Photophysical properties of betaxanthins: Vulgaxanthin I in aqueous and alcoholic solutions

Wendel, Monika; Szot, Dominika; Starzak, Karolina; Tuwalska, Dorota; Gapiński, Jacek; Naskręcki, Ryszard; Prukała, Dorota; Sikorski, Marek; Wybraniec, Sławomir; Burdziński, Gotard

doi:10.1016/j.jlumin.2015.06.030

Cited by 24 publications

(31 citation statements)

References 48 publications

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“…Thus, from the early work with these pigments [32,33] the absorbance spectra of different species and the limited effect of M A N U S C R I P T A C C E P T E D ACCEPTED MANUSCRIPT 16 various substituents on them have been characterized [34]. However, despite numerous studies on betalains, the existence of betaxanthins fluorescence has only recently been described and investigated [13,35,36]. Therefore, after synthesis of BSA-betaxanthin our next objective was to characterize the derivatized protein and to verify if it maintained the characteristics of betaxanthins, in particular, their fluorescent properties.…”

Section: Fluorescent Properties Of Betalamic Acid Derivativesmentioning

confidence: 99%

Fluorescent bioinspired protein labeling with betalamic acid. Derivatization and characterization of novel protein-betaxanthins

et al. 2016

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Section: Fluorescent Properties Of Betalamic Acid Derivativesmentioning

confidence: 99%

Fluorescent bioinspired protein labeling with betalamic acid. Derivatization and characterization of novel protein-betaxanthins

et al. 2016

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“…In betalains it has been demonstrated that this value is proportional to the viscosity of the solvent used (Table 1). Thus, the analysis in water and methanol gives lower values than in ethylene glycol [37,[39][40][41]. This response has also been shown for betaxanthin molecules present in gelificating media, where fluorescence intensity increases with the time course of the process [42].…”

Section: Photophysicsmentioning

confidence: 61%

“…Betanin 0.0007 0.0013 0.0047 [37] Indicaxanthin 0.0053 0.0081 0.033 [39] Miraxanthin V 0.003 0.0047 0.015 [41] Vulgaxanthin I 0.0073 0.011 0.039 [40] Miraxanthin I 0.0084 -- [34] show that an increase in the viscosity of the medium makes the convection of the acquired energy difficult, favoring the path of the fluorescence. The presence of aromatic rings linked to the electron resonance system characteristic of betalamic acid implies a marked decrease in the fluorescence intensity.…”

Section: Photophysicsmentioning

confidence: 99%

“…Only the fully planar aniline-derived betalain presents fluorescence intensity comparable with betaxanthins. The effect of the medium was also studied by taking indicaxanthin, vulgaxanthin I, and miraxanthin V as model betaxanthins, describing how higher viscosity in the solutions increased the fluorescence quantum yields and the lifetimes of the excited states [39][40][41].…”

Section: Photophysicsmentioning

confidence: 99%

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Light Emission in Betalains: From Fluorescent Flowers to Biotechnological Applications

Guerrero-Rubio

Escribano

García-Carmona

2020

Trends in Plant Science

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The discovery of visible fluorescence in the plant pigments betalains revealed the existence of fluorescent patterns in flowers of plants of the order Caryophyllales, where betalains substitute anthocyanins. The serendipitous initial discovery led to a systemized characterization of the role of different substructures on the photophysical phenomenon. Strong fluorescence is general to all members of the family of betaxanthins linked to the structural property that the betalamic acid moiety is connected to an amine group. This property has led to bioinspired tailor-made probes and to the development of novel biotechnological applications in screening techniques or microscopy labeling. Here, we comprehensively review the photophysics, photochemistry, and photobiology of betalain fluorescence and describe all current applications. BetalainsBetalains are nitrogenous plant pigments that are characteristic for plants belonging to the order Caryophyllales. These pigments are divided into the yellow betaxanthins and the violet betacyanins [1]. The presence of both types of pigments is required for the orange and red colors that coexist in nature with the pure yellow and violet colors. Betalains substitute anthocyanins and play their roles in the colored tissues of most plant families of the Caryophyllales. Both families of pigments are watersoluble and mutually exclusive [2,3]. Numerous studies were performed on the color properties of betalains since they were described as a novel family of pigments, different to 'nitrogenous anthocyanins' [4,5]. However, it was not until 2005 that their natural fluorescence was discovered [6]. In addition, it was demonstrated that under physiological conditions, light emission was exhibited in the plant tissues that contain them, including flowers [7,8].Among the Caryophyllales plants, red beet roots (Beta vulgaris) and the fruits of cacti belonging to the genus Opuntia are the best known sources of betalains, with betanin and indicaxanthin being, respectively, their main pigments [9,10]. Current research has described the betalain content of novel sources, such as the tubers from Ullucus tuberosus [11] or the betalain-containing berries of Rivina humilis [12]. Also, the multiple shades of quinoa grains (Chenopodium quinoa) have recently been reported to be based on betacyanins and betaxanthins [13]. In addition, betalains have in recent years been shown to have promising bioactive properties. Early investigations revealed a strong free radical scavenging capacity of betalains purified from beet root [14]. Subsequent research revealed the existence of an intrinsic activity, present in all betalains, that is modulated by structural factors [15,16]. Furthermore, studies with different human cancer cell lines have demonstrated the potential of betalains in the chemoprevention of cancer [17,18]. In vivo experiments have shown that very low concentrations of dietary pigments inhibit the formation of tumors in mice [19,20] and extend the lifespan of the model animal Caenorhabditis elegans [21...

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“…Embora a largura do pulso a meia altura seja de ca.6 ps, observa-se no intervalo < 1 ps a mudança do máximo desta transição, bem como da emissão estimulada (SE, banda negativa próxima a 620 nm), para comprimentos de onda mais longos, fato que pode estar relacionado a solvatação da espécie localmente excitada.As duas bandas negativas, uma com máximo em 578 nm e outra em 634 nm, referem-se à recomposição do estado fundamental (branqueamento, bleaching) e à emissão estimulada (SE), respectivamente. Este perfil observado é similar aos dados da literatura para as betalaínas Bn, BtP, vulgaxantina-I e miraxantina-V 36,37,39,40. Todos os processos observados tem tempo de vida próximo a 14 ps, valor calculado através do ajuste não linear da variação da absorção em função do tempo com função monoexponencial (anexo 7.7).…”

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BeetBlue: semissíntese e propriedades espectroscópicas de um corante polimetínico quiral bioinspirado

Freitas-Dörr¹

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AgradecimentosAo meu orientador, Prof. Dr. Erick L. Bastos, pela confiança, pelas oportunidades, pelas conversas e discussões e pela paciência durante essa jornada.À Deus e aos meus guias espirituais por estarem presentes em todos os momentos da minha vida me protegendo, por serem a luz dos meus caminhos e o refúgio nos bons e maus momentos.Ao meu marido Felipe pelo apoio incondicional, por ser a calmaria no meu temporal e a razão no meu turbilhão de emoções. Por ser meu companheiro, meu melhor amigo, por me completar e fazer a minha vida muito mais feliz. Você foi essencial para esta conquista.Aos meus pais, Marcos e Mara, pelo amor incondicional, pela torcida e por sempre me acompanharem de perto e me apoiarem em todas as minhas loucuras. Obrigada por serem minha base e por me ensinarem a valorizar o que realmente importa nessa vida. Amo vocês! Ao meu irmão Vinicius por tornar minha vida mais doce, pelas maluquices e por ser super companheiro. Tenho muito orgulho de ser sua irmã. Te amo! À Jaque, irmã que a vida me deu, por todo incentivo, apoio, carinho e, principalmente, pela paciência e compreensão nas minhas ausências. À toda minha família pelo apoio e pela torcida. À família Contente Silva. Thá e Di pelos conselhos, por acreditarem e confiarem em mim e por todos os puxões de orelha necessários. E Be e Theo por encherem a minha vida de alegria e amor. Ao time BastosLab e aos colegas do 461 pela ajuda e pelas discussões que contribuíram muito para a execução deste trabalho. ii Aos amigos que o Doutorado me deu: Amanda, Arthur, Ana Clara, Karina e Renan. Muito obrigada por toda ajuda, pelo apoio, pela companhia diária, pelas comilanças e por tornarem tudo mais leve. Aos técnicos do IQ, principalmente ao Joca e à Helena pela sempre disponibilidade em ajudar e pelas conversas. À Clélia e ao Walter por me apresentarem o mundo acadêmico, pelos conselhos, pelo carinho e pelo cuidado. Aos técnicos da Central Analítica, Janaína, Cristiane, Vânia, Giovana, Adriana e Wilton pela ajuda essencial para o desenvolvimento deste trabalho. Ao Prof. Ernani por ter me iniciado na academia e por ter deixado a porta do seu laboratório sempre aberta para mim, seja para experimentos ou para conversas. Obrigada Felipe pelas análises de espectrometria de massas. Ao Prof. Jacinto por me receber tão bem em seu laboratório e por todos os ensinamentos. Aos colegas de Uppsala pela acolhida e ao Mohamed e Daniel pela ajuda nos experimentos. Aos Profs. Willi, Maurício, Frank, Omar, Cassius, Thiago Correra e Thiago Paixão e seus alunos, pelas explicações, ensinamentos e pelo uso dos equipamentos em seus laboratórios. À FAPESP pela bolsa concedida (2014/10563-5) e CNPq e Capes pelo financiamento dos projetos iii "Experimentei algo que depois, ao longo de minha vida, se repetiu frequentemente: a alegria do novo" Elena Ferrante em "A amiga genial" iv v Resumo FREITAS-DÖRR, B. C. BeetBlue: semissíntese e propriedades espectroscópicas de um corante polimetínico quiral bioinspirado 2018. 158f Tese (Doutorado) -Instituto de Química, Universidade d...

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Photophysical properties of betaxanthins: Vulgaxanthin I in aqueous and alcoholic solutions

Cited by 24 publications

References 48 publications

Fluorescent bioinspired protein labeling with betalamic acid. Derivatization and characterization of novel protein-betaxanthins

Fluorescent bioinspired protein labeling with betalamic acid. Derivatization and characterization of novel protein-betaxanthins

Light Emission in Betalains: From Fluorescent Flowers to Biotechnological Applications

BeetBlue: semissíntese e propriedades espectroscópicas de um corante polimetínico quiral bioinspirado

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Photophysical properties of betaxanthins: Vulgaxanthin I in aqueous and alcoholic solutions

Cited by 24 publications

References 48 publications

Fluorescent bioinspired protein labeling with betalamic acid. Derivatization and characterization of novel protein-betaxanthins

Fluorescent bioinspired protein labeling with betalamic acid. Derivatization and characterization of novel protein-betaxanthins

Light Emission in Betalains: From Fluorescent Flowers to Biotechnological Applications

BeetBlue: semissí­ntese e propriedades espectroscópicas de um corante polimetí­nico quiral bioinspirado

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BeetBlue: semissíntese e propriedades espectroscópicas de um corante polimetínico quiral bioinspirado