Extraction and PTP1B inhibitory activity of bromophenols from the marine red alga Symphyocladia latiuscula
Previously, we had characterized several structurally interesting brominated phenols from the marine red alga Symphyocladia latiuscula collected from various sites. However, Phytochemical investigations on this species collected from the Weihai coastline of Shandong Province remains blank. Therefore...
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| Veröffentlicht in: | Chinese journal of oceanology and limnology 2011-05, Vol.29 (3), p.686-690 |
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| creator | 刘旭 李晓明 高立信 崔传明 李春顺 李佳 王斌贵 |
| description | Previously, we had characterized several structurally interesting brominated phenols from the marine red alga Symphyocladia latiuscula collected from various sites. However, Phytochemical investigations on this species collected from the Weihai coastline of Shandong Province remains blank. Therefore, we characterized the chemical constituents of individuals of this species collected from the region. Eight bromophenols were isolated and identified. Using detailed spectroscopic techniques and comparisons with published data, these compounds were identified as 2,3-dibromo-4,5-dihydroxybenzyl methyl ether （1）, 3,5-dibromo-4-hydroxybenzoic acid （2）, 2,3,6-tribromo-4,5-dihydroxymethylbenzene （3）, 2,3,6-tribromo-4,5-dihydroxybenzaldehyde （4）, 2,3,6-tribromo-4,5-dihydroxybenzyl methyl ether （5）, bis（2,3,6-tribromo-4,5-dihydroxyphenyl）methane （6）, 1,2-bis（2,3,6-tribromo-4,5-dihydroxyphenyl）-ethane （7）, and 1-（2,3,6-tribromo-4,5-dihydroxybenzyl）-pyrrolidin-2-one （8）, Among these compounds, 1 and 2 were isolated for the first time from S. latiuscula. Each compound was evaluated on the ability to inhibit protein tyrosine phosphatase 1B （PTP1B）, which is a potential therapeutic target in the treatment of type 2 diabetes. Bromophenols 5, 6, and 7 showed strong activities with IC50 values of 3.9, 4.3, and 3.5 μmol/L, respectively. This study provides further evidence that bromophenols are predominant among the chemical constituents of Symphyocladia, and that some of these compounds may be candidates for the development of anti-diabetes drugs. |
| doi_str_mv | 10.1007/s00343-011-0136-1 |
| format | Article |
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However, Phytochemical investigations on this species collected from the Weihai coastline of Shandong Province remains blank. Therefore, we characterized the chemical constituents of individuals of this species collected from the region. Eight bromophenols were isolated and identified. Using detailed spectroscopic techniques and comparisons with published data, these compounds were identified as 2,3-dibromo-4,5-dihydroxybenzyl methyl ether （1）, 3,5-dibromo-4-hydroxybenzoic acid （2）, 2,3,6-tribromo-4,5-dihydroxymethylbenzene （3）, 2,3,6-tribromo-4,5-dihydroxybenzaldehyde （4）, 2,3,6-tribromo-4,5-dihydroxybenzyl methyl ether （5）, bis（2,3,6-tribromo-4,5-dihydroxyphenyl）methane （6）, 1,2-bis（2,3,6-tribromo-4,5-dihydroxyphenyl）-ethane （7）, and 1-（2,3,6-tribromo-4,5-dihydroxybenzyl）-pyrrolidin-2-one （8）, Among these compounds, 1 and 2 were isolated for the first time from S. latiuscula. Each compound was evaluated on the ability to inhibit protein tyrosine phosphatase 1B （PTP1B）, which is a potential therapeutic target in the treatment of type 2 diabetes. Bromophenols 5, 6, and 7 showed strong activities with IC50 values of 3.9, 4.3, and 3.5 μmol/L, respectively. This study provides further evidence that bromophenols are predominant among the chemical constituents of Symphyocladia, and that some of these compounds may be candidates for the development of anti-diabetes drugs.</description><identifier>ISSN: 0254-4059</identifier><identifier>ISSN: 2096-5508</identifier><identifier>EISSN: 1993-5005</identifier><identifier>EISSN: 2523-3521</identifier><identifier>DOI: 10.1007/s00343-011-0136-1</identifier><language>eng</language><publisher>Heidelberg: SP Science Press</publisher><subject>Algae ; Bromination ; Constituents ; Diabetes ; Diabetes mellitus (non-insulin dependent) ; Drug development ; Earth and Environmental Science ; Earth Sciences ; Ethane ; Marine ; Marine biology ; Oceanography ; p-Hydroxybenzoic acid ; Pharmacology ; Phenols ; Phosphatase ; Protein-tyrosine-phosphatase ; Proteins ; R&D ; Research & development ; Spectroscopic techniques ; Symphyocladia latiuscula ; Therapeutic targets ; Tyrosine ; 二羟基苯基 ; 二羟基苯甲醛 ; 化学成分特征 ; 抑制活性 ; 提取 ; 植物化学物质 ; 海洋红藻 ; 蛋白酪氨酸磷酸酶</subject><ispartof>Chinese journal of oceanology and limnology, 2011-05, Vol.29 (3), p.686-690</ispartof><rights>Chinese Society for Oceanology and Limnology, Science Press and Springer Berlin Heidelberg 2011</rights><rights>Chinese Society for Oceanology and Limnology, Science Press and Springer Berlin Heidelberg 2011.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c373t-2e937f66e39d1477a8c0d4b24a6e587487729670f8df3045050f1c0d0ebd8e093</citedby><cites>FETCH-LOGICAL-c373t-2e937f66e39d1477a8c0d4b24a6e587487729670f8df3045050f1c0d0ebd8e093</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Uhttp://image.cqvip.com/vip1000/qk/84119X/84119X.jpg</thumbnail><linktopdf>$$Uhttps://www.proquest.com/docview/866477011/fulltextPDF?pq-origsite=primo$$EPDF$$P50$$Gproquest$$H</linktopdf><linktohtml>$$Uhttps://www.proquest.com/docview/866477011?pq-origsite=primo$$EHTML$$P50$$Gproquest$$H</linktohtml><link.rule.ids>314,780,784,21388,21389,21390,21391,23256,27924,27925,33530,33703,33744,34005,34314,43659,43787,43805,43953,44067,64385,64389,72469,74104,74283,74302,74473,74590</link.rule.ids></links><search><creatorcontrib>刘旭 李晓明 高立信 崔传明 李春顺 李佳 王斌贵</creatorcontrib><title>Extraction and PTP1B inhibitory activity of bromophenols from the marine red alga Symphyocladia latiuscula</title><title>Chinese journal of oceanology and limnology</title><addtitle>Chin. J. Ocean. Limnol</addtitle><addtitle>Chinese Journal of Oceanology and Limnology</addtitle><description>Previously, we had characterized several structurally interesting brominated phenols from the marine red alga Symphyocladia latiuscula collected from various sites. However, Phytochemical investigations on this species collected from the Weihai coastline of Shandong Province remains blank. Therefore, we characterized the chemical constituents of individuals of this species collected from the region. Eight bromophenols were isolated and identified. Using detailed spectroscopic techniques and comparisons with published data, these compounds were identified as 2,3-dibromo-4,5-dihydroxybenzyl methyl ether （1）, 3,5-dibromo-4-hydroxybenzoic acid （2）, 2,3,6-tribromo-4,5-dihydroxymethylbenzene （3）, 2,3,6-tribromo-4,5-dihydroxybenzaldehyde （4）, 2,3,6-tribromo-4,5-dihydroxybenzyl methyl ether （5）, bis（2,3,6-tribromo-4,5-dihydroxyphenyl）methane （6）, 1,2-bis（2,3,6-tribromo-4,5-dihydroxyphenyl）-ethane （7）, and 1-（2,3,6-tribromo-4,5-dihydroxybenzyl）-pyrrolidin-2-one （8）, Among these compounds, 1 and 2 were isolated for the first time from S. latiuscula. Each compound was evaluated on the ability to inhibit protein tyrosine phosphatase 1B （PTP1B）, which is a potential therapeutic target in the treatment of type 2 diabetes. Bromophenols 5, 6, and 7 showed strong activities with IC50 values of 3.9, 4.3, and 3.5 μmol/L, respectively. This study provides further evidence that bromophenols are predominant among the chemical constituents of Symphyocladia, and that some of these compounds may be candidates for the development of anti-diabetes drugs.</description><subject>Algae</subject><subject>Bromination</subject><subject>Constituents</subject><subject>Diabetes</subject><subject>Diabetes mellitus (non-insulin dependent)</subject><subject>Drug development</subject><subject>Earth and Environmental Science</subject><subject>Earth Sciences</subject><subject>Ethane</subject><subject>Marine</subject><subject>Marine biology</subject><subject>Oceanography</subject><subject>p-Hydroxybenzoic acid</subject><subject>Pharmacology</subject><subject>Phenols</subject><subject>Phosphatase</subject><subject>Protein-tyrosine-phosphatase</subject><subject>Proteins</subject><subject>R&D</subject><subject>Research & development</subject><subject>Spectroscopic techniques</subject><subject>Symphyocladia latiuscula</subject><subject>Therapeutic targets</subject><subject>Tyrosine</subject><subject>二羟基苯基</subject><subject>二羟基苯甲醛</subject><subject>化学成分特征</subject><subject>抑制活性</subject><subject>提取</subject><subject>植物化学物质</subject><subject>海洋红藻</subject><subject>蛋白酪氨酸磷酸酶</subject><issn>0254-4059</issn><issn>2096-5508</issn><issn>1993-5005</issn><issn>2523-3521</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>ABUWG</sourceid><sourceid>AFKRA</sourceid><sourceid>AZQEC</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><sourceid>GNUQQ</sourceid><recordid>eNp9kE9LxDAQxYMouK5-AG_Ri6fqpEmT5qjiPxAUXM8h26bbLN1kN2nFfnuzrCh48DCEIb83b-YhdErgkgCIqwhAGc2AkFSUZ2QPTYiUNCsAin00gbxgGYNCHqKjGJeJlgzkBC3vPvugq956h7Wr8evsldxg61o7t70PI97-fdh-xL7B8-BXft0a57uIm9TgvjV4pYN1BgdTY90tNH4bV-t29FWna6txp3s7xGro9DE6aHQXzcn3O0Xv93ez28fs-eXh6fb6OauooH2WG0lFw7mhsiZMCF1WULN5zjQ3RSlYKUQuuYCmrBsKrIACGpIQMPO6NCDpFF3s5q6D3wwm9mplY2W6Tjvjh6hKKQmjOSeJPP9DLv0QXFpOlZwn7xRngsgOqoKPMZhGrYNNN4-KgNpmr3bZqwSrbfZqq8l3mphYtzDhd_B_orNvo9a7xSbpfpyoELxIl9IvdFiRxw</recordid><startdate>20110501</startdate><enddate>20110501</enddate><creator>刘旭 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Symphyocladia latiuscula</title><author>刘旭 李晓明 高立信 崔传明 李春顺 李佳 王斌贵</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c373t-2e937f66e39d1477a8c0d4b24a6e587487729670f8df3045050f1c0d0ebd8e093</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Algae</topic><topic>Bromination</topic><topic>Constituents</topic><topic>Diabetes</topic><topic>Diabetes mellitus (non-insulin dependent)</topic><topic>Drug development</topic><topic>Earth and Environmental Science</topic><topic>Earth Sciences</topic><topic>Ethane</topic><topic>Marine</topic><topic>Marine biology</topic><topic>Oceanography</topic><topic>p-Hydroxybenzoic acid</topic><topic>Pharmacology</topic><topic>Phenols</topic><topic>Phosphatase</topic><topic>Protein-tyrosine-phosphatase</topic><topic>Proteins</topic><topic>R&D</topic><topic>Research & development</topic><topic>Spectroscopic techniques</topic><topic>Symphyocladia 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journal of oceanology and limnology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>刘旭 李晓明 高立信 崔传明 李春顺 李佳 王斌贵</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Extraction and PTP1B inhibitory activity of bromophenols from the marine red alga Symphyocladia latiuscula</atitle><jtitle>Chinese journal of oceanology and limnology</jtitle><stitle>Chin. J. Ocean. Limnol</stitle><addtitle>Chinese Journal of Oceanology and Limnology</addtitle><date>2011-05-01</date><risdate>2011</risdate><volume>29</volume><issue>3</issue><spage>686</spage><epage>690</epage><pages>686-690</pages><issn>0254-4059</issn><issn>2096-5508</issn><eissn>1993-5005</eissn><eissn>2523-3521</eissn><abstract>Previously, we had characterized several structurally interesting brominated phenols from the marine red alga Symphyocladia latiuscula collected from various sites. However, Phytochemical investigations on this species collected from the Weihai coastline of Shandong Province remains blank. Therefore, we characterized the chemical constituents of individuals of this species collected from the region. Eight bromophenols were isolated and identified. Using detailed spectroscopic techniques and comparisons with published data, these compounds were identified as 2,3-dibromo-4,5-dihydroxybenzyl methyl ether （1）, 3,5-dibromo-4-hydroxybenzoic acid （2）, 2,3,6-tribromo-4,5-dihydroxymethylbenzene （3）, 2,3,6-tribromo-4,5-dihydroxybenzaldehyde （4）, 2,3,6-tribromo-4,5-dihydroxybenzyl methyl ether （5）, bis（2,3,6-tribromo-4,5-dihydroxyphenyl）methane （6）, 1,2-bis（2,3,6-tribromo-4,5-dihydroxyphenyl）-ethane （7）, and 1-（2,3,6-tribromo-4,5-dihydroxybenzyl）-pyrrolidin-2-one （8）, Among these compounds, 1 and 2 were isolated for the first time from S. latiuscula. Each compound was evaluated on the ability to inhibit protein tyrosine phosphatase 1B （PTP1B）, which is a potential therapeutic target in the treatment of type 2 diabetes. Bromophenols 5, 6, and 7 showed strong activities with IC50 values of 3.9, 4.3, and 3.5 μmol/L, respectively. This study provides further evidence that bromophenols are predominant among the chemical constituents of Symphyocladia, and that some of these compounds may be candidates for the development of anti-diabetes drugs.</abstract><cop>Heidelberg</cop><pub>SP Science Press</pub><doi>10.1007/s00343-011-0136-1</doi><tpages>5</tpages></addata></record> |
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| ispartof | Chinese journal of oceanology and limnology, 2011-05, Vol.29 (3), p.686-690 |
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| subjects | Algae Bromination Constituents Diabetes Diabetes mellitus (non-insulin dependent) Drug development Earth and Environmental Science Earth Sciences Ethane Marine Marine biology Oceanography p-Hydroxybenzoic acid Pharmacology Phenols Phosphatase Protein-tyrosine-phosphatase Proteins R&D Research & development Spectroscopic techniques Symphyocladia latiuscula Therapeutic targets Tyrosine 二羟基苯基 二羟基苯甲醛 化学成分特征 抑制活性 提取 植物化学物质 海洋红藻 蛋白酪氨酸磷酸酶 |
| title | Extraction and PTP1B inhibitory activity of bromophenols from the marine red alga Symphyocladia latiuscula |
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