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

doi:10.1007/s13659-024-00456-w

应用天然产物 ›› 2024, Vol. 14 ›› Issue (5): 35-35.DOI: 10.1007/s13659-024-00456-w

• ORIGINAL ARTICLES • 上一篇下一篇

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

Liz E. Lescano¹, Mario O. Salazar^1,2, Ricardo L. E. Furlan^1,2

1. Farmacognosia, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario (UNR), Suipacha 531, 2000, Rosario, Argentina;
2. Consejo Nacional de Investigaciones Científicas y Técnicas (CONICET), Suipacha 531, 2000, Rosario, Argentina

收稿日期:2024-03-25 出版日期:2024-10-24 发布日期:2024-10-14
通讯作者: Mario O. Salazar,E-mail:msalazar@fbioyf.unr.edu.ar
基金资助:
Ricardo L. E. Furlan and Mario O. Salazar would like to acknowledge for provided financial support by Universidad Nacional de Rosario (80020180300114UR and 80020180100128UR), CONICET (PIP No 11220200102423) and FONCYT (PICT2015-3574 and PICT2018-01554) for the development of this work.

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

Liz E. Lescano¹, Mario O. Salazar^1,2, Ricardo L. E. Furlan^1,2

1. Farmacognosia, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario (UNR), Suipacha 531, 2000, Rosario, Argentina;
2. Consejo Nacional de Investigaciones Científicas y Técnicas (CONICET), Suipacha 531, 2000, Rosario, Argentina

Received:2024-03-25 Online:2024-10-24 Published:2024-10-14
Contact: Mario O. Salazar,E-mail:msalazar@fbioyf.unr.edu.ar
Supported by:
Ricardo L. E. Furlan and Mario O. Salazar would like to acknowledge for provided financial support by Universidad Nacional de Rosario (80020180300114UR and 80020180100128UR), CONICET (PIP No 11220200102423) and FONCYT (PICT2015-3574 and PICT2018-01554) for the development of this work.

摘要/Abstract

摘要： 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.

关键词: Chemically modified essential oils, Ammonium thiocyanate, Iodine catalysis, Bioactive compounds, Acetylcholinesterase inhibitors

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.

Key words: Chemically modified essential oils, Ammonium thiocyanate, Iodine catalysis, Bioactive compounds, Acetylcholinesterase inhibitors

Liz E. Lescano, Mario O. Salazar, Ricardo L. E. Furlan. Chemically engineered essential oils prepared through thiocyanation under solvent-free conditions: chemical and bioactivity alteration[J]. 应用天然产物, 2024, 14(5): 35-35.

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

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

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