New Trihydroxy-keto-carotenoids Isolated from an Astaxanthin-producing Marine Bacterium

Abstract

Polar orange pigments were extracted from the cultured cells of marine bacterium strain SD-212 and purified by chromatographic methods. The structures of two new trihydroxy-keto-carotenoids, (2R,3S,3'S)-2-hydroxyastaxanthin (1) and (2R,3S,3'R)-2-hydroxyadonixanthin (2) were determined by means of spectral methods. Known carotenoids (3S,2'R,3'R)-erythroxanthin (3), (2R,3S',2' R,3'S)-2,3,2',3'-tetrahydroxy-β,β-carotene-4,4'-dione (4), (2R,3S,2'R,3'R)-2,3,2',3'-tetrahydroxy-β,β-caroten-4-one (5), (3S,3'S)-astaxanthin (6), and (3S,3'R)-adonixanthin (7) were also isolated.

Brevundimonas mediterranea sp. nov., a non-stalked species from the Mediterranean Sea

“…Brevundimonas species are characterized and differentiated from Caulobacter species by the presence of certain glycoand polar lipids, outer-membrane proteins and an increased salt tolerance, but members of the genus show diverse cell morphologies and substrate specificities. Although some marine Brevundimonas strains have been described (Stahl et al, 1992;Yokoyama et al, 1996;Abraham et al, 2002), no marine Brevundimonas species has been named to date. Here we describe six strains isolated from marine water samples, which we propose are representatives of a novel species, Brevundimonas mediterranea sp.…”

Elucidation of a Carotenoid Biosynthesis Gene Cluster Encoding a Novel Enzyme, 2,2′-β-Hydroxylase, from Brevundimonas sp. Strain SD212 and Combinatorial Biosynthesis of New or Rare Xanthophylls

“…Pigments 2 and 3, which also appeared in the control strain, were confirmed to be astaxanthin and adonixanthin by their LC/ APCI-MS and UV-VIS spectral data. Pigment 1 was identified as 2-hydroxyastaxanthin by its LC/APCI-MS, UV-VIS, and 1 H NMR spectral data (55). The stereostructure of the 2-hydroxy group was assigned to be R according to the circular dichroism spectral data of the carotenoids identified in strain SD212 (55).…”

“…Pigment 1 was identified as 2-hydroxyastaxanthin by its LC/APCI-MS, UV-VIS, and 1 H NMR spectral data (55). The stereostructure of the 2-hydroxy group was assigned to be R according to the circular dichroism spectral data of the carotenoids identified in strain SD212 (55). It is therefore clear that ORF11 coded for the novel carotenoid biosynthesis enzyme, carotenoid 2,2Ј-␤-hydroxylase (␤-ring C2-hydroxylase).…”

New carotenoids: Recent progress

“…Two new trihydroxy-keto-carotenoids, (2R,3S,3 H S)-2-hydroxyastaxanthin and (2R,3S,3 H R)-2-hydroxyadonixanthin, were isolated from an astaxanthin-producing marine bacterial strain SD-212, from Japan [7], and had the same chirality at C-3 and C-3 H as the corresponding homologues astaxanthin and adonixanthin, respectively. Erythroxanthin, (3S,2 H R,3 H R)-3,2,3 H -trihydroxy-b,b-caroten-4-one, was also isolated in the free form [7].…”

“…Erythroxanthin, (3S,2 H R,3 H R)-3,2,3 H -trihydroxy-b,b-caroten-4-one, was also isolated in the free form [7]. It had only previously been reported as a sulfate derivative [8].…”