Carotenoid pigments from Rhodococcus rhodochrous RNMS1: Two monocyclic carotenoids, a carotenoid monoglycoside and carotenoid glycoside monoesters.

Abstract

Four kinds of carotenoid pigments were found in Rhodococcus rhodochrous RNMS1. Spectroscopic and chemical evidence showed two of them to be monocyclic carotenoids each containing a tertiary hydroxyl group at Cr, and their structures were determined as r,2'-dihydro-/J,^-caroten-rol and r-hydroxy-r,2'-dihydro-/?,^r-caroten-4-one. The other two were novel carotenoid derivatives, one being a monoglycoside of the latter carotenoid and the other monoesters of this carotenoid glycoside, which were esterified with nine major fatty acids at the C6 hydroxyl group of the glucose moiety. The fatty acids consisted of four saturated (C16 : 0-C19 : 0), four mono-unsaturated (C18 : 1-C21 : l) and one branched-chain (10-methyl C19: 0) acid, including the odd-numbered ones. The structures were determined to be r-[(^-D-glucopyranosyl)oxy]-r,2'-dihydro-^,^r-caroten-4-one and r-[(6-0-acyl-0-D-glucopyranosyl)oxy]-1^2 ' Klihydro-/^-caroten-4-one. Rhodococcus rhodochrous RNMS1 , formerly called "Bacillus megaterium roseus" B3-9,1'2) forms light orange colored colonies. Wehave already found that pigments causing this color belonged to several carotenoids.3) Colonies of other species of the Rhodococcus genus are known to be red, orange or pink colored.4) Recently, Ichiyama et al. have reported the presence of carotenoids in several species of the Rhodococcus genus.5) However, conclusive identification of these carotenoids has not be undertaken.

Biotechnology of Rhodococcus for the production of valuable compounds

“…BS32 Cells growing on rapeseed oil Production of extracellular biosurfactants Ruggeri et al 2009 R. erythropolis sp. P6-4P Cells growing on fish waste compost Production of biosurfactant that is mainly composed of fatty acids Kazemi et al 2009 Bioflocculants R. erythropolis S-1 Cells growing on sorbitol, mannitol, ethanol, glucose, or fructose Production of the peptidic bioflocculant named NOC-1, it is one of the best performing bioflocculant described up to date Kurane et al 1994 R. erythropolis ATCC 10543 Cells growing on pre-treated sludge and livestock wastewater Production of a polysaccharidic bioflocculant Peng et al 2014 R. erythropolis Cells growing on potato starch wastewater Production of a polysaccharidic bioflocculant Guo et al 2018 Carotenoids R.luteus , R. coprhilus , R. lentifragmentus , R. maris Cells growing on Sauton agar medium Production of β-carotene Ochiyama et al 1989 R. equi , R. rubroperctinctus , R. aichiensis , R. sputi , R. chubuensis , R. obuensis , R. bornchialis , R. roseus , R. rhodochrous , R. rhodnii , R. terrae Cells growing on defined medium l -asparagine and glycerol as main nitrogen and carbon sources, respectively Production of γ-carotene-like compound Ochiyama et al 1989 R. erythropolis IBBPo1 Cells growing on n -alkane Production of lycopene at higher level Stancu et al 2015 R. rhodochrous RNMS1 ND Production of γ-carotene derivatives Takaichi et al 1990 R. erythropolis AN12 Cells growing on rich medium (i.e., nutrient broth-based medium) Production of γ-carotene derivatives Tao et al 2004 Rhodococcus sp. CIP Cells growing on rich medium Production ...…”

Myxoxanthophyll Is Required for Normal Cell Wall Structure and Thylakoid Organization in the Cyanobacterium Synechocystis sp. Strain PCC 6803

“…3B) indicate a mix of myxol and lycopene derivatives (Fig. 4, spectra 2 and 3) with different glycosylation and methylation patterns, neither of which affect the absorption spectra of the carotenoids (48,49).…”

Carotenoids in a Corynebacterineae,Gordonia terraeAIST-1: Carotenoid Glucosyl Mycoloyl Esters

“…Four strains of R. rhodochrous have been found to contain 1 0 -hydroxy--carotene, its 4-keto form, their glucoside, their glucosyl acyl esters, and their glucosyl mycoloyl esters. 11,12) The difference in the carotenoid moiety is the absence of the C-2 0 hydroxyl group and the C-3 0 ,4 0 single bond in deoxymyxol from G. terrae. R. rhodochrous was the first species found to have carotenoid glucosyl mycoloyl esters, and G. terrae is the second one in organisms.…”

“…Accordingly, the major esterified mycolic acid moieties were compatible with C56:4, C58:4, and C60:4 respectively. The 1 H NMR spectrum of the peak 7 carotenoids in CDCl 3 indicated that the carotenoid moiety was compatible with DM-G. A doublet signal at 4.58 ppm (J ¼ 8 Hz) indicated the presence of -D-glucoside, and broad doublet signals at 4.29 and 4.51 ppm, which shifted to the lower field region, as compared with the signals of C-6 00 of carotenoid glucoside, 11) indicated that the esterified hydroxyl group was C-6 00 of glucoside. The presence of mycolic acid was indicated by signals at 0.88 ppm (triplet), 2.44, 3.67, and 1.39 ppm (multiplet), and at 1.25 ppm.…”

“…We have identified all of its carotenoids, including 1 0 -hydroxy--carotene and its 4-keto form, their glucosides, their glucosyl acyl esters, and their glucosyl mycoloyl esters. 11,12) This was the first species found to have carotenoid glucosyl mycoloyl esters. 10) Lowering the y To whom correspondence should be addressed.…”