title: Biocidal Compounds from Mentha sp. Essential Oils and Their Structure-Activity Relationships.
abstract: 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.
authors: Laboratory of Chemistry & Biochemistry, Department of Agricultural Development Democritus, University of Thrace, 193, Pantazidou str, 68200, N. Orestiada, Greece.
authors: Athanasios C
authors: AC
authors: Kimbaris
authors: Instituto de Ciencias Agrarias, CSIC, Serrano 115, 28006, Madrid, Spain.
authors: Azucena
authors: A
authors: González-Coloma
authors: Instituto de Ciencias Agrarias, CSIC, Serrano 115, 28006, Madrid, Spain.
authors: Maria Fe
authors: MF
authors: Andrés
authors: Laboratory of Synthesis of Natural Products and Bioorganic Chemistry, Institute of Nanoscience and Nanotechnology, NCSR "Demokritos", P.O. Box 60228, GR-153 10 Ag. Paraskevi, Athens, Greece.
authors: Veroniki P
authors: VP
authors: Vidali
authors: Laboratory of Chemistry, Department of Food Science & Human Nutrition, Agricultural University of Athens, Iera Odos 75, 11855, Athens, Greece.
authors: Moschos G
authors: MG
authors: Polissiou
authors: R&D Dpt. Botanical Extracts, Kimitec, Santa Marta 13, Roquetas de Mar, Almeria, Spain.
authors: Omar
authors: O
authors: Santana-Méridas
mesh_terms: D000818:Animals; D000081005:Cyclohexane Monoterpenes; D004852:Epoxy Compounds / Q000737:chemistry; D008401:Gas Chromatography-Mass Spectrometry; D018525:Germination / Q000187:drug effects; D018551:Solanum lycopersicum / Q000187:drug effects / Q000254:growth & development; D027541:Mentha / Q000737:chemistry* / Q000378:metabolism; D039821:Monoterpenes / Q000032:analysis / Q000737:chemistry / Q000494:pharmacology; D009822:Oils, Volatile / Q000737:chemistry* / Q000494:pharmacology; D018515:Plant Leaves / Q000737:chemistry / Q000378:metabolism; D018517:Plant Roots / Q000187:drug effects / Q000254:growth & development; D018411:Spodoptera / Q000187:drug effects; D013329:Structure-Activity Relationship
chemical_list: D000081005:Cyclohexane Monoterpenes; D004852:Epoxy Compounds; D039821:Monoterpenes; D009822:Oils, Volatile; C496656:piperitone; C006923:carvone; C044956:piperitenone
keywords: Antifeedant; Epoxide; Nematicidal; Structure-activity relationship (SAR); p-Menthane monoterpene