Limonene

Thomas, Alan F.; Bessière, Y.

doi:10.1039/np9890600291

Cited by 111 publications

(65 citation statements)

References 71 publications

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“…The compounds limonene oxide (Thomas and Bessiere, 1989), pulegone oxide (Katsuhara, 1967) and carvone epoxide (Santos et al, 1997) were prepared in our laboratory as previously described. (+)-Pulegone, (Ð)-carvone and (+)-carvone were purchased from Aldrich.…”

Section: Chemicals and Solutionsmentioning

confidence: 99%

Structure and Spasmolytic Activity Relationships of Monoterpene Analogues Found in Many Aromatic Plants

Sousa

Júnior

Andrade

et al. 2008

Zeitschrift Für Naturforschung C

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Rotundifolone, a monoterpene isolated from the essential oil of the leaves of Mentha ¥ villosa, is a constituent of several essential oils and known to have spasmolytic activity. The present study aimed to investigate the correlation between structure and spasmolytic activity of rotundifolone and its analogues in ileum isolated from guinea-pig. Five of the seven tested analogues were found to have a spasmolytic effect more potent than rotundifolone itself, except for pulegone and (+)-limonene. The comparison between rotundifolone and limonene oxide showed that the absence of the keto group did not decrease the relaxant effect. Comparison of the spasmolytic activity between rotundifolone and (+)-pulegone showed that the absence of the epoxy group did not decrease the relaxation of the ileum. Carvone epoxide was found to be significantly more potent than rotundifolone. The monoterpene (Ð)-carvone produced ileum relaxation and was more potent than its enantiomer (+)-carvone. (+)-Limonene and pulegone oxide showed a similar effect. The study showed that the functional groups and their position at the ring of rotundifolone contributed to the relaxation activity of the ileum. The absence of the oxygenated molecular structure is not a critical requirement for the molecule to be bioactive.

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Section: Chemicals and Solutionsmentioning

confidence: 99%

Structure and Spasmolytic Activity Relationships of Monoterpene Analogues Found in Many Aromatic Plants

Sousa

Júnior

Andrade

et al. 2008

Zeitschrift Für Naturforschung C

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“…The substances limonene oxide (Thomas;Bessiere, 1989), pulegone oxide (Katsuhara, 1967), and carvone epoxide (Santos et al, 1997) were prepared as previously described. (+)-Pulegone was purchased from Aldrich.…”

Section: Rotundifolone Analoguesmentioning

confidence: 99%

Preliminary study of the antimicrobial activity of Mentha x villosa Hudson essential oil, rotundifolone and its analogues

Arruda¹,

Antunes²,

Catão³

et al. 2006

Rev. bras. farmacogn.

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RESUMO: "Estudo preliminar da atividade antimicrobiana do óleo essencial de Mentha x villosa Hudson, rotundifolona e seus análogos". Os óleos essenciais apresentam atividade antimicrobiana contra uma variedade de bactérias e fungos, incluindo espécies resistentes a antibióticos e antimicóticos. Neste contexto, este trabalho objetiva a avaliação da atividade de antimicrobiana do óleo essencial de Mentha x villosa Hudson (hortelã-da-folha-miúda) -seu componente majoritário (rotundifolona) e quatro análogos sintéticos da rotundifolona (epóxi-limoneno epóxi-pulegona, epóxi-carvona e (+)-pulegona) frente a cepas padrão de Staphylococcus aureus ATCC 25923, Escherichia coli ATCC 25922 Pseudomonas aeruginosa ATCC 27853, Candida albicans ATCC 76645 e uma cepa de Staphylococcus aureus meticilina -resistente -MRSA (171c) de clínica humana. Como método, foi utilizada a difusão em placas com médio sólido. Os resultados mostraram que o óleo de Mentha x villosa, rotundifolona, epóxi-limoneno e (+)-pulegona, são semelhante em função da atividade antimicrobiana para as cepas de S. aureus e C.albicans testadas. Todos os produtos apresentaram potencial antimicrobiano com atividade antibacteriana para S. aureus ATCC 25923 e atividade antifúngica para C. albicans ATCC 76645. Nenhum dos produtos apresentou atividade antimicrobiana para as cepas de E. coli ATCC 25922 e P. aeruginosa ATCC 27853, representantes das bactérias Gram negativas.Unitermos: Mentha x villosa, Labiatae, óleo essencial, rotundifolona, atividade antimicrobiana. ABSTRACT:Essential oils present antimicrobial activity against a variety of bacteria and yeasts, including species resistant to antibiotics and antifungicals. In this context, this work aims at the evaluation of the antimicrobial activity of the essential oil of Mentha x villosa Hudson ("hortelã da folha miúda"), its major component (rotundifolone) and four similar analogues of rotundifolone (limonene oxide, pulegone oxide, carvone epoxide and (+)-pulegone) against strain standards of Staphylococcus aureus ATCC 25923, E. coli ATCC 25922, Pseudomona aeruginosa ATCC 27853, Candida albicans ATCC 76645 and one strain of meticilin -resistant Staphylococcus aureus -MRSA (171c) from human clinic. The method of the diffusion in plates with solid medium was used. The results showed that the oil of Mentha x villosa, rotundifolone, limonene oxide and (+)-pulegone, are similar regarding the antimicrobial activity against the tested strains of S. aureus and C. albicans. All of the products present antimocrobial potential with antibacterial activity for S. aureus ATCC 25923 and antifungal activity for C. albicans ATCC 76645. None of the products presented antimicrobial activity for the strains of E. coli ATCC 25922 and P. aeruginosa ATCC 27853, representatives of the Gram negative bacteria.

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“…Its chemistry is vast. Its action on the acids, bases, alcohols and other reagents is described [32]. The reaction of limonene with phenols dates from 1922 [33], and the products have been patented as resins and lacquers.…”

Section: Mechanism Involving Limonene Main Sensitizer Of Orange Peelsmentioning

confidence: 99%

Adsorptive removal of catechol and resorcinol by orange flavedo (citrus sinensis): mechanisms based on the flavedo com-ponents d-limonene, carotenoids, ascorbates, flavonoids and hydroxycinnamic acids

Kamgaing¹,

Doungmo²,

Julio³

et al. 2017

IJBAS

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Orange flavedo and its adsorption behavior towards catechol (Ctc) and resorcinol (Res) were studied. Adsorption experiments were conducted in batch mode at room temperature. X-ray diffraction (XRD), Scanning electron microscopy (SEM), Energy-dispersive X-ray spectroscopy (EDX), Brunauer−Emmett−Teller (BET) and Fourier transform infrared (FTIR) data were used to characterize the biosorbent. The Effects of various parameters including equilibrium pH, sorbent dosage, initial adsorbate concentration and contact time were investigated. The optimum contact time and pH for the removal of Ctc and Res were 35 min and pH 2 respectively. The adsorption isotherms fitted well with Freundlich model, the adsorption of Ctc and Res being multilayer and the surface of orange flavedo heterogeneous; the pseudo-second order kinetic model better reflects the adsorption phenomena. An adsorption mechanism based on the molecules grafted to the surface of the orange flavedo is proposed in this study. 0.2 gram of the biosorbent was sufficient to completely eliminate 2.2 milligrams of resorcinol and catechol from solution. Therefore, non-modified orange flavedo is a promising candidate, as a lowcost biosorbent, for the removal of Ctc and Res from aqueous solution.

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Limonene

Cited by 111 publications

References 71 publications

Structure and Spasmolytic Activity Relationships of Monoterpene Analogues Found in Many Aromatic Plants

Structure and Spasmolytic Activity Relationships of Monoterpene Analogues Found in Many Aromatic Plants

Preliminary study of the antimicrobial activity of Mentha x villosa Hudson essential oil, rotundifolone and its analogues

Adsorptive removal of catechol and resorcinol by orange flavedo (citrus sinensis): mechanisms based on the flavedo com-ponents d-limonene, carotenoids, ascorbates, flavonoids and hydroxycinnamic acids

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