The supramolecular structure of self-assembly formed by capsanthin derivatives.
Carotenoids form structured self-assembly upon aqueous dilution of their organic solutions. In order to test the proposal predicting carotenoid aggregates to be organized in closely packed H-type (card-pack) manner by intermolecular hydrogen bonds, the trihydroxy derivative of capsanthin (1), (6'R)-capsanthol (2) ((all-E,3R,3'S,5'R,6'R)-beta,kappa-carotene-3,3',6'-triol) was acetylated to obtain all varieties of mono-, di- and triacetates and the corresponding supramolecules were studied by UV/Vis- and CD spectroscopy. It was verified that derivatives lacking hydroxyl functions at either of the end-groups form the loosely organized J-type (head-to-tail) aggregates. A model for the structure of the J-type self-assembly is proposed. Evidence was also obtained suggesting that close contacts of carotenoid molecules are not confined to hydrogen bonding.
Bikádi
Zsolt
Z
Department of Molecular Pharmacology, Institute of Chemistry, Chemical Research Center, Hungarian Academy of Sciences, Budapest.
Zsila
Ferenc
F
Deli
József
J
Mády
György
G
Simonyi
Miklós
M
D002212:Capsicum / Q000378:metabolism; D002338:Carotenoids / Q000096:biosynthesis / Q000737:chemistry*; D002850:Chromatography, Gel; D002942:Circular Dichroism; D006860:Hydrogen Bonding; D046911:Macromolecular Substances; D008958:Models, Molecular; D015394:Molecular Structure; D013056:Spectrophotometry, Ultraviolet; D024341:Xanthophylls
D046911:Macromolecular Substances; D024341:Xanthophylls; D002338:Carotenoids; C006889:capsanthin