DMOA-derived polycyclic meroterpenoids with antiviral activities from the deep-sea-derived fungus Penicillium pancosmium A6A

IF 2.5 3区医学 Q3 CHEMISTRY, MEDICINAL Fitoterapia Pub Date : 2024-10-10 DOI:10.1016/j.fitote.2024.106248

Ziming Chen , Yinghui Lv , Zhuhua Luo , Bihong Hong , Siwen Niu

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Abstract

Two undescribed 3,5-dimethylorsellinic acid (DMOA) derived meroterpenoids, namely pancosterpenoids A (1) and B (2), were discovered from the EtOAc extract of the deep-sea sediment-derived fungus Penicillium pancosmium A6A. The gross structures were established by detailed analysis of the spectroscopic data (NMR and HRESIMS spectra), while their absolute configurations were resolved by comparing the experimental and calculated ECD data as well as X-ray single crystal diffraction analysis. Pancosterpenoid A (1) was the first representative of DMOA-derived meroterpenoids possessing a 6/6/6/5/5 pentacyclic system, while pancosterpenoid B (2) belongs to a class of rare 13-nor-citreohybridone meroterpenoids. Two metabolites were evaluated the antiviral effects against severe acute respiratory syndrome coronavirus-2 (SARS-CoV-2) trVLP pseudovirus. As a result, compounds 1 and 2 showed moderately inhibitory activities with IC₅₀ values of 22.37 and 18.12 μM, respectively.

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来自深海源真菌青霉 A6A 的具有抗病毒活性的 DMOA 衍生多环美拉皮素。

从源于深海沉积物的真菌青霉 A6A 的乙酸乙酯提取物中发现了两种未曾描述过的 3,5-二甲基月桂酸（DMOA）衍生美拉皮素，即泛醇类 A (1) 和 B (2)。通过对光谱数据（核磁共振和 HRESIMS 光谱）的详细分析，确定了它们的总体结构，同时通过比较实验和计算的 ECD 数据以及 X 射线单晶衍射分析，确定了它们的绝对构型。Pancosterpenoid A（1）是第一个具有 6/6/6/5/5 五环体系的 DMOA 衍生经并萜类化合物的代表，而 Pancosterpenoid B（2）则属于罕见的 13-nor-citreohbridyone 经并萜类化合物。研究人员评估了这两种代谢物对严重急性呼吸系统综合征冠状病毒-2（SARS-CoV-2）trVLP 伪病毒的抗病毒作用。结果表明，化合物 1 和 2 显示出中等程度的抑制活性，IC50 值分别为 22.37 和 18.12 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.