ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Carotenoids from Hips of Rosa pomifera: Discovery of (5Z)-Neurosporene; Synthesis of (3R, 15Z)-RubixanthinExtensive 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): (15 Z)-phytoene (1), (15 Z)-phytofluene (2), all-(E)-phytofluene (2a), ξ-carotene (3), two mono-(Z)-ξ-carotenes (3a and 3b), (6 R)-∊, ψ-carotene (4), a mono-(Z)-∊, ψ-carotene (4a), β, ψ-carotene (5), a mono-(Z)-β, ψ-carotene (5a), neurosporene (6), (5 Z)-neurosporene (6a), a mono-(Z)-neurosporene (6b), lycopene (7), five (Z)-lycopenes (7a-7e), β, β-carotene (8), two mono-(Z)-β, β-carotenes (probably (9 Z)-β, β-carotene (8a) and (13 Z)-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 (13 Z)-rubixanthin (10c and 10d, resp.), (5′ Z, 13′ Z)- or (5′ Z, 13 Z)-rubixanthin (10e), lutein (11), zeaxanthin (12), (13 Z)-zeaxanthin (12b), a mono-(Z)-zeaxanthin (probably (9 Z)-zeaxanthin (12a)), (8 R)-mutatoxanthin (13), (8 S)-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 easily be distinguished by HPLC. separation and CD. spectra at low temperature. The synthesis of (3 R, 15 Z)-rubixanthin (29) is described.The isolation of (5 Z)-neurosporene (6a) supports the hypothesis that the ∊-end group arises by enzymatic cyclization of precursors having a (5 Z)- or (5′ Z)-configuration.
Additional Material:
9 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19830660211
