Prenylated anthronoid antioxidants from the stem bark of Harungana madagascariensis
Two new prenylated anthronoids, harunmadagascarins A and B, were isolated from the stem bark of Harungana madagascariensis. Two new prenylated anthronoids, harunmadagascarins A and B, were isolated from the stem bark of Harungana madagascariensis along with six known compounds including two anthrono...
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| Veröffentlicht in: | Phytochemistry (Oxford) 2005-05, Vol.66 (10), p.1174-1179 |
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| creator | Kouam, Simeon F. Ngadjui, Bonaventure T. Krohn, Karsten Wafo, Pascal Ajaz, Asma Choudhary, M. Iqbal |
| description | Two new prenylated anthronoids, harunmadagascarins A and B, were isolated from the stem bark of
Harungana madagascariensis.
Two new prenylated anthronoids, harunmadagascarins A and B, were isolated from the stem bark of
Harungana madagascariensis along with six known compounds including two anthronoids: harunganol B and harungin anthrone, one benzophenone: methyl 3-formyl-2,4-dihydroxy-6-methyl benzoate and three pentacyclic triterpenes: friedelin, lupeol and betulinic acid. Harunmadagascarins A and B were characterized as 8,9-dihydroxy-4,4-bis-(3,3-dimethylallyl)-6-methyl-2,3-(2,2-dimethylpyrano)anthrone and 8,9-dihydroxy-4,4,5-tris-(3,3-dimethylallyl)-6-methyl-2,3-(2,2-dimethylpyrano)anthrone, respectively. The structures of these secondary metabolites were determined by spectroscopic means and comparison with the published data. Methyl 3-formyl-2,4-dihydroxy-6-methyl benzoate was isolated for the first time from a plant. Harunmadagascarins A and B, harunganol B and harungin anthrone exhibited significant antioxidant activity. |
| doi_str_mv | 10.1016/j.phytochem.2005.03.022 |
| format | Article |
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Harungana madagascariensis.
Two new prenylated anthronoids, harunmadagascarins A and B, were isolated from the stem bark of
Harungana madagascariensis along with six known compounds including two anthronoids: harunganol B and harungin anthrone, one benzophenone: methyl 3-formyl-2,4-dihydroxy-6-methyl benzoate and three pentacyclic triterpenes: friedelin, lupeol and betulinic acid. Harunmadagascarins A and B were characterized as 8,9-dihydroxy-4,4-bis-(3,3-dimethylallyl)-6-methyl-2,3-(2,2-dimethylpyrano)anthrone and 8,9-dihydroxy-4,4,5-tris-(3,3-dimethylallyl)-6-methyl-2,3-(2,2-dimethylpyrano)anthrone, respectively. The structures of these secondary metabolites were determined by spectroscopic means and comparison with the published data. Methyl 3-formyl-2,4-dihydroxy-6-methyl benzoate was isolated for the first time from a plant. Harunmadagascarins A and B, harunganol B and harungin anthrone exhibited significant antioxidant activity.</description><identifier>ISSN: 0031-9422</identifier><identifier>EISSN: 1873-3700</identifier><identifier>DOI: 10.1016/j.phytochem.2005.03.022</identifier><identifier>PMID: 15924922</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>Anthracenes - chemistry ; anthronoids ; Antioxidant ; antioxidants ; Antioxidants - chemistry ; benzophenone ; Biological and medical sciences ; Chemical constitution ; chemical structure ; Clusiaceae - chemistry ; Free Radical Scavengers - chemistry ; Fundamental and applied biological sciences. Psychology ; Harungana madagascariensis ; harunganol ; harungin anthrone ; harunmadagascarin ; Harunmadagascarins A and B ; Hypericaceae ; Insecta ; Invertebrates ; Molecular Structure ; Pathology ; phytochemicals ; Plant Bark - chemistry ; plant extracts ; Plant physiology and development ; Plant Stems - chemistry ; Prenylated anthronoids ; spectral analysis ; stereochemistry ; triterpenoids</subject><ispartof>Phytochemistry (Oxford), 2005-05, Vol.66 (10), p.1174-1179</ispartof><rights>2005 Elsevier Ltd</rights><rights>2005 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c404t-575efdd4d8994b20d15307004c0b70f897a4b5e0d1228e2abda325453151a7563</citedby><cites>FETCH-LOGICAL-c404t-575efdd4d8994b20d15307004c0b70f897a4b5e0d1228e2abda325453151a7563</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.phytochem.2005.03.022$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>315,782,786,3554,27933,27934,46004</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=16864648$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15924922$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kouam, Simeon F.</creatorcontrib><creatorcontrib>Ngadjui, Bonaventure T.</creatorcontrib><creatorcontrib>Krohn, Karsten</creatorcontrib><creatorcontrib>Wafo, Pascal</creatorcontrib><creatorcontrib>Ajaz, Asma</creatorcontrib><creatorcontrib>Choudhary, M. Iqbal</creatorcontrib><title>Prenylated anthronoid antioxidants from the stem bark of Harungana madagascariensis</title><title>Phytochemistry (Oxford)</title><addtitle>Phytochemistry</addtitle><description>Two new prenylated anthronoids, harunmadagascarins A and B, were isolated from the stem bark of
Harungana madagascariensis.
Two new prenylated anthronoids, harunmadagascarins A and B, were isolated from the stem bark of
Harungana madagascariensis along with six known compounds including two anthronoids: harunganol B and harungin anthrone, one benzophenone: methyl 3-formyl-2,4-dihydroxy-6-methyl benzoate and three pentacyclic triterpenes: friedelin, lupeol and betulinic acid. Harunmadagascarins A and B were characterized as 8,9-dihydroxy-4,4-bis-(3,3-dimethylallyl)-6-methyl-2,3-(2,2-dimethylpyrano)anthrone and 8,9-dihydroxy-4,4,5-tris-(3,3-dimethylallyl)-6-methyl-2,3-(2,2-dimethylpyrano)anthrone, respectively. The structures of these secondary metabolites were determined by spectroscopic means and comparison with the published data. Methyl 3-formyl-2,4-dihydroxy-6-methyl benzoate was isolated for the first time from a plant. Harunmadagascarins A and B, harunganol B and harungin anthrone exhibited significant antioxidant activity.</description><subject>Anthracenes - chemistry</subject><subject>anthronoids</subject><subject>Antioxidant</subject><subject>antioxidants</subject><subject>Antioxidants - chemistry</subject><subject>benzophenone</subject><subject>Biological and medical sciences</subject><subject>Chemical constitution</subject><subject>chemical structure</subject><subject>Clusiaceae - chemistry</subject><subject>Free Radical Scavengers - chemistry</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Harungana madagascariensis</subject><subject>harunganol</subject><subject>harungin anthrone</subject><subject>harunmadagascarin</subject><subject>Harunmadagascarins A and B</subject><subject>Hypericaceae</subject><subject>Insecta</subject><subject>Invertebrates</subject><subject>Molecular Structure</subject><subject>Pathology</subject><subject>phytochemicals</subject><subject>Plant Bark - chemistry</subject><subject>plant extracts</subject><subject>Plant physiology and development</subject><subject>Plant Stems - chemistry</subject><subject>Prenylated anthronoids</subject><subject>spectral analysis</subject><subject>stereochemistry</subject><subject>triterpenoids</subject><issn>0031-9422</issn><issn>1873-3700</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkEtv00AQgFcIREPhL1Bf4GYz-_LjWFXQIlUCqfS8Gu-Okw22N-w6iPx7Nk1Ej5xmNPrm9TF2xaHiwOtP22q3OSzBbmiqBICuQFYgxAu24m0jS9kAvGQrAMnLTglxwd6ktIUM6rp-zS647oTqhFixh--R5sOIC7kC52UTwxz8U-rDH-9yTMUQw1QsGyrSQlPRY_xZhKG4w7if1zhjMaHDNSaL0dOcfHrLXg04Jnp3jpfs8cvnHzd35f2326831_elVaCWUjeaBueUa7tO9QIc1xLy4cpC38DQdg2qXlOuC9GSwN6hFFppyTXHRtfykn08zd3F8GtPaTGTT5bGEWcK-2Tqpm3zvyqDzQm0MaQUaTC76CeMB8PBHH2arfnn0xx9GpAm-8yd788r9v1E7rnvLDADH87AUcA4RJytT89c3daqVm3mrk7cgMHgOmbm8UEAl5D3Q90dv7k-EZSV_fYUTbLZpyXnI9nFuOD_e-5fL5ehfQ</recordid><startdate>200505</startdate><enddate>200505</enddate><creator>Kouam, Simeon F.</creator><creator>Ngadjui, Bonaventure T.</creator><creator>Krohn, Karsten</creator><creator>Wafo, Pascal</creator><creator>Ajaz, Asma</creator><creator>Choudhary, M. Iqbal</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>FBQ</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>200505</creationdate><title>Prenylated anthronoid antioxidants from the stem bark of Harungana madagascariensis</title><author>Kouam, Simeon F. ; Ngadjui, Bonaventure T. ; Krohn, Karsten ; Wafo, Pascal ; Ajaz, Asma ; Choudhary, M. Iqbal</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c404t-575efdd4d8994b20d15307004c0b70f897a4b5e0d1228e2abda325453151a7563</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Anthracenes - chemistry</topic><topic>anthronoids</topic><topic>Antioxidant</topic><topic>antioxidants</topic><topic>Antioxidants - chemistry</topic><topic>benzophenone</topic><topic>Biological and medical sciences</topic><topic>Chemical constitution</topic><topic>chemical structure</topic><topic>Clusiaceae - chemistry</topic><topic>Free Radical Scavengers - chemistry</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Harungana madagascariensis</topic><topic>harunganol</topic><topic>harungin anthrone</topic><topic>harunmadagascarin</topic><topic>Harunmadagascarins A and B</topic><topic>Hypericaceae</topic><topic>Insecta</topic><topic>Invertebrates</topic><topic>Molecular Structure</topic><topic>Pathology</topic><topic>phytochemicals</topic><topic>Plant Bark - chemistry</topic><topic>plant extracts</topic><topic>Plant physiology and development</topic><topic>Plant Stems - chemistry</topic><topic>Prenylated anthronoids</topic><topic>spectral analysis</topic><topic>stereochemistry</topic><topic>triterpenoids</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kouam, Simeon F.</creatorcontrib><creatorcontrib>Ngadjui, Bonaventure T.</creatorcontrib><creatorcontrib>Krohn, Karsten</creatorcontrib><creatorcontrib>Wafo, Pascal</creatorcontrib><creatorcontrib>Ajaz, Asma</creatorcontrib><creatorcontrib>Choudhary, M. Iqbal</creatorcontrib><collection>AGRIS</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>Phytochemistry (Oxford)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kouam, Simeon F.</au><au>Ngadjui, Bonaventure T.</au><au>Krohn, Karsten</au><au>Wafo, Pascal</au><au>Ajaz, Asma</au><au>Choudhary, M. Iqbal</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Prenylated anthronoid antioxidants from the stem bark of Harungana madagascariensis</atitle><jtitle>Phytochemistry (Oxford)</jtitle><addtitle>Phytochemistry</addtitle><date>2005-05</date><risdate>2005</risdate><volume>66</volume><issue>10</issue><spage>1174</spage><epage>1179</epage><pages>1174-1179</pages><issn>0031-9422</issn><eissn>1873-3700</eissn><abstract>Two new prenylated anthronoids, harunmadagascarins A and B, were isolated from the stem bark of
Harungana madagascariensis.
Two new prenylated anthronoids, harunmadagascarins A and B, were isolated from the stem bark of
Harungana madagascariensis along with six known compounds including two anthronoids: harunganol B and harungin anthrone, one benzophenone: methyl 3-formyl-2,4-dihydroxy-6-methyl benzoate and three pentacyclic triterpenes: friedelin, lupeol and betulinic acid. Harunmadagascarins A and B were characterized as 8,9-dihydroxy-4,4-bis-(3,3-dimethylallyl)-6-methyl-2,3-(2,2-dimethylpyrano)anthrone and 8,9-dihydroxy-4,4,5-tris-(3,3-dimethylallyl)-6-methyl-2,3-(2,2-dimethylpyrano)anthrone, respectively. The structures of these secondary metabolites were determined by spectroscopic means and comparison with the published data. Methyl 3-formyl-2,4-dihydroxy-6-methyl benzoate was isolated for the first time from a plant. Harunmadagascarins A and B, harunganol B and harungin anthrone exhibited significant antioxidant activity.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>15924922</pmid><doi>10.1016/j.phytochem.2005.03.022</doi><tpages>6</tpages></addata></record> |
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| subjects | Anthracenes - chemistry anthronoids Antioxidant antioxidants Antioxidants - chemistry benzophenone Biological and medical sciences Chemical constitution chemical structure Clusiaceae - chemistry Free Radical Scavengers - chemistry Fundamental and applied biological sciences. Psychology Harungana madagascariensis harunganol harungin anthrone harunmadagascarin Harunmadagascarins A and B Hypericaceae Insecta Invertebrates Molecular Structure Pathology phytochemicals Plant Bark - chemistry plant extracts Plant physiology and development Plant Stems - chemistry Prenylated anthronoids spectral analysis stereochemistry triterpenoids |
| title | Prenylated anthronoid antioxidants from the stem bark of Harungana madagascariensis |
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