Induced accumulation of tyramine, serotonin, and related amines in response to Bipolaris sorokiniana infection in barley
The inducible metabolites were analyzed in barley leaves inoculated with Bipolaris sorokiniana, the causal agent of spot blotch of barley. HPLC analysis revealed that B. sorokiniana-infected leaves accumulated 4 hydrophilic compounds. They were purified by ODS column chromatography and preparative H...
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| Veröffentlicht in: | Bioscience, biotechnology, and biochemistry biotechnology, and biochemistry, 2017-06, Vol.81 (6), p.1090-1098 |
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| creator | Ishihara, Atsushi Kumeda, Rie Hayashi, Noriko Yagi, Yukari Sakaguchi, Nanase Kokubo, Yu Ube, Naoki Tebayashi, Shin-ichi Ueno, Kotomi |
| description | The inducible metabolites were analyzed in barley leaves inoculated with Bipolaris sorokiniana, the causal agent of spot blotch of barley. HPLC analysis revealed that B. sorokiniana-infected leaves accumulated 4 hydrophilic compounds. They were purified by ODS column chromatography and preparative HPLC. Spectroscopic analyses revealed that they were tyramine (1), 3-(2-aminoethyl)-3-hydroxyindolin-2-one (2), serotonin (3), and 5,5′-dihydroxy-2,4′-bitryptamine (4). Among these, 2 and 4 have not been reported as natural products. They showed antifungal activity in an assay of inhibition of B. sorokiniana conidia germination, suggesting that they play a role in the chemical defense of barley as phytoalexins. The accumulation of 1-4 was examined also in the leaves of rice and foxtail millet. Rice leaves accumulated 2, 3, and 4, whereas foxtail millet leaves accumulated 3 and 4 in response to pathogen attack, suggesting the generality of accumulation of 3 and 4 in the Poaceae species. |
| doi_str_mv | 10.1080/09168451.2017.1290520 |
| format | Article |
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HPLC analysis revealed that B. sorokiniana-infected leaves accumulated 4 hydrophilic compounds. They were purified by ODS column chromatography and preparative HPLC. Spectroscopic analyses revealed that they were tyramine (1), 3-(2-aminoethyl)-3-hydroxyindolin-2-one (2), serotonin (3), and 5,5′-dihydroxy-2,4′-bitryptamine (4). Among these, 2 and 4 have not been reported as natural products. They showed antifungal activity in an assay of inhibition of B. sorokiniana conidia germination, suggesting that they play a role in the chemical defense of barley as phytoalexins. The accumulation of 1-4 was examined also in the leaves of rice and foxtail millet. Rice leaves accumulated 2, 3, and 4, whereas foxtail millet leaves accumulated 3 and 4 in response to pathogen attack, suggesting the generality of accumulation of 3 and 4 in the Poaceae species.</description><identifier>ISSN: 0916-8451</identifier><identifier>EISSN: 1347-6947</identifier><identifier>DOI: 10.1080/09168451.2017.1290520</identifier><identifier>PMID: 28485206</identifier><language>eng</language><publisher>England: Taylor & Francis</publisher><subject>Antifungal Agents - immunology ; Antifungal Agents - metabolism ; Antifungal Agents - pharmacology ; barley ; Bipolaris sorokiniana ; Chromatography, High Pressure Liquid ; dimer ; Hordeum - immunology ; Hordeum - metabolism ; Hordeum - microbiology ; Hydrophobic and Hydrophilic Interactions ; Indoles - immunology ; Indoles - metabolism ; Indoles - pharmacology ; Oryza - immunology ; Oryza - metabolism ; Oryza - microbiology ; Plant Diseases - immunology ; Plant Diseases - microbiology ; Plant Immunity ; Plant Leaves - immunology ; Plant Leaves - metabolism ; Plant Leaves - microbiology ; Poaceae ; Saccharomycetales - drug effects ; Saccharomycetales - pathogenicity ; Saccharomycetales - physiology ; serotonin ; Serotonin - biosynthesis ; Serotonin - immunology ; Serotonin - pharmacology ; Sesquiterpenes - immunology ; Sesquiterpenes - metabolism ; Sesquiterpenes - pharmacology ; Setaria Plant - immunology ; Setaria Plant - metabolism ; Setaria Plant - microbiology ; Species Specificity ; Spores, Fungal - drug effects ; Spores, Fungal - pathogenicity ; Spores, Fungal - physiology ; Tryptamines - biosynthesis ; Tryptamines - immunology ; Tryptamines - pharmacology ; Tyramine - biosynthesis ; Tyramine - immunology ; Tyramine - pharmacology</subject><ispartof>Bioscience, biotechnology, and biochemistry, 2017-06, Vol.81 (6), p.1090-1098</ispartof><rights>2017 Japan Society for Bioscience, Biotechnology, and Agrochemistry 2017</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c520t-55aedc5bdc969c94953e1b235154abb618ceb6f10b608be22ab32ebaf55d3ed63</citedby><cites>FETCH-LOGICAL-c520t-55aedc5bdc969c94953e1b235154abb618ceb6f10b608be22ab32ebaf55d3ed63</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,777,781,27905,27906</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/28485206$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ishihara, Atsushi</creatorcontrib><creatorcontrib>Kumeda, Rie</creatorcontrib><creatorcontrib>Hayashi, Noriko</creatorcontrib><creatorcontrib>Yagi, Yukari</creatorcontrib><creatorcontrib>Sakaguchi, Nanase</creatorcontrib><creatorcontrib>Kokubo, Yu</creatorcontrib><creatorcontrib>Ube, Naoki</creatorcontrib><creatorcontrib>Tebayashi, Shin-ichi</creatorcontrib><creatorcontrib>Ueno, Kotomi</creatorcontrib><title>Induced accumulation of tyramine, serotonin, and related amines in response to Bipolaris sorokiniana infection in barley</title><title>Bioscience, biotechnology, and biochemistry</title><addtitle>Biosci Biotechnol Biochem</addtitle><description>The inducible metabolites were analyzed in barley leaves inoculated with Bipolaris sorokiniana, the causal agent of spot blotch of barley. HPLC analysis revealed that B. sorokiniana-infected leaves accumulated 4 hydrophilic compounds. They were purified by ODS column chromatography and preparative HPLC. Spectroscopic analyses revealed that they were tyramine (1), 3-(2-aminoethyl)-3-hydroxyindolin-2-one (2), serotonin (3), and 5,5′-dihydroxy-2,4′-bitryptamine (4). Among these, 2 and 4 have not been reported as natural products. They showed antifungal activity in an assay of inhibition of B. sorokiniana conidia germination, suggesting that they play a role in the chemical defense of barley as phytoalexins. The accumulation of 1-4 was examined also in the leaves of rice and foxtail millet. Rice leaves accumulated 2, 3, and 4, whereas foxtail millet leaves accumulated 3 and 4 in response to pathogen attack, suggesting the generality of accumulation of 3 and 4 in the Poaceae species.</description><subject>Antifungal Agents - immunology</subject><subject>Antifungal Agents - metabolism</subject><subject>Antifungal Agents - pharmacology</subject><subject>barley</subject><subject>Bipolaris sorokiniana</subject><subject>Chromatography, High Pressure Liquid</subject><subject>dimer</subject><subject>Hordeum - immunology</subject><subject>Hordeum - metabolism</subject><subject>Hordeum - microbiology</subject><subject>Hydrophobic and Hydrophilic Interactions</subject><subject>Indoles - immunology</subject><subject>Indoles - metabolism</subject><subject>Indoles - pharmacology</subject><subject>Oryza - immunology</subject><subject>Oryza - metabolism</subject><subject>Oryza - microbiology</subject><subject>Plant Diseases - immunology</subject><subject>Plant Diseases - microbiology</subject><subject>Plant Immunity</subject><subject>Plant Leaves - immunology</subject><subject>Plant Leaves - metabolism</subject><subject>Plant Leaves - microbiology</subject><subject>Poaceae</subject><subject>Saccharomycetales - drug effects</subject><subject>Saccharomycetales - pathogenicity</subject><subject>Saccharomycetales - physiology</subject><subject>serotonin</subject><subject>Serotonin - biosynthesis</subject><subject>Serotonin - immunology</subject><subject>Serotonin - pharmacology</subject><subject>Sesquiterpenes - immunology</subject><subject>Sesquiterpenes - metabolism</subject><subject>Sesquiterpenes - pharmacology</subject><subject>Setaria Plant - immunology</subject><subject>Setaria Plant - metabolism</subject><subject>Setaria Plant - microbiology</subject><subject>Species Specificity</subject><subject>Spores, Fungal - drug effects</subject><subject>Spores, Fungal - pathogenicity</subject><subject>Spores, Fungal - physiology</subject><subject>Tryptamines - biosynthesis</subject><subject>Tryptamines - immunology</subject><subject>Tryptamines - pharmacology</subject><subject>Tyramine - biosynthesis</subject><subject>Tyramine - immunology</subject><subject>Tyramine - pharmacology</subject><issn>0916-8451</issn><issn>1347-6947</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqNkMFu1DAQhi0EapfSRwD5yKFZbCd24hu0KqVSJS5wtsbORDIkdrATwb59HXbLEfVkafz9_4w-Qt5ytuesYx-Y5qprJN8Lxts9F5pJwV6QHa-btlK6aV-S3cZUG3ROXuf8g7EykPyMnIuu6QquduTPfehXhz0F59ZpHWHxMdA40OWQYPIBr2jGFJcYfLiiEHqasEBbYPvN1IcyyXMMGekS6bWf4wjJZ5pjij998BCgQAO6v80Ft5BGPLwhrwYYM16e3gvy_fPtt5sv1cPXu_ubTw-VKwculZSAvZO2d1pppxsta-RW1JLLBqxVvHNo1cCZVayzKATYWqCFQcq-xl7VF-T9sXdO8deKeTGTzw7HEQLGNRveadVpUbdtQeURdSnmnHAwc_ITpIPhzGzSzZN0s0k3J-kl9-60YrUT9v9ST5YLwI5AXOdnd348Roq6mCb4HdPYmwUOY0xDguB8NvX_Kx4BaY-hIw</recordid><startdate>20170603</startdate><enddate>20170603</enddate><creator>Ishihara, Atsushi</creator><creator>Kumeda, Rie</creator><creator>Hayashi, Noriko</creator><creator>Yagi, Yukari</creator><creator>Sakaguchi, Nanase</creator><creator>Kokubo, Yu</creator><creator>Ube, Naoki</creator><creator>Tebayashi, Shin-ichi</creator><creator>Ueno, Kotomi</creator><general>Taylor & Francis</general><general>Oxford University Press</general><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>20170603</creationdate><title>Induced accumulation of tyramine, serotonin, and related amines in response to Bipolaris sorokiniana infection in barley</title><author>Ishihara, Atsushi ; Kumeda, Rie ; Hayashi, Noriko ; Yagi, Yukari ; Sakaguchi, Nanase ; Kokubo, Yu ; Ube, Naoki ; Tebayashi, Shin-ichi ; Ueno, Kotomi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c520t-55aedc5bdc969c94953e1b235154abb618ceb6f10b608be22ab32ebaf55d3ed63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Antifungal Agents - immunology</topic><topic>Antifungal Agents - metabolism</topic><topic>Antifungal Agents - pharmacology</topic><topic>barley</topic><topic>Bipolaris sorokiniana</topic><topic>Chromatography, High Pressure Liquid</topic><topic>dimer</topic><topic>Hordeum - immunology</topic><topic>Hordeum - metabolism</topic><topic>Hordeum - microbiology</topic><topic>Hydrophobic and Hydrophilic Interactions</topic><topic>Indoles - immunology</topic><topic>Indoles - metabolism</topic><topic>Indoles - pharmacology</topic><topic>Oryza - immunology</topic><topic>Oryza - metabolism</topic><topic>Oryza - microbiology</topic><topic>Plant Diseases - immunology</topic><topic>Plant Diseases - microbiology</topic><topic>Plant Immunity</topic><topic>Plant Leaves - immunology</topic><topic>Plant Leaves - metabolism</topic><topic>Plant Leaves - microbiology</topic><topic>Poaceae</topic><topic>Saccharomycetales - drug effects</topic><topic>Saccharomycetales - pathogenicity</topic><topic>Saccharomycetales - physiology</topic><topic>serotonin</topic><topic>Serotonin - biosynthesis</topic><topic>Serotonin - immunology</topic><topic>Serotonin - pharmacology</topic><topic>Sesquiterpenes - immunology</topic><topic>Sesquiterpenes - metabolism</topic><topic>Sesquiterpenes - pharmacology</topic><topic>Setaria Plant - immunology</topic><topic>Setaria Plant - metabolism</topic><topic>Setaria Plant - microbiology</topic><topic>Species Specificity</topic><topic>Spores, Fungal - drug effects</topic><topic>Spores, Fungal - pathogenicity</topic><topic>Spores, Fungal - physiology</topic><topic>Tryptamines - biosynthesis</topic><topic>Tryptamines - immunology</topic><topic>Tryptamines - pharmacology</topic><topic>Tyramine - biosynthesis</topic><topic>Tyramine - immunology</topic><topic>Tyramine - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ishihara, Atsushi</creatorcontrib><creatorcontrib>Kumeda, Rie</creatorcontrib><creatorcontrib>Hayashi, Noriko</creatorcontrib><creatorcontrib>Yagi, Yukari</creatorcontrib><creatorcontrib>Sakaguchi, Nanase</creatorcontrib><creatorcontrib>Kokubo, Yu</creatorcontrib><creatorcontrib>Ube, Naoki</creatorcontrib><creatorcontrib>Tebayashi, Shin-ichi</creatorcontrib><creatorcontrib>Ueno, Kotomi</creatorcontrib><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>Bioscience, biotechnology, and biochemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ishihara, Atsushi</au><au>Kumeda, Rie</au><au>Hayashi, Noriko</au><au>Yagi, Yukari</au><au>Sakaguchi, Nanase</au><au>Kokubo, Yu</au><au>Ube, Naoki</au><au>Tebayashi, Shin-ichi</au><au>Ueno, Kotomi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Induced accumulation of tyramine, serotonin, and related amines in response to Bipolaris sorokiniana infection in barley</atitle><jtitle>Bioscience, biotechnology, and biochemistry</jtitle><addtitle>Biosci Biotechnol Biochem</addtitle><date>2017-06-03</date><risdate>2017</risdate><volume>81</volume><issue>6</issue><spage>1090</spage><epage>1098</epage><pages>1090-1098</pages><issn>0916-8451</issn><eissn>1347-6947</eissn><abstract>The inducible metabolites were analyzed in barley leaves inoculated with Bipolaris sorokiniana, the causal agent of spot blotch of barley. HPLC analysis revealed that B. sorokiniana-infected leaves accumulated 4 hydrophilic compounds. They were purified by ODS column chromatography and preparative HPLC. Spectroscopic analyses revealed that they were tyramine (1), 3-(2-aminoethyl)-3-hydroxyindolin-2-one (2), serotonin (3), and 5,5′-dihydroxy-2,4′-bitryptamine (4). Among these, 2 and 4 have not been reported as natural products. They showed antifungal activity in an assay of inhibition of B. sorokiniana conidia germination, suggesting that they play a role in the chemical defense of barley as phytoalexins. The accumulation of 1-4 was examined also in the leaves of rice and foxtail millet. Rice leaves accumulated 2, 3, and 4, whereas foxtail millet leaves accumulated 3 and 4 in response to pathogen attack, suggesting the generality of accumulation of 3 and 4 in the Poaceae species.</abstract><cop>England</cop><pub>Taylor & Francis</pub><pmid>28485206</pmid><doi>10.1080/09168451.2017.1290520</doi><tpages>9</tpages><oa>free_for_read</oa></addata></record> |
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| source | MEDLINE; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; Oxford University Press Journals All Titles (1996-Current); Freely Accessible Japanese Titles |
| subjects | Antifungal Agents - immunology Antifungal Agents - metabolism Antifungal Agents - pharmacology barley Bipolaris sorokiniana Chromatography, High Pressure Liquid dimer Hordeum - immunology Hordeum - metabolism Hordeum - microbiology Hydrophobic and Hydrophilic Interactions Indoles - immunology Indoles - metabolism Indoles - pharmacology Oryza - immunology Oryza - metabolism Oryza - microbiology Plant Diseases - immunology Plant Diseases - microbiology Plant Immunity Plant Leaves - immunology Plant Leaves - metabolism Plant Leaves - microbiology Poaceae Saccharomycetales - drug effects Saccharomycetales - pathogenicity Saccharomycetales - physiology serotonin Serotonin - biosynthesis Serotonin - immunology Serotonin - pharmacology Sesquiterpenes - immunology Sesquiterpenes - metabolism Sesquiterpenes - pharmacology Setaria Plant - immunology Setaria Plant - metabolism Setaria Plant - microbiology Species Specificity Spores, Fungal - drug effects Spores, Fungal - pathogenicity Spores, Fungal - physiology Tryptamines - biosynthesis Tryptamines - immunology Tryptamines - pharmacology Tyramine - biosynthesis Tyramine - immunology Tyramine - pharmacology |
| title | Induced accumulation of tyramine, serotonin, and related amines in response to Bipolaris sorokiniana infection in barley |
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