Effect of Phytocompounds from the Heartwood of Acacia confusa on Inflammatory Mediator Production
Acacia confusa Merr. (Leguminosae) is traditionally used as a medicinal plant in Taiwan. In the present study, anti-inflammatory activity of extracts from the heartwood of A. confusa were investigated for the first time. Results demonstrated that ethanolic extracts of A. confusa heartwood strongly s...
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| Veröffentlicht in: | Journal of agricultural and food chemistry 2008-03, Vol.56 (5), p.1567-1573 |
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| container_title | Journal of agricultural and food chemistry |
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| creator | Wu, Jyh-Horng Tung, Yu-Tang Chien, Shih-Chang Wang, Sheng-Yang Kuo, Yueh-Hsiung Shyur, Lie-Fen Chang, Shang-Tzen |
| description | Acacia confusa Merr. (Leguminosae) is traditionally used as a medicinal plant in Taiwan. In the present study, anti-inflammatory activity of extracts from the heartwood of A. confusa were investigated for the first time. Results demonstrated that ethanolic extracts of A. confusa heartwood strongly suppressed NO production in lipopolysaccharide (LPS)-activated RAW 264.7 macrophages. Among all fractions derived from ethanolic extracts, the EtOAc fraction exhibited the best inhibitory activity. Following column chromatography and reverse-phase high-performance liquid chromatography, 13 specific phytocompounds including 5 new flavonoids (i.e., 7,8,3′,4′-tetrahydroxy-4-methoxyflavan-3-ol, 7,8,3′,4′-tetrahydroxyflavone, 7,8,3′-trihydroxy-3,4′-dimethoxyflavone, 7,3′,4′-trihydroxyflavone, and 7,3′,4′-trihydroxy-3-methoxyflavone) were isolated and identified from the EtOAc fraction. In addition, melanoxetin (3,7,8,3′,4′-pentahydroxyflavone), a major compound in the EtOAc fraction, markedly suppressed LPS-induced NO and prostaglandin E2 (PGE2) production. Moreover, melanoxetin completely suppressed gene expression of inducible NO synthase (iNOS) and cyclooxygenase-2 (COX-2) at 50 and 100 µM, respectively. This is the first report to identify the inhibitory bioactivities of melanoxetin on iNOS and COX-2. |
| doi_str_mv | 10.1021/jf072922s |
| format | Article |
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(Leguminosae) is traditionally used as a medicinal plant in Taiwan. In the present study, anti-inflammatory activity of extracts from the heartwood of A. confusa were investigated for the first time. Results demonstrated that ethanolic extracts of A. confusa heartwood strongly suppressed NO production in lipopolysaccharide (LPS)-activated RAW 264.7 macrophages. Among all fractions derived from ethanolic extracts, the EtOAc fraction exhibited the best inhibitory activity. Following column chromatography and reverse-phase high-performance liquid chromatography, 13 specific phytocompounds including 5 new flavonoids (i.e., 7,8,3′,4′-tetrahydroxy-4-methoxyflavan-3-ol, 7,8,3′,4′-tetrahydroxyflavone, 7,8,3′-trihydroxy-3,4′-dimethoxyflavone, 7,3′,4′-trihydroxyflavone, and 7,3′,4′-trihydroxy-3-methoxyflavone) were isolated and identified from the EtOAc fraction. In addition, melanoxetin (3,7,8,3′,4′-pentahydroxyflavone), a major compound in the EtOAc fraction, markedly suppressed LPS-induced NO and prostaglandin E2 (PGE2) production. Moreover, melanoxetin completely suppressed gene expression of inducible NO synthase (iNOS) and cyclooxygenase-2 (COX-2) at 50 and 100 µM, respectively. This is the first report to identify the inhibitory bioactivities of melanoxetin on iNOS and COX-2.</description><identifier>ISSN: 0021-8561</identifier><identifier>EISSN: 1520-5118</identifier><identifier>DOI: 10.1021/jf072922s</identifier><identifier>PMID: 18254591</identifier><identifier>CODEN: JAFCAU</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Acacia - chemistry ; Acacia confusa ; Animals ; Anti-Inflammatory Agents - analysis ; Anti-Inflammatory Agents - isolation & purification ; Anti-Inflammatory Agents - pharmacology ; Bioactive Constituents ; Biological and medical sciences ; Cell Line ; chemical analysis ; chemical composition ; Chromatography, High Pressure Liquid - methods ; Cyclooxygenase 2 - metabolism ; Cyclooxygenase 2 Inhibitors - pharmacology ; cyclooxygenase-2 ; Dinoprostone - antagonists & inhibitors ; Dinoprostone - biosynthesis ; flavonoids ; Flavonoids - analysis ; Food industries ; Fundamental and applied biological sciences. Psychology ; heartwood ; Humans ; inducible nitric oxide synthase ; inflammation ; Lipopolysaccharides - pharmacology ; Macrophages - drug effects ; Macrophages - enzymology ; medicinal plants ; melanoxetin ; nitric oxide ; Nitric Oxide - antagonists & inhibitors ; Nitric Oxide - metabolism ; Nitric Oxide Synthase Type II - genetics ; Nitric Oxide Synthase Type II - metabolism ; Oxazoles - pharmacology ; phytochemicals ; plant extracts ; Plant Extracts - analysis ; Plant Extracts - isolation & purification ; Plant Extracts - pharmacology ; prostaglandin E2 ; reactive oxygen species</subject><ispartof>Journal of agricultural and food chemistry, 2008-03, Vol.56 (5), p.1567-1573</ispartof><rights>Copyright © 2008 American Chemical Society</rights><rights>2008 INIST-CNRS</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a506t-4fd9aa941e831446084c953b4fe410395f7df81a6a76b368aa447ae6186ba66d3</citedby><cites>FETCH-LOGICAL-a506t-4fd9aa941e831446084c953b4fe410395f7df81a6a76b368aa447ae6186ba66d3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jf072922s$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jf072922s$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=20168024$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/18254591$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Wu, Jyh-Horng</creatorcontrib><creatorcontrib>Tung, Yu-Tang</creatorcontrib><creatorcontrib>Chien, Shih-Chang</creatorcontrib><creatorcontrib>Wang, Sheng-Yang</creatorcontrib><creatorcontrib>Kuo, Yueh-Hsiung</creatorcontrib><creatorcontrib>Shyur, Lie-Fen</creatorcontrib><creatorcontrib>Chang, Shang-Tzen</creatorcontrib><title>Effect of Phytocompounds from the Heartwood of Acacia confusa on Inflammatory Mediator Production</title><title>Journal of agricultural and food chemistry</title><addtitle>J. Agric. Food Chem</addtitle><description>Acacia confusa Merr. (Leguminosae) is traditionally used as a medicinal plant in Taiwan. In the present study, anti-inflammatory activity of extracts from the heartwood of A. confusa were investigated for the first time. Results demonstrated that ethanolic extracts of A. confusa heartwood strongly suppressed NO production in lipopolysaccharide (LPS)-activated RAW 264.7 macrophages. Among all fractions derived from ethanolic extracts, the EtOAc fraction exhibited the best inhibitory activity. Following column chromatography and reverse-phase high-performance liquid chromatography, 13 specific phytocompounds including 5 new flavonoids (i.e., 7,8,3′,4′-tetrahydroxy-4-methoxyflavan-3-ol, 7,8,3′,4′-tetrahydroxyflavone, 7,8,3′-trihydroxy-3,4′-dimethoxyflavone, 7,3′,4′-trihydroxyflavone, and 7,3′,4′-trihydroxy-3-methoxyflavone) were isolated and identified from the EtOAc fraction. In addition, melanoxetin (3,7,8,3′,4′-pentahydroxyflavone), a major compound in the EtOAc fraction, markedly suppressed LPS-induced NO and prostaglandin E2 (PGE2) production. Moreover, melanoxetin completely suppressed gene expression of inducible NO synthase (iNOS) and cyclooxygenase-2 (COX-2) at 50 and 100 µM, respectively. This is the first report to identify the inhibitory bioactivities of melanoxetin on iNOS and COX-2.</description><subject>Acacia - chemistry</subject><subject>Acacia confusa</subject><subject>Animals</subject><subject>Anti-Inflammatory Agents - analysis</subject><subject>Anti-Inflammatory Agents - isolation & purification</subject><subject>Anti-Inflammatory Agents - pharmacology</subject><subject>Bioactive Constituents</subject><subject>Biological and medical sciences</subject><subject>Cell Line</subject><subject>chemical analysis</subject><subject>chemical composition</subject><subject>Chromatography, High Pressure Liquid - methods</subject><subject>Cyclooxygenase 2 - metabolism</subject><subject>Cyclooxygenase 2 Inhibitors - pharmacology</subject><subject>cyclooxygenase-2</subject><subject>Dinoprostone - antagonists & inhibitors</subject><subject>Dinoprostone - biosynthesis</subject><subject>flavonoids</subject><subject>Flavonoids - analysis</subject><subject>Food industries</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>heartwood</subject><subject>Humans</subject><subject>inducible nitric oxide synthase</subject><subject>inflammation</subject><subject>Lipopolysaccharides - pharmacology</subject><subject>Macrophages - drug effects</subject><subject>Macrophages - enzymology</subject><subject>medicinal plants</subject><subject>melanoxetin</subject><subject>nitric oxide</subject><subject>Nitric Oxide - antagonists & inhibitors</subject><subject>Nitric Oxide - metabolism</subject><subject>Nitric Oxide Synthase Type II - genetics</subject><subject>Nitric Oxide Synthase Type II - metabolism</subject><subject>Oxazoles - pharmacology</subject><subject>phytochemicals</subject><subject>plant extracts</subject><subject>Plant Extracts - analysis</subject><subject>Plant Extracts - isolation & purification</subject><subject>Plant Extracts - pharmacology</subject><subject>prostaglandin E2</subject><subject>reactive oxygen species</subject><issn>0021-8561</issn><issn>1520-5118</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0ctuEzEUBmALgWgoLHgB8AYkFlPs8X1ZRaWtVNRI6WVpnXhsOmFmnNozgrw9jhKlG1a2dD79lv-D0EdKziip6fd1IKo2dZ1foRkVNakEpfo1mpEyrLSQ9AS9y3lNCNFCkbfohOpacGHoDMFFCN6NOAa8eNqO0cV-E6ehyTik2OPxyeMrD2n8E2OzQ-cOXAvYxSFMGXAc8PUQOuh7GGPa4p--aXc3vEixmdzYxuE9ehOgy_7D4TxF9z8u7uZX1c3t5fX8_KYCQeRY8dAYAMOp14xyLonmzgi24sFzSpgRQTVBU5Cg5IpJDcC5Ai-pliuQsmGn6Os-d5Pi8-TzaPs2O991MPg4ZasIk8QwVeC3PXQp5px8sJvU9pC2lhK769Me-yz20yF0WvW-eZGHAgv4cgCQHXQhweDafHQ1oVKTmhdX7V2bR__3OIf020rFlLB3i6V9pPOH5SWbW1n8570PEC38SiXzflnSWNmhNMrIl5fBZbuOUxpKu__5wj_nXKF8</recordid><startdate>20080312</startdate><enddate>20080312</enddate><creator>Wu, Jyh-Horng</creator><creator>Tung, Yu-Tang</creator><creator>Chien, Shih-Chang</creator><creator>Wang, Sheng-Yang</creator><creator>Kuo, Yueh-Hsiung</creator><creator>Shyur, Lie-Fen</creator><creator>Chang, Shang-Tzen</creator><general>American Chemical Society</general><scope>FBQ</scope><scope>BSCLL</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20080312</creationdate><title>Effect of Phytocompounds from the Heartwood of Acacia confusa on Inflammatory Mediator Production</title><author>Wu, Jyh-Horng ; Tung, Yu-Tang ; Chien, Shih-Chang ; Wang, Sheng-Yang ; Kuo, Yueh-Hsiung ; Shyur, Lie-Fen ; Chang, Shang-Tzen</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a506t-4fd9aa941e831446084c953b4fe410395f7df81a6a76b368aa447ae6186ba66d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>Acacia - chemistry</topic><topic>Acacia confusa</topic><topic>Animals</topic><topic>Anti-Inflammatory Agents - analysis</topic><topic>Anti-Inflammatory Agents - isolation & purification</topic><topic>Anti-Inflammatory Agents - pharmacology</topic><topic>Bioactive Constituents</topic><topic>Biological and medical sciences</topic><topic>Cell Line</topic><topic>chemical analysis</topic><topic>chemical composition</topic><topic>Chromatography, High Pressure Liquid - methods</topic><topic>Cyclooxygenase 2 - metabolism</topic><topic>Cyclooxygenase 2 Inhibitors - pharmacology</topic><topic>cyclooxygenase-2</topic><topic>Dinoprostone - antagonists & inhibitors</topic><topic>Dinoprostone - biosynthesis</topic><topic>flavonoids</topic><topic>Flavonoids - analysis</topic><topic>Food industries</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>heartwood</topic><topic>Humans</topic><topic>inducible nitric oxide synthase</topic><topic>inflammation</topic><topic>Lipopolysaccharides - pharmacology</topic><topic>Macrophages - drug effects</topic><topic>Macrophages - enzymology</topic><topic>medicinal plants</topic><topic>melanoxetin</topic><topic>nitric oxide</topic><topic>Nitric Oxide - antagonists & inhibitors</topic><topic>Nitric Oxide - metabolism</topic><topic>Nitric Oxide Synthase Type II - genetics</topic><topic>Nitric Oxide Synthase Type II - metabolism</topic><topic>Oxazoles - pharmacology</topic><topic>phytochemicals</topic><topic>plant extracts</topic><topic>Plant Extracts - analysis</topic><topic>Plant Extracts - isolation & purification</topic><topic>Plant Extracts - pharmacology</topic><topic>prostaglandin E2</topic><topic>reactive oxygen species</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wu, Jyh-Horng</creatorcontrib><creatorcontrib>Tung, Yu-Tang</creatorcontrib><creatorcontrib>Chien, Shih-Chang</creatorcontrib><creatorcontrib>Wang, Sheng-Yang</creatorcontrib><creatorcontrib>Kuo, Yueh-Hsiung</creatorcontrib><creatorcontrib>Shyur, Lie-Fen</creatorcontrib><creatorcontrib>Chang, Shang-Tzen</creatorcontrib><collection>AGRIS</collection><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of agricultural and food chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wu, Jyh-Horng</au><au>Tung, Yu-Tang</au><au>Chien, Shih-Chang</au><au>Wang, Sheng-Yang</au><au>Kuo, Yueh-Hsiung</au><au>Shyur, Lie-Fen</au><au>Chang, Shang-Tzen</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Effect of Phytocompounds from the Heartwood of Acacia confusa on Inflammatory Mediator Production</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>2008-03-12</date><risdate>2008</risdate><volume>56</volume><issue>5</issue><spage>1567</spage><epage>1573</epage><pages>1567-1573</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><coden>JAFCAU</coden><abstract>Acacia confusa Merr. (Leguminosae) is traditionally used as a medicinal plant in Taiwan. In the present study, anti-inflammatory activity of extracts from the heartwood of A. confusa were investigated for the first time. Results demonstrated that ethanolic extracts of A. confusa heartwood strongly suppressed NO production in lipopolysaccharide (LPS)-activated RAW 264.7 macrophages. Among all fractions derived from ethanolic extracts, the EtOAc fraction exhibited the best inhibitory activity. Following column chromatography and reverse-phase high-performance liquid chromatography, 13 specific phytocompounds including 5 new flavonoids (i.e., 7,8,3′,4′-tetrahydroxy-4-methoxyflavan-3-ol, 7,8,3′,4′-tetrahydroxyflavone, 7,8,3′-trihydroxy-3,4′-dimethoxyflavone, 7,3′,4′-trihydroxyflavone, and 7,3′,4′-trihydroxy-3-methoxyflavone) were isolated and identified from the EtOAc fraction. In addition, melanoxetin (3,7,8,3′,4′-pentahydroxyflavone), a major compound in the EtOAc fraction, markedly suppressed LPS-induced NO and prostaglandin E2 (PGE2) production. Moreover, melanoxetin completely suppressed gene expression of inducible NO synthase (iNOS) and cyclooxygenase-2 (COX-2) at 50 and 100 µM, respectively. This is the first report to identify the inhibitory bioactivities of melanoxetin on iNOS and COX-2.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>18254591</pmid><doi>10.1021/jf072922s</doi><tpages>7</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | Acacia - chemistry Acacia confusa Animals Anti-Inflammatory Agents - analysis Anti-Inflammatory Agents - isolation & purification Anti-Inflammatory Agents - pharmacology Bioactive Constituents Biological and medical sciences Cell Line chemical analysis chemical composition Chromatography, High Pressure Liquid - methods Cyclooxygenase 2 - metabolism Cyclooxygenase 2 Inhibitors - pharmacology cyclooxygenase-2 Dinoprostone - antagonists & inhibitors Dinoprostone - biosynthesis flavonoids Flavonoids - analysis Food industries Fundamental and applied biological sciences. Psychology heartwood Humans inducible nitric oxide synthase inflammation Lipopolysaccharides - pharmacology Macrophages - drug effects Macrophages - enzymology medicinal plants melanoxetin nitric oxide Nitric Oxide - antagonists & inhibitors Nitric Oxide - metabolism Nitric Oxide Synthase Type II - genetics Nitric Oxide Synthase Type II - metabolism Oxazoles - pharmacology phytochemicals plant extracts Plant Extracts - analysis Plant Extracts - isolation & purification Plant Extracts - pharmacology prostaglandin E2 reactive oxygen species |
| title | Effect of Phytocompounds from the Heartwood of Acacia confusa on Inflammatory Mediator Production |
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