Issue 18, 2023

Terpenoids from Penicillium chrysogenum MT-40, an endophytic fungus isolated from Huperzia serrata

Abstract

Two novel 3,5-dimethylorsellinic acid derived meroterpenoids, peniciterpenolides A (1) and B (2) individually containing a 2-oxaspiro[4,5]deca-6,8-diene-1,4-dione and a 6-oxabicyclic[3,2,1]oct-3-en-7-one motif, one new spongian-type diterpene, peniciterpenolide C (3), and one new drimane-type sesquiterpene, peniciterpenolide D (4), together with the known meroterpenoid atlantinone B (5) were isolated from Penicillium chrysogenum MT-40, an endophytic fungus identified from Huperzia serrata. All the five compounds additionally contain a unique 2-oxabicyclo[2.2.2]octan-3-one moiety formed by the annulation of the C-3 hydroxyl and the oxidized methyl on C-10. The structures were established by the analysis of their spectroscopic data, single-crystal X-ray diffraction, and quantum chemical calculations of electronic circular dichroism spectra. Compounds 1–5 showed inhibition of nitric oxide production in lipopolysaccharide-activated RAW 264.7 macrophage cells with IC50 values in the range of 20.6–46.9 μM.

Graphical abstract: Terpenoids from Penicillium chrysogenum MT-40, an endophytic fungus isolated from Huperzia serrata

Supplementary files

Article information

Article type
Research Article
Submitted
07 Jun 2023
Accepted
03 Aug 2023
First published
04 Aug 2023

Org. Chem. Front., 2023,10, 4598-4605

Terpenoids from Penicillium chrysogenum MT-40, an endophytic fungus isolated from Huperzia serrata

F. Jia, M. Zhang, J. Fan, Y. Wang, X. Ge, X. Mi, X. Liu, J. Wang, P. Tu and S. Shi, Org. Chem. Front., 2023, 10, 4598 DOI: 10.1039/D3QO00856H

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