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1.
FEMS Microbiol Ecol ; 94(4)2018 04 01.
Artigo em Inglês | MEDLINE | ID: mdl-29528408

RESUMO

Phytophthora infestans is a devastating pathogen of tomato and potato. It readily overcomes resistance genes and applied agrochemicals and hence even today causes large yield losses. Fungal endophytes provide a largely unexplored avenue of control of Phy. infestans. Not only do endophytes produce a wide array of bioactive metabolites, they may also directly compete with and defeat pathogens in planta. Here, we tested 12 fungal endophytes isolated from different plant species in vitro for their production of metabolites with anti- Phytophthora activity. Four well-performing isolates were evaluated for their ability to suppress nine isolates of Phy. infestans on agar medium and in planta. Two endophytes reliably inhibited all Phy. infestans isolates on agar medium, of which Phoma eupatorii isolate 8082 was the most promising. It nearly abolished infection by Phy. infestans in planta. Our data indicate a role for the production of anti-Phytophthora compounds by the fungus and/or an enhanced plant defense response, as evident by an enhanced anthocyanin production. Here, we present a potential biocontrol agent, which can inhibit a broad-spectrum of Phy. infestans isolates. Such broadly acting inhibition is ideal, because it allows for effective control of genetically diverse isolates and may slow the adaptation of Phy. infestans.


Assuntos
Antibiose/fisiologia , Agentes de Controle Biológico/metabolismo , Fungos/metabolismo , Phytophthora infestans/metabolismo , Doenças das Plantas/parasitologia , Doenças das Plantas/terapia , Solanum lycopersicum/parasitologia , Solanum tuberosum/parasitologia , Endófitos/metabolismo , Solanum lycopersicum/microbiologia , Solanum tuberosum/microbiologia
2.
Nat Prod Commun ; 7(3): 293-4, 2012 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-22545398

RESUMO

Two new acaranoic acids, named seimatoporic acid A and B (1, and 2), together with six known compounds, R-(-)-mellein (3), cis-4-hydroxymellein (4), trans-4-hydroxymellein (5), 4R-hydroxy-5-methylmellein (6), (-)-5-hydroxymethylmellein (7), and ergosterol (8) were isolated from an endophytic fungus, Seimatosporium sp, by a bioassay-guided procedure. The structures of the new compounds have been assigned from analysis of the 1H and 13C NMR spectra, DEPT, and by 2D COSY, HMQC, HMBC and NOESY experiments. A mixture of compounds 1 and 2 showed strong antifungal activity against Botrytis cinerea, Septoria tritici, and Pyricularia oryzae.


Assuntos
Anti-Infecciosos/isolamento & purificação , Isocumarinas/química , Isocumarinas/isolamento & purificação , Xylariales/química , Endófitos/química , Endófitos/metabolismo , Epilobium/microbiologia , Testes de Sensibilidade Microbiana , Xylariales/metabolismo
3.
Fitoterapia ; 83(3): 523-6, 2012 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-22233864

RESUMO

Four new pyrenocines, named pyrenocines J-M (1-4), were isolated from an endophytic fungus, Phomopsis sp, by a bioassay-guided method. The structures of the new compound have been assigned from ¹H and ¹³C NMR spectra, DEPT, and by 2D COSY, HMQC, and HMBC experiments. Preliminary studied showed that compounds 1, 2 and 4 showed good antifungal, antibacterial, and algicidal properties, while compound 3 had good antibacterial and algicidal properties.


Assuntos
Acroleína/farmacologia , Anti-Infecciosos/farmacologia , Ascomicetos/química , Produtos Biológicos/farmacologia , Pironas/farmacologia , Acroleína/análogos & derivados , Acroleína/química , Acroleína/isolamento & purificação , Anti-Infecciosos/química , Anti-Infecciosos/isolamento & purificação , Produtos Biológicos/química , Endófitos/química , Estrutura Molecular , Pironas/química , Pironas/isolamento & purificação
4.
Nat Prod Commun ; 6(6): 841-3, 2011 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-21815422

RESUMO

The five-step synthesis of the new 4H-anthra[1,2-b]pyran derivative 1 is reported. The key steps in this approach included a Marschalk alkylation of 1,4-dihydroxyanthraquinone followed by a Baker-Venkataraman reaction and then an acid-catalyzed cyclization of ring A to form the 4H-anthra[1,2-b]pyran system. Two compounds, the 4H-anthra[1,2-b]pyran 1 and the anthraquinone derivative 6 were evaluated for antimicrobial activity and showed moderate antialgal, antifungal, and antibacterial activities.


Assuntos
Antibacterianos/síntese química , Antibacterianos/farmacologia , Piranos/síntese química , Piranos/farmacologia , Estrutura Molecular
5.
Nat Prod Commun ; 6(5): 661-6, 2011 May.
Artigo em Inglês | MEDLINE | ID: mdl-21615028

RESUMO

Two new benzyl gamma-butyrolactone analogues, (R)-5-((S)-hydroxy(phenyl)-methyl)dihydrofuran-2(3H)-one (1) and its 6-acetate (2), and a new naphthalenone derivative (8), together with eight additional known aromatic derivatives, (S)-5-((S)-hydroxy(phenyl)-methyl)dihydrofuran-2(3H)-one (3), (S)-5-benzyl-dihydrofuran-2(3H)-one (4), 5-phenyl-4-oxopentanoic acid (5), gamma-oxo-benzenepentanoic acid methyl ester (6), 3-(2,5-dihydro-4-hydroxy-5-oxo-3-phenyl-2-furyl)propionic acid (7), (3R)-5-methylmellein (9), integracins A (10) and B (11) were isolated from Cytospora sp., an endophytic fungus isolated from Ilex canariensis from Gomera. The structures of these compounds were elucidated by detailed spectroscopic analysis, comparison with reported data, and chemical interconversion. The absolute configurations of the new compounds (1, 2, 8) were established on the basis of optical rotation or CD spectra analysis. Preliminary studies showed antimicrobial activity of these compounds against the fungi Microbotryum violaceum, Botrytis cinerea and Septoria tritici, the alga Chlorella fusca, and the bacterium Bacillus megaterium.


Assuntos
Anti-Infecciosos/análise , Ascomicetos/química , Furanos/isolamento & purificação , Furanos/química , Ilex/microbiologia , Testes de Sensibilidade Microbiana , Estrutura Molecular
6.
Nat Prod Commun ; 6(11): 1595-6, 2011 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-22224269

RESUMO

Several biologically active alkaloids (1-4, 6), including a new quinazoline-6-carboxylic acid (1), were isolated from the medicinal plant Zanthoxylum rhetsa, an evergreen tree, native to subtropical areas. Whereas the pharmacological properties of the plant extract and single constituents have been widely tested, we now show that all of the metabolites have antialgal activities, all but 6 are antibacterial, and 6 and the reduction product 5 (derived from 4) are also antifungal.


Assuntos
Alcaloides/isolamento & purificação , Antibacterianos/isolamento & purificação , Antifúngicos/isolamento & purificação , Quinazolinas/isolamento & purificação , Zanthoxylum/química , Alcaloides/química , Antibacterianos/química , Antifúngicos/química , Testes de Sensibilidade Microbiana , Estrutura Molecular , Quinazolinas/química
7.
Nat Prod Commun ; 6(12): 1905-6, 2011 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-22312735

RESUMO

Phomosine K (1), a new phomosine derivative, has been isolated from Phomopsis sp., in addition to six known compounds: phomosine A (2), phenylalanine amide (3), 2-hydroxymethyl-4beta,5alpha,6beta-trihydroxycyclohex-2-en (4), (-)-phyllostine (5), (+)-epiepoxydon (6), and (+)-epoxydon monoacetate (7). Preliminary studies showed that compound 1 had strong antibacterial activity, while compounds 4-7 showed good antifungal, antibacterial, and algicidal properties, except compounds 4 and 6, which lacked antifungal activity.


Assuntos
Anti-Infecciosos/isolamento & purificação , Ascomicetos/metabolismo , Anti-Infecciosos/química , Anti-Infecciosos/farmacologia
8.
Nat Prod Commun ; 6(12): 1907-12, 2011 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-22312736

RESUMO

From the endophytic fungus Phomosis sp., four known phomosines A-D (1-4) and three new phomosines H-J (5-7) have been isolated. The structures of the new compounds were determined on the basis of their spectroscopic data analysis (1H, 13C, 1H-1H COSY, HMQC, and HMBC NMR, as well as mass spectrometry). The structures of phomosine H (5) and J (7) were also confirmed by semisynthesis from phomosine A (1). The remaining four known compounds [phomosines A-D (1-4)] were identified by comparing their spectroscopic data with those reported in the literature. The four known metabolites were biologically active. Of the novel metabolites, only 6 was antifungal and antibacterial.


Assuntos
Anti-Infecciosos/isolamento & purificação , Ascomicetos/metabolismo , Éteres/isolamento & purificação , Ligustrum/microbiologia , Anti-Infecciosos/farmacologia , Éteres/química , Éteres/farmacologia
9.
Nat Prod Commun ; 5(8): 1175-80, 2010 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-20839612

RESUMO

A new metabolite, 3,16-diketoaphidicolan (1), was isolated together with four known compounds: aphidicolin (2), 17-acetyl-aphidicolin (3), (+)-eupenoxide (4), and phomoxanthone A (5) from the endophytic fungus Phoma sp. The structure of the new compound 1 was determined by spectroscopic methods (mainly extensive 1D and 2D NMR experiments and by mass spectral measurements) and confirmed by X-ray crystallography. Its absolute configuration was assigned by means of the solid-state CD/TDDFT approach comparing the solid-state CD spectrum with the TDDFT-calculated one on the X-ray geometry.


Assuntos
Afidicolina/análogos & derivados , Ascomicetos/metabolismo , Plantas/microbiologia , Afidicolina/química , Dicroísmo Circular , Cristalografia por Raios X , Espectroscopia de Ressonância Magnética
10.
Nat Prod Commun ; 5(4): 559-61, 2010 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-20433072

RESUMO

Eight compounds were isolated from the stem bark of the plant Afraegle paniculata. One of them, a dimethyl ether of S-trans-marmin (1), is reported as a new natural product. The structures were determined by comprehensive analyses of their 1D and 2D NMR spectroscopic and HREIMS data. The remaining seven known compounds, identified by comparing their spectroscopic data with those reported in the literature, were S-trans-marmin (2), psoralene (3), bergaptene (4), imperatorin (5), 2-(4-hydroxy-3,5-dimethoxyphenyl)-3-hydroxymethyl-2,3-dihydro- 1,4,5-trioxaphenanthren-6-one (6), xanthoxyletin (7), and beta-sitosterol glucopyranoside. Preliminary studies indicated that compounds 2, 3, 5, and 7 showed potent antibacterial, fungicidal, and algicidal properties, while 6 showed only moderate algicidal property.


Assuntos
Antibacterianos/isolamento & purificação , Antifúngicos/isolamento & purificação , Cumarínicos/isolamento & purificação , Rutaceae/química , Antibacterianos/química , Antibacterianos/farmacologia , Antifúngicos/química , Antifúngicos/farmacologia , Cumarínicos/química , Cumarínicos/farmacologia , Espectrometria de Massas , Testes de Sensibilidade Microbiana , Ressonância Magnética Nuclear Biomolecular , Casca de Planta/química
11.
Planta Med ; 76(6): 620-5, 2010 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-19937550

RESUMO

Four new iridoids viz., plumeridoids A, B, and C and epiplumeridoid C were isolated from the stem bark of Plumeria rubra Linn. together with twenty-four known compounds viz., 1-( P-hydroxyphenyl)propan-1-one, isoplumericin, plumericin, dihydroplumericin, allamcin, fulvoplumerin, allamandin, plumieride, P- E-coumaric acid, 2,6-dimethoxy- P-benzoquinone, scopoletin, cycloart-25-en-3 beta,24-diol, 2,4,6-trimethoxyaniline, ajunolic acid, ursolic acid, oleanolic acid, beta-amyrin acetate, betulinic acid, lupeol and its acetate, 2,3-dihydroxypropyl octacosanoate, glucoside of beta-sitosterol, and a mixture of common sterols (stigmasterol and beta-sitosterol). Their structures were determined by means of spectroscopic data including HREIMS, 1H NMR, 13C NMR, 2D NMR (HMQC, HMBC, NOESY) and by comparison with published data. All but one of thirteen tested compounds exhibited antifungal, antialgal, and/or antibacterial activities.


Assuntos
Antibacterianos/farmacologia , Apocynaceae/química , Iridoides/farmacologia , Casca de Planta/química , Caules de Planta/química , Antibacterianos/química , Bactérias/efeitos dos fármacos , Iridoides/química , Estrutura Molecular , Casca de Planta/metabolismo , Caules de Planta/metabolismo
12.
Nat Prod Commun ; 4(11): 1449-54, 2009 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-19967971

RESUMO

The new (22E,24R)-3-acetoxy-19(10-->6)-abeo-ergosta-5,7,9,22-tetraen-3beta-ol (1) and the known (22E,24R)-19(10-->6)-abeo-ergosta-5,7,9,22-tetraen-3beta-ol (2), two interesting ergosteroids with rare aromatized ring B, together with seven known derivatives, namely (22E,24R)-ergosta-5,7,22-trien-3beta-ol (3), (22E,24R)-ergosta-4,7,22-trien-3-one (4), (22E,24R)-ergosta-4,6,8(14),22-tetraen-3-one (5), (22E,24R)-5alpha,8alpha-epidioxyergosta-6,22-dien-3beta-ol (6), (22E,24R)-ergosta-7,22-dien-3beta,5alpha,6beta-triol (7), (22E,24R)-6-acetoxy-ergosta-7,22-dien-3beta,5alpha,6beta-triol (8), and (22E,24R)-3,6-diacetoxy-ergosta-7,22-dien-3beta,5alpha,6beta-triol (9), were isolated from Colletotrichum sp., an endophytic fungus isolated from Ilex canariensis from Gomera. The structures of these compounds were elucidated by detailed spectroscopic analysis, comparison with reported data, and chemical interconversion. The isolation of these metabolites not only displays a beautiful array of chemical diversity, but also gives insight into the biosynthetic interconnections. Preliminary studies showed antimicrobial activity of these compounds against the fungus Microbotryum violaceum, the alga Chlorella fusca, and the bacteria Escherichia coli and Bacillus megaterium.


Assuntos
Colletotrichum/química , Esteroides/química , Acetilação , Antibacterianos/biossíntese , Antibacterianos/química , Antibacterianos/farmacologia , Bactérias/efeitos dos fármacos , Cromatografia em Camada Fina , Meios de Cultura , Eucariotos/efeitos dos fármacos , Fungos/efeitos dos fármacos , Ilex/microbiologia , Espectroscopia de Ressonância Magnética , Testes de Sensibilidade Microbiana , Esteroides/biossíntese , Esteroides/farmacologia
13.
Planta Med ; 74(1): 50-4, 2008 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-18203062

RESUMO

Two new natural dihydrochalcones exhibiting antimicrobial properties together with six known compounds were isolated from the Cameroonian medicinal plant Eriosema glomerata. The structures of the new dihydrochalcones were elucidated as 2',4'-dihydroxy-4-methoxy-3'-( gamma, gamma-dimethylallyl)dihydrochalcone and 2',4'-dihydroxy-3'-( gamma, gamma-dimethylallyl)dihydrochalcone by detailed spectroscopic analysis. The two new dihydrochalcones, named erioschalcones A ( 1) and B ( 2), demonstrated significant inhibitory activity against the microbial strains Bacillus megaterium, Escherichia coli, Chlorella fusca and Microbotryum violaceum.


Assuntos
Anti-Infecciosos/farmacologia , Fabaceae , Fitoterapia , Extratos Vegetais/farmacologia , Anti-Infecciosos/administração & dosagem , Anti-Infecciosos/uso terapêutico , Chalconas/administração & dosagem , Chalconas/farmacologia , Chalconas/uso terapêutico , Clorófitas/efeitos dos fármacos , Bactérias Gram-Negativas/efeitos dos fármacos , Bactérias Gram-Positivas/efeitos dos fármacos , Humanos , Testes de Sensibilidade Microbiana , Fungos Mitospóricos/efeitos dos fármacos , Extratos Vegetais/administração & dosagem , Extratos Vegetais/uso terapêutico , Prenilação
14.
Chem Pharm Bull (Tokyo) ; 55(11): 1640-2, 2007 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-17978527

RESUMO

Two new prenylated anthraquinones, laurenquinone A (1) and B (2) were isolated from the seeds of Vismia laurentii together with four known compounds; xanthone V(1) (3), physcion (4), 3-geranyloxyemodin anthrone (5) and friedelin (6). The structures of the new metabolites were determined with the help of spectroscopic data including extensive 2D-NMR spectroscopy. The known compounds were identified by comparison of their physical and spectroscopic data with those reported in the literature. Compounds 1, 4 and 5 exhibited moderate algicidal activity against Chlorella fusca and 3 showed moderate activity against the gram-positive bacterium Bacillus megaterium.


Assuntos
Antraquinonas/farmacologia , Anti-Infecciosos/farmacologia , Bacillus megaterium/efeitos dos fármacos , Chlorella/efeitos dos fármacos , Clusiaceae/química , Plantas Medicinais/química , Sementes/química , Antraquinonas/química , Antraquinonas/isolamento & purificação , Anti-Infecciosos/química , Anti-Infecciosos/isolamento & purificação , Bacillus megaterium/crescimento & desenvolvimento , Chlorella/crescimento & desenvolvimento , Espectroscopia de Ressonância Magnética , Testes de Sensibilidade Microbiana , Prenilação
15.
J Nat Prod ; 70(4): 600-3, 2007 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-17352491

RESUMO

Three new prenylated anthranoids, harunmadagascarins C (1) and D (2) and kenganthranol D (3), together with three known compounds (4-6) were isolated from the leaves of Harungana madagascariensis. Their structures were assigned by spectroscopic methods and by comparison with literature data. In the three new natural products 1-3, one or two prenyl groups are incorporated in furan, pyran, or cyclohexane rings in four different modes of annulation. Compounds 2, 4, and 6 were strongly active against the Gram-positive Bacillus megaterium.


Assuntos
Antracenos/isolamento & purificação , Antracenos/farmacologia , Antibacterianos/isolamento & purificação , Antibacterianos/farmacologia , Clusiaceae/química , Plantas Medicinais/química , Antracenos/química , Antibacterianos/química , Bacillus megaterium/efeitos dos fármacos , Camarões , Testes de Sensibilidade Microbiana , Estrutura Molecular , Folhas de Planta/química
16.
Chem Pharm Bull (Tokyo) ; 53(6): 616-9, 2005 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-15930769

RESUMO

Newbouldiaquinone (1), a new naphthoquinone-anthraquinone coupled pigment and a new ceramide named newbouldiamide (2), have been isolated from Newbouldia laevis, besides the known compounds lapachol (3), canthic acid, oleanolic acid, 2-methyl-9,10-anthracenedione, 2-acetylfuro-1,4-naphthoquinone, 2,3-dimethoxy-1,4-benzoquinone, 2-(4-hydroxyphenyl)ethyl triacontanoate, beta-sitosterol and beta-sitosterol glucopyranoside. The structure elucidations of the isolated new compounds were performed on the basis of spectroscopic and chemical evidence. Preliminary studies showed that 1 is moderately antibacterial against Gram-positive Bacillus megaterium and that 3 has moderate herbicidal and antibacterial activities.


Assuntos
Antraquinonas/química , Bignoniaceae , Ceramidas/química , Naftoquinonas/química , Pigmentos Biológicos/química , Antraquinonas/isolamento & purificação , Antraquinonas/farmacologia , Ceramidas/isolamento & purificação , Ceramidas/farmacologia , Testes de Sensibilidade Microbiana/métodos , Naftoquinonas/isolamento & purificação , Naftoquinonas/farmacologia , Pigmentos Biológicos/isolamento & purificação , Pigmentos Biológicos/farmacologia , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/farmacologia , Estruturas Vegetais
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