Carotenoid Sulfates. 2. Structural Elucidation of Bastaxanthin.

Publisher Website
Google Scholar
Abstract
The structural elucidation of bastaxanthin, the major carotenoid of the marine sponge Ianthella basta, is reported. Bastaxanthin, the 1st known naturally occurring carotenoid sulfate, was characterized by spectroscopic data (electronic, IR, 1H NMR, 13C NMR, circular dichroism and mass spectra) and chemical evidence (20 sulfated and desulfated derivatives)including acidic and enzymatic hydrolysis to bastaxanthol, also encountered as a minor carotenoid in I. basta. The evidence is consistent with the constitution 3,19,17''-trihydroxy-7,8-didehydro-.beta.,.kappa.-carotene-3'',6''-dione 3-sulfate. The absolute configuration of the 3 chiral centers is discussed in favor of (3R,1''R,5''R)-configuration.