43. Das Carotinoidspectrum der Hagebutten von Rosa pomifera: Nachweis von (5Z)-Neurosporin; Synthese von (3R,15Z)-Rubixanthin

Article abstract of DOI:10.1002/hlca.19830660211

Extensive chromatographic separations of the mixture of carotenoids from ripe hips of R. pomifera have led to the identification of 43 individual compounds, namely (Scheme 2): (15Z)-phytoene (1), (15Z)-phytofluene (2), all-(E)-phytofluene (2a), ξ-carotene (3), two mono-(Z)-ξ-carotenes (3a and 3b), (6R)-ε,ψ-carotene (4), a mono-(Z)-ε,ψ-carotene (4a), β,ψ-carotene (5), a mono-(Z)-β,ψ-carotene (5a), neurosporene (6), (5Z)-neurodporene (6a), a mono-(Z)-neurosporene (6b), lycopene (7), five (Z)-lycopenes (7a-7e), β,β-carotene (8), two mono-(Z)-β,β-carotenes (probably (9Z)-β;β-carotene (8a) and (13Z)-β,β-carotene (8b)), β-cryptoxanthin (9), three (Z)-β-cryptoxanthins (9a-9c), rubixanthin (10), (5'Z)-rubixanthin (=gazaniaxanthin; 10a), (9'Z)-rubixanthin (10b), (13'Z)- and (13Z)-rubixanthin (10c and 10d, resp.), (5'Z, 13'Z)- or (5'Z,13Z)-rubixanthin (10e), lutein (11), zeaxanthin (12), (13Z)-zeaxanthin (12b), a mono-(Z)-zeaxanthin (probably (9Z)-zeaxanthin (12a)), (8R)-mutatoxanthin (13), (8S)-mutatoxanthin (14), neoxanthin (15), (8'R)-neochrome (16), (8'S)-neochrome (17), a tetrahydroxycarotenoid (18?), a tetrahydroxy-epoxy-carotenoid (19?), and a trihydroxycarotenoid of unknown structure.Rubixanthin (10) and (5'Z)-rubixanthin (10a) can be easily distinguished by HPLC. separation and CD. spectra at low temperature.The synthesis of (3R, 15Z)-rubixanthin (29) is described.The isolation of (5Z)-neurosporene (6a) supports the hypothesis that the ε-end group arises by enzymatic cyclization of precursors having a (5Z)- or (5'Z)-configuration.