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Plant-growth inhibitory activity of heliannuol derivatives
Chromane and tetrahydro-oxepin derivatives related to heliannuols were submitted to assessment of plant-growth inhibitory activity. In addition to (+)-, (−)- and (±)-heliannuol E, growth-inhibitory activities of five synthetic chromans and four tetrahydrobenzo[b]oxepins were examined against oat and...
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Published in: | Phytochemistry (Oxford) 2004-05, Vol.65 (10), p.1405-1411 |
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container_title | Phytochemistry (Oxford) |
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creator | Doi, Fuminao Ohara, Taiga Ogamino, Takahisa Sugai, Takeshi Higashinakasu, Keiko Yamada, Kosumi Shigemori, Hideyuki Hasegawa, Koji Nishiyama, Shigeru |
description | Chromane and tetrahydro-oxepin derivatives related to heliannuols were submitted to assessment of plant-growth inhibitory activity.
In addition to (+)-, (−)- and (±)-heliannuol E, growth-inhibitory activities of five synthetic chromans and four tetrahydrobenzo[b]oxepins were examined against oat and cress. All heliannuol E isomers exhibited similar biological activities against cress, whereas when tested against oat roots, the unnatural optical isomer (+) showed no inhibitory activity. Four brominated chromans and two tetrahydrobenzo[b]oxepin derivatives also showed apparent inhibition against both cress and oat. |
doi_str_mv | 10.1016/j.phytochem.2004.03.035 |
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In addition to (+)-, (−)- and (±)-heliannuol E, growth-inhibitory activities of five synthetic chromans and four tetrahydrobenzo[b]oxepins were examined against oat and cress. All heliannuol E isomers exhibited similar biological activities against cress, whereas when tested against oat roots, the unnatural optical isomer (+) showed no inhibitory activity. Four brominated chromans and two tetrahydrobenzo[b]oxepin derivatives also showed apparent inhibition against both cress and oat.</description><identifier>ISSN: 0031-9422</identifier><identifier>EISSN: 1873-3700</identifier><identifier>DOI: 10.1016/j.phytochem.2004.03.035</identifier><identifier>PMID: 15231414</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject><![CDATA[Allelochemicals ; Avena - drug effects ; Avena - growth & development ; Avena sativa ; benzo(b)oxepin ; bioassays ; biochemical pathways ; Biological and medical sciences ; Bridged Bicyclo Compounds, Heterocyclic - isolation & purification ; Bridged Bicyclo Compounds, Heterocyclic - pharmacology ; Chemical agents ; Chemical constitution ; chemical structure ; chromans ; Compositae ; Cotyledon - drug effects ; Cotyledon - growth & development ; Flowers - chemistry ; Fundamental and applied biological sciences. Psychology ; Heliannuol ; heliannuols ; Helianthus - chemistry ; Helianthus annuus ; Helianthus annuus L ; Hypocotyl - drug effects ; Hypocotyl - growth & development ; isomers ; Lepidium sativum ; Lepidium sativum - drug effects ; Lepidium sativum - growth & development ; Molecular Conformation ; Molecular Structure ; phytochemicals ; plant growth control ; Plant Growth Regulators - isolation & purification ; Plant Growth Regulators - pharmacology ; Plant physiology and development ; Plant Roots - drug effects ; Plant Roots - growth & development ; Plant-growth inhibition ; Sesquiterpenes - isolation & purification ; Sesquiterpenes - pharmacology ; sesquiterpenoids ; Vegetative apparatus, growth and morphogenesis. Senescence]]></subject><ispartof>Phytochemistry (Oxford), 2004-05, Vol.65 (10), p.1405-1411</ispartof><rights>2004 Elsevier Ltd</rights><rights>2004 INIST-CNRS</rights><rights>Copyright 2004 Elsiever Ltd.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c487t-deeaaac4bd6dca86666db59a7433ca39165bfa433e6e39d73811675f95d702f03</citedby><cites>FETCH-LOGICAL-c487t-deeaaac4bd6dca86666db59a7433ca39165bfa433e6e39d73811675f95d702f03</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=15915769$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15231414$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Doi, Fuminao</creatorcontrib><creatorcontrib>Ohara, Taiga</creatorcontrib><creatorcontrib>Ogamino, Takahisa</creatorcontrib><creatorcontrib>Sugai, Takeshi</creatorcontrib><creatorcontrib>Higashinakasu, Keiko</creatorcontrib><creatorcontrib>Yamada, Kosumi</creatorcontrib><creatorcontrib>Shigemori, Hideyuki</creatorcontrib><creatorcontrib>Hasegawa, Koji</creatorcontrib><creatorcontrib>Nishiyama, Shigeru</creatorcontrib><title>Plant-growth inhibitory activity of heliannuol derivatives</title><title>Phytochemistry (Oxford)</title><addtitle>Phytochemistry</addtitle><description>Chromane and tetrahydro-oxepin derivatives related to heliannuols were submitted to assessment of plant-growth inhibitory activity.
In addition to (+)-, (−)- and (±)-heliannuol E, growth-inhibitory activities of five synthetic chromans and four tetrahydrobenzo[b]oxepins were examined against oat and cress. All heliannuol E isomers exhibited similar biological activities against cress, whereas when tested against oat roots, the unnatural optical isomer (+) showed no inhibitory activity. Four brominated chromans and two tetrahydrobenzo[b]oxepin derivatives also showed apparent inhibition against both cress and oat.</description><subject>Allelochemicals</subject><subject>Avena - drug effects</subject><subject>Avena - growth & development</subject><subject>Avena sativa</subject><subject>benzo(b)oxepin</subject><subject>bioassays</subject><subject>biochemical pathways</subject><subject>Biological and medical sciences</subject><subject>Bridged Bicyclo Compounds, Heterocyclic - isolation & purification</subject><subject>Bridged Bicyclo Compounds, Heterocyclic - pharmacology</subject><subject>Chemical agents</subject><subject>Chemical constitution</subject><subject>chemical structure</subject><subject>chromans</subject><subject>Compositae</subject><subject>Cotyledon - drug effects</subject><subject>Cotyledon - growth & development</subject><subject>Flowers - chemistry</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Heliannuol</subject><subject>heliannuols</subject><subject>Helianthus - chemistry</subject><subject>Helianthus annuus</subject><subject>Helianthus annuus L</subject><subject>Hypocotyl - drug effects</subject><subject>Hypocotyl - growth & development</subject><subject>isomers</subject><subject>Lepidium sativum</subject><subject>Lepidium sativum - drug effects</subject><subject>Lepidium sativum - growth & development</subject><subject>Molecular Conformation</subject><subject>Molecular Structure</subject><subject>phytochemicals</subject><subject>plant growth control</subject><subject>Plant Growth Regulators - isolation & purification</subject><subject>Plant Growth Regulators - pharmacology</subject><subject>Plant physiology and development</subject><subject>Plant Roots - drug effects</subject><subject>Plant Roots - growth & development</subject><subject>Plant-growth inhibition</subject><subject>Sesquiterpenes - isolation & purification</subject><subject>Sesquiterpenes - pharmacology</subject><subject>sesquiterpenoids</subject><subject>Vegetative apparatus, growth and morphogenesis. Senescence</subject><issn>0031-9422</issn><issn>1873-3700</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><recordid>eNqFkEtvEzEQgC1ERdPCX6B7gdum4_Ur5lZVQJEqFQl6trz2bNfRZh1sJyj_vq4SATeskazRfPPQR8gVhSUFKq_Xy-14KNGNuFl2AHwJrIZ4RRZ0pVjLFMBrsgBgtNW8687JRc5rABBCyjfknIqOUU75gnz6Ptm5tE8p_i5jE-Yx9KHEdGisK2EfyqGJQzPiFOw87-LUeExhb2sJ81tyNtgp47vTf0kev3z-eXvX3j98_XZ7c986vlKl9YjWWsd7L72zK1mf74W2ijPmLNNUin6wNUGJTHvFVpRKJQYtvIJuAHZJPh7nblP8tcNczCZkh1M9HOMumzpQAdeqguoIuhRzTjiYbQobmw6GgnnRZtbmjzbzos0AqyFq5_vTil2_Qf-37-SpAh9OgM3OTkOyswv5H05ToaSu3NWRG2w09ilV5vFHB5QBaM46wSpxcySwKtsHTCa7gLNDHxK6YnwM_z33Gey6mY0</recordid><startdate>20040501</startdate><enddate>20040501</enddate><creator>Doi, Fuminao</creator><creator>Ohara, Taiga</creator><creator>Ogamino, Takahisa</creator><creator>Sugai, Takeshi</creator><creator>Higashinakasu, Keiko</creator><creator>Yamada, Kosumi</creator><creator>Shigemori, Hideyuki</creator><creator>Hasegawa, Koji</creator><creator>Nishiyama, Shigeru</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>FBQ</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><scope>7X8</scope></search><sort><creationdate>20040501</creationdate><title>Plant-growth inhibitory activity of heliannuol derivatives</title><author>Doi, Fuminao ; Ohara, Taiga ; Ogamino, Takahisa ; Sugai, Takeshi ; Higashinakasu, Keiko ; Yamada, Kosumi ; Shigemori, Hideyuki ; Hasegawa, Koji ; Nishiyama, Shigeru</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c487t-deeaaac4bd6dca86666db59a7433ca39165bfa433e6e39d73811675f95d702f03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Allelochemicals</topic><topic>Avena - drug effects</topic><topic>Avena - growth & development</topic><topic>Avena sativa</topic><topic>benzo(b)oxepin</topic><topic>bioassays</topic><topic>biochemical pathways</topic><topic>Biological and medical sciences</topic><topic>Bridged Bicyclo Compounds, Heterocyclic - isolation & purification</topic><topic>Bridged Bicyclo Compounds, Heterocyclic - pharmacology</topic><topic>Chemical agents</topic><topic>Chemical constitution</topic><topic>chemical structure</topic><topic>chromans</topic><topic>Compositae</topic><topic>Cotyledon - drug effects</topic><topic>Cotyledon - growth & development</topic><topic>Flowers - chemistry</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Heliannuol</topic><topic>heliannuols</topic><topic>Helianthus - chemistry</topic><topic>Helianthus annuus</topic><topic>Helianthus annuus L</topic><topic>Hypocotyl - drug effects</topic><topic>Hypocotyl - growth & development</topic><topic>isomers</topic><topic>Lepidium sativum</topic><topic>Lepidium sativum - drug effects</topic><topic>Lepidium sativum - growth & development</topic><topic>Molecular Conformation</topic><topic>Molecular Structure</topic><topic>phytochemicals</topic><topic>plant growth control</topic><topic>Plant Growth Regulators - isolation & purification</topic><topic>Plant Growth Regulators - pharmacology</topic><topic>Plant physiology and development</topic><topic>Plant Roots - drug effects</topic><topic>Plant Roots - growth & development</topic><topic>Plant-growth inhibition</topic><topic>Sesquiterpenes - isolation & purification</topic><topic>Sesquiterpenes - pharmacology</topic><topic>sesquiterpenoids</topic><topic>Vegetative apparatus, growth and morphogenesis. Senescence</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Doi, Fuminao</creatorcontrib><creatorcontrib>Ohara, Taiga</creatorcontrib><creatorcontrib>Ogamino, Takahisa</creatorcontrib><creatorcontrib>Sugai, Takeshi</creatorcontrib><creatorcontrib>Higashinakasu, Keiko</creatorcontrib><creatorcontrib>Yamada, Kosumi</creatorcontrib><creatorcontrib>Shigemori, Hideyuki</creatorcontrib><creatorcontrib>Hasegawa, Koji</creatorcontrib><creatorcontrib>Nishiyama, Shigeru</creatorcontrib><collection>AGRIS</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><collection>MEDLINE - Academic</collection><jtitle>Phytochemistry (Oxford)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Doi, Fuminao</au><au>Ohara, Taiga</au><au>Ogamino, Takahisa</au><au>Sugai, Takeshi</au><au>Higashinakasu, Keiko</au><au>Yamada, Kosumi</au><au>Shigemori, Hideyuki</au><au>Hasegawa, Koji</au><au>Nishiyama, Shigeru</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Plant-growth inhibitory activity of heliannuol derivatives</atitle><jtitle>Phytochemistry (Oxford)</jtitle><addtitle>Phytochemistry</addtitle><date>2004-05-01</date><risdate>2004</risdate><volume>65</volume><issue>10</issue><spage>1405</spage><epage>1411</epage><pages>1405-1411</pages><issn>0031-9422</issn><eissn>1873-3700</eissn><abstract>Chromane and tetrahydro-oxepin derivatives related to heliannuols were submitted to assessment of plant-growth inhibitory activity.
In addition to (+)-, (−)- and (±)-heliannuol E, growth-inhibitory activities of five synthetic chromans and four tetrahydrobenzo[b]oxepins were examined against oat and cress. All heliannuol E isomers exhibited similar biological activities against cress, whereas when tested against oat roots, the unnatural optical isomer (+) showed no inhibitory activity. Four brominated chromans and two tetrahydrobenzo[b]oxepin derivatives also showed apparent inhibition against both cress and oat.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>15231414</pmid><doi>10.1016/j.phytochem.2004.03.035</doi><tpages>7</tpages></addata></record> |
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subjects | Allelochemicals Avena - drug effects Avena - growth & development Avena sativa benzo(b)oxepin bioassays biochemical pathways Biological and medical sciences Bridged Bicyclo Compounds, Heterocyclic - isolation & purification Bridged Bicyclo Compounds, Heterocyclic - pharmacology Chemical agents Chemical constitution chemical structure chromans Compositae Cotyledon - drug effects Cotyledon - growth & development Flowers - chemistry Fundamental and applied biological sciences. Psychology Heliannuol heliannuols Helianthus - chemistry Helianthus annuus Helianthus annuus L Hypocotyl - drug effects Hypocotyl - growth & development isomers Lepidium sativum Lepidium sativum - drug effects Lepidium sativum - growth & development Molecular Conformation Molecular Structure phytochemicals plant growth control Plant Growth Regulators - isolation & purification Plant Growth Regulators - pharmacology Plant physiology and development Plant Roots - drug effects Plant Roots - growth & development Plant-growth inhibition Sesquiterpenes - isolation & purification Sesquiterpenes - pharmacology sesquiterpenoids Vegetative apparatus, growth and morphogenesis. Senescence |
title | Plant-growth inhibitory activity of heliannuol derivatives |
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