Methyl jasmonate elicits the production of methyl (E)-2-hexenoate from (Z)-2-hexenol via (Z)-2-hexenal in Achyranthes bidentata plant
•A. bidentata plant produced methyl (E)-2-hexenoate (1) under MeJA elicitation.•Methyl (E)-2-hexenoate (1) production was enhanced by (Z)-2-hexenol application.•Methyl (E)-2-hexenoate (1) might be biosynthesized from (Z)-2-hexenol via (Z)-2-hexenal. The medicinal herbal plant Achyranthes bidentata (...
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| Veröffentlicht in: | FEBS letters 2015-01, Vol.589 (3), p.390-395 |
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| creator | Tamogami, Shigeru Noge, Koji Agrawal, Ganesh K. Rakwal, Randeep |
| description | •A. bidentata plant produced methyl (E)-2-hexenoate (1) under MeJA elicitation.•Methyl (E)-2-hexenoate (1) production was enhanced by (Z)-2-hexenol application.•Methyl (E)-2-hexenoate (1) might be biosynthesized from (Z)-2-hexenol via (Z)-2-hexenal.
The medicinal herbal plant Achyranthes bidentata (A. bidentata) produces the sweet-odor ester – methyl (E)-2-hexenoate (1) as the major volatile in response to methyl jasmonate (MeJA). Here, we investigated the biosynthetic pathway of methyl (E)-2-hexenoate (1). The common plant precursor (Z)-3-hexenal was only slightly metabolized into methyl (E)-2-hexenoate (1), and its application scarcely enhanced the production of this ester. By contrast, a structurally related alcohol, (Z)-2-hexenol, as well as a deuteride derivative thereof could be efficiently metabolized into methyl (E)-2-hexenoate (1). Thus, we hypothesize that A. bidentata possess a specific pathway for the production of methyl (E)-2-hexenoate (1) from (Z)-2-hexenol in response to MeJA. |
| doi_str_mv | 10.1016/j.febslet.2014.12.025 |
| format | Article |
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The medicinal herbal plant Achyranthes bidentata (A. bidentata) produces the sweet-odor ester – methyl (E)-2-hexenoate (1) as the major volatile in response to methyl jasmonate (MeJA). Here, we investigated the biosynthetic pathway of methyl (E)-2-hexenoate (1). The common plant precursor (Z)-3-hexenal was only slightly metabolized into methyl (E)-2-hexenoate (1), and its application scarcely enhanced the production of this ester. By contrast, a structurally related alcohol, (Z)-2-hexenol, as well as a deuteride derivative thereof could be efficiently metabolized into methyl (E)-2-hexenoate (1). Thus, we hypothesize that A. bidentata possess a specific pathway for the production of methyl (E)-2-hexenoate (1) from (Z)-2-hexenol in response to MeJA.</description><identifier>ISSN: 0014-5793</identifier><identifier>EISSN: 1873-3468</identifier><identifier>DOI: 10.1016/j.febslet.2014.12.025</identifier><identifier>PMID: 25575415</identifier><language>eng</language><publisher>England: Elsevier B.V</publisher><subject>(Z)-2-Hexenal ; (Z)-2-Hexenol ; Acetates - chemistry ; Acetates - metabolism ; Achyranthes - chemistry ; Achyranthes - metabolism ; Aldehydes - chemical synthesis ; Aldehydes - chemistry ; Aldehydes - metabolism ; Cyclopentanes - chemistry ; Cyclopentanes - metabolism ; EIC ; Esters - chemistry ; Esters - metabolism ; extracted ion chromatogram ; Isoleucine - analogs & derivatives ; JA-Ile ; Jasmonic acid ; jasmonoyl isoleucine ; MeJA ; Methyl (E)-2-hexenoate ; Methyl jasmonate ; Oxylipins - chemistry ; Oxylipins - metabolism ; Plants, Medicinal - chemistry ; Plants, Medicinal - metabolism ; six-carbon</subject><ispartof>FEBS letters, 2015-01, Vol.589 (3), p.390-395</ispartof><rights>2015 Federation of European Biochemical Societies</rights><rights>FEBS Letters 589 (2015) 1873-3468 © 2015 Federation of European Biochemical Societies</rights><rights>Copyright © 2015 Federation of European Biochemical Societies. Published by Elsevier B.V. All rights reserved.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c6363-2b8903240f57a183ad43ca53341097bf329e361c79de3b95770f7635fe8f054c3</citedby><cites>FETCH-LOGICAL-c6363-2b8903240f57a183ad43ca53341097bf329e361c79de3b95770f7635fe8f054c3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1016%2Fj.febslet.2014.12.025$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.febslet.2014.12.025$$EHTML$$P50$$Gelsevier$$Hfree_for_read</linktohtml><link.rule.ids>314,780,784,1416,1432,3548,27923,27924,45573,45574,45994,46408,46832</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25575415$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Tamogami, Shigeru</creatorcontrib><creatorcontrib>Noge, Koji</creatorcontrib><creatorcontrib>Agrawal, Ganesh K.</creatorcontrib><creatorcontrib>Rakwal, Randeep</creatorcontrib><title>Methyl jasmonate elicits the production of methyl (E)-2-hexenoate from (Z)-2-hexenol via (Z)-2-hexenal in Achyranthes bidentata plant</title><title>FEBS letters</title><addtitle>FEBS Lett</addtitle><description>•A. bidentata plant produced methyl (E)-2-hexenoate (1) under MeJA elicitation.•Methyl (E)-2-hexenoate (1) production was enhanced by (Z)-2-hexenol application.•Methyl (E)-2-hexenoate (1) might be biosynthesized from (Z)-2-hexenol via (Z)-2-hexenal.
The medicinal herbal plant Achyranthes bidentata (A. bidentata) produces the sweet-odor ester – methyl (E)-2-hexenoate (1) as the major volatile in response to methyl jasmonate (MeJA). Here, we investigated the biosynthetic pathway of methyl (E)-2-hexenoate (1). The common plant precursor (Z)-3-hexenal was only slightly metabolized into methyl (E)-2-hexenoate (1), and its application scarcely enhanced the production of this ester. By contrast, a structurally related alcohol, (Z)-2-hexenol, as well as a deuteride derivative thereof could be efficiently metabolized into methyl (E)-2-hexenoate (1). Thus, we hypothesize that A. bidentata possess a specific pathway for the production of methyl (E)-2-hexenoate (1) from (Z)-2-hexenol in response to MeJA.</description><subject>(Z)-2-Hexenal</subject><subject>(Z)-2-Hexenol</subject><subject>Acetates - chemistry</subject><subject>Acetates - metabolism</subject><subject>Achyranthes - chemistry</subject><subject>Achyranthes - metabolism</subject><subject>Aldehydes - chemical synthesis</subject><subject>Aldehydes - chemistry</subject><subject>Aldehydes - metabolism</subject><subject>Cyclopentanes - chemistry</subject><subject>Cyclopentanes - metabolism</subject><subject>EIC</subject><subject>Esters - chemistry</subject><subject>Esters - metabolism</subject><subject>extracted ion chromatogram</subject><subject>Isoleucine - analogs & derivatives</subject><subject>JA-Ile</subject><subject>Jasmonic acid</subject><subject>jasmonoyl isoleucine</subject><subject>MeJA</subject><subject>Methyl (E)-2-hexenoate</subject><subject>Methyl jasmonate</subject><subject>Oxylipins - chemistry</subject><subject>Oxylipins - metabolism</subject><subject>Plants, Medicinal - chemistry</subject><subject>Plants, Medicinal - metabolism</subject><subject>six-carbon</subject><issn>0014-5793</issn><issn>1873-3468</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqNUc2O0zAYtBCILYVHAPlYDgn-ieP4hHZXXRZpEQfgwsVynM-qKycpsbvQB-C9cUj5ucHJ8nhmvvE3CD2npKSE1q_2pYM2BkglI7QqKSsJEw_QijaSF7yqm4doRfJLIaTiF-hJjHuS7w1Vj9EFE0KKiooV-v4O0u4U8N7EfhxMAgzBW58iTjvAh2nsjjb5ccCjw_1C3WxfFqzYwTcYxlngprHHm89_wIDvvfkbMQH7AV_a3WkyQ_aNuPUdDMkkgw8hQ0_RI2dChGfnc40-3Ww_Xt8Wd-_fvL2-vCtszWtesLZRhLOKOCENbbjpKm6N4LyiRMnWcaaA19RK1QFvlZCSOFlz4aBxRFSWr9Fm8c0f-3KEmHTvo4WQM8B4jJrWgnGlVLZcI7FQ7TTGOIHTh8n3ZjppSvTcgN7rcwN6bkBTpnMDWffiPOLY9tD9Vv1aeSbcLoSvPsDp_1z1zfaKfZjrnNukFSGK_Mz4erGCvLN7D5OO1sNgofMT2KS70f8j7Q_9a64S</recordid><startdate>20150130</startdate><enddate>20150130</enddate><creator>Tamogami, Shigeru</creator><creator>Noge, Koji</creator><creator>Agrawal, Ganesh K.</creator><creator>Rakwal, Randeep</creator><general>Elsevier B.V</general><scope>6I.</scope><scope>AAFTH</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>7X8</scope></search><sort><creationdate>20150130</creationdate><title>Methyl jasmonate elicits the production of methyl (E)-2-hexenoate from (Z)-2-hexenol via (Z)-2-hexenal in Achyranthes bidentata plant</title><author>Tamogami, Shigeru ; Noge, Koji ; Agrawal, Ganesh K. ; Rakwal, Randeep</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c6363-2b8903240f57a183ad43ca53341097bf329e361c79de3b95770f7635fe8f054c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>(Z)-2-Hexenal</topic><topic>(Z)-2-Hexenol</topic><topic>Acetates - chemistry</topic><topic>Acetates - metabolism</topic><topic>Achyranthes - chemistry</topic><topic>Achyranthes - metabolism</topic><topic>Aldehydes - chemical synthesis</topic><topic>Aldehydes - chemistry</topic><topic>Aldehydes - metabolism</topic><topic>Cyclopentanes - chemistry</topic><topic>Cyclopentanes - metabolism</topic><topic>EIC</topic><topic>Esters - chemistry</topic><topic>Esters - metabolism</topic><topic>extracted ion chromatogram</topic><topic>Isoleucine - analogs & derivatives</topic><topic>JA-Ile</topic><topic>Jasmonic acid</topic><topic>jasmonoyl isoleucine</topic><topic>MeJA</topic><topic>Methyl (E)-2-hexenoate</topic><topic>Methyl jasmonate</topic><topic>Oxylipins - chemistry</topic><topic>Oxylipins - metabolism</topic><topic>Plants, Medicinal - chemistry</topic><topic>Plants, Medicinal - metabolism</topic><topic>six-carbon</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tamogami, Shigeru</creatorcontrib><creatorcontrib>Noge, Koji</creatorcontrib><creatorcontrib>Agrawal, Ganesh K.</creatorcontrib><creatorcontrib>Rakwal, Randeep</creatorcontrib><collection>ScienceDirect Open Access Titles</collection><collection>Elsevier:ScienceDirect:Open Access</collection><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>FEBS letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tamogami, Shigeru</au><au>Noge, Koji</au><au>Agrawal, Ganesh K.</au><au>Rakwal, Randeep</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Methyl jasmonate elicits the production of methyl (E)-2-hexenoate from (Z)-2-hexenol via (Z)-2-hexenal in Achyranthes bidentata plant</atitle><jtitle>FEBS letters</jtitle><addtitle>FEBS Lett</addtitle><date>2015-01-30</date><risdate>2015</risdate><volume>589</volume><issue>3</issue><spage>390</spage><epage>395</epage><pages>390-395</pages><issn>0014-5793</issn><eissn>1873-3468</eissn><abstract>•A. bidentata plant produced methyl (E)-2-hexenoate (1) under MeJA elicitation.•Methyl (E)-2-hexenoate (1) production was enhanced by (Z)-2-hexenol application.•Methyl (E)-2-hexenoate (1) might be biosynthesized from (Z)-2-hexenol via (Z)-2-hexenal.
The medicinal herbal plant Achyranthes bidentata (A. bidentata) produces the sweet-odor ester – methyl (E)-2-hexenoate (1) as the major volatile in response to methyl jasmonate (MeJA). Here, we investigated the biosynthetic pathway of methyl (E)-2-hexenoate (1). The common plant precursor (Z)-3-hexenal was only slightly metabolized into methyl (E)-2-hexenoate (1), and its application scarcely enhanced the production of this ester. By contrast, a structurally related alcohol, (Z)-2-hexenol, as well as a deuteride derivative thereof could be efficiently metabolized into methyl (E)-2-hexenoate (1). Thus, we hypothesize that A. bidentata possess a specific pathway for the production of methyl (E)-2-hexenoate (1) from (Z)-2-hexenol in response to MeJA.</abstract><cop>England</cop><pub>Elsevier B.V</pub><pmid>25575415</pmid><doi>10.1016/j.febslet.2014.12.025</doi><tpages>6</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | FEBS letters, 2015-01, Vol.589 (3), p.390-395 |
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| source | MEDLINE; Elsevier ScienceDirect Journals Complete; Wiley Free Archive; Wiley Blackwell Single Titles; Alma/SFX Local Collection; EZB Electronic Journals Library |
| subjects | (Z)-2-Hexenal (Z)-2-Hexenol Acetates - chemistry Acetates - metabolism Achyranthes - chemistry Achyranthes - metabolism Aldehydes - chemical synthesis Aldehydes - chemistry Aldehydes - metabolism Cyclopentanes - chemistry Cyclopentanes - metabolism EIC Esters - chemistry Esters - metabolism extracted ion chromatogram Isoleucine - analogs & derivatives JA-Ile Jasmonic acid jasmonoyl isoleucine MeJA Methyl (E)-2-hexenoate Methyl jasmonate Oxylipins - chemistry Oxylipins - metabolism Plants, Medicinal - chemistry Plants, Medicinal - metabolism six-carbon |
| title | Methyl jasmonate elicits the production of methyl (E)-2-hexenoate from (Z)-2-hexenol via (Z)-2-hexenal in Achyranthes bidentata plant |
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