RESUMEN
The relationship between the stereochemistry and antimicrobial activity of butane-type lignans was clarified. All stereoisomers of dihydroguaiaretic acid (DGA) showed both antibacterial and antifungal activity. The (+)- and (-)-7,7'-dioxodihydroguaiaretic acid (ODGA) also showed both antibacterial and antifungal activity, while meso-ODGA did not show antibacterial activity, but showed antifungal activity. No activity of any stereoisomer of secoisolariciresinol (SECO) was apparent.
Asunto(s)
Antiinfecciosos/química , Antiinfecciosos/farmacología , Butanos/química , Guayacol/análogos & derivados , Lignanos/química , Lignanos/farmacología , Antiinfecciosos/síntesis química , Bacterias/efectos de los fármacos , Enfermedades Transmitidas por los Alimentos/microbiología , Hongos/efectos de los fármacos , Guayacol/síntesis química , Guayacol/química , Guayacol/farmacología , Lignanos/síntesis química , Enfermedades de las Plantas/microbiología , Estereoisomerismo , Relación Estructura-Actividad , Especificidad por SustratoRESUMEN
The syntheses of all stereoisomers of tetrasubstituted tetrahydrofuran lignan were accomplished, and the antimicrobial activity was examined. The 9,9'-diol compound bearing (7R,7'R,8R,8'R) and (7R,7'S,8R,8'R) stereochemistry showed the strongest antibacterial activity against Listeria denitrificans and Bacillus subtilis, respectively. It was also found that (-)-virgatusin bearing (7S,7'R,8S,8'S) stereochemistry had strongest antifungal activity.
Asunto(s)
Antiinfecciosos/química , Antiinfecciosos/farmacología , Furanos/química , Lignanos/química , Lignanos/farmacología , Antiinfecciosos/síntesis química , Bacterias/efectos de los fármacos , Lignanos/síntesis química , Pruebas de Sensibilidad Microbiana , Estereoisomerismo , Relación Estructura-ActividadRESUMEN
The antimicrobial activity of all stereoisomers of morinols A and B was tested. All stereoisomers of morinols A and B showed antifungal activity against Alternaria alternata, especially (-)-morinol B which showed the strongest activity. The natural component, (+)-morinol A, and unnatural stereoisomer, (7S,7'S,8R,8'R)-morinol B, showed antibacterial activity against the gram-positive bacteria, Bacillus subtilis and Listeria denitrificans.
Asunto(s)
Antibacterianos/química , Antifúngicos/química , Lignanos/farmacología , Piranos/farmacología , Alternaria , Bacillus subtilis , Bacterias Grampositivas , Lignanos/química , Listeria , Piranos/química , EstereoisomerismoRESUMEN
All stereoisomers of goniodiol were synthesized from yeast-reduction products. The C-6 chiral centers were converted from the chiral centers of the yeast-reduction products. Stereoselective conversion of the alkene, which had been prepared from the yeast-reduction product, to glycol constructed the C-7 and C-8 stereochemistry. (+)-Goniodiol and 7-epi-(+)-goniodiol showed the highest antibacterial activity (MIC, 3.1 mM) against Yersinia intermedia.
Asunto(s)
Antibacterianos/síntesis química , Pironas/química , Levaduras/química , Alcoholes/química , Alquenos/química , Antibacterianos/química , Antibacterianos/farmacología , Furanos/química , Pruebas de Sensibilidad Microbiana , Conformación Molecular , Estructura Molecular , Rotación Óptica , Estereoisomerismo , Relación Estructura-Actividad , Yersinia/efectos de los fármacosRESUMEN
The relationship between the antibacterial activity and structure of 9-O,9'-O-demethyl (+)-virgatusin (Virg 3) was examined. The conversion of hydroxy groups on the 9 and 9' positions to amino groups increased the activity. It was found that the 3'-methoxy group was more important for higher activity than the 4'-methoxy group on the 7'-phenyl group, and that the 3,4-methylenedioxy group on the 7-phenyl group was necessary for activity.
Asunto(s)
Antibacterianos/química , Antibacterianos/farmacología , Furanos/química , Furanos/farmacología , Productos Biológicos/química , Productos Biológicos/farmacología , Lignanos/química , Lignanos/farmacología , Pruebas de Sensibilidad Microbiana , Relación Estructura-ActividadRESUMEN
The effect of oxidation degree at the benzylic position of 2,3-dibenzyl-4-butanolide and 3,4-dibenzyltetrahydrofuran lignans on the antimicrobiological activity was examined. The highest oxidation degree at the benzylic position of 2,3-dibenzyl-4-butanolide gave the greatest activity, and 3,4-dibenzoyltetrahydrofuran showed the highest antifungal activity. The relationship between stereochemistry and activity was also examined. Both enantiomers of cis-matairesinol were synthesized for the first time, one of the cis-matairesinols showing antibacterial activity.
Asunto(s)
Antiinfecciosos/farmacología , Furanos/farmacología , Lignanos/farmacología , Oxígeno/química , 4-Butirolactona/química , 4-Butirolactona/farmacología , Antiinfecciosos/química , Bacillus subtilis/efectos de los fármacos , Furanos/química , Lignanos/química , Conformación Molecular , Pseudomonas fluorescens/efectos de los fármacos , Staphylococcus aureus/efectos de los fármacos , Relación Estructura-ActividadRESUMEN
The relationship between antibacterial activity of tetra-substituted tetrahydrofuran lignans (1-4) and their absolute configurations was tested. Only compound 4 among two virgatusins and two related compounds exhibited growth inhibitory activity against the Gram-positive bacteria Bacillus subtilis, Staphylococcus aureus and Listeria denitrificans. Compound 4 affected the growth of B. subtilis in a bactericidic manner, and its ability to dissipate the cytoplasmic membrane potential was investigated using the fluorescence probe 3,3'-dipropylthiadicarbocyanine iodide. These results suggested that compound 4 damages cells by causing the loss of the proton motive force and disruption of the cellular integrity of the membrane, leading to cell death. In addition, it was shown that the antibacterial activity of a lignan was closely related to its absolute configuration and functional groups.