Glycosides carotenoid

In vivo, one of the main groups of carotenoids are the snlfates of eritoxanthin sulfate and of the caloxanthin sulfates. The sulfates of carotenoids are not associated with pigment-protein complexes, for example, they are neither part of the fight harvesting complexes nor of the reaction centers. In nonphotosynthetic bacteria, carotenoids appear sporadically and when present, they have unique characteristics. Some Staphylococci accumulate C30 carotenoids, flavobacteria C45 and C50, while some mycobacteria accumulate C40 carotenoid glycosides. ... 

Meyer, R, Riesen, R., and Pfander, H., Example 10 carotenoid glycosides and glycosyl esters, in Carotenoids Isolation and Analysis, lA, Britton, G., Liaaen-Jensen, S., Pfander, H., Eds., Birkhauser, Basel, 1995, 277. 

Nakagawa, M. and N. Misawa. 1991. Analysis of carotenoid glycosides produced in gram-negative bacteria by introduction of the Erwinia uredovora carotenoid biosynthesis genes. Agric. Biol. Chem. 55 2147-2148. 

Dembitsky VM. 2005. Astonishing diversity of natural surfactants 3. Carotenoid glycosides and isoprenoid glycolipids. Lipids 40(6) 535-557. 

Yokoyama, A., G. Sandmann, T. Hoshino, K. Adachi, M. Sakai, and Y. Shizuri. 1995. Thermozeaxanthins, new carotenoid-glycoside-esters from thermophilic eubacterium Thermus thermophilus. Tetrahedron Lett. 36 4901 1904. 

Haberli, A. Bircher, C. Pfander, H. (2000) Isolation of a new carotenoid and two new carotenoid glycosides from Curtobacteriumflaccumfacienspvarpoinsettiae. Helv. Chim. Acta, 83, 328-35. 

From a coryneform hydrogen bacterium have been isolated9 the first secondary non-allylic carotenoid glycosides, mono- and di-rhamnosides of zeaxanthin [/3,/3-carotene-3,3 -diol (7)]. These remarkably stable pigments were characterized by... 

Only the spirilloxanthin pathway is found (Tables 1 and 5). Some species have the unusual spirilloxanthin pathway. Hlr. halochloris and Hlr. abdel-malekii contain in addition carotenoid glycosides and their esters as major components. 

Monocyclic Carotenoids.—Aphanizophyll (26) is a new carotenoid glycoside, probably a rhamnopyranoside. It is thus a 4-hydroxy-derivative of myxoxan-thophyll, which might be considered as an intermediate in the formation of 2 -hydroxyflexixanthin (27). However, the presence of flexixanthin (28) and its deoxy-derivative (29) suggests an alternative biogenesis. 

The various parts of Chapter 3 describe the preparation of polyene synthons and the synthesis of different groups of carotenoids, the partial synthesis of carotenoid glycosides, glycosyl esters and sulphates. Technical synthesis and the synthesis of isotopically labelled carotenoids are also covered. 

Carotenoid glycosides are characteristically present, and other trace carotenoids may be present. 

Elimination of some carbons from C40-carotenoid C30" carotenoid C45- and C50" carotenoid Aromatic- carotenoid Carotenoid fatty acid ester Carotenoid glycoside Carotenoid glycoside fatty acid ester Carotenoid sulfate ... 

Usually, carotenoid is used to indicate C4o-compounds consisting of eight isopentenylpyrophosphate (IPP) units. Some variations in carbon numbers of carotenoids are also observed (Table 106.1). Cao-carotenoids are synthesized by the combination of two famesol instead of the usual geranylgeraniol unit. C45- and Cso-carotenoids are synthesized by the addition of one and two IPP units to C4o-carotenoids, respectively. Unique carotenoid derivatives, such as carotenoid glycoside fatty acid esters and carotenoid sulfates, are also distributed in specific organisms (Table 106.1). 

Cyanobacteria contain unique ketocarotenoids, such as echinenone 51 and 4-ketomyxol glycoside 84, and carotenoid glycosides. Usually, the glycoside moieties are methylpentoses, fucose, rhamnose, and chinovose [13]. 

Takaichi S, Mochimaru M (2007) Carotenoids and carotenogenesis in cyanobacteria unique ketocarotenoids and carotenoid glycosides. Cell Mol Life Sci 64 2607-2619... 

S Takaichi, J Ishundu. Carotenoid glycoside ester from Rhodococcus rhodochrous. Methods Enzymol 213 366-374, 1992. 

DR KuU, H Pfander. Isolation and structure elucidation of carotenoid glycosides from the thermoacidophUic Archaea Sulfolobus shibatae. J Nat Prod 60 371-374, 1997. 

Scheme 17 Synthesis of a carotenoid glycoside, 42, by Ferrier rearrangement.

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