Antioxidant properties of hydroxycinnamic acids: a review of structure- activity relationships.
Identifieur interne : 000518 ( PubMed/Corpus ); précédent : 000517; suivant : 000519Antioxidant properties of hydroxycinnamic acids: a review of structure- activity relationships.
Auteurs : N. Razzaghi-Asl ; J. Garrido ; H. Khazraei ; F. Borges ; O. FiruziSource :
- Current medicinal chemistry [ 1875-533X ] ; 2013.
English descriptors
- KwdEn :
- MESH :
- chemical , chemistry : Antioxidants, Coumaric Acids.
- chemical , metabolism : Reactive Oxygen Species.
- chemical , pharmacology : Antioxidants, Coumaric Acids.
- drug effects : Oxidative Stress.
- physiology : Oxidative Stress.
- Oxidation-Reduction, Structure-Activity Relationship.
Abstract
Hydroxycinnamic acids (HCAs) are important phytochemicals possessing significant biological properties. Several investigators have studied in vitro antioxidant activity of HCAs in detail. In this review, we have gathered the studies focused on the structure-activity relationships (SARs) of these compounds that have used medicinal chemistry to generate more potent antioxidant molecules. Most of the reports indicated that the presence of an unsaturated bond on the side chain of HCAs is vital to their activity. The structural features that were reported to be of importance to the antioxidant activity were categorized as follows: modifications of the aromatic ring, which include alterations in the number and position of hydroxy groups and insertion of electron donating or withdrawing moieties as well as modifications of the carboxylic function that include esterification and amidation process. Furthermore, reports that have addressed the influence of physicochemical properties including redox potential, lipid solubility and dissociation constant on the antioxidant activity were also summarized. Finally, the pro-oxidant effect of HCAs in some test systems was addressed. Most of the investigations concluded that the presence of ortho-dihydroxy phenyl group (catechol moiety) is of significant importance to the antioxidant activity, while, the presence of three hydroxy groups does not necessarily improve the activity. Optimization of the structure of molecular leads is an important task of modern medicinal chemistry and its accomplishment relies on the careful assessment of SARs. SAR studies on HCAs can identify the most successful antioxidants that could be useful for management of oxidative stress-related diseases.
DOI: 10.2174/09298673113209990141
PubMed: 23834166
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pubmed:23834166Le document en format XML
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Firuzi</name></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="2013">2013</date><idno type="RBID">pubmed:23834166</idno><idno type="pmid">23834166</idno><idno type="doi">10.2174/09298673113209990141</idno><idno type="wicri:Area/PubMed/Corpus">000518</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Corpus" wicri:corpus="PubMed">000518</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en">Antioxidant properties of hydroxycinnamic acids: a review of structure- activity relationships.</title><author><name sortKey="Razzaghi Asl, N" sort="Razzaghi Asl, N" uniqKey="Razzaghi Asl N" first="N" last="Razzaghi-Asl">N. Razzaghi-Asl</name><affiliation><nlm:affiliation>Medicinal and Natural Products Chemistry Research Center, Shiraz University of Medical Sciences, PO Box 71345-3388, Shiraz, Iran. firuzio@sums.ac.ir.</nlm:affiliation></affiliation></author><author><name sortKey="Garrido, J" sort="Garrido, J" uniqKey="Garrido J" first="J" last="Garrido">J. Garrido</name></author><author><name sortKey="Khazraei, H" sort="Khazraei, H" uniqKey="Khazraei H" first="H" last="Khazraei">H. Khazraei</name></author><author><name sortKey="Borges, F" sort="Borges, F" uniqKey="Borges F" first="F" last="Borges">F. Borges</name></author><author><name sortKey="Firuzi, O" sort="Firuzi, O" uniqKey="Firuzi O" first="O" last="Firuzi">O. Firuzi</name></author></analytic><series><title level="j">Current medicinal chemistry</title><idno type="eISSN">1875-533X</idno><imprint><date when="2013" type="published">2013</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Antioxidants (chemistry)</term><term>Antioxidants (pharmacology)</term><term>Coumaric Acids (chemistry)</term><term>Coumaric Acids (pharmacology)</term><term>Oxidation-Reduction</term><term>Oxidative Stress (drug effects)</term><term>Oxidative Stress (physiology)</term><term>Reactive Oxygen Species (metabolism)</term><term>Structure-Activity Relationship</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Antioxidants</term><term>Coumaric Acids</term></keywords><keywords scheme="MESH" type="chemical" qualifier="metabolism" xml:lang="en"><term>Reactive Oxygen Species</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Antioxidants</term><term>Coumaric Acids</term></keywords><keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>Oxidative Stress</term></keywords><keywords scheme="MESH" qualifier="physiology" xml:lang="en"><term>Oxidative Stress</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Oxidation-Reduction</term><term>Structure-Activity Relationship</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Hydroxycinnamic acids (HCAs) are important phytochemicals possessing significant biological properties. Several investigators have studied in vitro antioxidant activity of HCAs in detail. In this review, we have gathered the studies focused on the structure-activity relationships (SARs) of these compounds that have used medicinal chemistry to generate more potent antioxidant molecules. Most of the reports indicated that the presence of an unsaturated bond on the side chain of HCAs is vital to their activity. The structural features that were reported to be of importance to the antioxidant activity were categorized as follows: modifications of the aromatic ring, which include alterations in the number and position of hydroxy groups and insertion of electron donating or withdrawing moieties as well as modifications of the carboxylic function that include esterification and amidation process. Furthermore, reports that have addressed the influence of physicochemical properties including redox potential, lipid solubility and dissociation constant on the antioxidant activity were also summarized. Finally, the pro-oxidant effect of HCAs in some test systems was addressed. Most of the investigations concluded that the presence of ortho-dihydroxy phenyl group (catechol moiety) is of significant importance to the antioxidant activity, while, the presence of three hydroxy groups does not necessarily improve the activity. Optimization of the structure of molecular leads is an important task of modern medicinal chemistry and its accomplishment relies on the careful assessment of SARs. SAR studies on HCAs can identify the most successful antioxidants that could be useful for management of oxidative stress-related diseases. </div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">23834166</PMID><DateCompleted><Year>2014</Year><Month>07</Month><Day>22</Day></DateCompleted><DateRevised><Year>2019</Year><Month>08</Month><Day>23</Day></DateRevised><Article PubModel="Print"><Journal><ISSN IssnType="Electronic">1875-533X</ISSN><JournalIssue CitedMedium="Internet"><Volume>20</Volume><Issue>36</Issue><PubDate><Year>2013</Year></PubDate></JournalIssue><Title>Current medicinal chemistry</Title><ISOAbbreviation>Curr. Med. Chem.</ISOAbbreviation></Journal><ArticleTitle>Antioxidant properties of hydroxycinnamic acids: a review of structure- activity relationships.</ArticleTitle><Pagination><MedlinePgn>4436-50</MedlinePgn></Pagination><Abstract><AbstractText>Hydroxycinnamic acids (HCAs) are important phytochemicals possessing significant biological properties. Several investigators have studied in vitro antioxidant activity of HCAs in detail. In this review, we have gathered the studies focused on the structure-activity relationships (SARs) of these compounds that have used medicinal chemistry to generate more potent antioxidant molecules. Most of the reports indicated that the presence of an unsaturated bond on the side chain of HCAs is vital to their activity. The structural features that were reported to be of importance to the antioxidant activity were categorized as follows: modifications of the aromatic ring, which include alterations in the number and position of hydroxy groups and insertion of electron donating or withdrawing moieties as well as modifications of the carboxylic function that include esterification and amidation process. Furthermore, reports that have addressed the influence of physicochemical properties including redox potential, lipid solubility and dissociation constant on the antioxidant activity were also summarized. Finally, the pro-oxidant effect of HCAs in some test systems was addressed. Most of the investigations concluded that the presence of ortho-dihydroxy phenyl group (catechol moiety) is of significant importance to the antioxidant activity, while, the presence of three hydroxy groups does not necessarily improve the activity. Optimization of the structure of molecular leads is an important task of modern medicinal chemistry and its accomplishment relies on the careful assessment of SARs. SAR studies on HCAs can identify the most successful antioxidants that could be useful for management of oxidative stress-related diseases. </AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Razzaghi-Asl</LastName><ForeName>N</ForeName><Initials>N</Initials><AffiliationInfo><Affiliation>Medicinal and Natural Products Chemistry Research Center, Shiraz University of Medical Sciences, PO Box 71345-3388, Shiraz, Iran. firuzio@sums.ac.ir.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Garrido</LastName><ForeName>J</ForeName><Initials>J</Initials></Author><Author ValidYN="Y"><LastName>Khazraei</LastName><ForeName>H</ForeName><Initials>H</Initials></Author><Author ValidYN="Y"><LastName>Borges</LastName><ForeName>F</ForeName><Initials>F</Initials></Author><Author ValidYN="Y"><LastName>Firuzi</LastName><ForeName>O</ForeName><Initials>O</Initials></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType><PublicationType UI="D013485">Research Support, Non-U.S. Gov't</PublicationType><PublicationType UI="D016454">Review</PublicationType></PublicationTypeList></Article><MedlineJournalInfo><Country>United Arab Emirates</Country><MedlineTA>Curr Med Chem</MedlineTA><NlmUniqueID>9440157</NlmUniqueID><ISSNLinking>0929-8673</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D000975">Antioxidants</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D003373">Coumaric Acids</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D017382">Reactive Oxygen Species</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D000975" MajorTopicYN="N">Antioxidants</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName><QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D003373" MajorTopicYN="N">Coumaric Acids</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName><QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D010084" MajorTopicYN="N">Oxidation-Reduction</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D018384" MajorTopicYN="N">Oxidative Stress</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="N">drug effects</QualifierName><QualifierName UI="Q000502" MajorTopicYN="N">physiology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D017382" MajorTopicYN="N">Reactive Oxygen Species</DescriptorName><QualifierName UI="Q000378" MajorTopicYN="N">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D013329" MajorTopicYN="N">Structure-Activity Relationship</DescriptorName></MeshHeading></MeshHeadingList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2012</Year><Month>10</Month><Day>23</Day></PubMedPubDate><PubMedPubDate PubStatus="revised"><Year>2013</Year><Month>02</Month><Day>24</Day></PubMedPubDate><PubMedPubDate PubStatus="accepted"><Year>2013</Year><Month>03</Month><Day>10</Day></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2013</Year><Month>7</Month><Day>10</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2013</Year><Month>7</Month><Day>10</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2014</Year><Month>7</Month><Day>23</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">23834166</ArticleId><ArticleId IdType="pii">CMC-EPUB-02-03-07-2013</ArticleId><ArticleId IdType="doi">10.2174/09298673113209990141</ArticleId></ArticleIdList></PubmedData></pubmed></record>Pour manipuler ce document sous Unix (Dilib)
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