Phytochemical Analysis and Evaluation of Antioxidant and Antimicrobial Properties of Essential Oils and Seed Extracts of Anethum graveolens from Southern Morocco: In Vitro and In Silico Approach for a Natural Alternative to Synthetic Preservatives

Pharmaceuticals Pub Date : 2024-07-01 DOI:10.3390/ph17070862
Nadia Hadi, A. Drioiche, El Moumen Bouchra, Soukayna Baammi, Abdelaaty Abdelaziz Shahat, I. Tagnaout, Mohamed Radi, Fidaous Remok, A. Bouzoubaa, T. Zair
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Abstract

Anethum graveolens is an aromatic plant traditionally used as an antispasmodic and carminative. The objective of this study is to analyze the chemical composition of the essential oils and extracts obtained from seeds gathered in Errachidia, southern Morocco. Additionally, the antioxidant and antimicrobial properties of these oils and extracts will be evaluated. GC-MS analysis of the EO isolated by hydrodistillation revealed that its main compounds were E-anethole (38.13%), estragole (29.32%), fenchone (17.21%), and α-pinene (7.37%). The phenolic components were extracted using the methods of decoction and Soxhlet. The assay of the phenolic compounds showed that A. graveolens seeds contained considerable amounts of polyphenols, flavonoids, and condensed tannins, with variable levels depending on the extract analyzed. HPLC/UV-ESI-MS analyses performed on the decoction revealed a structural diversity of the molecules present in this extract, the most important of which were umbelliferone (12.35%), 3-hydroxyflavone (11.23%), rosmanol (8.95%), biotin (8.36%), emmotin H (4.91%), and coumarin (4.21%). The antioxidant activity, as determined by three techniques (DPPH•, FRAP, and CAT), demonstrated that the essential oils (EOs) and extracts had a potent capacity to counteract detrimental free radicals, control the generation of reactive oxygen species, and mitigate oxidative damages. The antimicrobial activity of the Eos and extracts was carried out in a liquid medium against five strains (E. cloacae, K. pneumoniae, E. coli, S. aureus, and S. epidermidis) and four candidiasis (C. albicans, C. dubliniensis, C. tropicalis, and C. parapsilosis) and Aspergillus niger. The results showed the effectiveness of the EOs compared to the aqueous, ethanolic, and decoction extracts against most of the microorganisms tested. In addition, the ethanolic extract showed antifungal activity that was distinguished from that of the other extracts. The antimicrobial efficacy of the essential oils under study can primarily be attributed to the synergistic interactions among its three principal constituents (E-anethole, estragole, and fenchone). Furthermore, molecular docking and molecular dynamics simulation results reveal significant interactions and stability between the selected bioactive compounds and different target proteins involved in antimicrobial and antioxidant activities. Compounds like 3-hydroxyflavone, emmotin H, trans-caftaric acid, methyl rosmarinate, 1-caffeoyl-beta-D-glucose, and kaempferol exhibited better binding energies with the explored proteins, indicating their potential as antimicrobial and antioxidant agents. Finally, our findings emphasize the significance of A. graveolens seeds as a promising reservoir of advantageous health compounds that can serve as organic substitutes for the presently employed synthetic preservatives.
摩洛哥南部 Anethum graveolens 植物精油和种子提取物的植物化学分析及抗氧化和抗菌特性评估:体外和硅学方法,天然替代合成防腐剂
Anethum graveolens 是一种芳香植物,传统上被用作解痉和催眠药。本研究的目的是分析从摩洛哥南部 Errachidia 采集的种子中提取的精油和提取物的化学成分。此外,还将评估这些精油和提取物的抗氧化和抗菌特性。通过水蒸馏分离出的环氧乙烷的气相色谱-质谱分析表明,其主要化合物为乙内酯(38.13%)、雌甾醇(29.32%)、葑酮(17.21%)和α-蒎烯(7.37%)。酚类成分采用煎煮法和索氏提取法提取。酚类化合物的检测结果表明,A. graveolens 种子中含有大量的多酚、黄酮类化合物和缩合单宁酸,其含量因分析的提取物而异。对煎煮液进行的 HPLC/UV-ESI-MS 分析显示,这种提取物中的分子结构多种多样,其中最重要的是伞形酮(12.35%)、3-羟基黄酮(11.23%)、玫瑰酚(8.95%)、生物素(8.36%)、大黄素 H(4.91%)和香豆素(4.21%)。通过三种技术(DPPH-、FRAP 和 CAT)测定的抗氧化活性表明,精油(EOs)和提取物具有抵消有害自由基、控制活性氧生成和减轻氧化损伤的强大能力。在液体培养基中,对五种菌株(泄殖腔杆菌、肺炎双球菌、大肠杆菌、金黄色葡萄球菌和表皮葡萄球菌)和四种念珠菌(白念珠菌、杜比利念珠菌、热带念珠菌和副丝状念珠菌)以及黑曲霉进行了萃取物和提取物的抗菌活性测试。结果表明,与水提取物、乙醇提取物和煎煮提取物相比,环氧乙烷对大多数受测微生物都有效。此外,乙醇提取物显示出的抗真菌活性与其他提取物不同。所研究的精油的抗菌功效主要归功于其三种主要成分(乙内酯、雌甾醇和葑酮)之间的协同作用。此外,分子对接和分子动力学模拟结果表明,所选生物活性化合物与参与抗菌和抗氧化活动的不同靶蛋白之间具有显著的相互作用和稳定性。3-hydroxyflavone, emmotin H, trans-caftaric acid, methyl rosmarinate, 1-caffeoyl-beta-D-glucose, and kaempferol 等化合物与所研究的蛋白质具有更好的结合能,表明它们具有作为抗菌剂和抗氧化剂的潜力。最后,我们的研究结果强调了A. graveolens种子的重要性,它是一个很有前途的有益健康化合物宝库,可以作为目前使用的合成防腐剂的有机替代品。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
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