'-O-lauroyl catechin, 3'-O-lauroyl epicatechin, 3',5'-2-O-lauroyl epigallocatechin, 3',3″,5″-3-O-lauroyl epicatechin gallate, 3',3″-2-O-lauroyl procyanidin A2, 3',3″-2-O-lauroyl procyanidin B1, and 3',3″,3‴-3-O-lauroyl procyanidin C1. Flavan-3-ol derivatives exhibited the highest 1,1-diphenyl-2-picrylhydrazyl and 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) radical scavenging activities compared to that of parent flavan-3-ols, butylated hydroxytoluene and tert-butyl hydroquinone. The results suggest that flavan-3-ol derivatives may be used as potential lipophilic antioxidants in the food industry. SN - 1520-5118 UR - https://www.unboundmedicine.com/medline/citation/28936872/Characterization_of_Lipophilized_Monomeric_and_Oligomeric_Grape_Seed_Flavan_3_ol_Derivatives_ DB - PRIME DP - Unbound Medicine ER -