Chemically engineered essential oils prepared through thiocyanation under solvent-free conditions: chemical and bioactivity alteration

IF 4.8 3区化学 Q1 CHEMISTRY, MEDICINAL

Natural Products and Bioprospecting Pub Date : 2024-06-01 DOI:10.1007/s13659-024-00456-w

Liz E. Lescano, Mario O. Salazar, Ricardo L. E. Furlan

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Abstract

The generation of chemically engineered essential oils (CEEOs) prepared from bi-heteroatomic reactions using ammonium thiocyanate as a source of bioactive compounds is described. The impact of the reaction on the chemical composition of the mixtures was qualitatively demonstrated through GC–MS, utilizing univariate and multivariate analysis. The reaction transformed most of the components in the natural mixtures, thereby expanding the chemical diversity of the mixtures. Changes in inhibition properties between natural and CEEOs were demonstrated through acetylcholinesterase TLC autography, resulting in a threefold increase in the number of positive events due to the modification process. The chemically engineered Origanum vulgare L. essential oil was subjected to bioguided fractionation, leading to the discovery of four new active compounds with similar or higher potency than eserine against the enzyme. The results suggest that the directed chemical transformation of essential oils can be a valuable strategy for discovering new acetylcholinesterase (AChE) inhibitors.

Graphical Abstract

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在无溶剂条件下通过硫氰酸法制备的化学工程精油：化学和生物活性的改变。

本文介绍了利用硫氰酸铵作为生物活性化合物来源，通过双原子反应制备化学工程精油（CEEOs）的过程。通过气相色谱-质谱（GC-MS），利用单变量和多变量分析，定性分析了反应对混合物化学成分的影响。反应改变了天然混合物中的大部分成分，从而扩大了混合物的化学多样性。通过乙酰胆碱酯酶 TLC 自显影，证明了天然和 CEEOs 之间抑制特性的变化，结果显示，由于改性过程，阳性事件的数量增加了三倍。对经过化学工程改造的牛至精油进行了生物导向分馏，发现了四种新的活性化合物，它们对乙酰胆碱酯酶的效力与艾丝氨酸相似或更高。研究结果表明，对精油进行定向化学转化是发现新乙酰胆碱酯酶（AChE）抑制剂的重要策略。

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来源期刊

Natural Products and Bioprospecting CHEMISTRY, MEDICINAL-

CiteScore

8.30

自引率

2.10%

发文量

审稿时长

13 weeks

期刊介绍： Natural Products and Bioprospecting serves as an international forum for essential research on natural products and focuses on, but is not limited to, the following aspects: Natural products: isolation and structure elucidation Natural products: synthesis Biological evaluation of biologically active natural products Bioorganic and medicinal chemistry Biosynthesis and microbiological transformation Fermentation and plant tissue cultures Bioprospecting of natural products from natural resources All research articles published in this journal have undergone rigorous peer review. In addition to original research articles, Natural Products and Bioprospecting publishes reviews and short communications, aiming to rapidly disseminate the research results of timely interest, and comprehensive reviews of emerging topics in all the areas of natural products. It is also an open access journal, which provides free access to its articles to anyone, anywhere.