呋沙瑞斯特 A-E，一种新的γ-吡喃酮类聚酮化合物，来源于真菌尖镰孢菌 Hungcl 及呋沙瑞斯特 D 的结构修正。

Fusaresters A-E, new γ-pyrone-containing polyketides from fungus Fusarium sp. Hungcl and structure revision of fusariumin D.

机构信息

Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, Hubei Province, People's Republic of China.

出版信息

Org Biomol Chem. 2019 Jun 5;17(22):5526-5532. doi: 10.1039/c9ob00534j.

DOI:10.1039/c9ob00534j

PMID:31041978

Abstract

Marine-derived fungi have been regarded as an under-explored and promising reservoir of structurally novel and bioactive natural products. In this study, five new γ-pyrone-containing polyketides, fusaresters A-E (1-5), were isolated and identified from the culture extracts of a marine-derived fungus Fusarium sp. Hungcl. The structures of compounds 1-5 were elucidated on the basis of their HRESIMS and NMR spectroscopic data as well as 13C NMR calculation and electronic circular dichroism (ECD) analyses. Remarkably, the structure of fusariumin D was revised to (9S*,11S*)-3. All these isolates were tested for the cytotoxicity against seven human cancer cell lines, including SW480, HL-60, A549, MCF-7, HepG2, HeLa and SMMC-7721, and the inhibitory activity against protein tyrosine phosphatase 1B (PTP1B). The results revealed that only compound 2 showed a weak inhibition rate of 56% at 40 μM.

摘要

海洋来源的真菌被认为是一个尚未充分开发但具有广阔前景的结构新颖和具有生物活性的天然产物资源库。在本研究中，从海洋来源真菌 Fusarium sp. Hungcl 的培养提取物中分离并鉴定出了五个新的含γ-吡喃酮的聚酮化合物，分别命名为 fusaresters A-E（1-5）。根据它们的高分辨质谱（HRESIMS）和核磁共振波谱（NMR）数据以及 13C NMR 计算和电子圆二色性（ECD）分析，确定了化合物 1-5 的结构。值得注意的是，fusariumin D 的结构被修订为（9S*,11S*）-3。所有这些分离物都进行了对七种人癌细胞系（包括 SW480、HL-60、A549、MCF-7、HepG2、HeLa 和 SMMC-7721）的细胞毒性测试以及对蛋白酪氨酸磷酸酶 1B（PTP1B）的抑制活性测试。结果表明，只有化合物 2 在 40 μM 时表现出 56%的弱抑制率。