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

Mario Wibowo, Charlotte H. Gotfredsen, Elisa Sassetti, Jette Melchiorsen, Mads Hartvig Clausen, Lone Gram, Ling Ding*

*Corresponding author for this work

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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.
Original languageEnglish
JournalJournal of Natural Products
Issue number12
Pages (from-to)3519-3525
Number of pages7
Publication statusPublished - 2020


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