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Partial synthesis of serum carotenoids and their metabolites.
Acta Biochim Pol. 2012; 59(1):75-8.AB

Abstract

Human serum and tissues contain in excess of 12 dietary carotenoids and several metabolites that originate from consumption of fruits and vegetables. Among these are hydroxycarotenoids: (3R,3'R,6'R)-lutein (1), (3R,3'R)-zeaxanthin (2), (3R,6'R)-α-cryptoxanthin (3), and (3R)-β-cryptoxanthin (4). In addition, several dehydration products of 1 have also been identified in human serum, these are: (3R,6'R)-3-hydroxy-3',4'-didehydro-β,γ-carotene (5), (3R,6'R)-3-hydroxy-2',3'-didehydro-β,ε-carotene (6), and (3R)-3-hydroxy-3',4'-didehydro-β,β-carotene (7). Several metabolites of 1 and/or 2, namely, (3R,3'S,6'R)-lutein (3'-epilutein, 8) and (3R,3'S;meso)-zeaxanthin (9) have also been characterized in human serum and ocular tissues. Semi-synthetic processes have been developed that separately transform commercially available 1 into 4 via 7 as well as 1 into 8. While 8 is converted into 2 by base-catalyzed isomerization, 7 is transformed into 2 and its (3R,3'S;meso)-stereoisomer (9) by regioselective hydroboration.

Authors+Show Affiliations

Department of Chemistry and Biochemistry, University of Maryland, College Park, USA. Khachik@umd.edu

Pub Type(s)

Journal Article

Language

eng

PubMed ID

22428147

Citation

Khachik, Frederick. "Partial Synthesis of Serum Carotenoids and Their Metabolites." Acta Biochimica Polonica, vol. 59, no. 1, 2012, pp. 75-8.
Khachik F. Partial synthesis of serum carotenoids and their metabolites. Acta Biochim Pol. 2012;59(1):75-8.
Khachik, F. (2012). Partial synthesis of serum carotenoids and their metabolites. Acta Biochimica Polonica, 59(1), 75-8.
Khachik F. Partial Synthesis of Serum Carotenoids and Their Metabolites. Acta Biochim Pol. 2012;59(1):75-8. PubMed PMID: 22428147.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Partial synthesis of serum carotenoids and their metabolites. A1 - Khachik,Frederick, Y1 - 2012/03/17/ PY - 2011/10/17/received PY - 2012/03/01/accepted PY - 2012/3/20/entrez PY - 2012/3/20/pubmed PY - 2012/7/24/medline SP - 75 EP - 8 JF - Acta biochimica Polonica JO - Acta Biochim. Pol. VL - 59 IS - 1 N2 - Human serum and tissues contain in excess of 12 dietary carotenoids and several metabolites that originate from consumption of fruits and vegetables. Among these are hydroxycarotenoids: (3R,3'R,6'R)-lutein (1), (3R,3'R)-zeaxanthin (2), (3R,6'R)-α-cryptoxanthin (3), and (3R)-β-cryptoxanthin (4). In addition, several dehydration products of 1 have also been identified in human serum, these are: (3R,6'R)-3-hydroxy-3',4'-didehydro-β,γ-carotene (5), (3R,6'R)-3-hydroxy-2',3'-didehydro-β,ε-carotene (6), and (3R)-3-hydroxy-3',4'-didehydro-β,β-carotene (7). Several metabolites of 1 and/or 2, namely, (3R,3'S,6'R)-lutein (3'-epilutein, 8) and (3R,3'S;meso)-zeaxanthin (9) have also been characterized in human serum and ocular tissues. Semi-synthetic processes have been developed that separately transform commercially available 1 into 4 via 7 as well as 1 into 8. While 8 is converted into 2 by base-catalyzed isomerization, 7 is transformed into 2 and its (3R,3'S;meso)-stereoisomer (9) by regioselective hydroboration. SN - 1734-154X UR - https://www.unboundmedicine.com/medline/citation/22428147/Partial_synthesis_of_serum_carotenoids_and_their_metabolites_ L2 - http://www.actabp.pl/pdf/1_2012/75.pdf DB - PRIME DP - Unbound Medicine ER -