Issue 22, 2021

Janthinoid A, an unprecedented tri-nor-meroterpenoid with highly modified bridged 4a,1-(epoxymethano)phenanthrene scaffold, produced by the endophyte of Penicillium janthinellum TE-43

Abstract

Janthinoid A (1), an unprecedented C22 meroterpenoid featuring a highly modified bridged 4a,1-(epoxymethano)phenanthrene scaffold incorporating eight continuous quaternary carbons, along with its biosynthetic-related C25 analogue andrastone I (2), were isolated from the endophytic fungus Penicillium janthinellum TE-43. Their structures were unambiguously established by comprehensive analyses of spectroscopic data, quantum chemical calculations, and X-ray diffraction. The tri-nor-meroterpenoid skeleton of 1 was produced by a unique biosynthetic pathway, involving the ring cleavage and continuous carbon degradations of the aromatic polyketide precursor, which is distinct from the commonly-observed meroterpenoids both structurally and biogenetically, representing a new type of meroterpenoid. Both compounds showed significant in vivo anti-tumor activities against NSCLC cells A549.

Graphical abstract: Janthinoid A, an unprecedented tri-nor-meroterpenoid with highly modified bridged 4a,1-(epoxymethano)phenanthrene scaffold, produced by the endophyte of Penicillium janthinellum TE-43

Supplementary files

Article information

Article type
Research Article
Submitted
20 iyl 2021
Accepted
19 sen 2021
First published
20 sen 2021

Org. Chem. Front., 2021,8, 6196-6202

Janthinoid A, an unprecedented tri-nor-meroterpenoid with highly modified bridged 4a,1-(epoxymethano)phenanthrene scaffold, produced by the endophyte of Penicillium janthinellum TE-43

X. Li, J. Su, B. Jiang, Y. Li, Y. Guo and P. Zhang, Org. Chem. Front., 2021, 8, 6196 DOI: 10.1039/D1QO01066B

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