β-Carotene autoxidation: oxygen copolymerization, non-vitamin A products and immunological activity

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DOIResolve DOI: http://doi.org/10.1139/cjc-2013-0494
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TypeArticle
Journal titleCanadian Journal of Chemistry
ISSN1480-3291
Volume92
Issue4
Pages305316; # of pages: 12
Subjectβ-carotene autoxidation; oxygen copolymer; non-vitamin A oxidation products; immune function; gene expression
AbstractCarotenoids are reported to have immunological effects independent of vitamin A activity. Although antioxidant activity has been suggested as a basis of action, the ability of carotenoids to autoxidize to numerous non-vitamin A products with immunological activity is an alternative yet to be fully explored. We have undertaken a systematic study of β-carotene autoxidation and tested the product mixture for immunological activity. Autoxidation proceeds predominantly by oxygen copolymerization, leading to a defined, reproducible product corresponding to net uptake of almost 8 molar equivalents of oxygen. The product, termed OxC-beta, empirical formula C40H60O15 versus C40H56 for β-carotene, contains more than 30% oxygen (w/w) and 85% β-carotene oxygen copolymers (w/w) as well as minor amounts of many C8−C18 norisoprenoid compounds. No vitamin A or higher molecular weight norisoprenoids are present. The predominance of polymeric products has not been reported previously. The polymer appears to be a less polymerized form of sporopollenin, a biopolymer found in exines of spores and pollen. Autoxidations of lycopene and canthaxanthin show a similar predominance of polymeric products. OxC-beta exhibits immunological activity in a PCR gene expression array, indicating that carotenoid oxidation produces non-vitamin A products with immunomodulatory potential.
Publication date
LanguageEnglish
AffiliationNational Research Council Canada; Aquatic and Crop Resource Development
Peer reviewedYes
NRC numberNRC-ACRD-55952
NPARC number21272466
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Record identifier738c1765-9794-46e2-a997-073ebbefe652
Record created2014-11-28
Record modified2016-05-09
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