The Soluble Blue Pigment, Indochrome, of Arthrobacter polychromogenes

Abstract

The production and purification of indochrome, the soluble pigment from Arthrobacter polychromogenes, is described. Four isomeric 3-hydroxy-6-d-ribosyl-2-aza-benzoquinone-(1,4)-4-[2,6-dihydroxy-5-d-ribosyl-pyridyl-(3)-imides] have been isolated from the natural product as the main components. In indochrome A two β-d-ribopyranosyl residues, in indochrome B II two β-d-ribofuranosyl residues, are bound to the aglycone. The pigment fractions B I and B III contain differently configurated d-ribosyl residues, which for B I were found to be the α- and β-configurations of the pyranose form. Nitric acid degradation of the pigment and condensation with phenylhydrazine yields mainly 3-β-d-ribopyranosyl-5-benzeneazo-2,6-dihydroxy-pyridine. All d-ribopyranosyl residues were found to be in the C1(D) conformation. d-Ribose was liberated from the aglycones by ozonolysis

Bacteria belonging to the extremely versatile genus Arthrobacter as novel source of natural pigments with extended hue range

“…Apart from indigoidine, another chromophore of the water-soluble pigment produced by A. atrocyaneus and A. polychromogenes was identified as indochrome (Knackmuss, 1973;Knackmuss et al, 1969). This pigment was released into the liquid culture only by indigoidineproducing bacteria.…”

“…This pigment was released into the liquid culture only by indigoidineproducing bacteria. It has been initially described by Knackmuss et al (1969) who analyzed its chemical structure.…”

“…nov., Arthrobacter aurescens, Arthrobacter ilicis, Arthrobacter citreus, A. nicotianae, Arthrobacter arilaitensis, Arthrobacter protophormiae, A. uratoxydans, Arthrobacter sulfureus, A. luteolus and A. mysorens) (Chang et al, 2007;Irlinger et al, 2005;Kallimanis et al, 2009;Reddy et al, 2000), green (Arthrobacter crystallopoietes sp. nov., A. pyridinolis, A. viridescens) (Ensign & Rittenberg, 1963;Knackmuss & Beckmann, 1973;Kolenbrander & Weinberger, 1977;Schippers-Lammertse et al, 1963), blue (Arthrobacter oxydans, A. atrocyaneus, Arthrobacter polychromogenes) (Knackmuss, Cosens, & Starr, 1969;Kuhn & Starr, 1960) and red (Arthrobacter roseus sp. nov., A. agilis, A. hyalinus) (Fong, Burgess, & Barrow, 2001;Kojima et al, 1993;Reddy et al, 2000).…”

Investigation of Indigoidine Synthetase Reveals a Conserved Active-Site Base Residue of Nonribosomal Peptide Synthetase Oxidases

“…[12][13][14][15] Indigoidine synthetase genes have been engineered and introduced into living systems to construct a cross-kingdom reporter system 16 , generate blue rose 17 , and produce 2 as a promising water-insoluble dye 18,19 . Interestingly, indigoidine synthetase genes are widely distributed in bacteria, including Actinobacteria and Proteobacteria ( Figure S1), and frequently colocalized with genes encoding enzymes that glycosylate C-5 of 1, leading to the water-soluble blue pigment indochrome 20,21 , and the C-nucleoside antibiotic, minimycin 13 (Figure 1b). As such, indigoidine synthetases are involved in biosynthesis of a broad range of bacterial secondary metabolites.…”

Molecular evolution of the bacterial pseudouridine‐5′‐phosphate glycosidase protein family

“…In addition, an early C-ribosylation step would be better suited to explain the formation of the soluble pigment indochrome B1 (Fig. 5C), which has been isolated from Arthrobacter polychromogenes over four decades ago [19]. Other than indochrome B1, we note that enzymes of the PsiMP glycosidase family might be involved in the biosynthesis of certain C-nucleotide antibiotics [20][21][22][23], which contain C-glycosidally linked ribose units.…”