Structural determination of a new naturally occurring cyclic vitamin K

The respiratory quinone composition of 5 members of the genus Nocardia was examined. All species contained a hitherto unknown cyclic vitamin K-like molecule as their predominant lipoquinone. On the basis of mass spectrometry, 1H and 13C nuclear magnetic resonance spectrometry, the novel quinone was shown to correspond to (2 E,14 E,18 E,22 E)-2-[3,7,11,15,19, 23-hexamethyl-25-(2,6,6-trimethylcyclohex-2-enyl)pentacosa-2,14,18,22-tetraenyl]-3-methyl-1,4-naphthoquinone. Results indicate this molecule may respresent a valuable phylogenetic marker for the prokaryote genus Nocardia.