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距骨麦角甾醇A - C:来自一种衍生真菌的三种具有抗真菌活性的不寻常甾体 - 聚酮共轭物

Talarergosteroids A-C: Three Unusual Steroid-Polyketone Conjugates with Antifungal Activity from a Derived Fungus sp.

作者信息

Li Jialin, Lin Zirong, Zeng Haiqi, Zeng Jiechang, Ye Siyao, Chen Chen, Jia Hao, Li Kang, She Zhigang, Long Yuhua

机构信息

School of Chemistry, Guangzhou Key Laboratory of Analytical Chemistry for Biomedicine, South China Normal University, Guangzhou 510006, China.

出版信息

J Agric Food Chem. 2025 Jan 8;73(1):595-605. doi: 10.1021/acs.jafc.4c10156. Epub 2024 Dec 19.

DOI:10.1021/acs.jafc.4c10156
PMID:39701975
Abstract

Three previously undescribed steroid-polyketone conjugates, talarergosteroids A-C (-), together with talarergosteroid D (), which was first identified from a natural source, were isolated from a derived fungus sp. SCNU-F0041. Compounds and bear a complicated 6/6/6/5/6/6 hexacyclic ring system characterized by an oxaspiro[5.5]undecane architecture. Compound possesses a benzofuran moiety substituted at C-3 in ergosterol. The structures of the new compounds were identified by comprehensive spectroscopic analysis, X-ray diffraction, and electronic circular dichroism (ECD) calculation. Talarergosteroid B () showed significant inhibitory activity against the agricultural plant pathogen f. sp. (MIC = 0.78 μg/mL), outperforming the positive control carbendazim (MIC = 1.56 μg/mL). Preliminary research disclosed that compound may inhibit the spore germination progress, malform the fungal mycelium, and damage the organelle. These results indicate that compound could be a potential fungicidal lead compound against f. sp. .

摘要

从一株衍生真菌SCNU-F0041中分离出三种之前未被描述的甾体-聚酮共轭物,即塔拉麦角甾醇A-C(-),以及首次从天然来源鉴定出的塔拉麦角甾醇D()。化合物和具有一个复杂的6/6/6/5/6/6六元环系统,其特征为一个氧杂螺[5.5]十一烷结构。化合物在麦角甾醇的C-3位带有一个苯并呋喃部分。通过综合光谱分析、X射线衍射和电子圆二色性(ECD)计算确定了新化合物的结构。塔拉麦角甾醇B()对农业植物病原菌f. sp. 表现出显著的抑制活性(MIC = 0.78 μg/mL),优于阳性对照多菌灵(MIC = 1.56 μg/mL)。初步研究表明,化合物可能抑制孢子萌发过程,使真菌菌丝体畸形,并破坏细胞器。这些结果表明,化合物可能是一种针对f. sp. 的潜在杀真菌先导化合物。

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