Partial synthesis of serum carotenoids and their metabolites

• Authors: Frederick Khachik
• Languages of publication: EN

Abstracts

EN

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.

Keywords

EN

dietary hydroxycarotenoids; β-cryptoxanthin; carotenoid metabolites; α-cryptoxanthin; allylic deoxygenation; anhydroluteins; hydroboration; ionic hydrogenation

• Publisher: Polish Biochemical Society
• Journal: Acta Biochimica Polonica
• Year: 2012
• Volume: 59
• Issue: 1
• Pages: 75-78

Dates

published

2012

received

2011-10-17

accepted

2012-03-01

(unknown)

2012-03-17

Contributors

author

Frederick Khachik

• Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland, USA

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