Yellow pigments produced by oxidative oligomerization of dihydrochalcone glucoside and the reaction mechanism
Copyright © 2023 Elsevier Ltd. All rights reserved..
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.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2023 |
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| Erschienen: |
2023 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:426 |
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| Enthalten in: |
Food chemistry - 426(2023) vom: 15. Nov., Seite 136671 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Liu, Zhang-Bin [VerfasserIn] |
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| Links: |
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| Themen: |
Dihydrochalcone |
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| Anmerkungen: |
Date Completed 31.07.2023 Date Revised 31.07.2023 published: Print-Electronic Citation Status MEDLINE |
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| doi: |
10.1016/j.foodchem.2023.136671 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| 500 | |a Date Revised 31.07.2023 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status MEDLINE | ||
| 520 | |a Copyright © 2023 Elsevier Ltd. All rights reserved. | ||
| 520 | |a 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 | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Dihydrochalcone | |
| 650 | 4 | |a Lithocarpus polystachyus | |
| 650 | 4 | |a Lithocarputin | |
| 650 | 4 | |a Oxidation | |
| 650 | 4 | |a Pigment | |
| 650 | 7 | |a dihydrochalcone |2 NLM | |
| 650 | 7 | |a H5W525SX7Q |2 NLM | |
| 650 | 7 | |a Glucosides |2 NLM | |
| 650 | 7 | |a Pigments, Biological |2 NLM | |
| 700 | 1 | |a Matsuo, Yosuke |e verfasserin |4 aut | |
| 700 | 1 | |a Saito, Yoshinori |e verfasserin |4 aut | |
| 700 | 1 | |a Huang, Yong-Lin |e verfasserin |4 aut | |
| 700 | 1 | |a Li, Dian-Peng |e verfasserin |4 aut | |
| 700 | 1 | |a Nonaka, Gen-Ichiro |e verfasserin |4 aut | |
| 700 | 1 | |a Tanaka, Takashi |e verfasserin |4 aut | |
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