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Modifying the chromophoric ring of betalamic acid in plant pigments. Synthesis and characterization of methylated betalains

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dc.contributor.authorMartínez-Rodríguez, Pedro
dc.contributor.authorContreras-Llano, Luis Eduardo
dc.contributor.authorPagán-López, Diego José
dc.contributor.authorGuerrero-Rubio, María Alejandra
dc.contributor.authorLozada-Ramírez, José Daniel
dc.contributor.authorHernández-García, Samanta
dc.contributor.authorGandía Herrero, Fernando
dc.contributor.departmentBioquímica y Biología Molecular "A"es
dc.date.accessioned2025-05-28T07:16:28Z
dc.date.available2025-05-28T07:16:28Z
dc.date.issued2025-05-23
dc.description© 2025, The Authors. This manuscript version is made available under the CC-BY-NC 4.0 license http://creativecommons.org/licenses/by-nc/4.0/. This document is the Published version of a Published Work that appeared in final form in Bioorganic Chemistry. To access the final edited and published work see https://doi.org/10.1016/j.bioorg.2025.108623es
dc.description.abstractThe recent discovery of decarboxylated betalains, derived from dopamine, in nature has expanded the number of chemical modifications possible in these plant pigments. Alternative starting materials in biochemical rocesses can yield novel molecules with modifications in the betalamic ring. For the first time, a functional group has been incorporated into the betalamic acid structure of betalains, thus creating a novel family of methylated pigments. A synthetic pathway starting from α-methyl-DOPA yields 6-methyl-betalamic acid. The process is enzymatic and kinetic characterization reveals that the formation of 6-methyl-betalamic acid is favored over the formation of 6- methyl-dopaxanthin, as a further condensation reaction can be hindered. Starting from the methylated betalamic acid, a novel family of methylated betalains has been biotechnologically produced comprising ten yellow and violet molecules. The novel compounds were characterized by using HPLC-ESI-Q-TOF-MS, spectrophotometry, and spectrofluorometry. Potential antioxidant capacity was measured using the ORAC assay, demonstrating the molecules’ effectiveness against peroxyl radicals, with indoline-6-methyl-betacyanin identified as the most antioxidant. This study shows the venue for the chemical modification of the betalamic ring in pigments and thus represents the beginning of the era of betalain core chemistry. This opens new fields for future research to explore novel structures and their potential bioactive effects.es
dc.formatapplication/pdfes
dc.format.extent13es
dc.identifier.citationBioorganic Chemistry 162 (2025) 108623
dc.identifier.doihttps://doi.org/10.1016/j.bioorg.2025.108623
dc.identifier.issnPrint: 0045-2068
dc.identifier.issnElectronic: 1090-2120
dc.identifier.urihttp://hdl.handle.net/10201/155156
dc.languageenges
dc.publisherElsevier
dc.relationThis work was supported by the Spanish Ministry of Science and Innovation, project PID2021-122896NB-I00 (MCIN/AEI/10.13039 /501100011033/FEDER, UE). P. M.-R. holds a contract financed by Fundación Séneca (Spain) (21587/FPI/21).es
dc.relation.publisherversionhttps://www.sciencedirect.com/science/article/pii/S0045206825005036?via%3Dihub
dc.rightsinfo:eu-repo/semantics/openAccesses
dc.rightsAtribución-NoComercial 4.0 Internacional*
dc.rights.urihttp://creativecommons.org/licenses/by-nc/4.0/*
dc.subjectα-Methyl-DOPAes
dc.subjectBetalamic ringes
dc.subjectBetalain chemistryes
dc.subjectMethylated pigmentes
dc.subject.otherCDU::5 - Ciencias puras y naturales::57 - Biología::577 - Bioquímica. Biología molecular. Biofísicaes
dc.titleModifying the chromophoric ring of betalamic acid in plant pigments. Synthesis and characterization of methylated betalainses
dc.typeinfo:eu-repo/semantics/articlees
dspace.entity.typePublicationes
relation.isAuthorOfPublicationdb7a1a52-fec7-48eb-91e0-abe5e715b483
relation.isAuthorOfPublication.latestForDiscoverydb7a1a52-fec7-48eb-91e0-abe5e715b483
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