Chemotaxonomic significance of the xanthomonadins,novel brominated aryl-polyene pigments produced by bacteria of the genus Xanthomonas

The cell pigments produced by strains of Xanthomonas spp. (including representatives of all five presently recognized taxospecies of these phytopathogenic bacteria) have been isolated as isobutyl esters, purified, and characterized in terms of electronic absorption, chromatographic and co-chromatographic, and mass spectrometric properties. This comparative examination reveals that these bacteria produce brominated aryl-polyene pigments which are given the trivial name xanthomonadins. The several xanthomonadins usually occur as mixtures which have been resolved by chromatography and sorted into several Pigment Groups, thus enabling a more rational approach in our on-going systematic study of their exact chemical structures and biosynthesis. From what is presently known, some of the xanthomonadins might differ from xanthomonadin I, the exact structure of which has previously been determined in material from Xanthomonas juglandis ICPB XJ103, by their being monobrominated (rather than dibrominated, as is xanthomonadin I), by their having the equivalent of one methyl group less than does xanthomonadin I, and/or in other ways. The pigments of Xanthomonas ampelina (a little known and possibly questionable member of this genus) seem somewhat different from the pigments of the other Xanthomonas spp. The ability to form these distinctive xanthomonadin pigments is a useful chemotaxonomic marker for the genus Xanthomonas, since such pigments are not known to be formed by taxonomically or ecologically adjacent bacteria. Sufficient characterization of this assemblage of xanthomonadin pigments is presented so that they can be isolated and identified routinely on the basis of the aforementioned properties.