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.

与中链饱和脂肪酸（癸酸）杂交的葡萄籽提取物（GSE）显示出比其亲本更高的亲脂性，抗氧化活性和抗增殖活性。单个杂交GSE衍生物的化学结构鉴定为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'' HPLC-MS ²和¹ H和¹³ C NMR分析5'-4-O-癸酰基表儿茶素没食子酸酯。为了抑制HepG2细胞的生长，杂交的GSE衍生物（EC ₅₀ = 44.38μg/ mL）比天然GSE（EC ₅₀）强（p <0.01）= 60.83μg/ mL）是由于增加了亲脂性。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，在存在杂交的GSE衍生物的情况下，凋亡细胞的百分比显着增加。此外，杂交的GSE衍生物能够诱导G1期细胞周期停滞。这项研究表明，杂交的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。