Study of the Structural Changes on the Antimicrobial Activity of [3.1.1.]-Bicyclics

Dhar, Preeti; Ayala, Ulysses; Andarge, Eleni; Morisseau, Sophia; Snyder-Leiby, Teresa

doi:10.1080/10412905.2004.9698809

Cited by 5 publications

(6 citation statements)

References 19 publications

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“…Earlier studies have shown that introducing a single alcoholic (or amino functional group) in the α-pinene nucleus increases the antimicrobial activity, compared to the antimicrobial activity of (+)-α-pinene derivatives having other functional groups . It is speculated that the presence of the alcoholic or amino functional group makes the compound more water-soluble and thereby helps it transverse the polar cell wall. − This allows the compound to reach the site of action, the microbial membrane, in greater concentration and hence permeate it more efficiently. − Therefore, we chose to synthesize amino ester 13a and amino alcohol 14a to determine if adding both the alcoholic and amino functions to the α-pinene nucleus will make the compound more antimicrobial than when only one of the two functional groups is present.…”

Section: Resultsmentioning

confidence: 99%

“…The antimicrobial activity of the nine compounds synthesized was evaluated against four test microorganisms (Gram-positive bacteria S. aureus and M. luteus , Gram-negative bacterium E. coli , and unicellular fungus C. albicans ) by bioautographic assay using a modified published procedure. , Each TLC glass plate was divided into 20 equal squares. Stock solution of each of the compound was made (1 mg/10 μL of dichloromethane), and 25 μL of this solution was spotted (2.5 mg of the compound), making sure that all of the spots were close to 3 mm in diameter.…”

Section: Methodsmentioning

confidence: 99%

“…The inhibition diameter was taken as an average of four measurements per TLC plate. The diameter of each inhibition zone was further determined in four different directions (0°, 45°, 90°, and 135°) as described in the literature. , The bioassay for each compound was done in triplicate.…”

Section: Methodsmentioning

confidence: 99%

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Synthesis, Antimicrobial Evaluation, and Structure–Activity Relationship of α-Pinene Derivatives

Dhar¹,

Chan²,

Cohen³

et al. 2014

J. Agric. Food Chem.

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Several (+)- and (-)-α-pinene derivatives were synthesized and evaluated for their antimicrobial activity toward Gram-positive bacteria Micrococcus luteus and Staphylococcus aureus, Gram-negative bacterium Escherichia coli, and the unicellular fungus Candida albicans using bioautographic assays. (+)-α-Pinene 1a showed modest activity against the test organisms, whereas (-)-α-pinene 1b showed no activity at the tested concentration. Of all the α-pinene derivatives evaluated, the β-lactam derivatives (10a and 10b) were the most antimicrobial. The increase in the antimicrobial activity of 10a compared to 1a ranged from nearly 3.5-fold (C. albicans) to 43-fold (S. aureus). The mean ± standard deviation for the zone of inhibition (mm) for 10a (C. albicans) was 31.9 ± 4.3 and that for S. aureus was 51.1 ± 2.9. Although (-)-α-pinene 1b was not active toward the test microorganisms, the corresponding β-lactam 10b, amino ester 13b, and amino alcohol 14b showed antimicrobial activity toward the test microorganisms. The increase in the antimicrobial activity of 10b compared to 1b ranged from 32-fold (S. aureus) to 73-fold (M. luteus). The mean ± standard deviation for the zone of inhibition (mm) for 10b (S. aureus) was 32.0 ± 0.60 and that for M. luteus was 73.2 ± 0.30.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Synthesis, Antimicrobial Evaluation, and Structure–Activity Relationship of α-Pinene Derivatives

Dhar¹,

Chan²,

Cohen³

et al. 2014

J. Agric. Food Chem.

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“…Comparison between the effect of citronellol, citronellal and citronellyl acetate, linalool and linallyl acetate, and geraniol and citral, indicate that hydroxyl group is important in the antibacterial activity and swarming inhibition of P. mirabilis by monoterpenes ( Table 1 ). In general, the antimicrobial activity of a compound increases with the presence of an oxygen containing functional group, indicating a relationship between structure and biological activity [ 25 , 26 ].…”

Section: Resultsmentioning

confidence: 99%

The Effect of Monoterpenes on Swarming Differentiation and Haemolysin Activity in Proteus mirabilis

et al. 2008

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Urinary tract infection by Proteus mirabilis depends on several virulence properties that are coordinately regulated with swarming differentiation. Here we report the antibacterial and anti-swarming effect of seventeen terpenoids, and the effect of sub-inhibitory concentrations of five selected terpenoids on swarming, biofilm formation and haemolysin activity. The results showed that all the terpenes evaluated, particularly oxygenated terpenoids, inhibited P. mirabilis with MIC values ranging between 3 and 10 mg/L. Moreover, citral, citronellol and geraniol effectively inhibit P. mirabilis swarming in a dose dependent manner, reducing swimming/swarming cell differentiation and haemolysin activity at 1/10 MIC concentration. The inhibition of P. mirabilis swarming and virulence factor expression by selected oxygenated terpenoids suggest that essential oils with high concentration of these compounds have the potential to be developed as products for preventing P. mirabilis infections.

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“…The antibacterial, antimicrobial, and antifungal activity of natural extracts containing monoterpenes are well known [1][2][3][4]. Among the monoterpenes identified in the extracts, two compounds, cis-verbenol (C 10 H 16 O) and verbenone (C 10 H 14 O), have been shown to be highly bioactive [5].…”

Section: Introductionmentioning

confidence: 99%

Optimization of a New Extraction Technique for Analysis of Verbenone and cis-Verbenol in Pine Seeds

Liazid

Barbero

Palma

et al. 2007

Chroma

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Results from a systematic study of the factors affecting extraction of cis-verbenol and verbenone from pine seeds are presented. Five extraction conditions were investigated: extraction solvent, method of extraction, extraction temperature, volume of solvent, and the ratio of the mass of sample to the amount of extraction solvent. The resulting optimized method uses magneticstirring-assisted extraction of pine seeds (5 g) with ethyl acetate (75 mL) for 20 min, at room temperature. RSDs were less than 5% for both compounds. GC-FID was used for quantification of cis-verbenol and verbenone in the extracts.

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Study of the Structural Changes on the Antimicrobial Activity of [3.1.1.]-Bicyclics

Cited by 5 publications

References 19 publications

Synthesis, Antimicrobial Evaluation, and Structure–Activity Relationship of α-Pinene Derivatives

Synthesis, Antimicrobial Evaluation, and Structure–Activity Relationship of α-Pinene Derivatives

The Effect of Monoterpenes on Swarming Differentiation and Haemolysin Activity in Proteus mirabilis

Optimization of a New Extraction Technique for Analysis of Verbenone and cis-Verbenol in Pine Seeds

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