Partial synthesis of serum carotenoids and their metabolites

• Autorzy: Khachik F.
• Języki publikacji: EN

Abstrakty

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.

• Wydawca: -
• Czasopismo: Acta Biochimica Polonica
• Rocznik: 2012
• Tom: 59
• Numer: 1
• Opis fizyczny: p.75-78,fig.,ref.

Twórcy

autor

Khachik F.

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

Bibliografia

• Ausich RL, Sanders DJ (1997) Process for the formation, isolation and purification of comestible xanthophyll crystals from plants. Kemin Industries, Inc. U.S. Patent, 5,648,564, July 17.
• Bernhard K, Giger A (1998) Process for the manufacturing of zeaxanthin from lutein. US Patent to Hoffmann-La Roche, 5,780,693.
• Bernstein PS et al. (2001) Identification and quantitation of carotenoids and their metabolites in the tissues of the human eye. Exp Eye Res 72: 215-223. 
• Bone RA, Landrum JT, Hime GW, Cains A, Zamor J (1993) Stereochemistry of the human macular carotenoids. Invest Ophthalmol Vis Sci 34: 2033-2040. 
• Khachik F, Beecher GR, Goli MB, Lusby WR (1991) Separation, identification, and quantification of carotenoids in fruits, vegetables and human plasma by high performance liquid chromatography. Pure Appl Chem 63: 71-80.
• Khachik F, Beecher GR, Goli MB, Lusby WR, Smith JC Jr. (1992) Separation and identification of carotenoids and their oxidation products in extracts of human plasma. Anal Chem 64: 2111-2122. 
• Khachik F (1995) Process for isolation, purification, and recrystallization of lutein from saponified marigolds oleoresin and uses thereof. The Catholic University of America. U.S. Patent, 5,382,714, January 17.
• Khachik F, Englert G, Beecher GR, Smith JC Jr. (1995) Isolation, structural elucidation, and partial synthesis of lutein dehydration products in extracts from human plasma. J Chromatogr B Biomed Appl 670: 219-233. 
• Khachik F, Spangler CJ, Smith JC Jr, Canfield LM, Pfander H, Steck A (1997a) Identification, quantification, and relative concentrations of carotenoids, and their metabolites in human milk and serum. Anal Chem 69: 1873-1881. 
• Khachik F, Bernstein P, Garland DL (1997b) Identification of lutein and zeaxanthin oxidation products in human and monkey retinas. Invest Ophthalmol Vis Sci 38: 1802-1811. 
• Khachik F, Moura FF, Zhao DY, Aebischer CP, Bernstein PS (2002) Transformations of selected carotenoids in plasma, liver, and ocular tissues of humans and in non-primate animal models. Invest Ophthalmol Vis Sci 43: 3383-3392. 
• Khachik F (2003) An efficient conversion of (3R,3'R,6'R)-lutein to (3R,3'S,6'R)-lutein (3'-epilutein) and (3R,3'R)-zeaxanthin. J Nat Prod 66: 67-72. 
• Khachik F (2006) Distribution and metabolism of dietary carotenoids in humans as a criterion for development of nutritional supplements. Pure Appl Chem 78: 1551-1557.
• Khachik F, Chang AN, Gana A, Mazzola E (2007) Partial synthesis of (3R,6'R)-α-cryptoxanthin and (3R)-β-cryptoxanthin from (3R,3'R,6'R)-lutein. J Nat Prod 70: 220-226. 
• Khachik F (2009) Process for synthesis of (3R,3'R)-zeaxanthin and (3R,3'S;meso)-zeaxanthin from (3R,3'R,6'R)-lutein via (3R)-3',4'-anhydrolutein. US Patent, 12/406,543.
• Khachik F, Chang AN (2009) Total synthesis of (3R,3'R,6'R)-lutein and its stereoisomers. J Org Chem 74: 3875-3885. 
• Kursanov DN, Parnes ZN, Loim NM (1974) Application of ionic hydrogenation to organic synthesis. Synthesis 633-651.
• Morris DL, Kritchevsky SB, Davis CE (1994) Serum carotenoids and coronary heart disease. JAMA 272: 1439-1441. 
• Seddon JM et al. (1994) Dietary carotenoids, vitamin A, C, and E, and advanced age-related macular degeneration. JAMA 272: 1413-1420. 
• Van Poppel G (1993) Carotenoids and Cancer: an update with emphasis on human intervention studies. Eur J Cancer 29A: 1335-1344. 

Uwagi

PL

Rekord w opracowaniu.