Betalains

Zrÿd, Jean-Pierre; Christinet, Laurent

doi:10.1002/9781119312994.apr0136

Cited by 5 publications

(2 citation statements)

References 102 publications

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“…In an alternative pathway, betalamic acid can also be susceptible to hydrolysis, resulting in its biosynthetic precursor, 4,5‐ seco ‐DOPA (Scheme 3c) . Unfortunately, the protonation state of HBt cannot be easily determined by mass spectrometry.…”

Section: Discussionmentioning

confidence: 99%

Revisiting the Mechanism of Hydrolysis of Betanin

Esteves

Pinheiro

Pioli

et al. 2018

Photochem & Photobiology

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Betanin (betanidin 5-O-β-D-glucoside) is a water-soluble plant pigment used as a color additive in food, drugs and cosmetic products. Despite its sensitivity to light and heat, betanin maintains appreciable tinctorial strength in low acidic and neutral conditions, where the color of other plant pigments, such as anthocyanins, quickly fades. However, betanin is an iminium natural product that experiences acid- and base-catalyzed hydrolysis to form the fairly stable betalamic acid and cyclo-DOPA-5-O-β-D-glucoside. Here, we show that the decomposition of betanin in aqueous phosphate solution pH 2-11 is subject to general base catalysis by hydrogen phosphate ion and intramolecular general acid and base catalysis, providing new insights on the mechanism of betanin hydrolysis. UV/Vis absorption spectrophotometry, H NMR spectroscopy and mass spectrometry were used to investigate product formation. Furthermore, theoretical calculations support the hypothesis that the nitrogen atom of the tetrahydropyridine ring of betanin is doubly protonated, as observed for structurally simpler amino dicarboxylic acids. Our results contribute to the study of betanin and other pigments belonging to the class of betalains and to deepen the knowledge on the chemical properties of imino acids as well as on iminium-catalyzed modifications of carbonyl compounds in water.

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Section: Discussionmentioning

confidence: 99%

Revisiting the Mechanism of Hydrolysis of Betanin

Esteves

Pinheiro

Pioli

et al. 2018

Photochem & Photobiology

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“…Betalains are a group of water-soluble colored compounds containing nitrogen in their structure ( Figure 2 ) [ 7 , 9 ]. They occur in most plants of the order Caryophyllales [ 10 ], and they were also found in some species of fungi of the genera Amanita and Hygrocybe [ 11 , 12 ]. These compounds consist of betalamic acid as the chromophore core that condenses with cyclo -DOPA or amino acids/amines to form red-violet betacyanins and yellow-orange betaxanthins, respectively.…”

Section: Introductionmentioning

confidence: 99%

Structural Studies on Diverse Betacyanin Classes in Matured Pigment-Rich Fruits of Basella alba L. and Basella alba L. var. ‘Rubra’ (Malabar Spinach)

Sutor-Świeży

Antonik

Dziedzic

et al. 2022

IJMS

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Identification of betacyanins in Basella alba L. and Basella alba L. var. ‘Rubra’ fruits was performed by low- and high-resolution mass spectrometry (LRMS and HRMS) as well as 1H, 13C and two-dimensional NMR which revealed hitherto completely not known betacyanin classes in the plant kingdom. Especially, the presence of unique nitrogenous acyl moieties in the structures of the pigments was ascertained by the HRMS Orbitrap detection. Except for detected polar betacyanin glycosylated derivatives, presence of a series of previously not reported pigments such as malonylated betanidin 6-O-β-glusosides with their acyl migration isomers along with the evidence of the 3′′-hydroxy-butyrylated betacyanins is reported. The first complete NMR data were obtained for novel and principal acylated gomphrenins with hydroxycinnamic acids: 6′-O-E-caffeoyl-gomphrenin (malabarin), 6′-O-E-sinapoyl-gomphrenin (gandolin), 6′-O-E-4-coumaroyl-gomphrenin (globosin) and 6′-O-E-feruloyl-gomphrenin (basellin).

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Malagasy Dye Plant Species: A Promising Source of Novel Natural Colorants with Potential Applications – A Review

Andriamanantena

Danthu

Cardon

et al. 2019

Chemistry & Biodiversity

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Due to the potentially harmful effects of some synthetic dyes, there is an increasing demand for natural colorants. Recent literature has emphasized the necessity of investigating new sources of dyes. This review discusses the biological sources of dyes derived from the rich plant diversity of Madagascar. As one of the first contributions on the use of these dyestuffs for dyeing textiles, it provides an overview of 128 dye plant species with other potential applications for coloring materials in industry. A detailed description of the botanical and chemical properties of these dyestuffs is given. We believe that the Madagascar plant diversity may be a promising source of novel colorants not yet investigated. We considered it worthwhile to carry out a thorough scientific study of a set of Malagasy plants carefully selected for their coloring properties together with their potential use and valorization in specialized industries where use of natural colorants would be a particular interest.

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Betalains

Abstract: The sections in this article are Betalain Pigments Chemistry Physiology of Betalains Genetics of Betalains Enzymology and Biotechnology Evolution of Betalains Social and Economic Value Prospectives Acknowledgements

Cited by 5 publications

References 102 publications

Revisiting the Mechanism of Hydrolysis of Betanin

Revisiting the Mechanism of Hydrolysis of Betanin

Structural Studies on Diverse Betacyanin Classes in Matured Pigment-Rich Fruits of Basella alba L. and Basella alba L. var. ‘Rubra’ (Malabar Spinach)

Malagasy Dye Plant Species: A Promising Source of Novel Natural Colorants with Potential Applications – A Review

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