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

Mario Wibowo | Zendy; Charlotte H. Gotfredsen | Zendy; Elisa Sassetti | Zendy; Jette Melchiorsen | Zendy; Mads H. Clausen | Zendy; Lone Gram | Zendy; Ling Ding | Zendy

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

Author(s) -

Mario Wibowo,

Charlotte H. Gotfredsen,

Elisa Sassetti,

Jette Melchiorsen,

Mads H. Clausen,

Lone Gram,

Ling Ding

Publication year - 2020

Publication title -

journal of natural products

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.976

H-Index - 139

eISSN - 1520-6025

pISSN - 0163-3864

DOI - 10.1021/acs.jnatprod.0c00339

Subject(s) - vibrio anguillarum , micrococcus luteus , azoxy , stereochemistry , streptomyces , antimicrobial , chemistry , cytotoxicity , strain (injury) , biology , vibrio , organic chemistry , escherichia coli , bacteria , gene , biochemistry , in vitro , genetics , anatomy

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 rans -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 agains Staphylococcus aureus , Vibrio anguillarum , or Candida albicans , azodyrecin B ( 2 ) exhibited cytotoxicity against the human leukemia cell line HL-60 with an IC 50 value of 2.2 μM.

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