Antioxidant and semicarbazide-sensitive amine oxidase inhibitory activities of alginic acid hydroxamates

Der Zen Liu, Wen Chung Wu, Hong Jen Liang, Wen Chi Hou

Research output: Contribution to journalArticle

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Abstract

The commercial polysaccharides of alginic acid (medium (3500 cps, 2% solution) and low (250 cps, 2% solution) viscosities) were esterified with acidic methanol (1 mmol L-1 HCl) at 4°C with gentle stirring for 5 days to obtain methyl esters of medium-viscosity alginic acid (ME-MVA) and low-viscosity alginic acid (ME-LVA). These ME-MVA and ME-LVA were reacted with alkaline hydroxylamine to obtain medium-viscosity alginic acid hydroxamates (MVA-NHOH) and LVA-NHOH. The percentages of hydroxamic acid content in MVA-NHOH and LVA-NHOH were calculated as 25% and 20%, respectively. The hydroxamate derivatives of alginic acid were used to test the antioxidant and semicarbazide-sensitive amine oxidase (SSAO) inhibitory activities in comparison with original materials (MVA and LVA). The half-inhibition concentrations, IC50, of scavenging activity against 1,1-diphenyl-2-picrylhydrazyl (DPPH) were 24.5 and 29.8 μg mL-1 for MVA-NHOH and LVA-NHOH, respectively. However, few scavenging activities of the MVA and LVA were found at the same concentrations. The IC50 of the positive control of butylated hydroxytoluene was 5 μg mL-1. The scavenging activity of DPPH radical was pH-dependent, and the optimal pH for both of MVA-NHOH and LVA-NHOH was the Tris-HCl buffer (pH 7.9). Using electron spin resonance (ESR) to detect the activity of scavenging hydroxyl radicals, both alginic acid hydroxamates showed dose-dependent scavenging activities, and the IC 50 was 90 and 92 μg mL-1, respectively, for MVA-NHOH and LVA-NHOH. Both alginic acid hydroxamates also exhibited protection against hydroxyl radical-mediated DNA damage. Both MVA-NHOH and LVA-NHOH showed dose-dependent inhibitory activities against bovine SSAO (2.53 units); the IC50 was 0.16 and 0.09 μg mL-1, respectively, for MVA-NHOH and LVA-NHOH, compared with 3.8 μg mL-1 of semicarbazide (positive controls). Amine oxidase activity staining also revealed that both MVA-NHOH and LVA-NHOH exhibited SSAO inhibitory activities. Both MVA-NHOH and LVA-NHOH showed mixed non-competitive inhibition against bovine SSAO. It was found that the V′max value was reduced and the K′m value was either increased (added MVA-NHOH, 0.05 μg mL-1) or reduced (added LVA-NHOH, 0.11 μg mL-1) in the presence of alginic acid hydroxamate.

Original languageEnglish
Pages (from-to)138-146
Number of pages9
JournalJournal of the Science of Food and Agriculture
Volume87
Issue number1
DOIs
Publication statusPublished - Jan 15 2007

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Amine Oxidase (Copper-Containing)
alginates
amines
Antioxidants
antioxidants
Viscosity
Scavenging
viscosity
inhibitory concentration 50
Inhibitory Concentration 50
hydroxyl radicals
Hydroxyl Radical
Esters
esters
alginic acid
hydroxamic acids
Hydroxamic Acids
Butylated Hydroxytoluene
Hydroxylamine
Tromethamine

Keywords

  • Alginic acid hydroxamate
  • Antioxidant activity
  • Electron spin resonance (ESR)
  • Semicarbazide-sensitive amine oxidase (SSAO)

ASJC Scopus subject areas

  • Agricultural and Biological Sciences (miscellaneous)
  • Food Science
  • Chemistry (miscellaneous)

Cite this

Antioxidant and semicarbazide-sensitive amine oxidase inhibitory activities of alginic acid hydroxamates. / Liu, Der Zen; Wu, Wen Chung; Liang, Hong Jen; Hou, Wen Chi.

In: Journal of the Science of Food and Agriculture, Vol. 87, No. 1, 15.01.2007, p. 138-146.

Research output: Contribution to journalArticle

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abstract = "The commercial polysaccharides of alginic acid (medium (3500 cps, 2{\%} solution) and low (250 cps, 2{\%} solution) viscosities) were esterified with acidic methanol (1 mmol L-1 HCl) at 4°C with gentle stirring for 5 days to obtain methyl esters of medium-viscosity alginic acid (ME-MVA) and low-viscosity alginic acid (ME-LVA). These ME-MVA and ME-LVA were reacted with alkaline hydroxylamine to obtain medium-viscosity alginic acid hydroxamates (MVA-NHOH) and LVA-NHOH. The percentages of hydroxamic acid content in MVA-NHOH and LVA-NHOH were calculated as 25{\%} and 20{\%}, respectively. The hydroxamate derivatives of alginic acid were used to test the antioxidant and semicarbazide-sensitive amine oxidase (SSAO) inhibitory activities in comparison with original materials (MVA and LVA). The half-inhibition concentrations, IC50, of scavenging activity against 1,1-diphenyl-2-picrylhydrazyl (DPPH) were 24.5 and 29.8 μg mL-1 for MVA-NHOH and LVA-NHOH, respectively. However, few scavenging activities of the MVA and LVA were found at the same concentrations. The IC50 of the positive control of butylated hydroxytoluene was 5 μg mL-1. The scavenging activity of DPPH radical was pH-dependent, and the optimal pH for both of MVA-NHOH and LVA-NHOH was the Tris-HCl buffer (pH 7.9). Using electron spin resonance (ESR) to detect the activity of scavenging hydroxyl radicals, both alginic acid hydroxamates showed dose-dependent scavenging activities, and the IC 50 was 90 and 92 μg mL-1, respectively, for MVA-NHOH and LVA-NHOH. Both alginic acid hydroxamates also exhibited protection against hydroxyl radical-mediated DNA damage. Both MVA-NHOH and LVA-NHOH showed dose-dependent inhibitory activities against bovine SSAO (2.53 units); the IC50 was 0.16 and 0.09 μg mL-1, respectively, for MVA-NHOH and LVA-NHOH, compared with 3.8 μg mL-1 of semicarbazide (positive controls). Amine oxidase activity staining also revealed that both MVA-NHOH and LVA-NHOH exhibited SSAO inhibitory activities. Both MVA-NHOH and LVA-NHOH showed mixed non-competitive inhibition against bovine SSAO. It was found that the V′max value was reduced and the K′m value was either increased (added MVA-NHOH, 0.05 μg mL-1) or reduced (added LVA-NHOH, 0.11 μg mL-1) in the presence of alginic acid hydroxamate.",
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N2 - The commercial polysaccharides of alginic acid (medium (3500 cps, 2% solution) and low (250 cps, 2% solution) viscosities) were esterified with acidic methanol (1 mmol L-1 HCl) at 4°C with gentle stirring for 5 days to obtain methyl esters of medium-viscosity alginic acid (ME-MVA) and low-viscosity alginic acid (ME-LVA). These ME-MVA and ME-LVA were reacted with alkaline hydroxylamine to obtain medium-viscosity alginic acid hydroxamates (MVA-NHOH) and LVA-NHOH. The percentages of hydroxamic acid content in MVA-NHOH and LVA-NHOH were calculated as 25% and 20%, respectively. The hydroxamate derivatives of alginic acid were used to test the antioxidant and semicarbazide-sensitive amine oxidase (SSAO) inhibitory activities in comparison with original materials (MVA and LVA). The half-inhibition concentrations, IC50, of scavenging activity against 1,1-diphenyl-2-picrylhydrazyl (DPPH) were 24.5 and 29.8 μg mL-1 for MVA-NHOH and LVA-NHOH, respectively. However, few scavenging activities of the MVA and LVA were found at the same concentrations. The IC50 of the positive control of butylated hydroxytoluene was 5 μg mL-1. The scavenging activity of DPPH radical was pH-dependent, and the optimal pH for both of MVA-NHOH and LVA-NHOH was the Tris-HCl buffer (pH 7.9). Using electron spin resonance (ESR) to detect the activity of scavenging hydroxyl radicals, both alginic acid hydroxamates showed dose-dependent scavenging activities, and the IC 50 was 90 and 92 μg mL-1, respectively, for MVA-NHOH and LVA-NHOH. Both alginic acid hydroxamates also exhibited protection against hydroxyl radical-mediated DNA damage. Both MVA-NHOH and LVA-NHOH showed dose-dependent inhibitory activities against bovine SSAO (2.53 units); the IC50 was 0.16 and 0.09 μg mL-1, respectively, for MVA-NHOH and LVA-NHOH, compared with 3.8 μg mL-1 of semicarbazide (positive controls). Amine oxidase activity staining also revealed that both MVA-NHOH and LVA-NHOH exhibited SSAO inhibitory activities. Both MVA-NHOH and LVA-NHOH showed mixed non-competitive inhibition against bovine SSAO. It was found that the V′max value was reduced and the K′m value was either increased (added MVA-NHOH, 0.05 μg mL-1) or reduced (added LVA-NHOH, 0.11 μg mL-1) in the presence of alginic acid hydroxamate.

AB - The commercial polysaccharides of alginic acid (medium (3500 cps, 2% solution) and low (250 cps, 2% solution) viscosities) were esterified with acidic methanol (1 mmol L-1 HCl) at 4°C with gentle stirring for 5 days to obtain methyl esters of medium-viscosity alginic acid (ME-MVA) and low-viscosity alginic acid (ME-LVA). These ME-MVA and ME-LVA were reacted with alkaline hydroxylamine to obtain medium-viscosity alginic acid hydroxamates (MVA-NHOH) and LVA-NHOH. The percentages of hydroxamic acid content in MVA-NHOH and LVA-NHOH were calculated as 25% and 20%, respectively. The hydroxamate derivatives of alginic acid were used to test the antioxidant and semicarbazide-sensitive amine oxidase (SSAO) inhibitory activities in comparison with original materials (MVA and LVA). The half-inhibition concentrations, IC50, of scavenging activity against 1,1-diphenyl-2-picrylhydrazyl (DPPH) were 24.5 and 29.8 μg mL-1 for MVA-NHOH and LVA-NHOH, respectively. However, few scavenging activities of the MVA and LVA were found at the same concentrations. The IC50 of the positive control of butylated hydroxytoluene was 5 μg mL-1. The scavenging activity of DPPH radical was pH-dependent, and the optimal pH for both of MVA-NHOH and LVA-NHOH was the Tris-HCl buffer (pH 7.9). Using electron spin resonance (ESR) to detect the activity of scavenging hydroxyl radicals, both alginic acid hydroxamates showed dose-dependent scavenging activities, and the IC 50 was 90 and 92 μg mL-1, respectively, for MVA-NHOH and LVA-NHOH. Both alginic acid hydroxamates also exhibited protection against hydroxyl radical-mediated DNA damage. Both MVA-NHOH and LVA-NHOH showed dose-dependent inhibitory activities against bovine SSAO (2.53 units); the IC50 was 0.16 and 0.09 μg mL-1, respectively, for MVA-NHOH and LVA-NHOH, compared with 3.8 μg mL-1 of semicarbazide (positive controls). Amine oxidase activity staining also revealed that both MVA-NHOH and LVA-NHOH exhibited SSAO inhibitory activities. Both MVA-NHOH and LVA-NHOH showed mixed non-competitive inhibition against bovine SSAO. It was found that the V′max value was reduced and the K′m value was either increased (added MVA-NHOH, 0.05 μg mL-1) or reduced (added LVA-NHOH, 0.11 μg mL-1) in the presence of alginic acid hydroxamate.

KW - Alginic acid hydroxamate

KW - Antioxidant activity

KW - Electron spin resonance (ESR)

KW - Semicarbazide-sensitive amine oxidase (SSAO)

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