Cytotoxic epimeric withaphysalins from leaves of Acnistus arborescens
Abstract Phytochemical analysis of the leaves of ACNISTUS ARBORESCENS (Solanaceae) resulted in the isolation of two new epimeric withaphysalins (17S,20R,22R)-5β,6β:18,20-diepoxy-4β,18-dihydroxy-1-oxowitha-24-enolide (2, 18R and 18S), together with the known withaphysalin F (1, 18R and 18S). Their st...
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| Veröffentlicht in: | Planta medica 2004-06, Vol.70 (6), p.551-555 |
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| creator | Veras, M.L Bezerra, M.Z.B Braz-Filho, R Pessoa, O.D.L Montenegro, R.C Pessoa, C. do O Moraes, M.O. de Costa-Lotufo, L.V |
| description | Abstract
Phytochemical analysis of the leaves of ACNISTUS ARBORESCENS (Solanaceae) resulted in the isolation of two new epimeric withaphysalins (17S,20R,22R)-5β,6β:18,20-diepoxy-4β,18-dihydroxy-1-oxowitha-24-enolide (2, 18R and 18S), together with the known withaphysalin F (1, 18R and 18S). Their structures were established by spectroscopic methods, including 2D NMR data and comparison with literature data. Compounds 1 and 2 displayed potent cytotoxic activities against several cancer cell lines with IC
50
values in the range of 0.20 to 1.46 μg/mL for 1 and 0.89 to 8.08 μg/mL for 2. The strong cytotoxicity presented by 1 suggests that in this series of compounds, the 2,3-unsaturated ketone moiety is an important pharmacophoric unit. The cytotoxic activity seemed to be related to DNA synthesis inhibition, as revealed by the reduction of 5-bromo-2′-deoxyuridine incorporation after 24 hours of incubation on leukemic cells. |
| doi_str_mv | 10.1055/s-2004-827156 |
| format | Article |
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Phytochemical analysis of the leaves of ACNISTUS ARBORESCENS (Solanaceae) resulted in the isolation of two new epimeric withaphysalins (17S,20R,22R)-5β,6β:18,20-diepoxy-4β,18-dihydroxy-1-oxowitha-24-enolide (2, 18R and 18S), together with the known withaphysalin F (1, 18R and 18S). Their structures were established by spectroscopic methods, including 2D NMR data and comparison with literature data. Compounds 1 and 2 displayed potent cytotoxic activities against several cancer cell lines with IC
50
values in the range of 0.20 to 1.46 μg/mL for 1 and 0.89 to 8.08 μg/mL for 2. The strong cytotoxicity presented by 1 suggests that in this series of compounds, the 2,3-unsaturated ketone moiety is an important pharmacophoric unit. The cytotoxic activity seemed to be related to DNA synthesis inhibition, as revealed by the reduction of 5-bromo-2′-deoxyuridine incorporation after 24 hours of incubation on leukemic cells.</description><identifier>ISSN: 0032-0943</identifier><identifier>EISSN: 1439-0221</identifier><identifier>DOI: 10.1055/s-2004-827156</identifier><identifier>PMID: 15241891</identifier><identifier>CODEN: PLMEAA</identifier><language>eng</language><publisher>Stuttgart: Thieme</publisher><subject>Acnistus arborescens ; anticarcinogenic activity ; Antineoplastic Agents, Phytogenic - administration & dosage ; Antineoplastic Agents, Phytogenic - chemistry ; Antineoplastic Agents, Phytogenic - pharmacology ; Antineoplastic Agents, Phytogenic - therapeutic use ; Biological and medical sciences ; Cell Line, Tumor - drug effects ; cell lines ; chemical structure ; cytotoxicity ; epimers ; Ergosterol - analogs & derivatives ; Ergosterol - chemistry ; Ergosterol - pharmacology ; General pharmacology ; HL-60 Cells - drug effects ; Humans ; leaves ; Medical sciences ; Original Paper ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments ; phytochemicals ; Phytotherapy ; plant extracts ; Plant Extracts - administration & dosage ; Plant Extracts - chemistry ; Plant Extracts - pharmacology ; Plant Extracts - therapeutic use ; Plant Leaves ; Racemases and Epimerases ; Secosteroids - chemistry ; Secosteroids - pharmacology ; Solanaceae ; spectral analysis ; stereochemistry ; steroids ; withaphysalin</subject><ispartof>Planta medica, 2004-06, Vol.70 (6), p.551-555</ispartof><rights>Georg Thieme Verlag KG Stuttgart · New York</rights><rights>2004 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c342t-77d069a0846858812b2d2394d3f2e2546de8aca7d52e2c33d55e3546eedb26033</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-2004-827156.pdf$$EPDF$$P50$$Gthieme$$H</linktopdf><linktohtml>$$Uhttps://www.thieme-connect.de/products/ejournals/html/10.1055/s-2004-827156$$EHTML$$P50$$Gthieme$$H</linktohtml><link.rule.ids>314,776,780,3005,27901,27902,54534,54535</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=15884478$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15241891$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Veras, M.L</creatorcontrib><creatorcontrib>Bezerra, M.Z.B</creatorcontrib><creatorcontrib>Braz-Filho, R</creatorcontrib><creatorcontrib>Pessoa, O.D.L</creatorcontrib><creatorcontrib>Montenegro, R.C</creatorcontrib><creatorcontrib>Pessoa, C. do O</creatorcontrib><creatorcontrib>Moraes, M.O. de</creatorcontrib><creatorcontrib>Costa-Lotufo, L.V</creatorcontrib><title>Cytotoxic epimeric withaphysalins from leaves of Acnistus arborescens</title><title>Planta medica</title><addtitle>Planta Med</addtitle><description>Abstract
Phytochemical analysis of the leaves of ACNISTUS ARBORESCENS (Solanaceae) resulted in the isolation of two new epimeric withaphysalins (17S,20R,22R)-5β,6β:18,20-diepoxy-4β,18-dihydroxy-1-oxowitha-24-enolide (2, 18R and 18S), together with the known withaphysalin F (1, 18R and 18S). Their structures were established by spectroscopic methods, including 2D NMR data and comparison with literature data. Compounds 1 and 2 displayed potent cytotoxic activities against several cancer cell lines with IC
50
values in the range of 0.20 to 1.46 μg/mL for 1 and 0.89 to 8.08 μg/mL for 2. The strong cytotoxicity presented by 1 suggests that in this series of compounds, the 2,3-unsaturated ketone moiety is an important pharmacophoric unit. The cytotoxic activity seemed to be related to DNA synthesis inhibition, as revealed by the reduction of 5-bromo-2′-deoxyuridine incorporation after 24 hours of incubation on leukemic cells.</description><subject>Acnistus arborescens</subject><subject>anticarcinogenic activity</subject><subject>Antineoplastic Agents, Phytogenic - administration & dosage</subject><subject>Antineoplastic Agents, Phytogenic - chemistry</subject><subject>Antineoplastic Agents, Phytogenic - pharmacology</subject><subject>Antineoplastic Agents, Phytogenic - therapeutic use</subject><subject>Biological and medical sciences</subject><subject>Cell Line, Tumor - drug effects</subject><subject>cell lines</subject><subject>chemical structure</subject><subject>cytotoxicity</subject><subject>epimers</subject><subject>Ergosterol - analogs & derivatives</subject><subject>Ergosterol - chemistry</subject><subject>Ergosterol - pharmacology</subject><subject>General pharmacology</subject><subject>HL-60 Cells - drug effects</subject><subject>Humans</subject><subject>leaves</subject><subject>Medical sciences</subject><subject>Original Paper</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>phytochemicals</subject><subject>Phytotherapy</subject><subject>plant extracts</subject><subject>Plant Extracts - administration & dosage</subject><subject>Plant Extracts - chemistry</subject><subject>Plant Extracts - pharmacology</subject><subject>Plant Extracts - therapeutic use</subject><subject>Plant Leaves</subject><subject>Racemases and Epimerases</subject><subject>Secosteroids - chemistry</subject><subject>Secosteroids - pharmacology</subject><subject>Solanaceae</subject><subject>spectral analysis</subject><subject>stereochemistry</subject><subject>steroids</subject><subject>withaphysalin</subject><issn>0032-0943</issn><issn>1439-0221</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpN0TtPwzAUBWALgWh5jKyQBSYC16_EGauKl4TEAMyWk9xQV0lc7ATov8dVi8Tkhz4d-R4TckbhhoKUtyFlACJVLKcy2yNTKniRAmN0n0wBOEuhEHxCjkJYAlBRABySCZVMUFXQKbmbrwc3uB9bJbiyHfq4-bbDwqwW62Ba24ek8a5LWjRfGBLXJLOqt2EYQ2J86TyGCvtwQg4a0wY83a3H5P3-7m3-mD6_PDzNZ89pxQUb0jyvISsMKJEpqRRlJasZL0TNG4ZMiqxGZSqT1zIeK85rKZHHa8S6ZBlwfkyutrkr7z5HDIPubHxA25oe3Rh0lsVgUWzg-Q6OZYe1XnnbGb_Wf4NHcLkDJlSmbbzpKxv-OaWEyFV011s3LCx2qJdu9H0cUVPQm_510Jv-9bb_yC-2vDFOmw8fI99fGVAO8RuE4jn_BaxKfYo</recordid><startdate>20040601</startdate><enddate>20040601</enddate><creator>Veras, M.L</creator><creator>Bezerra, M.Z.B</creator><creator>Braz-Filho, R</creator><creator>Pessoa, O.D.L</creator><creator>Montenegro, R.C</creator><creator>Pessoa, C. do O</creator><creator>Moraes, M.O. de</creator><creator>Costa-Lotufo, L.V</creator><general>Thieme</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>7X8</scope></search><sort><creationdate>20040601</creationdate><title>Cytotoxic epimeric withaphysalins from leaves of Acnistus arborescens</title><author>Veras, M.L ; Bezerra, M.Z.B ; Braz-Filho, R ; Pessoa, O.D.L ; Montenegro, R.C ; Pessoa, C. do O ; Moraes, M.O. de ; Costa-Lotufo, L.V</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c342t-77d069a0846858812b2d2394d3f2e2546de8aca7d52e2c33d55e3546eedb26033</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Acnistus arborescens</topic><topic>anticarcinogenic activity</topic><topic>Antineoplastic Agents, Phytogenic - administration & dosage</topic><topic>Antineoplastic Agents, Phytogenic - chemistry</topic><topic>Antineoplastic Agents, Phytogenic - pharmacology</topic><topic>Antineoplastic Agents, Phytogenic - therapeutic use</topic><topic>Biological and medical sciences</topic><topic>Cell Line, Tumor - drug effects</topic><topic>cell lines</topic><topic>chemical structure</topic><topic>cytotoxicity</topic><topic>epimers</topic><topic>Ergosterol - analogs & derivatives</topic><topic>Ergosterol - chemistry</topic><topic>Ergosterol - pharmacology</topic><topic>General pharmacology</topic><topic>HL-60 Cells - drug effects</topic><topic>Humans</topic><topic>leaves</topic><topic>Medical sciences</topic><topic>Original Paper</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>phytochemicals</topic><topic>Phytotherapy</topic><topic>plant extracts</topic><topic>Plant Extracts - administration & dosage</topic><topic>Plant Extracts - chemistry</topic><topic>Plant Extracts - pharmacology</topic><topic>Plant Extracts - therapeutic use</topic><topic>Plant Leaves</topic><topic>Racemases and Epimerases</topic><topic>Secosteroids - chemistry</topic><topic>Secosteroids - pharmacology</topic><topic>Solanaceae</topic><topic>spectral analysis</topic><topic>stereochemistry</topic><topic>steroids</topic><topic>withaphysalin</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Veras, M.L</creatorcontrib><creatorcontrib>Bezerra, M.Z.B</creatorcontrib><creatorcontrib>Braz-Filho, R</creatorcontrib><creatorcontrib>Pessoa, O.D.L</creatorcontrib><creatorcontrib>Montenegro, R.C</creatorcontrib><creatorcontrib>Pessoa, C. do O</creatorcontrib><creatorcontrib>Moraes, M.O. de</creatorcontrib><creatorcontrib>Costa-Lotufo, L.V</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>MEDLINE - Academic</collection><jtitle>Planta medica</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Veras, M.L</au><au>Bezerra, M.Z.B</au><au>Braz-Filho, R</au><au>Pessoa, O.D.L</au><au>Montenegro, R.C</au><au>Pessoa, C. do O</au><au>Moraes, M.O. de</au><au>Costa-Lotufo, L.V</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Cytotoxic epimeric withaphysalins from leaves of Acnistus arborescens</atitle><jtitle>Planta medica</jtitle><addtitle>Planta Med</addtitle><date>2004-06-01</date><risdate>2004</risdate><volume>70</volume><issue>6</issue><spage>551</spage><epage>555</epage><pages>551-555</pages><issn>0032-0943</issn><eissn>1439-0221</eissn><coden>PLMEAA</coden><abstract>Abstract
Phytochemical analysis of the leaves of ACNISTUS ARBORESCENS (Solanaceae) resulted in the isolation of two new epimeric withaphysalins (17S,20R,22R)-5β,6β:18,20-diepoxy-4β,18-dihydroxy-1-oxowitha-24-enolide (2, 18R and 18S), together with the known withaphysalin F (1, 18R and 18S). Their structures were established by spectroscopic methods, including 2D NMR data and comparison with literature data. Compounds 1 and 2 displayed potent cytotoxic activities against several cancer cell lines with IC
50
values in the range of 0.20 to 1.46 μg/mL for 1 and 0.89 to 8.08 μg/mL for 2. The strong cytotoxicity presented by 1 suggests that in this series of compounds, the 2,3-unsaturated ketone moiety is an important pharmacophoric unit. The cytotoxic activity seemed to be related to DNA synthesis inhibition, as revealed by the reduction of 5-bromo-2′-deoxyuridine incorporation after 24 hours of incubation on leukemic cells.</abstract><cop>Stuttgart</cop><cop>New York, NY</cop><pub>Thieme</pub><pmid>15241891</pmid><doi>10.1055/s-2004-827156</doi><tpages>5</tpages></addata></record> |
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| subjects | Acnistus arborescens anticarcinogenic activity Antineoplastic Agents, Phytogenic - administration & dosage Antineoplastic Agents, Phytogenic - chemistry Antineoplastic Agents, Phytogenic - pharmacology Antineoplastic Agents, Phytogenic - therapeutic use Biological and medical sciences Cell Line, Tumor - drug effects cell lines chemical structure cytotoxicity epimers Ergosterol - analogs & derivatives Ergosterol - chemistry Ergosterol - pharmacology General pharmacology HL-60 Cells - drug effects Humans leaves Medical sciences Original Paper Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments phytochemicals Phytotherapy plant extracts Plant Extracts - administration & dosage Plant Extracts - chemistry Plant Extracts - pharmacology Plant Extracts - therapeutic use Plant Leaves Racemases and Epimerases Secosteroids - chemistry Secosteroids - pharmacology Solanaceae spectral analysis stereochemistry steroids withaphysalin |
| title | Cytotoxic epimeric withaphysalins from leaves of Acnistus arborescens |
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