Towards symmetry driven and nature inspired UV filter design
Open accessAbstract
In plants, sinapate esters offer crucial protection from the deleterious effects of ultraviolet radiation exposure. These esters are a promising foundation for designing UV filters, particularly for the UVA region (400 - 315 nm), where adequate photoprotection is currently lacking. Whilst sinapate esters are highly photostable due to a cis-trans (and vice versa) photoisomerization, the cis-isomer can display increased genotoxicity; an alarming concern for current cinnamate ester-based human sunscreens. To eliminate this potentiality, here we synthesize a sinapate ester with equivalent cis- and trans-isomers. We investigate its photostability through innovative ultrafast spectroscopy on a skin mimic, thus modelling the as close to true environment of sunscreen formulas. These studies are complemented by assessing endocrine disruption activity and antioxidant potential. We contest, from our results, that symmetrically functionalized sinapate esters may show exceptional promise as nature-inspired UV filters in next generation sunscreen formulations.
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Sinapoyl-L-malate (142) is a sinapoyl ester widely described for its UV protection in plants.
“Sinapoyl-L-malate (142) is a sinapoyl ester widely described for its UV protection in plants [140].”
From UV Filters: Challenges and Prospects (2022) · cites this paper as [140]
The Introduction says naturally occurring sinapate esters provide UV photoprotection, supporting the claim at the class level. Our copy does not identify sinapoyl-L-malate specifically or establish that its protective role is widely described; the paper focuses on diethyl sinapate. (LLM, conf=0.84)
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Biobased UV Filters and Antioxidants
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- Authors
- Horbury, M. D., Holt, E. L., Mouterde, L. M. M., Balaguer, P., Cebrián, J., Blasco, L., Allais, F., & Stavros, V. G.
- Affiliations
- University of Leeds (GB)
- University of Warwick (GB)
- AgroParisTech (FR)
- Inserm (FR)
- Corresponding author
- Horbury, Michael D.
- Stavros, Vasilios G.
- ORCID
- Venue
- Nature Communications
- Published
- 2019-10-18
- Volume
- 10
- Issue
- 1
- Pages
- 4748-4748
- ISSN
- 2041-1723 (ISSN-L)
- PMC
- PMC6802189
- OpenAlex
- W2981194347
- Cited by
- 73
- References
- 33
- Citations by year
- 2026: 6 · 2025: 6 · 2024: 4 · 2023: 13 · 2022: 15 · 2021: 12 · 2020: 17
- FWCI
- 11.10
- Type
- journal article
- Language
- en
- Open access
- gold
- doi.org
- Locations
- Nature Communications (publishedVersion, cc-by)
- PubMed Central (publishedVersion, cc-by)
- PubMed (publishedVersion)
- White Rose Research Online (University of Leeds, The University of Sheffield, University of York) (acceptedVersion)
- Warwick Research Archive Portal (University of Warwick) (acceptedVersion)
- RePEc: Research Papers in Economics (submittedVersion, cc-by)
- HAL (submittedVersion, other-oa)
- DOAJ (DOAJ: Directory of Open Access Journals) (submittedVersion, cc-by-sa)
- DOAJ (DOAJ: Directory of Open Access Journals) (submittedVersion)
- Funders
- Conseil départemental de la Marne
- Leverhulme Trust (RPG-2016-055, RPG-2016)
- Royal Society
- University of Warwick
- Agence Nationale de la Recherche (ANR-17-CE07-0046, ANR-17)
- Engineering and Physical Sciences Research Council (L015307/1, 1793141, L015307, EP/J007153, EP/L015307/1, EP/N010825/1)
- Topics
- Health Sciences › Medicine › Dermatology › Skin Protection and Aging
- Physical Sciences › Materials Science › Materials Chemistry › Photochromic and Fluorescence Chemistry
- Physical Sciences › Chemistry › Physical and Theoretical Chemistry › Photochemistry and Electron Transfer Studies
- Keywords
- UV filters, sunscreen formulation, cis-trans photoisomerization, photostability, cinnamic acid esters, genotoxicity, ultrafast spectroscopy, endocrine disruption, antioxidant activity, nature-inspired materials, UVA protection
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