Deinococcucins A-D, Aminoglycolipids from Deinococcus sp., a Gut Bacterium of the Carpenter Ant Camponotus japonicus.

Four new aminoglycolipids, deinococcucins A-D (1-4), were discovered from a Deinococcus sp. strain isolated from the gut of queen carpenter ants, Camponotus japonicus. The structures of deinococcucins A-D were elucidated as a combination of N-acetyl glucosamine, 2,3-dihydroxypropanoic acid, and an alkyl amine with a C16 or C17 hydrocarbon chain primarily based on 1D and 2D NMR and mass spectroscopic data. The exact location of the olefinic double bond in deinococcucins C and D (3 and 4) was assigned based on the liquid chromatography-mass spectroscopy data obtained after olefin metathesis. The absolute configurations of the N-acetyl glucosamine and 2,3-dihydroxy moieties were determined through gas chromatography-mass spectroscopy analysis of authentic samples and phenylglycine methyl ester-derivatized products, respectively. Deinococcucins A and C displayed significant induction of quinone reductase in murine Hepa-1c1c7 cells.