Lipophilized Grape Seed Proanthocyanidin Derivatives as Novel Antioxidants

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 (IC 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.

Addition of lipophilic grape seed proanthocyanidin effectively reduces acrylamide formation

“…LGSP was prepared according to our previous study . Briefly, GSP, lauric acid, lipozyme TLIM (Novo Nordisk, Denmark), and ethanol were mixed in screw‐capped glass bottles and incubated at 45 °C for 12 h. Then, the enzyme was removed and the product was concentrated to obtain LGSP.…”

“…Grape seed proanthocyanidins (GSPs) are the main polyphenols in grape seed and oligomers or polymers of the polyhydroxy flavan‐3‐ol units containing (+)‐catechin, (−)‐epicatechin, (−)‐epicatechin‐3‐O‐gallate, and (−)‐epigallocatechin . Lipophilic grape seed proanthocyanidin (LGSP), synthesized by enzymatic esterification of GSP, is a natural lipophilic antioxidant which exhibits higher antioxidant activity than GSP . The main components of LGSP have been identified and demonstrated to be non‐toxic .…”

“…Lipophilic grape seed proanthocyanidin (LGSP), synthesized by enzymatic esterification of GSP, is a natural lipophilic antioxidant which exhibits higher antioxidant activity than GSP . The main components of LGSP have been identified and demonstrated to be non‐toxic . At present, many synthetic lipid antioxidants are restricted in the food industry because of their potential carcinogenicity and toxicity .…”

“…The main components of LGSP have been identified and demonstrated to be non‐toxic . At present, many synthetic lipid antioxidants are restricted in the food industry because of their potential carcinogenicity and toxicity . Therefore, people have turned their attention to natural lipophilic antioxidants.…”

Cosmetic Serum Containing Grape (Vitis vinifera L.) Seed Extract Phytosome: Formulation and In Vitro Penetration Study

“…This condition leads to the need of structural modification to increase lipophilicity. 7 One of strategies to enhance drug absorption and penetration of active ingredients from plant extracts is using the phytosome system. The application of phytosome technology to topical dosage form has proven to be effective for herbal medicine delivery into the skin.…”