Identification of novel low-weight sulfhydryl conjugates of oxidized 5‑O- and 6‑O‑substituted betanidin pigments
Authors:
- Agnieszka Kumorkiewicz-Jamro,
- Łukasz Popenda,
- Sławomir Wybraniec
Abstract
The formation of conjugates of oxidized betacyanin pigments with selected low-weight sulfhydryl scavengers was studied. Short-lived quinonoids, quinone methides, and aminochromes derived from oxidized betacyanins are able to form adducts with different efficiencies. In this report, mass spectrometric and NMR identifications of CS-linked conjugates of cysteine, cysteamine, N-acetylcysteine, and DL-dithiolthreitol with quinonoid forms generated through oxidation of betanidin, betanin, and gomphrenin is presented. An adduct that formed between cysteine and quinonoid generated from betanin by its oxidation and decarboxylation (2-decarboxy-xanbetanin) was detected and reported for the first time. The most stable gomphrenin CS-conjugate, N-acetylcysteinylated gomphrenin, was isolated by semipreparative chromatography and its structure was established by NMR analysis. This enabled to confirm the conjugation position at carbon C-4 and to indicate the presence of a dopachromic intermediate during oxidation of gomphrenin. Conjugation of betacyanins with thiol-bearing moieties may generate new molecules with modified chemical and biological properties. Obtained results confirm that gomphrenin is capable of forming CS-conjugates with higher efficiency than betanin.
- Record ID
- CUT69a60f9368e048cd98cdad6af2b9e82d
- Publication categories
- ;
- Author
- Journal series
- ACS Omega, ISSN 2470-1343
- Issue year
- 2020
- Vol
- 5
- No
- 25
- Pages
- 14955-14967
- Other elements of collation
- rys.; tab.; wykr.; Bibliografia (na s.) - 14966-14967; Bibliografia (liczba pozycji) - 46; Oznaczenie streszczenia - Abstr.; Data udostępnienia on-line - 2020-06-16; Numeracja w czasopiśmie - Vol. 5, Iss. 25
- Keywords in English
- CS-conjugates, trapping agent, betalains, betanidin, betanin, gomphrenin, Basella alba, Malabar spinach, mass spectrometry, fragmentation pattern, NMR elucidation, fragmentation, oxidation, peptides and proteins, conjugate acid-base pairs, ions
- DOI
- DOI:10.1021/acsomega.0c00378 Opening in a new tab
- URL
- https://pubs.acs.org/doi/10.1021/acsomega.0c00378 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)
- 70
- Additional fields
- Indeksowana w: Web of Science, Scopus
- Uniform Resource Identifier
- https://cris.pk.edu.pl/info/article/CUT69a60f9368e048cd98cdad6af2b9e82d/
- URN
urn:pkr-prod:CUT69a60f9368e048cd98cdad6af2b9e82d
* 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.