Hybrid Diterpenic Meroterpenoids from an Endophytic Penicillium sp. Induced by Chemical Epigenetic Manipulation

Cultivation of an endophytic fungus Penicillium sp. KMU18029 with suberanilohydroxamic acid (SAHA), a histone deacetylase inhibitor, led to the isolation of two pairs of diterpenic meroterpenoids with a unique natural product framework combining features of pyripyropenes and decaturins/oxalicines, p...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2022-06, Vol.85 (6), p.1486-1494
Main Authors: Li, Changyan, Shao, Yating, Li, Wei, Yin, Tianpeng, Li, Hongtao, Yan, Hui, Guo, Xingyi, Liu, Bo, He, Bo
Format: Article
Language:English
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Summary:Cultivation of an endophytic fungus Penicillium sp. KMU18029 with suberanilohydroxamic acid (SAHA), a histone deacetylase inhibitor, led to the isolation of two pairs of diterpenic meroterpenoids with a unique natural product framework combining features of pyripyropenes and decaturins/oxalicines, pyrandecarurins A (1) and B (2), pileotin A (3) and B (4), along with their potential precursor decaturenoid (5). Compounds 1, 2, 4, and 5 were new. The structures of 1–5 were elucidated by extensive spectroscopic analyses. The absolute configurations of 1–4 were determined by single-crystal X-ray diffraction, NOESY spectra, ECD calculations, and biogenetic considerations. The absolute configuration of compound 3 was confirmed for the first time. Compound 5 showed moderate activity against AChE with an IC50 value of 13.9 ± 1.1 μM.
ISSN:0163-3864
1520-6025
DOI:10.1021/acs.jnatprod.1c01155