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Partial synthesis of serum carotenoids and their metabolites

100%

Khachik F.

Acta Biochimica Polonica

2012

tom 59

nr 1

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.

Partial and total synthesis of serum carotenoids and their metabolites

100%

Khachik F.

Acta Biologica Cracoviensia. Series Botanica. Supplement

2011

tom 53

nr 1

Total synthesis of an oxidation product of gamma-carotene, a pro-vitamin A food carotenoid

51%

Crawford K. , Khachik F. , Mazzola E.

Acta Biologica Cracoviensia. Series Botanica. Supplement

2011

tom 53

nr 1