Carotenoids isolation

Schiedt, K. and Liaaen-Jensen, S., Isolation and analysis, in Carotenoids Isolation and Analysis, lA, Britton, G., Liaaen-Jensen, S., and Pfander, H., Eds., Birkhauser, Basel, 1995, 81. 

Weedon, B. C. L. and G. P. Moss (1995). Structure and nomenclature. Carotenoids, Isolation and Analysis. G. Britton, S. Liaaen-Jensen and H. Pfander, eds. Basel, Switzerland Birkauser Verlag, pp. 1A. 

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]. 

Chapman, V.J. (1966) Three new carotenoids isolated from algae. Phytochemistry 5,... 

The structure of a new carotenoid, isolated from fruits of the red tomato-shaped paprika, was elucidated to be (3S,5f ,6S,59P)-3,6-epoxy-5,6-dihydro-5-hydroxy-P, carotenes, 6 -dione by spectroscopic analyses and mass spectrometry and was designated as capsanthone 3,6-epoxide. Capsanthone 3,6-epoxide is assumed to be an oxidative metabolite of capsanthin 3,6-epoxide in paprika (Maoka et al., 2001a). 

Britton G., Liaaen-Jensen S., and Pfander H. (1995) Carotenoids today and challenges for the future. In Carotenoids Isolation and Analysis, Birkhauser, vol. la, pp. 13-26. 

The 3-hydroxy-K end group is characteristic of capsorubin (28), and other carotenoids isolated from paprika (Capsicum annuum). All syntheses are based on the Cio + C2o + Cio = C4o strategy, and use crocetindialdehyde (27) as central building block and the aldol condensation as the coupling reaction Scheme 6). The synthesis of optically active capsorubin (28), reported in 1973, was the first synthesis of an enantiomerically pure xanthophyll [11]. For the optically active form of the key building block, the frans-Cio-hydroxyketone 26, two approaches have been reported. In the first reaction sequence, (+)-camphor (143) was converted into camphoric acid (144) by treatment with nitric acid. Camphoric acid (144) was then esterified with dimethyl sulphate... 

Vacheron, M.J., G. Michel, R. Guilluy, and N. Arpin Etude par Spectrometrie de Masse d un Carotenoide Isole d un Discomycete, Plectania coccinea. Phytochem. 8, 897 (1969). 

Carotenoid isolation is carried out in open-column chromatography (OCC). OCC should be carried out under a fume hood to protect the analyst from inhaling solvent vapor. Breathing hexane, for example, should be avoided due to neurotoxicity of some of its oxidative metabolites [87]. The isolation procedure is as follows. 

FIGURE 13.3. Chemical structures of carotenoids isolated from marine sources. 

Dinochromes A and B are particular carotenoids isolated from the freshwater species Peridinium bipes collected in Japan. Dinochrome A showed antiproliferative activity against three human tumor cells GOTO (neuroblastoma) OST (osteosarcoma), and He La (cervical cancer) (Maoka, Tsushima, and Nishino, 2002). 

Three aromatic carotenoids and one transposed carotenoid have been isolated from Agelas mauritiana and A. schmidtii. None of them is identical to the carotenoids isolated from Hadromerida (see above). 

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