Bastaxanthins

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

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]. 

In some cases, other spectroscopic methods can be used to identify pigments on the basis of particular structural features. For instance infrared (IR) spectroscopy was used to reveal the presence of an allelic group in the carotenoids fucoxanthin, alloxanthin, and bastaxanthin (Britton et al., 1995). IR spectroscopy was also used to establish the details of the light-induced oxygen-dependent bleaching of the food colorant chlorophyllin (Bertrand et al., 2004 Chenery and Bowring, 2003 Salin et al., 1999). 

Since the first reported naturally occurring carotenoid sulphate by our group in 1981 [67], several examples have been reported from marine sponges, echinoderms and bacteria [68], The first structure established was for bastaxanthin C (27) [69]. The naturally occurring mono- and disulphates so far known contain either... 

Naturally occurring carotenoid sulphates hitherto described contain non-allylic secondary sulphate groups as in the bastaxanthins 352, 365, 411, 420, 423, 431, 431.1 and caloxanthin (182) sulphate (end group a) or as in ophioxanthin (205) (end group b) or a secondary sulphate group a to a carbonyl as in erythroxanthin sulphate (348.3) (end group c). 

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... 

Ophioxanthin and dehydroophioxanthin were isolated separately or simultaneously from the ophiurians Ophiocomina nigra and Ophioderma longicaudum. Sulfated carotenoids are rare other well-known examples are the bastaxanthins of some sponges of the family lanthellidae (see Chapter 19). 

Hertzberg, S., Ramdahl, T., Johansen, J.E., and Liaeen-Jensen, S. (1983) Carotenoid sulfates. 2. Stmctural elucidation of bastaxanthin. 

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