Summary: Menaquinone- (2-methyl-3-farnesyl-farnesyl-1,4-naphthoquinone) and a methyl-substituted menaquinone- (2,[5 or 8]-dimethyl-3-farnesyl-faniesyl-1,4-naphthoquinone) were the major isoprenoid quinones found in membrane preparations of and subsp. By reverse-phase high-performance liquid chromatography (HPLC) and thin-layer chromatography (TLC) the faster-eluting menaquinone- co-chromatographed with a menaquinone- standard. The identity of menaquinone- was confirmed by UV spectrophotometry, mass spectrometry and nuclear magnetic resonance (NMR) analysis. The slower-eluting methyl-substituted menaquinone- co-chromatographed with a menaquinone- standard by reverse-phase TLC but eluted between menaquinone- and menaquinone- standards by HPLC. The UV spectrum of the rnethyl-substituted menaquinone- did not correlate with either authentic menaquinone or demethylmenaquinone. Mass spectra showed an increase of 14 mass units when compared to menaquinone- and indicated that a methyl substituent was on the naphthoquinone nucleus. NMR spectra confirmed the presence of a methyl substituent at a peri position (carbon-5 or -8) on the benzenoid ring.


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