Journal
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
Volume 59, Issue 4, Pages 1457-1463Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jf104092e
Keywords
Apo-lycopenoic acids; organic synthesis; lycopene; metabolite; beta,beta-carotene oxygenase; gene expression
Funding
- European Community [016213]
- TAMOP [4.2.1./B-09/1/KONV-2010-0007]
- European Social Fund
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Tomato is the main dietary source of lycopene, a carotenoid that is known to have protective effects on health and whose metabolites could also be involved in bioactivity. Herein we present the first organic synthesis of two potentially bioactive lycopene metabolites, namely, 10'-apolycopen-10'-oic acid (6) and 14'-apolycopen-14'-oic acid (13), which were obtained in their (all-E) stereoisomeric forms using Wittig and Horner-Wadsworth-Emmons type coupling reactions. Both molecules are shown to up-regulate the carotenoid asymmetric cleavage enzyme BCO2 while having no effect on BCO1. expression.
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