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1.
J Fungi (Basel) ; 7(12)2021 Dec 15.
Artigo em Inglês | MEDLINE | ID: mdl-34947063

RESUMO

Clovane and isocaryolane derivatives have been proven to show several levels of activity against the phytopathogenic fungus Botrytis cinerea. Both classes of sesquiterpenes are reminiscent of biosynthetic intermediates of botrydial, a virulence factor of B. cinerea. Further development of both classes of antifungal agent requires exploration of the structure-activity relationships for the antifungal effects on B. cinerea and phytotoxic effects on a model crop. In this paper, we report on the preparation of a series of alkoxy-clovane and -isocaryolane derivatives, some of them described here for the first time (2b, 2d, 2f-2h, and 4c-4e); the evaluation of their antifungal properties against B. cinerea, and their phytotoxic activites on the germination of seeds and the growth of radicles and shoots of Lactuca sativa (lettuce). Both classes of compound show a correlation of antifungal activity with the nature of side chains, with the best activity against B. cinerea for 2d, 2h, 4c and 4d. In general terms, while 2-alkoxyclovan-9-ols (2a-2e) exert a general phytotoxic effect, this is not the case for 2-arylalkoxyclovan-9-ols (2f-2i) and 8-alkoxyisocaryolan-9-ols (4a-4d), where stimulating effects would make them suitable candidates for application to plants.

2.
J Nat Prod ; 76(6): 1016-24, 2013 Jun 28.
Artigo em Inglês | MEDLINE | ID: mdl-23730968

RESUMO

Research has been conducted on the biotransformation of (8S,9R)-isocaryolan-9-ol (4a) and (1S,2S,5R,8S)-8-methylene-1,4,4-trimethyltricyclo[6.2.1.0(2,5)]undecan-12-ol (5a) by the fungal phytopathogen Botrytis cinerea. The biotransformation of compound 4a yielded compounds 6-9, while the biotransformation of compound 5a yielded compounds 10-13. The activity of compounds 4a and 5a against B. cinerea has been evaluated. (8R,9R)-Isocaryolane-8,9-diol (6), a major metabolite of compound 4a, shows activity compared to its parent compound 4a, which is inactive. The effect of isocaryolanes 3, 4a, and 5a, together with their biotransformation products 6-8, 10, and 14-17, on the germination and radicle and shoot growth of Lactuca sativa (lettuce) has also been determined. Compounds 7-13 are described for the first time.


Assuntos
Botrytis/metabolismo , Fungicidas Industriais/química , Fungicidas Industriais/farmacologia , Sesquiterpenos/química , Sesquiterpenos/farmacologia , Aldeídos/química , Aldeídos/metabolismo , Biotransformação , Compostos Bicíclicos com Pontes/química , Compostos Bicíclicos com Pontes/metabolismo , Lactuca/crescimento & desenvolvimento , Lactuca/fisiologia , Estrutura Molecular , Estereoisomerismo , Relação Estrutura-Atividade
3.
Rev. Soc. Bras. Med. Trop ; 44(6): 777-780, Nov.-Dec. 2011. tab
Artigo em Inglês | LILACS | ID: lil-611762

RESUMO

INTRODUCTION: Fatty acids are abundant in vegetable oils. They are known to have antibacterial and antifungal properties. METHODS: Antifungal susceptibility was evaluated by broth microdilution assay following CLSI (formerly the NCCLS) guidelines against 16 fungal strains of clinical interest. RESULTS: In this work, fatty acid methyl esters (FAME) was able to inhibit 12 clinical strains of the pathogenic fungus Paracoccidioides brasiliensis and were also active in the bioautographic assay against Cladosporium sphaerospermum. CONCLUSIONS: FAME was a more potent antifungal than trimethoprim-sulfamethoxazole against P. brasiliensis under the experimental conditions tested.


INTRODUÇÃO: Os ácidos graxos são abundantes em óleos vegetais. Eles são conhecidos por suas propriedades antibacterianas e antifúngicas. MÉTODOS: A suscetibilidade a antifúngicos foi avaliada pelo ensaio de microdiluição em caldo de acordo com CLSI (anteriormente NCCLS) sobre 16 isolados de interesse clínico. RESULTADOS: Nesse trabalho, os ésteres metílicos de ácidos graxos (FAME) inibiram doze isolados clínicos do fungo patogênico Paracoccidioides brasiliensis, e também foi muito ativo no ensaio de bioautografia sobre o fungo Cladosporium sphaerospermum. CONCLUSÕES: FAME foi um antifúngico mais potente do que sulfametoxazol-trimetoprim contra P. brasiliensis, nas condições utilizadas no presente trabalho.


Assuntos
Annona/química , Antifúngicos/farmacologia , Ácidos Graxos/farmacologia , Éteres Metílicos/farmacologia , Paracoccidioides/efeitos dos fármacos , Extratos Vegetais/farmacologia , Antifúngicos/isolamento & purificação , Candida/classificação , Candida/efeitos dos fármacos , Cryptococcus gattii/efeitos dos fármacos , Ácidos Graxos/isolamento & purificação , Testes de Sensibilidade Microbiana , Éteres Metílicos/isolamento & purificação , Sementes/química
4.
J Nat Prod ; 74(8): 1707-12, 2011 Aug 26.
Artigo em Inglês | MEDLINE | ID: mdl-21805982

RESUMO

The metabolism of the fungistatic agent (8R,9R)-8-methoxyisocaryolan-9-ol (4) by the fungus Botrytis cinerea has been investigated. Biotransformation of compound 4 yielded compounds 5 and 6-9. No dihydrobotrydial is observed after 4 days of incubation of compound 4. Separate biotransformation of (8R,9R)-isocaryolane-8,9-diol (5) yielded compounds 7-11. The evaluation of the fungistatic activity against B. cinerea of compounds 4, 5, and 6 is reported. (4R,8R,9R)-8-Methoxyisocaryolane-9,15-diol (6), a major metabolite of (8R,9R)-8-methoxyisocaryolan-9-ol (4), shows a much reduced biological activity when compared with the parent compound. Isocaryolane derivatives 6-11 are described for the first time.


Assuntos
Botrytis/metabolismo , Fungicidas Industriais/metabolismo , Sesquiterpenos/farmacologia , Biotransformação , Botrytis/efeitos dos fármacos , Estrutura Molecular , Sesquiterpenos/química , Espectroscopia de Infravermelho com Transformada de Fourier , Estereoisomerismo
5.
Rev Soc Bras Med Trop ; 44(6): 777-80, 2011.
Artigo em Inglês | MEDLINE | ID: mdl-22231254

RESUMO

INTRODUCTION: Fatty acids are abundant in vegetable oils. They are known to have antibacterial and antifungal properties. METHODS: Antifungal susceptibility was evaluated by broth microdilution assay following CLSI (formerly the NCCLS) guidelines against 16 fungal strains of clinical interest. RESULTS: In this work, fatty acid methyl esters (FAME) was able to inhibit 12 clinical strains of the pathogenic fungus Paracoccidioides brasiliensis and were also active in the bioautographic assay against Cladosporium sphaerospermum. CONCLUSIONS: FAME was a more potent antifungal than trimethoprim-sulfamethoxazole against P. brasiliensis under the experimental conditions tested.


Assuntos
Annona/química , Antifúngicos/farmacologia , Ácidos Graxos/farmacologia , Éteres Metílicos/farmacologia , Paracoccidioides/efeitos dos fármacos , Extratos Vegetais/farmacologia , Antifúngicos/isolamento & purificação , Candida/classificação , Candida/efeitos dos fármacos , Cryptococcus gattii/efeitos dos fármacos , Ácidos Graxos/isolamento & purificação , Éteres Metílicos/isolamento & purificação , Testes de Sensibilidade Microbiana , Sementes/química
6.
J Nat Prod ; 73(8): 1431-3, 2010 Aug 27.
Artigo em Inglês | MEDLINE | ID: mdl-20617817

RESUMO

A new product of biotransformation of ent-16-oxo-17-norkauran-19-oic acid (1) by Fusarium proliferatum was isolated and identified as a 2beta-hydroxy derivative (2). The structure of 2 was elucidated on the basis of spectroscopic data interpretation and single-crystal X-ray diffraction analysis. The allelopathic activity of compound 2 was evaluated on the growth of radicals and shoots of Lactuca sativa (lettuce). This is the first time that fungal hydroxylation at position C-2 has been reported on an ent-kaurane diterpene skeleton.


Assuntos
Diterpenos do Tipo Caurano/química , Fusarium/metabolismo , Lactuca/efeitos dos fármacos , Biotransformação , Brasil , Cristalografia por Raios X , Hidroxilação , Lactuca/crescimento & desenvolvimento , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Wedelia/química
7.
J Agric Food Chem ; 56(9): 2985-8, 2008 May 14.
Artigo em Inglês | MEDLINE | ID: mdl-18393433

RESUMO

Novel kaurane ditepene monoamides were synthesized in good yields directly from kaurenoic ( 1) and grandiflorenic ( 2) acids and unprotected symmetrical diamines, using a modified protocol for monoacylation. Amides from 1 and 2 and monoamines were also obtained and tested against seed germination and growth of radicle and shoot of Lactuca sativa (lettuce), at 10 (-3), 10 (-5), and 10 (-7) M. Amides from symmetrical diamines showed significant inhibitory activity at higher concentrations.


Assuntos
Amidas/síntese química , Amidas/farmacologia , Diterpenos do Tipo Caurano/síntese química , Diterpenos do Tipo Caurano/farmacologia , Herbicidas/farmacologia , Plantas/efeitos dos fármacos , Diterpenos/química , Germinação/efeitos dos fármacos , Lactuca/efeitos dos fármacos , Lactuca/crescimento & desenvolvimento , Brotos de Planta/efeitos dos fármacos , Brotos de Planta/crescimento & desenvolvimento
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