Biocidal Compounds from Mentha sp. Essential Oils and Their Structure–Activity Relationships

• Published in: Chemistry & biodiversity Vol. 14; no. 3; pp. np - n/a
• Main Authors: Kimbaris, Athanasios C., González‐Coloma, Azucena, Andrés, Maria Fe, Vidali, Veroniki P., Polissiou, Moschos G., Santana‐Méridas, Omar
• Format: Journal Article
• Language: English
• Published: Switzerland Wiley Subscription Services, Inc 01.03.2017
• Subjects: Animals; Antifeedant; Epoxide; Epoxy Compounds - chemistry; Gas Chromatography-Mass Spectrometry; Germination - drug effects; Lactuca sativa; Leptinotarsa decemlineata; Lolium perenne; Lycopersicon esculentum - drug effects; Lycopersicon esculentum - growth & development; Mentha; Mentha - chemistry; Mentha - metabolism; Mentha spicata; Monoterpenes - analysis; Monoterpenes - chemistry; Monoterpenes - pharmacology; Myzus persicae; Nematicidal; Nematoda; Oils, Volatile - chemistry; Oils, Volatile - pharmacology; Plant Leaves - chemistry; Plant Leaves - metabolism; Plant Roots - drug effects; Plant Roots - growth & development; p‐Menthane monoterpene; Solanum; Spodoptera - drug effects; Spodoptera littoralis; Structure-Activity Relationship; Structure–activity relationship (SAR); Nematicidal; p-Menthane monoterpene; Structure-activity relationship (SAR); Antifeedant; Epoxide
• ISSN: 1612-1872; 1612-1880
• DOI: 10.1002/cbdv.201600270

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.