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Lipophilized Grape Seed Proanthocyanidin Derivatives as Novel Antioxidants.
J Agric Food Chem. 2017 Mar 01; 65(8):1598-1605.JA

Abstract

Grape seed proanthocyanidin (GSP) is a natural food antioxidant. Natural proanthocyanidins (PC) in grape seed are usually polyhydroxy derivatives which exhibit hydrophilic character. GSP was modified structurally to improve its lipophilicity, expand its application in lipophilic media, and enhance its cellular absorption in vivo. Esterification of the water-soluble GSP was prepared by immobilized lipase Lipozyme TL IM with lauric acid, and their enhanced lipophilicity was confirmed by the 1-octanol/water partition coefficient. The presence of mono-, di-, and trilauroylated derivatives in GSP derivatives was confirmed by HPLC-MS-MS, and four lauroylated derivatives were identified as 3',5'-2-O-lauroyl epigallocatechin, 3'-O-lauroyl catechin, 3'-O-lauroyl epicatechin, and 3',3″,5″-3-O-lauroyl epicatechin gallate by NMR. GSP derivatives exhibited the highest 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity (IC50 of 41 μg/mL) compared to that of GSP, hydroxytoluene (BHT), and tert-butyl hydroquinone (TBHQ). The results suggest that GSP derivatives may be used as potential lipophilic antioxidants in the food industry.

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Publisher Full Text (DOI)

Authors+Show Affiliations

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

MeSH

AntioxidantsChromatography, High Pressure LiquidGrape Seed ExtractMass SpectrometryMolecular StructureProanthocyanidins

Pub Type(s)

Journal Article

Language

eng

PubMed ID

28211691

Citation

Chen, Mingshun, and Shujuan Yu. "Lipophilized Grape Seed Proanthocyanidin Derivatives as Novel Antioxidants." Journal of Agricultural and Food Chemistry, vol. 65, no. 8, 2017, pp. 1598-1605.
Chen M, Yu S. Lipophilized Grape Seed Proanthocyanidin Derivatives as Novel Antioxidants. J Agric Food Chem. 2017;65(8):1598-1605.
Chen, M., & Yu, S. (2017). Lipophilized Grape Seed Proanthocyanidin Derivatives as Novel Antioxidants. Journal of Agricultural and Food Chemistry, 65(8), 1598-1605. https://doi.org/10.1021/acs.jafc.6b05609
Chen M, Yu S. Lipophilized Grape Seed Proanthocyanidin Derivatives as Novel Antioxidants. J Agric Food Chem. 2017 Mar 1;65(8):1598-1605. PubMed PMID: 28211691.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Lipophilized Grape Seed Proanthocyanidin Derivatives as Novel Antioxidants. AU - Chen,Mingshun, AU - Yu,Shujuan, Y1 - 2017/02/17/ PY - 2017/2/18/pubmed PY - 2017/5/31/medline PY - 2017/2/18/entrez KW - antioxidant activity KW - esterification KW - grape seed proanthocyanidin KW - lipase SP - 1598 EP - 1605 JF - Journal of agricultural and food chemistry JO - J Agric Food Chem VL - 65 IS - 8 N2 - Grape seed proanthocyanidin (GSP) is a natural food antioxidant. Natural proanthocyanidins (PC) in grape seed are usually polyhydroxy derivatives which exhibit hydrophilic character. GSP was modified structurally to improve its lipophilicity, expand its application in lipophilic media, and enhance its cellular absorption in vivo. Esterification of the water-soluble GSP was prepared by immobilized lipase Lipozyme TL IM with lauric acid, and their enhanced lipophilicity was confirmed by the 1-octanol/water partition coefficient. The presence of mono-, di-, and trilauroylated derivatives in GSP derivatives was confirmed by HPLC-MS-MS, and four lauroylated derivatives were identified as 3',5'-2-O-lauroyl epigallocatechin, 3'-O-lauroyl catechin, 3'-O-lauroyl epicatechin, and 3',3″,5″-3-O-lauroyl epicatechin gallate by NMR. GSP derivatives exhibited the highest 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity (IC50 of 41 μg/mL) compared to that of GSP, hydroxytoluene (BHT), and tert-butyl hydroquinone (TBHQ). The results suggest that GSP derivatives may be used as potential lipophilic antioxidants in the food industry. SN - 1520-5118 UR - https://www.unboundmedicine.com/medline/citation/28211691/Lipophilized_Grape_Seed_Proanthocyanidin_Derivatives_as_Novel_Antioxidants_ L2 - https://doi.org/10.1021/acs.jafc.6b05609 DB - PRIME DP - Unbound Medicine ER -