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Isolation and structural elucidation of (13Z,13'Z,3R,3'R,6'R)-lutein from marigold flowers, kale, and human plasma.
J Agric Food Chem. 1999 Feb; 47(2):455-61.JA

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 (1)H and (13)C 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-beta,epsilon-caroten-3'-one and 3'-epilutein have also been identified in extracts from marigolds.

Authors+Show Affiliations

Department of Chemistry and Biochemistry, Joint Institute for Food Safety and Applied Nutrition (JIFSAN), University of Maryland, College Park 20742, USA. fk17@umail.umd.eduNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

10563916

Citation

Khachik, F, et al. "Isolation and Structural Elucidation of (13Z,13'Z,3R,3'R,6'R)-lutein From Marigold Flowers, Kale, and Human Plasma." Journal of Agricultural and Food Chemistry, vol. 47, no. 2, 1999, pp. 455-61.
Khachik F, Steck A, Pfander H. Isolation and structural elucidation of (13Z,13'Z,3R,3'R,6'R)-lutein from marigold flowers, kale, and human plasma. J Agric Food Chem. 1999;47(2):455-61.
Khachik, F., Steck, A., & Pfander, H. (1999). Isolation and structural elucidation of (13Z,13'Z,3R,3'R,6'R)-lutein from marigold flowers, kale, and human plasma. Journal of Agricultural and Food Chemistry, 47(2), 455-61.
Khachik F, Steck A, Pfander H. Isolation and Structural Elucidation of (13Z,13'Z,3R,3'R,6'R)-lutein From Marigold Flowers, Kale, and Human Plasma. J Agric Food Chem. 1999;47(2):455-61. PubMed PMID: 10563916.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Isolation and structural elucidation of (13Z,13'Z,3R,3'R,6'R)-lutein from marigold flowers, kale, and human plasma. AU - Khachik,F, AU - Steck,A, AU - Pfander,H, PY - 1999/11/24/pubmed PY - 2000/9/19/medline PY - 1999/11/24/entrez SP - 455 EP - 61 JF - Journal of agricultural and food chemistry JO - J. Agric. Food Chem. VL - 47 IS - 2 N2 - (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 (1)H and (13)C 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-beta,epsilon-caroten-3'-one and 3'-epilutein have also been identified in extracts from marigolds. SN - 0021-8561 UR - https://www.unboundmedicine.com/medline/citation/10563916/Isolation_and_structural_elucidation_of__13Z13'Z3R3'R6'R__lutein_from_marigold_flowers_kale_and_human_plasma_ L2 - https://dx.doi.org/10.1021/jf980823w DB - PRIME DP - Unbound Medicine ER -