On the free radical scavenging and metallic ion chelating activities of pyridoxal - Could the pro-oxidant risk be competitive?
Copyright © 2022 Elsevier Ltd. All rights reserved..
Primary and secondary antioxidant activities of pyridoxal have been investigated by using density functional theory (DFT) at the M05-2X level combined with 6-311++G(d,p) basis set for non-metallic atoms and LanL2DZ for metallic ions. The former has been examined by its free radical scavenging activity towards HOO●, HO●, and NO2●via different mechanisms including formal hydrogen transfer (FHT), proton transfer (PT), single electron transfer (SET), and radical adduct formation (RAF). The latter has been accomplished through its transition metal-chelating ability with Fe(III)/Fe(II) and Cu(II)/Cu(I) ions. The results show that pyridoxal illustrates as an efficient radical scavenger, especially, for HO● and NO2● in water. The overall rate constants (koverall) for the reactions with HOO●, HO●, and NO2● radicals are 1.30 × 104, 5.76 × 109, and 1.43 × 109 M-1s-1, respectively. The SET from the anionic state is the most dominant for the HOO● and NO2● scavenging reactions, while both RAF and SET contribute largely to the reaction with highly reactive HO● radicals. Moreover, the anionic form of pyridoxal demonstrates a better role as a metal chelator than the neutral. However, the pro-oxidant risks of the formed complexes could be observed if there are superoxide radical anion (O2●-) and ascorbate (Asc-) in aqueous media.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2022 |
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| Erschienen: |
2022 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:199 |
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| Enthalten in: |
Phytochemistry - 199(2022) vom: 01. Juli, Seite 113176 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Ngo, Thi Chinh [VerfasserIn] |
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| Links: |
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| Anmerkungen: |
Date Completed 18.05.2022 Date Revised 18.05.2022 published: Print-Electronic Citation Status MEDLINE |
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| doi: |
10.1016/j.phytochem.2022.113176 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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NLM339201010 |
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| 100 | 1 | |a Ngo, Thi Chinh |e verfasserin |4 aut | |
| 245 | 1 | 0 | |a On the free radical scavenging and metallic ion chelating activities of pyridoxal - Could the pro-oxidant risk be competitive? |
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| 500 | |a Date Revised 18.05.2022 | ||
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| 500 | |a Citation Status MEDLINE | ||
| 520 | |a Copyright © 2022 Elsevier Ltd. All rights reserved. | ||
| 520 | |a Primary and secondary antioxidant activities of pyridoxal have been investigated by using density functional theory (DFT) at the M05-2X level combined with 6-311++G(d,p) basis set for non-metallic atoms and LanL2DZ for metallic ions. The former has been examined by its free radical scavenging activity towards HOO●, HO●, and NO2●via different mechanisms including formal hydrogen transfer (FHT), proton transfer (PT), single electron transfer (SET), and radical adduct formation (RAF). The latter has been accomplished through its transition metal-chelating ability with Fe(III)/Fe(II) and Cu(II)/Cu(I) ions. The results show that pyridoxal illustrates as an efficient radical scavenger, especially, for HO● and NO2● in water. The overall rate constants (koverall) for the reactions with HOO●, HO●, and NO2● radicals are 1.30 × 104, 5.76 × 109, and 1.43 × 109 M-1s-1, respectively. The SET from the anionic state is the most dominant for the HOO● and NO2● scavenging reactions, while both RAF and SET contribute largely to the reaction with highly reactive HO● radicals. Moreover, the anionic form of pyridoxal demonstrates a better role as a metal chelator than the neutral. However, the pro-oxidant risks of the formed complexes could be observed if there are superoxide radical anion (O2●-) and ascorbate (Asc-) in aqueous media | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Antioxidant | |
| 650 | 4 | |a DFT calculations | |
| 650 | 4 | |a Free radicals | |
| 650 | 4 | |a Metal chelating | |
| 650 | 4 | |a Pro-oxidant | |
| 650 | 4 | |a Pyridoxal | |
| 650 | 4 | |a Vitamin B6 | |
| 650 | 7 | |a Chelating Agents |2 NLM | |
| 650 | 7 | |a Ferric Compounds |2 NLM | |
| 650 | 7 | |a Free Radical Scavengers |2 NLM | |
| 650 | 7 | |a Reactive Oxygen Species |2 NLM | |
| 650 | 7 | |a Superoxides |2 NLM | |
| 650 | 7 | |a 11062-77-4 |2 NLM | |
| 650 | 7 | |a Pyridoxal |2 NLM | |
| 650 | 7 | |a 3THM379K8A |2 NLM | |
| 650 | 7 | |a Nitrogen Dioxide |2 NLM | |
| 650 | 7 | |a S7G510RUBH |2 NLM | |
| 700 | 1 | |a Truong, Dinh Hieu |e verfasserin |4 aut | |
| 700 | 1 | |a Nguyen, Thi Thuy Nga |e verfasserin |4 aut | |
| 700 | 1 | |a Quang, Duong Tuan |e verfasserin |4 aut | |
| 700 | 1 | |a Dao, Duy Quang |e verfasserin |4 aut | |
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