Tryptophan derivatives regulate the seed germination and radicle growth of a root parasitic plant, Orobanche minor
[Display omitted] Root parasitic plant germination is induced by the host-derived chemical, strigolactone (SL). We found that a major microbial culture broth component, tryptone, inhibits the SL-inducible germination of a root parasitic plant, Orobanche minor. l-tryptophan (l-Trp) was isolated as th...
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Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2021-07, Vol.43, p.128085-128085, Article 128085 |
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creator | Kuruma, Michio Suzuki, Taiki Seto, Yoshiya |
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Root parasitic plant germination is induced by the host-derived chemical, strigolactone (SL). We found that a major microbial culture broth component, tryptone, inhibits the SL-inducible germination of a root parasitic plant, Orobanche minor. l-tryptophan (l-Trp) was isolated as the active compound from tryptone. We further found that l-Trp related compounds (1b-11), such as a major plant hormone auxin (8, indole-3-acetic acid; IAA), also inhibit the germination and post-radicle growth of O. minor. We designed a hybrid chemical (13), in which IAA is attached to a part of SL, and found that this synthetic analog induced the germination of O. minor, and also inhibited post-radicle growth. Moreover, contrary to our expectations, we found that N-acetyl Trp (9) showed germination stimulating activity, and introduction of a substitution at C-5 position increased its activity (12a-12f). Our data, in particular, the discovery of a structurally hybrid compound that has two activities that induce spontaneous germination and inhibit subsequent radical growth, would provide new types of germination regulators for root parasitic plants. |
doi_str_mv | 10.1016/j.bmcl.2021.128085 |
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Root parasitic plant germination is induced by the host-derived chemical, strigolactone (SL). We found that a major microbial culture broth component, tryptone, inhibits the SL-inducible germination of a root parasitic plant, Orobanche minor. l-tryptophan (l-Trp) was isolated as the active compound from tryptone. We further found that l-Trp related compounds (1b-11), such as a major plant hormone auxin (8, indole-3-acetic acid; IAA), also inhibit the germination and post-radicle growth of O. minor. We designed a hybrid chemical (13), in which IAA is attached to a part of SL, and found that this synthetic analog induced the germination of O. minor, and also inhibited post-radicle growth. Moreover, contrary to our expectations, we found that N-acetyl Trp (9) showed germination stimulating activity, and introduction of a substitution at C-5 position increased its activity (12a-12f). Our data, in particular, the discovery of a structurally hybrid compound that has two activities that induce spontaneous germination and inhibit subsequent radical growth, would provide new types of germination regulators for root parasitic plants.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2021.128085</identifier><identifier>PMID: 33964445</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>IAA ; N-acetyl tryptophan ; Radicle growth ; Root parasitic plant ; Strigolactone</subject><ispartof>Bioorganic & medicinal chemistry letters, 2021-07, Vol.43, p.128085-128085, Article 128085</ispartof><rights>2021 Elsevier Ltd</rights><rights>Copyright © 2021 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c400t-b1d8b6a591c6b3d5ec8407fee50d0b7149d3c4ff54a6ce95bdc554da7b58acf03</citedby><cites>FETCH-LOGICAL-c400t-b1d8b6a591c6b3d5ec8407fee50d0b7149d3c4ff54a6ce95bdc554da7b58acf03</cites><orcidid>0000-0003-1593-5717 ; 0000-0002-6810-3845</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0960894X21003115$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/33964445$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kuruma, Michio</creatorcontrib><creatorcontrib>Suzuki, Taiki</creatorcontrib><creatorcontrib>Seto, Yoshiya</creatorcontrib><title>Tryptophan derivatives regulate the seed germination and radicle growth of a root parasitic plant, Orobanche minor</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>[Display omitted]
Root parasitic plant germination is induced by the host-derived chemical, strigolactone (SL). We found that a major microbial culture broth component, tryptone, inhibits the SL-inducible germination of a root parasitic plant, Orobanche minor. l-tryptophan (l-Trp) was isolated as the active compound from tryptone. We further found that l-Trp related compounds (1b-11), such as a major plant hormone auxin (8, indole-3-acetic acid; IAA), also inhibit the germination and post-radicle growth of O. minor. We designed a hybrid chemical (13), in which IAA is attached to a part of SL, and found that this synthetic analog induced the germination of O. minor, and also inhibited post-radicle growth. Moreover, contrary to our expectations, we found that N-acetyl Trp (9) showed germination stimulating activity, and introduction of a substitution at C-5 position increased its activity (12a-12f). Our data, in particular, the discovery of a structurally hybrid compound that has two activities that induce spontaneous germination and inhibit subsequent radical growth, would provide new types of germination regulators for root parasitic plants.</description><subject>IAA</subject><subject>N-acetyl tryptophan</subject><subject>Radicle growth</subject><subject>Root parasitic plant</subject><subject>Strigolactone</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNp9kD1v2zAQhomiQeMm_QMdCo4dIoeUjrIEZAmM9AMIkCUFshH8ONk0JFE90g7y7yvDScZON9z7Prh7GPsqxVIKWV_vlnZw_bIUpVzKshGN-sAWEmooKhDqI1uIthZF08LTOfuc0k4ICQLgEzuvqrYGALVg9EgvU47T1ozcI4WDyeGAiRNu9r3JyPMWeUL0fIM0hHFex5Gb0XMyPrge-Ybic97y2HHDKcbMJ0MmhRwcn3oz5iv-QNGa0c2gGRDpkp11pk_45XVesD8_7h7Xv4r7h5-_17f3hQMhcmGlb2xtVCtdbSuv0DUgVh2iEl7YlYTWVw66ToGpHbbKeqcUeLOyqjGuE9UF-37iThT_7jFlPYTksJ-PwrhPulQlNE0lVTtHy1PUUUyJsNMThcHQi5ZCH13rnT661kfX-uR6Ln175e_tgP698iZ3DtycAjh_eQhIOrmAo0MfCF3WPob_8f8B20iSrQ</recordid><startdate>20210701</startdate><enddate>20210701</enddate><creator>Kuruma, Michio</creator><creator>Suzuki, Taiki</creator><creator>Seto, Yoshiya</creator><general>Elsevier Ltd</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-1593-5717</orcidid><orcidid>https://orcid.org/0000-0002-6810-3845</orcidid></search><sort><creationdate>20210701</creationdate><title>Tryptophan derivatives regulate the seed germination and radicle growth of a root parasitic plant, Orobanche minor</title><author>Kuruma, Michio ; Suzuki, Taiki ; Seto, Yoshiya</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c400t-b1d8b6a591c6b3d5ec8407fee50d0b7149d3c4ff54a6ce95bdc554da7b58acf03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>IAA</topic><topic>N-acetyl tryptophan</topic><topic>Radicle growth</topic><topic>Root parasitic plant</topic><topic>Strigolactone</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kuruma, Michio</creatorcontrib><creatorcontrib>Suzuki, Taiki</creatorcontrib><creatorcontrib>Seto, Yoshiya</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kuruma, Michio</au><au>Suzuki, Taiki</au><au>Seto, Yoshiya</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Tryptophan derivatives regulate the seed germination and radicle growth of a root parasitic plant, Orobanche minor</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2021-07-01</date><risdate>2021</risdate><volume>43</volume><spage>128085</spage><epage>128085</epage><pages>128085-128085</pages><artnum>128085</artnum><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>[Display omitted]
Root parasitic plant germination is induced by the host-derived chemical, strigolactone (SL). We found that a major microbial culture broth component, tryptone, inhibits the SL-inducible germination of a root parasitic plant, Orobanche minor. l-tryptophan (l-Trp) was isolated as the active compound from tryptone. We further found that l-Trp related compounds (1b-11), such as a major plant hormone auxin (8, indole-3-acetic acid; IAA), also inhibit the germination and post-radicle growth of O. minor. We designed a hybrid chemical (13), in which IAA is attached to a part of SL, and found that this synthetic analog induced the germination of O. minor, and also inhibited post-radicle growth. Moreover, contrary to our expectations, we found that N-acetyl Trp (9) showed germination stimulating activity, and introduction of a substitution at C-5 position increased its activity (12a-12f). Our data, in particular, the discovery of a structurally hybrid compound that has two activities that induce spontaneous germination and inhibit subsequent radical growth, would provide new types of germination regulators for root parasitic plants.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>33964445</pmid><doi>10.1016/j.bmcl.2021.128085</doi><tpages>1</tpages><orcidid>https://orcid.org/0000-0003-1593-5717</orcidid><orcidid>https://orcid.org/0000-0002-6810-3845</orcidid><oa>free_for_read</oa></addata></record> |
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subjects | IAA N-acetyl tryptophan Radicle growth Root parasitic plant Strigolactone |
title | Tryptophan derivatives regulate the seed germination and radicle growth of a root parasitic plant, Orobanche minor |
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