Isolation and Structural Elucidation of (13Z,13‘Z,3R,3‘R,6‘R)-Lutein from Marigold Flowers, Kale, and Human Plasma
- 5 January 1999
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Agricultural and Food Chemistry
- Vol. 47 (2) , 455-461
- https://doi.org/10.1021/jf980823w
Abstract
(13Z,13‘Z,3R,3‘R,6‘R)-Lutein has been isolated and purified from extracts of marigold flowers, fresh raw kale (Brassica oleracea var. Acephala), and human plasma and fully characterized by 1H and 13C NMR, UV/vis, and MS. While the concentration of (13Z,13‘Z)-lutein in kale and human plasma compared to (all-E,3R,3‘R,6‘R)-lutein was found to be quite low, this compound was readily isolated by fractional crystallization of lutein from marigold extracts. Thus, the mother liquors from two consecutive crystallizations of lutein from a saponified extract of marigold flowers were enriched in (13Z,13‘Z)-lutein (8.7% of total carotenoids) and employed for the isolation of this compound by HPLC. The identity of the di-Z-lutein in kale and human plasma has been established by comparison of the HPLC−UV/vis−MS profiles of the purified compounds with those of a fully characterized sample, isolated from marigolds. 3-Hydroxy-β,ε-caroten-3‘-one and 3‘-epilutein have also been identified in extracts from marigolds. Keywords: Brassica oleracea (Acephala); carotenoid metabolites in plants; carotenoid oxidation products; HPLC−mass spectrometry; Z/E (cis/trans)-isomers; marigold flowers; new serum/plasma carotenoids; NMR; Tagetes erecta (orangeade); UV−visibleKeywords
This publication has 11 references indexed in Scilit:
- Chronic ingestion of lycopene-rich tomato juice or lycopene supplements significantly increases plasma concentrations of lycopene and related tomato carotenoids in humansThe American Journal of Clinical Nutrition, 1998
- Inhibitory effects of natural carotenoids, α-carotene, β-carotene, lycopene and lutein, on colonic aberrant crypt foci formation in ratsCancer Letters, 1996
- Isolation, structural elucidation, and partial synthesis of lutein dehydration products in extracts from human plasmaJournal of Chromatography B: Biomedical Sciences and Applications, 1995
- Dietary Carotenoids, Vitamins A, C, and E, and Advanced Age-Related Macular DegenerationJAMA, 1994
- NMR studies on natural all‐trans‐(9′Z,11′Z)‐(3R,3′S,5′R,6′R)‐pyrrhoxanthin, an acetylenic C37‐skeletal nor‐carotenoid butenolideMagnetic Resonance in Chemistry, 1993
- Separation and identification of carotenoids and their oxidation products in the extracts of human plasmaAnalytical Chemistry, 1992
- Effect of food preparation on qualitative and quantitative distribution of major carotenoid constituents of tomatoes and several green vegetablesJournal of Agricultural and Food Chemistry, 1992
- Separation, identification, and quantification of carotenoids in fruits, vegetables and human plasma by high performance liquid chromatographyPure and Applied Chemistry, 1991
- Separation, identification, and quantification of the major carotenoid and chlorophyll constituents in extracts of several green vegetables by liquid chromatographyJournal of Agricultural and Food Chemistry, 1986
- Carotenoid structures, old and new problemsPublished by Walter de Gruyter GmbH ,1985