Bacterial carotenoids, XLVI. C50-Carotenoids, 14. C50-Carotenoids from Arthrobacter glacialis

From the psychrophilic bacterium Arthrobacter glacialis have been isolated three C50-carotenoids with molecular formulae C50H72O2: the bicyclic decaprenoxanthin (1a, 7% of total carotenoids), the aliphatic bisanhydrobacterioruberin (2a, 10%) and the monocyclic A.g. 470 (3a, 83%). Decaprenoxanthin (1) and bisanhydrobacterioruberin (2) were in all respects, including chiroptical properties, identical with known carotenoids. The constitution of the previously undescribed A.g. 470 (3a) followed from its spectral properties (electronic, 1H NMR including Eu-shift experiments and mass spectra) and derivatization to 3b and 3c. 3a suffered remarkable elimination to the tridecaene 4a (C47H64O) upon DMSO/KOMe/MeOH treatment. Judged by CD data A.g. 470 (3a) also in stereochemical respect 3a appears to be half decaprenoxanthin (1a)+half bisanhydrobacterioruberin (2a). The intensity ratios of the M-92/M-106 ions on electron impact of 3a,b,c and 4a,b are consistent with the general theory.