Effects of Piperitone on the Antimicrobial Activity of Nitrofurantoin and on Nitrofurantoin Metabolism by<i>Enterobacter cloacae</i>.

Abdolpour, Farid; Shahverdi, A R; Rafii, Fatemeh; Fazeli, Mehdi; Amini, Mohsen

doi:10.1080/13880200701213161

Cited by 10 publications

(4 citation statements)

References 15 publications

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“…However, according to a recent investigation, piperitone showed antibacterial activity against some bacteria especially B. dipesauri [16] and A. flavus growth at relatively low concentration[17]. Piperitone increases nitrofurantoin susceptibility and reduces the activity of nitro reductase in a dose-dependent manner in Enterobacteriaceae [18]. …”

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confidence: 99%

Biochemical activities of iranian Cymbopogon olivieri (Boiss) Bor. essential oil

Mahboubi¹,

Kazempour²

2012

Indian J Pharm Sci

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Cymbopogon olivieri essential oil from aerial parts was analyzed by gas chromotography and gas chromatography-mass spectrometry and led to the identification of 38 compounds. Piperitone (72.8%), 4-carene (11.8%) and β-himachalene (7.6%) were found as the major components of the oil. The antimicrobial activity was achieved using disc-diffusion and microbroth dilution assays and microbicidal kinetics of oil was screened against different microorganisms. The possible antioxidant activity of oil was evaluated by diphenylpicrylhydrazyl free-radical scavenging system. The oil had excellent antimicrobial activity against Bacillus cereus, Staphylococcus epidermidis and Streptococcus pneumoniae. The oil exhibited inhibitory effect against Bacillus subtilis and fungi. Dvalues of oil were 12.5, 10 and 2.4 min for Escherichia coli, Staphylococcus aureus and Candida albicans, respectively. The IC50 value of Cymbopogon olivieri oil was 35 mg/ml and its antioxidant activity was lower than that of butylated hydroxytoluene. Cymbopogon olivieri oil possesses compounds with antimicrobial properties that can be used as antimicrobial agents.

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confidence: 99%

Biochemical activities of iranian Cymbopogon olivieri (Boiss) Bor. essential oil

Mahboubi¹,

Kazempour²

2012

Indian J Pharm Sci

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“…There is a limited number of Based on the known properties of piperitone, we can speculate on its potential contributions within A. judaica. Piperitone is recognized for its antimicrobial, antifungal, and anti-inflammatory properties [43]. Interestingly, A. judaica essential oil itself exhibits similar antifungal and anti-inflammatory activities [6].…”

Section: Discussionmentioning

confidence: 99%

Chemical Composition and Cytotoxicity Evaluation of Artemisia judaica L. Essential Oil from Saudi Arabia

Alsharif,

Bashir,

Boylan

2024

Molecules

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Gas chromatography (GC) and gas chromatography–mass spectrometry (GC–MS) analyses were conducted on essential oil extracted from Saudi Arabian Artemisia judaica L. (A. judaica) aerial parts, resulting in the identification of 58 constituents, representing 93.0% of the total oil composition. The oil primarily consisted of monoterpenes (38.6%), sesquiterpenes (14.1%), and other compounds such as ethyl esters and cyclic ketones (40.3%). The main components identified were piperitone (16.5%), ethyl cinnamate (12.9%), and camphor (9.7%). Multivariate statistical analyses (MVAs), including principal component analysis (PCA) and agglomerative hierarchical clustering (AHC) analysis, were employed to compare the chemical makeup of this oil with 20 other A. judaica oils from various regions. The study revealed distinct clusters, highlighting unique chemotypes and geographic variations. Particularly, the oil from the current study demonstrated a specialized chemical profile with significant concentrations of specific compounds, contributing significantly to its distinctiveness. Further cytotoxicity testing on RAW264.7 macrophages suggested that concentrations below 20 μg/mL of A. judaica oil are suitable for future pharmacological investigations. This study provides valuable insights into the chemical diversity, geographic variations, and potential biomedical applications of these essential oils.

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“…We previously have shown that essential oils of several plants enhance the potency of nitrofurantoin for different bacteria and monoterpene derivatives are among the active compounds enhancing the antimicrobial activities of nitrofurantoin [13][14][15]. Using computer-aided molecular modeling and docking techniques [16,17], we elucidated the interaction between monoterpenes and nitroreductase [18].…”

Section: Introductionmentioning

confidence: 98%

Monoterpenes as nitrofurantoin resistance modulating agents: minimal structural requirements, molecular dynamics simulations, and the effect of piperitone on the emergence of nitrofurantoin resistance in Enterobacteriaceae

et al. 2015

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The effects of different monoterpenes and 2-cyclohexen-1-one on the antibacterial activity of nitrofurantoin against resistant Enterobacter cloacae, were compared and the minimal structural component of monoterpene required for the highest level of resistance-modulating activity was determined. Subinhibitory concentrations of all compounds tested enhanced the antibacterial activity of nitrofurantoin against E. cloacae to different extents. The highest synergistic effect was observed for the monoterpenes, like piperitone, which contained a conjugated ketone and C=C bond in their carbon ring structure. Piperitone also suppressed the emergence of nitrofurantoin-resistant strains of Enterobacteriaceae that were mutagenized by ethyl methanesulfonate. The modes of interaction of carvone, piperitone, and an enzyme inhibitor, benzoate, with nitroreductase were investigated by molecular docking and molecular dynamic (MD) simulation for 20 ns. MD simulation supported greater stability of the benzoate and monoterpene-nitroreductase (NR) complexes than of free NR. The results of this investigation are promising for the synthesis of more effective lead compounds to enhance the antibacterial activity of nitro drugs against resistant Enterobacter strains.

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Effects of Piperitone on the Antimicrobial Activity of Nitrofurantoin and on Nitrofurantoin Metabolism byEnterobacter cloacae.

Cited by 10 publications

References 15 publications

Biochemical activities of iranian Cymbopogon olivieri (Boiss) Bor. essential oil

Biochemical activities of iranian Cymbopogon olivieri (Boiss) Bor. essential oil

Chemical Composition and Cytotoxicity Evaluation of Artemisia judaica L. Essential Oil from Saudi Arabia

Monoterpenes as nitrofurantoin resistance modulating agents: minimal structural requirements, molecular dynamics simulations, and the effect of piperitone on the emergence of nitrofurantoin resistance in Enterobacteriaceae

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