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Structural Study on Hypochlorous Acid-Mediated Chlorination of Betanin and Its Decarboxylated Derivatives from an Anti-Inflammatory Beta vulgaris L. Extract

1
Department of Analytical Chemistry, Faculty of Chemical Engineering and Technology, Cracow University of Technology, ul. Warszawska 24, 31-155 Cracow, Poland
2
Chemistry Research, VDF FutureCeuticals, Inc., Momence, IL 60954, USA
3
Food Science and Human Nutrition, University of Illinois at Urbana-Champaign, Urbana, IL 61801, USA
4
FutureCeuticals, Inc., 23 Peters Canyon Rd, Irvine, CA 92606, USA
5
NanoBioMedical Centre, Adam Mickiewicz University in Poznan, Wszechnicy Piastowskiej 3, 61-614 Poznan, Poland
*
Author to whom correspondence should be addressed.
Molecules 2020, 25(2), 378; https://doi.org/10.3390/molecules25020378 (registering DOI)
Received: 10 December 2019 / Revised: 10 January 2020 / Accepted: 14 January 2020 / Published: 16 January 2020
(This article belongs to the Special Issue Bioactive Natural Compounds and Their Mechanisms of Action)
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. View Full-Text
Keywords: betacyanins; betalain rich extract; IT-TOF; NMR; inflammation; hypochlorous acid betacyanins; betalain rich extract; IT-TOF; NMR; inflammation; hypochlorous acid
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Kumorkiewicz-Jamro, A.; Starzak, K.; Sutor, K.; Nemzer, B.; Pietrzkowski, Z.; Popenda, Ł.; Wybraniec, S. Structural Study on Hypochlorous Acid-Mediated Chlorination of Betanin and Its Decarboxylated Derivatives from an Anti-Inflammatory Beta vulgaris L. Extract. Molecules 2020, 25, 378.

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