Argolide from Artemisia glabella Kar. et Kir. and syntheses of new biologically active compounds

IF 2.5 3区医学 Q3 CHEMISTRY, MEDICINAL

Fitoterapia Pub Date : 2025-05-02 DOI:10.1016/j.fitote.2025.106583

S.M. Adekenov

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引用次数: 0

Abstract

The article is dedicated to the chemical transformations of the natural sesquiterpene γ-lactone molecule 3-oxo-4,7α,6β(H)-germacr-1(10)(E),11(13)-dien-6,12-olide (argolide). For the first time, 18 new derivatives based on 3-oxo-4,7α,6β(H)-germacr-1(10)(E),11(13)-dien-6,12-olide have been synthesized, representing polyfunctional molecules with oxygen functionalities, halogen atoms, phosphorus, and nitrogen. The reaction of forming a hybrid compound based on sesquiterpene γ-lactone and alkaloids is discussed. Stereoselectivity and regioselectivity of the reaction of the molecule 3-oxo-4,7α,6β(H)-germacr-1(10)(E),11(13)-dien-6,12-olide with reagents are noted.

The new germacranolide compounds were studied for cytotoxicity, antitumor, antiparasitic, and antimicrobial activities.

In in vitro experiments, antiparasitic activity of argolide samples and their derivatives against the promastigote of Leishmania amazonensis and the trypomastigote of Trypanosoma brucei brucei was observed. In in vivo conditions, 100 % effectiveness of argolide against helminths Toxocara canis, Ancylostoma caninum, and Uncinaria stenocephala was determined in dogs.

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青蒿素属植物。吉珥。以及新的生物活性化合物的合成

本文致力于天然倍半萜γ-内酯分子3-oxo-4,7α,6β(H)-germacr-1(10)(E),11(13)-dien-6,12-olide （argolide）的化学转化。首次合成了18个以3-氧-4,7α,6β(H)-germacr-1(10)(E),11(13)-二烯-6,12-olide为基础的新衍生物，代表了具有氧官能团、卤素原子、磷和氮的多官能团分子。讨论了倍半萜γ-内酯与生物碱合成杂化化合物的反应。观察了分子3-氧-4,7α,6β(H)-germacr-1(10)(E),11(13)-二烯-6,12-olide与试剂反应的立体选择性和区域选择性。研究了新化合物的细胞毒性、抗肿瘤活性、抗寄生虫活性和抗菌活性。在体外实验中，观察了银果内酯样品及其衍生物对亚马逊利什曼原虫原马鞭毛虫和布鲁氏锥虫锥马鞭毛虫的抗寄生活性。在体内条件下，测定了银壳内酯对犬弓形虫、犬钩虫和窄头棘虫的100%有效性。

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来源期刊

Fitoterapia 医学-药学

CiteScore

5.80

自引率

2.90%

发文量

198

审稿时长

1.5 months

期刊介绍： Fitoterapia is a Journal dedicated to medicinal plants and to bioactive natural products of plant origin. It publishes original contributions in seven major areas: 1. Characterization of active ingredients of medicinal plants 2. Development of standardization method for bioactive plant extracts and natural products 3. Identification of bioactivity in plant extracts 4. Identification of targets and mechanism of activity of plant extracts 5. Production and genomic characterization of medicinal plants biomass 6. Chemistry and biochemistry of bioactive natural products of plant origin 7. Critical reviews of the historical, clinical and legal status of medicinal plants, and accounts on topical issues.