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

Abstract

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New azodyrecins identified by a genome mining-directed reactivity-based screening

“…The combination of 1 H and 13 C NMR with a series of 2D NMR analyses and optical rotation revealed that six of the isolated compounds are azodyrecin A ( 1 ), azodyrecin B ( 2 ), azodyrecin C ( 3 ), and their geometric isomers 1’- trans -azodyrecin A ( 4 ), 1’- trans -azodyrecin B ( 5 ), and 1’- trans -azodyrecin C ( 6 ), respectively, which were previously discovered from Streptomyces sp. strain P8-A2 ( Figure 3a ) [ 21 ]. Of note, the trans -azodyrecins 4 – 6 are reportedly generated by the spontaneous isomerization of the cis -congeners, after long-term exposure to CHCl 3 [ 21 ].…”

“…strain P8-A2 ( Figure 3a ) [ 21 ]. Of note, the trans -azodyrecins 4 – 6 are reportedly generated by the spontaneous isomerization of the cis -congeners, after long-term exposure to CHCl 3 [ 21 ]. While trans -azodyrecins could also be generated nonenzymatically from their cis -congeners during the isolation process, trans -azodyrecins were detected in the fresh extracts of the solid cultures from both strains, suggesting that they are also generated in vivo (Figure S2 in Supporting Information File 1 ).…”

Chemistry and Biology of Natural Azoxy Compounds

“…Very recently, three natural azoxyalkenes, azodyrecins A–C ( 26 – 28 ), belonging to a novel class of aozxy compounds, were isolated from a soil Streptomyces sp . Compounds 26 – 28 contain a cis -alkenyl moiety, similar to elaiomycin ( 1 ).…”

“…Because most microbial-derived azoxyalkenes contain a trans -alkenyl moiety, this observation provides an additional structural understanding of the natural azoxyalkenes and raises the possibility that the reported trans -alkenyl azoxy compounds could be artifacts derived from isomerization. The azodyrecins were cytotoxic toward brine shrimp and HL-60 cells …”

“…However, the azodyrecins probably derive from alanine instead of serine. Additionally, there is no further chain elongation by a polyketide synthase in the azodyrecins …”