Structure, chemistry, and biological activity of pseudophomins A and B, new cyclic lipodepsipeptides isolated from the biocontrol bacterium Pseudomonas fluorescens
Pseudophomins A and B are cyclic lipodepsipeptides isolated from Pseudomonas fluorescens strain BRG100, a bacterium with potential application for biocontrol of plant pathogens and weeds. Their chemical structures were established by a combination of spectroscopic data, X-ray crystallography, and se...
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| Veröffentlicht in: | Phytochemistry (Oxford) 2003-04, Vol.62 (7), p.1105-1114 |
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| creator | Pedras, M.Soledade C Ismail, Nargis Quail, J.Wilson Boyetchko, Susan M |
| description | Pseudophomins A and B are cyclic lipodepsipeptides isolated from
Pseudomonas fluorescens strain BRG100, a bacterium with potential application for biocontrol of plant pathogens and weeds. Their chemical structures were established by a combination of spectroscopic data, X-ray crystallography, and selective chemical degradation. This unique chemical degradation allowed the unambiguous determination of the absolute configuration of the amino acid residue Leu-1, due to γ-lactam formation followed by selective cleavage of the adjacent N(8)–C(7) bond. To the best of our knowledge this is the first application of γ-lactam formation to the determination of absolute configuration of an adjacent amino acid. Pseudophomin B showed higher antifungal activity against the phytopathogens
Phoma lingam/Leptosphaeria maculans and
Sclerotinia sclerotiorum than pseudophomin A, and is likely to be the main component responsible for the antifungal activity of EtOAc extracts of strain BRG100. By contrast, pseudophomin A showed stronger inhibition of green foxtail (
Setaria viridis) root germination than pseudophomin B.
The chemical structures of pseudophomins A and B were established by a combination of spectroscopic data, X-ray crystallography, and selective chemical degradation. |
| doi_str_mv | 10.1016/S0031-9422(02)00617-9 |
| format | Article |
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Pseudomonas fluorescens strain BRG100, a bacterium with potential application for biocontrol of plant pathogens and weeds. Their chemical structures were established by a combination of spectroscopic data, X-ray crystallography, and selective chemical degradation. This unique chemical degradation allowed the unambiguous determination of the absolute configuration of the amino acid residue Leu-1, due to γ-lactam formation followed by selective cleavage of the adjacent N(8)–C(7) bond. To the best of our knowledge this is the first application of γ-lactam formation to the determination of absolute configuration of an adjacent amino acid. Pseudophomin B showed higher antifungal activity against the phytopathogens
Phoma lingam/Leptosphaeria maculans and
Sclerotinia sclerotiorum than pseudophomin A, and is likely to be the main component responsible for the antifungal activity of EtOAc extracts of strain BRG100. By contrast, pseudophomin A showed stronger inhibition of green foxtail (
Setaria viridis) root germination than pseudophomin B.
The chemical structures of pseudophomins A and B were established by a combination of spectroscopic data, X-ray crystallography, and selective chemical degradation.</description><identifier>ISSN: 0031-9422</identifier><identifier>EISSN: 1873-3700</identifier><identifier>DOI: 10.1016/S0031-9422(02)00617-9</identifier><identifier>PMID: 12591264</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>Alternaria - drug effects ; Antifungal ; Antifungal Agents - chemistry ; Antifungal Agents - pharmacology ; Ascomycota - drug effects ; Biocontrol ; Biological and medical sciences ; Biological control ; Chemical control ; Control ; Crystallography, X-Ray ; Depsipeptide ; Fundamental and applied biological sciences. Psychology ; Fungal plant pathogens ; Herbicides - chemistry ; Herbicides - pharmacology ; Leptosphaeria maculans ; Lipodepsipeptide ; Nuclear Magnetic Resonance, Biomolecular ; Parasitic plants. Weeds ; Peptides, Cyclic - chemistry ; Peptides, Cyclic - pharmacology ; Phoma lingam ; Phytopathology. Animal pests. Plant and forest protection ; Plant Roots - drug effects ; Plant Roots - growth & development ; Protein Conformation ; Pseudomonas fluorescens ; Pseudomonas fluorescens - chemistry ; Pseudomonas fluorescens - classification ; Rhizoctonia - drug effects ; Sclerotinia sclerotiorum ; Setaria Plant - drug effects ; Weeds</subject><ispartof>Phytochemistry (Oxford), 2003-04, Vol.62 (7), p.1105-1114</ispartof><rights>2003 Elsevier Science Ltd</rights><rights>2003 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c474t-3ca17dee2a1600083e31200890fca9acee6b32297ac665e45c6a3ba45c2fc9443</citedby><cites>FETCH-LOGICAL-c474t-3ca17dee2a1600083e31200890fca9acee6b32297ac665e45c6a3ba45c2fc9443</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0031942202006179$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=14659838$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12591264$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Pedras, M.Soledade C</creatorcontrib><creatorcontrib>Ismail, Nargis</creatorcontrib><creatorcontrib>Quail, J.Wilson</creatorcontrib><creatorcontrib>Boyetchko, Susan M</creatorcontrib><title>Structure, chemistry, and biological activity of pseudophomins A and B, new cyclic lipodepsipeptides isolated from the biocontrol bacterium Pseudomonas fluorescens</title><title>Phytochemistry (Oxford)</title><addtitle>Phytochemistry</addtitle><description>Pseudophomins A and B are cyclic lipodepsipeptides isolated from
Pseudomonas fluorescens strain BRG100, a bacterium with potential application for biocontrol of plant pathogens and weeds. Their chemical structures were established by a combination of spectroscopic data, X-ray crystallography, and selective chemical degradation. This unique chemical degradation allowed the unambiguous determination of the absolute configuration of the amino acid residue Leu-1, due to γ-lactam formation followed by selective cleavage of the adjacent N(8)–C(7) bond. To the best of our knowledge this is the first application of γ-lactam formation to the determination of absolute configuration of an adjacent amino acid. Pseudophomin B showed higher antifungal activity against the phytopathogens
Phoma lingam/Leptosphaeria maculans and
Sclerotinia sclerotiorum than pseudophomin A, and is likely to be the main component responsible for the antifungal activity of EtOAc extracts of strain BRG100. By contrast, pseudophomin A showed stronger inhibition of green foxtail (
Setaria viridis) root germination than pseudophomin B.
The chemical structures of pseudophomins A and B were established by a combination of spectroscopic data, X-ray crystallography, and selective chemical degradation.</description><subject>Alternaria - drug effects</subject><subject>Antifungal</subject><subject>Antifungal Agents - chemistry</subject><subject>Antifungal Agents - pharmacology</subject><subject>Ascomycota - drug effects</subject><subject>Biocontrol</subject><subject>Biological and medical sciences</subject><subject>Biological control</subject><subject>Chemical control</subject><subject>Control</subject><subject>Crystallography, X-Ray</subject><subject>Depsipeptide</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Fungal plant pathogens</subject><subject>Herbicides - chemistry</subject><subject>Herbicides - pharmacology</subject><subject>Leptosphaeria maculans</subject><subject>Lipodepsipeptide</subject><subject>Nuclear Magnetic Resonance, Biomolecular</subject><subject>Parasitic plants. Weeds</subject><subject>Peptides, Cyclic - chemistry</subject><subject>Peptides, Cyclic - pharmacology</subject><subject>Phoma lingam</subject><subject>Phytopathology. Animal pests. Plant and forest protection</subject><subject>Plant Roots - drug effects</subject><subject>Plant Roots - growth & development</subject><subject>Protein Conformation</subject><subject>Pseudomonas fluorescens</subject><subject>Pseudomonas fluorescens - chemistry</subject><subject>Pseudomonas fluorescens - classification</subject><subject>Rhizoctonia - drug effects</subject><subject>Sclerotinia sclerotiorum</subject><subject>Setaria Plant - drug effects</subject><subject>Weeds</subject><issn>0031-9422</issn><issn>1873-3700</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkc1u1TAQhS0EopfCI4C8AYF0A_5JnGSFSlVopUpFKqwtZzLhGjlxsJ2i-zx90fr-iC6RLJ3NN2c85xDymrOPnHH16ZYxyYu2FOI9Ex8YU7wu2idkxZtaFrJm7ClZ_UNOyIsYfzPGqkqp5-SEi6rlQpUrcn-bwgJpCbimsMHRxhS2a2qmnnbWO__LgnHUQLJ3Nm2pH-gccen9vPGjnSI926Nf1nTCvxS24CxQZ2ff4xztjHOyPUZqo3cmYU-H4EeaNrgzBz-l4B3tsjsGu4z0-9569JOJdHCLDxgBp_iSPBuMi_jqqKfk59eLH-eXxfXNt6vzs-sCyrpMhQTD6x5RGK7yqY1EyUXWlg1gWgOIqpNCtLUBpSosK1BGdiarGKAtS3lK3h185-D_LBiTznEAOmcm9EvUvFG1yNlnsDqAEHyMAQc9BzuasNWc6V07et-O3kWvWX67dnSb594cFyzdiP3j1LGODLw9Aibm3IdgJrDxkStV1TayydznA4c5jjuLQUewOAH2NiAk3Xv7n688AFsCsBQ</recordid><startdate>20030401</startdate><enddate>20030401</enddate><creator>Pedras, M.Soledade C</creator><creator>Ismail, Nargis</creator><creator>Quail, J.Wilson</creator><creator>Boyetchko, Susan M</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>7T7</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope></search><sort><creationdate>20030401</creationdate><title>Structure, chemistry, and biological activity of pseudophomins A and B, new cyclic lipodepsipeptides isolated from the biocontrol bacterium Pseudomonas fluorescens</title><author>Pedras, M.Soledade C ; Ismail, Nargis ; Quail, J.Wilson ; Boyetchko, Susan M</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c474t-3ca17dee2a1600083e31200890fca9acee6b32297ac665e45c6a3ba45c2fc9443</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>Alternaria - drug effects</topic><topic>Antifungal</topic><topic>Antifungal Agents - chemistry</topic><topic>Antifungal Agents - pharmacology</topic><topic>Ascomycota - drug effects</topic><topic>Biocontrol</topic><topic>Biological and medical sciences</topic><topic>Biological control</topic><topic>Chemical control</topic><topic>Control</topic><topic>Crystallography, X-Ray</topic><topic>Depsipeptide</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Fungal plant pathogens</topic><topic>Herbicides - chemistry</topic><topic>Herbicides - pharmacology</topic><topic>Leptosphaeria maculans</topic><topic>Lipodepsipeptide</topic><topic>Nuclear Magnetic Resonance, Biomolecular</topic><topic>Parasitic plants. Weeds</topic><topic>Peptides, Cyclic - chemistry</topic><topic>Peptides, Cyclic - pharmacology</topic><topic>Phoma lingam</topic><topic>Phytopathology. Animal pests. Plant and forest protection</topic><topic>Plant Roots - drug effects</topic><topic>Plant Roots - growth & development</topic><topic>Protein Conformation</topic><topic>Pseudomonas fluorescens</topic><topic>Pseudomonas fluorescens - chemistry</topic><topic>Pseudomonas fluorescens - classification</topic><topic>Rhizoctonia - drug effects</topic><topic>Sclerotinia sclerotiorum</topic><topic>Setaria Plant - drug effects</topic><topic>Weeds</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Pedras, M.Soledade C</creatorcontrib><creatorcontrib>Ismail, Nargis</creatorcontrib><creatorcontrib>Quail, J.Wilson</creatorcontrib><creatorcontrib>Boyetchko, Susan M</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>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Phytochemistry (Oxford)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Pedras, M.Soledade C</au><au>Ismail, Nargis</au><au>Quail, J.Wilson</au><au>Boyetchko, Susan M</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Structure, chemistry, and biological activity of pseudophomins A and B, new cyclic lipodepsipeptides isolated from the biocontrol bacterium Pseudomonas fluorescens</atitle><jtitle>Phytochemistry (Oxford)</jtitle><addtitle>Phytochemistry</addtitle><date>2003-04-01</date><risdate>2003</risdate><volume>62</volume><issue>7</issue><spage>1105</spage><epage>1114</epage><pages>1105-1114</pages><issn>0031-9422</issn><eissn>1873-3700</eissn><abstract>Pseudophomins A and B are cyclic lipodepsipeptides isolated from
Pseudomonas fluorescens strain BRG100, a bacterium with potential application for biocontrol of plant pathogens and weeds. Their chemical structures were established by a combination of spectroscopic data, X-ray crystallography, and selective chemical degradation. This unique chemical degradation allowed the unambiguous determination of the absolute configuration of the amino acid residue Leu-1, due to γ-lactam formation followed by selective cleavage of the adjacent N(8)–C(7) bond. To the best of our knowledge this is the first application of γ-lactam formation to the determination of absolute configuration of an adjacent amino acid. Pseudophomin B showed higher antifungal activity against the phytopathogens
Phoma lingam/Leptosphaeria maculans and
Sclerotinia sclerotiorum than pseudophomin A, and is likely to be the main component responsible for the antifungal activity of EtOAc extracts of strain BRG100. By contrast, pseudophomin A showed stronger inhibition of green foxtail (
Setaria viridis) root germination than pseudophomin B.
The chemical structures of pseudophomins A and B were established by a combination of spectroscopic data, X-ray crystallography, and selective chemical degradation.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>12591264</pmid><doi>10.1016/S0031-9422(02)00617-9</doi><tpages>10</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0031-9422 |
| ispartof | Phytochemistry (Oxford), 2003-04, Vol.62 (7), p.1105-1114 |
| issn | 0031-9422 1873-3700 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_18672016 |
| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | Alternaria - drug effects Antifungal Antifungal Agents - chemistry Antifungal Agents - pharmacology Ascomycota - drug effects Biocontrol Biological and medical sciences Biological control Chemical control Control Crystallography, X-Ray Depsipeptide Fundamental and applied biological sciences. Psychology Fungal plant pathogens Herbicides - chemistry Herbicides - pharmacology Leptosphaeria maculans Lipodepsipeptide Nuclear Magnetic Resonance, Biomolecular Parasitic plants. Weeds Peptides, Cyclic - chemistry Peptides, Cyclic - pharmacology Phoma lingam Phytopathology. Animal pests. Plant and forest protection Plant Roots - drug effects Plant Roots - growth & development Protein Conformation Pseudomonas fluorescens Pseudomonas fluorescens - chemistry Pseudomonas fluorescens - classification Rhizoctonia - drug effects Sclerotinia sclerotiorum Setaria Plant - drug effects Weeds |
| title | Structure, chemistry, and biological activity of pseudophomins A and B, new cyclic lipodepsipeptides isolated from the biocontrol bacterium Pseudomonas fluorescens |
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