Molecular hybridization of grape seed extract: Synthesis, structural characterization and anti-proliferative activity in vitro

Caiyu Lei; Xiangyi Tang; He Li; Hualei Chen; Shujuan Yu

doi:10.1016/j.foodres.2020.109005

Molecular hybridization of grape seed extract: Synthesis, structural characterization and anti-proliferative activity in vitro

Food Res Int. 2020 May:131:109005. doi: 10.1016/j.foodres.2020.109005. Epub 2020 Jan 19.

Authors

Caiyu Lei¹, Xiangyi Tang¹, He Li¹, Hualei Chen¹, Shujuan Yu²

Affiliations

¹ School of Food Science and Engineering, South China University of Technology, Guangzhou 510640, China.
² 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. Electronic address: shujuanyu8@gmail.com.

PMID: 32247489
DOI: 10.1016/j.foodres.2020.109005

Abstract

The grape seed extract (GSE) hybridized with medium-chain saturated fatty acids (decanoic acid) exhibited higher lipophilicity, antioxidant activity, and anti-proliferative activity than its parents. The chemical structures of individual hybridized GSE derivatives were identified as 3'-O-decanoyl catechin, 3'-O-decanoyl epicatechin, 3', 5'-2-O-decanoyl epigallocatechin, and 3', 4', 3″, 5″-4-O-decanoyl epicatechin gallate by HPLC-MS² and ¹H and ¹³C NMR. For growth inhibitory effect on HepG2 cells, hybridized GSE derivatives (EC₅₀ = 44.38 μg/mL) were significantly (p < 0.01) stronger than natural GSE (EC₅₀ = 60.83 μg/mL) due to increased lipophilicity. The effects of GSE derivatives on apoptosis and cell cycle in HepG2 cells were further evaluated by flow cytometry. The results showed that the percentage of apoptotic cells increased markedly in the presence of hybridized GSE derivatives. Moreover, hybridized GSE derivatives were capable of inducing cell cycle arrest in G1 phase. This research suggests that hybridized GSE derivatives are effective lipophilic antioxidants and show the potential as adjuvant therapy for cancer.

Keywords: Anti-proliferation; Antioxidant; Grape seed extract; HepG2 cell; Hybridization.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antineoplastic Agents, Phytogenic / pharmacology*
Antioxidants / chemistry
Apoptosis / drug effects
Catechin / analogs & derivatives
Cell Proliferation / drug effects*
Chromatography, High Pressure Liquid
Decanoic Acids / chemistry
Grape Seed Extract / chemistry*
Grape Seed Extract / metabolism*
Hep G2 Cells
Humans
Mass Spectrometry

Substances

Antineoplastic Agents, Phytogenic
Antioxidants
Decanoic Acids
Grape Seed Extract
epicatechin 5-gallate
decanoic acid
Catechin
gallocatechol