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

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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

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Publication details

The article was received on 12 Aug 2019, accepted on 27 Sep 2019 and first published on 30 Sep 2019


Article type: Research Article
DOI: 10.1039/C9QO01005J
Org. Chem. Front., 2019, Advance Article

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    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, Advance Article , DOI: 10.1039/C9QO01005J

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