Two sesquiterpenoids and a steroid produced by an endophytic fungus Aspergillus sp. YUD20004 and their bioactivity

IF 2.5 3区医学 Q3 CHEMISTRY, MEDICINAL

Fitoterapia Pub Date : 2025-05-12 DOI:10.1016/j.fitote.2025.106619

Dan-Dan Xia , Jing-Xin Chen , Fei Xie , Yan Geng , Hai-Xia Dong , Hao Zhou , Zhong-Tao Ding

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Abstract

Two new sesquiterpenoids asperpenoids A-B (1–2) and one new ergostane-type steroid aspergteroid (3) were isolated from the fungus Aspergillus sp. YUD20004 which was derived from the tuber of Zingiber officinale Roscoe. Their structures and absolute configurations were elucidated by comprehensive spectroscopic analyses, electronic circular dichroism (ECD) spectra and consideration of the biogenetic origins. Especially, asperpenoid A was featured as a rare spiro[6-oxabicyclo[3.2.1]octane-2,2′-oxirane] 5/6/3 tricyclic skeleton. In vitro cytotoxic activity assays, aspergteroid (3) exhibited significant cytotoxic activities against five human cancer cell lines (SMMC-7721, HL-60, A549, SW480 and MDA-MB-231) with IC₅₀ values ranging from 0.40 to 34.24 μM. Most significantly, compound 3 reduced the viability of SMMC-7721 cells in a concentration-dependent manner with an IC₅₀ value of 0.40 μM.

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内生真菌Aspergillus sp. YUD20004产生的两种倍半萜类和一种类固醇及其生物活性。

从产自生姜块茎的真菌Aspergillus sp. YUD20004中分离得到两个新的倍半萜类asperpenoids A-B（1-2）和一个新的麦角甾类aspergateroid(3)。通过综合光谱分析、电子圆二色（ECD）光谱和生物成因分析，对它们的结构和绝对构型进行了分析。其中asperpenoid A为罕见的螺旋[6-恶沙环[3.2.1]辛烷-2,2′-恶沙环]5/6/3三环骨架。体外细胞毒活性测定表明，aspergteroid(3)对5种人类癌细胞（SMMC-7721、HL-60、A549、SW480和MDA-MB-231）具有显著的细胞毒活性，IC50值在0.40 ~ 34.24 μM之间。最显著的是，化合物3以浓度依赖的方式降低SMMC-7721细胞的活力，IC50值为0.40 μM。

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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.