Lasiodiplodiapyrones A and B, Pyrone-Preussomerin Adducts with Highly Strained Polycyclic Ring Systems from Lasiodiplodia pseudotheobromae

J Nat Prod. 2023 Jan 27;86(1):18-23. doi: 10.1021/acs.jnatprod.2c00530.

Yu Liang ¹, Qin Li ¹, Yongqi Li ¹, Yuyi Zheng ¹, Yong Shen ¹, Haojie Yang ², Yuling Lu ¹, Junjun Liu ¹, Qun Zhou ¹, Dongyan Li ³, Weiguang Sun ¹, Hucheng Zhu ¹, Chunmei Chen ¹, Yonghui Zhang ¹

Affiliations

1 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.
2 Huaxi MR Research Center, Department of Nuclear Medicine, Frontiers Science Center for Diseaserelated Molecular Network, National Clinical Research Center for Geriatrics, West China Hospital, Sichuan University, Chengdu 610000, Sichuan Province, People's Republic of China.
3 Tongji Hospital, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, Hubei Province, People's Republic of China.

PMID: 36607819 DOI: 10.1021/acs.jnatprod.2c00530

Abstract

Lasiodiplodiapyrones A and B (1 and 2), two new preussomerin derivatives, possessing an unexpected 6-methyl-4H-furo[3,2-c]pyran-4-one moiety and a highly functionalized conjoint and complicated polycyclic ring system, along with two known congeners (3 and 4), were isolated from the fungus Lasiodiplodia pseudotheobromae. Their structures including absolute configurations were determined by spectroscopic analyses, Mosher's method, and ECD calculations. A biosynthetic pathway was proposed to explain the origin of lasiodiplodiapyrones A and B as well as their relationship with preussomerins. Compounds 1-4 showed suppressive effects on the production of NO with IC₅₀ values of 4.8 ± 0.3, 8.5 ± 1.1, 5.9 ± 0.8, and 12.8 ± 1.3 μM, respectively.

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