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A metal-free blue chromophore derived from plant pigments

Blue natural pigments are rare, especially among plants. However, flowering species that evolved to attract Hymenoptera pollinators are colored by blue anthocyanin-metal complexes. Plants lacking anthocyanins are pigmented by betalains but are unable to produce blue hues. By extending the π-system o...

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Detalles Bibliográficos
Autores principales: Freitas-Dörr, B. C., Machado, C. O., Pinheiro, A. C., Fernandes, A. B., Dörr, F. A., Pinto, E., Lopes-Ferreira, M., Abdellah, M., Sá, J., Russo, L. C., Forti, F. L., Gonçalves, L. C. P., Bastos, E. L.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Association for the Advancement of Science 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7124932/
https://www.ncbi.nlm.nih.gov/pubmed/32284978
http://dx.doi.org/10.1126/sciadv.aaz0421
Descripción
Sumario:Blue natural pigments are rare, especially among plants. However, flowering species that evolved to attract Hymenoptera pollinators are colored by blue anthocyanin-metal complexes. Plants lacking anthocyanins are pigmented by betalains but are unable to produce blue hues. By extending the π-system of betalains, we designed a photostable and metal-free blue dye named BeetBlue that did not show toxicity to human hepatic and retinal pigment epithelial cells and does not affect zebrafish embryonal development. This chiral dye can be conveniently synthesized from betalamic acid obtained from hydrolyzed red beetroot juice or by enzymatic oxidation of l-dopa. BeetBlue is blue in the solid form and in solution of acidified polar molecular solvents, including water. Its capacity to dye natural matrices makes BeetBlue the prototype of a new class of low-cost bioinspired chromophores suitable for a myriad of applications requiring a blue hue.