Antioxidant Properties of 5,7-Dihydroxycoumarin Derivatives in in vitro Cell-free and Cell-containing Systems

Mei Hsiang Lin, Yu Shiang Chou, Yan Jyu Tsai, Duen Suey Chou

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

Background: Coumarin is a well-known plant-derived natural product, which is extensively used as a biologically active compound. Coumarins that possess hydroxyl groups in their benzenoid ring were shown to have potent antioxidant and radical-scavenging properties in various experimental models. Purposes: During our search for new types of coumarin derivatives possessing antioxidant activity, we investigated the synthesis of 5,7-dihydroxycoumarin derivatives and attempted to find potential therapeutic candidates to treat oxidative stress. Methods: A series of different cell-free and cell-containing tests was conducted. In cell-free systems, these compounds were tested by means of three electron spin resonance assays [a 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay, a xanthine/xanthine oxidase system, and a hydrogen peroxide/sodium hydroxide/dimethyl sulfoxide]. In cell-containing systems, baicalein-induced hydroxyl radical formation by B16F10 cells was used to evaluate the antioxidant properties of the coumarins. Finally, we measured the protective capacity of these coumarins against oxidative damage caused by baicalein-induced cytotoxicity in B16F10 cells. Results: All of the tested compounds were potent DPPH and superoxide radical scavengers in the DPPH and xanthine/xanthine oxidase systems, respectively. In the hydrogen peroxide/sodium hydroxide/dimethyl sulfoxide system, Compound 4 was the best radical scavenger among the 11 compounds tested. Compounds 6 and 8 were also potent hydroxyl radical scavengers but increased the formation of methyl radicals. We further evaluated the effects of the test compounds on living cells, and only Compounds 1, 3, 5, and 6 inhibited baicalein-induced hydroxyl radical formation in B16F10 cells. However, none of them could reduce baicalein-induced cytotoxicity in B16F10 cells. Conclusions: The different methods used to assess the antioxidant activities of the tested compounds can give varying results depending on the specific free radical and solvent system being used. Certain 5,7-dihydroxy-coumarins possess high antioxidant activity in vitro. Baicalein-induced cytotoxicity in B16F10 cells did not seem to be completely related to ROS generation.

Original languageEnglish
Pages (from-to)126-131
Number of pages6
JournalJournal of Experimental and Clinical Medicine(Taiwan)
Volume3
Issue number3
DOIs
Publication statusPublished - Jun 2011

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Cell-Free System
Antioxidants
Coumarins
Hydroxyl Radical
Sodium Hydroxide
Xanthine
Xanthine Oxidase
Dimethyl Sulfoxide
Hydrogen Peroxide
In Vitro Techniques
Electron Spin Resonance Spectroscopy
Biological Products
Superoxides
Free Radicals
Oxidative Stress
Theoretical Models
baicalein

Keywords

  • Baicalein
  • Coumarin
  • DPPH
  • Electron spin resonance
  • ROS
  • Xanthine oxidase

ASJC Scopus subject areas

  • Medicine(all)

Cite this

Antioxidant Properties of 5,7-Dihydroxycoumarin Derivatives in in vitro Cell-free and Cell-containing Systems. / Lin, Mei Hsiang; Chou, Yu Shiang; Tsai, Yan Jyu; Chou, Duen Suey.

In: Journal of Experimental and Clinical Medicine(Taiwan), Vol. 3, No. 3, 06.2011, p. 126-131.

Research output: Contribution to journalArticle

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abstract = "Background: Coumarin is a well-known plant-derived natural product, which is extensively used as a biologically active compound. Coumarins that possess hydroxyl groups in their benzenoid ring were shown to have potent antioxidant and radical-scavenging properties in various experimental models. Purposes: During our search for new types of coumarin derivatives possessing antioxidant activity, we investigated the synthesis of 5,7-dihydroxycoumarin derivatives and attempted to find potential therapeutic candidates to treat oxidative stress. Methods: A series of different cell-free and cell-containing tests was conducted. In cell-free systems, these compounds were tested by means of three electron spin resonance assays [a 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay, a xanthine/xanthine oxidase system, and a hydrogen peroxide/sodium hydroxide/dimethyl sulfoxide]. In cell-containing systems, baicalein-induced hydroxyl radical formation by B16F10 cells was used to evaluate the antioxidant properties of the coumarins. Finally, we measured the protective capacity of these coumarins against oxidative damage caused by baicalein-induced cytotoxicity in B16F10 cells. Results: All of the tested compounds were potent DPPH and superoxide radical scavengers in the DPPH and xanthine/xanthine oxidase systems, respectively. In the hydrogen peroxide/sodium hydroxide/dimethyl sulfoxide system, Compound 4 was the best radical scavenger among the 11 compounds tested. Compounds 6 and 8 were also potent hydroxyl radical scavengers but increased the formation of methyl radicals. We further evaluated the effects of the test compounds on living cells, and only Compounds 1, 3, 5, and 6 inhibited baicalein-induced hydroxyl radical formation in B16F10 cells. However, none of them could reduce baicalein-induced cytotoxicity in B16F10 cells. Conclusions: The different methods used to assess the antioxidant activities of the tested compounds can give varying results depending on the specific free radical and solvent system being used. Certain 5,7-dihydroxy-coumarins possess high antioxidant activity in vitro. Baicalein-induced cytotoxicity in B16F10 cells did not seem to be completely related to ROS generation.",
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AU - Tsai, Yan Jyu

AU - Chou, Duen Suey

PY - 2011/6

Y1 - 2011/6

N2 - Background: Coumarin is a well-known plant-derived natural product, which is extensively used as a biologically active compound. Coumarins that possess hydroxyl groups in their benzenoid ring were shown to have potent antioxidant and radical-scavenging properties in various experimental models. Purposes: During our search for new types of coumarin derivatives possessing antioxidant activity, we investigated the synthesis of 5,7-dihydroxycoumarin derivatives and attempted to find potential therapeutic candidates to treat oxidative stress. Methods: A series of different cell-free and cell-containing tests was conducted. In cell-free systems, these compounds were tested by means of three electron spin resonance assays [a 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay, a xanthine/xanthine oxidase system, and a hydrogen peroxide/sodium hydroxide/dimethyl sulfoxide]. In cell-containing systems, baicalein-induced hydroxyl radical formation by B16F10 cells was used to evaluate the antioxidant properties of the coumarins. Finally, we measured the protective capacity of these coumarins against oxidative damage caused by baicalein-induced cytotoxicity in B16F10 cells. Results: All of the tested compounds were potent DPPH and superoxide radical scavengers in the DPPH and xanthine/xanthine oxidase systems, respectively. In the hydrogen peroxide/sodium hydroxide/dimethyl sulfoxide system, Compound 4 was the best radical scavenger among the 11 compounds tested. Compounds 6 and 8 were also potent hydroxyl radical scavengers but increased the formation of methyl radicals. We further evaluated the effects of the test compounds on living cells, and only Compounds 1, 3, 5, and 6 inhibited baicalein-induced hydroxyl radical formation in B16F10 cells. However, none of them could reduce baicalein-induced cytotoxicity in B16F10 cells. Conclusions: The different methods used to assess the antioxidant activities of the tested compounds can give varying results depending on the specific free radical and solvent system being used. Certain 5,7-dihydroxy-coumarins possess high antioxidant activity in vitro. Baicalein-induced cytotoxicity in B16F10 cells did not seem to be completely related to ROS generation.

AB - Background: Coumarin is a well-known plant-derived natural product, which is extensively used as a biologically active compound. Coumarins that possess hydroxyl groups in their benzenoid ring were shown to have potent antioxidant and radical-scavenging properties in various experimental models. Purposes: During our search for new types of coumarin derivatives possessing antioxidant activity, we investigated the synthesis of 5,7-dihydroxycoumarin derivatives and attempted to find potential therapeutic candidates to treat oxidative stress. Methods: A series of different cell-free and cell-containing tests was conducted. In cell-free systems, these compounds were tested by means of three electron spin resonance assays [a 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay, a xanthine/xanthine oxidase system, and a hydrogen peroxide/sodium hydroxide/dimethyl sulfoxide]. In cell-containing systems, baicalein-induced hydroxyl radical formation by B16F10 cells was used to evaluate the antioxidant properties of the coumarins. Finally, we measured the protective capacity of these coumarins against oxidative damage caused by baicalein-induced cytotoxicity in B16F10 cells. Results: All of the tested compounds were potent DPPH and superoxide radical scavengers in the DPPH and xanthine/xanthine oxidase systems, respectively. In the hydrogen peroxide/sodium hydroxide/dimethyl sulfoxide system, Compound 4 was the best radical scavenger among the 11 compounds tested. Compounds 6 and 8 were also potent hydroxyl radical scavengers but increased the formation of methyl radicals. We further evaluated the effects of the test compounds on living cells, and only Compounds 1, 3, 5, and 6 inhibited baicalein-induced hydroxyl radical formation in B16F10 cells. However, none of them could reduce baicalein-induced cytotoxicity in B16F10 cells. Conclusions: The different methods used to assess the antioxidant activities of the tested compounds can give varying results depending on the specific free radical and solvent system being used. Certain 5,7-dihydroxy-coumarins possess high antioxidant activity in vitro. Baicalein-induced cytotoxicity in B16F10 cells did not seem to be completely related to ROS generation.

KW - Baicalein

KW - Coumarin

KW - DPPH

KW - Electron spin resonance

KW - ROS

KW - Xanthine oxidase

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