Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, Qassim University, Buraydah 51452, Saudi Arabia.
Department of Pharmacognosy, Faculty of Pharmacy, Al-Azhar University, Cairo 11371, Egypt.
Molecules. 2021 Sep 26;26(19):5827. doi: 10.3390/molecules26195827.
Different chromatographic methods including reversed-phase HPLC led to the isolation and purification of three -methylated flavonoids; 5,4'-dihydroxy-3,6,7-tri--methyl flavone (penduletin) (), 5,3'-dihydroxy-3,6,7,4',5'-penta--methyl flavone (), and 5-hydroxy-3,6,7,3',4',5'-hexa--methyl flavone () from roots. Additionlly, four flavonoid glycosides; kampferol 7---L-rhamnopyranoside (), isorhamnetin-3---D-glucopyranoside (), quercetin 7---L-rhamnopyranoside (), and kampferol 3, 7-di---L-rhamnopyranoside () along with benzyl---D-glucopyranoside () were successfully isolated. Complete structure characterization of these compounds was assigned based on NMR spectroscopic data, MS analyses, and comparison with the literature. The -methyl protons and carbons of the three -methylated flavonoids (-) were unambiguously assigned based on 2D NMR data. The occurrence of compounds , , , and in is was reported here for the first time. Compound was acetylated at 5-OH position to give 5--acetyl-3,6,7,3',4',5'-hexa--methyl flavone (). Compound exhibited the highest cytotoxic activity against MCF 7, A2780, and HT29 cancer cell lines with IC values at 2.17 µM, 0.53 µM, and 2.16 µM, respectively, and was 2-9 folds more selective against tested cancer cell lines compared to the normal human fetal lung fibroblasts (MRC5). It also doubled MCF 7 apoptotic populations and caused G cell cycle arrest. The acetylated compound exhibited cytotoxic activity against MCF 7 and HT29 cancer cell lines with IC values at 2.19 µM and 3.18 µM, respectively, and was 6-8 folds more cytotoxic to tested cancer cell lines compared to the MRC5 cells.
从 根部分离并纯化得到三种三甲基化黄酮类化合物：5,4'-二羟基-3,6,7-三甲氧基黄酮（penduletin）（）、5,3'-二羟基-3,6,7,4',5'-五甲氧基黄酮（）和 5-羟基-3,6,7,3',4',5'-六甲氧基黄酮（）。此外，还成功分离到四种黄酮苷类化合物：山柰酚 7-O-L-鼠李吡喃糖苷（）、异鼠李素-3-O-β-D-吡喃葡萄糖苷（）、槲皮素 7-O-L-鼠李吡喃糖苷（）和山柰酚 3,7-二-O-L-鼠李吡喃糖苷（）以及苯甲基-β-D-吡喃葡萄糖苷（）。根据 NMR 谱、MS 分析和与文献比较，对这些化合物的结构进行了全面表征。基于二维 NMR 数据，明确分配了三个三甲基化黄酮（-）的 -甲基质子和碳信号。化合物 、 、 、和 首次在 中报道。化合物 于 5-OH 位乙酰化得到 5-O-乙酰基-3,6,7,3',4',5'-六甲氧基黄酮（）。化合物 对 MCF-7、A2780 和 HT29 癌细胞系表现出最高的细胞毒性活性，IC 值分别为 2.17 µM、0.53 µM 和 2.16 µM，与正常人类胎儿肺成纤维细胞（MRC5）相比，对测试的癌细胞系具有 2-9 倍的选择性。它还使 MCF-7 凋亡细胞群加倍，并导致 G 细胞周期停滞。乙酰化化合物 对 MCF-7 和 HT29 癌细胞系的细胞毒性活性的 IC 值分别为 2.19 µM 和 3.18 µM，与 MRC5 细胞相比，对测试的癌细胞系的细胞毒性活性高 6-8 倍。
