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

Shotaro Hoshino; Takaaki Mitsuhashi; Takashi Kikuchi; Chin Piow Wong; Hiroyuki Morita; Takayoshi Awakawa; Makoto Fujita; Ikuro Abe

doi:10.1021/acs.orglett.9b02443

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

Shotaro Hoshino, Takaaki Mitsuhashi, Takashi Kikuchi, Chin Piow Wong, Hiroyuki Morita, Takayoshi Awakawa, Makoto Fujita, Ikuro Abe^*

^*Corresponding author for this work

Section of Natural Products & Drug Discovery, Division of Medicinal Resources, Institute of Natural Medicine

Research output: Contribution to journal › Article › peer-review

10 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	6519-6522
Number of pages	4
Journal	Organic Letters
Volume	21
Issue number	16
DOIs	https://doi.org/10.1021/acs.orglett.9b02443
State	Published - 2019/08/16

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.9b02443

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

abstract = "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.",

author = "Shotaro Hoshino and Takaaki Mitsuhashi and Takashi Kikuchi and Wong, {Chin Piow} and Hiroyuki Morita and Takayoshi Awakawa and Makoto Fujita and Ikuro Abe",

note = "Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

year = "2019",

month = aug,

day = "16",

doi = "10.1021/acs.orglett.9b02443",

language = "英語",

volume = "21",

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T1 - Structural Elucidation of Tenebrathin

T2 - Cytotoxic C-5-Substituted γ-Pyrone with a Nitroaryl Side Chain from Streptoalloteichus tenebrarius

AU - Hoshino, Shotaro

AU - Mitsuhashi, Takaaki

AU - Kikuchi, Takashi

AU - Wong, Chin Piow

AU - Morita, Hiroyuki

AU - Awakawa, Takayoshi

AU - Fujita, Makoto

AU - Abe, Ikuro

PY - 2019/8/16

Y1 - 2019/8/16

N2 - 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.

AB - 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.

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U2 - 10.1021/acs.orglett.9b02443

DO - 10.1021/acs.orglett.9b02443

M3 - 学術論文

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AN - SCOPUS:85070919364

SN - 1523-7060

VL - 21

SP - 6519

EP - 6522

JO - Organic Letters

JF - Organic Letters

IS - 16

ER -

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

Abstract

ASJC Scopus subject areas

UN SDGs

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