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Structural Elucidation of Tenebrathin: Cytotoxic C-5-Substituted γ-Pyrone with a Nitroaryl Side Chain from Streptoalloteichus tenebrarius .
- Source :
-
Organic letters [Org Lett] 2019 Aug 16; Vol. 21 (16), pp. 6519-6522. Date of Electronic Publication: 2019 Aug 06. - Publication Year :
- 2019
-
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 <superscript>13</superscript> C-labeling experiment. Compound 1 exhibited moderate cytotoxicity against several cancer cell lines and likely targets some protein kinases.
- Subjects :
- Actinobacteria genetics
Anti-Bacterial Agents chemistry
Anti-Bacterial Agents pharmacology
Antineoplastic Agents chemistry
Biosynthetic Pathways genetics
Carbon Isotopes chemistry
Cell Line, Tumor
Crystallography, X-Ray
Humans
Magnetic Resonance Spectroscopy
Microbial Sensitivity Tests
Molecular Structure
Pyrones chemistry
Actinobacteria chemistry
Actinobacteria metabolism
Antineoplastic Agents pharmacology
Subjects
Details
- Language :
- English
- ISSN :
- 1523-7052
- Volume :
- 21
- Issue :
- 16
- Database :
- MEDLINE
- Journal :
- Organic letters
- Publication Type :
- Academic Journal
- Accession number :
- 31386371
- Full Text :
- https://doi.org/10.1021/acs.orglett.9b02443