Chemical structures of p-menthane monoterpenes with special reference to their effect on seed germination and termite mortality

Sekine, Nobuhiro; Shibutani, Sakae

doi:10.1007/s10086-013-1327-5

Cited by 16 publications

(17 citation statements)

References 17 publications

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“…littoralis , M . persicae among other insect species, toxicity, insect growth inhibition and related effects . Pulegone epoxide, carvone, carvone epoxide, piperitenone oxide, and piperitone have been reported as a strong antifeedants, toxic, and repellent against chewing and sucking insects …”

Section: Resultsmentioning

confidence: 99%

“…have been previously described for their ability to affect the plant germination and/or the development of roots and hypocotyls . A wide range of volatile p ‐menthane monoterpenes released by these species are able to inhibit both germination and plant growth of many species and could be considered for its potential use as commercial natural herbicides . Overall, phytotoxic activity is often attributed to synergistic effects of all components of the essential oil through different processes including enzyme inhibition, chlorophyll degradation, electrolyte leakage and membrane damage …”

Section: Resultsmentioning

confidence: 99%

“…Monoterpenes of the p ‐menthane group are the main constituents of Mentha spp. essential oils and have attracted interest for their chemistry and biological properties . In this connection, the current methods for the commercial production of specific‐high‐value p‐ menthane monoterpenes are chemical synthesis or isolation from natural sources …”

Section: Introductionmentioning

confidence: 99%

“…essential oils and have attracted interest for their chemistry and biological properties. [6] In this connection, the current methods for the commercial production of specific-high-value p-menthane monoterpenes are chemical synthesis or isolation from natural sources. [7] The essential oil of M. pulegium (pennyroyal oil) contains between 25 and 90% pulegone.…”

Section: Introductionmentioning

confidence: 99%

“…The bioactivities of the major components of the essential oils (compounds 1 -10, Fig. 1) have also been tested and their structure-activity relationships studied by comparison with semi-synthetic epoxy-derivatives including endocyclic trans-carvone epoxide (2), exocyclic carvone epoxide (3), the new exocyclic piperitenone epoxide (6) and trans-pulegone epoxide (8).…”

Section: Introductionmentioning

confidence: 99%

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

Kimbaris

González-Coloma⊥

Andrés

et al. 2017

Chemistry & Biodiversity

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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.

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