Organic synthesis of new putative lycopene metabolites and preliminary investigation of their cell-signaling effects.
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.
Safety and Quality of Plant Products, INRA , UMR 408, F-84000 Avignon, France.
Eric
E
Reynaud
Gamze
G
Aydemir
Ralph
R
Rühl
Olivier
O
Dangles
Catherine
C
Caris-Veyrat
D000818:Animals; D002338:Carotenoids / Q000378:metabolism*; D049308:Dioxygenases; D044943:Fatty Acid Desaturases; D005231:Fatty Acids, Unsaturated / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D005638:Fruit / Q000737:chemistry; D015870:Gene Expression / Q000187:drug effects; D000077276:Lycopene; D018551:Solanum lycopersicum / Q000737:chemistry; D008297:Male; D051379:Mice; D008810:Mice, Inbred C57BL; D010105:Oxygenases / Q000235:genetics; D015398:Signal Transduction; D013237:Stereoisomerism; D013737:Testis / Q000201:enzymology
C557871:14'-apolycopen-14'-oic acid; C557870:4,9,13,17,21-pentamethyldocosa-2,4,6,8,10,12,14,16,20-nonaenoic Acid; D005231:Fatty Acids, Unsaturated; D002338:Carotenoids; D010105:Oxygenases; C093259:beta-carotene ketolase; D049308:Dioxygenases; D044943:Fatty Acid Desaturases; C506534:BCO2 protein, human; D000077276:Lycopene