Structural Elucidation of Tenebrathin: Cytotoxic C‑5-Substituted γ‑Pyrone with a Nitroaryl Side Chain from Streptoalloteichus tenebrarius

Tenebrathin (1), a new C-5-substituted γ-pyrone with a nitroaryl side chain, was isolated from the rare actinomycete Streptoalloteichus tenebrarius NBRC 16177. The chemical structure of 1 was elucidated by a spectroscopic analysis using the crystalline sponge method of crystallization-free X-ray cry...

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Bibliographic Details
Published in:Organic letters 2019-08, Vol.21 (16), p.6519-6522
Main Authors: Hoshino, Shotaro, Mitsuhashi, Takaaki, Kikuchi, Takashi, Wong, Chin Piow, Morita, Hiroyuki, Awakawa, Takayoshi, Fujita, Makoto, Abe, Ikuro
Format: Article
Language:English
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Summary:Tenebrathin (1), a new C-5-substituted γ-pyrone with a nitroaryl side chain, was isolated from the rare actinomycete Streptoalloteichus tenebrarius NBRC 16177. The chemical structure of 1 was elucidated by a spectroscopic analysis using the crystalline sponge method of crystallization-free X-ray crystallography. The biosynthetic origin of the unusual C-5-substituted γ-pyrone in 1 was revealed by a 13C-labeling experiment. Compound 1 exhibited moderate cytotoxicity against several cancer cell lines and likely targets some protein kinases.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b02443