Organic synthesis of new putative lycopene metabolites and preliminary investigation of their cell-signaling effects

Eric Reynaud; Gamze Aydemir; Ralph Rühl; Olivier Dangles; Catherine Caris-Veyrat

doi:10.1021/jf104092e

Organic synthesis of new putative lycopene metabolites and preliminary investigation of their cell-signaling effects

Eric Reynaud, Gamze Aydemir, Ralph Rühl, Olivier Dangles, Catherine Caris-Veyrat^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

36 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	1457-1463
Number of pages	7
Journal	Journal of Agricultural and Food Chemistry
Volume	59
Issue number	4
DOIs	https://doi.org/10.1021/jf104092e
State	Published - 23 Feb 2011
Externally published	Yes

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abstract = "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.",

author = "Eric Reynaud and Gamze Aydemir and Ralph R{\"u}hl and Olivier Dangles and Catherine Caris-Veyrat",

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T1 - Organic synthesis of new putative lycopene metabolites and preliminary investigation of their cell-signaling effects

AU - Reynaud, Eric

AU - Aydemir, Gamze

AU - Rühl, Ralph

AU - Dangles, Olivier

AU - Caris-Veyrat, Catherine

PY - 2011/2/23

Y1 - 2011/2/23

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/79951731062

U2 - 10.1021/jf104092e

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EP - 1463

JO - Journal of Agricultural and Food Chemistry

JF - Journal of Agricultural and Food Chemistry

IS - 4

ER -

Organic synthesis of new putative lycopene metabolites and preliminary investigation of their cell-signaling effects

Abstract

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