A novel antimicrobial epoxide isolated from larval Galleria mellonella infected by the nematode symbiont, Photorhabdus luminescens (Enterobacteriaceae).
A novel antimicrobial epoxide, 2-isopropyl-5-(3-phenyl-oxiranyl)-benzene-1,3-diol (1), was identified from larval Galleria mellonella infected by a symbiotically associated bacterium-nematode complex (Photorhabdus luminescens C9-Heterorhabditis megidis 90). Its structure was determined with spectroscopic analysis and confirmed by chemical synthesis starting from a known antibiotic, 2-isopropyl-5-(2-phenylethenyl)-benzene-1,3-diol (2). Epoxide 1 was active against Bacillus subtilis, Escherichia coli, Streptococcus pyogenes, and a drug-resistant, clinical strain of Staphylococcus aureus (RN4220) with minimum inhibitory concentrations in the range of 6.25-12.5 microg/ml. Epoxide 1 was cytotoxic against human cancer cell lines, MCF-7 wt, H460, and Jurkat, with GI(50) of 2.14, 0.63, and 0.42 microM, respectively, but was less toxic on normal, mouse splenic lymphocytes with a GI(50) of 45.00 microM.
Hu
Kaiji
K
Welichem Biotech Inc., Burnaby, BC, Canada. kaijih@yahoo.ca
Li
Jianxiong
J
Li
Bin
B
Webster
John M
JM
Chen
Genhui
G
D000818:Animals; D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D000903:Antibiotics, Antineoplastic / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D045744:Cell Line, Tumor; D004852:Epoxy Compounds / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D006801:Humans; D007814:Larva / Q000737:chemistry / Q000382:microbiology; D007915:Lepidoptera / Q000378:metabolism* / Q000382:microbiology*; D051379:Mice; D050198:Phenoxypropanolamines / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D020637:Photorhabdus; D011437:Propylamines / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*
D000900:Anti-Bacterial Agents; D000903:Antibiotics, Antineoplastic; D004852:Epoxy Compounds; D050198:Phenoxypropanolamines; D011437:Propylamines; C053031:HV 525