Eutypa Dieback in Grapevines: Differential Production of Acetylenic Phenol Metabolites by Strains of Eutypa lata
The production of acetylenic phenol metabolites in vitro by three strains of the ascomycete Eutypa lata, the causative agent of dying-arm disease in grapevines, has been investigated. Metabolite composition and yields differed significantly between strains and with growth medium but usually reached...
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| Veröffentlicht in: | Journal of agricultural and food chemistry 2002-03, Vol.50 (6), p.1393-1399 |
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| creator | Molyneux, Russell J Mahoney, Noreen Bayman, Paul Wong, Rosalind Y Meyer, Kenneth Irelan, Nancy |
| description | The production of acetylenic phenol metabolites in vitro by three strains of the ascomycete Eutypa lata, the causative agent of dying-arm disease in grapevines, has been investigated. Metabolite composition and yields differed significantly between strains and with growth medium but usually reached a maximum after 24−30 days of fungal growth. A general method for the analysis and identification of metabolites by gas chromatography/mass spectrometry of their trimethylsilyl ether derivatives was developed and individual compounds were quantitated by analytical high-performance liquid chromatography (HPLC) and separated by preparative HPLC. The phenolic aldehyde, eutypine (1), reported to be the grape phytotoxin, occurred in only one of the strains examined whereas the primary metabolite was the corresponding alcohol, eutypinol (2), the presumptive detoxification product. A novel metabolite was isolated as a major constituent, together with a minor component, and their structures were established by spectroscopic methods as a methoxyquinol, named eulatinol (4), and a chromene analog (9) of 2, respectively. The evidence suggests that 1 is not solely responsible for phytotoxicity in grapevines but that dying-arm disease may result from a suite of compounds elaborated by the fungus, with the composition dependent on fungal strain and nutritional source. Keywords: Grapes; Vitis vinifera; Eutypa lata; dieback; eutyposis; vine decline; dying-arm disease; chromene |
| doi_str_mv | 10.1021/jf011215a |
| format | Article |
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Metabolite composition and yields differed significantly between strains and with growth medium but usually reached a maximum after 24−30 days of fungal growth. A general method for the analysis and identification of metabolites by gas chromatography/mass spectrometry of their trimethylsilyl ether derivatives was developed and individual compounds were quantitated by analytical high-performance liquid chromatography (HPLC) and separated by preparative HPLC. The phenolic aldehyde, eutypine (1), reported to be the grape phytotoxin, occurred in only one of the strains examined whereas the primary metabolite was the corresponding alcohol, eutypinol (2), the presumptive detoxification product. A novel metabolite was isolated as a major constituent, together with a minor component, and their structures were established by spectroscopic methods as a methoxyquinol, named eulatinol (4), and a chromene analog (9) of 2, respectively. The evidence suggests that 1 is not solely responsible for phytotoxicity in grapevines but that dying-arm disease may result from a suite of compounds elaborated by the fungus, with the composition dependent on fungal strain and nutritional source. Keywords: Grapes; Vitis vinifera; Eutypa lata; dieback; eutyposis; vine decline; dying-arm disease; chromene</description><identifier>ISSN: 0021-8561</identifier><identifier>EISSN: 1520-5118</identifier><identifier>DOI: 10.1021/jf011215a</identifier><identifier>PMID: 11879009</identifier><identifier>CODEN: JAFCAU</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Alkynes ; Ascomycota - metabolism ; Benzaldehydes - analysis ; Benzaldehydes - metabolism ; Biological and medical sciences ; Chromatography, High Pressure Liquid - methods ; Fundamental and applied biological sciences. Psychology ; Fungal plant pathogens ; Gas Chromatography-Mass Spectrometry - methods ; Hydrogen-Ion Concentration ; Mycotoxins - metabolism ; Pathology, epidemiology, host-fungus relationships. Damages, economic importance ; Phenols - metabolism ; Phytopathology. Animal pests. 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Agric. Food Chem</addtitle><description>The production of acetylenic phenol metabolites in vitro by three strains of the ascomycete Eutypa lata, the causative agent of dying-arm disease in grapevines, has been investigated. Metabolite composition and yields differed significantly between strains and with growth medium but usually reached a maximum after 24−30 days of fungal growth. A general method for the analysis and identification of metabolites by gas chromatography/mass spectrometry of their trimethylsilyl ether derivatives was developed and individual compounds were quantitated by analytical high-performance liquid chromatography (HPLC) and separated by preparative HPLC. The phenolic aldehyde, eutypine (1), reported to be the grape phytotoxin, occurred in only one of the strains examined whereas the primary metabolite was the corresponding alcohol, eutypinol (2), the presumptive detoxification product. A novel metabolite was isolated as a major constituent, together with a minor component, and their structures were established by spectroscopic methods as a methoxyquinol, named eulatinol (4), and a chromene analog (9) of 2, respectively. The evidence suggests that 1 is not solely responsible for phytotoxicity in grapevines but that dying-arm disease may result from a suite of compounds elaborated by the fungus, with the composition dependent on fungal strain and nutritional source. Keywords: Grapes; Vitis vinifera; Eutypa lata; dieback; eutyposis; vine decline; dying-arm disease; chromene</description><subject>Alkynes</subject><subject>Ascomycota - metabolism</subject><subject>Benzaldehydes - analysis</subject><subject>Benzaldehydes - metabolism</subject><subject>Biological and medical sciences</subject><subject>Chromatography, High Pressure Liquid - methods</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Fungal plant pathogens</subject><subject>Gas Chromatography-Mass Spectrometry - methods</subject><subject>Hydrogen-Ion Concentration</subject><subject>Mycotoxins - metabolism</subject><subject>Pathology, epidemiology, host-fungus relationships. Damages, economic importance</subject><subject>Phenols - metabolism</subject><subject>Phytopathology. Animal pests. Plant and forest protection</subject><subject>Plant Diseases - microbiology</subject><subject>Vitis - microbiology</subject><issn>0021-8561</issn><issn>1520-5118</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2002</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0LFuFDEQBmALgcgRKHgB5IaCYoO9Xq-9dFFIjkghOSVHbY29Y-HLxnuyfYjr0vKaPAkb3SnXUE3xf5oZ_YS85-yEs5p_XnnGec0lvCAzLmtWSc71SzJjU1hp2fIj8ibnFWNMS8Vek6MpVh1j3Yzk803ZroF-DWjB3dMQ6TzBGn-FiPnL38c_U-I9JowlwEAXaew3roQx0tHTU4dlO2AMji5-YhwH-h0L2HEIBTO1W3pXEoSYn-z-zgAF3pJXHoaM7_bzmPy4OF-efauubuaXZ6dXFQjVlaprmPZacYFCigaUYr1TVtlaa2X7RqPQSrQKRe3RtrJRgjvVidrZTna8l-KYfNrtdWnMOaE36xQeIG0NZ-apOPNc3GQ_7Ox6Yx-wP8h9UxP4uAeQHQw-QXQhH5yQDZMtm1y1cyEX_P2cQ7o3rRJKmuXizvBu2dzOl9fm9rAXXDarcZPiVMl_HvwHsoiRMA</recordid><startdate>20020313</startdate><enddate>20020313</enddate><creator>Molyneux, Russell J</creator><creator>Mahoney, Noreen</creator><creator>Bayman, Paul</creator><creator>Wong, Rosalind Y</creator><creator>Meyer, Kenneth</creator><creator>Irelan, Nancy</creator><general>American Chemical Society</general><scope>BSCLL</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></search><sort><creationdate>20020313</creationdate><title>Eutypa Dieback in Grapevines: Differential Production of Acetylenic Phenol Metabolites by Strains of Eutypa lata</title><author>Molyneux, Russell J ; Mahoney, Noreen ; Bayman, Paul ; Wong, Rosalind Y ; Meyer, Kenneth ; Irelan, Nancy</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a379t-9408f8713e3534a770dc7b7b2887bd48e387367e32feb654731c7932cb9591d53</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2002</creationdate><topic>Alkynes</topic><topic>Ascomycota - metabolism</topic><topic>Benzaldehydes - analysis</topic><topic>Benzaldehydes - metabolism</topic><topic>Biological and medical sciences</topic><topic>Chromatography, High Pressure Liquid - methods</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Fungal plant pathogens</topic><topic>Gas Chromatography-Mass Spectrometry - methods</topic><topic>Hydrogen-Ion Concentration</topic><topic>Mycotoxins - metabolism</topic><topic>Pathology, epidemiology, host-fungus relationships. Damages, economic importance</topic><topic>Phenols - metabolism</topic><topic>Phytopathology. Animal pests. Plant and forest protection</topic><topic>Plant Diseases - microbiology</topic><topic>Vitis - microbiology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Molyneux, Russell J</creatorcontrib><creatorcontrib>Mahoney, Noreen</creatorcontrib><creatorcontrib>Bayman, Paul</creatorcontrib><creatorcontrib>Wong, Rosalind Y</creatorcontrib><creatorcontrib>Meyer, Kenneth</creatorcontrib><creatorcontrib>Irelan, Nancy</creatorcontrib><collection>Istex</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><jtitle>Journal of agricultural and food chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Molyneux, Russell J</au><au>Mahoney, Noreen</au><au>Bayman, Paul</au><au>Wong, Rosalind Y</au><au>Meyer, Kenneth</au><au>Irelan, Nancy</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Eutypa Dieback in Grapevines: Differential Production of Acetylenic Phenol Metabolites by Strains of Eutypa lata</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>2002-03-13</date><risdate>2002</risdate><volume>50</volume><issue>6</issue><spage>1393</spage><epage>1399</epage><pages>1393-1399</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><coden>JAFCAU</coden><abstract>The production of acetylenic phenol metabolites in vitro by three strains of the ascomycete Eutypa lata, the causative agent of dying-arm disease in grapevines, has been investigated. Metabolite composition and yields differed significantly between strains and with growth medium but usually reached a maximum after 24−30 days of fungal growth. A general method for the analysis and identification of metabolites by gas chromatography/mass spectrometry of their trimethylsilyl ether derivatives was developed and individual compounds were quantitated by analytical high-performance liquid chromatography (HPLC) and separated by preparative HPLC. The phenolic aldehyde, eutypine (1), reported to be the grape phytotoxin, occurred in only one of the strains examined whereas the primary metabolite was the corresponding alcohol, eutypinol (2), the presumptive detoxification product. A novel metabolite was isolated as a major constituent, together with a minor component, and their structures were established by spectroscopic methods as a methoxyquinol, named eulatinol (4), and a chromene analog (9) of 2, respectively. The evidence suggests that 1 is not solely responsible for phytotoxicity in grapevines but that dying-arm disease may result from a suite of compounds elaborated by the fungus, with the composition dependent on fungal strain and nutritional source. Keywords: Grapes; Vitis vinifera; Eutypa lata; dieback; eutyposis; vine decline; dying-arm disease; chromene</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>11879009</pmid><doi>10.1021/jf011215a</doi><tpages>7</tpages></addata></record> |
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| ispartof | Journal of agricultural and food chemistry, 2002-03, Vol.50 (6), p.1393-1399 |
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| subjects | Alkynes Ascomycota - metabolism Benzaldehydes - analysis Benzaldehydes - metabolism Biological and medical sciences Chromatography, High Pressure Liquid - methods Fundamental and applied biological sciences. Psychology Fungal plant pathogens Gas Chromatography-Mass Spectrometry - methods Hydrogen-Ion Concentration Mycotoxins - metabolism Pathology, epidemiology, host-fungus relationships. Damages, economic importance Phenols - metabolism Phytopathology. Animal pests. Plant and forest protection Plant Diseases - microbiology Vitis - microbiology |
| title | Eutypa Dieback in Grapevines: Differential Production of Acetylenic Phenol Metabolites by Strains of Eutypa lata |
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