Castaño Luisa M, Gómez Andrés F, Gil Jesús, Durango Diego
Universidad Nacional de Colombia-Sede Medellín, Facultad de Ciencias, Escuela de Química, Carrera 65, 59A-110, Medellín, Colombia.
Universidad Nacional de Colombia-Sede Medellín, Facultad de Ciencias Agrarias, Departamento de Ingeniería Agrícola y Alimentos, Carrera 65, 59A-110, Medellín, Colombia.
Heliyon. 2021 Mar 8;7(3):e06354. doi: 10.1016/j.heliyon.2021.e06354. eCollection 2021 Mar.
Metabolism and fungitoxicity of perinaphthenone against three economically important fungi of the citrus, spp, spp. and spp. were investigated. Perinaphthenone exhibited significant antifungal activity at 62.5 μM and above. Even, the inhibitory effect against spp. was significantly enhanced by exposure to direct light. In addition, the metabolism of perinaphthenone by the three fungi was studied. Results show that perinaphthenone was transformed almost completely during the first 24 h; two major products, whose concentration increased progressively during the twelve days of the test, were isolated and identified as 2,3-dihydro-1H-phenalen-1-ol and 2,3-dihydro-phenalen-1-one. Although both metabolic products displayed a considerable fungistatic effect, their slightly lower activities in comparison to perinaphthenone indicate that the transformation was a detoxification process. Studies on the relationship between the effect of some substituents in the perinaphthenone core and the mycelial growth inhibition of spp. were also carried out. Results show that the α, β-unsaturated carbonyl system is an important structural requirement but not the only to be necessary for the strong antifungal activity of perinaphthenone. In general, the antifungal properties of perinaphthenone may be modulated through the incorporation of substituents in the naphthalene core or in the α, β-unsaturated carbonyl system. It is concluded that perinaphthenone could be used as an antifungal agent or as a structural template for the development of new fungicide compounds.
研究了萘并环戊酮对柑橘的三种重要经济真菌（分别为 spp、spp 和 spp）的代谢及杀真菌毒性。萘并环戊酮在62.5μM及以上浓度时表现出显著的抗真菌活性。甚至，暴露于直射光下对 spp 的抑制作用会显著增强。此外，还研究了这三种真菌对萘并环戊酮的代谢情况。结果表明，萘并环戊酮在最初24小时内几乎完全转化；分离并鉴定出两种主要产物，其浓度在测试期的12天内逐渐增加，分别为2,3 - 二氢-1H - 菲-1 - 醇和2,3 - 二氢-菲-1 - 酮。虽然两种代谢产物都显示出相当大的抑菌作用，但与萘并环戊酮相比，其活性略低，这表明这种转化是一个解毒过程。还开展了关于萘并环戊酮核心中一些取代基的作用与 spp 菌丝体生长抑制之间关系的研究。结果表明，α,β - 不饱和羰基系统是一个重要的结构要求，但并非萘并环戊酮强大抗真菌活性所必需的唯一条件。一般来说，萘并环戊酮的抗真菌特性可通过在萘环核心或α,β - 不饱和羰基系统中引入取代基来调节。得出的结论是，萘并环戊酮可作为一种抗真菌剂或作为开发新型杀真菌剂化合物的结构模板。
