Minor Carotenoid Sulfates from lanthella basta

Biochemical Systematics and Ecology
1983.0

Abstract

The structural elucidation of the minor carotenoid sulfates from the marine sponge lanthella basra is discussed in context with the structure assigned to the major sulfate bastaxanthin (c; 3,19,17"-trihydroxy-7,8-didehydro-fJ-~-carotene-3", 6" dione 3-sulfate). Plausible structures are assigned to other bastaxanthins (b, b 2, c 2, d, e and f) on the basis of electronic, IR, 1H NMR, mass and CD spectra, electrophoretic behaviour, chemical derivatization and enzymatic or acid-catalysed hydrolysis. The minor sulfates represent structural variation in the cyclopentane end group with different oxidation levels. Bastaxanthol b (desulfated bastaxanthin b) was a minor carotenoid constituent of L basta. Including tentative chiralities, the structures favoured for the bastaxanthins are: c2, (3R,3'R,5"R)-3,19,3'-trihydroxy-7,8-didehydro-~,x-caroten-6'-one 3-sulfate; b 2, (3R,3'R,5'R)-3,19-dihydroxy-7,8-didehydro-~,x-carotene-3",6'-dione 3-sulfate; b, (3R,1'R,5'R)-3,19-dihydroxy-3',6'-dioxo-7,8-didehydro-f],~-caroten-17'-al 3-sulfate; d, (3R, l'R,3"R,5'R)-3,19,3',17'-tetrahydroxy-7,8-didehydro-f3,~-caroten-6'-one 3-sulfate; e, hydrogen (3R, l"R,5'R)-3,19-dihydroxy-3',6'-dioxo-7,8-didehydro-ft,x-caroten-17'-oate 3-sulfate (?); and f, hydrogen (3R,1'R,3'R,5'R)-3,19,3'-trihydroxy-7,8-didehydro-6'-oxo-f],x-caroten-17'-oate 3-sulfate; for bastaxanthol b (3R,1'R,5"R)-3,19-dihydroxy-3',6'-dioxo-7,8-didehydro-fJ,x-caroten-17'-al. The bastaxanthins are considered as metabolic products of L basta, diadinoxanthin of phytoplankton origin representing a plausiable precursor.

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