Schistosomicidal Activity of Dihydrobenzofuran Neolignans
We have evaluated the antischistosomal activity of synthetic dihydrobenzofuran neolignans (DBNs) derived from (±)‐trans‐dehydrodicoumaric acid dimethyl ester (1) and (±)‐trans‐dehydrodiferulic acid dimethyl ester (2) against adult Schistosoma mansoni worms in vitro. Compound 4 ((±)‐trans‐4‐O‐acetyld...
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| Veröffentlicht in: | Chemistry & biodiversity 2018-07, Vol.15 (7), p.e1800134-n/a |
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| creator | Dias, Herbert J. Patrocínio, Andressa B. Pagotti, Mariana C. Fukui, Murilo J. Rodrigues, Vanderlei Magalhães, Lizandra G. Crotti, Antônio E. M. |
| description | We have evaluated the antischistosomal activity of synthetic dihydrobenzofuran neolignans (DBNs) derived from (±)‐trans‐dehydrodicoumaric acid dimethyl ester (1) and (±)‐trans‐dehydrodiferulic acid dimethyl ester (2) against adult Schistosoma mansoni worms in vitro. Compound 4 ((±)‐trans‐4‐O‐acetyldehydrodiferulic acid dimethyl ester) displayed the most promising activity; at 200 μm, it kills 100 ± 0% of worms after 24 h, which resembles the result achieved with praziquantel (positive control) at 1.56 μm. The hydrogenation of the double bond between C7′ and C8′, the introduction of an additional methyl group at C3′, and a double bond between C7 and C8 decreased the schistosomicidal activity of DBNs. On the other hand, the presence of the acetoxy group at C4 played an interesting role in this activity. These results demonstrated the interesting schistosomicidal potential of DBNs, which could be further exploited. |
| doi_str_mv | 10.1002/cbdv.201800134 |
| format | Article |
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M.</creator><creatorcontrib>Dias, Herbert J. ; Patrocínio, Andressa B. ; Pagotti, Mariana C. ; Fukui, Murilo J. ; Rodrigues, Vanderlei ; Magalhães, Lizandra G. ; Crotti, Antônio E. M.</creatorcontrib><description>We have evaluated the antischistosomal activity of synthetic dihydrobenzofuran neolignans (DBNs) derived from (±)‐trans‐dehydrodicoumaric acid dimethyl ester (1) and (±)‐trans‐dehydrodiferulic acid dimethyl ester (2) against adult Schistosoma mansoni worms in vitro. Compound 4 ((±)‐trans‐4‐O‐acetyldehydrodiferulic acid dimethyl ester) displayed the most promising activity; at 200 μm, it kills 100 ± 0% of worms after 24 h, which resembles the result achieved with praziquantel (positive control) at 1.56 μm. The hydrogenation of the double bond between C7′ and C8′, the introduction of an additional methyl group at C3′, and a double bond between C7 and C8 decreased the schistosomicidal activity of DBNs. On the other hand, the presence of the acetoxy group at C4 played an interesting role in this activity. These results demonstrated the interesting schistosomicidal potential of DBNs, which could be further exploited.</description><identifier>ISSN: 1612-1872</identifier><identifier>EISSN: 1612-1880</identifier><identifier>DOI: 10.1002/cbdv.201800134</identifier><identifier>PMID: 29754441</identifier><language>eng</language><publisher>Switzerland: Wiley Subscription Services, Inc</publisher><subject>Acids ; Animals ; benzofuran neolignans ; Dose-Response Relationship, Drug ; Lignans - chemical synthesis ; Lignans - chemistry ; Lignans - pharmacology ; Molecular Structure ; neglected diseases ; oxidative coupling ; phenylpropanoids ; Praziquantel ; Schistosoma mansoni ; Schistosoma mansoni - drug effects ; Schistosomicides - chemical synthesis ; Schistosomicides - chemistry ; Schistosomicides - pharmacology</subject><ispartof>Chemistry & biodiversity, 2018-07, Vol.15 (7), p.e1800134-n/a</ispartof><rights>2018 Wiley‐VHCA AG, Zurich, Switzerland</rights><rights>2018 Wiley-VHCA AG, Zurich, Switzerland.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4394-69e13dd9b08774743b1ba4637fbc896c14a9b4637e62bc3ce6317823f261fcf93</citedby><cites>FETCH-LOGICAL-c4394-69e13dd9b08774743b1ba4637fbc896c14a9b4637e62bc3ce6317823f261fcf93</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fcbdv.201800134$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fcbdv.201800134$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/29754441$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Dias, Herbert J.</creatorcontrib><creatorcontrib>Patrocínio, Andressa B.</creatorcontrib><creatorcontrib>Pagotti, Mariana C.</creatorcontrib><creatorcontrib>Fukui, Murilo J.</creatorcontrib><creatorcontrib>Rodrigues, Vanderlei</creatorcontrib><creatorcontrib>Magalhães, Lizandra G.</creatorcontrib><creatorcontrib>Crotti, Antônio E. M.</creatorcontrib><title>Schistosomicidal Activity of Dihydrobenzofuran Neolignans</title><title>Chemistry & biodiversity</title><addtitle>Chem Biodivers</addtitle><description>We have evaluated the antischistosomal activity of synthetic dihydrobenzofuran neolignans (DBNs) derived from (±)‐trans‐dehydrodicoumaric acid dimethyl ester (1) and (±)‐trans‐dehydrodiferulic acid dimethyl ester (2) against adult Schistosoma mansoni worms in vitro. Compound 4 ((±)‐trans‐4‐O‐acetyldehydrodiferulic acid dimethyl ester) displayed the most promising activity; at 200 μm, it kills 100 ± 0% of worms after 24 h, which resembles the result achieved with praziquantel (positive control) at 1.56 μm. The hydrogenation of the double bond between C7′ and C8′, the introduction of an additional methyl group at C3′, and a double bond between C7 and C8 decreased the schistosomicidal activity of DBNs. On the other hand, the presence of the acetoxy group at C4 played an interesting role in this activity. These results demonstrated the interesting schistosomicidal potential of DBNs, which could be further exploited.</description><subject>Acids</subject><subject>Animals</subject><subject>benzofuran neolignans</subject><subject>Dose-Response Relationship, Drug</subject><subject>Lignans - chemical synthesis</subject><subject>Lignans - chemistry</subject><subject>Lignans - pharmacology</subject><subject>Molecular Structure</subject><subject>neglected diseases</subject><subject>oxidative coupling</subject><subject>phenylpropanoids</subject><subject>Praziquantel</subject><subject>Schistosoma mansoni</subject><subject>Schistosoma mansoni - drug effects</subject><subject>Schistosomicides - chemical synthesis</subject><subject>Schistosomicides - chemistry</subject><subject>Schistosomicides - pharmacology</subject><issn>1612-1872</issn><issn>1612-1880</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkDtPwzAURi0EoqWwMqJILCwpvrbr2GNpeUkIBh5rFDsOdZXEJU6Kwq8nUUuRWJjuQ-ceXX0InQIeA8bkUqt0PSYYBMZA2R4aAgcSghB4f9dHZICOvF92fLcXh2hAZDRhjMEQyWe9sL523hVW2zTJg6mu7drWbeCyYG4XbVo5ZcovlzVVUgaPxuX2vUxKf4wOsiT35mRbR-j15vpldhc-PN3ez6YPoWZUspBLAzRNpcIiiljEqAKVME6jTGkhuQaWSNXPhhOlqTacQiQIzQiHTGeSjtDFxruq3EdjfB0X1muT50lpXONjgqmIACiHDj3_gy5dU5Xddx3FOciJFL1wvKF05byvTBavKlskVRsDjvtQ4z7UeBdqd3C21TaqMOkO_0mxA-QG-LS5af_RxbOr-duv_BvLOoH8</recordid><startdate>201807</startdate><enddate>201807</enddate><creator>Dias, Herbert J.</creator><creator>Patrocínio, Andressa B.</creator><creator>Pagotti, Mariana C.</creator><creator>Fukui, Murilo J.</creator><creator>Rodrigues, Vanderlei</creator><creator>Magalhães, Lizandra G.</creator><creator>Crotti, Antônio E. M.</creator><general>Wiley Subscription Services, Inc</general><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>7QO</scope><scope>7TM</scope><scope>8FD</scope><scope>FR3</scope><scope>K9.</scope><scope>M7N</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>201807</creationdate><title>Schistosomicidal Activity of Dihydrobenzofuran Neolignans</title><author>Dias, Herbert J. ; Patrocínio, Andressa B. ; Pagotti, Mariana C. ; Fukui, Murilo J. ; Rodrigues, Vanderlei ; Magalhães, Lizandra G. ; Crotti, Antônio E. M.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4394-69e13dd9b08774743b1ba4637fbc896c14a9b4637e62bc3ce6317823f261fcf93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Acids</topic><topic>Animals</topic><topic>benzofuran neolignans</topic><topic>Dose-Response Relationship, Drug</topic><topic>Lignans - chemical synthesis</topic><topic>Lignans - chemistry</topic><topic>Lignans - pharmacology</topic><topic>Molecular Structure</topic><topic>neglected diseases</topic><topic>oxidative coupling</topic><topic>phenylpropanoids</topic><topic>Praziquantel</topic><topic>Schistosoma mansoni</topic><topic>Schistosoma mansoni - drug effects</topic><topic>Schistosomicides - chemical synthesis</topic><topic>Schistosomicides - chemistry</topic><topic>Schistosomicides - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Dias, Herbert J.</creatorcontrib><creatorcontrib>Patrocínio, Andressa B.</creatorcontrib><creatorcontrib>Pagotti, Mariana C.</creatorcontrib><creatorcontrib>Fukui, Murilo J.</creatorcontrib><creatorcontrib>Rodrigues, Vanderlei</creatorcontrib><creatorcontrib>Magalhães, Lizandra G.</creatorcontrib><creatorcontrib>Crotti, Antônio E. M.</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry & biodiversity</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Dias, Herbert J.</au><au>Patrocínio, Andressa B.</au><au>Pagotti, Mariana C.</au><au>Fukui, Murilo J.</au><au>Rodrigues, Vanderlei</au><au>Magalhães, Lizandra G.</au><au>Crotti, Antônio E. M.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Schistosomicidal Activity of Dihydrobenzofuran Neolignans</atitle><jtitle>Chemistry & biodiversity</jtitle><addtitle>Chem Biodivers</addtitle><date>2018-07</date><risdate>2018</risdate><volume>15</volume><issue>7</issue><spage>e1800134</spage><epage>n/a</epage><pages>e1800134-n/a</pages><issn>1612-1872</issn><eissn>1612-1880</eissn><abstract>We have evaluated the antischistosomal activity of synthetic dihydrobenzofuran neolignans (DBNs) derived from (±)‐trans‐dehydrodicoumaric acid dimethyl ester (1) and (±)‐trans‐dehydrodiferulic acid dimethyl ester (2) against adult Schistosoma mansoni worms in vitro. Compound 4 ((±)‐trans‐4‐O‐acetyldehydrodiferulic acid dimethyl ester) displayed the most promising activity; at 200 μm, it kills 100 ± 0% of worms after 24 h, which resembles the result achieved with praziquantel (positive control) at 1.56 μm. The hydrogenation of the double bond between C7′ and C8′, the introduction of an additional methyl group at C3′, and a double bond between C7 and C8 decreased the schistosomicidal activity of DBNs. On the other hand, the presence of the acetoxy group at C4 played an interesting role in this activity. These results demonstrated the interesting schistosomicidal potential of DBNs, which could be further exploited.</abstract><cop>Switzerland</cop><pub>Wiley Subscription Services, Inc</pub><pmid>29754441</pmid><doi>10.1002/cbdv.201800134</doi><tpages>6</tpages></addata></record> |
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| subjects | Acids Animals benzofuran neolignans Dose-Response Relationship, Drug Lignans - chemical synthesis Lignans - chemistry Lignans - pharmacology Molecular Structure neglected diseases oxidative coupling phenylpropanoids Praziquantel Schistosoma mansoni Schistosoma mansoni - drug effects Schistosomicides - chemical synthesis Schistosomicides - chemistry Schistosomicides - pharmacology |
| title | Schistosomicidal Activity of Dihydrobenzofuran Neolignans |
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