The carbohydrate moieties bound to the carotenoids myxol and oscillol and their chemosystematic applications

Foss, Per; Skulberg, Olav M.; Kilaas, Lars; Liaaen‐Jensen, Synnøve

doi:10.1016/s0031-9422(00)81568-x

Cited by 26 publications

(8 citation statements)

References 15 publications

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“…sides are found only in some cyanobacteria (Hirschberg & Chamovitz, 1994;Takaichi & Mochimaru, 2007, 2009), for example oscillol 2,29-difucoside and oscillol 2,29-dirhamnoside in Oscillatoria agardhii (Foss et al, 1986), and (2S,29S)-oscillol 2,29-di-(a-L-fucoside) in Gloeobacter violaceus (Tsuchiya et al, 2005). The present identification of oscillol 2,29-dirhamnoside in G. aurantiaca is the first in a bacterial phylum other than in cyanobacteria.…”

Section: S Takaichi and Othersmentioning

confidence: 56%

Carotenoids of Gemmatimonas aurantiaca (Gemmatimonadetes): identification of a novel carotenoid, deoxyoscillol 2-rhamnoside, and proposed biosynthetic pathway of oscillol 2,2′-dirhamnoside

et al. 2010

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Gemmatimonas aurantiaca strain T-27 T is an orange-coloured, Gram-negative, facultatively aerobic, polyphosphate-accumulating bacterium belonging to a recently proposed phylum, Gemmatimonadetes. We purified its pigments and identified them as carotenoids and their glycoside derivatives using spectral data. The major carotenoid was (2S,29S)-oscillol 2,29-di-(a-Lrhamnoside), and the minor carotenoids were (2S)-deoxyoscillol 2-(a-L-rhamnoside) and didemethylspirilloxanthin. Deoxyoscillol 2-rhamnoside is a novel carotenoid. Oscillol 2,29-diglycosides have hitherto only been reported in a limited number of cyanobacteria, and this is believed to be the first finding of such carotenoids in another bacterial phylum. Based on the identification of the carotenoids and the completion of the entire nucleotide sequence, we propose a biosynthetic pathway for the carotenoids and the corresponding genes and enzymes. We propose the involvement of geranylgeranyl pyrophosphate synthase (CrtE), phytoene synthase (CrtB) and phytoene desaturase (CrtI) for lycopene synthesis; and of carotenoid 1,2-hydratase (CruF) and carotenoid 2-O-rhamnosyltransferase (CruG) for oscillol 2,29-dirhamnoside synthesis. Further, isopentenyl pyrophosphate could be synthesized by a non-mevalonate pathway (DXP pathway).

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Section: S Takaichi and Othersmentioning

confidence: 56%

Carotenoids of Gemmatimonas aurantiaca (Gemmatimonadetes): identification of a novel carotenoid, deoxyoscillol 2-rhamnoside, and proposed biosynthetic pathway of oscillol 2,2′-dirhamnoside

et al. 2010

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“…The structures of myxoxanthophyll and oscillaxanthin from Arthrospira sp. were ultimately determined to be myxol 2-rhamnoside and oscillol 2,2-di(L-rhamnoside) [27,28], respectively, although the glycoside moiety of rhamnoside was reidentified as chinovoside [29]. The determination of the sugar moieties of these carotenoids, including the L-or D-type and the a-or b-linkage, has been made only for a few species of cyanobacteria.…”

Section: Myxol Glycosides In Cyanobacteriamentioning

confidence: 99%

Carotenoids and carotenogenesis in cyanobacteria: unique ketocarotenoids and carotenoid glycosides

Takaichi

Mochimaru

2007

Cell. Mol. Life Sci.

172

126

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Cyanobacteria grow by photosynthesis, and necessarily contain chlorophyll and carotenoids, whose main functions are light harvesting and photoprotection. In this review, we discuss the carotenoids, carotenogenesis pathways, and characteristics of carotenogenesis enzymes and genes in some cyanobacteria, whose carotenogenesis enzymes have been functionally confirmed. In these cyanobacteria, various carotenoids have been identified, including the unique ketocarotenoids, echinenone and 4-ketomyxol; and the carotenoid glycosides, myxol glycosides and oscillol diglycosides. From these findings, certain carotenogenesis pathways can be proposed. The different compositions of carotenoids among these species might be due to the presence or absence of certain gene(s), or to different enzyme characteristics. For instance, two distinct beta-carotene ketolases, CrtO and CrtW, are properly used in two pathways depending on the species. One beta-carotene hydroxylase, CrtR, has been identified, and its substrate specificities vary across species. At present, functionally confirmed genes have been found in only a few species, and further studies are needed.

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“…The structure was determined as a mixed carotenoid glycoside in which rhamnose is the dominant sugar moiety and a hexose is a minor component (17). Until now, several myxol glycosides with fucose derivatives have been found, including myxol 2Ј-(3-O-methyl-␣-L-fucoside) in Oscillatoria bornetii (16), the nonmethylated myxol 2Ј-␣-L-fucoside from Oscillatoria limnetica (1), and myxol 2Ј-dimethyl fucoside in Synechocystis sp. strain PCC 6803 (53).…”

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

et al. 2005

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Myxoxanthophyll is a carotenoid glycoside in cyanobacteria that is of unknown biological significance. The sugar moiety of myxoxanthophyll in Synechocystis sp. strain PCC 6803 was identified as dimethyl fucose. The open reading frame sll1213 encoding a fucose synthetase orthologue was deleted to probe the role of fucose and to determine the biological significance of myxoxanthophyll in Synechocystis sp. strain PCC 6803. Upon deletion of sll1213, a pleiotropic phenotype was obtained: when propagated at 0.5 mol photons m ؊2 s ؊1 , photomixotrophic growth of cells lacking sll1213 was poor. When grown at 40 mol photons m ؊2 s ؊1 , growth was comparable to that of the wild type, but cells showed a severe reduction in or loss of the glycocalyx (S-layer). As a consequence, cells aggregated in liquid as well as on plates. At both light intensities, new carotenoid glycosides accumulated, but myxoxanthophyll was absent. New carotenoid glycosides may be a consequence of less-specific glycosylation reactions that gained prominence upon the disappearance of the native sugar moiety (fucose) of myxoxanthophyll. In the mutant, the N-storage compound cyanophycin accumulated, and the organization of thylakoid membranes was altered. Altered cell wall structure and thylakoid membrane organization and increased cyanophycin accumulation were also observed for ⌬slr0940K, a strain lacking -carotene desaturase and thereby all carotenoids but retaining fucose. Therefore, lack of myxoxanthophyll and not simply of fucose results in most of the phenotypic effects described here. It is concluded that myxoxanthophyll contributes significantly to the vigor of cyanobacteria, as it stabilizes thylakoid membranes and is critical for S-layer formation.

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The carbohydrate moieties bound to the carotenoids myxol and oscillol and their chemosystematic applications

Cited by 26 publications

References 15 publications

Carotenoids of Gemmatimonas aurantiaca (Gemmatimonadetes): identification of a novel carotenoid, deoxyoscillol 2-rhamnoside, and proposed biosynthetic pathway of oscillol 2,2′-dirhamnoside

Carotenoids of Gemmatimonas aurantiaca (Gemmatimonadetes): identification of a novel carotenoid, deoxyoscillol 2-rhamnoside, and proposed biosynthetic pathway of oscillol 2,2′-dirhamnoside

Carotenoids and carotenogenesis in cyanobacteria: unique ketocarotenoids and carotenoid glycosides

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

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