The Role of Phenolic Hydroxy Groups in the Free Radical Scavenging Activity of Betalains

Free radical scavenging compounds play important roles as health-protecting factors. Betalains are natural water-soluble pigments present in most plant families belonging to the order Caryophyllales. They are the subject of increasing attention following the discovery of their antiradical capacity,...

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Published inJournal of natural products (Washington, D.C.) Vol. 72; no. 6; pp. 1142 - 1146
Main Authors Gandía-Herrero, Fernando, Escribano, Josefa, García-Carmona, Francisco
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society and American Society of Pharmacognosy 26.06.2009
Amer Chemical Soc
American Society of Pharmacognosy
Subjects
pH
Online AccessGet full text
ISSN0163-3864
1520-6025
1520-6025
DOI10.1021/np900131r

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Abstract Free radical scavenging compounds play important roles as health-protecting factors. Betalains are natural water-soluble pigments present in most plant families belonging to the order Caryophyllales. They are the subject of increasing attention following the discovery of their antiradical capacity, but a systematic analysis of the structural features involved in the activity is necessary. In this paper, both natural and previously unconsidered betaxanthins were obtained in order to study the role of phenolic hydroxy groups in the high free radical scavenging activity of betalains. Pigments were characterized spectrophotometrically, chromatographically, and by ESI-MS, and their antiradical and antioxidant properties were studied under the ABTS•+ radical and FRAP assays. A high intrinsic activity is described that is not linked to the presence of hydroxy groups or aromaticity in the pigment structure. In addition, the presence of phenolic hydroxy groups implies an enhancement of the antiradical activity, reaching a TEAC value in the ABTS•+ assay of 5.8 ± 0.2 for the pure compound with two hydroxy groups.
AbstractList Free radical scavenging compounds play important roles as health- protecting factors. Betalains are natural water-soluble pigments present in most plant families belonging to the order Caryophyllales. They are the subject of increasing attention following the discovery of their antiradical capacity, but a systematic analysis of the structural features involved in the activity is necessary. In this paper, both natural and previously unconsidered betaxanthins were obtained in order to study the role of phenolic hydroxy groups in the high free radical scavenging activity of betalains. Pigments were characterized spectrophotometrically, chromatographically, and by ESI-MS, and their antiradical and antioxidant properties were studied under the ABTS+ radical and FRAP assays. A high intrinsic activity is described that is not linked to the presence of hydroxy groups or aromaticity in the pigment structure. In addition, the presence of phenolic hydroxy groups implies an enhancement of the antiradical activity, reaching a TEAC value in the ABTS+ assay of 5.8 +/- 0.2 for the pure compound with two hydroxy groups.
Free radical scavenging compounds play important roles as health-protecting factors. Betalains are natural water-soluble pigments present in most plant families belonging to the order Caryophyllales. They are the subject of increasing attention following the discovery of their antiradical capacity, but a systematic analysis of the structural features involved in the activity is necessary. In this paper, both natural and previously unconsidered betaxanthins were obtained in order to study the role of phenolic hydroxy groups in the high free radical scavenging activity of betalains. Pigments were characterized spectrophotometrically, chromatographically, and by ESI-MS, and their antiradical and antioxidant properties were studied under the ABTS•+ radical and FRAP assays. A high intrinsic activity is described that is not linked to the presence of hydroxy groups or aromaticity in the pigment structure. In addition, the presence of phenolic hydroxy groups implies an enhancement of the antiradical activity, reaching a TEAC value in the ABTS•+ assay of 5.8 ± 0.2 for the pure compound with two hydroxy groups.
Free radical scavenging compounds play important roles as health-protecting factors. Betalains are natural water-soluble pigments present in most plant families belonging to the order Caryophyllales. They are the subject of increasing attention following the discovery of their antiradical capacity, but a systematic analysis of the structural features involved in the activity is necessary. In this paper, both natural and previously unconsidered betaxanthins were obtained in order to study the role of phenolic hydroxy groups in the high free radical scavenging activity of betalains. Pigments were characterized spectrophotometrically, chromatographically, and by ESI-MS, and their antiradical and antioxidant properties were studied under the ABTS(*+) radical and FRAP assays. A high intrinsic activity is described that is not linked to the presence of hydroxy groups or aromaticity in the pigment structure. In addition, the presence of phenolic hydroxy groups implies an enhancement of the antiradical activity, reaching a TEAC value in the ABTS(*+) assay of 5.8 +/- 0.2 for the pure compound with two hydroxy groups.Free radical scavenging compounds play important roles as health-protecting factors. Betalains are natural water-soluble pigments present in most plant families belonging to the order Caryophyllales. They are the subject of increasing attention following the discovery of their antiradical capacity, but a systematic analysis of the structural features involved in the activity is necessary. In this paper, both natural and previously unconsidered betaxanthins were obtained in order to study the role of phenolic hydroxy groups in the high free radical scavenging activity of betalains. Pigments were characterized spectrophotometrically, chromatographically, and by ESI-MS, and their antiradical and antioxidant properties were studied under the ABTS(*+) radical and FRAP assays. A high intrinsic activity is described that is not linked to the presence of hydroxy groups or aromaticity in the pigment structure. In addition, the presence of phenolic hydroxy groups implies an enhancement of the antiradical activity, reaching a TEAC value in the ABTS(*+) assay of 5.8 +/- 0.2 for the pure compound with two hydroxy groups.
Free radical scavenging compounds play important roles as health-protecting factors. Betalains are natural water-soluble pigments present in most plant families belonging to the order Caryophyllales. They are the subject of increasing attention following the discovery of their antiradical capacity, but a systematic analysis of the structural features involved in the activity is necessary. In this paper, both natural and previously unconsidered betaxanthins were obtained in order to study the role of phenolic hydroxy groups in the high free radical scavenging activity of betalains. Pigments were characterized spectrophotometrically, chromatographically, and by ESI-MS, and their antiradical and antioxidant properties were studied under the ABTS(center dot+) radical and FRAP assays. A high intrinsic activity is described that is not linked to the presence of hydroxy groups or aromaticity in the pigment structure. In addition, the presence of phenolic hydroxy groups implies an enhancement of the antiradical activity, reaching a TEAC value in the ABTS(center dot+) assay of 5.8 +/- 0.2 for the pure compound with two hydroxy groups.
Author Escribano, Josefa
García-Carmona, Francisco
Gandía-Herrero, Fernando
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DocumentTitleAlternate Free Radical Scavenging Activity of Betalains
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Issue 6
Keywords PERFORMANCE LIQUID-CHROMATOGRAPHY
ANTIOXIDANT ACTIVITY
PEAR
FLUORESCENCE
ANTIRADICAL ACTIVITY
BIOSYNTHESIS
RED BEET
BETAXANTHIN
BETANIN
IONIZATION MASS-SPECTROMETRY
Nitrogen heterocycle
Benzene derivatives
Imine
Antioxidant
Diphenols
In vitro
Radical scavenger
Free radical
Aldimine
Organic pigment
Betalain
Structure activity relation
Medium effect
Six membered ring
Phenols
pH
Betaxanthine
Chemical synthesis
Hemisynthesis
Language English
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Snippet Free radical scavenging compounds play important roles as health-protecting factors. Betalains are natural water-soluble pigments present in most plant...
Free radical scavenging compounds play important roles as health- protecting factors. Betalains are natural water-soluble pigments present in most plant...
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SubjectTerms antioxidant activity
Antioxidants
Antioxidants - chemistry
Antioxidants - isolation & purification
Antioxidants - pharmacology
betalains
Betalains - chemistry
Betalains - isolation & purification
Betalains - pharmacology
betaxanthins
Biological and medical sciences
Caryophyllaceae
Caryophyllaceae - chemistry
Caryophyllales
chemical structure
chemistry
Chemistry, Medicinal
chromatography
Flowers
Flowers - chemistry
free radical scavengers
Free Radical Scavengers - chemistry
Free Radical Scavengers - isolation & purification
Free Radical Scavengers - pharmacology
General and cellular metabolism. Vitamins
Hydrogen-Ion Concentration
isolation & purification
Life Sciences & Biomedicine
mass spectrometry
Medical sciences
Molecular Structure
pharmacology
Pharmacology & Pharmacy
Pharmacology. Drug treatments
phenolic compounds
Phenols
Phenols - chemistry
Phenols - pharmacology
physiology
Pigments, Biological
Pigments, Biological - physiology
plant pigments
Plant Sciences
Plants, Medicinal
Plants, Medicinal - chemistry
Science & Technology
spectroscopy
Structure-Activity Relationship
structure-activity relationships
Title The Role of Phenolic Hydroxy Groups in the Free Radical Scavenging Activity of Betalains
URI http://dx.doi.org/10.1021/np900131r
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https://www.ncbi.nlm.nih.gov/pubmed/19456119
https://www.proquest.com/docview/46360492
https://www.proquest.com/docview/67421003
https://www.proquest.com/docview/771910159
Volume 72
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