Biocidal Compounds from Mentha sp. Essential Oils and Their Structure–Activity Relationships
- 18 February 2017
- journal article
- research article
- Published by Wiley in Chemistry & Biodiversity
- Vol. 14 (3)
- https://doi.org/10.1002/cbdv.201600270
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.Funding Information
- Ministerio de Economía y Competitividad (CTQ2012‐38219‐C03‐01, CTQ2015‐64049‐C3‐1‐R)
- European Social Fund
This publication has 39 references indexed in Scilit:
- Phytotoxic activity of foliar volatiles and essential oils ofCalamintha nepeta(L.) SaviNatural Product Research, 2013
- Chemical structures of p-menthane monoterpenes with special reference to their effect on seed germination and termite mortalityJournal of Wood Science, 2013
- Concentration and effect in mice of the essential oil pulegone from Mentha pulegium , a suspected toxic plant in Eastern Uruguay.Published by CABI Publishing ,2011
- Nematicidal Carboxylic Acids and Aldehydes from Melia azedarach FruitsJournal of Agricultural and Food Chemistry, 2010
- The Antigerminative Activity of Twenty-Seven MonoterpenesMolecules, 2010
- Terpenoid lactones with thep-menthane system as feeding deterrents to the lesser mealworm,Alphitobius diaperinusEntomologia Experimentalis et Applicata, 2008
- A Conjugated Diene Identified as a Prohapten: Contact Allergenic Activity and Chemical Reactivity of Proposed Epoxide MetabolitesChemical Research in Toxicology, 2005
- Clinal Variation ofMentha pulegiumEssential Oils Along the Climatic Gradient of GreeceJournal of Essential Oil Research, 2004
- Essential Oil Composition and Allelopathic Effect of the Brazilian Lamiaceae Hesperozygis ringens (Benth.) Epling and Hesperozygis rhododon EplingJournal of Agricultural and Food Chemistry, 1996
- Circular dichroism studies. The pulegone oxidesJournal of the Chemical Society C: Organic, 1970