Structural Study on Hypochlorous Acid-Mediated Chlorination of Betanin and Its Decarboxylated Derivatives from an Anti-Inflammatory Beta vulgaris L. Extract.
IT-TOF
NMR
betacyanins
betalain rich extract
hypochlorous acid
inflammation
Journal
Molecules (Basel, Switzerland)
ISSN: 1420-3049
Titre abrégé: Molecules
Pays: Switzerland
ID NLM: 100964009
Informations de publication
Date de publication:
16 Jan 2020
16 Jan 2020
Historique:
received:
10
12
2019
revised:
10
01
2020
accepted:
14
01
2020
entrez:
23
1
2020
pubmed:
23
1
2020
medline:
21
10
2020
Statut:
epublish
Résumé
Hypochlorous acid (HOCl) produced by neutrophils is a part of the natural innate immune response system in the human body, but excessive levels of HOCl can ultimately be detrimental to health. Recent reports suggest that betacyanin plant pigments can act as potent scavengers of inflammatory factors and are notably effective against HOCl. In this contribution, chlorination mechanism and position of the electrophilic substitution in betacyanins was studied by high-resolution mass spectrometry and further structural analyses by NMR techniques, which completed the identification of the chlorinated betacyanins. For the study on the influence of the position of decarboxylation on the chlorination mechanism, a comparison of the chlorination position between betanin as well as 17-, and 2,17-decarboxylated betanins was performed. The structural study confirmed that the chlorination position in betanin occurs within the dihydropyridinic moiety at carbon C-18. Therefore, out of the aqueous free chlorine equilibrium species: HOCl, OCl
Identifiants
pubmed: 31963358
pii: molecules25020378
doi: 10.3390/molecules25020378
pmc: PMC7024289
pii:
doi:
Substances chimiques
Anti-Inflammatory Agents
0
Betacyanins
0
Plant Extracts
0
betanin
5YJC992ZP6
Hypochlorous Acid
712K4CDC10
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Subventions
Organisme : Narodowe Centrum Nauki
ID : UMO-2014/13/B/ST4/04854
Déclaration de conflit d'intérêts
The authors declare no conflict of interest.
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