Issue 22, 2019

Clavipines A–C, antiproliferative meroterpenoids with a fused azepine skeleton from the basidiomycete Clitocybe clavipes

Abstract

Three novel meroterpenoids, clavipines A–C (1–3), possessing a benzoquinone fused to an azepine ring and a ten-membered carbocycle with α,β-epoxy/unsaturated-γ-lactone, along with a new natural compound clavilactone F (4) and two known clavilactones D (5) and A (6) were isolated from the basidiomycete Clitocybe clavipes. Their structures with absolute configurations were unambiguously established by extensive spectroscopic analyses, and ECD and X-ray methods. An unusual seven-azepine skeleton was postulated to be formed biosynthetically via a rearrangement of quinone–amino acid conjugates. The biosynthetic origin of meroterpenoids with a benzo-fused 10-membered carbocycle unit was determined by incorporation of 13C-labeled precursors. Compound 1 exhibited significant antiproliferative activity against HepG2 and A549 cells with IC50 values of 4.28 ± 0.26 and 7.49 ± 0.41 μM, respectively.

Graphical abstract: Clavipines A–C, antiproliferative meroterpenoids with a fused azepine skeleton from the basidiomycete Clitocybe clavipes

Supplementary files

Article information

Article type
Research Article
Submitted
12 Aug 2019
Accepted
27 Sep 2019
First published
30 Sep 2019

Org. Chem. Front., 2019,6, 3759-3765

Clavipines A–C, antiproliferative meroterpenoids with a fused azepine skeleton from the basidiomycete Clitocybe clavipes

Z. Sun, N. Zhu, M. Zhou, X. Huo, H. Wu, Y. Tian, J. Yang, G. Ma, Y. Yang and X. Xu, Org. Chem. Front., 2019, 6, 3759 DOI: 10.1039/C9QO01005J

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