Bioactive compounds from transformed root cultures and aerial parts of Bethencourtia hermosae
A study of Bethencourtia hermosae, aerial parts and root cultures, afforded the undescribed sesquiterpenes ceratopicanol angelate, 8β-hydroxy-african-4(5)-en-3-one tiglate, 8β-hydroxy-african-4(5)-en-3-one 3′-angeloxy-2′-methylbutanoate, 1α,8β-dihydroxy-african-4(5)-en-3-one 8β-angelate, 6α,8β-dihyd...
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| Veröffentlicht in: | Phytochemistry (Oxford) 2014-12, Vol.108, p.220-228 |
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| creator | Fraga, Braulio M. Díaz, Carmen E. Amador, Leonardo J. Reina, Matías Santana, Omar González-Coloma, Azucena |
| description | A study of Bethencourtia hermosae, aerial parts and root cultures, afforded the undescribed sesquiterpenes ceratopicanol angelate, 8β-hydroxy-african-4(5)-en-3-one tiglate, 8β-hydroxy-african-4(5)-en-3-one 3′-angeloxy-2′-methylbutanoate, 1α,8β-dihydroxy-african-4(5)-en-3-one 8β-angelate, 6α,8β-dihydroxy-african-4(5)-en-3-one8β-angelate (8), and the alkaloid hermosine. Their insect antifeedant and cytotoxic activities were also studied. [Display omitted]
•Phytochemical study of Bethencourtia hermosae aerial parts.•Components of transformed root cultures of Bethencourtia hermosae.•Insect antifeedant and cytotoxic activities of africanane sesquiterpenes.
A chemical study of Bethencourtia hermosae, aerial parts and in vitro root cultures, transformed by Agrobacterium rhizogenes, afforded the hitherto unreported sesquiterpenes ceratopicanol angelate (1), 8β-hydroxy-african-4(5)-en-3-one tiglate (4), 8β-hydroxy-african-4(5)-en-3-one 3′-angeloxy-2′-methylbutanoate (5), 1α,8β-dihydroxy-african-4(5)-en-3-one 8β-angelate (7) and 6α,8β-dihydroxy-african-4(5)-en-3-one 8β-angelate (8). In addition, 8β-hydroxy-african-4(5)-en-3-one (6) was isolated for the first time from a natural source, along with the rare sesquiterpenoid senecrassidiol (10) and two jacaranone derivatives 14 and 16. Known pyrrolizidine alkaloids, together with previously unreported hermosine (23), have also been isolated from this plant. The insect antifeedant activities of the extracts and compounds were studied together with their cytotoxic effects against insect (Sf9) and mammalian (CHO) cell lines. |
| doi_str_mv | 10.1016/j.phytochem.2014.09.010 |
| format | Article |
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•Phytochemical study of Bethencourtia hermosae aerial parts.•Components of transformed root cultures of Bethencourtia hermosae.•Insect antifeedant and cytotoxic activities of africanane sesquiterpenes.
A chemical study of Bethencourtia hermosae, aerial parts and in vitro root cultures, transformed by Agrobacterium rhizogenes, afforded the hitherto unreported sesquiterpenes ceratopicanol angelate (1), 8β-hydroxy-african-4(5)-en-3-one tiglate (4), 8β-hydroxy-african-4(5)-en-3-one 3′-angeloxy-2′-methylbutanoate (5), 1α,8β-dihydroxy-african-4(5)-en-3-one 8β-angelate (7) and 6α,8β-dihydroxy-african-4(5)-en-3-one 8β-angelate (8). In addition, 8β-hydroxy-african-4(5)-en-3-one (6) was isolated for the first time from a natural source, along with the rare sesquiterpenoid senecrassidiol (10) and two jacaranone derivatives 14 and 16. Known pyrrolizidine alkaloids, together with previously unreported hermosine (23), have also been isolated from this plant. The insect antifeedant activities of the extracts and compounds were studied together with their cytotoxic effects against insect (Sf9) and mammalian (CHO) cell lines.</description><identifier>ISSN: 0031-9422</identifier><identifier>EISSN: 1873-3700</identifier><identifier>DOI: 10.1016/j.phytochem.2014.09.010</identifier><identifier>PMID: 25301666</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Africanane ; Alkaloids ; Animals ; Antineoplastic Agents, Phytogenic - chemistry ; Antineoplastic Agents, Phytogenic - isolation & purification ; Antineoplastic Agents, Phytogenic - pharmacology ; Asteraceae - chemistry ; Bethencourtia hermosae ; Ceratopicane ; Cytotoxic effects ; Drug Screening Assays, Antitumor ; Insect antifeedants ; Insecta - cytology ; Microbial Sensitivity Tests ; Molecular Structure ; Nuclear Magnetic Resonance, Biomolecular ; Plant Roots - chemistry ; Pyrrolizidine Alkaloids - chemistry ; Pyrrolizidine Alkaloids - isolation & purification ; Senecrassane ; Sesquiterpenes ; Sesquiterpenes - chemistry ; Sesquiterpenes - isolation & purification ; Sesquiterpenes - pharmacology ; Spain ; Transformed roots</subject><ispartof>Phytochemistry (Oxford), 2014-12, Vol.108, p.220-228</ispartof><rights>2014 Elsevier Ltd</rights><rights>Copyright © 2014 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c507t-79dcbd7a213a03f1c3b8fa394bb5b0490dc004f08bc8e03ea5ddbe31482bda793</citedby><cites>FETCH-LOGICAL-c507t-79dcbd7a213a03f1c3b8fa394bb5b0490dc004f08bc8e03ea5ddbe31482bda793</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.2014.09.010$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3548,27922,27923,45993</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25301666$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Fraga, Braulio M.</creatorcontrib><creatorcontrib>Díaz, Carmen E.</creatorcontrib><creatorcontrib>Amador, Leonardo J.</creatorcontrib><creatorcontrib>Reina, Matías</creatorcontrib><creatorcontrib>Santana, Omar</creatorcontrib><creatorcontrib>González-Coloma, Azucena</creatorcontrib><title>Bioactive compounds from transformed root cultures and aerial parts of Bethencourtia hermosae</title><title>Phytochemistry (Oxford)</title><addtitle>Phytochemistry</addtitle><description>A study of Bethencourtia hermosae, aerial parts and root cultures, afforded the undescribed sesquiterpenes ceratopicanol angelate, 8β-hydroxy-african-4(5)-en-3-one tiglate, 8β-hydroxy-african-4(5)-en-3-one 3′-angeloxy-2′-methylbutanoate, 1α,8β-dihydroxy-african-4(5)-en-3-one 8β-angelate, 6α,8β-dihydroxy-african-4(5)-en-3-one8β-angelate (8), and the alkaloid hermosine. Their insect antifeedant and cytotoxic activities were also studied. [Display omitted]
•Phytochemical study of Bethencourtia hermosae aerial parts.•Components of transformed root cultures of Bethencourtia hermosae.•Insect antifeedant and cytotoxic activities of africanane sesquiterpenes.
A chemical study of Bethencourtia hermosae, aerial parts and in vitro root cultures, transformed by Agrobacterium rhizogenes, afforded the hitherto unreported sesquiterpenes ceratopicanol angelate (1), 8β-hydroxy-african-4(5)-en-3-one tiglate (4), 8β-hydroxy-african-4(5)-en-3-one 3′-angeloxy-2′-methylbutanoate (5), 1α,8β-dihydroxy-african-4(5)-en-3-one 8β-angelate (7) and 6α,8β-dihydroxy-african-4(5)-en-3-one 8β-angelate (8). In addition, 8β-hydroxy-african-4(5)-en-3-one (6) was isolated for the first time from a natural source, along with the rare sesquiterpenoid senecrassidiol (10) and two jacaranone derivatives 14 and 16. Known pyrrolizidine alkaloids, together with previously unreported hermosine (23), have also been isolated from this plant. The insect antifeedant activities of the extracts and compounds were studied together with their cytotoxic effects against insect (Sf9) and mammalian (CHO) cell lines.</description><subject>Africanane</subject><subject>Alkaloids</subject><subject>Animals</subject><subject>Antineoplastic Agents, Phytogenic - chemistry</subject><subject>Antineoplastic Agents, Phytogenic - isolation & purification</subject><subject>Antineoplastic Agents, Phytogenic - pharmacology</subject><subject>Asteraceae - chemistry</subject><subject>Bethencourtia hermosae</subject><subject>Ceratopicane</subject><subject>Cytotoxic effects</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Insect antifeedants</subject><subject>Insecta - cytology</subject><subject>Microbial Sensitivity Tests</subject><subject>Molecular Structure</subject><subject>Nuclear Magnetic Resonance, Biomolecular</subject><subject>Plant Roots - chemistry</subject><subject>Pyrrolizidine Alkaloids - chemistry</subject><subject>Pyrrolizidine Alkaloids - isolation & purification</subject><subject>Senecrassane</subject><subject>Sesquiterpenes</subject><subject>Sesquiterpenes - chemistry</subject><subject>Sesquiterpenes - isolation & purification</subject><subject>Sesquiterpenes - pharmacology</subject><subject>Spain</subject><subject>Transformed roots</subject><issn>0031-9422</issn><issn>1873-3700</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkMlOwzAURS0EgjL8AnjJJuE5zrikFZOExAaWyPLworpK4mA7lfr3pCqwZfU2596rdwi5YZAyYOXdJh3Xu-j0Gvs0A5an0KTA4IgsWF3xhFcAx2QBwFnS5Fl2Rs5D2ABAUZTlKTnLCj63lOWCfC6tkzraLVLt-tFNgwm09a6n0cshtM73aKh3LlI9dXHyGKgcDJXorezoKH0M1LV0iXGNg3aTj1bSNfreBYmX5KSVXcCrn3tBPh4f3lfPyevb08vq_jXRBVQxqRqjlalkxrgE3jLNVd1K3uRKFQryBowGyFuola4ROMrCGIWc5XWmjKwafkFuD72jd18Thih6GzR2nRzQTUGwkudZBUVWzmh1QLV3IXhsxehtL_1OMBB7t2Ij_tyKvVsBjZjdzsnrn5FJzVL-cr8yZ-D-AOD86taiF0HbWQoa61FHYZz9d-QbL5WRlw</recordid><startdate>20141201</startdate><enddate>20141201</enddate><creator>Fraga, Braulio M.</creator><creator>Díaz, Carmen E.</creator><creator>Amador, Leonardo J.</creator><creator>Reina, Matías</creator><creator>Santana, Omar</creator><creator>González-Coloma, Azucena</creator><general>Elsevier Ltd</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>7X8</scope></search><sort><creationdate>20141201</creationdate><title>Bioactive compounds from transformed root cultures and aerial parts of Bethencourtia hermosae</title><author>Fraga, Braulio M. ; Díaz, Carmen E. ; Amador, Leonardo J. ; Reina, Matías ; Santana, Omar ; González-Coloma, Azucena</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c507t-79dcbd7a213a03f1c3b8fa394bb5b0490dc004f08bc8e03ea5ddbe31482bda793</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Africanane</topic><topic>Alkaloids</topic><topic>Animals</topic><topic>Antineoplastic Agents, Phytogenic - chemistry</topic><topic>Antineoplastic Agents, Phytogenic - isolation & purification</topic><topic>Antineoplastic Agents, Phytogenic - pharmacology</topic><topic>Asteraceae - chemistry</topic><topic>Bethencourtia hermosae</topic><topic>Ceratopicane</topic><topic>Cytotoxic effects</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Insect antifeedants</topic><topic>Insecta - cytology</topic><topic>Microbial Sensitivity Tests</topic><topic>Molecular Structure</topic><topic>Nuclear Magnetic Resonance, Biomolecular</topic><topic>Plant Roots - chemistry</topic><topic>Pyrrolizidine Alkaloids - chemistry</topic><topic>Pyrrolizidine Alkaloids - isolation & purification</topic><topic>Senecrassane</topic><topic>Sesquiterpenes</topic><topic>Sesquiterpenes - chemistry</topic><topic>Sesquiterpenes - isolation & purification</topic><topic>Sesquiterpenes - pharmacology</topic><topic>Spain</topic><topic>Transformed roots</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Fraga, Braulio M.</creatorcontrib><creatorcontrib>Díaz, Carmen E.</creatorcontrib><creatorcontrib>Amador, Leonardo J.</creatorcontrib><creatorcontrib>Reina, Matías</creatorcontrib><creatorcontrib>Santana, Omar</creatorcontrib><creatorcontrib>González-Coloma, Azucena</creatorcontrib><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>Fraga, Braulio M.</au><au>Díaz, Carmen E.</au><au>Amador, Leonardo J.</au><au>Reina, Matías</au><au>Santana, Omar</au><au>González-Coloma, Azucena</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Bioactive compounds from transformed root cultures and aerial parts of Bethencourtia hermosae</atitle><jtitle>Phytochemistry (Oxford)</jtitle><addtitle>Phytochemistry</addtitle><date>2014-12-01</date><risdate>2014</risdate><volume>108</volume><spage>220</spage><epage>228</epage><pages>220-228</pages><issn>0031-9422</issn><eissn>1873-3700</eissn><abstract>A study of Bethencourtia hermosae, aerial parts and root cultures, afforded the undescribed sesquiterpenes ceratopicanol angelate, 8β-hydroxy-african-4(5)-en-3-one tiglate, 8β-hydroxy-african-4(5)-en-3-one 3′-angeloxy-2′-methylbutanoate, 1α,8β-dihydroxy-african-4(5)-en-3-one 8β-angelate, 6α,8β-dihydroxy-african-4(5)-en-3-one8β-angelate (8), and the alkaloid hermosine. Their insect antifeedant and cytotoxic activities were also studied. [Display omitted]
•Phytochemical study of Bethencourtia hermosae aerial parts.•Components of transformed root cultures of Bethencourtia hermosae.•Insect antifeedant and cytotoxic activities of africanane sesquiterpenes.
A chemical study of Bethencourtia hermosae, aerial parts and in vitro root cultures, transformed by Agrobacterium rhizogenes, afforded the hitherto unreported sesquiterpenes ceratopicanol angelate (1), 8β-hydroxy-african-4(5)-en-3-one tiglate (4), 8β-hydroxy-african-4(5)-en-3-one 3′-angeloxy-2′-methylbutanoate (5), 1α,8β-dihydroxy-african-4(5)-en-3-one 8β-angelate (7) and 6α,8β-dihydroxy-african-4(5)-en-3-one 8β-angelate (8). In addition, 8β-hydroxy-african-4(5)-en-3-one (6) was isolated for the first time from a natural source, along with the rare sesquiterpenoid senecrassidiol (10) and two jacaranone derivatives 14 and 16. Known pyrrolizidine alkaloids, together with previously unreported hermosine (23), have also been isolated from this plant. The insect antifeedant activities of the extracts and compounds were studied together with their cytotoxic effects against insect (Sf9) and mammalian (CHO) cell lines.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>25301666</pmid><doi>10.1016/j.phytochem.2014.09.010</doi><tpages>9</tpages></addata></record> |
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| subjects | Africanane Alkaloids Animals Antineoplastic Agents, Phytogenic - chemistry Antineoplastic Agents, Phytogenic - isolation & purification Antineoplastic Agents, Phytogenic - pharmacology Asteraceae - chemistry Bethencourtia hermosae Ceratopicane Cytotoxic effects Drug Screening Assays, Antitumor Insect antifeedants Insecta - cytology Microbial Sensitivity Tests Molecular Structure Nuclear Magnetic Resonance, Biomolecular Plant Roots - chemistry Pyrrolizidine Alkaloids - chemistry Pyrrolizidine Alkaloids - isolation & purification Senecrassane Sesquiterpenes Sesquiterpenes - chemistry Sesquiterpenes - isolation & purification Sesquiterpenes - pharmacology Spain Transformed roots |
| title | Bioactive compounds from transformed root cultures and aerial parts of Bethencourtia hermosae |
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