葡萄籽油提取物的分子杂交：合成、结构表征和体外抗增殖活性。

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

机构信息

School of Food Science and Engineering, South China University of Technology, Guangzhou 510640, China.

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.

出版信息

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

DOI:10.1016/j.foodres.2020.109005

PMID:32247489

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-MS and H and C NMR. For growth inhibitory effect on HepG2 cells, hybridized GSE derivatives (EC = 44.38 μg/mL) were significantly (p < 0.01) stronger than natural GSE (EC = 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.

摘要

葡萄籽提取物（GSE）与中链饱和脂肪酸（癸酸）杂交后表现出比其亲本更高的亲脂性、抗氧化活性和抗增殖活性。通过 HPLC-MS 和 H 和 C NMR 鉴定了各个杂交 GSE 衍生物的化学结构分别为 3'-O-癸酰基儿茶素、3'-O-癸酰基表儿茶素、3'，5'-2-O-癸酰基表没食子儿茶素和 3'，4'，3″，5″-4-O-癸酰基表儿茶素没食子酸酯。对于对 HepG2 细胞的生长抑制作用，杂交 GSE 衍生物（EC = 44.38 μg/mL）由于亲脂性增加，明显强于天然 GSE（EC = 60.83 μg/mL）（p < 0.01）。通过流式细胞术进一步评估了 GSE 衍生物对 HepG2 细胞凋亡和细胞周期的影响。结果表明，在杂交 GSE 衍生物存在下，凋亡细胞的百分比明显增加。此外，杂交 GSE 衍生物能够诱导 G1 期细胞周期停滞。这项研究表明，杂交 GSE 衍生物是有效的亲脂性抗氧化剂，并显示出作为癌症辅助治疗的潜力。