Structural study on hypochlorous acid-mediated chlorination of betanin and its decarboxylated derivatives from an anti-inflammatory Beta vulgaris L. extract
Authors:
- Agnieszka Kumorkiewicz-Jamro,
- Karolina Starzak,
- Katarzyna Sutor,
- Boris Nemzer,
- Zbigniew Pietrzkowski,
- Łukasz Popenda,
- Sławomir Wybraniec
Abstract
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−, Cl2, and Cl2O, the most potent chlorinating agents are HOCl and Cl2O postulated previously and the attack of the Cl⁺ ion on the carbon C‐18 with a cyclic intermediate version is considered.
- Record ID
- CUTe5a905c149c046cf8e3684123cb1a0fd
- Publication categories
- ;
- Author
- Journal series
- Molecules, ISSN , e-ISSN 1420-3049, Biweekly
- Issue year
- 2020
- Vol
- 25
- No
- 2
- Pages
- [1-11]
- Article number
- 378
- Other elements of collation
- rys.; tab.; wykr.; Bibliografia (na s.) - 10-11; Bibliografia (liczba pozycji) - 22; Oznaczenie streszczenia - Abstr.; Numeracja w czasopiśmie - Vol. 25, Iss. 2, Spec. Iss.
- Substantive notes
- Special Issue: Bioactive Natural Compounds and Their Mechanisms of Action
- Keywords in English
- betacyanins, betalain rich extract, IT‐TOF, NMR, inflammation, hypochlorous acid
- DOI
- DOI:10.3390/molecules25020378 Opening in a new tab
- URL
- https://www.mdpi.com/1420-3049/25/2/378 Opening in a new tab
- Related project
- Badania mechanizmu utleniania pigmentów betacyjanin. . Project leader at PK: , ,
Projects financed by NSC [Projekty finansowane przez NCN] - Language
- eng (en) English
- License
- Score (nominal)
- 140
- Additional fields
- Indeksowana w: Web of Science, Scopus
- Uniform Resource Identifier
- https://cris.pk.edu.pl/info/article/CUTe5a905c149c046cf8e3684123cb1a0fd/
- URN
urn:pkr-prod:CUTe5a905c149c046cf8e3684123cb1a0fd
* presented citation count is obtained through Internet information analysis, and it is close to the number calculated by the Publish or PerishOpening in a new tab system.