Natural terpenes: Self-assembly and membrane partitioning

Turina, A.del V.; Nolan, M.V.; Zygadlo, J.A.; Perillo, M.A.

doi:10.1016/j.bpc.2006.02.007

Cited by 305Lipid Membrane Structure and BehaviorSurfactants and Colloidal SystemsEssential Oils and Antimicrobial Activity

Natural terpenes: Self-assembly and membrane partitioning

Turina, A.del V., Nolan, M.V., Zygadlo, J.A., Perillo, M.A.·2006·Biophysical Chemistry

DOI 10.1016/j.bpc.2006.02.007

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Abstract

Monoterpenes (MTs) are highly hydrophobic substances present in essential oils. They cover a wide spectrum of biological effects with a membrane interaction as a common point. Here we studied the surface activity of camphor, cineole, thymol, menthol and geraniol, and their ability to reach and incorporate into model membranes affecting some features of their dynamic organization. All the MTs studied self-aggregated in water with critical micellar concentrations (CMC) between 3 and 8 microM. Their octanol-water and membrane-water partition coefficients were correlated with one another. They all penetrated in monomolecular layers of dipalmitoyl-phosphatildylcholine at the air-water interface, even at surface pressures (pi) above the equilibrium lateral pressure of bilayers; thymol exhibited the highest (61.3 mN/m) and camphor the lowest (37 mN/m) pi(cut-off) value. They affected the self-aggregation of Triton X-100, increasing its CMC from 0.16 mM in the absence of MTs up to 0.68 mM (e.g. for geraniol), and the topology of sPC vesicles, increasing its surface curvature, suggesting their location at the polar head group region of the membrane. The latter was supported by their ability to increase differentially the polarity of the membrane environment sensed by two electrochromic dyes. Dipole moment values (between 1.224 and 2.523 D) and solvation areas (between 80 and 97 A(2)) were calculated from their energy-minimized structures. The relative contribution of each experimental, theoretical and structural property to determine MTs' effects on membrane dynamics were evaluated by a principal component analysis.

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At low levels of thymol, the membrane can adapt its lipid profile to maintain membrane function and structure.
“At low levels of thymol, the membrane can adapt its lipid profile to maintain membrane function and structure [29].”
From Effect of essential oils on pathogenic bacteria (2013) · cites this paper as [29]
Inhibiting electron transport for energy production and disrupting the proton motive force, protein translocation and synthesis of cellular components are physiological changes that can result in cell lysis and death.
“Inhibiting electron transport for energy production and disrupting the proton motive force, protein translocation and synthesis of cellular components are all physiological changes that can result in cell lysis and death [19,29].”
From Effect of essential oils on pathogenic bacteria (2013) · cites this paper as [29]

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Membrane Disruption Properties of Essential Oils—A Double-Edged Sword?
Yap, P. S. X., Yusoff, K., Lim, S. E., Chong, C. M., & Lai, K. (2021) · Processes · doi:10.3390/pr9040595 · Cited by 145 · see citing works
“For instance, thymol was found to be able to induce membrane alteration through integration with polar head-groups of the lipid bilayer; however, at low concentrations, the adapted membrane lipid compositions can still regulate and maintain membrane fluidity and function [12,28].”
Background
Essential Oils
Hanif, M. A., Nisar, S., Khan, G. S., Mushtaq, Z., & Zubair, M. (2019) · Springer eBooks · doi:10.1007/978-3-030-16546-8_1 · Cited by 142 · see citing works
Effects of Mentha suaveolens Essential Oil Alone or in Combination with Other Drugs in Candida albicans
Stringaro, A., Vavala, E., Colone, M., Pepi, F., Mignogna, G., Garzoli, S., Cecchetti, S., Ragno, R., & Angiolella, L. (2014) · Evidence-based Complementary and Alternative Medicine · doi:10.1155/2014/125904 · Cited by 129 · see citing works
“The monoterpenes act by disrupting microbial cytoplasmic membrane, which thus loses its high impermeability for protons and bigger ions; if disturbance of membrane integrity occurs, then its functions are compromised not only as a barrier but also as a matrix for enzymes and as an energy transducer [32].”
Background
Emerging trends in pectin extraction and its anti-microbial functionalization using natural bioactives for application in food packaging
Kumar, M., Tomar, M., Saurabh, V., Mahajan, T. R., Punia, S., Contreras, M. D. M., Rudra, S. G., Kaur, C., & Kennedy, J. F. (2020) · Trends in Food Science & Technology · doi:10.1016/j.tifs.2020.09.009 · Cited by 133 · see citing works
Study of the release of limonene present in chitosan films enriched with bergamot oil in food simulants
Sánchez‐González, L., Cháfer, M., González‐Martínez, C., Chiralt, A., & Desobry, S. (2011) · Journal of Food Engineering · doi:10.1016/j.jfoodeng.2011.02.016 · Cited by 123 · see citing works
Geraniol Pharmacokinetics, Bioavailability and Its Multiple Effects on the Liver Antioxidant and Xenobiotic-Metabolizing Enzymes
Pavan, B., Dalpiaz, A., Marani, L., Beggiato, S., Ferraro, L., Canistro, D., Paolini, M., Vivarelli, F., Valerii, M. C., Comparone, A., et al. (2018) · Frontiers in Pharmacology · doi:10.3389/fphar.2018.00018 · Cited by 115 · see citing works
“Indeed, the geometry and the hydrophilic/hydrophobic compensation of its molecule would allow geraniol a higher thermodynamic stability and permanence in a membrane bilayer model than other monoterpenes (Turina et al., 2006).”
Background
Therapeutic potentials of bioactive compounds from mango fruit wastes
Asif, A., Farooq, U., Akram, K., Hayat, Z., Shafi, A., Sarfraz, F., Sidhu, M. A. I., Rehman, H.-U., & Aftab, S. (2016) · Trends in Food Science & Technology · doi:10.1016/j.tifs.2016.05.004 · Cited by 113 · see citing works
Agro-industrial wastes as sources of bioactive compounds for food and fermentation industries
Shirahigue, L. D., & Ceccato‐Antonini, S. R. (2020) · Ciência Rural · doi:10.1590/0103-8478cr20190857 · Cited by 116 · see citing works
Antioxidant and antibacterial activity of essential oil and extracts of bay laurel Laurus nobilis Linnaeus (Lauraceae) from Portugal
Ramos, C., Teixeira, B., Batista, I., Matos, O., Serrano, C., Neng, N. R., Nogueira, J. M. F., Nunes, M. L., & Marques, A. (2011) · Natural Product Research · doi:10.1080/14786419.2010.531478 · Cited by 112 · see citing works
“These six lipophilic compounds are able to enter the cell membranes of microorganisms and permeate them, through the disruption of the polysaccharide, fatty acid and phospholipid structures, and they promote the loss of ions by collapsing the proton pump and depleting the adenosine-5′-triphosphate pool (Turina, Nolan,…”
Background
Cellular and Molecular Targets of Menthol Actions
Öz, M., Nebrisi, E. E., Yang, K. S., Howarth, F. C., & Kury, L. T. A. (2017) · Frontiers in Pharmacology · doi:10.3389/fphar.2017.00472 · Cited by 108 · see citing works
“It is not completely soluble in water (431 mg/L at 20 ◦ C), but freely soluble in chloroform, diethyl ether, and alcohol (Kamatou et al., 2013) with Log octanol/water value of 3.4, indicating that menthol is a lipophilic compound capable of interacting with membranes (Turina et al., 2006).”
Influential
Investigation of the Antifungal Activity and Mode of Action of Thymus vulgaris, Citrus limonum, Pelargonium graveolens, Cinnamomum cassia, Ocimum basilicum, and Eugenia caryophyllus Essential Oils
Gucwa, K., Milewski, S., Dymerski, T., & Szweda, P. (2018) · Molecules · doi:10.3390/molecules23051116 · Cited by 106 · see citing works
“The antimicrobial effect may be linked to reduced membrane potentials, the disruption of proton pumps, and the depletion of the ATP [14].”
Background
Antimicrobial and antioxidant activity of essential oil and different plant extracts of Psidium cattleianum Sabine
Scur, M. C., Pinto, F. G. D. S., Pandini, J. A., da Costa, W. F., Leite, C. W., & Temponi, L. G. (2016) · Brazilian Journal of Biology · doi:10.1590/1519-6984.13714 · Cited by 104 · see citing works
“However, Turina et al. (2006) reported that owing the high hydrophobicity of monoterpenes, their toxic effects on the bacterial cell membrane result in its expansion, fluidity, and permeability, in addition to causing inhibition of respiration and change in the process of ions transport.”
Background
Liposomes loaded with Salvia triloba and Rosmarinus officinalis essential oils: In vitro assessment of antioxidant, antiinflammatory and antibacterial activities
Risaliti, L., Kehagia, A., Daoultzi, E., Lazari, D. M., Bergonzi, M. C., Vergkizi, S., Hadjipavlou‐Litina, D., & Bilia, A. R. (2019) · Journal of Drug Delivery Science and Technology · doi:10.1016/j.jddst.2019.03.034 · Cited by 104 · see citing works
Antioxidant and antimicrobial poly-ε-caprolactone nanoparticles loaded with Cymbopogon martinii essential oil
Jummes, B., Sganzerla, W. G., da Rosa, C. G., Noronha, C. M., Nunes, M. R., Bertoldi, F. C., & Barreto, P. L. M. (2020) · Biocatalysis and Agricultural Biotechnology · doi:10.1016/j.bcab.2020.101499 · Cited by 97 · see citing works
Antibacterial and anti-biofilm activities of cinnamaldehyde against S. epidermidis
Albano, M., Crulhas, B. P., Alves, F. C. B., Pereira, A. F. M., Andrade, B. F. M. T., Barbosa, L. N., Furlanetto, A., Lyra, L. P. D. S., Rall, V. L. M., & Júnior, A. F. (2018) · Microbial Pathogenesis · doi:10.1016/j.micpath.2018.11.009 · Cited by 93 · see citing works
Nasal administration of nanoencapsulated geraniol/ursodeoxycholic acid conjugate: Towards a new approach for the management of Parkinson's disease
de Oliveira, E. R., Truzzi, E., Ferraro, L., Fogagnolo, M., Pavan, B., Beggiato, S., Rustichelli, C., Maretti, E., Lima, E. M., Leo, E., et al. (2020) · Journal of Controlled Release · doi:10.1016/j.jconrel.2020.02.033 · Cited by 93 · see citing works
Effects of monoterpenes on ion channels of excitable cells
Öz, M., Lozon, Y., Sultan, A. M., Yang, K. S., & Galadari, S. (2015) · Pharmacology & Therapeutics · doi:10.1016/j.pharmthera.2015.05.006 · Cited by 97 · see citing works
“Therefo it is not surprising that several physicochemical properties of lipid bilayer membranes are significantly affected by these compounds as a result of their partitioninginto membranes (Sánchez et al., 2004; Turina et al., 2006; Zunino et al., 2011).”
Background
Antioxidant and Antimicrobial Activities of Chemically-Characterized Essential Oil from Artemisia aragonensis Lam. against Drug-Resistant Microbes
Chebbac, K., Ghneim, H. K., Moussaoui, A. E., Bourhia, M., Barnossi, A. E., Ouaritini, Z. B., Salamatullah, A. M., Alzahrani, A. A., Aboul‐Soud, M. A. M., Giesy, J. P., et al. (2022) · Molecules · doi:10.3390/molecules27031136 · Cited by 81 · see citing works
“Reduced membrane potentials, interruption of proton pumps and ATP exhaustion may all contribute to the observed antimicrobial activity [64].”
In vitro activity of natural phenolic compounds against fluconazole-resistant Candida species: a quantitative structure-activity relationship analysis
Gallucci, M. N., Carezzano, M. E., Oliva, M. M., Demo, M. S., Pizzolitto, R. P., Zunino, M. P., Zygadlo, J. A., & Dambolena, J. S. (2014) · Journal of Applied Microbiology · doi:10.1111/jam.12432 · Cited by 81 · see citing works
“The presence of the Log P descriptor in the mathematical models suggested that part of the antifungal activity of the phenolic compounds can be explained by their interaction with the plasma membrane (Turina et al. 2006; Cristani et al. 2007; Khan et al. 2011; Zunino et al. 2011).”
Background
Role of sepiolite in the release of active compounds from gelatin–egg white films
Giménez, B., Gómez-Guillén, M. C., López-Caballero, M. E., Gómez‐Estaca, J., & Montero, P. (2011) · Food Hydrocolloids · doi:10.1016/j.foodhyd.2011.09.003 · Cited by 81 · see citing works
Efficacy of chitosan films with basil essential oil: perspectives in food packaging
Hemalatha, T., Umamaheswari, T., Senthil, R., Krithiga, G., & Anbukkarasi, K. (2017) · Journal of Food Measurement & Characterization · doi:10.1007/s11694-017-9601-7 · Cited by 77 · see citing works
Efficacy of thymol against Echinococcus granulosus protoscoleces
Elissondo, M. C., Albani, C. M., Gende, L. B., Eguaras, M. J., & Denegri, G. M. (2007) · Parasitology International · doi:10.1016/j.parint.2007.12.005 · Cited by 74 · see citing works
Thyme essential oil loaded in nanocochleates: Encapsulation efficiency, in vitro release study and antioxidant activity
Asprea, M., Leto, I., Bergonzi, M. C., & Bilia, A. R. (2016) · LWT · doi:10.1016/j.lwt.2016.12.006 · Cited by 74 · see citing works
Enhancement of the antibiotic activity of aminoglycosides by alpha-tocopherol and other cholesterol derivates
Andrade, J. C., Morais‐Braga, M. F. B., Guedes, G. M. D. M., Tintino, S. R., de Freitas, M. A., de Menezes, I. R. A., & Coutinho, H. D. M. (2014) · Biomedicine & Pharmacotherapy · doi:10.1016/j.biopha.2014.10.011 · Cited by 73 · see citing works
“The composition of lipophilic substances such as alphatocopherol allow perturbations in the bacterial membrane, resulting in damage to essential elements for the integrity of the membrane such as: reduction in membrane potential and loss of ions, cytochrome C, proteins and radicals, followed by the collapse of proton…”
Background
Lithocholic acid and derivatives: Antibacterial activity
do Nascimento, P. G. G., Lemos, T. L. G., de Almeida, M. C. S., Souza, J. M. O., Bizerra, A. M. C., Santiago, G. M. P., da Costa, J. G. M., & Coutinho, H. D. M. (2015) · Steroids · doi:10.1016/j.steroids.2015.07.007 · Cited by 71 · see citing works
Edible Coatings Enriched with Essential Oils and their Compounds for Fresh and Fresh-cut Fruit
Antunes, M. D. C., Gago, C., Cavaco, A. M., & Miguel, M. G. (2012) · Recent Patents on Food Nutrition & Agriculture · doi:10.2174/2212798411204020114 · Cited by 71 · see citing works
“Other studies have demonstrated that some components are able to act on the cytoplasmic membrane proteins or to inhibit the activity of some enzymes involved in cell metabolic pathways [37-41].”
Background
Mechanism of Action of Thymol on Cell Membranes Investigated through Lipid Langmuir Monolayers at the Air–Water Interface and Molecular Simulation
Ferreira, J. V. N., Capello, T. M., Siqueira, L. J. A., Lago, J. H. G., & Caseli, L. (2016) · Langmuir · doi:10.1021/acs.langmuir.6b00600 · Cited by 70 · see citing works
Antimicrobial mechanism of nanocellulose composite packaging incorporated with essential oils
Firmanda, A., Fahma, F., Warsiki, E., Syamsu, K., Arnata, I. W., Sartika, D., Suryanegara, L., Qanytah, & Suyanto, A. (2023) · Food Control · doi:10.1016/j.foodcont.2023.109617 · Cited by 69 · see citing works
Essential oils from the genus Thymus as antimicrobial food preservatives: Progress in their use as nanoemulsions-a new paradigm
Pandey, A. K., Chávez‐González, M. L., Sanches-Silva, A. T., & Singh, P. (2021) · Trends in Food Science & Technology · doi:10.1016/j.tifs.2021.02.076 · Cited by 67 · see citing works
Antimicrobial activity of essential oils against Staphylococcus aureus biofilms
Vázquez‐Sánchez, D., Cabo, M. L., & Rodríguez-Herrera, J. J. (2014) · Food Science and Technology International · doi:10.1177/1082013214553996 · Cited by 67 · see citing works
“Previously, bacterial adaptation to individual active compounds of EOs (e.g. carvacrol, thymol, camphor or cineole) had been detected (Di-Pasqua et al., 2010; Turina et al., 2006; Ultee et al., 2000), but not to crude EOs (including thyme oil).”
Background
Microemulsion systems containing bioactive natural oils: an overview on the state of the art
Júnior, F. H. X., Vauthier, C., Morais, A. R. D. V., Alencar, É. D. N., & do Egito, E. S. T. (2016) · Drug Development and Industrial Pharmacy · doi:10.1080/03639045.2016.1235186 · Cited by 65 · see citing works
Applications of Essential Oils as Antibacterial Agents in Minimally Processed Fruits and Vegetables—A Review
Santos, M. I., Marques, C. F., Mota, J., Pedroso, L., & Lima, A. (2022) · Microorganisms · doi:10.3390/microorganisms10040760 · Cited by 65 · see citing works
Chemical Characteristics, Antimicrobial, and Cytotoxic Activities of the Essential Oil of Egyptian Cinnamomum glanduliferum Bark
Taha, S. M., & Eldahshan, O. A. (2017) · Chemistry & Biodiversity · doi:10.1002/cbdv.201600443 · Cited by 66 · see citing works
Menadione (vitamin K) enhances the antibiotic activity of drugs by cell membrane permeabilization mechanism
Andrade, J. C., Morais‐Braga, M. F. B., Guedes, G. M. D. M., Tintino, S. R., de Freitas, M. A., Quintans‐Júnior, L. J., de Menezes, I. R. A., & Coutinho, H. D. M. (2015) · Saudi Journal of Biological Sciences · doi:10.1016/j.sjbs.2015.09.004 · Cited by 64 · see citing works
“Lipophilic substances and menadione cause disturbances in the bacterial membrane, resulting in damage of the fundamental elements needed for membrane integrity, such as reduced membrane potential and loss of ions, cytochrome C, proteins and radicals, followed by the collapse of the proton pump and ATP depletion (Sikke…”
Background
Essential Oils: Chemical Composition and Diverse Biological Activities : A Comprehensive Review
Miri, Y. B. (2025) · Natural Product Communications · doi:10.1177/1934578x241311790 · Cited by 62 · see citing works
“74 These ﬁ ndings highlight the multifaceted mechanisms by which EOs exert their antibacterial effects, offering potential as alternative antimicrobial agents, particularly in the face of rising antibiotic resistance.”
Potential Effects of Geraniol on Cancer and Inflammation-Related Diseases: A Review of the Recent Research Findings
Ammar, R. B. (2023) · Molecules · doi:10.3390/molecules28093669 · Cited by 60 · see citing works
Eugenol-inhibited root growth in Avena fatua involves ROS-mediated oxidative damage
Ahuja, N., Singh, H. P., Batish, D. R., & Kohli, R. K. (2014) · Pesticide Biochemistry and Physiology · doi:10.1016/j.pestbp.2014.11.012 · Cited by 58 · see citing works
“Monoterpenes, being lipophilic, penetrate the cell membrane, change their fluidity and induce expansion resulting in the disruption of the membrane and hence ion leakage [40].”
Background
Bioactivity and health effects of garlic essential oil: A review
Huang, L., Liu, Z., Wang, J., Fu, J., Jia, Y., Ji, L., & Wang, T. (2023) · Food Science & Nutrition · doi:10.1002/fsn3.3253 · Cited by 59 · see citing works
“Plant essential oil can also play its antifungal role by destroying mitochondrial membranes and interfering with the electron transport system (de Turina et al., 2006).”
Background
Enhancement of aminoglycosides and β-lactams antibiotic activity by essential oil of Lippia sidoides Cham. and the Thymol
Veras, H. N. H., Rodrigues, F. F. G., Botelho, M. A., de Menezes, I. R. A., Coutinho, H. D. M., & da Costa, J. G. M. (2013) · Arabian Journal of Chemistry · doi:10.1016/j.arabjc.2013.10.030 · Cited by 58 · see citing works
Antibacterial activities, chemical constitutes and acute toxicity of Egyptian Origanum majorana L., Peganum harmala L. and Salvia officinalis L. essential oils
Selim, S., Abdel-Aziz, M., Mashait, M. S., & Warrad, M. (2013) · African Journal of Pharmacy and Pharmacology · doi:10.5897/ajpp2013.3518 · Cited by 58 · see citing works
Carvacrol and 1,8-cineole alone or in combination at sublethal concentrations induce changes in the cell morphology and membrane permeability of Pseudomonas fluorescens in a vegetable-based broth
de Sousa, J. P., Torres, R. D. A., de Azerêdo, G. A., Figueiredo, R. C. B. Q., Vasconcelos, M. A. D. S., & de Souza, E. L. (2012) · International Journal of Food Microbiology · doi:10.1016/j.ijfoodmicro.2012.06.008 · Cited by 55 · see citing works
Current Insights on the Role of Terpenoids as Anticancer Agents: A Perspective on Cancer Prevention and Treatment
Ansari, I. A., & Akhtar, M. S. (2019) · Springer eBooks · doi:10.1007/978-981-13-7205-6_3 · Cited by 55 · see citing works
Effect of Vitamin K3 Inhibiting the Function of NorA Efflux Pump and Its Gene Expression on Staphylococcus aureus
Tintino, S. R., de Souza, V. C. A., da Silva, J. M. A., Oliveira–Tintino, C. D. D. M., Pereira, P. S., Leal‐Balbino, T. C., Pereira‐Neves, A., Siqueira-Júnior, J. P., da Costa, J. G. M., Rodrigues, F. F. G., et al. (2020) · Membranes · doi:10.3390/membranes10060130 · Cited by 53 · see citing works
“It is known in the literature that fat-soluble substances can induce changes to the membranes, resulting in change in membrane morphophysiology and cause damage, such as: reduced membrane potential as well as ion; cytochrome C; protein and radicals loss, and subsequently collapse of the proton pump with ATP depletion…”
Background
Antibacterial Activity of Subtilosin Alone and Combined with Curcumin, Poly-Lysine and Zinc Lactate Against Listeria monocytogenes Strains
Amrouche, T., Noll, K. S., Wang, Y., Huang, Q., & Chikindas, M. L. (2010) · Probiotics and Antimicrobial Proteins · doi:10.1007/s12602-010-9042-7 · Cited by 52 · see citing works
“Toxic effects on membrane structure and function have been generally used to explain the antimicrobial action of some phytochemicals [6, 11, 38]; however, the specific mechanisms involved in the antimicrobial action of curcumin remain poorly characterized.”
Background
Comparative studies on properties and antioxidative activity of fish skin gelatin films incorporated with essential oils from various sources
Tongnuanchan, P., Benjakul, S., & Prodpran, T. (2014) · International aquatic research. · doi:10.1007/s40071-014-0062-x · Cited by 50 · see citing works
“Monoterpenes (C10) and sesquiterpenes (C15) are highly hydrophobic substances found in essential oils, in which the content varied with types of essential oils (Turina et al. 2006).”
Background
Dietary Geraniol by Oral or Enema Administration Strongly Reduces Dysbiosis and Systemic Inflammation in Dextran Sulfate Sodium-Treated Mice
Fazio, L. D., Spisni, E., Cavazza, E., Strillacci, A., Candela, M., Centanni, M., Ricci, C., Rizzello, F., Campieri, M., & Valerii, M. C. (2016) · Frontiers in Pharmacology · doi:10.3389/fphar.2016.00038 · Cited by 50 · see citing works
Stable, Monodisperse, and Highly Cell-Permeating Nanocochleates from Natural Soy Lecithin Liposomes
Asprea, M., Tatini, F., Piazzini, V., Rossi, F., Bergonzi, M. C., & Bilia, A. R. (2019) · Pharmaceutics · doi:10.3390/pharmaceutics11010034 · Cited by 50 · see citing works
“This is typical of small terpenes, which are able to decrease the size of lipid nanocarriers by forcing the PC structure to increase its surface curvature [30].”
Background
In Vitro Synergistic Activities of Essential Oils and Surfactants in Combination with Cosmetic Preservatives Against Pseudomonas aeruginosa and Staphylococcus aureus
Patrone, V., Campana, R., Vittoria, E., & Baffone, W. (2009) · Current Microbiology · doi:10.1007/s00284-009-9531-7 · Cited by 50 · see citing works
“The antimicrobial properties of essential oils are attributed to the presence of lipophilic compounds as terpenoids and phenolics which disturb the integrity of the cytoplasmic membrane with leakage of vital intracellular constitutes or impairment of bacterial enzyme systems [3, 15].”
Background
Essential oils from 9 exotic and endemic medicinal plants from Mauritius shows in vitro antibacterial and antibiotic potentiating activities
Jugreet, S., & Mahomoodally, M. F. (2020) · South African Journal of Botany · doi:10.1016/j.sajb.2020.05.001 · Cited by 49 · see citing works
In vitro activity of Carvacrol against titanium-adherent oral biofilms and planktonic cultures
Ciandrini, E., Campana, R., Federici, S., Manti, A., Battistelli, M., Falcieri, E., Papa, S., & Baffone, W. (2014) · Clinical Oral Investigations · doi:10.1007/s00784-013-1179-9 · Cited by 48 · see citing works
“The microscopic observation by TEM of the exposure of pathogens to Carvacrol displayed that this compound seem to penetrate the cytoplasmic membrane, increasing the permeability and causing the shrinkage of the protoplasm and the loss of cytosolic material [9, 58].”
Menthol Inhibits 5-HT3 Receptor–Mediated Currents
Ashoor, A., Nordman, J. C., Veltri, D., Yang, K. S., Шуба, Я. М., Kury, L. T. A., Sadek, B. S., Howarth, F. C., Shehu, A., Kabbani, N., et al. (2013) · Journal of Pharmacology and Experimental Therapeutics · doi:10.1124/jpet.113.203976 · Cited by 48 · see citing works
“…manner, including skeletal muscle sarcoplasmic reticulum (EC505 938 mM–1mM) (Palade, 1987; Neumann and Copello, 2011), tracheal epithelial cells (100 mM–1 mM) (Takeuchi et al., 1994), human leukemia cells (25–100 mM) (Lu et al., 2006), and dorsal horn neurons (100 mM–1 mM) (Tsuzuki et al., 2004).”
Background
Vitamin K enhances the effect of antibiotics inhibiting the efflux pumps of Staphylococcus aureus strains
Tintino, S. R., Oliveira–Tintino, C. D. D. M., Campina, F. F., Limaverde, P. W., Pereira, P. S., Siqueira-Júnior, J. P., Coutinho, H. D. M., Quintans‐Júnior, L. J., da Silva, T. G., Leal‐Balbino, T. C., et al. (2017) · Medicinal Chemistry Research · doi:10.1007/s00044-017-2063-y · Cited by 47 · see citing works
“…resulting in damage of the fundamental elements needed for membrane integrity, such as reduced membrane potential and loss of ions, cytochrome C, proteins and radicals, followed by the collapse of the proton pump and ATP depletion (Sikkema et al. 1994; Turina et al. 2006; Hirayama et al. 2006).”
Background
Antibacterial Effect of Thymol Loaded SBA-15 Nanorods Incorporated in PCL Electrospun Fibers
Gámez, E., Elizondo-Castillo, H., Tascon, J., García-Salinas, S., Navascués, N., Mendoza, G., Arruebo, M., & Irusta, S. (2020) · Nanomaterials · doi:10.3390/nano10040616 · Cited by 46 · see citing works
“This kind of compound, due to the hydrophobic effect, can easily self-assemble spontaneously in an aqueous media [48], forming micellar systems around silica particles, which would remain in the release medium due to the micellar concentration achievable [48].”
Background
Structural basis for promiscuous action of monoterpenes on TRP channels
Nguyen, T. H. D., Itoh, S., Okumura, H., & Tominaga, M. (2021) · Communications Biology · doi:10.1038/s42003-021-01776-0 · Cited by 46 · see citing works
Neomenthol prevents the proliferation of skin cancer cells by restraining tubulin polymerization and hyaluronidase activity
Fatima, K., Masood, N., Wani, Z. A., Meena, A., & Luqman, S. (2021) · Journal of Advanced Research · doi:10.1016/j.jare.2021.06.003 · Cited by 46 · see citing works
Advances in polysaccharide-based antibacterial materials
He, M., Huang, Y., Wang, J., Chen, Z., Xie, J., Cui, Z., Xu, D., Zhang, X., & Yao, W. (2025) · International Journal of Biological Macromolecules · doi:10.1016/j.ijbiomac.2025.142598 · Cited by 44 · see citing works
Citotoxic activity evaluation of essential oils and nanoemulsions of Drimys angustifolia and D. brasiliensis on human glioblastoma (U-138 MG) and human bladder carcinoma (T24) cell lines in vitro
Gomes, M. R. F., Schuh, R. S., Jacques, A. L. B., Augustin, O. A., Bordignon, S. A. D. L., Dias, D. D. O., Kelmann, R. G., Koester, L., Gehring, M. P., Morrone, F. B., et al. (2012) · Revista Brasileira de Farmacognosia · doi:10.1590/s0102-695x2012005000136 · Cited by 44 · see citing works
“As typical lipophilic substances, they pass through cytoplasmic membrane, breaking the structure of their different layers of polysaccharides, fatty acids and phospholipids and finally permeate them (Di Pasqua et al., 2006; Turina et al., 2006).”
Background
Essential oil compositions, antibacterial and antioxidant activities of various populations of Artemisia chamaemelifolia at two phenological stages
Pirbalouti, A. G., Firoznezhad, M., Craker, L. E., & Akbarzadeh, M. (2013) · Revista Brasileira de Farmacognosia · doi:10.1590/s0102-695x2013000600002 · Cited by 43 · see citing works
“If the membrane integrity is disturbed, then the membrane properties of barrier, matrix for enzymes and energy transducer are compromised (Turina Adel et al., 2006; Gill and Holley, 2006).”
Background
The effect of the combined use of high pressure treatment and antimicrobial edible film on the quality of salmon carpaccio
Gómez‐Estaca, J., López-Caballero, M. E., Martínez-Bartolomé, M. Á., de Lacey, A. M. L., Gómez-Guillén, M. C., & Montero, M. P. (2018) · International Journal of Food Microbiology · doi:10.1016/j.ijfoodmicro.2018.06.015 · Cited by 43 · see citing works
Oxidation Reactions of Thymol: A Pulse Radiolysis and Theoretical Study
Venu, S., Naik, D. B., Sarkar, S. K., Aravind, U. K., Nijamudheen, A., & Aravindakumar, C. T. (2012) · The Journal of Physical Chemistry A · doi:10.1021/jp3082358 · Cited by 43 · see citing works
Effect of oregano essential oil and carvacrol on Cryptosporidium parvum infectivity in HCT-8 cells
Gaur, S., Kuhlenschmidt, T. B., Kuhlenschmidt, M. S., & Andrade, J. E. (2017) · Parasitology International · doi:10.1016/j.parint.2017.11.001 · Cited by 42 · see citing works
Stability and antimicrobial activity of eucalyptus essential oil emulsions
Clavijo-Romero, A., Quintanilla‐Carvajal, M. X., & Ruíz, Y. (2018) · Food Science and Technology International · doi:10.1177/1082013218794841 · Cited by 45 · see citing works
“These attributes of this essential oil are related to membrane damage (Di Pasqua et al., 2007; Nazzaro et al., 2013; Turina et al., 2006), cytotoxicity and neurotoxicity (Burt, 2004; Murata et al.”
The effectiveness of tricaine, benzocaine, clove oil, and menthol as anesthetics for lambari-bocarra Oligosarcus argenteus
Uehara, S. A., de Andrade, D. R., Takata, R., Júnior, A., & Vidal, M. V. (2018) · Aquaculture · doi:10.1016/j.aquaculture.2018.12.054 · Cited by 40 · see citing works
Anti-Oxidant and Anti-Melanogenic Properties of Essential Oil from Peel of Pomelo cv. Guan Xi
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“Due to the high hydrophobicity of terpenoids, their toxic effects lead to swelling and enhanced fluidity and permeability of the cell membranes [27].”
Background
Geraniol attenuates oxidative stress, bioaccumulation, serological and histopathological changes during aluminum chloride-hepatopancreatic toxicity in male Wistar rats
Hosseini, S. M., Hejazian, L. B., Amani, R., & Badeli, N. S. (2020) · Environmental Science and Pollution Research · doi:10.1007/s11356-020-08128-1 · Cited by 40 · see citing works
Current advances in the bacterial toolbox for the biotechnological production of monoterpene-based aroma compounds
Castro, P. S., Soares, F., & Santos, P. M. (2021) · Portuguese National Funding Agency for Science, Research and Technology (RCAAP Project by FCT) · doi:10.3390/molecules26010091
Noncompetitive Inhibition of 5-HT3 Receptors by Citral, Linalool, and Eucalyptol Revealed by Nonlinear Mixed-Effects Modeling
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“…nature of the oils suggests that the binding sites of citral, eucalyptol, and linalool are located in the transmembrane region, consistent with the slow wash-in and washout that is observed when compounds must first diffuse into membranes before reaching their target (Turina et al., 2006).”
Background

Natural terpenes II. Concentration-dependent profile of effects on dynamic organization of biological and model membranes
Turina, A. V., Clop, E. M., & Perillo, M. A. (2024) · Biochemical and Biophysical Research Communications · doi:10.1016/j.bbrc.2024.151179 · Cited by 3 · see citing works
Cyclic and Linear Monoterpenes in Phospholipid Membranes: Phase Behavior, Bilayer Structure, and Molecular Dynamics
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Studies on the Behavior of Eucalyptol and Terpinen-4-ol—Natural Food Additives and Ecological Pesticides—in Model Lipid Membranes
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Effect of a series of essential oil molecules on DPPC membrane fluidity: a biophysical study
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Synthetic meroterpenoids based on terpene alcohols: synthesis, self-assembly, and membranotropic properties
Akhmedov, A. A., Shurpik, D. N., Latypova, Z. R., Gamirov, R. R., & Stoykov, I. I. (2020) · Butlerov Communications · doi:10.37952/roi-jbc-01/20-63-7-11

Authors: Turina, A. D. V., Nolan, M. V., Zygadlo, J. A., & Perillo, M. A.
Affiliations: Universidad Nacional de Córdoba (AR)
Corresponding author: Perillo, M.A.
ORCID: Zygadlo, J.A.
Perillo, M.A.
Venue: Biophysical Chemistry
Publisher: Elsevier BV
Published: 2006-07
Volume: 122
Issue: 2
Pages: 101-113
ISSN: 0301-4622 (ISSN-L)
DOI: 10.1016/j.bpc.2006.02.007
OpenAlex: W2070361637
Cited by: 305
References: 50
Citations by year: 2026: 15 · 2025: 13 · 2024: 21 · 2023: 16 · 2022: 20 · 2021: 21 · 2020: 31 · 2019: 22 · 2018: 21 · 2017: 24 · 2016: 18 · 2015: 13 · 2014: 20 · 2013: 17 · 2012: 10
FWCI: 1.36
Type: journal article
Language: en
Open access: closed
Licence: www.elsevier.com/tdm/userlicense/1.0/ (tdm)
Locations: Biophysical Chemistry (publishedVersion)
PubMed (publishedVersion)
Topics: Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Lipid Membrane Structure and Behavior
Physical Sciences › Chemistry › Organic Chemistry › Surfactants and Colloidal Systems
Life Sciences › Agricultural and Biological Sciences › Food Science › Essential Oils and Antimicrobial Activity
Keywords: monoterpenes, essential oils, self-assembly, critical micelle concentration, membrane partitioning, surface activity, camphor, 1,8-cineole, thymol, menthol, geraniol, DPPC, Triton X-100, vesicle curvature, membrane polarity, solvation, principal component analysis
MeSH terms: Air, Octanols, Bromthymol Blue, Diffusion, Membranes, Artificial, Micelles, Particle Size, Permeability, Phosphatidylcholines, Pyrimidinones, Surface Properties, Terpenes, Water, Molecular Structure, Octoxynol, Principal Component Analysis

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Natural terpenes: Self-assembly and membrane partitioning

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