Penrhizovarin A, a novel indole diterpene from endophytic fungi Penicillium sp. KYG-9

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron Pub Date : 2025-09-01 DOI:10.1016/j.tet.2025.134914

Dong Gan , Jin-Hua Yu , Da-Mei Wang , Jie-Zhen Shi , Le Cai , Zhong-Tao Ding

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Abstract

One novel indole diterpene penrhizovarin A (1) and one known analogue (2), were characterized from Penicillium sp. KYG-9. Structural elucidation was accomplished through comprehensive spectroscopic analyses, including high-resolution electrospray ionization mass spectrometry (HR-ESI-MS), X-ray crystallography, and electronic circular dichroism (ECD) calculations. Penrhizovarin A (1) is the first reported indole diterpene characterized by both an unprecedented F-ring cleavage and a novel 4/6/6/6/5–6/6/6 pentacyclic scaffold incorporating a rare dioxabicyclo[3.3.1]nonane unit. The single crystal of 2 was obtained for the first time, and its planar structure and stereochemistry were further confirmed by X-ray single crystal diffraction. In vitro bioassays revealed that penrhizovarin A exhibited potent cytotoxicity against all tested human cancer cell lines, with particularly notable activity against HL-60 (leukemia), A-549 (lung cancer), and SW-480 (colon cancer) cell lines, surpassing the activity of the positive control cisplatin. Additionally, penrhizovarin A demonstrated significant antifungal activities.

Abstract Image

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内生真菌青霉菌（Penicillium sp. KYG-9）中的一种新型吲哚二萜

从青霉菌KYG-9中鉴定了一种新的吲哚二萜根瘤素A(1)和一种已知的类似物(2)。通过全面的光谱分析，包括高分辨率电喷雾电离质谱（HR-ESI-MS）、x射线晶体学和电子圆二色性（ECD）计算，完成了结构解析。Penrhizovarin A(1)是第一个报道的吲哚二萜，其特点是具有前所未有的f环裂解和新型的4/6/6/6/ 6 - 6/6/6五环支架，其中包含罕见的二恶双环[3.3.1]壬烷单元。首次获得了2的单晶，并通过x射线单晶衍射进一步证实了其平面结构和立体化学性质。体外生物测定显示，penrhizovarin A对所有被测试的人类癌细胞系都表现出强大的细胞毒性，对HL-60（白血病）、A-549（肺癌）和ws -480（结肠癌）细胞系的活性尤其显著，超过了阳性对照顺铂的活性。此外，penrhizovarin A具有显著的抗真菌活性。

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来源期刊

Tetrahedron 化学-有机化学

CiteScore

3.90

自引率

4.80%

发文量

439

审稿时长

34 days

期刊介绍： Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry. Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters. Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.