Monoterpenes: Essential Oil Components with Valuable Features

Author(s): Anahita Boveiri Dehsheikh, Mohammad Mahmoodi Sourestani*, Paria Boveiri Dehsheikh, Javad Mottaghipisheh, Sara Vitalini, Marcello Iriti*

Journal Name: Mini-Reviews in Medicinal Chemistry

Volume 20 , Issue 11 , 2020

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Graphical Abstract:


Medicinal plants have a wide range of secondary metabolites including monoterpene. These volatile compounds are the main components of essential oils, belonging to the isoprenoid group and possessing valuable features for plants and humans. This review provides comprehensive information on chemical structures and classification of monoterpenes. It describes their biosynthesis pathways and introduces plant families and species rich in noteworthy monoterpenes. Bio-activities, pharmacological and pesticide effects as well as their mechanism of action are reported. Applications of these compounds in various industries are also included.

Keywords: Anticancer, antimicrobial, antioxidant, bioherbicides, essential oil, insecticides, monoterpenes, preservatives, secondary metabolites, volatile aromatic oils.

Isman, M.B. Plant essential oils for pest and disease management. Crop Prot., 2000, 19(8-10), 603-608.
Friedrich, H. Phenylpropanoid constituents of essential oils. Lloydia, 1976, 39(1), 1-7.
Baser, K.H.C.; Demirci, F. Chemistry of essential oils. Flavours and Fragrances Chemistry, Ed. Springer: Berlin, 2007, 43-86.
Breitmaier, E. Terpenes. Flavors, Fragrances, Pharmaca. Pheromones, 2006.
Wink, M.; Van Wyk, B.E. Mind-altering and Poisonous Plants of the World., 2008.
Ashour, M.; Wink, M.; Gershenzon, J. Biochemistry of terpenoids: Monoterpenes, sesquiterpenes and diterpenes. 2010.
Sangwan, N.S.; Farooqi, A.H.A.; Shabih, F.; Sangwan, R.S. Regulation of essential oil production in plants. Plant Growth Regul., 2001, 34(1), 3-21.
Mahmoud, S.S.; Croteau, R.B. Strategies for transgenic manipulation of monoterpene biosynthesis in plants. Trends Plant Sci., 2002, 7(8), 366-373.
Ramawat, K.G.; Merillon, J.M. Natural products: Phytochemistry, botany and metabolism of alkaloids, phenolics and terpenes., 2013.
Hunter, M. Essential oils: art, agriculture, science, industry and entrepreneurship (a Focus on the Asia-Pacific region)., 2009.
Pengelly, A. The Constituents of Medicinal Plants, (2nd ed.); , 2004.
Tisserand, R.; Young, R. Essential Oil Safety A Guide for Health Care Professionals., 2014.
Crozier, A.; Clifford, M.N.; Ashihara, H. Plant secondary metabolites: Occurrence, structure and role in the human diet., 2008.
Schalk, M.; Croteau, R. A single amino acid substitution (F363I) converts the regiochemistry of the spearmint (-)-limonene hydroxylase from a C6- to a C3-hydroxylase. Proc. Natl. Acad. Sci. USA, 2000, 97(22), 11948-11953.
Santos-Gomes, P.C.; Fernandes-Ferreira, M. Essential oils produced by in vitro shoots of sage (Salvia officinalis L.). J. Agric. Food Chem., 2003, 51(8), 2260-2266.
Koparal, A.T.; Zeytinoglu, M. Effects of carvacrol on a human non-small cell lung cancer (NSCLC) cell line, A549. Cytotechnology, 2003, 43(1-3), 149-154.
Keszei, A.; Brubaker, C.L.; Foley, W.J. A molecular perspective on terpene variation in Australian Myrtaceae. Aust. J. Bot., 2008, 56(3), 197-213.
Chizzola, R. Regular monoterpenes and sesquiterpenes (Essential oils). Nat. Prod., 2013, 2973-3008.
Sarma, A.D.; Mallick, A.R.; Ghosh, A.K. Free radicals and their role in different clinical conditions: An overview. Int. J. Pharm. Sci. Res., 2010, 1(3), 185-192.
Bakkali, F.; Averbeck, S.; Averbeck, D.; Idaomar, M. Biological effects of essential oils. A review. Food Chem. Toxicol., 2008, 46(2), 446-475.
Yildirim, A.; Mavi, A.; Oktay, M.; Kara, A.A.; Algur, O.; Bilaloglu, V. Comparison of antioxidant and antimicrobial activities of tilia (Tilia argentea Desf ex DC), sage (Salvia triloba l.), and black tea (Camellia sinensis) extracts. J. Agric. Food Chem., 2000, 48(10), 5030-5034.
Mao, L.C.; Pan, X.; Que, F.; Fang, X.H. Antioxidant properties of water and ethanol extracts from hot air-dried and freeze-dried daylily flowers. Eur. Food Res. Technol., 2006, 222(3-4), 236-241.
Wojtunik, K.A.; Ciesla, L.M.; Waksmundzka-Hajnos, M. Model studies on the antioxidant activity of common terpenoid constituents of essential oils by means of the 2,2-diphenyl-1-picrylhydrazyl method. J. Agric. Food Chem., 2014, 62(37), 9088-9094.
Ruberto, G.; Baratta, M.T. Antioxidant activity of selected essential oil components in two lipid model systems. Food Chem., 2000, 69(2), 167-174.
Bozin, B.; Mimica-Dukic, N.; Simin, N.; Anackov, G. Characterization of the volatile composition of essential oils of some lamiaceae spices and the antimicrobial and antioxidant activities of the entire oils. J. Agric. Food Chem., 2006, 54(5), 1822-1828.
Bounatirou, S.; Smiti, S.; Miguel, M.G.; Faleiro, L.; Rejeb, M.N.; Neffati, M.; Costa, M.M.; Figueiredo, A.C.; Barroso, J.G.; Pedro, L.G. Chemical composition, antioxidant and antibacterial activities of the essential oils isolated from Tunisian Thymus capitatus Hoff. et Link. Food Chem., 2007, 105(1), 146-155.
Zengin, H.; Baysal, A.H. Antibacterial and antioxidant activity of essential oil terpenes against pathogenic and spoilage-forming bacteria and cell structure-activity relationships evaluated by SEM microscopy. Molecules, 2014, 19, 17773-17798.
Hanahan, D.; Weinberg, R.A. Hallmarks of cancer: the next generation. Cell Press, 2011, 144(5), 646-674.
Zhang, Q.Y.; Wang, F.X.; Jia, K.K.; Kong, L.D. Natural product interventions for chemotherapy and radiotherapy-induced side effects. Front. Pharmacol., 2018, 9, 1253.
Pavan, V.; Ribaudo, G.; Zorzan, M.; Redaelli, M.; Pezzani, R.; Mucignat-Caretta, C.; Zagotto, G. Antiproliferative activity of Juglone derivatives on rat glioma. Nat. Prod. Res., 2017, 31(6), 632-638.
Gautam, N.; Mantha, A.K.; Mittal, S. Essential oils and their constituents as anticancer agents: a mechanistic view. BioMed Res. Int., 2014, 154106, 1-23.
Akrout, A.; Gonzalez, L.A.; El Jani, H.; Madrid, P.C. Antioxidant and antitumor activities of Artemisia campestris and Thymelaea hirsuta from southern Tunisia. Food Chem. Toxicol., 2011, 49(2), 342-347.
Jayaprakasha, G.K.; Murthy, K.C.; Uckoo, R.M.; Patil, B.S. Chemical composition of volatile oil from Citrus limettioides and their inhibition of colon cancer cell proliferation. Ind. Crops Prod., 2013, 2013(45), 200-207.
Ripple, G.H.; Gould, M.N.; Stewart, J.A.; Tutsch, K.D.; Arzoomanian, R.Z.; Alberti, D.; Bailey, H.H. Phase I clinical trial of perillyl alcohol administered daily. Clin. Cancer Res., 1998, 4(5), 1159-1164.
Bailey, H.H.; Levy, D.; Harris, L.S.; Schink, J.C.; Foss, F.; Beatty, P.; Wadler, S. A phase II trial of daily perillyl alcohol in patients with advanced ovarian cancer: Eastern Cooperative Oncology Group Study E2E96. Gynecol. Oncol., 2002, 85(3), 464-468.
Bardon, S.; Foussard, V.; Fournel, S.; Loubat, A. Monoterpenes inhibit proliferation of human colon cancer cells by modulating cell cycle-related protein expression. Cancer Lett., 2002, 181(2), 187-194.
Loutrari, H.; Hatziapostolou, M.; Skouridou, V.; Papadimitriou, E.; Roussos, C.; Kolisis, F.N.; Papapetropoulos, A. Perillyl alcohol is an angiogenesis inhibitor. J. Pharmacol. Exp. Ther., 2004, 311(2), 568-575.
Döll-Boscardin, P.M.; Sartoratto, A.; Maia, S.; de Noronha, B.H.L.; Padilha de Paula, J.; Nakashima, T.; Kanunfre, C.C. In vitro cytotoxic potential of essential oils of Eucalyptus benthamii and its related terpenes on tumor cell lines. Evid. Based Complement. Alternat. Med, 2012, 12, 1-8.
Raut, J.S.; Karuppayil, S.M. A status review on the medicinal properties of essential oils. Ind. Crops Prod., 2014, 62, 250-264.
Saad, N.Y.; Muller, C.D.; Lobstein, A. Major bioactivities and mechanism of action of essential oils and their components. Flavour Fragrance J., 2013, 28(5), 269-279.
Swamy, M.K.; Akhtar, M.S.; Sinniah, U.R. Antimicrobial properties of plant essential oils against human pathogens and their mode of action: An updated review. Evid. Based Complement. Alternat. Med., 2016, 1-21.
Degenhardt, J.; Köllner, T.G.; Gershenzon, J. Monoterpene and sesquiterpene synthases and the origin of terpene skeletal diversity in plants. Phytochemistry, 2009, 70(15-16), 1621-1637.
Ultee, A.; Bennik, M.H.J.; Moezelaar, R. The phenolic hydroxyl group of carvacrol is essential for action against the food-borne pathogen Bacillus cereus. Appl. Environ. Microbiol., 2002, 68(4), 1561-1568.
Cristani, M.; D’Arrigo, M.; Mandalari, G.; Castelli, F.; Sarpietro, M.G.; Micieli, D.; Trombetta, D. Interaction of four monoterpenes contained in essential oils with model membranes: implications for their antibacterial activity. J. Agric. Food Chem., 2007, 55(15), 6300-6308.
Trombetta, D.; Castelli, F.; Sarpietro, M.G.; Venuti, V.; Cristani, M.; Daniele, C.; Bisignano, G. Mechanisms of antibacterial action of three monoterpenes. Antimicrob. Agents Ch., 2005, 49(6), 2474-2478.
Lee, Y.H.; Choi, C.W.; Kim, S.H.; Yun, J.G.; Chang, S.W.; Kim, Y.S.; Hong, J.K. Chemical pesticides and plant essential oils for disease control of tomato bacterial wilt. Plant Pathol. J., 2012, 28(1), 32-39.
Rojas-Grau, M.A.; Avena-Bustillos, R.J.; Olsen, C.; Friedman, M.; Henika, P.R.; Mart’ın-Belloso, O.; Pan, Z.; McHugh, T.H. Effects of plant essential oils and oil compounds on mechanical, barrier and antimicrobial properties of alginate-apple puree edible films. J. Food Eng., 2007, 81(3), 634-641.
Friedman, M.; Henika, P.R.; Mandrell, R.E. Bactericidal activities of plant essential oils and some of their isolated constituents against Campylobacter jejuni, Escherichia coli, Listeria monocytogenes, and Salmonella enterica. J. Food Prot., 2002, 65(10), 1545-1560.
Burt, S. Essential oils: their antibacterial properties and potential applications in foods--a review. Int. J. Food Microbiol., 2004, 94(3), 223-253.
Veldhuizen, E.J.A.; Tjeerdsma-van Bokhoven, J.L.M.; Zweijtzer, C.; Burt, S.A.; Haagsman, H.P. Structural requirements for the antimicrobial activity of carvacrol. J. Agric. Food Chem., 2006, 54(5), 1874-1879.
Lambert, R.J.W.; Skandamis, P.N.; Coote, P.J.; Nychas, G.J.E. A study of the minimum inhibitory concentration and mode of action of oregano essential oil, thymol and carvacrol. J. Appl. Microbiol., 2001, 91(3), 453-462.
Aguirre, A.; Borneo, R.; León, A.E. Antimicrobial, mechanical and barrier properties of triticale protein films incorporated with oregano essential oil. Food Biosci., 2013, 1, 2-9.
Aleksic, V.; Knezevic, P. Antimicrobial and antioxidative activity of extracts and essential oils of Myrtus communis L. Microbiol. Res., 2014, 169(4), 240-254.
Yoon, H.S.; Moon, S.C.; Kim, N.D.; Park, B.S.; Jeong, M.H.; Yoo, Y.H. Genistein induces apoptosis of RPE-J cells by opening mitochondrial PTP. Biochem. Biophys. Res. Commun., 2000, 276(1), 151-156.
Velluti, A.; Sanchis, V.; Ramos, A.J.; Egido, J.; Marín, S. Inhibitory effect of cinnamon, clove, lemongrass, oregano and palmarose essential oils on growth and fumonisin B1 production by Fusarium proliferatum in maize grain. Int. J. Food Microbiol., 2003, 89(2-3), 145-154.
Velluti, A.; Sanchis, V.; Ramos, A.J.; Turon, C.; Marín, S. Impact of essential oils on growth rate, zearalenone and deoxynivalenol production by Fusarium graminearum under different temperature and water activity conditions in maize grain. J. Appl. Microbiol., 2004, 96(4), 716-724.
Garcia, R.; Alves, E.S.; Santos, M.P.; Aquije, G.M.; Fernandes, A.A.R.; Santos, R.B.D.; Fernandes, P. Antimicrobial activity and potential use of monoterpenes as tropical fruits preservatives. Braz. J. Microbiol., 2008, 39(1), 163-168.
Cox, S.D.; Mann, C.M.; Markham, J.L.; Bell, H.C.; Gustafson, J.E.; Warmington, J.R.; Wyllie, S.G. The mode of antimicrobial action of the essential oil of Melaleuca alternifolia (tea tree oil). J. Appl. Microbiol., 2000, 88(1), 170-175.
Parveen, M.; Hasan, M.K.; Takahashi, J.; Murata, Y.; Kitagawa, E.; Kodama, O.; Iwahashi, H. Response of Saccharomyces cerevisiae to a monoterpene: evaluation of antifungal potential by DNA microarray analysis. J. Antimicrob. Chemother., 2004, 54(1), 46-55.
Adegoke, G.O.; Iwahashi, H.; Komatsu, Y.; Obuchi, K.; Iwahashi, Y. Inhibition of food spoilage yeasts and aflatoxigenic moulds by monoterpenes of the spice Aframomum danielli. Flavour Frag. J., 2000, 15(3), 147-150.
Schnitzler, P.; Schön, K.; Reichling, J. Antiviral activity of Australian tea tree oil and eucalyptus oil against herpes simplex virus in cell culture. Pharmazie, 2001, 56(4), 343-347.
Böhme, K.; Barros-Velázquez, J.; Calo-Mata, P.; Aubourg, S.P. Antibacterial, antiviral and antifungal activity of essential oils: Mechanisms and applications. Antimicrob. Comp., 2014.
Camero, M.; Lanave, G.; Catella, C.; Capozza, P.; Gentile, A.; Fracchiolla, G.; Britti, D.; Martella, V.; Buonavoglia, C.; Tempesta, M. Virucidal activity of ginger essential oil against caprine alphaherpesvirus-1. Vet. Microbiol., 2019, 230, 150-155.
Bezic, N.; Dunkic, V.; Elma, V. Antiphytoviral activity of essential oils of some Lamiaceae species and there most important compounds on CMV and TMV. Microbial pathogens and strategies for combating them: science, technology and education., 2013, Vol. 2, 982-988.
Maria do Socorro, S.R.; Mendonça-Filho, R.R.; Bizzo, H.R.; de Almeida Rodrigues, I.; Soares, R.M.A.; Souto-Padrón, T.; Alviano, C.S.; Lopes, A.H.C. Antileishmanial activity of a linalool-rich essential oil from Croton cajucara. Antimicrob. Agents Chemother., 2003, 47(6), 1895-1901.
Ramos-Lopez, M.A.; Sanchez-Mir, E.; Fresan-Orozco, M.C.; Perez-Ramos, J. Antiprotozoal activity of some essential oils. J. Med. Plants Res., 2012, 6(15), 2901-2908.
Goodner, K.L.; Mahattanatawee, K.; Plotto, A.; Sotomayor, J.A.; Jordan, M.J. Aromatic profiles of Thymus hyemalis and Spanish Thymus vulgaris essential oils by GC-MS/GC-O. Ind. Crops Prod., 2006, 24(3), 264-268.
Viollon, C.; Mandin, D.; Chaumont, J.P. Activites antagonistes, in vitro, of some essential oils and natural volatile compounds vis a vis the growth of Trichomonas vaginalis. Fitoterapia, 1996, 67, 279-281.
Escobar, P.; Leal, S.M.; Herrera, L.V.; Martinez, J.R.; Stashenko, E. Chemical composition and antiprotozoal activities of Colombian Lippia spp essential oils and their major components. Mem. Inst. Oswaldo Cruz, 2010, 105(2), 184-190.
Saeidnia, S.; Gohari, A.R.; Hadjiakhoondi, A. Trypanocidal activity of oil of the young leaves of Nepeta cataria L. obtained by solvent extraction. Faslnamah-i Giyahan-i Daruyi, 2008, 7(4), 54-57.
Enan, E. Insecticidal activity of essential oils: octopaminergic sites of action. Comp. Biochem. Physiol. C Toxicol. Pharmacol., 2001, 130(3), 325-337.
Kostyukovsky, M.; Rafaeli, A.; Gileadi, C.; Demchenko, N.; Shaaya, E. Activation of octopaminergic receptors by essential oil constituents isolated from aromatic plants: possible mode of action against insect pests. Pest Manag. Sci., 2002, 58, 1101-1106.
Picollo, M.I.; Toloza, A.C.; Cueto, G.M.; Zygadlo, J.; Zerba, E. Anticholinesterase and pediculicidal activities of monoterpenoids. Fitoterapia, 2008, 79(4), 271-278.
Lopez, M.D.; Pascual-Villalobos, M.J. Mode of inhibition of acetylcholinesterase by monoterpenoids and implications for pest control. Ind. Crops Prod., 2010, 31(2), 284-288.
Höld, K.M.; Sirisoma, N.S.; Ikeda, T.; Narahashi, T.; Casida, J.E. α-thujone (the active component of absinthe): γ-aminobutyric acid type A receptor modulation and metabolic detoxification. Proc. Natl. Acad. Sci. USA, 2000, 97(8), 3826-3831.
Regnault-Roger, C.; Vincent, C.; Thor, J. Essential oils in insect control: low-risk products in a high-stakes world. Annu. Rev. Entomol., 2012, 57, 405-424.
Thongdon-A, J.; Inprakhon, P. Composition and biological activities of essential oils from Limnophila geoffrayi Bonati. World J. Microbiol. Biotechnol., 2009, 25(8), 1313-1320.
Gillilan, J. Improvement of U.S. EPA minimum risk essential oils’ pesticide activity through surfactant enhancement and synergy. Ph.D. Thesis, The Ohio State University: Columbus, 2012.
Park, I.K.; Choi, K.S.; Kim, D.H.; Choi, I.H.; Kim, L.S.; Bak, W.C.; Choi, J.W.; Shin, S.C. Fumigant activity of plant essential oils and components from horseradish (Armoracia rusticana), anise (Pimpinella anisum) and garlic (Allium sativum) oils against Lycoriella ingenua (Diptera: Sciaridae). Pest Manag. Sci., 2006, 62(8), 723-728.
Herrmann, A. The chemistry and biology of volatiles, (1st ed.); , 2010.
Zapata, N.; Smagghe, G. Repellency and toxicity of essential oils from the leaves and bark of Laurelia sempervirens and Drimys winteri against Tribolium castaneum. Ind. Crops Prod., 2010, 32(3), 405-410.
Wang, X.; Hao, Q.; Chen, Y.; Jiang, S.; Yang, Q.; Li, Q. The effect of chemical composition and bioactivity of several essential oils on Tenebrio molitor (Coleoptera: Tenebrionidae). J. Insect Sci., 2015, 15(1), 1-7.
Koul, O.; Walia, S.; Dhaliwal, G.S. Essential oils as green pesticides: Potential and constraints. Biopestic. Int. (Jalandhar), 2008, 4(1), 63-84.
Ebadollahi, A.; Safaralizadeh, M.; Pourmirza, A. Fumigant toxicity of Lavandula stoechas L. oil against three insect pests attacking stored products. J. Plant Prot. Res., 2010, 50(1), 56-60.
Tuni, I.; Sahinkaya, S. Sensitivity of two greenhouse pests to vapours of essential oils. Entomol. Exp. Appl., 1998, 86(2), 183-187.
Huang, Y.; Hee, S.K.; Ho, S.H. Antifeedant and growth inhibitory effects of a-pinene on the stored-product insects, Tribolium castaneum (Herbst) and Sitophilus zeamais Motsch. Int. Pest. Control, 1998, 40(1), 18-20.
Singh, D.; Siddiqui, M.S.; Sharma, S. Reproduction retardant and fumigant properties in essential oils against rice weevil (Coleoptera: Curculionidae) in stored wheat. J. Econ. Entomol., 1989, 82(3), 727-732.
Regnault-Roger, C.; Hamraoui, A.; Holeman, M.; Theron, E.; Pinel, R. Insecticidal effect of essential oils from mediterranean plants uponAcanthoscelides Obtectus Say (Coleoptera, Bruchidae), a pest of kidney bean (Phaseolus vulgaris L.). J. Chem. Ecol., 1993, 19(6), 1233-1244.
Isman, M. Insect antifeedants. Pestic. Outlook, 2002, 13(4), 152-157.
Arivoli, S.; Tennyson, S. Antifeedant activity of plant extracts against Spodoptera litura (Fab.) (Lepidoptera: Noctuidae). Am.-Eurasian J. Agric. Environ. Sci., 2012, 12(6), 764-768.
Athanassiou, C.G.; Rani, P.U.; Kavallieratos, N.G. The use of plant extracts for stored product protection., 2014.
Abbas, S.K.; Ahmad, F.; Sagheer, M.; Hasan, M.; Yasir, M.; Saeed, A.; Wali, M. Insecticidal and growth inhibition activities of Citrus paradisi and Citrus reticulata essential oils against lesser grain borer, Rhyzopertha dominica (F.) (Coleoptera: Bostrichidae). World J. Zool., 2012, 7(4), 289-294.
Arshad, Z.; Hanif, M.A.; Qadri, R.W.K.; Khan, M.M.; Babarinde, A.; Omisore, G.O.; Latif, S. Role of essential oils in plant diseases protection: A review. Int. J. Chem. Biochem. Sci., 2014, 6, 11-17.
Katerinopoulos, H.E.; Pagona, G.; Afratis, A.; Stratigakis, N.; Roditakis, N. Composition and insect attracting activity of the essential oil of Rosmarinus officinalis. J. Chem. Ecol., 2005, 31(1), 111-122.
Kordali, S.; Cakir, A.; Sutay, S. Inhibitory effects of monoterpenes on seed germination and seedling growth. Z. Naturforsch. C., 2007, 62(3-4), 207-214.
Singh, H.P.; Batish, D.R.; Kaur, S.; Ramezani, H.; Kohli, R.K. Comparative phytotoxicity of four monoterpenes against Cassia occidentalis. Ann. Appl. Biol., 2002, 141(2), 111-116.
Chaimovitsh, D.; Rogovoy Stelmakh, O.; Altshuler, O.; Belausov, E.; Abu-Abied, M.; Rubin, B.; Sadot, E.; Dudai, N. The relative effect of citral on mitotic microtubules in wheat roots and BY2 cells. Plant Biol., 2012, 14, 354-364.
Singh, H.P.; Kaur, S.; Mittal, S.; Batish, D.R.; Kohli, R.K. Essential oil of Artemisia scoparia inhibits plant growth by generating reactive oxygen species and causing oxidative damage. J. Chem. Ecol., 2009, 35(2), 154-162.
Kaur, S.; Singh, H.P.; Batish, D.R.; Kohli, R.K. Chemical characterization and allelopathic potential of volatile oil of Eucalyptus tereticornis against Amaranthus viridis. J. Plant Interact., 2011, 6(4), 297-302.
Nishida, N.; Tamotsu, S.; Nagata, N.; Saito, C.; Sakai, A. Allelopathic effects of volatile monoterpenoids produced by Salvia leucophylla: Inhibition of cell proliferation and DNA synthesis in root apical meristem of Brassica campestris seedlings. J. Chem. Ecol., 2005, 31(5), 1187-1203.
Ali, B.; Al-Wabel, N.A.; Shams, S.; Ahamad, A.; Khan, S.A.; Anwar, F. Essential oils used in aromatherapy: A systemic review. Asian Pac. J. Trop. Biomed., 2015, 5(8), 601-611.
Baser, K.H.C.; Buchbauer, G. Handbook of essential oils: Science, technology, and applications 2nd ed.; CRC Press, Taylor and Francis Group: Boca Raton, 2016.
Wichtel, M. Teedrogen und Phytopharmaka., 2002.
Benchaa, S.; Hazzit, M.; Abdelkrim, H. Allelopathic effect of Eucalyptus citriodora essential oil and its potential use as bioherbicide. Chem. Biodivers., 2018, 15, e1800202
Sarkic, A.; Stappen, I. Essential Oils and their single compounds in cosmetics—A critical review. Cosmetics, 2018, 5(1), 11.
Oussalah, M.; Caillet, S.; Saucier, L.; Lacroix, M. Inhibitory effects of selected plant essential oils on Pseudomonas putida growth, a bacterial spoilage meat. Meat Sci., 2006, 73(2), 236-244.
Azimova, S.S.; Glushenkova, A.I.; Vinogradova, V. Lipids, lipophilic components and essential oils from plant sources, (1st ed.); , 2012.
Husnu Can Baser, K.; Buchbauer, G. Handbook of Essential Oils: Science; Technology, and Applications, 2009.
Goodman, N.B.; Wheeler, A.J.; Paevere, P.J.; Agosti, G.; Nematollahi, N.; Steinemann, A. Emissions from dryer vents during use of fragranced and fragrance-free laundry products. Air Qual. Atmos. Health, 2019, 12(3), 289-295.
De Groot, A. Linalool Hydroperoxides. Dermatitis, 2019, 30(4), 243-246.
Sköld, M.; Hagvall, L.; Karlberg, A.T. Autoxidation of linalyl acetate, the main component of lavender oil, creates potent contact allergens. Contact Dermat., 2008, 58, 9-14.
Woronuk, G.; Demissie, Z.; Rheault, M.; Mahmoud, S. Biosynthesis and therapeutic properties of Lavandula essential oil constituents. Planta Med., 2011, 77(1), 7-15.
Okaru, A.O.; Lachenmeier, D.W. The food and beverage occurrence of furfuryl alcohol and myrcene—Two emerging potential human carcinogens? Toxins (Basel), 2017, 5, 9.
Vichi, S.; Riu-Aumatell, M.; Mora-Pons, M.; Buxaderas, S.; pez-Tamames, E.L. Characterization of volatiles in different dry gins. J. Agric. Food Chem., 2005, 53, 10154-10160.
Khaleel, C.; Tabanca, N.; Buchbauer, G. α-Terpineol, a natural monoterpene: A review of its biological properties. Open Chem., 2018, 16, 349-361.
Burt, S. Essential oils: their antibacterial properties and potential applications in foods--a review. Int. J. Food Microbiol., 2004, 94, 223-253.
Morcia, C.; Tumino, G.; Ghizzoni, R.; Terzi, V. Carvone (Mentha spicata L.) oils In: ; Essential oils in food preservation, flavor and safety; Preedy, Ed.. Elsevier Academic Press: Cambridge, Massachusetts., 2015; pp. 309-316.
Kotana, R.; Kordali, S.; Cakir, A. Screening of antibacterial activities of twenty-one oxygenated monoterpenes. Z. Naturforsch, 2007, 62, 507-513.
Siano, F.; Catalfamo, M.; Cautela, D.; Servillo, L.; Castaldo, D. Analysis of pulegone and its enanthiomeric distribution in mint-flavoured food products. Food Addit. Contam., 2005, 22(3), 197-203.
Lachenmeier, D.W.; Walch, S.G.; Padosch, S.A.; Kröner, L.U. Absinthe. A Review. Crit. Rev. Food Sci. Nutr., 2006, 46, 365-377.
Bouazza, F.; Hassikou, R.; Satrani, B.; Ghanmi, M.; Ennadir, J.; Khedid, K. In vitro antibacterial activity of Thymus saturejoides, Mentha pulegium, and Origanum vulgare essential oils against Escherichia coli isolated from raw sheep milk. Int. J. Agric. Innov. Res., 2014, 3(1), 210-217.
Akin, M.; Demirci, B.; Bagci, Y.; Baser, K.H.C. Antibacterial activity and composition of the essential oils of two endemic Salvia sp. from Turkey. Afr. J. Biotechnol., 2010, 9(15), 2322-2327.
Imelouane, B.; Amhamdi, H.; Wathelet, J.P.; Ankit, M.; Khedid, K.; El Bachiri, A. Chemical composition and antimicrobial activity of essential oil of thyme (Thymus vulgaris) from Eastern Morocco. Int. J. Agric. Biol., 2009, 11, 205-208.
Shatar, S.; Staneva, J.; Altantsetseg, S.; Todorova, M. Essential oil composition of three Ajania species from Mongolia. J. Essent. Oil Bear. Pl., 2010, 13(4), 460-464.
Morocho, V.; Toro, M.L.; Cartuche, L.; Guaya, D.; Valarezo, E.; Malagón, O.; Ramírez, J. Chemical composition and antimicrobial activity of essential oil of Lepechinia radula Benth Epling. Rec. Nat. Prod., 2017, 1(1), 57-62.
Kalantari, N.; Azar, P.A.; Larijani, K. Volatile components of Perovskia abrotanoides and Nepeta glomerulosa from Iran. Int. Res. J. Basic Appl. Sci., 2015, 9(10), 1686-1690.
Toncer, O.; Karaman, S.; Kizil, S.; Diraz, E. Changes in essential oil composition of oregano (Origanum onites L.) due to diurnal variations at different development stages. Not. Bot. Horti Agrobot. Cluj-Napoca, 2009, 37(2), 177-181.
Vale-Silva, L.; Silva, M.J.; Oliveira, D.; Gonçalves, M.J.; Cavaleiro, C.; Salgueiro, L.; Pinto, E. Correlation of the chemical composition of essential oils from Origanum vulgare subsp. virens with their in vitro activity against pathogenic yeasts and filamentous fungi. J. Med. Microbiol., 2012, 61(2), 252-260.
Fang, R.; Jiang, C.H.; Wang, X.Y.; Zhang, H.M.; Liu, Z.L.; Zhou, L.; Du, S.S.; Deng, Z.W. Insecticidal activity of essential oil of Carum Carvi fruits from China and its main components against two grain storage insects. Molecules, 2010, 15(12), 9391-9402.
Snoussi, M.; Noumi, E.; Trabelsi, N.; Flamini, G.; Papetti, A.; De Feo, V. Mentha spicata essential oil: Chemical composition, antioxidant and antibacterial activities against planktonic and biofilm cultures of Vibrio spp. strains. Molecules, 2015, 20(8), 14402-14424.
Sefidkon, F.; Assareh, M.H.; Abravesh, Z.; Barazandeh, M.M. Chemical composition of the essential oils of four cultivated Eucalyptus species in Iran as medicinal plants (E. microtheca, E. spathulata, E. largiflorens and E. torquata). Iran. J. Pharm. Res., 2007, 6(2), 135-140.
Bağdat, R.B.; Coşge, B. The essential oil of lemon balm (Melissa officinalis L.), its components and using fields. J. Fac. Agric. OMU, 2006, 21(1), 116-121.
Kamal, G.M.; Anwar, F.; Hussain, A.I.; Sarri, N.; Ashraf, M.Y. Yield and chemical composition of Citrus essential oils as affected by drying pretreatment of peels. Int. Food Res. J., 2011, 18(4), 1275-1282.
Loghmani-Khouzani, H.; Sabzi Fini, O.; Safari, J. Essential oil composition of Rosa damascena Mill. cultivated in central iran. Sci. Iran., 2007, 14(4), 316-319.
Sarikurkcu, C.; Ozer, M.S.; Eskici, M.; Tepe, B.; Can, Ş.; Mete, E. Essential oil composition and antioxidant activity of Thymus longicaulis C. Presl subsp. longicaulis var. longicaulis. Food Chem. Toxicol., 2010, 48(7), 1801-1805.
Tajidin, N.E.; Ahmad, S.H.; Rosenani, A.B.; Azimah, H.; Munirah, M. Chemical composition and citral content in lemongrass (Cymbopogon citratus) essential oil at three maturity stages. Afr. J. Biotechnol., 2012, 11(11), 2685-2693.
Abdellatif, F.; Hassani, A. Chemical composition of the essential oils from leaves of Melissa officinalis extracted by hydrodistillation, steam distillation, organic solvent and microwave hydrodistillation. J. Mater. Environ. Sci., 2015, 6(1), 207-213.
Baser, K.H.C.; Kirimer, N.; Ermin, N.; Kürkçüoglu, M.; Tümen, G. Essential oils from four chemotypes of Thymus zygioides Griseb. var. lycaonicus (Celak) Ronniger. J. Essent. Oil Res., 1996, 8(6), 615-618.
Tzakou, O.; Verykokidou, E.; Roussis, V.; Chinou, I. Chemical composition and antibacterial properties of Thymus longicaulis subsp. chaoubardii oils: Three chemotypes in the same population. J. Essent. Oil Res., 1998, 10(1), 97-99.
Avetisyan, A.; Markosian, A.; Petrosyan, M.; Sahakyan, N.; Babayan, A.; Aloyan, S.; Trchounian, A. Chemical composition and some biological activities of the essential oils from basil Ocimum different cultivars. BMC Complement. Altern. Med., 2017, 17(1), 1-8.
Skaltsa, H.D.; Lazari, D.M.; Mavromati, A.S.; Tiligada, E.A.; Constantinidis, T.A. Composition and antimicrobial activity of the essential oil of Scutellaria albida ssp. albida from Greece. Planta Med., 2000, 66(7), 672-674.
Stahl-Biskup, E. Das ätherische Öl norwegischer Thymusarten. I. Thymus praecox ssp. arcticus. Planta Med., 1986, 52, 36-38.
Mehmood, F.; Khan, Z.U.D.; Manzoor, F.; Jamil, M. Analysis of Insect toxicity and repellent activity of Phytochemicals from “Skimmia laureola, Nair” against “Black garden ant, Lasius niger” of Pakistan. Pak. J. Pharm. Sci., 2016, 29(3), 789-793.
Moghaddam, M.; Pourbaige, M.; Tabar, H.K.; Farhadi, N.; Hosseini, S.M.A. Composition and antifungal activity of peppermint (Mentha piperita) essential oil from Iran. J. Essent. Oil Bear. Pl., 2013, 16(4), 506-512.
Verma, R.S.; Rahman, L.; Verma, R.K.; Chauhan, A.; Yadav, A.K.; Singh, A. Essential oil composition of menthol mint (Mentha arvensis) and peppermint (Mentha piperita) cultivars at different stages of plant growth from Kumaon region of Western Himalaya. Open Access J. J. Med. Aromat. Plants, 2010, 1(1), 13-18.
Souza, M.A.; Lemos, M.J.; Brito, D.M.; Fernandes, M.S.; Castro, R.N.; Souza, S.R. Production and quality of menthol Mint essential oil and antifungal and antigerminative activity. Am. J. Plant Sci., 2014, 5(21), 3311-3318.
Gretšušnikova, T.; Järvan, K.; Orav, A.; Koel, M. Comparative analysis of the composition of the essential oil from the shoots, leaves and stems the wild Ledum palustre L. from Estonia. Procedia Chem., 2010, 2(1), 168-173.
El-Kamali, H.H.; Burham, B.O.; El-Egami, A.A. Essential oil composition of internal fruit peel of Citrus paradisi from Sudan. Am. Res. Thoughts, 2015, 1(9), 2079-2085.
Bellahsene, C.; Bendahou, M.; Khadir, A.; Zenati, F.; Benbelaïd, F.; Aissaoui, N.; Muselli, A.; Costa, J. Antimicrobial activity and chemical composition of essential oil and hydrosol extract of Nepeta nepetella subsp. amethystina (Poir.) Briq. from Algeria. J. Appl. Pharm. Sci., 2015, 5(9), 21-25.
De-Pooter, H.L.; Nicolai, B.; De Buyck, L.F.; Goetghebeur, P.; Schamp, N.M. The essential oil of Nepeta nuda identification of a new nepetalactone diastereoisomer. Phytochemistry, 1987, 26(8), 2311-2314.
Tepe, B.; Sokmen, M.; Akpulat, H.A.; Daferera, D.; Polissiou, M.; Sokmen, A. Antioxidative activity of the essential oils of Thymus sipyleus subsp. sipyleus var. sipyleus and Thymus sipyleus subsp. sipyleus var. rosulans. J. Food Eng., 2005, 66(4), 447-454.
Djihane, B.; Wafa, N.; Elkhamssa, S.; Maria, A.E.; Mihoub, Z.M. Chemical constituents of Helichrysum italicum (Roth) G. Don essential oil and their antimicrobial activity against Gram-positive and Gram-negative bacteria, filamentous fungi and Candida albicans. Saudi Pharm. J., 2017, 25(5), 780-787.
Kaya, A.; Demirci, B.; Baser, K.H.C. The composition of the essential oil of Stachys iberica subsp. stenostachya growing in Turkey. Chem. Nat. Compd., 2001, 37(4), 326-328.
Hojjati, M.; Barzegar, H. Chemical composition and biological activities of Lemon (Citrus limon) leaf essential oil. Nutr. Food Sci. Res., 2017, 4(4), 15-24.
Tabanca, N.; Demirci, B.; Ali, A.; Ali, Z.; Blythe, E.K.; Khan, I.A. Essential oils of green and red Perilla frutescens as potential sources of compounds for mosquito management. Ind. Crops Prod., 2015, 2015(65), 36-44.
Donald, G.R.; Fernandes, P.D.; Boylan, F. Antinociceptive Activity of Zanthoxylum piperitum DC. Essential Oil. Evid. Based Complementary Altern. Med., 2016, 1-8.
Krastanov, I. Chemical composition and antioxidant properties of juniper berry (Juniperus communis L.) essential oil. Bulg. J. Agric. Sci., 2014, 20(2), 227-237.
Sonboli, A.; Salehi, P.; Ebrahimi, S.N. Essential oil composition and antibacterial activity of the leaves of Stachys schtschegleevii from Iran. Chem. Nat. Compd., 2005, 41(2), 171-174.
Alan, S.; Kürkçüoglu, M.; Baser, K.H.C. Composition of essential oils of Calamintha nepeta (L.) Savi subsp. nepeta and Calamintha nepeta (L.) Savi subsp. glandulosa (Req.) PW Ball. Asian J. Chem., 2011, 23(6), 2357-2360.
Obolskiy, D.; Pischel, I.; Feistel, B.; Glotov, N.; Heinrich, M. Artemisia dracunculus L. (tarragon): a critical review of its traditional use, chemical composition, pharmacology, and safety. J. Agric. Food Chem., 2011, 59(21), 11367-11384.
Babazadeh Darjazi, B. Comparison of leaf components of sweet orange and sour orange (Citrus sp.). Int. J. Adv. Biol. Biomed. Res., 2013, 1(12), 1558-1568.
Mamedova, S.A. Essential oil of Arischrada dracocephaloides. Chem. Nat. Compd., 1997, 33(5), 593-594.
Satyal, P.; Murray, B.L.; McFeeters, R.L.; Setzer, W.N. Essential oil characterization of Thymus vulgaris from various geographical locations. Foods, 2016, 5(4), 1-12.
Rocha, D.S.; Silva, J.M.D.; Navarro, D.M.D.A.F.; Camara, C.A.G.; Lira, C.S.D.; Ramos, C.S. Potential antimicrobial and chemical composition of essential oils from Piper caldense tissues. J. Mex. Chem. Soc., 2016, 60(3), 148-151.
Marques, D.D.; Sartori, R.A.; Lemos, T.L.G.; Machado, L.L.; Souza, J.S.N.D.; Monte, F.J.Q. Chemical composition of the essential oils from two subspecies of Protium heptaphyllum. Acta Amazon., 2010, 40(1), 227-230.
Khan, M.; Mousa, A.A.; Syamasundar, K.V.; Alkhathlan, H.Z. Determination of chemical constituents of leaf and stem essential oils of Artemisia monosperma from central Saudi Arabia. Nat. Prod. Commun., 2012, 7(8), 1079-1082.
Baser, K.H.C.; Özek, T.; Kirimer, N.; Tümen, G. The occurrence of three chemotypes of Thymus longicaulis C. Presl. subsp. longicaulis in the same population. J. Essent. Oil Res., 1993, 5(3), 291-295.
Kontogiorgis, C.; Mpompou Evlampia, M.; Papajani-Toska, V.; Hadjipavlou Litina, D.; Lazari, D. Chemical composition and antioxidant activity of the essential oils isolated from Greek and Albanian Thymus species. J. Chem. Pharm. Res., 2016, 8(9), 180-184.
Vetvicka, V.; Vetvickova, J. Essential oils from thyme (Thymus vulgaris): Chemical composition and biological effects in mouse model. J. Med. Food, 2016, 19(12), 1180-1187.
Asressu, K.H.; Tesema, T.K. Chemical and antimicrobial investigations on essential oil of Rosmarinus officinalis leaves grown in ethiopia and comparison with other countries. J. Appl. Pharm. Sci., 2014, 6(2), 132-142.

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Year: 2020
Published on: 17 July, 2020
Page: [958 - 974]
Pages: 17
DOI: 10.2174/1389557520666200122144703
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