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

Abstract

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.

Composition and Antimicrobial Activity of the Essential Oils of Three Plant Species from the Sabana of Bogota (Colombia): Myrcianthes leucoxyla, Vallea stipularis and Phyllanthus salviifolius

“…It is present in EOs of various plant species and has been recognized for its potent antimicrobial activity. Recent studies have shown that it effectively inhibits P450 2B [21]. In addition, this compound complies with the criteria described by Lipinsky related to the affinity for biological membranes and absorption, and therefore, related to its activity: it has a molecular weight less than 500 (136), has an index of lipophilicity (logP) equal to 4.3 and a number of groups which can aureus, but the results differ in the activity against E. coli.…”

Chemical composition and antimicrobial activity against food‐related microorganisms of different essential oils from Lebanon

“…So, α‐pinene which is the most abundant component in J . excelsa essential oil might play an important role in the antifungal activity of the oil (Dhar et al, ). C .…”

“…While J. excelsa EO exhibited only a moderate antimicrobial activity against the two S. cerevisiae yeasts strains A9 (MIC 2.5 μL/mL) and EC1118 (MIC 5 μL/mL). So, α-pinene which is the most abundant component in J. excelsa essential oil might play an important role in the antifungal activity of the oil(Dhar et al, 2014).C. zeylanicum, C. capitatus, and O. syriacum EOs showed a significant antimicrobial activity against yeasts strains with MIC values ranging from 0.039 to 0.625 μL/mL.…”

Spent cumin seeds generated from ayurvedic industry as a source of bioactive compounds for nutraceutical/functional food applications

“…Cumin EO is reported to have antibacterial and antifungal activities (Chaudhary et al, ; Nisha et al, ). The antimicrobial activity of EO from cumin can be correlated to its chemical composition as β‐pinene, o ‐cymene, δ‐carene, and cuminaldehyde, p ‐cymen‐7‐ol, the major compounds in EO from SC and FC, are reported to possess antimicrobial activities (Custodio, Ribeiro, Silva, Machado, & Sousa, ; Dhar et al, ).…”