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α- and β-Pinene
α- and β-pinene are well-known representatives of the monoterpenes group, and are found in many plants’ essential oils. A wide range of pharmacological activities have been reported, including antibiotic resistance modulation, anticoagulant, antitumor, antimicrobial, antimalarial, antioxidant, anti-inflammatory, anti-Leishmania, and analgesic effects.
2. Preclinical Pharmacological Activities of α- and β-Pinene
2.1. Antibiotic Resistance Modulation
2.2. Anticoagulative Activities
2.3. Antitumor Activity
2.4. Genomic Instability
2.5. Cytogenetic and Oxidative Effects
2.6. Gastroprotective Effect
2.7. Anxiolytic-Like Effects
2.8. Neuroprotective Activities
2.9. Cytoprotective Activity against H2O2-Stimulated Oxidative Stress
2.10. Inhibitory Effect on the Growth of Endocarditis Disease
3. Bioavailability of α-Pinene and β-Pinene
3.1. Dermal Application
|Inhalation (8 volunteers, with light exercise-50W) |
|α-pinene (+)||2 h 450, 225, or 10 mg/m3||Relative net uptake 59–62% *||tmax 120 min
cmax 20 µMol/L(for 450 mg/m3)
cmax 10 µMol/L(for 225 mg/m3)
(exposure concentration depended) * cmax 10 µMol/L
|0.001% In 30 min
4% of total uptake as cis and trans verbenol
|t1/2 (3 phases α, β, γ)
|α-pinene (−)||450 mg/m3||7.5%||cl21h
|β-pinene||450 mg/m3 *||Relative net uptake 66% *||cmax 3 µMol/L *||* 5.7%||* cl21h
|Dermal application in vitro , Ex vivo |
(concentration is not provided) for 27 h
|Papp 6.49 × 10−5 cm/s|
|100 mg/cm2 applied on 0.65 cm2 at 37 °C ¥||cmax 40 µg/cm2
tmax 15 min in SC
(concentration is not provided) for 27 h
|Papp 4.48 × 10−5 cm/s|
|100 mg/cm2 applied on 0.65 cm2 at 37 °C ¥||cmax 290 µg/cm2
tmax 60 min in SC
|Oral administration (four volunteers) |
|α-pinene||9 mg (66 µmol)||Unmetabolized state—not detected (<4 µg/L)||t1/2
|tmax 1.6 h
1–3 h Metabolites
MYR-1.5 h cVER and tVER-1.6 h
MYR-1.5%, cVER-5.6%, tVER-4.1%
|78% unknown elimination, which could be exhalation or first-pass metabolism|
3.3. Oral Administration
|S. No.||Source/Species||Model||Plant Portion||Method||Result||Ref|
|1||Sigma Aldrich||Campylobacter jejuni||-||Broth microdilution and ethidium bromide deposition||Modulation of antibiotic resistance, by reducing MIC value of ciprofloxacin, erythromycin, and triclosan, up to 512 times. α-pinene also affected antimicrobial efflux systems|||
|2||-||Nocardia sp. Strain (P18.3), Pseudomonas putida PX1 (NCIB 10684), Pseudomonas sp. strain PIN18 (NCIB 10687), and P. fluorescens NCIB 11671||-||Strains were cultured into agar slants with α-pinene (3 g/L in media), and strains growth was recorded||Nocardia sp. growth (P18.3) was not remarkable; Pseudomonas strains (NCIB 10684, 10687, and 11,671 and PL) increased promptly when α-pinene (0.3%, v/v) was added|||
|24||Citrus species||Propionibacterium acnes, Staphylococcus epidermidis||Peel EO||EO was isolated by hydrodistillation||EO demonstrated outstanding antibacterial properties against P. acnes and S. epidermidis|||
|26||Sigma-Aldrich||Escherichia coli, Micrococcus luteus, Staphylococcus aureus, and Candida albicans||-||Bioautographic method
MIC was measured
|(+)-α-pinene exhibited modest activity. (−)-α-pinene was unable to display any activity. α-pinene and β-lactams revealed the highest effects. Although (−)-α-pinene revealed no positive activity, the derivatives like β-lactam, amino ester, and amino alcohol exhibited antimicrobial effects|||
|28||Bursera morelensis||Candida albicans strains (ATCC 14065, ATCC 32354, donated strain, and CDBB-L-1003)||Stems (EO)||EO was extracted by hydrodistillation, and GC-MS was used to isolate compounds
Disc diffusion and survival curve assay were used
|Maximum antifungal activity was attributed to the EO and its constituent, namely, α-pinene. Minimum fungicidal concentration of EO was found to be 2 mg/mL. A slight reduction in C. albicans population was recorded after 12 h|||
|30||-||Staphylococcus aureus and Escherichia coli||-||Disc diffusion test, broth microdilution, and bacterial death kinetics||Inhibition halos of 11 and 12 mm for gram-positive and -negative strains were obtained at 160 µL/mL, respectively. At 1.25 and 2.5 µL/mL, (+)-α-pinene was able to eliminate bacterial colonies formation at one time of exposure of 2 h for E. coli strain|||
|31||Syzygium cumini||Swiss mice||Leaves (EO)||MTT assay
Cytotoxic effect on macrophages was determined; cells were exposed to α-pinene and tested against Leishmania
|Cytotoxic effect of α-pinene against promastigotes of Leishmania amazonensis was observed with different cell death percentages (93.7, 83.2, and 58.4%) at different concentrations (100, 50, and 25 mg/mL respectively)|||
|40||-||House fly (Musca domestica)||-||Y-tube and house flies were selected for this test||Solution with lowest concentration did not show significant differences in Y-tube arm choice. (1S)-(-)-α-pinene had maximum repellent efficiency for house flies when compared to (1R)-(+)-α-pinene|||
|45||Plectranthus barbatus||Malaria (Anophel es subpictus), dengue (Aedes albopictus), and Japanese encephalitis (Culex tritaeniorhynchus) mosquito vectors||EO (leaves)||GC and GC--MS were performed; larvicidal activity of EO (40, 80, 120, 160, and 200 µg/mL) and its constituents eugenol, α-pinene, and β-caryophyllene (12–100 µg/mL each) were determined by WHO methods. Mortality of larvae was measured at 24 h after exposure||EO showed substantial larvicidal effects with LC50 values of 84.20, 87.25, and 94.34 µg/mL for the selected mosquito species. For Anapheles subpictus, eugenol, α-pinene, and β-caryophyllene revealed larvicidal effects (LC50 = 25.45, 32.09, and 41.66 μg/mL), followed by Aedes albopictus (LC50 = 28.14, 34.09, and 44.77 μg/mL) and Culex tritaenior hynchus (LC50 = 30.80, 36.75, and 48.17 μg/mL, respectively)|||
|27||-||Klebsiella pneumoniae, Enterobacter aerogenes, S. aureus, S. epidermidis, and Candida albicans||-||25 3-cyanopyridine compounds of β-pinene were prepared; MIC value was recorded using serial two-fold dilution method||MICs values of all derivatives ranged from 15.6 to 125 mg/l|||
|29||-||Candida spp.||-||MIC and MFC values and microbial death curve after treatment with (+)-β-pinene enantiomers||MIC values ranged from <56.25–1800 µmol/L (+)-β-pinene. After ergosterol addition, MIC value of (+)-β-pinene was not altered, but was altered with sorbitol addition. (+)-β-pinene displayed anti-biofilm activity against multiple Candida species|||
|α- and β-pinene|
|22||Dep. Pharmaceutical Sciences, Ponta Grossa, Brazil||Gram-positive bacteria (Staphylococcus aureus, S. epidermidis, S. pneumoniae, and S. pyogenes)||-||MIC value, viable cells count||All studied bacterial strains were sensitive to α- and β-pinene. MIC values ranged from 5 (α-pinene x S. epidermidis SSI 1; ATCC 12228; S. pyogenes ATCC 19,615; and S. pneumoniae) to 40 μL/mL (β-pinene x S. epidermidis ATCC 12228). Few bacterial strains were resistant antibiotics, mainly gentamicin. S. aureus was resistant to α- and β-pinene|||
|23||Sigma-Aldrich||Antimicrobial: Escherichia coli (ATCC 11775, Staphylococcus aureus (ATCC 25923), Bacillus cereus (ATCC 11778), and Candida albicans (ATCC 10231).
Antimalarial: Plasmodium falciparum (FCR-3)
|-||Disc diffusion method. MIC was investigated. Antimalarial properties were analyzed using the tritiated hypoxanthine incorporation assay||(+)-β-pinene was approximately two to 12 times more effective as compared to (+)-α-pinene against both gram-positive and negative bacteria, as well as C. albicans. (+)-α-pinene shows 250-fold more antimalarial activity than (+)-β-pinene|||
|25||Sigma-Aldrich||Candida albicans, Cryptococcus neoformans,
Rhizopus oryzae, and methicillin-resistant Staphylococcus aureus (MRSA)
|-||Two-fold serial dilution method was used to evaluate MIC for all the strains||MIC values of α- and β-pinene enantiomers were found to be from 117 to 6250 µg/mL. C. albicans exhibited higher sensitivity to α- and β-pinene enantiomers than MRSA. Positive enantiomers possess capability to kill 100% of C. albicans in 60 min., and 6 h was required for total killing of MRSA|||
The entry is from 10.3390/biom9110738
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