Using LC/HRESI-MS/MS技术进行筛查,对Jatropha integerrima Jacq. 提取物进行植物化学特性表征,以及体外抗氧化和细胞毒性潜力研究。
LC/HRESI-MS/MS screening, phytochemical characterization, and in vitro antioxidant and cytotoxic potential of Jatropha integerrima Jacq. extracts.
发表日期:2023 Sep 03
作者:
Mohamed Marzouk, Shimaa M Khalifa, Amal H Ahmed, Ahmed M Metwaly, Hala Sh Mohammed, Hanan A A Taie
来源:
BIOORGANIC CHEMISTRY
摘要:
避免合成药物可能的危险副作用,本研究旨在从红花(J. integerrima)叶片和花朵提取物中鉴定天然抗氧化剂和抗肿瘤剂。通过高效快速的UPLC/ESI-qTOF-HRMS/MS筛选,已经鉴定了30种类黄酮类化合物,即12种黄酮醇、6种黄酮、3种二氢黄酮醇、4种花青素(花朵)、2种二氢黄酮醇和3种异黄酮。此外,首次从叶提取物中鉴定出了六种主要多酚类化合物,并通过HRESI-MS和NMR分析确定了它们的结构,它们分别是芸香苷(rhoifolin, 1)、槲皮素-8-C-β-D-4C1-葡萄糖苷(vitexin, 2)、异齐墩果糖苷(isoorientin, 3)、6,6″-二-C-β-D-4C1-葡萄糖苷基-间二氢芸香素(Jatrophenol-I, 4)、(E)-对香豆酸甲酯(5)以及(E)-香豆酸甲酯(6)。采用DPPH、还原能力、FRAP和ABTS自由基清除试验评估了提取物和主要纯化化合物的体外抗氧化活性,同时在艾氏癌细胞(EACC)上评估了它们的体外细胞毒性。花提取物和化合物3展示了最强的抗氧化和细胞毒性效果。在低浓度(25 μg/mL)下,它们显示出最高的DPPH自由基清除能力(79.63 ± 0.42%和76.20 ± 0.35%),相对于BHA(在100 μg/mL时为91.44 ± 0.29%)。在吸光度参数方面,它们表现出较高的还原能力(1.402 ± 0.025%和1.178 ± 0.019%),高于BHA(在100 μg/mL时为0.975 ± 0.013%)。类似地,它们表现出较高的FRAP(1427 ± 9.61和1377 ± 13.61 μmol Trolox/100 g)和最高的ABTS活性(80.19 ± 0.55%和68.38 ± 0.19%),这些活性高于BHA(在100 μg/mL时为88.42 ± 0.24%)。此外,所有样品在相同浓度(100 μg/mL)下均显示出明显的细胞毒性,尤其是花提取物和化合物3对EACC的生存率有相对较高的影响(分别为81.12 ± 0.24%和77.21 ± 0.76%),相对于文西ristine作为参考药物的生存率(90.64 ± 0.39%)。根据研究结果,这些提取物和化合物可以被视为具有强大抗氧化和细胞毒性的天然药物,尤其是花提取物和异齐墩果糖苷(3),可以为它们在制药业中的潜在应用提供新的洞察。版权所有 © 2023 Elsevier Inc.保留所有权利。
Avoiding the probable dangerous side effects of synthetic drugs, this study aims the identification of natural antioxidant and antitumor agents from J. integerrima leaf and floral extracts. A highly efficient and fast UPLC/ESI-qTOF-HRMS/MS screening has led to characterization of 30 flavonoids, i.e. 12 flavonols, 6 flavones, 3 dihydroflavonols, 4 anthocyanins (flower), 2 dihydroflavonols, and 3 isoflavones from both J. integerrima extracts. In addition, six major polyphenols were identified for the first time from leaf extract, and their structures were established as apigenin 7-O-β-d-neohesperidoside (rhoifolin, 1), apigenin 8-C-β-D-4C1-glucopyranoside (vitexin, 2), luteolin 6-C-β-D-4C1-glucopyranoside (isoorientin, 3), 6,6″-di-C-β-D-4C1-glucopyranosyl-methylene-biapigenin (Jatrophenol-I, 4), (E)-p-coumaric acid methyl ester (5), and (E)-ferulic acid methyl ester (6) with HRESI-MS and NMR analyses. The in vitro antioxidant activity of both extracts and major pure isolates was decided using DPPH, reducing power capability, FRAP, and ABTS radical scavenging assays, and their in vitro cytotoxicity was evaluated on Ehrlich ascites carcinoma cells (EACC), as well.The flower extract and compound 3 have shown the strongest antioxidant and cytotoxic effects. At low concentrations (25 µg/mL), they showed the highest DPPH radical scavenging ability (79.63 ± 0.42 and 76.20 ± 0.35%) regarding BHA (91.44 ± 0.29% at 100 µg/mL). In the parameter of absorbance, they exhibited higher reducing power ability (1.402 ± 0.025 and 1.178 ± 0.019%) than that of BHA (0.975 ± 0.013 at 100 µg/mL). Similarly, they proved superior FRAP (1427 ± 9.61 and 1377 ± 13.61 µmol Trolox/ 100 g) and highest ABTS activity (80.19 ± 0.55 and 68.38 ± 0.19%), which are higher activities compared to BHA (88.42 ± 0.24% at 100 µg/mL). Furthermore, all samples gave noticeable cytotoxicity at the same concentration (100 µg/mL), especially the flower extract and compound 3 which showed a relatively high effect on the viability of EACC (81.12 ± 0.24 and 77.21 ± 0.76 %, respectively) relative to vincristine reference drug (90.64 ± 0.39 %). Based on the findings, the extracts and isolates can be considered as potent antioxidant and cytotoxic natural agents, especially flower extract and isoorientin (3), which may supply novel insight into their likely application in pharmaceutical industries.Copyright © 2023 Elsevier Inc. All rights reserved.