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.

Combined Action of Piperitenone Epoxide and Antibiotics Against Clinical Isolates of Staphylococcus aureus and Escherichia coli

“…The resulted yellowish oil, identified as (+)-PEO (1.6 g, mixture of cis and trans diastereoisomers), was found in high purity (∼99.0%) according to GC-MS analysis. Structural determination was carried out by GC-MS and 1 H- and 13 C-NMR analysis, and the results were in agreement to previously reported (Kimbaris et al, 2017).…”

“…Isolation and structural characterization of PEO followed the procedure as we previously described (Kimbaris et al, 2017). Briefly, aerial parts of full flowered plants of M. spicata were collected during July of 2018 from a wild-growing population in Sparti (South of Greece, Peloponisos).…”

Acaricidal and Insect Antifeedant Effects of Essential Oils From Selected Aromatic Plants and Their Main Components

“…This species' EOs also have reported insecticidal effects against stored-product pests such as Sitophilus oryzae (piperitenone oxide and piperitenone oxide/piperitenone chemotypes) (Zekri et al, 2013), Rizopertha dominica (piperitenone/pulegone/piperitone) (Benayad et al, 2012), and Triboleum castaneum (menthone/pulegone) (Kasrati et al, 2015) and larvicidal activity against C. quinquefasciatus (piperitenone oxide) (Pavela et al, 2014). Antifeedant effects against L. decemlineata and M. persicae have been reported for a piperitenone oxide/piperitone epoxide Mentha chemotype (Kimbaris et al, 2017). However, this is the first report on the ixodicidal effects of a piperitenone oxide/piperitenone M. suaveolens chemotype.…”

“…Piperitenone epoxide and piperitenone showed strong larvicidal and repellent effects against Aedes albopictus (Giatropoulos et al, 2018). Piperitenone was antifeedant to L. decemlineata and S. littoralis (Kimbaris et al, 2017). However, there are no reports on the acaricidal effects of these compounds.…”

Diastereoselective Synthesis of 7,8-Carvone Epoxides

“…However, when the epoxidation of the isopropylidene group with m-CPBA is carried out, no diastereoselection is obtained [8,9]. Recently, very interesting biological applications of the natural 7,8-epoxides mixture of carvone [10] have been described: of anti-inflammatory [10], antifeedant, and phytotoxic [11] nature. To obtain these epoxy derivatives, the organic oxidants used for the epoxidation reaction are rather expensive and have to be used in a stoichiometric manner, and even in those conditions, the reaction yields are rather small.…”