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1.
Bioorg Med Chem Lett ; 18(20): 5614-7, 2008 Oct 15.
Artigo em Inglês | MEDLINE | ID: mdl-18793855

RESUMO

We synthesized all of the monomethoxycoumarins, 5-alkoxycoumarins and their derivatives, and investigated their nematicidal activity against the phytopathogenic nematode, Bursaphelenchus xylophilus. Among the compounds, 5-ethoxycoumarin showed the highest nematicidal activity. Furthermore, 5-ethoxycoumarin was comparatively harmless against both the brine shrimps, Artemia salina, and the Japanese killifish, Oryzias latipes.


Assuntos
Antinematódeos/síntese química , Química Farmacêutica/métodos , Animais , Antinematódeos/farmacologia , Artemia , Bioensaio , Cumarínicos/química , Cumarínicos/farmacologia , Desenho de Fármacos , Hidrólise , Modelos Químicos , Nematoides , Oryzias , Relação Estrutura-Atividade
2.
Z Naturforsch C J Biosci ; 63(1-2): 59-65, 2008.
Artigo em Inglês | MEDLINE | ID: mdl-18386489

RESUMO

Under the bioassay-guided method, two diterpenes, 3-O-(2",3"-dimethylbutanoyl)-13-O-dodecanoylingenol (1) and 3-O-(2",3"-dimethylbutanoyl)-13-O-decanoylingenol (2) isolated from Euphorbia kansui, showed a pronounced antinematodal activity against the nematode Bursaphelenchus xylophilus at the same minimum effective dose (MED) of 5 microg per cotton ball and still displayed antinematodal activity at a dose of 2.5 microg per cotton ball. Compounds 3-6 were obtained, and the structure of the new compound 6 was elucidated based on 1D- and 2D-NMR analyses and physicochemical data. Preliminary structure-biological activity relationships of ingenane-type compounds were deduced.


Assuntos
Antinematódeos/toxicidade , Diterpenos/toxicidade , Euphorbia/química , Nematoides/efeitos dos fármacos , Raízes de Plantas/química , Madeira/parasitologia , Animais , Diterpenos/isolamento & purificação , Modelos Moleculares , Pinus/parasitologia
3.
Biosci Biotechnol Biochem ; 71(4): 1086-9, 2007 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-17420578

RESUMO

Three compounds, 20-O-acetyl-[3-O-(2'E,4'Z)-decadienoyl]-ingenol (1), 20-O-acetyl-[5-O-(2'E,4'Z)-decadienoyl]-ingenol (2) and 3-O-(2'E,4'Z)-decadienoylingenol (3), were isolated from Euphorbia kansui under the bioassay-guided method. Each compound showed the same antinematodal activity against the nematode, Bursaphelenchus xylophilus, at a minimum effective dose (MED) of 5 microg/cotton ball.


Assuntos
Antinematódeos/isolamento & purificação , Antinematódeos/farmacologia , Diterpenos/isolamento & purificação , Diterpenos/farmacologia , Euphorbia/química , Cromatografia em Camada Fina , Diterpenos/síntese química , Indicadores e Reagentes , Espectroscopia de Ressonância Magnética , Modelos Moleculares , Raízes de Plantas/química , Espectrometria de Massas por Ionização por Electrospray , Espectrometria de Massas de Bombardeamento Rápido de Átomos , Espectrofotometria Infravermelho , Espectrofotometria Ultravioleta
4.
Biosci Biotechnol Biochem ; 68(11): 2398-400, 2004 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-15564683

RESUMO

Several 3-alkylphenols including 3-undecylphenol, which was isolated from a Sumatran rainforest plant, were synthesized to investigate their antinematodal activity against the phytopathogenic nematodes, Bursapherencus xylophilus. A three-step synthesis involving the treatment of 2-cyclohexen-1-one with the Grignard reagent, oxidation of the resulting 1-alkyl-2-cyclohexen-1-ol and subsequent aromatization of 3-alkyl-2-cyclohexen-1-one successfully afforded such phenols. Among the 3-alkylphenols, 3-nonylphenol showed the highest activity, while 3-decylphenol and 3-undecylphenol also showed high activity.


Assuntos
Antinematódeos/farmacologia , Fenóis/síntese química , Fenóis/farmacologia , Animais , Antinematódeos/síntese química , Relação Dose-Resposta a Droga , Indicadores e Reagentes , Espectroscopia de Ressonância Magnética , Nematoides , Espectrometria de Massas por Ionização por Electrospray , Relação Estrutura-Atividade
5.
Pest Manag Sci ; 60(1): 42-8, 2004 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-14727740

RESUMO

In an earlier paper the authors reported the creation of a novel emamectin benzoate 40 g litre(-1) liquid formulation (Shot Wan Liquid Formulation). The injection of this formulation exerted a preventative effect against the pine wilt disease caused by the pine wood nematode, Bursaphelenchus xylophilus (Steiner & Buhrer) Nickle, and this effect lasted for at least 3 years. The present study was carried out to show experimentally that the marked effect of this formulation was due to the presence and persistence in pine tissues of sufficient amounts of emamectin benzoate to inhibit nematode propagation. A cleanup procedure prior to quantitative analysis of emamectin benzoate by fluorescence HPLC was devised. The presence of the compound in concentrations sufficient to inhibit nematode propagation in the shoots of current growth and its persistence for 3 years explained the marked preventative effect. Non-distribution of emamectin benzoate in some parts of the lower trunk suggested that the formulation should be injected at several points for large trees in order to distribute the compound uniformly to lower branches.


Assuntos
Antinematódeos/metabolismo , Ivermectina/análogos & derivados , Ivermectina/metabolismo , Nematoides/efeitos dos fármacos , Resíduos de Praguicidas/metabolismo , Pinus/metabolismo , Animais , Antinematódeos/isolamento & purificação , Antinematódeos/toxicidade , Transporte Biológico/efeitos dos fármacos , Botrytis/crescimento & desenvolvimento , Cromatografia Líquida de Alta Pressão , Ivermectina/isolamento & purificação , Ivermectina/toxicidade , Nematoides/crescimento & desenvolvimento , Pinus/crescimento & desenvolvimento , Pinus/parasitologia , Brotos de Planta/crescimento & desenvolvimento , Brotos de Planta/metabolismo , Brotos de Planta/parasitologia , Fatores de Tempo
6.
Pest Manag Sci ; 59(3): 365-70, 2003 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-12639056

RESUMO

Injection of the poorly water-soluble emamectin benzoate (EB) into pine trunks required the development of an efficient liquid formulation. For injection into big trees in forests a good rate of injection and a high active content were required. Tests on the viscosity and EB-solubilizing ability of 14 various solubilizers in diethylene glycol monobutyl ether (DGMBE) led to the selection of Sorpol SM-100PM as the solubilizer of the formulation. Relationships between the solubilizing ability and amounts of Sorpol SM-100PM and DGMBE relative to that of EB, and between the concentration of the latter and the viscosity or the injection rate of the formulation led to a novel 40 g litre(-1) emamectin benzoate formulation (Shot Wan Liquid Formulation), which was composed of EB (40), Sorpol SM-100PM (120), DGMBE (160) and distilled water (50 g litre(-1)) in methanol. Injection of this formulation at a dose of 10 g EB per unit volume of pine tree prevented over 90% of the trees from wilting caused by pine wood nematode, and this preventative effect continued for 3 years. Neither discolouration of the leaves nor injury around the injection hole on the trees was observed after injection of the formulation.


Assuntos
Ivermectina/análogos & derivados , Ivermectina/administração & dosagem , Ivermectina/farmacologia , Pinus/parasitologia , Doenças das Plantas/parasitologia , Animais , Relação Dose-Resposta a Droga , Ivermectina/química , Ivermectina/toxicidade , Estrutura Molecular , Nematoides/efeitos dos fármacos , Pinus/efeitos dos fármacos
7.
Z Naturforsch C J Biosci ; 57(3-4): 291-5, 2002.
Artigo em Inglês | MEDLINE | ID: mdl-12064729

RESUMO

Two new garcinia acid derivatives, 2-(butoxycarbonylmethyl)-3-butoxycarbonyl-2-hydroxy-3-propanolide and 1',1"-dibutyl methyl hydroxycitrate, were isolated from the fruits of Garcinia atroviridis guided by TLC bioautography against the fungus Cladosporium herbarum. The structures of these compounds were established by spectral analysis. The former compound represents a unique beta-lactone structure and the latter compound is most likely an artefact of garcinia acid (= hydroxycitric acid). Both compounds showed selective antifungal activity comparable to that of cycloheximide (MID: 0.5 microg/spot) only against C herbarum at the MIDs of 0.4 and 0.8 microg/spot but were inactive against bacteria (Bacillus subtilis, methicillin-resistant Staphylococcus aureus, Pseudomonas aeruginosa and Escherichia coli), other fungi (Alternaria sp., Fusarium moniliforme and Aspergillus ochraceous) including the yeast Candida albicans.


Assuntos
Antifúngicos/química , Citratos/química , Fungos/efeitos dos fármacos , Lactonas/química , Rosaceae/química , Antifúngicos/isolamento & purificação , Antifúngicos/farmacologia , Citratos/isolamento & purificação , Citratos/farmacologia , Cladosporium/efeitos dos fármacos , Cicloeximida/farmacologia , Lactonas/isolamento & purificação , Lactonas/farmacologia , Testes de Sensibilidade Microbiana , Estrutura Molecular , Sementes/química
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