Inhibition of Acetylcholinesterase Activity by Monoterpenoids with a <i>p</i>-Menthane Skeleton

Miyazawa, Mitsuo; Watanabe, Hidenobu; Kameoka, Hiromu

doi:10.1021/jf960398b

Cited by 201 publications

(122 citation statements)

References 9 publications

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“…A utilização de espécies de plantas produtoras de óleos essenciais envolve deste a indústria de perfumes, de alimentos, como na medicina popular (Sonwa & König, 2001). Além disso, foram relatadas informações referentes à possibilidade de utilização de óleo essencial nas atividades agrícolas como alternativa viável com ação inseticida, fumigante e fungicida (Ismar, 2000;Miyazawa et al, 1997;Ngoh et al, 1998;Hoagland, 1999;MontesBelmont & Carvajal, 1999;Bastos & Albuquerque, 2004).…”

Section: Introductionunclassified

Efeitos potencialmente alelopáticos dos óleos essenciais de Piper hispidinervium C. DC. e Pogostemon heyneanus Benth sobre plantas daninhas

et al. 2009

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RESUMOEste trabalho teve por objetivo caracterizar a atividade potencialmente alelopática de óleos essenciais de pimenta longa (Piper hispidinervium C. DC.) e oriza (Pogostemon heyneanus Benth) e analisar, comparativamente, seus efeitos alelopáticos. Óleos essenciais obtidos foram preparados em concentrações de 0,25, 0,5 e 1,0%, tendo como eluente o éter metílico, e testados sobre a germinação de sementes, desenvolvimento da radícula e do hipocótilo das plantas daninhas de área de pastagens cultivadas, malícia (Mimosa pudica) e mata-pasto (Senna obtusifolia). Os óleos das duas espécies evidenciaram atividade alelopática em intensidades que variaram em função da concentração do óleo, da espécie doadora, da planta receptora e do fator da planta analisado. A germinação das sementes foi o fator mais intensamente inibido pelos óleos. As intensidades das inibições estiveram positivamente associadas à concentração, com inibições máximas verificadas a 1,0%. Malícia foi à espécie receptora mais sensível aos efeitos do óleo. Comparativamente, o óleo essencial da pimenta longa revelou maior potencial para inibir a germinação e o desenvolvimento das duas plantas receptoras, notadamente em relação à germinação de sementes, quando as diferenças foram mais marcantes. Os resultados foram atribuídos à composição química dos óleos, especialmente em relação à presença de monoterpenos, monoterpenos oxigenados e sesquiterpenos.PALAVRAS-CHAVE: Alelopatia, Inibição, Monoterpenos, Sesquiterpenos. Potentially allelopathic effects of the essential oils of Piper hispidinervium C. DC. and Pogostemon heyneanus (Benth) on weeds ABSTRACTThis study aimed to characterize the potential allelopathic activity of essential oils of pimenta longa (Piper hispidinervium C. DC.) and oriza (Pogostemon heyneanus Benth), and to examine, comparatively, their allelopathic effects. Essential oils obtained were prepared at concentrations of 0.25%, 0.5% and 1.0%, with ether methanol as eluent, and tested upon the germination of seeds and the development of the radicle and the hypocotyl of the weeds of cultivated grassland areas, malícia (Mimosa pudica) and mata-pasto (Senna obtusifolia). Depending on their concentrations, oils of the two species showed intensities of allelopathic activity on the donor species, on the receptor plant and on the examined plant factor. The germination of seeds was the factor most strongly inhibited by the oils. The intensities of inhibitions were positively related to the concentration, with the maximum inhibitions verified at 1%. Mimosa pudica was the receptor species most sensitive to the effects of oil. In comparison, the essential oil of Piper hispidinervium showed a higher potential for inhibiting the germination and development of the two receptor plants, notably in relation to the germination of seeds, when the differences were more striking. The results were attributed to the chemical composition of oils, especially in relation to the presence of monoterpenes, oxygenated monoterpenes and sesquiterpenes.

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Section: Introductionunclassified

Efeitos potencialmente alelopáticos dos óleos essenciais de Piper hispidinervium C. DC. e Pogostemon heyneanus Benth sobre plantas daninhas

et al. 2009

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“…The terpene hydrocarbon compounds reported similar AChE inhibitory activity to the terpene alcohols (Miyazawa et al, 1997). In bicyclic monoterpenes, the presence of oxygenated functional groups decreased the AChE inhibition.…”

Section: Acetylcholinesterase Inhibitionmentioning

confidence: 79%

Chemical composition and acetylcholinesterase inhibitory activity ofArtemisia maderaspatanaessential oil

Jyotshna¹,

Srivastava²,

Singh³

et al. 2015

Pharmaceutical Biology

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Context: To date, there are no reports to validate the Indian traditional and folklore claims of Artemisia maderaspatana L. (syn. Grangea maderaspatana L.) (Asteraceae) for the treatment of Alzheimer's disease. Objective: The present study characterizes the volatile components (non-polar compounds) of A. maderaspatana and evaluates its acetylcholinesterase inhibition potential. Materials and methods: The essential oils (yield 0.06% v/w) were obtained from fresh aerial part of A. maderaspatana. The characterization of volatile components (non-polar compounds) was performed by GC-MS data and with those of reference compounds compiled in the spectral library of in-house database. The in vitro acetylcholinesterase (AChE) inhibition of the volatile organic constituents (VOC's) of A. maderaspatana aerial part was evaluated in varying concentration ranges (0.70-44.75 mg/mL) with Ellman's method. Results: The major components were a-humulene (46.3%), b-caryophyllene (9.3%), a-copaene (8.2%), b-myrcene (4.3%), Z(E)-a-farnesene (3.7%), and calarene (3.5%). Chemical variability among other Artemisia spp. from different climatic regions of India and countries namely Iran and France was observed. The experimental results showed that diverse volatile organic constituents of A. maderaspatana have significant acetylcholinesterase inhibitory activity (an IC 50 value of 31.33 ± 1.03 mg/mL). This is the first report on the inhibition of acetylcholinesterase properties of essential oil of A. maderaspatana obtained from fresh aerial part. Conclusions: The present results indicate that essential oil of A. maderaspatana isolated from the northern region of India could inhibit AChE moderately. Therefore, the possibility of novel AChE inhibitors might exist in VOCs of this plant.

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“…Monoterpenes in several essential oils have been shown to be competitive inhibitors of AChE. Miyazawa et al 16 reported the inhibition of AChE from bovine erythrocytes by certain monoterpenoids, such as p-cymene and g-terpinene. Mills et al 17 found the AChE in lice was inhibited by two major constituents (1,8-cineole and terpinen-4-ol) of tea tree oil.…”

Section: Discussionmentioning

confidence: 99%

Biological performance of Eucalyptus camaldulensis leaf oils from Thailand against the subterranean termite Coptotermes formosanus Shiraki

2009

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The antitermitic activities of leaf oils and their constituents, taken from three clones of Eucalyptus camaldulensis Dehnh. in Thailand, against Coptotermes formosanus Shiraki were investigated in contact and noncontact tests. The termiticidal mechanism was also examined. Antitermitic tests demonstrated that E. camaldulensis leaf oils were both contact toxicants and fumigants to C. formosanus with LC 50 values ranging between 12.68 and 17.50 mg/ g by the contact method, and between 12.65 and 17.50 mg/ petri dish (100 cm 3 ) by the noncontact method. p-Cymene and g-terpinene were primarily responsible for the contact toxicity and 1,8-cineole was responsible for fumigation. From the investigation of termiticidal mechanism, E. camaldulensis leaf oils exhibited the inhibition of acetylcholinesterase activity and showed the common symptoms of a neurotoxic mode of action against C. formosanus.

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Inhibition of Acetylcholinesterase Activity by Monoterpenoids with a p-Menthane Skeleton

Cited by 201 publications

References 9 publications

Efeitos potencialmente alelopáticos dos óleos essenciais de Piper hispidinervium C. DC. e Pogostemon heyneanus Benth sobre plantas daninhas

Efeitos potencialmente alelopáticos dos óleos essenciais de Piper hispidinervium C. DC. e Pogostemon heyneanus Benth sobre plantas daninhas

Chemical composition and acetylcholinesterase inhibitory activity ofArtemisia maderaspatanaessential oil

Biological performance of Eucalyptus camaldulensis leaf oils from Thailand against the subterranean termite Coptotermes formosanus Shiraki

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