Two cyclopeptides from the seeds of Annona cherimola
The structures of cherimolacyclopeptides E and F were elucidated on the basis of their MS/MS spectra, chemical degradation and extensive 2D NMR experiments. Bioassay-guided fractionation of cytotoxic of methanol extract of the seeds of Annona cherimola provided two novel cyclic peptides, cherimolacy...
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| Veröffentlicht in: | Phytochemistry (Oxford) 2005-10, Vol.66 (19), p.2376-2380 |
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| container_title | Phytochemistry (Oxford) |
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| creator | Wélé, Alassane Zhang, Yanjun Brouard, Jean-Paul Pousset, Jean-Louis Bodo, Bernard |
| description | The structures of cherimolacyclopeptides E and F were elucidated on the basis of their MS/MS spectra, chemical degradation and extensive 2D NMR experiments.
Bioassay-guided fractionation of cytotoxic of methanol extract of the seeds of
Annona cherimola provided two novel cyclic peptides, cherimolacyclopeptide E (
1) and cherimolacyclopeptide F (
2), which exhibited significant cytotoxic activity against the KB (human nasopharyngeal carcinoma) cell culture system. The peptide
1 and
2 were elucidated by MS/MS fragmentation experiments using a Q-TOF mass spectrometer equipped with an ESI source, extensive 2D NMR analyses and chemical degradation. |
| doi_str_mv | 10.1016/j.phytochem.2005.06.011 |
| format | Article |
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Bioassay-guided fractionation of cytotoxic of methanol extract of the seeds of
Annona cherimola provided two novel cyclic peptides, cherimolacyclopeptide E (
1) and cherimolacyclopeptide F (
2), which exhibited significant cytotoxic activity against the KB (human nasopharyngeal carcinoma) cell culture system. The peptide
1 and
2 were elucidated by MS/MS fragmentation experiments using a Q-TOF mass spectrometer equipped with an ESI source, extensive 2D NMR analyses and chemical degradation.</description><identifier>ISSN: 0031-9422</identifier><identifier>EISSN: 1873-3700</identifier><identifier>DOI: 10.1016/j.phytochem.2005.06.011</identifier><identifier>PMID: 16040066</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>Amino Acid Sequence ; Analytical, structural and metabolic biochemistry ; Annona ; Annona - chemistry ; Annona cherimola ; Annonaceae ; Antineoplastic Agents, Phytogenic ; Antineoplastic Agents, Phytogenic - chemistry ; Antineoplastic Agents, Phytogenic - isolation & purification ; Antineoplastic Agents, Phytogenic - pharmacology ; Biochemistry ; Biochemistry, Molecular Biology ; Biological and medical sciences ; Cell Survival ; Cell Survival - drug effects ; Chemical constitution ; Chemical Sciences ; Cherimolacyclopeptide E ; Cherimolacyclopeptide F ; Cyclopeptide ; Drug Screening Assays, Antitumor ; Fundamental and applied biological sciences. Psychology ; Gas Chromatography-Mass Spectrometry ; Glycoproteins ; Humans ; Inhibitory Concentration 50 ; KB Cells ; Life Sciences ; Magnetic Resonance Spectroscopy ; Molecular Sequence Data ; Organic chemistry ; Peptides, Cyclic ; Peptides, Cyclic - chemistry ; Peptides, Cyclic - isolation & purification ; Peptides, Cyclic - pharmacology ; Plant physiology and development ; Proteins ; Seeds ; Seeds - chemistry ; Spectrometry, Mass, Electrospray Ionization</subject><ispartof>Phytochemistry (Oxford), 2005-10, Vol.66 (19), p.2376-2380</ispartof><rights>2005 Elsevier Ltd</rights><rights>2005 INIST-CNRS</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c433t-d9302fc9e94c5cf7bd828eedd8cc308a1d602a4e94f020f4cd21c0e7e931166d3</citedby><cites>FETCH-LOGICAL-c433t-d9302fc9e94c5cf7bd828eedd8cc308a1d602a4e94f020f4cd21c0e7e931166d3</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.2005.06.011$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>230,314,780,784,885,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=17163951$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16040066$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://hal.science/hal-00086268$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Wélé, Alassane</creatorcontrib><creatorcontrib>Zhang, Yanjun</creatorcontrib><creatorcontrib>Brouard, Jean-Paul</creatorcontrib><creatorcontrib>Pousset, Jean-Louis</creatorcontrib><creatorcontrib>Bodo, Bernard</creatorcontrib><title>Two cyclopeptides from the seeds of Annona cherimola</title><title>Phytochemistry (Oxford)</title><addtitle>Phytochemistry</addtitle><description>The structures of cherimolacyclopeptides E and F were elucidated on the basis of their MS/MS spectra, chemical degradation and extensive 2D NMR experiments.
Bioassay-guided fractionation of cytotoxic of methanol extract of the seeds of
Annona cherimola provided two novel cyclic peptides, cherimolacyclopeptide E (
1) and cherimolacyclopeptide F (
2), which exhibited significant cytotoxic activity against the KB (human nasopharyngeal carcinoma) cell culture system. The peptide
1 and
2 were elucidated by MS/MS fragmentation experiments using a Q-TOF mass spectrometer equipped with an ESI source, extensive 2D NMR analyses and chemical degradation.</description><subject>Amino Acid Sequence</subject><subject>Analytical, structural and metabolic biochemistry</subject><subject>Annona</subject><subject>Annona - chemistry</subject><subject>Annona cherimola</subject><subject>Annonaceae</subject><subject>Antineoplastic Agents, Phytogenic</subject><subject>Antineoplastic Agents, Phytogenic - chemistry</subject><subject>Antineoplastic Agents, Phytogenic - isolation & purification</subject><subject>Antineoplastic Agents, Phytogenic - pharmacology</subject><subject>Biochemistry</subject><subject>Biochemistry, Molecular Biology</subject><subject>Biological and medical sciences</subject><subject>Cell Survival</subject><subject>Cell Survival - drug effects</subject><subject>Chemical constitution</subject><subject>Chemical Sciences</subject><subject>Cherimolacyclopeptide E</subject><subject>Cherimolacyclopeptide F</subject><subject>Cyclopeptide</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Gas Chromatography-Mass Spectrometry</subject><subject>Glycoproteins</subject><subject>Humans</subject><subject>Inhibitory Concentration 50</subject><subject>KB Cells</subject><subject>Life Sciences</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Molecular Sequence Data</subject><subject>Organic chemistry</subject><subject>Peptides, Cyclic</subject><subject>Peptides, Cyclic - chemistry</subject><subject>Peptides, Cyclic - isolation & purification</subject><subject>Peptides, Cyclic - pharmacology</subject><subject>Plant physiology and development</subject><subject>Proteins</subject><subject>Seeds</subject><subject>Seeds - chemistry</subject><subject>Spectrometry, Mass, Electrospray Ionization</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>eNqFkLFOwzAQhi0EoqXwCpCFgSHhbKdOMlYVUKRKLGW23PNZTZXGURxAfXtctaIjkyX7-_87f4w9cMg4cPW8zbrNfvC4oV0mAKYZqAw4v2BjXhYylQXAJRsDSJ5WuRAjdhPCFiI4VeqajbiCHECpMctXPz7BPTa-o26oLYXE9X6XDBtKApENiXfJrG19a5I4ra93vjG37MqZJtDd6Zywz9eX1XyRLj_e3uezZYq5lENqKwnCYUVVjlN0xdqWooydtkSUUBpuFQiTx2cHAlyOVnAEKqiSnCtl5YQ9HXs3ptFdnG36vfam1ovZUh_u4o9KJVT5zSNbHFnsfQg9ub8AB31wprf6z5k-ONOgdHQWk_fHZPe13pE9506SIvB4AkxA07jetFiHM1dwJavpoWh25Cg6-a6p1wFrapFs3RMO2vr632V-AWLTjY8</recordid><startdate>20051001</startdate><enddate>20051001</enddate><creator>Wélé, Alassane</creator><creator>Zhang, Yanjun</creator><creator>Brouard, Jean-Paul</creator><creator>Pousset, Jean-Louis</creator><creator>Bodo, Bernard</creator><general>Elsevier Ltd</general><general>Elsevier</general><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>1XC</scope></search><sort><creationdate>20051001</creationdate><title>Two cyclopeptides from the seeds of Annona cherimola</title><author>Wélé, Alassane ; Zhang, Yanjun ; Brouard, Jean-Paul ; Pousset, Jean-Louis ; Bodo, Bernard</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c433t-d9302fc9e94c5cf7bd828eedd8cc308a1d602a4e94f020f4cd21c0e7e931166d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Amino Acid Sequence</topic><topic>Analytical, structural and metabolic biochemistry</topic><topic>Annona</topic><topic>Annona - chemistry</topic><topic>Annona cherimola</topic><topic>Annonaceae</topic><topic>Antineoplastic Agents, Phytogenic</topic><topic>Antineoplastic Agents, Phytogenic - chemistry</topic><topic>Antineoplastic Agents, Phytogenic - isolation & purification</topic><topic>Antineoplastic Agents, Phytogenic - pharmacology</topic><topic>Biochemistry</topic><topic>Biochemistry, Molecular Biology</topic><topic>Biological and medical sciences</topic><topic>Cell Survival</topic><topic>Cell Survival - drug effects</topic><topic>Chemical constitution</topic><topic>Chemical Sciences</topic><topic>Cherimolacyclopeptide E</topic><topic>Cherimolacyclopeptide F</topic><topic>Cyclopeptide</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Gas Chromatography-Mass Spectrometry</topic><topic>Glycoproteins</topic><topic>Humans</topic><topic>Inhibitory Concentration 50</topic><topic>KB Cells</topic><topic>Life Sciences</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Molecular Sequence Data</topic><topic>Organic chemistry</topic><topic>Peptides, Cyclic</topic><topic>Peptides, Cyclic - chemistry</topic><topic>Peptides, Cyclic - isolation & purification</topic><topic>Peptides, Cyclic - pharmacology</topic><topic>Plant physiology and development</topic><topic>Proteins</topic><topic>Seeds</topic><topic>Seeds - chemistry</topic><topic>Spectrometry, Mass, Electrospray Ionization</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wélé, Alassane</creatorcontrib><creatorcontrib>Zhang, Yanjun</creatorcontrib><creatorcontrib>Brouard, Jean-Paul</creatorcontrib><creatorcontrib>Pousset, Jean-Louis</creatorcontrib><creatorcontrib>Bodo, Bernard</creatorcontrib><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>Hyper Article en Ligne (HAL)</collection><jtitle>Phytochemistry (Oxford)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wélé, Alassane</au><au>Zhang, Yanjun</au><au>Brouard, Jean-Paul</au><au>Pousset, Jean-Louis</au><au>Bodo, Bernard</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Two cyclopeptides from the seeds of Annona cherimola</atitle><jtitle>Phytochemistry (Oxford)</jtitle><addtitle>Phytochemistry</addtitle><date>2005-10-01</date><risdate>2005</risdate><volume>66</volume><issue>19</issue><spage>2376</spage><epage>2380</epage><pages>2376-2380</pages><issn>0031-9422</issn><eissn>1873-3700</eissn><abstract>The structures of cherimolacyclopeptides E and F were elucidated on the basis of their MS/MS spectra, chemical degradation and extensive 2D NMR experiments.
Bioassay-guided fractionation of cytotoxic of methanol extract of the seeds of
Annona cherimola provided two novel cyclic peptides, cherimolacyclopeptide E (
1) and cherimolacyclopeptide F (
2), which exhibited significant cytotoxic activity against the KB (human nasopharyngeal carcinoma) cell culture system. The peptide
1 and
2 were elucidated by MS/MS fragmentation experiments using a Q-TOF mass spectrometer equipped with an ESI source, extensive 2D NMR analyses and chemical degradation.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>16040066</pmid><doi>10.1016/j.phytochem.2005.06.011</doi><tpages>5</tpages></addata></record> |
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| subjects | Amino Acid Sequence Analytical, structural and metabolic biochemistry Annona Annona - chemistry Annona cherimola Annonaceae Antineoplastic Agents, Phytogenic Antineoplastic Agents, Phytogenic - chemistry Antineoplastic Agents, Phytogenic - isolation & purification Antineoplastic Agents, Phytogenic - pharmacology Biochemistry Biochemistry, Molecular Biology Biological and medical sciences Cell Survival Cell Survival - drug effects Chemical constitution Chemical Sciences Cherimolacyclopeptide E Cherimolacyclopeptide F Cyclopeptide Drug Screening Assays, Antitumor Fundamental and applied biological sciences. Psychology Gas Chromatography-Mass Spectrometry Glycoproteins Humans Inhibitory Concentration 50 KB Cells Life Sciences Magnetic Resonance Spectroscopy Molecular Sequence Data Organic chemistry Peptides, Cyclic Peptides, Cyclic - chemistry Peptides, Cyclic - isolation & purification Peptides, Cyclic - pharmacology Plant physiology and development Proteins Seeds Seeds - chemistry Spectrometry, Mass, Electrospray Ionization |
| title | Two cyclopeptides from the seeds of Annona cherimola |
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