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Journal article

Azodyrecins A-C: Azoxides from a Soil-Derived Streptomyces Species

By Wibowo, Mario1,2,3,4; Gotfredsen, Charlotte H.4,5; Sassetti, Elisa5; Melchiorsen, Jette1,2,4,6; Clausen, Mads Hartvig5; Gram, Lone1,2,4,6; Ding, Ling1,2,3,4,7

From

Department of Biotechnology and Biomedicine, Technical University of Denmark1

Section for Microbial and Chemical Ecology, Department of Biotechnology and Biomedicine, Technical University of Denmark2

Natural Product Discovery, Section for Microbial and Chemical Ecology, Department of Biotechnology and Biomedicine, Technical University of Denmark3

Center for Microbial Secondary Metabolites, Centers, Technical University of Denmark4

Department of Chemistry, Technical University of Denmark5

Bacterial Ecophysiology and Biotechnology, Section for Microbial and Chemical Ecology, Department of Biotechnology and Biomedicine, Technical University of Denmark6

DTU Metabolomics Core, Section for Microbial and Chemical Ecology, Department of Biotechnology and Biomedicine, Technical University of Denmark7

Azoxy compounds belong to a small group of natural products sharing a common functional group with the general structure RN = N+(O-)R. Three new azoxides, azodyrecins A-C ( 1-3 ), were isolated from a soil-derived Streptomyces sp. strain P8-A2. The cis-alkenyl unit in 1-3 was found to readily isomerize to the trans-congeners ( 4-6 ).

The structures of the new compounds were determined by detailed spectroscopic (1D/2D NMR) and HRMS data analysis. Azodyrecins belong to a new class of natural azoxy compounds and are proposed to derive from l-alanine and alkylamines. The absolute configurations of 1-6 were defined by comparison of ECD spectra.

While no antimicrobial effects were observed for 1 against Staphylococcus aureus, Vibrio anguillarum, or Candida albicans, azodyrecin B ( 2 ) exhibited cytotoxicity against the human leukemia cell line HL-60 with an IC50 value of 2.2 μM.

Language: English
Publisher: American Chemical Society and American Society of Pharmacognosy
Year: 2020
Pages: 3519-3525
ISSN: 15206025 and 01633864
Types: Journal article
DOI: 10.1021/acs.jnatprod.0c00339
ORCIDs: Wibowo, Mario , Clausen, Mads Hartvig , Gram, Lone , Ding, Ling , Gotfredsen, Charlotte H. and Sassetti, Elisa
Keywords

Azo Compounds Cell Line, Tumor Chromatography, High Pressure Liquid Humans Molecular Structure Oxides Soil Microbiology Spectrum Analysis Streptomyces

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