Antifungal Activity of Resveratrol against Botrytis cinerea Is Improved Using 2-Furyl Derivatives
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{"title"=>"Antifungal activity of resveratrol against botrytis cinerea is improved using 2-furyl derivatives", "type"=>"journal", "authors"=>[{"first_name"=>"Francesco", "last_name"=>"Caruso", "scopus_author_id"=>"56977144600"}, {"first_name"=>"Leonora", "last_name"=>"Mendoza", "scopus_author_id"=>"7006043068"}, {"first_name"=>"Paulo", "last_name"=>"Castro", "scopus_author_id"=>"38660891800"}, {"first_name"=>"Milena", "last_name"=>"Cotoras", "scopus_author_id"=>"6505871225"}, {"first_name"=>"Maria", "last_name"=>"Aguirre", "scopus_author_id"=>"16534552600"}, {"first_name"=>"Betty", "last_name"=>"Matsuhiro", "scopus_author_id"=>"6701311931"}, {"first_name"=>"Mauricio", "last_name"=>"Isaacs", "scopus_author_id"=>"7103363276"}, {"first_name"=>"Miriam", "last_name"=>"Rossi", "scopus_author_id"=>"7403708958"}, {"first_name"=>"Angela", "last_name"=>"Viglianti", "scopus_author_id"=>"35084477200"}, {"first_name"=>"Roberto", "last_name"=>"Antonioletti", "scopus_author_id"=>"6701829130"}], "year"=>2011, "source"=>"PLoS ONE", "identifiers"=>{"issn"=>"19326203", "scopus"=>"2-s2.0-80053991873", "pui"=>"362734516", "doi"=>"10.1371/journal.pone.0025421", "isbn"=>"1932-6203", "sgr"=>"80053991873", "pmid"=>"22022392"}, "id"=>"0b73547f-9711-3b58-aa07-9cd5fe87581a", "abstract"=>"The antifungal effect of three furyl compounds closely related to resveratrol, (E)-3,4,5-trimethoxy-β-(2-furyl)-styrene (1), (E)-4-methoxy-β-(2-furyl)-styrene (2) and (E)-3,5-dimethoxy-β-(2-furyl)-styrene (3) against Botrytis cinerea was analyzed. The inhibitory effect, at 100 µg ml−1 of compounds 1, 2, 3 and resveratrol on conidia germination, was determined to be about 70%, while at the same concentration pterostilbene (a dimethoxyl derivative of resveratrol) produced complete inhibition. The title compounds were more fungitoxic towards in vitro mycelial growth than resveratrol and pterostilbene. Compound 3 was the most active and a potential explanation of this feature is given using density functional theory (DFT) calculations on the demethoxylation/demethylation process. Compound 3 was further evaluated for its effects on laccase production, oxygen consumption and membrane integrity of B. cinerea. An increase of the laccase activity was observed in the presence of compound 3 and, using Sytox Green nucleic acid stain, it was demonstrated that this compound altered B. cinerea membrane. Finally, compound 3 partially affected conidia respiration.", "link"=>"http://www.mendeley.com/research/antifungal-activity-resveratrol-against-botrytis-cinerea-improved-using-2furyl-derivatives", "reader_count"=>50, "reader_count_by_academic_status"=>{"Unspecified"=>3, "Student > Doctoral Student"=>5, "Researcher"=>10, "Student > Ph. D. Student"=>7, "Student > Postgraduate"=>1, "Student > Master"=>6, "Other"=>4, "Student > Bachelor"=>8, "Lecturer"=>2, "Professor"=>4}, "reader_count_by_user_role"=>{"Unspecified"=>3, "Student > Doctoral Student"=>5, "Researcher"=>10, "Student > Ph. D. Student"=>7, "Student > Postgraduate"=>1, "Student > Master"=>6, "Other"=>4, "Student > Bachelor"=>8, "Lecturer"=>2, "Professor"=>4}, "reader_count_by_subject_area"=>{"Unspecified"=>6, "Engineering"=>2, "Biochemistry, Genetics and Molecular Biology"=>4, "Materials Science"=>2, "Agricultural and Biological Sciences"=>18, "Medicine and Dentistry"=>2, "Physics and Astronomy"=>1, "Chemical Engineering"=>1, "Chemistry"=>13, "Immunology and Microbiology"=>1}, "reader_count_by_subdiscipline"=>{"Engineering"=>{"Engineering"=>2}, "Materials Science"=>{"Materials Science"=>2}, "Medicine and Dentistry"=>{"Medicine and Dentistry"=>2}, "Chemistry"=>{"Chemistry"=>13}, "Physics and Astronomy"=>{"Physics and Astronomy"=>1}, "Immunology and Microbiology"=>{"Immunology and Microbiology"=>1}, "Agricultural and Biological Sciences"=>{"Agricultural and Biological Sciences"=>18}, "Biochemistry, Genetics and Molecular Biology"=>{"Biochemistry, Genetics and Molecular Biology"=>4}, "Unspecified"=>{"Unspecified"=>6}, "Chemical Engineering"=>{"Chemical Engineering"=>1}}, "reader_count_by_country"=>{"United Kingdom"=>1, "Spain"=>1}, "group_count"=>1}

Scopus | Further Information

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Figshare

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  • {"files"=>["https://ndownloader.figshare.com/files/726229"], "description"=>"a<p>Estimated lipophilicity values and sigma, calculated using Advanced Chemistry Development (ACD/Labs) Software V9.04 (1994–2010 ACD/Labs), as stored in SciFinder.</p>b<p>Determination of median effective doses (ED<sub>50</sub>), based on colony diameter measurements after 96 h of incubation.</p>", "links"=>[], "tags"=>["compounds", "mycelial"], "article_id"=>396582, "categories"=>["Chemistry"], "users"=>["Francesco Caruso", "Leonora Mendoza", "Paulo Castro", "Milena Cotoras", "Maria Aguirre", "Betty Matsuhiro", "Mauricio Isaacs", "Miriam Rossi", "Angela Viglianti", "Roberto Antonioletti"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0025421.t001", "stats"=>{"downloads"=>1, "page_views"=>2, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Effect_of_compounds_on_in_vitro_mycelial_growth_of_B_cinerea_/396582", "title"=>"Effect of compounds on <i>in vitro</i> mycelial growth of <i>B. cinerea</i>.", "pos_in_sequence"=>0, "defined_type"=>3, "published_date"=>"2011-10-11 01:49:42"}
  • {"files"=>["https://ndownloader.figshare.com/files/725626"], "description"=>"<p><b>1</b>: (E)-3,4,5-trimethoxy-β-(2-furyl)-styrene, <b>2</b>: (E)-4-methoxy-β-(2-furyl)-styrene, <b>3</b>: (E)-3,5-dimethoxy-β-(2-furyl)-styrene. Resveratrol and pterostilbene were utilized as control.</p>", "links"=>[], "tags"=>["chemistry"], "article_id"=>395976, "categories"=>["Chemistry"], "users"=>["Francesco Caruso", "Leonora Mendoza", "Paulo Castro", "Milena Cotoras", "Maria Aguirre", "Betty Matsuhiro", "Mauricio Isaacs", "Miriam Rossi", "Angela Viglianti", "Roberto Antonioletti"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0025421.g001", "stats"=>{"downloads"=>1, "page_views"=>6, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Compounds_used_in_this_study_/395976", "title"=>"Compounds used in this study.", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2011-10-11 01:39:36"}
  • {"files"=>["https://ndownloader.figshare.com/files/725763"], "description"=>"<p>From left to right: Resveratrol, pterostilbene, compound <b>1</b>, compound <b>2</b> and compound <b>3</b>, see also “<a href=\"http://www.plosone.org/article/info:doi/10.1371/journal.pone.0025421#s3\" target=\"_blank\">Materials and methods</a> section k Procedure information about figures”. Different letters indicate that the means are significantly different at P<0.05.</p>", "links"=>[], "tags"=>["compounds", "conidial", "germination"], "article_id"=>396110, "categories"=>["Chemistry"], "users"=>["Francesco Caruso", "Leonora Mendoza", "Paulo Castro", "Milena Cotoras", "Maria Aguirre", "Betty Matsuhiro", "Mauricio Isaacs", "Miriam Rossi", "Angela Viglianti", "Roberto Antonioletti"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0025421.g002", "stats"=>{"downloads"=>2, "page_views"=>9, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Effect_of_the_compounds_on_conidial_germination_of_B_cinerea_/396110", "title"=>"Effect of the compounds on conidial germination of <i>B. cinerea</i>.", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2011-10-11 01:41:50"}
  • {"files"=>["https://ndownloader.figshare.com/files/725845"], "description"=>"<p>Compound <b>1</b>, top left, and its demethoxylated derivative (E)-4,5-dimethoxy,3-hydroxy-β-(2-furyl)-styrene, top right. Compound <b>3</b>, 2<sup>nd</sup> group from top, left, and its demethoxylated derivative (E)-3-hydroxy-5-methoxy,β-(2-furyl)-styrene, 2<sup>nd</sup> group from top, right. Compound <b>2</b>, 3<sup>rd</sup> group from top, left, and its demethoxylated derivative (E)-4-hydroxy,β-(2-furyl)-styrene, 3<sup>rd</sup> group from top, right. Geometry optimized molecular structure of piceatannol, bottom; some atomic separations are also included.</p>", "links"=>[], "tags"=>["chemistry"], "article_id"=>396200, "categories"=>["Chemistry"], "users"=>["Francesco Caruso", "Leonora Mendoza", "Paulo Castro", "Milena Cotoras", "Maria Aguirre", "Betty Matsuhiro", "Mauricio Isaacs", "Miriam Rossi", "Angela Viglianti", "Roberto Antonioletti"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0025421.g003", "stats"=>{"downloads"=>0, "page_views"=>0, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Selected_population_charge_distribution_/396200", "title"=>"Selected population charge distribution.", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2011-10-11 01:43:20"}
  • {"files"=>["https://ndownloader.figshare.com/files/726183"], "description"=>"<p>Effect of compound 3 on oxygen consumption by <i>B. cinerea</i> conidia.</p>", "links"=>[], "tags"=>["chemistry"], "article_id"=>396531, "categories"=>["Chemistry"], "users"=>["Francesco Caruso", "Leonora Mendoza", "Paulo Castro", "Milena Cotoras", "Maria Aguirre", "Betty Matsuhiro", "Mauricio Isaacs", "Miriam Rossi", "Angela Viglianti", "Roberto Antonioletti"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0025421.g006", "stats"=>{"downloads"=>1, "page_views"=>7, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Effect_of_compound_3_on_oxygen_consumption_by_B_cinerea_conidia_/396531", "title"=>"Effect of compound 3 on oxygen consumption by <i>B. cinerea</i> conidia.", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2011-10-11 01:48:51"}
  • {"files"=>["https://ndownloader.figshare.com/files/366876", "https://ndownloader.figshare.com/files/366914", "https://ndownloader.figshare.com/files/366939", "https://ndownloader.figshare.com/files/366966", "https://ndownloader.figshare.com/files/366991", "https://ndownloader.figshare.com/files/367023", "https://ndownloader.figshare.com/files/367052"], "description"=>"<div><p>The antifungal effect of three furyl compounds closely related to resveratrol, (E)-3,4,5-trimethoxy-β-(2-furyl)-styrene (<b>1</b>), (E)-4-methoxy-β-(2-furyl)-styrene (<b>2</b>) and (E)-3,5-dimethoxy-β-(2-furyl)-styrene (<b>3</b>) against <em>Botrytis cinerea</em> was analyzed. The inhibitory effect, at 100 µg ml<sup>−1</sup> of compounds <b>1</b>, <b>2</b>, <b>3</b> and resveratrol on conidia germination, was determined to be about 70%, while at the same concentration pterostilbene (a dimethoxyl derivative of resveratrol) produced complete inhibition. The title compounds were more fungitoxic towards <em>in vitro</em> mycelial growth than resveratrol and pterostilbene. Compound <b>3</b> was the most active and a potential explanation of this feature is given using density functional theory (DFT) calculations on the demethoxylation/demethylation process. Compound <b>3</b> was further evaluated for its effects on laccase production, oxygen consumption and membrane integrity of <em>B. cinerea</em>. An increase of the laccase activity was observed in the presence of compound <b>3</b> and, using Sytox Green nucleic acid stain, it was demonstrated that this compound altered <em>B. cinerea</em> membrane. Finally, compound <b>3</b> partially affected conidia respiration.</p> </div>", "links"=>[], "tags"=>["antifungal", "resveratrol", "2-furyl", "derivatives"], "article_id"=>132506, "categories"=>["Chemistry"], "users"=>["Francesco Caruso", "Leonora Mendoza", "Paulo Castro", "Milena Cotoras", "Maria Aguirre", "Betty Matsuhiro", "Mauricio Isaacs", "Miriam Rossi", "Angela Viglianti", "Roberto Antonioletti"], "doi"=>["https://dx.doi.org/10.1371/journal.pone.0025421.s001", "https://dx.doi.org/10.1371/journal.pone.0025421.s002", "https://dx.doi.org/10.1371/journal.pone.0025421.s003", "https://dx.doi.org/10.1371/journal.pone.0025421.s004", "https://dx.doi.org/10.1371/journal.pone.0025421.s005", "https://dx.doi.org/10.1371/journal.pone.0025421.s006", "https://dx.doi.org/10.1371/journal.pone.0025421.s007"], "stats"=>{"downloads"=>7, "page_views"=>12, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/Antifungal_Activity_of_Resveratrol_against_Botrytis_cinerea_Is_Improved_Using_2_Furyl_Derivatives/132506", "title"=>"Antifungal Activity of Resveratrol against <em>Botrytis cinerea</em> Is Improved Using 2-Furyl Derivatives", "pos_in_sequence"=>0, "defined_type"=>4, "published_date"=>"2011-10-11 00:41:46"}
  • {"files"=>["https://ndownloader.figshare.com/files/725963"], "description"=>"<p>Kinetics of laccase activity in absence (□) or presence (▴) of 100 ug ml<sup>−1</sup> of compound <b>3</b>, (<b>A</b>). Specific activity of laccase produced by <i>B. cinerea</i> after six days of incubation, (<b>B</b>). Different letters indicate that the means are significantly different at P<0.05.</p>", "links"=>[], "tags"=>["laccase"], "article_id"=>396314, "categories"=>["Chemistry"], "users"=>["Francesco Caruso", "Leonora Mendoza", "Paulo Castro", "Milena Cotoras", "Maria Aguirre", "Betty Matsuhiro", "Mauricio Isaacs", "Miriam Rossi", "Angela Viglianti", "Roberto Antonioletti"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0025421.g004", "stats"=>{"downloads"=>0, "page_views"=>2, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Effect_of_compound_3_on_laccase_production_by_B_cinerea_/396314", "title"=>"Effect of compound 3 on laccase production by <i>B. cinerea</i>.", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2011-10-11 01:45:14"}

PMC Usage Stats | Further Information

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Relative Metric

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