Tianjin Key Laboratory of Agricultural Animal Breeding and Healthy Husbandry, College of Animal Science and Veterinary Medicine, Tianjin Agricultural University, Tianjin 300384, China.
Department of Hepatopancreatobiliary Surgery, Tianjin Nankai Hospital, Tianjin 300100, China.
Molecules. 2021 Feb 26;26(5):1284. doi: 10.3390/molecules26051284.
Cytotoxic flavonoids of were investigated in this study. A novel flavonoid and twelve known flavonoids, including seven flavones (-), three flavanones (-), and three chalcones (-) were isolated from the leaves and twigs of . Chemical structures were elucidated by NMR combined with MS spectral analysis, and the new compound () was confirmed as 3',5'-dihydroxy-5,6,7,4'-tetramethoxyflavone. Furthermore, all the isolated flavonoids were evaluated for their cytotoxicities against murine melanoma cells (B16), and human breast cancer cells (MDA-MB-231) by CCK-8 assay. Among them, compounds , 13, and exhibited potent cytotoxic activities against B16 cell lines (IC = 3.87, 7.00 and 8.66 μg/mL, respectively). Compounds , 13, and displayed potent cytotoxicities against MDA-MB-231 cell lines (IC = 3.80, 5.95 and 7.89 μg/mL, respectively). According to the correlation of the structure and activity analysis, 5-hydroxyl and 8-methoxyl substituents of the flavone, 8-methoxyl substituent of the flavanone, and 3',5'-methoxyl substituents of the chalcone could be critical factors of the high cytotoxicity. The results indicated that the active flavonoids have potential to be developed as leading compounds for treating cancers.
本研究考察了 的细胞毒性类黄酮。从 的叶和枝中分离得到一种新的类黄酮和 12 种已知的类黄酮,包括 7 种黄酮类化合物(-)、3 种黄烷酮类化合物(-)和 3 种查尔酮类化合物(-)。通过 NMR 结合 MS 光谱分析阐明了化学结构,新化合物()被确认为 3',5'-二羟基-5,6,7,4'-四甲氧基黄酮。此外,所有分离得到的类黄酮均通过 CCK-8 测定法评估了其对小鼠黑色素瘤细胞(B16)和人乳腺癌细胞(MDA-MB-231)的细胞毒性。其中,化合物 、13 和 对 B16 细胞系表现出很强的细胞毒性(IC = 3.87、7.00 和 8.66 μg/mL)。化合物 、13 和 对 MDA-MB-231 细胞系表现出很强的细胞毒性(IC = 3.80、5.95 和 7.89 μg/mL)。根据结构与活性分析的相关性,黄酮类化合物的 5-羟基和 8-甲氧基取代基、黄烷酮类化合物的 8-甲氧基取代基和查尔酮类化合物的 3',5'-甲氧基取代基可能是高细胞毒性的关键因素。结果表明,具有活性的类黄酮有可能作为治疗癌症的先导化合物进行开发。