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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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
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cited_by cdi_FETCH-LOGICAL-a348t-da85a6ef63fcc1c0fe33c89cf03ae7a1f7017aef857afe69f716b3835d5c3ee23
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container_end_page 1494
container_issue 6
container_start_page 1486
container_title Journal of natural products (Washington, D.C.)
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creator Li, Changyan
Shao, Yating
Li, Wei
Yin, Tianpeng
Li, Hongtao
Yan, Hui
Guo, Xingyi
Liu, Bo
He, Bo
description 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.
doi_str_mv 10.1021/acs.jnatprod.1c01155
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title Hybrid Diterpenic Meroterpenoids from an Endophytic Penicillium sp. Induced by Chemical Epigenetic Manipulation
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