Bioactive Apigenin-7-O-β-Glucoside and Rosmarinic Acid Molecules From Two Nepeta Species: Bioactivity-Guided Isolation, In Vitro Evaluations, Pharmacokinetic and In Silico Approaches as Metabolic Enzyme Inhibition Agents.
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Abstract
Introduction: In this study, apigenin-7-O-β-glucoside (AGL) was isolated from Nepeta nuda; also, rosmarinic acid (RA) was isolated from N. aristata and N. nuda.
Objectives: The aim of this study is to investigate the enzyme inhibitory, DNA protective, and antibacterial effects of AGL and RA isolated from two Nepeta species.
Material and methods: 1D and 2D NMR spectra and an MS chromatogram were recorded to identify AGL and RA. The antibacterial and DNA protection activities, enzyme inhibition, and kinetics investigated of AGL and RA. Molecular interactions, molecular dynamics (MD) simulations, molecular mechanics Poisson-Boltzmann surface area (MM-PBSA) calculations, density functional theory (DFT), molecular electrostatic potential (MEP) analyses, and prediction of activity spectra for substances (PASS) predictions for RA and AGL were investigated for the first time to evaluate the activity results.
Results: In this context, the inhibitory properties of AGL were higher in urease, α-amylase, and tyrosinase, whereas RA has a higher inhibitory activity on lipase, CA, and urease. In addition, AGL and RA showed effective antimicrobial activity against Staphylococcus aureus, while it also was effective DNA and deoxyribose protective activities. The stability of the complex formed by lipase, CA, and urease with RA and by tyrosinase and α-amylase with AGL was determined by MD simulations, and the energy results of RA were evaluated by MM-PBSA analysis. The DFT, MEP analysis, and PASS prediction showed that AGL and RA have a soft structure and can easily exchange electrons.
Conclusion: According to the results obtained from the current study, AGL and RA were explored as a drug model.
芹菜素-7- o -β-葡萄糖苷和迷迭香酸分子的生物活性：生物活性引导分离、体外评价、药代动力学和作为代谢酶抑制剂的计算机方法
摘要：本研究从荆芥中分离得到芹菜素-7- o -β-葡萄糖苷（AGL）；同时，从马塔塔和野田葵中分离到迷迭香酸（RA）。目的：研究从两种荆芥中分离得到的AGL和RA的酶抑制、DNA保护和抗菌作用。材料和方法：记录一维和二维核磁共振谱和质谱图，鉴定AGL和RA。研究了AGL和RA的抑菌和DNA保护活性、酶抑制和动力学。首次对RA和AGL的分子相互作用、分子动力学（MD）模拟、分子力学泊松-玻尔兹曼表面积（MM-PBSA）计算、密度泛函理论（DFT）、分子静电势（MEP）分析和物质活性谱预测（PASS）预测进行了研究，对活性结果进行了评价。结果：AGL对脲酶、α-淀粉酶和酪氨酸酶的抑制作用较强，而RA对脂肪酶、CA和脲酶的抑制作用较强。此外，AGL和RA对金黄色葡萄球菌具有有效的抗菌活性，同时具有有效的DNA和脱氧核糖保护活性。通过MD模拟确定了脂肪酶、CA、脲酶与RA、酪氨酸酶、α-淀粉酶与AGL形成复合物的稳定性，并通过MM-PBSA分析评价了RA的能量结果。DFT、MEP分析和PASS预测表明，AGL和RA具有较软的结构，易于交换电子。结论：根据本研究结果，AGL和RA可作为药物模型进行探索。
期刊介绍：
Phytochemical Analysis is devoted to the publication of original articles concerning the development, improvement, validation and/or extension of application of analytical methodology in the plant sciences. The spectrum of coverage is broad, encompassing methods and techniques relevant to the detection (including bio-screening), extraction, separation, purification, identification and quantification of compounds in plant biochemistry, plant cellular and molecular biology, plant biotechnology, the food sciences, agriculture and horticulture. The Journal publishes papers describing significant novelty in the analysis of whole plants (including algae), plant cells, tissues and organs, plant-derived extracts and plant products (including those which have been partially or completely refined for use in the food, agrochemical, pharmaceutical and related industries). All forms of physical, chemical, biochemical, spectroscopic, radiometric, electrometric, chromatographic, metabolomic and chemometric investigations of plant products (monomeric species as well as polymeric molecules such as nucleic acids, proteins, lipids and carbohydrates) are included within the remit of the Journal. Papers dealing with novel methods relating to areas such as data handling/ data mining in plant sciences will also be welcomed.
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