Carotenoid sulfates

Hertzberg S and Liaaen-Jensen S. 1985. Carotenoid sulfates 4. Syntheses and properties of carotenoid sulfates. Acta Chemica Scandinavica Series B—Organic Chemistry and Biochemistry 39(8) 629-638. 

Hertzberg S, Ramdahl T, Johansen JE, and Liaaen-Jensen S. 1983. Carotenoid sulfates 2. Structural elucidation of bastaxanthin. Acta Chemica Scandinavica B37 267-280. 

Yokyoyama A and Shizusato Y. 1997. Carotenoid sulfate and its production, Kaiyo Biotechnology, Kenkyusho, Japan. JP 9084591. 

Bastaxanthins B, C, D, E, and F (630-634) are novel carotenoid sulfates from the marine sponge Ianthella basta from the Great Barrier Reef, Australia [499]. The stereostructure of bastaxanthin C (631) was determined on the basis of infrared (IR), H and 13C NMR, and CD spectra, and by chemical transformations [500]. Bastaxanthins were also isolated from /. flabelliformis from the Great Barrier Reef including bastaxanthin C (631) (major), B (630), D (632), and F (634) and bastaxanthin G (635) [501]. Bastaxanthin G (635) was not fully characterised but was the most polar of the carotenoids isolated and was tentatively described as a disulfate [501]. 

A carotenoid sulfate, ophioxanthin (666), was isolated from the ophiuroid Ophioderma longicaudum from the Mediterranean Sea and shown to be 5,6,5 ,6 -tetrahydro-P,P-carotene-3,4,3 ,4-tetraol 4,4 -disulfate [528]. The carotenoid, dehydroophioxanthin (667) was isolated from the ophiuroid Ophiocomina nigra off Spain and the structure was determined by spectral data analysis [529]. 

The Rhodospirillaceae and Chromatiaceae have the spirilloxanthin or the okenone pathway depending on the genus or species. All of the Ectothiorhodospiraceae have the spirilloxanthin pathway. The isorenieratene, the y-and -carotene, and the diapocarotene pathways are found specifically in the Chlorobiaceae, Chloroflexaceae, and Heliobacteriaceae, respectively. Aerobic photosynthetic bacteria mostly have the spirilloxanthin pathway, further most of these species have unusual carotenoids including non-photosynthetic carotenoids, such as carotenoid sulfates and carotenoic acids, which have no photosynthetic functions. 

See Table 1 Acid carotenoic acid C3Q 4,4 -diapocarotene derivatives Erb-type carotenoid sulfate(s), )3-carotene and its hydroxyl derivatives, y-carotene and its cross-conjugated aldehyde, and spirilloxanthin type. 

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). 

In studies on carotenoid sulfates, the sodium salts of lycoxanthin sulfate 53 and zeaxanthin sulfate 54 were synthesised by treatment of lycoxanthin 55 or zeaxanthin 56 with chlorosulfonic acid in pyridine, followed by reaction with aqueous sodium hydroxide. ... 

Several carotenoids have been isolated from marine sponges 142), for example the main carotenoids of Microciona prolifera 143) and a carotenoid sulfate, bastaxanthin (222a), from lanthella basta 144). Bastaxanthin (222a) was the first known naturally occurring carotenoid sulfate. 

Hertzberg, S., T. Ramdahl, J.E. Johansen, and S. Liaaen-Jensen Carotenoid Sulfates. 2. Structural Elucidation of Bastaxanthin. Acta Chem. Scand. B 37, 267... 

D Auria, M.V., R. Riccio, and L. Minale Ophioxanthin, a New Marine Carotenoid Sulfate from the Ophiuroid Ophioderma longicaudum. Tetrahedron Lett. 26, 1871 (1985). 

D Auria, M.V., Minale, L., Ricdo, R., and Uriarte, E. (1991) Dehydroophioxanihin, a new acetylenic carotenoid sulfate from the ophiuroid Ophiocomina nigra. J. Nat. Prod., 54,606-608. 

Hertzberg, S., Ramdahl, T, Johansen, J.E., and Liaeen-Jensen, S. (1983) Carotenoid sulfates. 2. Structural elucidation of bastaxanfhin. Acta Chem. Scand., B37, 267-280. 

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