Antifungal Activity of CHE-23C, a Dimeric Sesquiterpene from Chloranthus henryi
An antifungal compound was isolated from methanol extracts of stems and roots of Chloranthus henryi Hemsl. using ethyl acetate extraction and various chromatographic techniques. On the basis of spectroscopic analyses including mass and various NMR, the structure of the compound was identified as a d...
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| Veröffentlicht in: | Journal of agricultural and food chemistry 2009-07, Vol.57 (13), p.5750-5755 |
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| container_title | Journal of agricultural and food chemistry |
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| creator | Lee, Yun Mi Moon, Jae Sun Yun, Bong-Sik Park, Ki Duk Choi, Gyung Ja Kim, Jin-Cheol Lee, Sang Han Kim, Sung Uk |
| description | An antifungal compound was isolated from methanol extracts of stems and roots of Chloranthus henryi Hemsl. using ethyl acetate extraction and various chromatographic techniques. On the basis of spectroscopic analyses including mass and various NMR, the structure of the compound was identified as a dimeric sesquiterpene, CHE-23C. The compound showed potent antifungal activities (MICs = 1−32 μg/mL) in vitro against various phytopathogenic fungi such as Alternaria kikuchiana, Botrytis cinerea, Colletotrichum lagenarium, Magnaporthe grisea, Pythium ultimum, and Phytophthora infestans. In particular, it exhibited 91 and 100% disease-control activity in vivo against tomato late blight (P. infestans) and wheat leaf rust (Puccinia recondita) at concentrations of 33 and 100 μg/mL, respectively. The disease-control activity of this compound was stronger than that of the commercially available fungicide chlorothalonil, but weaker than that of dimethomorph. Therefore, the compound might serve as an interesting lead to develop effective antifungal agents. |
| doi_str_mv | 10.1021/jf900674y |
| format | Article |
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On the basis of spectroscopic analyses including mass and various NMR, the structure of the compound was identified as a dimeric sesquiterpene, CHE-23C. The compound showed potent antifungal activities (MICs = 1−32 μg/mL) in vitro against various phytopathogenic fungi such as Alternaria kikuchiana, Botrytis cinerea, Colletotrichum lagenarium, Magnaporthe grisea, Pythium ultimum, and Phytophthora infestans. In particular, it exhibited 91 and 100% disease-control activity in vivo against tomato late blight (P. infestans) and wheat leaf rust (Puccinia recondita) at concentrations of 33 and 100 μg/mL, respectively. The disease-control activity of this compound was stronger than that of the commercially available fungicide chlorothalonil, but weaker than that of dimethomorph. Therefore, the compound might serve as an interesting lead to develop effective antifungal agents.</description><identifier>ISSN: 0021-8561</identifier><identifier>EISSN: 1520-5118</identifier><identifier>DOI: 10.1021/jf900674y</identifier><identifier>PMID: 19566082</identifier><identifier>CODEN: JAFCAU</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>antifungal properties ; Basidiomycota - drug effects ; Bioactive Constituents ; Biological and medical sciences ; chemical structure ; Chloranthus ; Chloranthus henryi ; chlorothalonil ; Food industries ; Fundamental and applied biological sciences. Psychology ; Fungi - drug effects ; Fungicides, Industrial - chemistry ; Fungicides, Industrial - isolation & purification ; Fungicides, Industrial - pharmacology ; in vitro studies ; in vivo studies ; Magnoliopsida - chemistry ; mass spectrometry ; medicinal plants ; medicinal properties ; minimum inhibitory concentration ; nuclear magnetic resonance spectroscopy ; Phytophthora infestans - drug effects ; Plant Diseases - microbiology ; plant extracts ; plant pathogenic fungi ; Plant Roots - chemistry ; Plant Stems - chemistry ; roots ; Sesquiterpenes - chemistry ; Sesquiterpenes - isolation & purification ; Sesquiterpenes - pharmacology ; sesquiterpenoids ; stems</subject><ispartof>Journal of agricultural and food chemistry, 2009-07, Vol.57 (13), p.5750-5755</ispartof><rights>Copyright © 2009 American Chemical Society</rights><rights>2009 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a367t-cc98e595324d3d59e00865cd40c613407c9aab12e9ab86c673e7ddf2e5593e223</citedby><cites>FETCH-LOGICAL-a367t-cc98e595324d3d59e00865cd40c613407c9aab12e9ab86c673e7ddf2e5593e223</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jf900674y$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jf900674y$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=22082456$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19566082$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Lee, Yun Mi</creatorcontrib><creatorcontrib>Moon, Jae Sun</creatorcontrib><creatorcontrib>Yun, Bong-Sik</creatorcontrib><creatorcontrib>Park, Ki Duk</creatorcontrib><creatorcontrib>Choi, Gyung Ja</creatorcontrib><creatorcontrib>Kim, Jin-Cheol</creatorcontrib><creatorcontrib>Lee, Sang Han</creatorcontrib><creatorcontrib>Kim, Sung Uk</creatorcontrib><title>Antifungal Activity of CHE-23C, a Dimeric Sesquiterpene from Chloranthus henryi</title><title>Journal of agricultural and food chemistry</title><addtitle>J. Agric. Food Chem</addtitle><description>An antifungal compound was isolated from methanol extracts of stems and roots of Chloranthus henryi Hemsl. using ethyl acetate extraction and various chromatographic techniques. On the basis of spectroscopic analyses including mass and various NMR, the structure of the compound was identified as a dimeric sesquiterpene, CHE-23C. The compound showed potent antifungal activities (MICs = 1−32 μg/mL) in vitro against various phytopathogenic fungi such as Alternaria kikuchiana, Botrytis cinerea, Colletotrichum lagenarium, Magnaporthe grisea, Pythium ultimum, and Phytophthora infestans. In particular, it exhibited 91 and 100% disease-control activity in vivo against tomato late blight (P. infestans) and wheat leaf rust (Puccinia recondita) at concentrations of 33 and 100 μg/mL, respectively. The disease-control activity of this compound was stronger than that of the commercially available fungicide chlorothalonil, but weaker than that of dimethomorph. Therefore, the compound might serve as an interesting lead to develop effective antifungal agents.</description><subject>antifungal properties</subject><subject>Basidiomycota - drug effects</subject><subject>Bioactive Constituents</subject><subject>Biological and medical sciences</subject><subject>chemical structure</subject><subject>Chloranthus</subject><subject>Chloranthus henryi</subject><subject>chlorothalonil</subject><subject>Food industries</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Fungi - drug effects</subject><subject>Fungicides, Industrial - chemistry</subject><subject>Fungicides, Industrial - isolation & purification</subject><subject>Fungicides, Industrial - pharmacology</subject><subject>in vitro studies</subject><subject>in vivo studies</subject><subject>Magnoliopsida - chemistry</subject><subject>mass spectrometry</subject><subject>medicinal plants</subject><subject>medicinal properties</subject><subject>minimum inhibitory concentration</subject><subject>nuclear magnetic resonance spectroscopy</subject><subject>Phytophthora infestans - drug effects</subject><subject>Plant Diseases - microbiology</subject><subject>plant extracts</subject><subject>plant pathogenic fungi</subject><subject>Plant Roots - chemistry</subject><subject>Plant Stems - chemistry</subject><subject>roots</subject><subject>Sesquiterpenes - chemistry</subject><subject>Sesquiterpenes - isolation & purification</subject><subject>Sesquiterpenes - pharmacology</subject><subject>sesquiterpenoids</subject><subject>stems</subject><issn>0021-8561</issn><issn>1520-5118</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0LFOwzAQBmALgWgpDLwAeGFAInC2YycZq1AoUqUOpXPkOnbrKk2KnSDl7TFqRRemG-7Tr7sfoVsCzwQoedmaDEAkcX-GhoRTiDgh6TkaQlhGKRdkgK683wJAyhO4RAOScSEgpUM0H9etNV29lhUeq9Z-27bHjcH5dBJRlj9hiV_tTjur8EL7r8622u11rbFxzQ7nm6pxsm43nccbXbveXqMLIyuvb45zhJZvk898Gs3m7x_5eBZJJpI2UipLNc84o3HJSp7pcJrgqoxBCcJiSFQm5YpQnclVKpRImE7K0lDNecY0pWyEHg-5yjXeO22KvbM76fqCQPFbSvFXSrB3B7vvVjtdnuSxhQAejkB6JSsTXlLW_zlKA4q5CO7-4IxsCrl2wSwXFAgDIjgHmpySpPLFtulcHUr456Qf9tR9bA</recordid><startdate>20090708</startdate><enddate>20090708</enddate><creator>Lee, Yun Mi</creator><creator>Moon, Jae Sun</creator><creator>Yun, Bong-Sik</creator><creator>Park, Ki Duk</creator><creator>Choi, Gyung Ja</creator><creator>Kim, Jin-Cheol</creator><creator>Lee, Sang Han</creator><creator>Kim, Sung Uk</creator><general>American Chemical Society</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></search><sort><creationdate>20090708</creationdate><title>Antifungal Activity of CHE-23C, a Dimeric Sesquiterpene from Chloranthus henryi</title><author>Lee, Yun Mi ; Moon, Jae Sun ; Yun, Bong-Sik ; Park, Ki Duk ; Choi, Gyung Ja ; Kim, Jin-Cheol ; Lee, Sang Han ; Kim, Sung Uk</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a367t-cc98e595324d3d59e00865cd40c613407c9aab12e9ab86c673e7ddf2e5593e223</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>antifungal properties</topic><topic>Basidiomycota - drug effects</topic><topic>Bioactive Constituents</topic><topic>Biological and medical sciences</topic><topic>chemical structure</topic><topic>Chloranthus</topic><topic>Chloranthus henryi</topic><topic>chlorothalonil</topic><topic>Food industries</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Fungi - drug effects</topic><topic>Fungicides, Industrial - chemistry</topic><topic>Fungicides, Industrial - isolation & purification</topic><topic>Fungicides, Industrial - pharmacology</topic><topic>in vitro studies</topic><topic>in vivo studies</topic><topic>Magnoliopsida - chemistry</topic><topic>mass spectrometry</topic><topic>medicinal plants</topic><topic>medicinal properties</topic><topic>minimum inhibitory concentration</topic><topic>nuclear magnetic resonance spectroscopy</topic><topic>Phytophthora infestans - drug effects</topic><topic>Plant Diseases - microbiology</topic><topic>plant extracts</topic><topic>plant pathogenic fungi</topic><topic>Plant Roots - chemistry</topic><topic>Plant Stems - chemistry</topic><topic>roots</topic><topic>Sesquiterpenes - chemistry</topic><topic>Sesquiterpenes - isolation & purification</topic><topic>Sesquiterpenes - pharmacology</topic><topic>sesquiterpenoids</topic><topic>stems</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lee, Yun Mi</creatorcontrib><creatorcontrib>Moon, Jae Sun</creatorcontrib><creatorcontrib>Yun, Bong-Sik</creatorcontrib><creatorcontrib>Park, Ki Duk</creatorcontrib><creatorcontrib>Choi, Gyung Ja</creatorcontrib><creatorcontrib>Kim, Jin-Cheol</creatorcontrib><creatorcontrib>Lee, Sang Han</creatorcontrib><creatorcontrib>Kim, Sung Uk</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><jtitle>Journal of agricultural and food chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Lee, Yun Mi</au><au>Moon, Jae Sun</au><au>Yun, Bong-Sik</au><au>Park, Ki Duk</au><au>Choi, Gyung Ja</au><au>Kim, Jin-Cheol</au><au>Lee, Sang Han</au><au>Kim, Sung Uk</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Antifungal Activity of CHE-23C, a Dimeric Sesquiterpene from Chloranthus henryi</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>2009-07-08</date><risdate>2009</risdate><volume>57</volume><issue>13</issue><spage>5750</spage><epage>5755</epage><pages>5750-5755</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><coden>JAFCAU</coden><abstract>An antifungal compound was isolated from methanol extracts of stems and roots of Chloranthus henryi Hemsl. using ethyl acetate extraction and various chromatographic techniques. On the basis of spectroscopic analyses including mass and various NMR, the structure of the compound was identified as a dimeric sesquiterpene, CHE-23C. The compound showed potent antifungal activities (MICs = 1−32 μg/mL) in vitro against various phytopathogenic fungi such as Alternaria kikuchiana, Botrytis cinerea, Colletotrichum lagenarium, Magnaporthe grisea, Pythium ultimum, and Phytophthora infestans. In particular, it exhibited 91 and 100% disease-control activity in vivo against tomato late blight (P. infestans) and wheat leaf rust (Puccinia recondita) at concentrations of 33 and 100 μg/mL, respectively. The disease-control activity of this compound was stronger than that of the commercially available fungicide chlorothalonil, but weaker than that of dimethomorph. Therefore, the compound might serve as an interesting lead to develop effective antifungal agents.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>19566082</pmid><doi>10.1021/jf900674y</doi><tpages>6</tpages></addata></record> |
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| source | ACS Publications; MEDLINE |
| subjects | antifungal properties Basidiomycota - drug effects Bioactive Constituents Biological and medical sciences chemical structure Chloranthus Chloranthus henryi chlorothalonil Food industries Fundamental and applied biological sciences. Psychology Fungi - drug effects Fungicides, Industrial - chemistry Fungicides, Industrial - isolation & purification Fungicides, Industrial - pharmacology in vitro studies in vivo studies Magnoliopsida - chemistry mass spectrometry medicinal plants medicinal properties minimum inhibitory concentration nuclear magnetic resonance spectroscopy Phytophthora infestans - drug effects Plant Diseases - microbiology plant extracts plant pathogenic fungi Plant Roots - chemistry Plant Stems - chemistry roots Sesquiterpenes - chemistry Sesquiterpenes - isolation & purification Sesquiterpenes - pharmacology sesquiterpenoids stems |
| title | Antifungal Activity of CHE-23C, a Dimeric Sesquiterpene from Chloranthus henryi |
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