TY - JOUR
T1 - Azodyrecins A-C: Azoxides from a Soil-Derived Streptomyces Species
AU - Wibowo, Mario
AU - Gotfredsen, Charlotte H.
AU - Sassetti, Elisa
AU - Melchiorsen, Jette
AU - Clausen, Mads Hartvig
AU - Gram, Lone
AU - Ding, Ling
PY - 2020
Y1 - 2020
N2 - 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.
AB - 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.
U2 - 10.1021/acs.jnatprod.0c00339
DO - 10.1021/acs.jnatprod.0c00339
M3 - Journal article
C2 - 33216557
SN - 0163-3864
VL - 83
SP - 3519
EP - 3525
JO - Journal of Natural Products
JF - Journal of Natural Products
IS - 12
ER -