Identification and quantitation of allelochemicals from the lichen Lethariella canariensis: phytotoxicity and antioxidative activity
Phytotoxicity-based extraction and fractionation were employed to separate allelochemicals contained in an extract of Lethariella canariensis. Twelve phenolic substances were isolated from the phytotoxic fraction "Letharal" of the thalli. These were identified by spectroscopic methods, phy...
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| Veröffentlicht in: | Journal of chemical ecology 2003-09, Vol.29 (9), p.2049-2071 |
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| creator | Toledo Marante, F.J Garcia Castellano, A Estevez Rosas, F Quintana Aguiar, J Bermejo Barrera, J |
| description | Phytotoxicity-based extraction and fractionation were employed to separate allelochemicals contained in an extract of Lethariella canariensis. Twelve phenolic substances were isolated from the phytotoxic fraction "Letharal" of the thalli. These were identified by spectroscopic methods, physicochemical constants, and HPLC chemical correlation, and determined to be atranol (2), chloroatranol (3), hematommic acid (4), chlorohematommic acid (5), methyl hematommate (6), methyl chlorohematommate (7) (new compound), ethyl hematommate (8), ethyl chlorohematommate (9), methyl beta-orsellinate (10), atranorin (11), chloroatranorin (12), and (+)-usnic acid (13). Further identification and quantification of these allelochemicals in the environment were conducted by HPLC. Several phenolic compounds showed moderate antimicrobial activity. The cytostatic activity of the polyphenols was investigated on U937 and HL-60 cells. All compounds were assayed, with the exception of 10. The "Letharal" mixture decreased cell viability in both cell lines. Protection against lipid peroxidation was investigated using brain homogenates. Compounds 2, 3, 6, 8, 11, and Letharal decreased H2O2/Fe+2 induced lipid peroxidation in a concentration-dependent manner, while 10 and 13 were unable to protect tissue against oxidative stress. |
| doi_str_mv | 10.1023/a:1025682318001 |
| format | Article |
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Twelve phenolic substances were isolated from the phytotoxic fraction "Letharal" of the thalli. These were identified by spectroscopic methods, physicochemical constants, and HPLC chemical correlation, and determined to be atranol (2), chloroatranol (3), hematommic acid (4), chlorohematommic acid (5), methyl hematommate (6), methyl chlorohematommate (7) (new compound), ethyl hematommate (8), ethyl chlorohematommate (9), methyl beta-orsellinate (10), atranorin (11), chloroatranorin (12), and (+)-usnic acid (13). Further identification and quantification of these allelochemicals in the environment were conducted by HPLC. Several phenolic compounds showed moderate antimicrobial activity. The cytostatic activity of the polyphenols was investigated on U937 and HL-60 cells. All compounds were assayed, with the exception of 10. The "Letharal" mixture decreased cell viability in both cell lines. Protection against lipid peroxidation was investigated using brain homogenates. Compounds 2, 3, 6, 8, 11, and Letharal decreased H2O2/Fe+2 induced lipid peroxidation in a concentration-dependent manner, while 10 and 13 were unable to protect tissue against oxidative stress.</description><identifier>ISSN: 0098-0331</identifier><identifier>EISSN: 1573-1561</identifier><identifier>DOI: 10.1023/a:1025682318001</identifier><identifier>PMID: 14584675</identifier><identifier>CODEN: JCECD8</identifier><language>eng</language><publisher>New York, NY: Springer</publisher><subject>allelochemicals ; Animal and plant ecology ; Animal, plant and microbial ecology ; Animals ; antioxidant activity ; Antioxidants ; Antioxidants - pharmacology ; Autoecology ; Biological and medical sciences ; Brain ; chemical composition ; Chromatography, High Pressure Liquid ; Fractionation ; Fundamental and applied biological sciences. Psychology ; HL-60 Cells ; Humans ; Lethariella canariensis ; lichens ; Lichens - chemistry ; Lipid Peroxidation ; Liquid chromatography ; Microbial Sensitivity Tests ; Oxidative Stress ; Peroxidation ; phenolic compounds ; Phenols ; Phenols - isolation & purification ; Phenols - pharmacology ; Phenols - toxicity ; Phytotoxicity ; Plants and fungi ; polyphenols ; quantitative analysis ; Rats ; Rats, Sprague-Dawley</subject><ispartof>Journal of chemical ecology, 2003-09, Vol.29 (9), p.2049-2071</ispartof><rights>2004 INIST-CNRS</rights><rights>Plenum Publishing Corporation 2003</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c477t-eafb661aec651041c5155a7f8cbbffc1b87bc3e952d6adb6b1e4396a4ef1225c3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27903,27904</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=15165880$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/14584675$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Toledo Marante, F.J</creatorcontrib><creatorcontrib>Garcia Castellano, A</creatorcontrib><creatorcontrib>Estevez Rosas, F</creatorcontrib><creatorcontrib>Quintana Aguiar, J</creatorcontrib><creatorcontrib>Bermejo Barrera, J</creatorcontrib><title>Identification and quantitation of allelochemicals from the lichen Lethariella canariensis: phytotoxicity and antioxidative activity</title><title>Journal of chemical ecology</title><addtitle>J Chem Ecol</addtitle><description>Phytotoxicity-based extraction and fractionation were employed to separate allelochemicals contained in an extract of Lethariella canariensis. Twelve phenolic substances were isolated from the phytotoxic fraction "Letharal" of the thalli. These were identified by spectroscopic methods, physicochemical constants, and HPLC chemical correlation, and determined to be atranol (2), chloroatranol (3), hematommic acid (4), chlorohematommic acid (5), methyl hematommate (6), methyl chlorohematommate (7) (new compound), ethyl hematommate (8), ethyl chlorohematommate (9), methyl beta-orsellinate (10), atranorin (11), chloroatranorin (12), and (+)-usnic acid (13). Further identification and quantification of these allelochemicals in the environment were conducted by HPLC. Several phenolic compounds showed moderate antimicrobial activity. The cytostatic activity of the polyphenols was investigated on U937 and HL-60 cells. All compounds were assayed, with the exception of 10. The "Letharal" mixture decreased cell viability in both cell lines. Protection against lipid peroxidation was investigated using brain homogenates. Compounds 2, 3, 6, 8, 11, and Letharal decreased H2O2/Fe+2 induced lipid peroxidation in a concentration-dependent manner, while 10 and 13 were unable to protect tissue against oxidative stress.</description><subject>allelochemicals</subject><subject>Animal and plant ecology</subject><subject>Animal, plant and microbial ecology</subject><subject>Animals</subject><subject>antioxidant activity</subject><subject>Antioxidants</subject><subject>Antioxidants - pharmacology</subject><subject>Autoecology</subject><subject>Biological and medical sciences</subject><subject>Brain</subject><subject>chemical composition</subject><subject>Chromatography, High Pressure Liquid</subject><subject>Fractionation</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>HL-60 Cells</subject><subject>Humans</subject><subject>Lethariella canariensis</subject><subject>lichens</subject><subject>Lichens - chemistry</subject><subject>Lipid Peroxidation</subject><subject>Liquid chromatography</subject><subject>Microbial Sensitivity Tests</subject><subject>Oxidative Stress</subject><subject>Peroxidation</subject><subject>phenolic compounds</subject><subject>Phenols</subject><subject>Phenols - isolation & purification</subject><subject>Phenols - pharmacology</subject><subject>Phenols - toxicity</subject><subject>Phytotoxicity</subject><subject>Plants and fungi</subject><subject>polyphenols</subject><subject>quantitative analysis</subject><subject>Rats</subject><subject>Rats, Sprague-Dawley</subject><issn>0098-0331</issn><issn>1573-1561</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><sourceid>BENPR</sourceid><recordid>eNpdkUtv1DAURq2qqB0K6-6ohQS7gG8cP9IdqnhUGolF23V049iMq8Sexg5i9vxwPMxUSKw--_PR0dU1IZfAPgCr-Ue8LiGkrjloxuCErEAoXoGQcEpWjLW6YpzDOXmZ0iNjrJZanJFzaIRupBIr8vt2sCF75w1mHwPFMNCnBUuVD0V0FMfRjtFs7FSoMVE3x4nmjaWjL2Wga5s3OHs7jkgNhv0xJJ-u6XazyzHHX974vPur3ovLfSjun5aiKVGeXpEXrojt62NekIcvn-9vvlXr719vbz6tK9MolSuLrpcS0BopgDVgBAiBymnT984Z6LXqDbetqAeJQy97sA1vJTbWQV0Lwy_I-4N3O8enxabcTT6Z_dzBxiV1oFsBLbQFfPsf-BiXOZTZOsU5qxslmgK9OUJLP9mh285-wnnXPS-3AO-OAKayODdjMD794wRIoTUr3NWBcxg7_DEX5uGuZsDL_wmtZMv_AIH3lbo</recordid><startdate>20030901</startdate><enddate>20030901</enddate><creator>Toledo Marante, F.J</creator><creator>Garcia Castellano, A</creator><creator>Estevez Rosas, F</creator><creator>Quintana Aguiar, J</creator><creator>Bermejo Barrera, J</creator><general>Springer</general><general>Springer Nature B.V</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>3V.</scope><scope>7QG</scope><scope>7QR</scope><scope>7SN</scope><scope>7SS</scope><scope>7U7</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>88I</scope><scope>8AO</scope><scope>8C1</scope><scope>8FD</scope><scope>8FE</scope><scope>8FG</scope><scope>8FH</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABJCF</scope><scope>ABUWG</scope><scope>AEUYN</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BBNVY</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>BHPHI</scope><scope>BKSAR</scope><scope>C1K</scope><scope>CCPQU</scope><scope>D1I</scope><scope>DWQXO</scope><scope>FR3</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>HCIFZ</scope><scope>K9.</scope><scope>KB.</scope><scope>LK8</scope><scope>M0S</scope><scope>M1P</scope><scope>M2P</scope><scope>M7N</scope><scope>M7P</scope><scope>P64</scope><scope>PCBAR</scope><scope>PDBOC</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>Q9U</scope><scope>RC3</scope></search><sort><creationdate>20030901</creationdate><title>Identification and quantitation of allelochemicals from the lichen Lethariella canariensis: phytotoxicity and antioxidative activity</title><author>Toledo Marante, F.J ; Garcia Castellano, A ; Estevez Rosas, F ; Quintana Aguiar, J ; Bermejo Barrera, J</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c477t-eafb661aec651041c5155a7f8cbbffc1b87bc3e952d6adb6b1e4396a4ef1225c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>allelochemicals</topic><topic>Animal and plant ecology</topic><topic>Animal, plant and microbial ecology</topic><topic>Animals</topic><topic>antioxidant activity</topic><topic>Antioxidants</topic><topic>Antioxidants - pharmacology</topic><topic>Autoecology</topic><topic>Biological and medical sciences</topic><topic>Brain</topic><topic>chemical composition</topic><topic>Chromatography, High Pressure Liquid</topic><topic>Fractionation</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>HL-60 Cells</topic><topic>Humans</topic><topic>Lethariella canariensis</topic><topic>lichens</topic><topic>Lichens - chemistry</topic><topic>Lipid Peroxidation</topic><topic>Liquid chromatography</topic><topic>Microbial Sensitivity Tests</topic><topic>Oxidative Stress</topic><topic>Peroxidation</topic><topic>phenolic compounds</topic><topic>Phenols</topic><topic>Phenols - isolation & purification</topic><topic>Phenols - pharmacology</topic><topic>Phenols - toxicity</topic><topic>Phytotoxicity</topic><topic>Plants and fungi</topic><topic>polyphenols</topic><topic>quantitative analysis</topic><topic>Rats</topic><topic>Rats, Sprague-Dawley</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Toledo Marante, F.J</creatorcontrib><creatorcontrib>Garcia Castellano, A</creatorcontrib><creatorcontrib>Estevez Rosas, F</creatorcontrib><creatorcontrib>Quintana Aguiar, J</creatorcontrib><creatorcontrib>Bermejo Barrera, 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Ecol</addtitle><date>2003-09-01</date><risdate>2003</risdate><volume>29</volume><issue>9</issue><spage>2049</spage><epage>2071</epage><pages>2049-2071</pages><issn>0098-0331</issn><eissn>1573-1561</eissn><coden>JCECD8</coden><abstract>Phytotoxicity-based extraction and fractionation were employed to separate allelochemicals contained in an extract of Lethariella canariensis. Twelve phenolic substances were isolated from the phytotoxic fraction "Letharal" of the thalli. These were identified by spectroscopic methods, physicochemical constants, and HPLC chemical correlation, and determined to be atranol (2), chloroatranol (3), hematommic acid (4), chlorohematommic acid (5), methyl hematommate (6), methyl chlorohematommate (7) (new compound), ethyl hematommate (8), ethyl chlorohematommate (9), methyl beta-orsellinate (10), atranorin (11), chloroatranorin (12), and (+)-usnic acid (13). Further identification and quantification of these allelochemicals in the environment were conducted by HPLC. Several phenolic compounds showed moderate antimicrobial activity. The cytostatic activity of the polyphenols was investigated on U937 and HL-60 cells. All compounds were assayed, with the exception of 10. The "Letharal" mixture decreased cell viability in both cell lines. Protection against lipid peroxidation was investigated using brain homogenates. Compounds 2, 3, 6, 8, 11, and Letharal decreased H2O2/Fe+2 induced lipid peroxidation in a concentration-dependent manner, while 10 and 13 were unable to protect tissue against oxidative stress.</abstract><cop>New York, NY</cop><pub>Springer</pub><pmid>14584675</pmid><doi>10.1023/a:1025682318001</doi><tpages>23</tpages></addata></record> |
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| subjects | allelochemicals Animal and plant ecology Animal, plant and microbial ecology Animals antioxidant activity Antioxidants Antioxidants - pharmacology Autoecology Biological and medical sciences Brain chemical composition Chromatography, High Pressure Liquid Fractionation Fundamental and applied biological sciences. Psychology HL-60 Cells Humans Lethariella canariensis lichens Lichens - chemistry Lipid Peroxidation Liquid chromatography Microbial Sensitivity Tests Oxidative Stress Peroxidation phenolic compounds Phenols Phenols - isolation & purification Phenols - pharmacology Phenols - toxicity Phytotoxicity Plants and fungi polyphenols quantitative analysis Rats Rats, Sprague-Dawley |
| title | Identification and quantitation of allelochemicals from the lichen Lethariella canariensis: phytotoxicity and antioxidative activity |
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