Isolation and characterization of a novel coenzyme Q from some methane-oxidizing bacteria.

The respiratory quinone composition of 18 strains of obligate methane-utilizing bacteria was examined. All of the strains contained lipoquinones which on examination by tlc co-chromatographed with coenzyme Q. On the basis of chromatographic and physicochemical analyses the lipoquinones produced by 10 of the strains corresponded to Q-8. Reverse-phase partition and argentation hplc demonstrated the quinone produced by the remaining 8 strains did not correspond to any known coenzyme Q prenologue. On the basis of mass spectrometry, 1H and 13C nuclear magnetic resonance spectrometry the novel quinone was shown to correspond to 2,3-dimethoxy-5-methyl-6-(18-methylene-3,7, 11,15,19,23,27,31-octamethyldotriacontahepta-2,6,10,14,22,26,30 enyl-)-1, 4-benzoquinone.