Evidence of cis-trans isomerization of 9-cis-β-carotene during absorption in humans

American Journal of Clinical Nutrition

Volumn 64, Issue 2, 1996, Pages 177-183

  You, Cha Sook ^a   Parker, Robert S ^a   Goodman, Keith J ^a   Swanson, Joy E ^a   Corso, Thomas N ^a  

^a Department of Obstetrics Gynecology   (United States)

Author keywords

9 cis Carotene; all trans carotene; cis trans isomerization; human metabolism; isotope ratio mass spectrometry; stable isotope; vitamin A

Indexed keywords

9 CIS BETA CAROTENE; ALITRETINOIN; BETA CAROTENE; RETINOID; RETINOL; UNCLASSIFIED DRUG;

ADULT; ARTICLE; CIS TRANS ISOMERISM; CLINICAL PROTOCOL; CLINICAL TRIAL; DOSE RESPONSE; DRUG ABSORPTION; FEMALE; HUMAN; HUMAN EXPERIMENT; INTESTINE ABSORPTION; INTESTINE MUCOSA; MALE; NORMAL HUMAN; NUTRITIONAL SUPPORT;

EID: 0029998371     PISSN: 00029165     EISSN: None     Source Type: Journal    
DOI: 10.1093/ajcn/64.2.177     Document Type: Article

References (25)

1. Nagao A, Olson JA. Enzymatic formation of 9-cis, 13-cis, and all-trans retinals from isomers of β-carotene. FASEB J 1994;8:968-73.
2. Wang X-D, Krinsky NI, Benotti PN, Russell RM. Biosynthesis of 9-cis-retinoic acid from 9-cis-β-carotene in human intestinal mucosa in vitro. Arch Biochem Biophys 1994;313:150-5.
3. Levin AA, Sturzenbecker LJ, Kazmer S, et al. 9-cis retinoic acid stereoisomer binds and activates the nuclear receptor RXRα. Nature 1992;355:359-61.
4. Heyman RA, Mangelsdorf DJ, Dyck JA, et al. 9-cis retinoic acid is a high affinity ligand for the retinoid X receptor. Cell 1992;68:397-406.
5. Chandler LA, Schwartz. HPLC separation of cis-trans carotene isomers in fresh and processed fruits and vegetables. J Food Sci 1987;52:669-72.
6. Panalaks T, Murray TK. The effect of processing on the content of carotene isomers in vegetables and peaches. J Inst Can Technol Aliment 1970;3:145-51.
7. Sweeney JP, Marsh, AC. Effect of processing on provitamin A in vegetables. J Am Diet Assoc 1971;59:238-43.
8. Jensen CD, Howes TW, Spiller GA, Pattison TS, Whittam JH, Scala J. Observations on the effects of ingesting cis- and trans-β-carotene isomers on human serum concentrations. Nutr Rep Int 1987;35:413-22.
9. Stahl W, Schwarz W, Sies H. Human serum concentrations of all-trans β- and α-carotene but not 9-cis β-carotene increase upon ingestion of a natural isomer mixture obtained from Dunaliella salina (Betatene). J Nutr 1993;123:847-51.
10. Stahl W, Schwarz W, Larr J, Sies H. all-trans β-Carotene preferentially accumulates in human chylomicrons and very low density lipoproteins compared with the 9-cis geometrical isomer. J Nutr 1995;125:2128-33.
11. White WS, Peck KM, Ulman EA, Erdman JM Jr. The ferrets as a model for evaluation of the bioavailabilities of all-trans-β-carotene and its isomers. J Nutr 1993;123:1129-39.
12. Ben-Amotz A, Mokady S, Edelstein S, Avron M. Bioavailability of a natural isomer mixture as compared with synthetic all-trans-β-carotene in rats and chicks. J Nutr 1989;119:1013-9.
13. Mokady S, Avron M, Ben-Amotz A. Accumulation in chick livers of 9-cis versus all-trans β-carotene. J Nutr 1990;120:889-92.
14. Shlomai P, Ben-Amotz A, Margalith P, Mokady S. Utilization of a natural β-carotene stereoisomer mixture from the fungus Phycomyces blakesleeanus as a source of vitamin A and β-carotene in rats diet. J Nutr Biochem 1992;3:415-20.
15. 13C-β-carotene and high precision isotope ratio mass spectrometry. Ann N Y Acad Sci 1993;691:86-95.
16. Brenna JT. High-precision gas isotope ratio mass spectrometry: recent advances in instrumentation and biomedical applications. Accounts Chem Res 1994;27:340-6.
17. 13C]-labeled precursors. Anal Chem 1992;64:1088-95.
18. Thurnham DI, Smith E, Flora PS. Concurrent liquid-chromatographic assay of retinol, α-tocopherol, β-carotene, α-carotene, lycopene, and β-crytoxanthin in plasma, with tocopherol acetate as internal standard. Clin Chem 1988;34:377-81.
19. Bridges CD. High-performance liquid chromatography of retinoic isomers: an overview. Methods Enzymol 1990;189:60-9.
20. Mood AM, Graybill FA, Boer DC. Introduction to the theory of statistics. 3rd ed. New York: McGraw-Hill, 1974.
21. van Vliet T, Schreurs WHP, van den Berg H. Intestinal β-carotene absorption and cleavage in men: response of β-carotene and retinyl esters in the triglyceride-rich lipoprotein fraction after a single oral dose of β-carotene. Am J Clin Nutr 1995;62:110-6.
22. Doering WE, Sotiriou-Leventis C, Roth WR. Thermal interconversions among 15-cis, 13-cis, and all-trans-β-carotene: kinetics, Arrhenius parameters, thermochemistry, and potential relevance to anticarcinogenicity of all-trans-β-carotene. J Am Chem Soc 1995;117:2747-57.
23. Gaziano JM, Johnson EJ, Russell RM, et al. Discrimination in absorption or transport of β-carotene isomers after oral supplementation with either all-trans- or 9-cis-β-carotene. Am J Clin Nutr 1995;61:1248-52.
24. Zechmeister L. Cis-trans isomeric carotenoids vitamins A and arylpolyenes. New York: Academic Press Inc, Publishers, 1962.
25. Weiser H, Riss G, Biesalski HK. Uptake and metabolism of β-carotene isomers in rats. Ann N Y Acad Sci 1993;691:223-5.