Antifungal activity of β-carbolines on Penicillium digitatum and Botrytis cinerea
β-carbolines (βCs) are alkaloids widely distributed in nature that have demonstrated antimicrobial properties. Here, we tested in vitro six βCs against Penicillium digitatum and Botrytis cinerea, causal agents of postharvest diseases on fruit and vegetables. Full aromatic βCs (harmine, harmol, norha...
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Veröffentlicht in: | Food microbiology 2017-04, Vol.62, p.9-14 |
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description | β-carbolines (βCs) are alkaloids widely distributed in nature that have demonstrated antimicrobial properties. Here, we tested in vitro six βCs against Penicillium digitatum and Botrytis cinerea, causal agents of postharvest diseases on fruit and vegetables. Full aromatic βCs (harmine, harmol, norharmane and harmane) exhibited a marked inhibitory effect on conidia germination at concentrations between 0.5 and 1 mM, while dihydro-βCs (harmalina and harmalol) only caused germination delay. Harmol showed the highest inhibitory effect on both fungal pathogens. After 24 h of exposure to 1 mM harmol, conidia revealed a severe cellular damage, exhibiting disorganized cytoplasm and thickened cell wall. Harmol antimicrobial effect was fungicidal on B. cinerea, while it was fungistatic on P. digitatum. Conidia membrane permeabilization was detected in treatments with harmol at sub-inhibitory and inhibitory concentrations, for both pathogens. In addition, residual infectivity of P. digitatum on lemons and B. cinerea on blueberries was significantly reduced after exposure to this alkaloid. It also inhibited mycelial growth, preventing sporulation at the highest concentration tested. These results indicate that harmol might be a promising candidate as a new antifungal molecule to control causal agents of fruit diseases.
•Full aromatic β-carbolines have inhibitory effect on P. digitatum and B. cinerea.•The β-carboline harmol has the highest inhibitory effect.•Harmol causes membrane permeabilization and cellular damage.•Fungi infectivity on fruit is significantly reduced after exposure to harmol. |
doi_str_mv | 10.1016/j.fm.2016.09.011 |
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•Full aromatic β-carbolines have inhibitory effect on P. digitatum and B. cinerea.•The β-carboline harmol has the highest inhibitory effect.•Harmol causes membrane permeabilization and cellular damage.•Fungi infectivity on fruit is significantly reduced after exposure to harmol.</description><identifier>ISSN: 0740-0020</identifier><identifier>EISSN: 1095-9998</identifier><identifier>DOI: 10.1016/j.fm.2016.09.011</identifier><identifier>PMID: 27889171</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Alkaloids ; Botrytis - cytology ; Botrytis - drug effects ; Botrytis - ultrastructure ; Botrytis cinerea ; Carbolines - pharmacology ; Citrus - microbiology ; Conidial membrane permeabilization ; Fruit - microbiology ; Fungicides, Industrial - pharmacology ; Germination - drug effects ; Germination inhibition ; Harmine - analogs & derivatives ; Harmine - pharmacology ; Harmol ; Infectivity ; Microbial Sensitivity Tests ; Mycelium - drug effects ; Penicillium - cytology ; Penicillium - drug effects ; Penicillium - ultrastructure ; Penicillium digitatum ; Phytopathogens ; Spores, Fungal - drug effects ; Spores, Fungal - physiology ; Vaccinium</subject><ispartof>Food microbiology, 2017-04, Vol.62, p.9-14</ispartof><rights>2016 Elsevier Ltd</rights><rights>Copyright © 2016 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c425t-92b78479d922d298fd86865fbc6bc6a30cb56c338d813195bdc44a029851fd413</citedby><cites>FETCH-LOGICAL-c425t-92b78479d922d298fd86865fbc6bc6a30cb56c338d813195bdc44a029851fd413</cites><orcidid>0000-0001-9584-4369</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0740002015302549$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3536,27903,27904,65309</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/27889171$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Olmedo, Gabriela M.</creatorcontrib><creatorcontrib>Cerioni, Luciana</creatorcontrib><creatorcontrib>González, M. Micaela</creatorcontrib><creatorcontrib>Cabrerizo, Franco M.</creatorcontrib><creatorcontrib>Rapisarda, Viviana A.</creatorcontrib><creatorcontrib>Volentini, Sabrina I.</creatorcontrib><title>Antifungal activity of β-carbolines on Penicillium digitatum and Botrytis cinerea</title><title>Food microbiology</title><addtitle>Food Microbiol</addtitle><description>β-carbolines (βCs) are alkaloids widely distributed in nature that have demonstrated antimicrobial properties. Here, we tested in vitro six βCs against Penicillium digitatum and Botrytis cinerea, causal agents of postharvest diseases on fruit and vegetables. Full aromatic βCs (harmine, harmol, norharmane and harmane) exhibited a marked inhibitory effect on conidia germination at concentrations between 0.5 and 1 mM, while dihydro-βCs (harmalina and harmalol) only caused germination delay. Harmol showed the highest inhibitory effect on both fungal pathogens. After 24 h of exposure to 1 mM harmol, conidia revealed a severe cellular damage, exhibiting disorganized cytoplasm and thickened cell wall. Harmol antimicrobial effect was fungicidal on B. cinerea, while it was fungistatic on P. digitatum. Conidia membrane permeabilization was detected in treatments with harmol at sub-inhibitory and inhibitory concentrations, for both pathogens. In addition, residual infectivity of P. digitatum on lemons and B. cinerea on blueberries was significantly reduced after exposure to this alkaloid. It also inhibited mycelial growth, preventing sporulation at the highest concentration tested. These results indicate that harmol might be a promising candidate as a new antifungal molecule to control causal agents of fruit diseases.
•Full aromatic β-carbolines have inhibitory effect on P. digitatum and B. cinerea.•The β-carboline harmol has the highest inhibitory effect.•Harmol causes membrane permeabilization and cellular damage.•Fungi infectivity on fruit is significantly reduced after exposure to harmol.</description><subject>Alkaloids</subject><subject>Botrytis - cytology</subject><subject>Botrytis - drug effects</subject><subject>Botrytis - ultrastructure</subject><subject>Botrytis cinerea</subject><subject>Carbolines - pharmacology</subject><subject>Citrus - microbiology</subject><subject>Conidial membrane permeabilization</subject><subject>Fruit - microbiology</subject><subject>Fungicides, Industrial - pharmacology</subject><subject>Germination - drug effects</subject><subject>Germination inhibition</subject><subject>Harmine - analogs & derivatives</subject><subject>Harmine - pharmacology</subject><subject>Harmol</subject><subject>Infectivity</subject><subject>Microbial Sensitivity Tests</subject><subject>Mycelium - drug effects</subject><subject>Penicillium - cytology</subject><subject>Penicillium - drug effects</subject><subject>Penicillium - ultrastructure</subject><subject>Penicillium digitatum</subject><subject>Phytopathogens</subject><subject>Spores, Fungal - drug effects</subject><subject>Spores, Fungal - physiology</subject><subject>Vaccinium</subject><issn>0740-0020</issn><issn>1095-9998</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp1kMtKAzEUhoMoWqt7VzJLNzOezC2Ju1q8QUERXYdMLiVlLjXJFPpaPojPZErVnXDgnMX3_3A-hC4wZBhwfb3KTJfl8cqAZYDxAZpgYFXKGKOHaAKkhBQghxN06v0KIlEV7Bid5IRShgmeoNdZH6wZ-6VoEyGD3diwTQaTfH2mUrhmaG2vfTL0yYvurbRta8cuUXZpgwjxEr1KbofgtsH6REbWaXGGjoxovT7_2VP0fn_3Nn9MF88PT_PZIpVlXoWU5Q2hJWGK5bnKGTWK1rSuTCPrOKIA2VS1LAqqKC4wqxoly1JAJCtsVImLKbra967d8DFqH3hnvdRtK3o9jJ5jWgEhBdQkorBHpRu8d9rwtbOdcFuOge9M8hU3Hd-Z5MB49BQjlz_tY9Np9Rf4VReBmz2g448bqx330upeamWdloGrwf7f_g0ke4OL</recordid><startdate>201704</startdate><enddate>201704</enddate><creator>Olmedo, Gabriela M.</creator><creator>Cerioni, Luciana</creator><creator>González, M. Micaela</creator><creator>Cabrerizo, Franco M.</creator><creator>Rapisarda, Viviana A.</creator><creator>Volentini, Sabrina I.</creator><general>Elsevier Ltd</general><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>7T2</scope><scope>7T7</scope><scope>7U2</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>M7N</scope><scope>P64</scope><orcidid>https://orcid.org/0000-0001-9584-4369</orcidid></search><sort><creationdate>201704</creationdate><title>Antifungal activity of β-carbolines on Penicillium digitatum and Botrytis cinerea</title><author>Olmedo, Gabriela M. ; Cerioni, Luciana ; González, M. Micaela ; Cabrerizo, Franco M. ; Rapisarda, Viviana A. ; Volentini, Sabrina I.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c425t-92b78479d922d298fd86865fbc6bc6a30cb56c338d813195bdc44a029851fd413</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Alkaloids</topic><topic>Botrytis - cytology</topic><topic>Botrytis - drug effects</topic><topic>Botrytis - ultrastructure</topic><topic>Botrytis cinerea</topic><topic>Carbolines - pharmacology</topic><topic>Citrus - microbiology</topic><topic>Conidial membrane permeabilization</topic><topic>Fruit - microbiology</topic><topic>Fungicides, Industrial - pharmacology</topic><topic>Germination - drug effects</topic><topic>Germination inhibition</topic><topic>Harmine - analogs & derivatives</topic><topic>Harmine - pharmacology</topic><topic>Harmol</topic><topic>Infectivity</topic><topic>Microbial Sensitivity Tests</topic><topic>Mycelium - drug effects</topic><topic>Penicillium - cytology</topic><topic>Penicillium - drug effects</topic><topic>Penicillium - ultrastructure</topic><topic>Penicillium digitatum</topic><topic>Phytopathogens</topic><topic>Spores, Fungal - drug effects</topic><topic>Spores, Fungal - physiology</topic><topic>Vaccinium</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Olmedo, Gabriela M.</creatorcontrib><creatorcontrib>Cerioni, Luciana</creatorcontrib><creatorcontrib>González, M. Micaela</creatorcontrib><creatorcontrib>Cabrerizo, Franco M.</creatorcontrib><creatorcontrib>Rapisarda, Viviana A.</creatorcontrib><creatorcontrib>Volentini, Sabrina I.</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Health and Safety Science Abstracts (Full archive)</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Safety Science and Risk</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Food microbiology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Olmedo, Gabriela M.</au><au>Cerioni, Luciana</au><au>González, M. Micaela</au><au>Cabrerizo, Franco M.</au><au>Rapisarda, Viviana A.</au><au>Volentini, Sabrina I.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Antifungal activity of β-carbolines on Penicillium digitatum and Botrytis cinerea</atitle><jtitle>Food microbiology</jtitle><addtitle>Food Microbiol</addtitle><date>2017-04</date><risdate>2017</risdate><volume>62</volume><spage>9</spage><epage>14</epage><pages>9-14</pages><issn>0740-0020</issn><eissn>1095-9998</eissn><abstract>β-carbolines (βCs) are alkaloids widely distributed in nature that have demonstrated antimicrobial properties. Here, we tested in vitro six βCs against Penicillium digitatum and Botrytis cinerea, causal agents of postharvest diseases on fruit and vegetables. Full aromatic βCs (harmine, harmol, norharmane and harmane) exhibited a marked inhibitory effect on conidia germination at concentrations between 0.5 and 1 mM, while dihydro-βCs (harmalina and harmalol) only caused germination delay. Harmol showed the highest inhibitory effect on both fungal pathogens. After 24 h of exposure to 1 mM harmol, conidia revealed a severe cellular damage, exhibiting disorganized cytoplasm and thickened cell wall. Harmol antimicrobial effect was fungicidal on B. cinerea, while it was fungistatic on P. digitatum. Conidia membrane permeabilization was detected in treatments with harmol at sub-inhibitory and inhibitory concentrations, for both pathogens. In addition, residual infectivity of P. digitatum on lemons and B. cinerea on blueberries was significantly reduced after exposure to this alkaloid. It also inhibited mycelial growth, preventing sporulation at the highest concentration tested. These results indicate that harmol might be a promising candidate as a new antifungal molecule to control causal agents of fruit diseases.
•Full aromatic β-carbolines have inhibitory effect on P. digitatum and B. cinerea.•The β-carboline harmol has the highest inhibitory effect.•Harmol causes membrane permeabilization and cellular damage.•Fungi infectivity on fruit is significantly reduced after exposure to harmol.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>27889171</pmid><doi>10.1016/j.fm.2016.09.011</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0001-9584-4369</orcidid><oa>free_for_read</oa></addata></record> |
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subjects | Alkaloids Botrytis - cytology Botrytis - drug effects Botrytis - ultrastructure Botrytis cinerea Carbolines - pharmacology Citrus - microbiology Conidial membrane permeabilization Fruit - microbiology Fungicides, Industrial - pharmacology Germination - drug effects Germination inhibition Harmine - analogs & derivatives Harmine - pharmacology Harmol Infectivity Microbial Sensitivity Tests Mycelium - drug effects Penicillium - cytology Penicillium - drug effects Penicillium - ultrastructure Penicillium digitatum Phytopathogens Spores, Fungal - drug effects Spores, Fungal - physiology Vaccinium |
title | Antifungal activity of β-carbolines on Penicillium digitatum and Botrytis cinerea |
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