Isolation of an Unusually Stable Cis-Isomer of Alloxanthin from a Bleached Autolysed Culture of Chroomonas salina Grown Photoheterotrophically on Glycerol. Observations on Cis-Trans Isomerization of Alloxanthin

SYNOPSIS. A new carotenoid, manixanthin , was isolated from a bleached, autolysed culture of the marine cryptomonad Chroomonas salina grown on glycerol in light, after the culture showed disappearance of the chlorophylls and carotenoids normally produced. Manixanthin lacked carbonyl, ester, and epoxy groups in chemical tests, whilst its spectroscopic properties indicated a conjugated nonaene chromophore. In its chromatographic mobility, manixanthin closely resembled alloxanthin, the major normal xanthophyll of the cryptomonad. The iodine-catalysed photostereomutation of manixanthin produced the same equilibrium mixture of cis -isomers as that given by similar treatment of alloxanthin. This mixture of isomers completely lacked the all-trans alloxanthin and contained ∼60% manixanthin. It was concluded that manixanthin is an unusually stable cis -isomer of alloxanthin, and is presumably produced in the culture medium by the action of light on alloxanthin released by autolysed cells of the cryptomonad. The unusual stability of manixanthin relative to alloxanthin was investigated by effecting partial stereoisomerizations under conditions using either of heat, light, or iodine, and evidence was obtained for a series of at least 10 isomers with a trend of stability increase from alloxanthin to manixanthin. It was inferred that manixanthin may be 9,9'-di cis -alloxanthin.