Kimbaris Athanasios C, González-Coloma Azucena, Andrés Maria Fe, Vidali Veroniki P, Polissiou Moschos G, Santana-Méridas Omar
Laboratory of Chemistry & Biochemistry, Department of Agricultural Development Democritus, University of Thrace, 193, Pantazidou str, 68200, N. Orestiada, Greece.
Instituto de Ciencias Agrarias, CSIC, Serrano 115, 28006, Madrid, Spain.
Chem Biodivers. 2017 Mar;14(3). doi: 10.1002/cbdv.201600270. Epub 2017 Feb 18.
Essential oils from Greek Mentha species showed different chemical compositions for two populations of M. pulegium, characterized by piperitone and pulegone. Mentha spicata essential oil was characterized by endocyclic piperitenone epoxide, piperitone epoxide, and carvone. The bioactivities of these essential oils and their components have been tested against insect pests (Leptinotarsa decemlineata, Spodoptera littoralis and Myzus persicae), root-knot nematodes (Meloydogine javanica) and plants (Lactuca sativa, Lolium perenne, Solanum lycopersicum). The structure-activity relationships of these compounds have been studied including semi-synthetic endocyclic trans-carvone epoxide, exocyclic carvone epoxide, a new exocyclic piperitenone epoxide and trans-pulegone epoxide. Leptinotarsa decemlineata feeding was affected by piperitenone and piperitone epoxide. Spodoptera littoralis was affected by piperitone epoxide and pulegone. The strongest nematicidal agent was piperitenone epoxide, followed by piperitone epoxide, piperitenone and carvone. Germination of S. lycopersicum and L. perenne was significantly affected by piperitenone epoxide. This compound and carvone epoxide inhibited L. perenne root and leaf growth. Piperitenone epoxide also inhibited the root growth of S. lycopersicum. The presence of a C(1) epoxide resulted in strong antifeedant, nematicidal and phytotoxic compounds regardless of the C(4) substituent. New natural crop protectants could be developed through appropriate structural modifications in the p-menthane skeleton.
希腊薄荷属植物的精油对两个唇萼薄荷种群表现出不同的化学成分，其特征为含有哌啶酮和长叶薄荷酮。留兰香精油的特征成分是内环氧胡椒酮、胡椒酮氧化物和香芹酮。这些精油及其成分的生物活性已针对害虫（马铃薯甲虫、海滨夜蛾和桃蚜）、根结线虫（爪哇根结线虫）和植物（生菜、多年生黑麦草、番茄）进行了测试。已对这些化合物的构效关系进行了研究，包括半合成的内环氧反式香芹酮氧化物、外环氧香芹酮氧化物、一种新的外环氧胡椒酮氧化物和反式长叶薄荷酮氧化物。马铃薯甲虫的取食受到胡椒酮和胡椒酮氧化物的影响。海滨夜蛾受到胡椒酮氧化物和长叶薄荷酮的影响。最强的杀线虫剂是胡椒酮氧化物，其次是胡椒酮氧化物、胡椒酮和香芹酮。胡椒酮氧化物显著影响番茄和多年生黑麦草的发芽。该化合物和香芹酮氧化物抑制多年生黑麦草的根和叶生长。胡椒酮氧化物也抑制番茄的根生长。无论C(4)取代基如何，C(1)环氧基团的存在都会产生强拒食、杀线虫和植物毒性化合物。通过对对薄荷烷骨架进行适当的结构修饰，可以开发出新的天然作物保护剂。
