Laboratoire de Génie Chimique, Université de Toulouse, CNRS, INP, UPS, F-31062 Toulouse, France.
Laboratoire des Matériaux Molécules et Applications, Université Tunis Carthage, IPEST, La Marsa 2070, Tunisia.
Molecules. 2023 Mar 7;28(6):2419. doi: 10.3390/molecules28062419.
This work aimed to evaluate the biological activities of 20 flavones (M1 to M20) and discuss their structure-activity relationships. In vitro assays were established to assess their numerous biological activities (anti-α-amylase, anti-acetylcholinesterase, anti-xanthine oxidase, anti-superoxide dismutase, and anticancer cell lines (HCT-116, MCF7, OVCAR-3, IGROV-1, and SKOV-3 cells lines)). An in silico docking study was also established in order to find the relationship between the chemical structure and the biological activities. In vitro tests revealed that M5 and M13 were the most active in terms of anti-α-amylase activity (IC = 1.2 and 1.4 µM, respectively). M17 was an inhibitor of xanthine oxidase (XOD) and performed better than the reference (allopurinol), at IC = 0.9 µM. M7 presented interesting anti-inflammatory (IC = 38.5 µM), anti-supriode dismutase (anti-SOD) (IC = 31.5 µM), and anti-acetylcholinesterase (IC = 10.2 µM) activities. Those abilities were in concordance with its high scavenging activity in antioxidant ABTS and DPPH assays, at IC = 6.3 and 5.2 µM, respectively. Selectivity was detected regarding cytotoxic activity for those flavones. M1 (IC = 35.9 µM) was a specific inhibitor to the MCF7 cancer cell lines. M3 (IC = 44.7 µM) and M15 (IC = 45.6 µM) were particularly potent for the OVCAR-3 cell line. M14 (IC = 4.6 µM) contributed more clearly to inhibiting the colon cancer cell line (HCT116). M7 (IC = 15.6 µM) was especially active against the ovarian SKOV human cancer cell line. The results of the biological activities were supported by means of in silico molecular docking calculations. This investigation analyzed the contribution of the structure-activity of natural flavones in terms of their biological properties, which is important for their future application against diseases.
本工作旨在评估 20 种黄酮类化合物（M1 至 M20）的生物活性，并探讨其构效关系。建立了体外测定法来评估它们的多种生物活性（抗α-淀粉酶、抗乙酰胆碱酯酶、抗黄嘌呤氧化酶、抗超氧化物歧化酶和抗癌细胞系（HCT-116、MCF7、OVCAR-3、IGROV-1 和 SKOV-3 细胞系））。还建立了一个计算对接研究，以找到化学结构与生物活性之间的关系。体外试验表明，M5 和 M13 在抗α-淀粉酶活性方面最为活跃（IC = 1.2 和 1.4 µM）。M17 是黄嘌呤氧化酶（XOD）的抑制剂，其抑制作用优于对照物（别嘌呤醇），IC = 0.9 µM。M7 具有有趣的抗炎（IC = 38.5 µM）、抗超氧化物歧化酶（anti-SOD）（IC = 31.5 µM）和抗乙酰胆碱酯酶（IC = 10.2 µM）活性。这些能力与它在抗氧化 ABTS 和 DPPH 测定中的高清除活性一致，IC = 6.3 和 5.2 µM。这些黄酮类化合物的细胞毒性活性存在选择性。M1（IC = 35.9 µM）是 MCF7 癌细胞系的特异性抑制剂。M3（IC = 44.7 µM）和 M15（IC = 45.6 µM）对 OVCAR-3 细胞系特别有效。M14（IC = 4.6 µM）对抑制结肠癌（HCT116）细胞系的作用更为明显。M7（IC = 15.6 µM）对卵巢 SKOV 人癌细胞系特别有效。生物活性的结果得到了计算分子对接计算的支持。这项研究分析了天然黄酮类化合物的结构活性对其生物特性的贡献，这对于它们未来在疾病防治中的应用非常重要。
