Evaluation of cytotoxic effects of capillene and 2,4-pentadiynylbenzene isolated from Artemisia campestris subsp. variabilis (Ten.) Greuter essential oil and identified by NMR studies

IF 2.5 3区医学 Q3 CHEMISTRY, MEDICINAL

Fitoterapia Pub Date : 2025-05-05 DOI:10.1016/j.fitote.2025.106598

Natale Badalamenti , Francesco Sgadari , Rosario Schicchi , Alessandro Crisafulli , Alessandro Vaglica , Maurizio Bruno , Filippo Maggi , Luana Quassinti , Massimo Bramucci

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引用次数: 0

Abstract

Artemisia is a vast genus of the Asteraceae family, comprising around five-hundred species, that has a large distribution in Europe, America, Asia, and Australia. Species of this genus have been reported to have several ethnopharmacological activities, and some of them are also largely used as food and spices. Artemisia campestris subsp. variabilis (Ten.) Greuter is a quite rare species endemic to Sicily, Sardinia, and Southern Italy. Seeking to delve deeper into the phytochemistry and pharmacological aspects of this species, in this work we investigated the essential oil (EO) obtained from the aerial parts of Sicilian accessions, hitherto unexplored, growing wild near Messina, Italy. The chemical composition of the EO, obtained by hydro-distillation method, was evaluated by GC and GC–MS. The most abundant constituent was capillene (36.45 %), principal representative of the alkynes class (50.69 %). However similar amount of hydrocarbon monoterpenes was identified (49.18 %), with β-pinene present at 35.31 %. The two alkyne compounds were confirmed by isolation and ¹H NMR and ¹³C NMR spectroscopic characterization. The EO and its main constituents have been tested for possible cytotoxic activity against three human tumor cell lines (A375, MDA-MB 231, and CaCo2) and a human non-tumor cell line (HEK293) using the MTT assay. The EO showed remarkable cytotoxic activity against all cell lines tested with IC₅₀ values ranging between 7.55 μg/mL and 23.05 μg/mL. 2,4-Pentadiynylbenzene exhibited potent cytotoxic activity with IC₅₀ values ranging between 0.25 and 0.45 μg/mL for HEK293 and CaCo2 cells, respectively, while capillene showed very similar IC₅₀ values ranging between 0.14 and 0.52 μg/mL for A375 and CaCo2 cells, respectively. The results demonstrated a remarkable cytotoxic activity against human tumor cell lines and suggest that A. campestris subsp. variabilis EO and could be regarded as a natural bioactive source and, in the future, further analyses could clarify the mechanism of action of the EO and its main constituents.

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青蒿中毛细烯和2,4-戊二苯的细胞毒作用评价。摘要(10)。通过核磁共振研究鉴定了格鲁特精油

青蒿属是菊科的一个大属，大约有500种，分布在欧洲、美洲、亚洲和澳大利亚。据报道，本属植物具有多种民族药理学活性，其中一些也被广泛用作食品和香料。野蒿亚属。摘要(10)。格鲁特是西西里岛、撒丁岛和意大利南部特有的一种非常罕见的物种。为了更深入地研究这一物种的植物化学和药理方面，在这项工作中，我们研究了从西西里植物的空中部分获得的精油（EO），迄今为止尚未开发，生长在意大利墨西拿附近的野生植物。用气相色谱和气相色谱-质谱分析了氢蒸馏法得到的环氧乙烷的化学成分。其中以毛细烯含量最高（36.45%），为炔类的主要代表（50.69%）。而单萜化合物含量相近（49.18%），其中β-蒎烯含量为35.31%。两个炔类化合物经分离、1H NMR和13C NMR表征证实。用MTT法测试了EO及其主要成分对三种人类肿瘤细胞系（A375、MDA-MB 231和CaCo2）和一种人类非肿瘤细胞系（HEK293）可能的细胞毒活性。EO对所有细胞系均表现出显著的细胞毒活性，IC50值在7.55 ~ 23.05 μg/mL之间。2,4-戊二苯对HEK293和CaCo2细胞的IC50值分别为0.25 ~ 0.45 μg/mL，毛细烯对A375和CaCo2细胞的IC50值分别为0.14 ~ 0.52 μg/mL。结果表明，油菜芽孢杆菌对人肿瘤细胞系具有明显的细胞毒活性。在今后的研究中，对其作用机理及其主要成分的进一步分析将有助于进一步阐明其作用机理。

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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.