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

Organic Letters
Shotaro HoshinoIkuro Abe

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.

References

Nov 1, 1977·The Journal of Antimicrobial Chemotherapy·R Ryden, B J Moore
Mar 1, 1976·The Journal of Antibiotics·J L SchwartzS Omura
Jan 19, 1967·Archiv für Mikrobiologie·G CassinelliA Sanfilippo
Apr 9, 2005·The Journal of Antibiotics·János Bérdy
Nov 24, 2005·Journal of Agricultural and Food Chemistry·Kathrine B ChristensenRichard K Phipps
Sep 1, 2007·Chembiochem : a European Journal of Chemical Biology·Nelly TraitchevaChristian Hertweck
Oct 22, 2009·Natural Product Reports·Markus NettBradley S Moore
Aug 11, 2010·Chemical Communications : Chem Comm·Javier Martí-RujasMasaki Kawano
Nov 26, 2010·Applied and Environmental Microbiology·Hiroyasu OnakaTamotsu Furumai
Mar 29, 2011·Journal of the American Chemical Society·Javier Mart-RujasMasaki Kawano
Mar 30, 2013·Nature·Yasuhide InokumaMakoto Fujita
Sep 24, 2013·Applied Microbiology and Biotechnology·Ramesh Subramani, William Aalbersberg
Sep 30, 2014·Nature Chemical Biology·James R DoroghaziWilliam W Metcalf
Jun 18, 2015·Chemical Communications : Chem Comm·Timothy R RamadharJon Clardy
Mar 24, 2016·IUCrJ·Manabu HoshinoMakoto Fujita
Jun 25, 2016·Beilstein Journal of Organic Chemistry·Till F Schäberle
Nov 15, 2016·Journal of Asian Natural Products Research·Chong-Xi LiuWen-Sheng Xiang
Feb 9, 2018·Angewandte Chemie·Naoki WadaJing-Ke Weng
Jun 19, 1998·Angewandte Chemie·Stuart R Batten, Richard Robson

❮ Previous
Next ❯

Related Concepts

Related Feeds

Antifungals

An antifungal, also known as an antimycotic medication, is a pharmaceutical fungicide or fungistatic used to treat and prevent mycosis such as athlete's foot, ringworm, candidiasis, cryptococcal meningitis, and others. Discover the latest research on antifungals here.

Antifungals (ASM)

An antifungal, also known as an antimycotic medication, is a pharmaceutical fungicide or fungistatic used to treat and prevent mycosis such as athlete's foot, ringworm, candidiasis, cryptococcal meningitis, and others. Discover the latest research on antifungals here.