Parthiban A, Sachithanandam V, Lalitha P, Elumalai Dhanasekar, Asha Radhakrishnan Nandini, Jeyakumar Thayalaraj Christopher, Muthukumaran J, Jain Monika, Jayabal Kamalraja, Mageswaran T, Sridhar R, Purvaja R, Ramesh R
National Centre for Sustainable Coastal Management, Ministry of Environment, Forest and Climate Change, Anna University Campus, Chennai, Tamil Nadu, India.
Department of Chemistry, Pondicherry University, Puducherry, India.
J Biomol Struct Dyn. 2023 Apr;41(7):2848-2860. doi: 10.1080/07391102.2022.2039771. Epub 2022 Feb 22.
The flavonoid based 7-hydroxy flavone (PubChem CID: 5281894; molecular formula: CHO) molecule has been isolated for the first time from the methanolic extract from the leaves of L. in the tropical mangrove ecosystem of Andaman and Nicobar Islands (ANI), India. The molecular structure of bioactive compound was characterized by spectroscopic analysis, including FT-IR, H, C NMR spectroscopy and ESI-HRMS and elucidated as 7-hydroxy flavone. An anticancer activity of isolated 7-hydroxy flavone was evaluated by study against two different human cancer cell lines namely, HeLa (cervical cells) and MDA-MB231 (breast cells) and they exhibited promising anticancer activity with IC values are 22.5602 ± 0.21 µg/mL and 3.86474 ± 0.35 µg/mL, respectively. The antioxidant property of 7-hydroxy flavone at a standard concentration of 50 µg, was found to be (IC) 5.5486 ± 0.81 µg/mL. In summary, this investigation provides evidence that 7-hydroxy flavone exhibits both anticancer and antioxidant properties. Meanwhile, the antimicrobial activity ability of 7-hydroxy flavone were also evaluated using three Gram positive and two Gram negative strain exhibited no antimicrobial activities. Density-functional theory (DFT) studies confirm the structure is global minima in the PES, from the optimized geometry FMO and MESP map analyzed. Further, the molecular docking and molecular dynamics simulation studies result shows that 7-hydroxy flavone has the better binding ability with anti-apoptotic Bcl-2 protein with the estimated free energy of binding of -6.3 kcal/mol. This bioactive compound may be act as drug candidate for treating various kinds of cancers. HighlightsA 7-hydroxy flavone molecule has been isolated from .The isolated pure compound was subjected to spectral analysis such as FT-IR, H NMR, C NMR spectral data and HRMS analysis for skeleton of the molecule.The anticancer activity of 7-hydroxy flavone studied against Cervical (HeLa) cancer cell lines and breast (MDA-MB231) cancer cell lines with the IC values of 22.5602 ± 0.21 µg/mL and 3.86474 ± 0.35 µg/mL), respectively.The antioxidant properties of 7-hydroxy flavone were found to be (IC) 5.5486 ± 0.81 µg/mL at a standard concentration of 50 µg.DFT, molecular docking and MD simulation results explained that 7-hydroxy flavone could be the most promising candidate to inhibit the function of anti-apoptotic Bcl-2 protein in cancerous cell.Communicated by Ramaswamy H. Sarma.
基于类黄酮的7-羟基黄酮（PubChem CID：5281894；分子式：CHO）分子首次从印度安达曼和尼科巴群岛（ANI）热带红树林生态系统中L.叶片的甲醇提取物中分离出来。通过光谱分析对生物活性化合物的分子结构进行了表征，包括傅里叶变换红外光谱（FT-IR）、氢核磁共振（H NMR）、碳核磁共振（C NMR）光谱以及电喷雾高分辨质谱（ESI-HRMS），并确定其为7-羟基黄酮。通过针对两种不同的人类癌细胞系，即HeLa（宫颈癌细胞）和MDA-MB231（乳腺癌细胞）的研究，评估了分离出的7-羟基黄酮的抗癌活性，它们表现出有前景的抗癌活性，IC值分别为22.5602±0.21μg/mL和3.86474±0.35μg/mL。发现在标准浓度为50μg时，7-羟基黄酮的抗氧化性能（IC）为5.5486±0.81μg/mL。总之，本研究提供了证据表明7-羟基黄酮具有抗癌和抗氧化特性。同时，使用三种革兰氏阳性菌和两种革兰氏阴性菌评估了7-羟基黄酮的抗菌活性，结果显示其无抗菌活性。密度泛函理论（DFT）研究证实，从优化的几何结构、前线分子轨道（FMO）和分子静电势（MESP）图分析可知，该结构在势能面上是全局最小值。此外，分子对接和分子动力学模拟研究结果表明，7-羟基黄酮与抗凋亡Bcl-2蛋白具有更好的结合能力，估计结合自由能为-6.3 kcal/mol。这种生物活性化合物可能作为治疗各种癌症的候选药物。重点内容：从……中分离出了一个7-羟基黄酮分子。对分离出的纯化合物进行了光谱分析，如FT-IR、H NMR、C NMR光谱数据和HRMS分析，以确定分子骨架。研究了7-羟基黄酮对宫颈（HeLa）癌细胞系和乳腺（MDA-MB231）癌细胞系的抗癌活性，IC值分别为22.5602±0.21μg/mL和3.86474±0.35μg/mL。发现在标准浓度为50μg时，7-羟基黄酮的抗氧化性能（IC）为5.5486±0.81μg/mL。DFT、分子对接和分子动力学模拟结果表明，7-羟基黄酮可能是抑制癌细胞中抗凋亡Bcl-2蛋白功能的最有前景的候选物。由Ramaswamy H. Sarma传达。
