ent-Beyerane diterpenoids from the heartwood of Excoecaria parvifolia
The heartwood of Excoecaria parvifolia afforded 12 beyerane diterpenes ( 1– 12), four of which ( 5– 7 and 12) have unusual structures: ent-3-oxa-beyer-15-en-2-one, ( 5); ent-15,16-epoxy-2-hydroxy-19-norbeyer-1,4-dien-3-one ( 6); methyl ent-2,4-seco-15,16-epoxy-4-oxo-3,19-dinorbeyer-15-en-2-oate ( 7)...
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| Veröffentlicht in: | Phytochemistry (Oxford) 2007-02, Vol.68 (4), p.546-553 |
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| creator | Grace, Mary H. Faraldos, Juan A. Lila, Mary Ann Coates, Robert M. |
| description | The heartwood of
Excoecaria parvifolia afforded 12 beyerane diterpenes (
1–
12), four of which (
5–
7 and
12) have unusual structures:
ent-3-oxa-beyer-15-en-2-one, (
5);
ent-15,16-epoxy-2-hydroxy-19-norbeyer-1,4-dien-3-one (
6); methyl
ent-2,4-seco-15,16-epoxy-4-oxo-3,19-dinorbeyer-15-en-2-oate (
7); and
ent-2,17-dihydroxy-19-norbeyer-1,4,15-trien-3-one (
12). The isolated diterpenes were tested for their cytotoxic activity against leukemia cells (L1210), but only compounds
2 and
5 exhibited potent activity.
Chromatographic fractionations of the toluene extract of the heartwood of
Excoecaria parvifolia collected in Australia resulted in the isolation of 12 beyerane diterpenes (
1–
12), and the triterpene, lupeol. Four of the isolated diterpenoids (
5–
7 and
12) have unusual structures:
ent-3-oxa-beyer-15-en-2-one, (
5);
ent-15,16-epoxy-2-hydroxy-19-norbeyer-1,4-dien-3-one (
6); methyl
ent-2,4-seco-15,16-epoxy-4-oxo-3,19-dinorbeyer-15-en-2-oate (
7); and
ent-2,17-dihydroxy-19-norbeyer-1,4,15-trien-3-one (
12). The structures were established by spectroscopic analyses, NMR data comparisons with similar diterpenes, and chemical correlations. All the diterpenes are assumed to have the same absolute configuration as the co-occurring (+)-stachenol (
4). Diosphenol
2 and nor-lactone
5 exhibited significant potency in bioassays for cytotoxic activity against leukemia cells (L1210). Plausible biosynthetic pathways are proposed to explain the origin of the diterpene metabolites. |
| doi_str_mv | 10.1016/j.phytochem.2006.11.010 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_68989313</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S0031942206007011</els_id><sourcerecordid>68989313</sourcerecordid><originalsourceid>FETCH-LOGICAL-c423t-5aba2dab9ccdfede282c805ead77c4ba10af3ca3d27fee9de0191802b2adf9c53</originalsourceid><addsrcrecordid>eNqF0E1vEzEQgGELgWgI_AW6F7jtMmPv57FU4UOqxAF6tmbtMXG0Gwd7U8i_x1UieuTkyzPj0SvENUKFgO2HXXXYnpZgtjxXEqCtECtAeCZW2HeqVB3Ac7ECUFgOtZRX4lVKOwBomrZ9Ka6ww6FtZbcSG94v5Uc-caQ9F9YvHA-8D96mwsUwF8uWiy1TXH6HYIvgis0fE9hQ9FQcKD54FyZPr8ULR1PiN5d3Le4_bX7cfinvvn3-entzV5paqqVsaCRpaRyMsY4ty16aHhom23WmHgmBnDKkrOwc82AZcMAe5CjJusE0ai3en_ceYvh15LTo2SfD05SPD8ek237oB4Uqw-4MTQwpRXb6EP1M8aQR9GNBvdP_CurHghpR54J58u3li-M4s32auyTL4N0FUDI0uRzO-PTk-gaxrvvsrs_OUdD0M2Zz_10CKoCu7jEHWYubs-Cc7MFz1Ml43hu2PrJZtA3-v-f-Bbcvnqg</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>68989313</pqid></control><display><type>article</type><title>ent-Beyerane diterpenoids from the heartwood of Excoecaria parvifolia</title><source>MEDLINE</source><source>Elsevier ScienceDirect Journals</source><creator>Grace, Mary H. ; Faraldos, Juan A. ; Lila, Mary Ann ; Coates, Robert M.</creator><creatorcontrib>Grace, Mary H. ; Faraldos, Juan A. ; Lila, Mary Ann ; Coates, Robert M.</creatorcontrib><description>The heartwood of
Excoecaria parvifolia afforded 12 beyerane diterpenes (
1–
12), four of which (
5–
7 and
12) have unusual structures:
ent-3-oxa-beyer-15-en-2-one, (
5);
ent-15,16-epoxy-2-hydroxy-19-norbeyer-1,4-dien-3-one (
6); methyl
ent-2,4-seco-15,16-epoxy-4-oxo-3,19-dinorbeyer-15-en-2-oate (
7); and
ent-2,17-dihydroxy-19-norbeyer-1,4,15-trien-3-one (
12). The isolated diterpenes were tested for their cytotoxic activity against leukemia cells (L1210), but only compounds
2 and
5 exhibited potent activity.
Chromatographic fractionations of the toluene extract of the heartwood of
Excoecaria parvifolia collected in Australia resulted in the isolation of 12 beyerane diterpenes (
1–
12), and the triterpene, lupeol. Four of the isolated diterpenoids (
5–
7 and
12) have unusual structures:
ent-3-oxa-beyer-15-en-2-one, (
5);
ent-15,16-epoxy-2-hydroxy-19-norbeyer-1,4-dien-3-one (
6); methyl
ent-2,4-seco-15,16-epoxy-4-oxo-3,19-dinorbeyer-15-en-2-oate (
7); and
ent-2,17-dihydroxy-19-norbeyer-1,4,15-trien-3-one (
12). The structures were established by spectroscopic analyses, NMR data comparisons with similar diterpenes, and chemical correlations. All the diterpenes are assumed to have the same absolute configuration as the co-occurring (+)-stachenol (
4). Diosphenol
2 and nor-lactone
5 exhibited significant potency in bioassays for cytotoxic activity against leukemia cells (L1210). Plausible biosynthetic pathways are proposed to explain the origin of the diterpene metabolites.</description><identifier>ISSN: 0031-9422</identifier><identifier>EISSN: 1873-3700</identifier><identifier>DOI: 10.1016/j.phytochem.2006.11.010</identifier><identifier>PMID: 17196627</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>anticarcinogenic activity ; beyerane diterpenes ; Biological and medical sciences ; Chemical constitution ; chemical structure ; cultured cells ; Cytotoxicity ; Diosphenols ; Diterpenes - chemistry ; Diterpenes - isolation & purification ; Diterpenoids ; ent-Beyeranes ; Euphorbiaceae ; Euphorbiaceae - chemistry ; Excoecaria ; Excoecaria parvifolia ; Fundamental and applied biological sciences. Psychology ; Heartwood ; L1210 ; lupeol ; mice ; Models, Molecular ; Molecular Structure ; phytochemicals ; Plant Oils - chemistry ; Plant physiology and development ; spectral analysis ; triterpenoids ; Wood</subject><ispartof>Phytochemistry (Oxford), 2007-02, Vol.68 (4), p.546-553</ispartof><rights>2006 Elsevier Ltd</rights><rights>2007 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c423t-5aba2dab9ccdfede282c805ead77c4ba10af3ca3d27fee9de0191802b2adf9c53</citedby><cites>FETCH-LOGICAL-c423t-5aba2dab9ccdfede282c805ead77c4ba10af3ca3d27fee9de0191802b2adf9c53</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0031942206007011$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3536,27903,27904,65309</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=18511448$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/17196627$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Grace, Mary H.</creatorcontrib><creatorcontrib>Faraldos, Juan A.</creatorcontrib><creatorcontrib>Lila, Mary Ann</creatorcontrib><creatorcontrib>Coates, Robert M.</creatorcontrib><title>ent-Beyerane diterpenoids from the heartwood of Excoecaria parvifolia</title><title>Phytochemistry (Oxford)</title><addtitle>Phytochemistry</addtitle><description>The heartwood of
Excoecaria parvifolia afforded 12 beyerane diterpenes (
1–
12), four of which (
5–
7 and
12) have unusual structures:
ent-3-oxa-beyer-15-en-2-one, (
5);
ent-15,16-epoxy-2-hydroxy-19-norbeyer-1,4-dien-3-one (
6); methyl
ent-2,4-seco-15,16-epoxy-4-oxo-3,19-dinorbeyer-15-en-2-oate (
7); and
ent-2,17-dihydroxy-19-norbeyer-1,4,15-trien-3-one (
12). The isolated diterpenes were tested for their cytotoxic activity against leukemia cells (L1210), but only compounds
2 and
5 exhibited potent activity.
Chromatographic fractionations of the toluene extract of the heartwood of
Excoecaria parvifolia collected in Australia resulted in the isolation of 12 beyerane diterpenes (
1–
12), and the triterpene, lupeol. Four of the isolated diterpenoids (
5–
7 and
12) have unusual structures:
ent-3-oxa-beyer-15-en-2-one, (
5);
ent-15,16-epoxy-2-hydroxy-19-norbeyer-1,4-dien-3-one (
6); methyl
ent-2,4-seco-15,16-epoxy-4-oxo-3,19-dinorbeyer-15-en-2-oate (
7); and
ent-2,17-dihydroxy-19-norbeyer-1,4,15-trien-3-one (
12). The structures were established by spectroscopic analyses, NMR data comparisons with similar diterpenes, and chemical correlations. All the diterpenes are assumed to have the same absolute configuration as the co-occurring (+)-stachenol (
4). Diosphenol
2 and nor-lactone
5 exhibited significant potency in bioassays for cytotoxic activity against leukemia cells (L1210). Plausible biosynthetic pathways are proposed to explain the origin of the diterpene metabolites.</description><subject>anticarcinogenic activity</subject><subject>beyerane diterpenes</subject><subject>Biological and medical sciences</subject><subject>Chemical constitution</subject><subject>chemical structure</subject><subject>cultured cells</subject><subject>Cytotoxicity</subject><subject>Diosphenols</subject><subject>Diterpenes - chemistry</subject><subject>Diterpenes - isolation & purification</subject><subject>Diterpenoids</subject><subject>ent-Beyeranes</subject><subject>Euphorbiaceae</subject><subject>Euphorbiaceae - chemistry</subject><subject>Excoecaria</subject><subject>Excoecaria parvifolia</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Heartwood</subject><subject>L1210</subject><subject>lupeol</subject><subject>mice</subject><subject>Models, Molecular</subject><subject>Molecular Structure</subject><subject>phytochemicals</subject><subject>Plant Oils - chemistry</subject><subject>Plant physiology and development</subject><subject>spectral analysis</subject><subject>triterpenoids</subject><subject>Wood</subject><issn>0031-9422</issn><issn>1873-3700</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqF0E1vEzEQgGELgWgI_AW6F7jtMmPv57FU4UOqxAF6tmbtMXG0Gwd7U8i_x1UieuTkyzPj0SvENUKFgO2HXXXYnpZgtjxXEqCtECtAeCZW2HeqVB3Ac7ECUFgOtZRX4lVKOwBomrZ9Ka6ww6FtZbcSG94v5Uc-caQ9F9YvHA-8D96mwsUwF8uWiy1TXH6HYIvgis0fE9hQ9FQcKD54FyZPr8ULR1PiN5d3Le4_bX7cfinvvn3-entzV5paqqVsaCRpaRyMsY4ty16aHhom23WmHgmBnDKkrOwc82AZcMAe5CjJusE0ai3en_ceYvh15LTo2SfD05SPD8ek237oB4Uqw-4MTQwpRXb6EP1M8aQR9GNBvdP_CurHghpR54J58u3li-M4s32auyTL4N0FUDI0uRzO-PTk-gaxrvvsrs_OUdD0M2Zz_10CKoCu7jEHWYubs-Cc7MFz1Ml43hu2PrJZtA3-v-f-Bbcvnqg</recordid><startdate>20070201</startdate><enddate>20070201</enddate><creator>Grace, Mary H.</creator><creator>Faraldos, Juan A.</creator><creator>Lila, Mary Ann</creator><creator>Coates, Robert M.</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>20070201</creationdate><title>ent-Beyerane diterpenoids from the heartwood of Excoecaria parvifolia</title><author>Grace, Mary H. ; Faraldos, Juan A. ; Lila, Mary Ann ; Coates, Robert M.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c423t-5aba2dab9ccdfede282c805ead77c4ba10af3ca3d27fee9de0191802b2adf9c53</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>anticarcinogenic activity</topic><topic>beyerane diterpenes</topic><topic>Biological and medical sciences</topic><topic>Chemical constitution</topic><topic>chemical structure</topic><topic>cultured cells</topic><topic>Cytotoxicity</topic><topic>Diosphenols</topic><topic>Diterpenes - chemistry</topic><topic>Diterpenes - isolation & purification</topic><topic>Diterpenoids</topic><topic>ent-Beyeranes</topic><topic>Euphorbiaceae</topic><topic>Euphorbiaceae - chemistry</topic><topic>Excoecaria</topic><topic>Excoecaria parvifolia</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Heartwood</topic><topic>L1210</topic><topic>lupeol</topic><topic>mice</topic><topic>Models, Molecular</topic><topic>Molecular Structure</topic><topic>phytochemicals</topic><topic>Plant Oils - chemistry</topic><topic>Plant physiology and development</topic><topic>spectral analysis</topic><topic>triterpenoids</topic><topic>Wood</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Grace, Mary H.</creatorcontrib><creatorcontrib>Faraldos, Juan A.</creatorcontrib><creatorcontrib>Lila, Mary Ann</creatorcontrib><creatorcontrib>Coates, Robert M.</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>Grace, Mary H.</au><au>Faraldos, Juan A.</au><au>Lila, Mary Ann</au><au>Coates, Robert M.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>ent-Beyerane diterpenoids from the heartwood of Excoecaria parvifolia</atitle><jtitle>Phytochemistry (Oxford)</jtitle><addtitle>Phytochemistry</addtitle><date>2007-02-01</date><risdate>2007</risdate><volume>68</volume><issue>4</issue><spage>546</spage><epage>553</epage><pages>546-553</pages><issn>0031-9422</issn><eissn>1873-3700</eissn><abstract>The heartwood of
Excoecaria parvifolia afforded 12 beyerane diterpenes (
1–
12), four of which (
5–
7 and
12) have unusual structures:
ent-3-oxa-beyer-15-en-2-one, (
5);
ent-15,16-epoxy-2-hydroxy-19-norbeyer-1,4-dien-3-one (
6); methyl
ent-2,4-seco-15,16-epoxy-4-oxo-3,19-dinorbeyer-15-en-2-oate (
7); and
ent-2,17-dihydroxy-19-norbeyer-1,4,15-trien-3-one (
12). The isolated diterpenes were tested for their cytotoxic activity against leukemia cells (L1210), but only compounds
2 and
5 exhibited potent activity.
Chromatographic fractionations of the toluene extract of the heartwood of
Excoecaria parvifolia collected in Australia resulted in the isolation of 12 beyerane diterpenes (
1–
12), and the triterpene, lupeol. Four of the isolated diterpenoids (
5–
7 and
12) have unusual structures:
ent-3-oxa-beyer-15-en-2-one, (
5);
ent-15,16-epoxy-2-hydroxy-19-norbeyer-1,4-dien-3-one (
6); methyl
ent-2,4-seco-15,16-epoxy-4-oxo-3,19-dinorbeyer-15-en-2-oate (
7); and
ent-2,17-dihydroxy-19-norbeyer-1,4,15-trien-3-one (
12). The structures were established by spectroscopic analyses, NMR data comparisons with similar diterpenes, and chemical correlations. All the diterpenes are assumed to have the same absolute configuration as the co-occurring (+)-stachenol (
4). Diosphenol
2 and nor-lactone
5 exhibited significant potency in bioassays for cytotoxic activity against leukemia cells (L1210). Plausible biosynthetic pathways are proposed to explain the origin of the diterpene metabolites.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>17196627</pmid><doi>10.1016/j.phytochem.2006.11.010</doi><tpages>8</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0031-9422 |
| ispartof | Phytochemistry (Oxford), 2007-02, Vol.68 (4), p.546-553 |
| issn | 0031-9422 1873-3700 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_68989313 |
| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | anticarcinogenic activity beyerane diterpenes Biological and medical sciences Chemical constitution chemical structure cultured cells Cytotoxicity Diosphenols Diterpenes - chemistry Diterpenes - isolation & purification Diterpenoids ent-Beyeranes Euphorbiaceae Euphorbiaceae - chemistry Excoecaria Excoecaria parvifolia Fundamental and applied biological sciences. Psychology Heartwood L1210 lupeol mice Models, Molecular Molecular Structure phytochemicals Plant Oils - chemistry Plant physiology and development spectral analysis triterpenoids Wood |
| title | ent-Beyerane diterpenoids from the heartwood of Excoecaria parvifolia |
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