Clavipines A–C, antiproliferative meroterpenoids with a fused azepine skeleton from the basidiomycete Clitocybe clavipes
Literature Information
Publication Date
2019-09-30
DOI
10.1039/C9QO01005J
Impact Factor
5.281
Authors
Zhaocui Sun, Nailiang Zhu, Man Zhou, Xiaowei Huo, Haifeng Wu, Yu Tian, Junshan Yang, Guoxu Ma, Yan-Long Yang, Xudong Xu
View Original
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.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
(S)-1-(3-(Benzyloxy)phenyl)-3-(dimethylamino)-2-methylpropan-1-one (2r,3r)-2,3-bis(benzoyloxy)succinate
CAS Number:
1004315-81-4
Molecular Formula:
C37H37NO10
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