Talaromyoxaones A and B: Unusual Oxaphenalenone Spirolactones as Phosphatase Inhibitors from the Marine-Derived Fungus Talaromyces purpureogenus SCSIO 41517,The Journal of Organic Chemistry

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Talaromyoxaones A and B: Unusual Oxaphenalenone Spirolactones as Phosphatase Inhibitors from the Marine-Derived Fungus Talaromyces purpureogenus SCSIO 41517
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2021-09-03 , DOI: 10.1021/acs.joc.1c01452
Xiao Liang ₁ , Zhong-Hui Huang ₁ , Wen-Bin Shen ₂ , Xin-Hua Lu ₂ , Xue-Xia Zhang ₂ , Xuan Ma ₁ , Shu-Hua Qi _{1,

3}

Affiliation

(+)- and (−)-talaromyoxaones A and B (1 and 2, respectively), two new oxaphenalenone derivatives with a hemiacetal frame and an unprecedented spirolactone frame of a 2′H,3H,4′H-spiro[isobenzofuran-1,3′-pyran]-3-one unit that show biosynthetic enantiodivergence, and two new oxaphenalenone analogues (±)-11-apopyrenulin (3) and (+)- or (−)-abeopyrenulin (4) were isolated from the marine-derived fungus Talaromyces purpureogenus SCSIO 41517. Their structures were elucidated by spectroscopic analysis, single-crystal X-ray diffraction, and quantum chemical calculations of ECD spectra. Compounds 1 and 2 showed selective inhibitory activity against phosphatases SHP1, SHP2, and MEG2 with IC₅₀ values of 1.3–3.4 μM, and the potential modes of action for 1 were investigated by a preliminary molecular docking study.

中文翻译：

Talaromyoxaones A 和 B：作为来自海洋来源的真菌 Talaromyces purpureogenus SCSIO 41517 的磷酸酶抑制剂的不寻常 Oxaphenalenone 螺内酯

(+)- 和 (-)-talaromyoxaones A 和 B（分别为1和2），两种具有半缩醛框架的新奥沙芬酮衍生物和前所未有的 2' H ,3 H ,4' H -螺[异苯并呋喃的螺内酯框架-1,3'-吡喃]-3-1 单位显示生物合成对映发散，和两个新的奥沙菲纳酮类似物 (±)-11-apopyrenulin ( 3 ) 和 (+)- 或 (-)-abeopyrenulin ( 4 ) 从海洋来源的真菌Talaromyces purpureogenus SCSIO 41517。通过光谱分析、单晶 X 射线衍射和 ECD 光谱的量子化学计算阐明了它们的结构。化合物1和2显示出对磷酸酶 SHP1、SHP2 和 MEG2 的选择性抑制活性，IC ₅₀值为 1.3-3.4 μM，并且通过初步分子对接研究调查了1的潜在作用模式。

更新日期：2021-09-17

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