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Biological activities of ?-pinene and ?-pinene enantiomers.

ABSTRACT: The antimicrobial activities of the isomers and enantiomers of pinene were evaluated against bacterial and fungal cells. The agar diffusion test showed that only the positive enantiomers of the ?- and ?-isomers of pinene were active. The minimal inhibitory concentration (MIC) and minimal microbicidal concentration (MMC) of these monoterpenes were also determined, confirming that the positive enantiomers exhibited microbicidal activity against all fungi and bacteria tested with MICs ranging from 117 to 4,150 ?g/mL. However, no antimicrobial activity was detected with the negative enantiomers up to 20 mg/mL. Time-kill curves showed that (+)-?-pinene and (+)-?-pinene were highly toxic to Candida albicans, killing 100% of inoculum within 60 min. By contrast, the bactericidal effect occurred after 6 h in methicillin-resistant Staphylococcus aureus (MRSA). In combination with commercial antimicrobials, ciprofloxacin plus (+)-?-pinene or (+)-?-pinene presented synergistic activity against MRSA whereas an indifferent effect against all fungi was detected when amphotericin B was combined with the positive enantiomers of pinene. The potential of (+)-?-pinene and (+)-?-pinene to inhibit phospholipase and esterase activities was also evaluated, and the best inhibition results were obtained with Cryptococcus neoformans. C. albicans biofilm formation was prevented with the MIC concentration of (+)-?-pinene and twice the MIC value of (+)-?-pinene. Finally, the cytotoxicity of the positive enantiomers of pinene to murine macrophages was evaluated, and 250 ?g/mL of (+)-?-pinene and (+)-?-pinene reduced the cell viability to 66.8% and 57.7%, respectively.

SUBMITTER: Rivas da Silva AC

PROVIDER: S-EPMC6268778 | biostudies-literature | 2012 May

REPOSITORIES: biostudies-literature

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Biological activities of α-pinene and β-pinene enantiomers.

Rivas da Silva Ana Cristina AC Lopes Paula Monteiro PM Barros de Azevedo Mariana Maria MM Costa Danielle Cristina Machado DC Alviano Celuta Sales CS Alviano Daniela Sales DS

Molecules (Basel, Switzerland) 20120525 6

The antimicrobial activities of the isomers and enantiomers of pinene were evaluated against bacterial and fungal cells. The agar diffusion test showed that only the positive enantiomers of the α- and β-isomers of pinene were active. The minimal inhibitory concentration (MIC) and minimal microbicidal concentration (MMC) of these monoterpenes were also determined, confirming that the positive enantiomers exhibited microbicidal activity against all fungi and bacteria tested with MICs ranging from ...[more]

PMID: 22634841

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Project description:The formation of atmospheric cloud droplets due to secondary organic aerosol (SOA) particles is important for quantifying the Earth's radiative balance under future, possibly warmer, climates, yet is only poorly understood. While cloud activation may be parametrized using the surface tension depression that coincides with surfactant partitioning to the gas-droplet interface, the extent to which cloud activation is influenced by both the chemical structure and reactivity of the individual molecules comprising this surfactant pool is largely unknown. We report herein considerable differences in the surface tension depression of aqueous pendant droplets that contain synthetically prepared ozonolysis products derived from α-pinene and β-caryophyllene, the most abundant of the monoterpenes and sesquiterpenes, respectively, that are emitted over the planet's vast forest ecosystems. Oxidation products derived from β-caryophyllene were found to exhibit significantly higher surface activity than those prepared from α-pinene, with the critical supersaturation required for cloud droplet activation reduced by 50% for β-caryophyllene aldehyde at 1 mM. These considerable reductions in the critical supersaturation were found to coincide with free energies of adsorption that exceed ∼25 kJ/mol, or just one hydrogen bond equivalent, depending on the ammonium sulfate and oxidation product concentration in the solution. Additional experiments showed that aldehyde-containing oxidation products exist in equilibrium with hydrated forms in aqueous solution, which may modulate their bulk solubility and surface activity. Equilibration time scales on the order of 10-5 to 10-4 s calculated for micrometer-sized aerosol particles indicate instantaneous surface tension depression in the activation processes leading to cloud formation in the atmosphere. Our findings highlight the underlying importance of molecular structure and reactivity when considering cloud condensation activity in the presence of SOA particles.

Project description:Recent ambient atmospheric measurements have detected highly oxygenated organic molecules (HOMs) at many sites and are a consequence of autoxidation processes occurring at ambient temperatures. Monoterpenes in particular have a propensity to autoxidize although they exhibit a wide range of HOM yields, which may be due to a variety of reasons including reactions with different oxidants like OH and O3, differing hydrogen (H) atom transfer or peroxy radical cyclization rates, numbers of available reaction pathways, and/or energy loss processes for activated HO-monoterpene or O3-monoterpene adducts. In this work, the autoxidation mechanisms of (+)-α-pinene, (+)-β-pinene, and (+)-limonene following initial OH oxidation and three successive O2 additions are examined using density functional theory (DFT) to understand what accounts for the disparity. Rates of different potential autoxidation pathways initiated by OH addition or abstraction reactions are quantified using transition-state theory (TST) and master equation approaches using the lowest-energy conformers. OH abstraction reactions do not appreciably influence HOM production in the pinenes and limit autoxidation for limonene because the subsequent autoxidation reactions are slow while OH addition reactions are found to be the main route to HOMs for all three monoterpenes. Generally, faster autoxidation rates are computed in later unimolecular reactions that produce RO7 radicals after OH addition (∼10 s-1 or greater) than rates for RO5 peroxy radical production (0.2-7 s-1). Mechanistic pathways that form RO7 peroxy radicals are similar for all three monoterpenes with a particular bicyclo RO7 radical involving a five-membered peroxide ring being favored for all three monoterpenes. The molar yields of RO7 radicals are 4.6% (+10.0/-2.4), 3.8% (+9.1/-2.6), and 7.6% (+13.1/-4.9) for α-pinene, β-pinene, and limonene, respectively, at 298 K and 1 ppb of NO and only significantly decline at NO concentrations exceeding 10 ppb. The higher yield for limonene relative to the pinenes is predominantly a consequence of the initial oxidation step: OH adducts of the bicyclic pinenes have to use the excess energy after OH addition to break one of the rings and make the molecule more flexible for autoxidation although this process is inefficient, while one of the prominent OH adducts for monocyclic limonene does not have to do this and may add O2 immediately before autoxidizing further. These insights may be used to guide a better representation of these processes in atmospheric models because they affect particulate matter (PM), NOx, and ozone concentrations via enhanced production of low-volatility species, less early-generation NOx cycling, and altered organic nitrate production.

Dataset Information

Biological activities of ?-pinene and ?-pinene enantiomers.

Publications

Biological activities of α-pinene and β-pinene enantiomers.

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