Talarolactones A–G, α-Pyrone Dimers with Anti-inflammatory Activities from Talaromyces adpressus, and Their Biosynthetic Pathways

• DOI: 10.1021/acs.orglett.2c04352
• Publication Date: 2023-03-09T13:24:32Z
• Authors: Qin Li; Meijia Zheng; Fengli Li; Yongqi Li; Chunmei Chen; Zijian Huang; Junjun Liu; Weiguang Sun; Ying Ye; Hucheng Zhu; Yonghui Zhang
• Keywords: Talaromyces; Molecular Structure; Pyrones; Anti-Inflammatory Agents; Biosynthetic Pathways

Talarolactones A-G (1-7), seven novel α-pyrone adducts with unprecedented scaffolds, together with two pairs of α-pyrone monomers [(±)-8 and (±)-9)] were isolated from Talaromyces adpressus. Compounds 1-7 are highly modified α-pyrone dimers with a 4,7,7,8-tetrasubstitued 5,6,7,8-tetrahydro-2H-chromen-2-one. Compounds 5 and 6 possessed a significant NO production inhibitory effect, with IC50 values of 2.3 ± 0.1 and 3.7 ± 0.3 μM, respectively. Plausible biosynthetic pathways were proposed and supported by the results of heterologous expression experiments.