Yellow pigments produced by oxidative oligomerization of dihydrochalcone glucoside and the reaction mechanism.
Dihydrochalcone
Lithocarpus polystachyus
Lithocarputin
Oxidation
Pigment
Journal
Food chemistry
ISSN: 1873-7072
Titre abrégé: Food Chem
Pays: England
ID NLM: 7702639
Informations de publication
Date de publication:
15 Nov 2023
15 Nov 2023
Historique:
received:
10
05
2023
revised:
15
06
2023
accepted:
17
06
2023
medline:
19
7
2023
pubmed:
26
6
2023
entrez:
25
6
2023
Statut:
ppublish
Résumé
From the dried leaves of Lithocarpus polystachyus, yellow pigments, lithocarputins B (11) and C (12), were isolated with a colorless dihydrochalcone dimer, lithocarputin A (10). The pigments 11 and 12 are dimeric dihydrochalcone glycosides with bicyclo[3.2.1]octane structures. Each pigment is a diastereomeric mixture with enantiomeric aglycones that could not be separated. The production mechanisms of the pigments were proposed based on the in vitro enzymatic preparation from trilobatin (1), the major dihydrochalcone glucoside of L. polystachyus. The majority of the pigments in the dried leaves were the oligomers of the dihydrochalcone glycosides generated by a mechanism similar to dimerization. The pigments are probably artifacts produced in the drying process. This is the first report disclosing a detailed chemical mechanism for pigment formation from dihydrochalcone.
Identifiants
pubmed: 37356249
pii: S0308-8146(23)01289-X
doi: 10.1016/j.foodchem.2023.136671
pii:
doi:
Substances chimiques
dihydrochalcone
H5W525SX7Q
Glucosides
0
Pigments, Biological
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
136671Informations de copyright
Copyright © 2023 Elsevier Ltd. All rights reserved.
Déclaration de conflit d'intérêts
Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.