Investigating isomer specific photoprotection in a model plant sunscreen

Sinapate esters are used throughout the plant kingdom, for example in photoprotection from ultraviolet radiation. Sinapate esters are naturally produced in their E-isomeric form; however, upon exposure to ultraviolet radiation, photoisomerization drives Z-isomer formation. To elucidate the photoprot...

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Published inChemical communications (Cambridge, England) Vol. 54; no. 8; pp. 936 - 939
Main Authors Horbury, M D, Flourat, A L, Greenough, S E, Allais, F, Stavros, V G
Format Journal Article
LanguageEnglish
Published England Royal Society of Chemistry 2018
Subjects
Biosynthesis
Chemical Sciences
Esters
or physical chemistry
Photochemistry
Theoretical and
Ultraviolet radiation
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Summary:Sinapate esters are used throughout the plant kingdom, for example in photoprotection from ultraviolet radiation. Sinapate esters are naturally produced in their E-isomeric form; however, upon exposure to ultraviolet radiation, photoisomerization drives Z-isomer formation. To elucidate the photoprotection capacity of E vs. Z forms of sinapate esters, we explore the photochemistry of the model system, Z-ethyl sinapate. Following a novel Z-ethyl sinapate synthesis, we demonstrate that photoprotection is isomer independent. This suggests that, regarding photoprotection, there were no evolutionary pressures for biosynthesis of either isomer.
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ISSN:1359-7345
1364-548X
DOI:10.1039/c7cc09061g