New sterol and dihydroisocoumarin from the deep-sea derived fungus Cladosporium halotolerans HDN17-72

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC Tetrahedron Letters Pub Date : 2025-03-23 DOI:10.1016/j.tetlet.2025.155555

Yi He , Jiajin Wu , Yuting Liu , Fuhao Liu , Qian Che , Guojian Zhang , Wenxue Wang , Tianjiao Zhu , Dehai Li

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Abstract

Chemical investigations of deep-sea derived fungus Cladosporium halotolerans HDN17-72 yield two new compounds, cladosporisteroid D (1) and cladosporimarin A (2), together with two new natural products (3 and 4), and six known compounds (5–10). Their planar structures were elucidated by detailed analysis of NMR and HRESIMS/MS spectroscopic data. Single-crystal X-ray diffraction analyses resolved the absolute configurations of 1. The absolute configuration of 2 was established by comparison of the specific optical rotation and ECD with that predicted by DFT-based quantum chemical calculation. Compound 2 is the first naturally occurring dihydroisocoumarin derivative linked to the furan ring through the C-4 position. The trihydroxybenzoate derivative 4 exhibited potent antioxidant activity in DPPH radical scavenging test, with an IC₅₀ value of 11.48 μM, better than that of the positive control Vitamin C.

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深海衍生真菌耐盐枝孢菌HDN17-72的新甾醇和二氢异香豆素

对深海衍生真菌Cladosporium halotolerans HDN17-72进行化学研究，得到两个新化合物，cladsporisterooid D(1)和cladsporimarin A(2)，以及两个新天然产物（3和4）和六个已知化合物（5-10）。通过NMR和hresms /MS的详细分析，确定了它们的平面结构。单晶x射线衍射分析确定了1的绝对构型。通过与基于dft的量子化学计算预测的比旋光度和ECD进行比较，建立了2的绝对构型。化合物2是第一个通过C-4位与呋喃环相连的天然存在的二氢异香豆素衍生物。三羟基苯甲酸酯衍生物4在DPPH自由基清除试验中表现出较强的抗氧化活性，IC50值为11.48 μM，优于阳性对照维生素C。

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来源期刊

Tetrahedron Letters 化学-有机化学

CiteScore

3.50

自引率

5.60%

发文量

521

审稿时长

28 days

期刊介绍： Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.