Biological Activities and Safety of Citrus spp. Essential Oils

International Journal of Molecular Sciences - Tập 19 Số 7 - Trang 1966
Noura S. Dosoky1, William N. Setzer1,2
1Aromatic Plant Research Center, 230 N 1200 E, Suite 102, Lehi, UT 84043, USA
2Department of Chemistry, University of Alabama in Huntsville, Huntsville, AL 35899, USA

Tóm tắt

Citrus fruits have been a commercially important crop for thousands of years. In addition, Citrus essential oils are valuable in the perfume, food, and beverage industries, and have also enjoyed use as aromatherapy and medicinal agents. This review summarizes the important biological activities and safety considerations of the essential oils of sweet orange (Citrus sinensis), bitter orange (Citrus aurantium), neroli (Citrus aurantium), orange petitgrain (Citrus aurantium), mandarin (Citrus reticulata), lemon (Citrus limon), lime (Citrus aurantifolia), grapefruit (Citrus × paradisi), bergamot (Citrus bergamia), Yuzu (Citrus junos), and kumquat (Citrus japonica).

Từ khóa


Tài liệu tham khảo

Moore, 2001, Oranges and lemons: Clues to the taxonomy of Citrus from molecular markers, Trends Genet., 17, 536, 10.1016/S0168-9525(01)02442-8

Mabberley, 2004, Citrus (Rutaceae): A review of recent advances in etymology, systematics and medical applications, Blumea, 49, 481, 10.3767/000651904X484432

Anwar, 2008, Physico-chemical characteristics of citrus seeds and seed oils from Pakistan, J. Am. Oil Chem. Soc., 85, 321, 10.1007/s11746-008-1204-3

Sharma, 2017, Converting citrus wastes into value-added products: Economic and environmently friendly approaches, Nutrition, 34, 29, 10.1016/j.nut.2016.09.006

Siles, 2010, Biomethanization of orange peel waste, Bioresour. Technol., 101, 8993, 10.1016/j.biortech.2010.06.133

Rezzadori, 2012, Proposals for the residues recovery: Orange waste as raw material for new products, Food Bioprod. Process., 90, 606, 10.1016/j.fbp.2012.06.002

Ferhat, 2006, An improved microwave Clevenger apparatus for distillation of essential oils from orange peel, J. Chromatogr. A, 1112, 121, 10.1016/j.chroma.2005.12.030

Tisserand, R., and Young, R. (2014). Essential Oil Safety, Elsevier. [2nd ed.].

Mitropoulou, 2017, Citrus medica essential oil exhibits significant antimicrobial and antiproliferative activity, LWT Food Sci. Technol., 84, 344, 10.1016/j.lwt.2017.05.036

2008, Antifungal activity of lemon (Citrus limon L.), mandarin (Citrus reticulata L.), grapefruit (Citrus paradisi L.) and orange (Citrus sinensis L.) essential oils, Food Control, 19, 1130, 10.1016/j.foodcont.2007.12.003

Ali, N., Chhetri, B., Dosoky, N., Shari, K., Al-Fahad, A., Wessjohann, L., and Setzer, W. (2017). Antimicrobial, antioxidant, and cytotoxic activities of Ocimum forskolei and Teucrium yemense (Lamiaceae) essential oils. Medicines, 4.

Yu, 2017, D-limonene exhibits anti-inflammatory and antioxidant properties in an ulcerative colitis rat model via regulation of iNOS, COX-2, PGE2 and ERK signaling pathways, Mol. Med. Rep., 15, 2339, 10.3892/mmr.2017.6241

Roberto, 2010, Antioxidant activity of limonene on normal murine lymphocytes: Relation to H2O2 modulation and cell proliferation, Basic Clin. Pharmacol. Toxicol., 106, 38, 10.1111/j.1742-7843.2009.00467.x

Kostova, 2011, Coumarins as antioxidants, Curr. Med. Chem., 18, 3929, 10.2174/092986711803414395

Caccioni, 1998, Relationship between volatile components of citrus fruit essential oils and antimicrobial action on Penicillium digitatum and Penicillium italicum, Int. J. Food Microbiol., 43, 73, 10.1016/S0168-1605(98)00099-3

Siragusa, 2006, Characterization of five sour orange clones through molecular markers and leaf essential oils analysis, Sci. Hortic., 109, 54, 10.1016/j.scienta.2006.03.002

Dosoky, 2016, Phytochemical and biological investigations of Conradina canescens, Nat. Prod. Commun., 11, 25

Dosoky, 2014, Identification of essential oil components from Conradina canescens, Am. J. Essent. Oils Nat. Prod., 2, 24

da Silva, J.K., da Trindade, R., Moreira, E.C., Maia, J.G.S., Dosoky, N.S., Miller, R.S., Cseke, L.J., and Setzer, W.N. (2017). Chemical diversity, biological activity, and genetic aspects of three Ocotea species from the Amazon. Int. J. Mol. Sci., 18.

Ammar, 2012, Chemical composition and in vitro antimicrobial and antioxidant activities of Citrus aurantium L. flowers essential oil (Neroli oil), Pak. J. Biol. Sci., 15, 1034, 10.3923/pjbs.2012.1034.1040

Zhu, L.F., Li, Y.H., Li, B.L., Lu, B.Y., and Xia, N.H. (1993). Aromatic Plants and Their Essential Constitutes, South China Inst. Bot., Chinese Academy of Sciences, Peace Book Co.

Kubeczka, K.-H. (2002). Essential Oils Analysis by Capillary Gas Chromatography and Carbon-13 NMR Spectroscopy, Wiley.

Pino, 2001, Comparative investigation of the distilled lime oils (Citrus aurantifolia Swingle and Citrus latifolia Tanaka) from Cuba, J. Essent. Oil Res., 13, 179, 10.1080/10412905.2001.9699653

Dugo, 1999, Oxygen heterocyclic compounds of bergamot essential oils, Riv. Ital. EPPOS, 27, 31

Verzera, 1998, The composition of the volatile fraction of calabrian bergamot essential oil, Riv. Ital. EPPOS, 25, 17

Dugo, 1999, Identification of minor oxygen heterocyclic compounds of citrus essential oils by liquid chromatography-atmospheric pressure chemical ionisation mass spectrometry, J. Liq. Chromatogr. Relat. Technol., 22, 2991, 10.1081/JLC-100102073

Sawamura, 2009, Determination of bergapten in Japanese citrus essential oils, Jpn. J. Aromather., 9, 30

Hata, 2003, Induction of apoptosis by Citrus paradisi essential oil in human leukemic (HL-60) cells, In Vivo, 17, 553

Jayaprakasha, 2012, D-limonene rich volatile oil from blood oranges inhibits angiogenesis, metastasis and cell death in human colon cancer cells, Life Sci., 91, 429, 10.1016/j.lfs.2012.08.016

Igarashi, 2014, Effects of olfactory stimulation with rose and orange oil on prefrontal cortex activity, Complement. Ther. Med., 22, 1027, 10.1016/j.ctim.2014.09.003

Goes, 2012, Effect of sweet orange aroma on experimental anxiety in humans, J. Altern. Complement. Med., 18, 798, 10.1089/acm.2011.0551

Faturi, 2010, Anxiolytic-like effect of sweet orange aroma in Wistar rats, Prog. Neuro-Psychopharmacol. Biol. Psychiatry, 34, 605, 10.1016/j.pnpbp.2010.02.020

Lehrner, 2000, Ambient odor of orange in a dental office reduces anxiety and improves mood in female patients, Physiol. Behav., 71, 83, 10.1016/S0031-9384(00)00308-5

Yip, 2008, An experimental study on the effectiveness of massage with aromatic ginger and orange essential oil for moderate-to-severe knee pain among the elderly in Hong Kong, Complement. Ther. Med., 16, 131, 10.1016/j.ctim.2007.12.003

Bodake, 2002, Chemopreventive effect of orange oil on the development of hepatic preneoplastic lesions induced by N-nitrosodiethylamine in rats: An ultrastructural study, Indian J. Exp. Biol., 40, 245

Homburger, 1971, Inhibition of murine subcutaneous and intravenous benzo(rst)pentaphene carcinogenesis by sweet orange oils and d-limonene, Oncology, 25, 1, 10.1159/000224548

Asjad, 2013, Phenol, flavonoid contents and antioxidant activity of six common citrus plants in Pakistan, J. Pharm. Cosmet. Sci., 1, 1

Rimini, 2014, The use of thyme and orange essential oils blend to improve quality traits of marinated chicken meat, Poult. Sci., 93, 2096, 10.3382/ps.2013-03601

Matiz, 2012, Effectiveness of antimicrobial formulations for acne based on orange (Citrus sinensis) and sweet basil (Ocimum basilicum L.) essential oils, Biomedica, 32, 125

Franco-Vega, A., Reyes-Jurado, F., Cardoso-Ugarte, G.A., Sosa-Morales, M.E., Palou, E., and Lopez-Malo, A. (2015). Sweet Orange (Citrus Sinensis) Oils, Elsevier Inc.

Settani, 2012, Inhibition of foodborne pathogen bacteria by essential oils extracted from citrus fruits cultivated in Sicily, Food Control, 26, 326, 10.1016/j.foodcont.2012.01.050

Lin, 2010, Determination of bactericidal efficacy of essential oil extracted from orange peel on the food contact surfaces, Food Control, 21, 1710, 10.1016/j.foodcont.2010.06.008

Bourgou, 2012, Changes of peel essential oil composition of four Tunisian citrus during fruit maturation, Sci. World J., 2012, 528593, 10.1100/2012/528593

Singh, 2010, Chemical profile, antifungal, antiaflatoxigenic and antioxidant activity of Citrus maxima Burm. and Citrus sinensis (L.) Osbeck essential oils and their cyclic monoterpene, dl-limonene, Food Chem. Toxicol., 48, 1734, 10.1016/j.fct.2010.04.001

Sharma, 2008, Effects of Citrus sinensis (L.) Osbeck epicarp essential oil on growth and morphogenesis of Aspergillus niger (L.) Van Tieghem, Microbiol. Res., 163, 337, 10.1016/j.micres.2006.06.009

Lalamia, 2015, Larvicidal activity of essential oils of Citrus sinensis and Citrus aurantium (Rutaceae) cultivated in Morocco against the malaria vector Anopheles labranchiae (Diptera: Culicidae), Asian Pac. J. Trop. Dis., 5, 458, 10.1016/S2222-1808(15)60815-5

Silva, 2015, β-Cyclodextrin inclusion complexes containing Citrus sinensis (L.) Osbeck essential oil: An alternative to control Aedes aegypti larvae, Thermochim. Acta, 608, 14, 10.1016/j.tca.2015.04.001

Rossi, 2013, Fumigant toxicity of Citrus sinensis essential oil on Musca domestica L. adults in the absence and presence of a P450 inhibitor, Acta Trop., 127, 33, 10.1016/j.actatropica.2013.03.009

Ezeonu, 2001, Insecticidal properties of volatile extracts of orange peels, Bioresour. Technol., 76, 273, 10.1016/S0960-8524(00)00120-6

Raina, 2007, Effect of orange oil extract on the Formosan subterranean termite (Isoptera: Rhinotermitidae), J. Econ. Entomol., 100, 880, 10.1093/jee/100.3.880

Domingues, 2015, Anthelmintic activity in vitro of Citrus sinensis and Melaleuca quinquenervia essential oil from Cuba on Haemonchus contortus, Ind. Crop. Prod., 76, 647, 10.1016/j.indcrop.2015.07.056

Acar, 2015, Evaluation of the effects of essential oil extracted from sweet orange peel (Citrus sinensis) on growth rate of tilapia (Oreochromis mossambicus) and possible disease resistance against Streptococcus iniae, Aquaculture, 437, 282, 10.1016/j.aquaculture.2014.12.015

Anwar, S., Ahmed, N., Speciale, A., Cimino, F., and Saija, A. (2015). Bitter Orange (Citrus Aurantium L.) Oils, Elsevier Inc.

Costa, 2002, Anxiolytic and sedative effects of extracts and essential oil from Citrus aurantium L., Biol. Pharm. Bull., 25, 1629, 10.1248/bpb.25.1629

Costa, 2006, Effects of the essential oil from Citrus aurantium L. in experimental anxiety models in mice, Life Sci., 78, 1720, 10.1016/j.lfs.2005.08.004

Pimenta, 2016, Anxiolytic effect of Citrus aurantium L. on patients with chronic myeloid leukemia, Phyther. Res., 30, 613, 10.1002/ptr.5566

Costa, C.A.R.A., Cury, T.C., Cassettari, B.O., Takahira, R.K., Florio, J.C., and Costa, M. (2013). Citrus aurantium L. essential oil exhibits anxiolytic-like activity mediated by 5-HT1A-receptors and reduces cholesterol after repeated oral treatment. BMC Complement. Altern. Med., 13.

Yi, 2011, Involvement of monoaminergic systems in the antidepressant like effect of nobiletin, Physiol. Behav., 102, 1, 10.1016/j.physbeh.2010.10.008

Namazi, 2014, Effects of Citrus aurantium (bitter orange) on the severity of first-stage labor pain, Iran. J. Pharm. Res., 13, 1011

Moraes, 2009, Effects of limonene and essential oil from Citrus aurantium on gastric mucosa: Role of prostaglandins and gastric mucus secretion, Chem. Biol. Interact., 180, 499, 10.1016/j.cbi.2009.04.006

Lv, 2012, Effect of orange peel essential oil on oxidative stress in AOM animals, Int. J. Biol. Macromol., 50, 1144, 10.1016/j.ijbiomac.2012.02.002

Ullah, 2014, Nephroprotective potentials of Citrus aurantium: A prospective pharmacological study on experimental models, Pak. J. Pharm. Sci., 27, 505

Friedman, 2004, Antibacterial activities of plant essential oils and their components against Escherichia coli O157:H7 and Salmonella enterica in apple juice, J. Agric. Food Chem., 52, 6042, 10.1021/jf0495340

Iturriaga, 2012, Antimicrobial assays of natural extracts and their inhibitory effect against Listeria innocua and fish spoilage bacteria, after incorporation into biopolymer edible films, Int. J. Food Microbiol., 158, 58, 10.1016/j.ijfoodmicro.2012.07.001

Oliveira, 2014, The antimicrobial effects of Citrus limonum and Citrus aurantium essential oils on multi-species biofilms, Braz. Oral Res., 28, 22, 10.1590/S1806-83242013005000024

Ramadan, 1996, Oil of bitter orange: New topical antifungal agent, Int. J. Dermatol., 35, 448, 10.1111/j.1365-4362.1996.tb03032.x

Zarrad, 2015, Ben Chemical composition, fumigant and anti-acetylcholinesterase activity of the Tunisian Citrus aurantium L. essential oils, Ind. Crop. Prod., 76, 121, 10.1016/j.indcrop.2015.06.039

Battaglia, S. (2003). The Complete Guide to Aromatherapy Brisbane.

Akhlaghi, 2011, Citrus aurantium blossom and preoperative anxiety, Rev. Bras. Anestesiol., 61, 702, 10.1016/S0034-7094(11)70079-4

Kamalifard, 2018, Comparison of the effect of lavender and bitter orange on anxiety in postmenopausal women: A triple-blind, randomized, controlled clinical trial, Complement. Ther. Clin. Pract., 31, 132, 10.1016/j.ctcp.2018.02.004

Azanchi, 2014, Anticonvulsant activity of Citrus aurantium blossom essential oil (neroli): Involvment of the GABAergic system, Nat. Prod. Commun., 9, 1615

Rahnama, 2014, Antiamnesic activity of Citrus aurantium flowers extract against scopolamine-induced memory impairments in rats, Neurol. Sci., 36, 553, 10.1007/s10072-014-1991-2

Khodabakhsh, 2015, Analgesic and anti-inflammatory activities of Citrus aurantium L. blossoms essential oil (neroli): Involvement of the nitric oxide/cyclic-guanosine monophosphate pathway, J. Nat. Med., 69, 324, 10.1007/s11418-015-0896-6

Choi, S.Y., Kang, P., Lee, H.S., and Seol, G.H. (2014). Effects of inhalation of essential oil of Citrus aurantium L. var. amara on menopausal symptoms, stress, and estrogen in postmenopausal women: A randomized controlled trial. Evid.-Based Complement. Altern. Med., 2014.

Heydari, 2018, Investigation of the effect of aromatherapy with Citrus aurantium blossom essential oil on premenstrual syndrome in university students: A clinical trial study, Complement. Ther. Clin. Pract., 32, 1, 10.1016/j.ctcp.2018.04.006

Kang, 2016, Endothelium- and smooth muscle-dependent vasodilator effects of Citrus aurantium L. var. amara: Focus on Ca2+ modulation, Biomed. Pharmacother., 82, 467, 10.1016/j.biopha.2016.05.030

Kim, 2012, Essential oil inhalation on blood pressure and salivary cortisol levels in prehypertensive and hypertensive subjects, Evid.-Based Complement. Altern. Med., 2012, 984203, 10.1155/2012/984203

Ao, 2008, Singlet oxygen scavenging activity and cytotoxicity of essential oils from Rutaceae, J. Clin. Biochem. Nutr., 43, 6, 10.3164/jcbn.2008037

Hamdi, 2013, Characterization of essential oil from Citrus aurantium L. flowers: Antimicrobial and antioxidant activities, J. Oleo Sci., 62, 763, 10.5650/jos.62.763

Sarrou, 2013, Volatile constituents and antioxidant activity of peel, flowers and leaf oils of Citrus aurantium L. growing in Greece, Molecules, 18, 10639, 10.3390/molecules180910639

Ellouze, 2012, Season’s variation impact on Citrus aurantium leaves essential oil: Chemical composition and biological activities, J. Food Sci., 77, 1, 10.1111/j.1750-3841.2012.02846.x

Zhou, 2012, Preventive effects of Citrus reticulata essential oil on bleomycin-induced pulmonary fibrosis in rats and the mechanism, J. Chin. Integr. Med., 10, 200, 10.3736/jcim20120211

Yi, 2018, Evaluation of mechanical-pressed essential oil from Nanfeng mandarin (Citrus reticulata Blanco cv. Kinokuni) as a food preservative based on antimicrobial and antioxidant activities, LWT Food Sci. Technol., 95, 346, 10.1016/j.lwt.2018.05.011

Tao, 2014, Anti-fungal activity of Citrus reticulata Blanco essential oil against Penicillium italicum and Penicillium digitatum, Food Chem., 153, 265, 10.1016/j.foodchem.2013.12.070

Matan, 2008, Antifungal activities of anise oil, lime oil, and tangerine oil against molds on rubberwood (Hevea brasiliensis), Int. Biodeterior. Biodegrad., 62, 75, 10.1016/j.ibiod.2007.07.014

Wu, 2014, Antifungal action and inhibitory mechanism of polymethoxylated flavones from Citrus reticulata Blanco peel against Aspergillus niger, Food Control, 35, 354, 10.1016/j.foodcont.2013.07.027

Chutia, 2009, Antifungal activity and chemical composition of Citrus reticulata Blanco essential oil against phytopathogens from North East India, LWT Food Sci. Technol., 42, 777, 10.1016/j.lwt.2008.09.015

Komiya, 2006, Lemon oil vapor causes an anti-stress effect via modulating the 5-HT and DA activities in mice, Behav. Brain Res., 172, 240, 10.1016/j.bbr.2006.05.006

Ogeturk, 2010, Effects of lemon essential oil aroma on the learning behaviors of rats, Neurosciences, 15, 292

Zu, 2010, Activities of ten essential oils towards Propionibacterium acnes and PC-3, A-549 and MCF-7 cancer cells, Molecules, 15, 3200, 10.3390/molecules15053200

Wattenberg, 1991, Inhibition of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone carcinogenesis in mice by D-limonene and citrus fruit oils, Carcinogenesis, 12, 115, 10.1093/carcin/12.1.115

Niijima, 2003, Effect of Olfactory stimulation with flavor of grapefruit oil and lemon oil on the activity of sympathetic branch in the white adipose tissue of the epididymis, Exp. Biol. Med., 228, 1190, 10.1177/153537020322801014

Feitosa, 2011, Antioxidant activity of Citrus limon essential oil in mouse hippocampus, Pharm. Biol., 49, 709, 10.3109/13880209.2010.541924

Choi, 2000, Radical-scavenging activities of citrus essential oils and their components: Detection using 1,1-diphenyl-2-picrylhydrazyl, J. Agric. Food Chem., 48, 4156, 10.1021/jf000227d

De Freitas, R.M., Campêlo, L.M.L., de Almeida, A.A.C., de Freitas, R.L.M., Cerqueira, G.S., de Sousa, G.F., Saldanha, G.B., and Feitosa, C.M. (2011). Antioxidant and antinociceptive effects of Citrus limon essential oil in mice. J. Biomed. Biotechnol.

Ceccarelli, 2004, Effects of long-term exposure of lemon essential oil odor on behavioral, hormonal and neuronal parameters in male and female rats, Brain Res., 1001, 78, 10.1016/j.brainres.2003.10.063

Ceccarelli, 2002, Sex differences in the citrus lemon essential oil-induced increase of hippocampal acetylcholine release in rats exposed to a persistent painful stimulation, Neurosci. Lett., 330, 25, 10.1016/S0304-3940(02)00717-6

Ikeda, 2014, Contribution of anterior cingulate cortex and descending pain inhibitory system to analgesic effect of lemon odor in mice, Mol. Pain, 10, 14, 10.1186/1744-8069-10-14

Yavari Kia, P., Safajou, F., Shahnazi, M., and Nazemiyeh, H. (2014). The effect of lemon inhalation aromatherapy on nausea and vomiting of pregnancy: A double-blinded, randomized, controlled clinical trial. Iran. Red Crescent Med. J., 16.

Akpinar, 2005, The effects of olfactory stimuli on scholastic performance, Ir. J. Educ., 36, 86

Valgimigli, 2012, Lemon (Citrus limon, Burm.f.) essential oil enhances the trans-epidermal release of lipid-(A, E) and water-(B6, C) soluble vitamins from topical emulsions in reconstructed human epidermis, Int. J. Cosmet. Sci., 34, 347, 10.1111/j.1468-2494.2012.00725.x

2008, Antibacterial activity of lemon (Citrus limon L.), mandarin (Citrus reticulata L.), grapefruit (Citrus paradisi L.) and orange (Citrus sinensis L.) essential oils, J. Food Saf., 28, 567, 10.1111/j.1745-4565.2008.00131.x

Mohamady, 2011, In vitro antioxidant and antibacterial activities of essentials oils obtained from Egyptian aromatic plants, Food Control, 22, 1715, 10.1016/j.foodcont.2011.04.003

Oshaghi, 2003, Repellent effect of extracts and essential oils of Citrus limon (Rutaceae) and Melissa officinalis (Labiatae) against main malaria vector, Anopheles stephensi (Diptera: Culicidae), Iran. J. Public Health, 32, 47

Aboelhadid, 2016, In vitro and in vivo effect of Citrus limon essential oil against sarcoptic mange in rabbits, Parasitol. Res., 115, 3013, 10.1007/s00436-016-5056-8

Asnaashari, 2010, Essential oil from Citrus aurantifolia prevents ketotifen-induced weight-gain in mice, Phyther. Res., 24, 1893, 10.1002/ptr.3227

Shafreen, R.B., Lubinska, M., Różańska, A., Dymerski, T., Namieśnik, J., Katrich, E., and Gorinstein, S. (2018). Human serum interactions with phenolic and aroma substances of Kaffir (Citrus hystrix) and Key lime (Citrus aurantifolia) juices. J. Lumin.

Spadaro, 2012, Volatile composition and biological activity of key lime Citrus aurantifolia essential oil, Nat. Prod. Commun., 7, 1523

Tundis, 2012, Comparative study on the antioxidant capacity and cholinesterase inhibitory activity of Citrus aurantifolia Swingle, C. aurantium L., and C. bergamia Risso and Poit. peel essential oils, J. Food Sci., 77, H40, 10.1111/j.1750-3841.2011.02511.x

Amorim, J.L., Simas, D.L.R., Pinheiro, M.M.G., Moreno, D.S.A., Alviano, C.S., Da Silva, A.J.R., and Fernandes, P.D. (2016). Anti-inflammatory properties and chemical characterization of the essential oils of four Citrus species. PLoS ONE, 11.

Cruz-Valenzuela, M.R., Tapia-Rodriguez, M.R., Vazquez-Armenta, F.J., Silva-Espinoza, B.A., and Ayala-Zavala, J.F. (2015). Lime (Citrus aurantifolia) Oils, Elsevier Inc.

Ruberto, G. (2002). Analysis of Volatile Components of Citrus Fruit Essential Oils. Analysis of Taste and Aroma, Springer.

Fagodia, 2017, Phytotoxicity and cytotoxicity of Citrus aurantiifolia essential oil and its major constituents: Limonene and citral, Ind. Crop. Prod., 108, 708, 10.1016/j.indcrop.2017.07.005

Fouad, 2017, Chemical composition and bioactivity of peel oils from Citrus aurantiifolia and Citrus reticulata and enantiomers of their major constituent against Sitophilus zeamais (Coleoptera: Curculionidae), J. Stored Prod. Res., 73, 30, 10.1016/j.jspr.2017.06.001

Nagai, 2014, Olfactory stimulatory with grapefruit and lavender oils change autonomic nerve activity and physiological function, Auton. Neurosci. Basic Clin., 185, 29, 10.1016/j.autneu.2014.06.005

Stiles, K.G. (2017). The Essential Oils Complete Reference Guide: Over 250 Recipes for Natural Wholesome Aromatherapy, Page Street Publishing.

Lim, T.K. (2012). Edible Medicinal and Non-Medicinal Plants, Springer Science & Business Media.

Okunowo, 2013, Essential oil of grape fruit (Citrus paradisi) peels and its antimicrobial activities, Am. J. Plant Sci., 4, 1, 10.4236/ajps.2013.47A2001

2016, Antifungal effect of Citrus paradisi “grapefruit”on strains of Candida albicans isolated from patients with denture stomatitis, Rev. Estomatol. Hered., 26, 78

Tirillini, B. (2000). Grapefruit: The last decade acquisitions. Fitoterapia, 71.

Ruiz, 2014, Toxic effect of citrus peel constituents on Anastrepha fraterculus Wiedemann and Ceratitis capitata Wiedemann immature stages, J. Agric. Food Chem., 62, 10084, 10.1021/jf503063b

Ivoke, 2013, Effects of grapefruit (Citrus paradisi MACF) (Rutaceae) peel oil against developmental stages of Aedes aegypti (Diptera: Culicidae), Southeast Asian J. Trop. Med. Public Health, 44, 970

Sedaghat, 2016, Chemical compositions of the peel essential oil of Citrus aurantium and its natural larvicidal activity against the malaria vector Anopheles stephensi (Diptera: Culicidae) in comparison with Citrus paradisi, J. Arthropod Borne Dis., 10, 577

Alcala, 2016, Anticoccidial efficacy of naringenin and a grapefruit peel extract in growing lambs naturally-infected with Eimeria spp., Vet. Parasitol., 232, 58, 10.1016/j.vetpar.2016.11.009

Russo, R., Cassiano, M.G.V., Ciociaro, A., Adornetto, A., Varano, G.P., Chiappini, C., Berliocchi, L., Tassorelli, C., Bagetta, G., and Corasaniti, M.T. (2014). Role of d-limonene in autophagy induced by bergamot essential oil in SH-SY5Y neuroblastoma cells. PLoS ONE, 9.

Moysan, 1993, Evaluation of phototoxic and photogenotoxic risk associated with the use of photosensitizers in suntan preparations: Application to tanning preparations containing bergamot oil, Skin Pharmacol. Physiol., 6, 282, 10.1159/000211151

Amantea, 2016, Rational basis for the use of bergamot essential oil in complementary medicine to treat chronic pain, Mini-Rev. Med. Chem., 16, 721, 10.2174/1389557516666160321113913

Lauro, 2016, The protective role of bergamot polyphenolic fraction on several animal models of pain, PharmaNutrition, 4, S35, 10.1016/j.phanu.2016.04.001

Sakurada, 2011, Intraplantar injection of bergamot essential oil induces peripheral antinociception mediated by opioid mechanism, Pharmacol. Biochem. Behav., 97, 436, 10.1016/j.pbb.2010.09.020

Katsuyama, 2015, Effect of plantar subcutaneous administration of bergamot essential oil and linalool on formalin-induced nociceptive behavior in mice, Biomed. Res., 36, 47, 10.2220/biomedres.36.47

Kuwahata, 2013, Peripherally injected linalool and bergamot essential oil attenuate mechanical allodynia via inhibiting spinal ERK phosphorylation, Pharmacol. Biochem. Behav., 103, 735, 10.1016/j.pbb.2012.11.003

Cosentino, 2014, The essential oil of bergamot stimulates reactive oxygen species production in human polymorphonuclear leukocytes, Phyther. Res., 28, 1232, 10.1002/ptr.5121

Navarra, 2015, Effects of bergamot essential oil and its extractive fractions on SH-SY5Y human neuroblastoma cell growth, J. Pharm. Pharmacol., 67, 1042, 10.1111/jphp.12403

Berliocchi, 2011, Toxic profile of bergamot essential oil on survival and proliferation of SH-SY5Y neuroblastoma cells, Food Chem. Toxicol., 49, 2780, 10.1016/j.fct.2011.08.017

Celia, 2013, Anticancer activity of liposomal bergamot essential oil (BEO) on human neuroblastoma cells, Colloids Surf. B Biointerfaces, 112, 548, 10.1016/j.colsurfb.2013.09.017

Sawamura, M. (2010). Citrus Essential Oils: Flavor and Fragrance, Wiley.

Bagetta, 2010, Neuropharmacology of the essential oil of bergamot, Fitoterapia, 81, 453, 10.1016/j.fitote.2010.01.013

Amantea, 2009, Prevention of glutamate accumulation and upregulation of phospho-Akt may account for neuroprotection afforded by bergamot essential oil against brain injury induced by focal cerebral ischemia in rat, Int. Rev. Neurobiol., 85, 389, 10.1016/S0074-7742(09)85027-7

Saiyudthong, 2015, Effect of Inhaling bergamot oil on depression-related behaviors in chronic stressed rats, J. Med. Assoc. Thail., 98, S152

Saiyudthong, 2011, Acute effects of bergamot oil on anxiety-related behaviour and corticosterone level in rats, Phyther. Res., 25, 858, 10.1002/ptr.3325

Han, 2017, Bergamot (Citrus bergamia) essential oil inhalation improves positive feelings in the waiting room of a mental health treatment center: A pilot study, Phyther. Res., 31, 812, 10.1002/ptr.5806

Avila-Sosa, R., Navarro-Cruz, A.R., Sosa-Morales, M.E., López-Malo, A., and Palou, E. (2015). Bergamot (Citrus Bergamia) Oils, Elsevier Inc.

Kirbaslar, 2009, Antimicrobial activity of Turkish citrus peel oils, Pak. J. Bot., 41, 3207

Fisher, 2006, The effect of lemon, orange and bergamot essential oils and their components on the survival of Campylobacter jejuni, Escherichia coli O157, Listeria monocytogenes, Bacillus cereus and Staphylococcus aureus in vitro and in food systems, J. Appl. Microbiol., 101, 1232, 10.1111/j.1365-2672.2006.03035.x

2014, Antifungal activity of selected essential oils against fungi isolated from medicinal plant, Ind. Crop. Prod., 55, 116, 10.1016/j.indcrop.2014.02.011

Sanguinetti, 2007, In vitro activity of Citrus bergamia (bergamot) oil against clinical isolates of dermatophytes, J. Antimicrob. Chemother., 59, 305, 10.1093/jac/dkl473

Elsaeed, 2016, Randomized clinical trial on evaluation of the effect of bergamot oil on treatment of ring worm infection in calves and cats, Int. J. Infect. Dis., 45, 312, 10.1016/j.ijid.2016.02.683

Furneri, 2012, In vitro antimycoplasmal activity of Citrus bergamia essential oil and its major components, Eur. J. Med. Chem., 52, 66, 10.1016/j.ejmech.2012.03.005

Sawamura, 2005, Inhibitory effect of yuzu essential oil on the formation of N-nitrosodimethylamine in vegetables, J. Agric. Food Chem., 53, 4281, 10.1021/jf047816u

Hirota, 2010, Anti-inflammatory effects of limonene from yuzu (Citrus junos Tanaka) essential oil on eosinophils, J. Food Sci., 75, 20492298, 10.1111/j.1750-3841.2010.01541.x

Ueki, 2014, Effectiveness of aromatherapy in decreasing maternal anxiety for a sick child undergoing infusion in a paediatric clinic, Complement. Ther. Med., 22, 1019, 10.1016/j.ctim.2014.09.004

Matsumoto, 2016, Aromatic effects of a Japanese citrus fruit-yuzu (Citrus junos Sieb. ex Tanaka)-on psychoemotional states and autonomic nervous system activity during the menstrual cycle: A single-blind randomized controlled crossover study, Biopsychosoc. Med., 10, 11, 10.1186/s13030-016-0063-7

Matsumoto, 2017, Does Japanese citrus fruit yuzu (Citrus junos Sieb. ex Tanaka) fragrance have lavender-like therapeutic effects that alleviate premenstrual emotional symptoms? A single-blind randomized crossover Study, J. Altern. Complement. Med., 23, 461, 10.1089/acm.2016.0328

Kasahara, 1993, Suppressing effect of yuzu peel on the odor of Niboshi soup stock, Bull. Jpn. Soc. Sci. Fish., 59, 673, 10.2331/suisan.59.673

Kim, 2014, Citrus junos Tanaka peel extract attenuates experimental colitis and inhibits tumour growth in a mouse xenograft model, J. Funct. Foods, 8, 301, 10.1016/j.jff.2014.03.024

Hwang, 2013, Ethanol extract of Citrus junos Tanaka exerts hypocholesterolemic effect in mice fed a high cholesterol diet, Atherosclerosis, 241, e195, 10.1016/j.atherosclerosis.2015.04.948

Kim, 2013, Citrus junos Tanaka peel extract exerts antidiabetic effects via AMPK and PPAR-γboth in vitro and in vivo in mice fed a high-fat diet, Evid.-Based Complement. Altern. Med., 2013, 921012

Zang, 2014, Effects of yuzu (Citrus junos Siebold ex Tanaka) peel on the diet-induced obesity in a zebrafish model, J. Funct. Foods, 10, 499, 10.1016/j.jff.2014.08.002

Yu, 2011, Anti-platelet effects of yuzu extract and its component, Food Chem. Toxicol., 49, 3018, 10.1016/j.fct.2011.09.038

Yu, H.Y., Ahn, J.H., Park, S.W., and Jung, Y.-S. (2015). Preventive effect of yuzu and hesperidin on left ventricular remodeling and dysfunction in rat permanent left anterior descending coronary artery occlusion model. PLoS ONE, 10.

Jayaprakasha, 2012, Inhibition of prostate cancer (LNCaP) cell proliferation by volatile components from Nagami kumquats, Planta Med., 78, 974, 10.1055/s-0031-1298619

Nouri, 2016, Chemical constituents and antioxidant activity of essential oil and organic extract from the peel and kernel parts of Citrus japonica Thunb. (kumquat) from Iran, Nat. Prod. Res., 30, 1093, 10.1080/14786419.2015.1101692

Wang, 2012, Chemical composition and antimicrobial activity of the essential oil of kumquat (Fortunella crassifolia Swingle) peel, Int. J. Mol. Sci., 13, 3382, 10.3390/ijms13033382

Md Othman, S., Hassan, M., Nahar, L., Basar, N., Jamil, S., and Sarker, S. (2016). Essential Oils from the Malaysian Citrus (Rutaceae) medicinal plants. Medicines, 3.

Morrone, 2007, The essential oil of bergamot enhances the levels of amino acid neurotransmitters in the hippocampus of rat: Implication of monoterpene hydrocarbons, Pharmacol. Res., 55, 255, 10.1016/j.phrs.2006.11.010

Volpato, 2015, Effect of essential oil from Citrus aurantium in maternal reproductive outcome and fetal anomaly frequency in rats, An. Acad. Bras. Ciênc., 87, 407, 10.1590/0001-3765201520140354

Opdyke, 1974, Monographs on fragrance raw materials, Food Cosmet. Toxicol., 12, 807, 10.1016/0015-6264(74)90257-0

Naganuma, 1985, A study of the phototoxicity of lemon oil, Arch. Dermatol. Res., 278, 31, 10.1007/BF00412492

Rudzki, 1976, Sensitivity to 35 essential oils, Contact Dermat., 2, 196, 10.1111/j.1600-0536.1976.tb03026.x

Santucci, 1987, Contact dermatitis to fragrances, Contact Dermat., 16, 93, 10.1111/j.1600-0536.1987.tb01386.x

Menenghini, 1971, Additives, vehicles and active drugs of topical medicaments as causes of delayed-type allergic dermatitis, Dermatologica, 143, 137, 10.1159/000252183

Young, 1990, Phototumorigenesis studies of 5-methoxypsoralen in bergamot oil: Evaluation and modification of risk of human use in an albino mouse skin model, J. Photochem. Photobiol. B, 7, 231, 10.1016/1011-1344(90)85159-T

Opdyke, 1973, Fragrance raw materials Monographs, Food Cosmet. Toxicol., 11, 873, 10.1016/0015-6264(73)90154-5

Lawrence, B.M. (2005). The cutaneous effects of the common concretes and absolutes used in the perfume industry. The Antimicrobial/Biological Activity of Essential Oils, Allured.

Christensson, 2009, Air oxidation increases skin irritation from fragrance terpenes, Contact Dermat., 60, 32, 10.1111/j.1600-0536.2008.01471.x

Li, 2009, Unusual antioxidant behavior of alpha- and gamma-terpinene in protecting methyl linoleate, DNA, and erythrocyte, J. Agric. Food Chem., 57, 3943, 10.1021/jf803358g

Tisserand, R., and Balacs, T. (1999). Essential Oil Safety—A Guide for Health Care Professionals, Harcourt.

Cavanagh, 2002, Biological activities of lavender essential oil, Phyther. Res., 16, 301, 10.1002/ptr.1103

Williamson, 2007, An investigation and comparison of the bioactivity of selected essential oils on human lice and house dust mites, Fitoterapia, 78, 521, 10.1016/j.fitote.2007.06.001

Maia, 2016, Antioxidant, antimicrobial, and cytotoxic properties of Aniba parviflora essential oils from the Amazon, Nat. Prod. Commun., 11, 1025

Matura, 2005, Selected oxidized fragrance terpenes are common contact allergens, Contact Dermat., 52, 320, 10.1111/j.0105-1873.2005.00605.x

Bickers, 2003, A toxicologic and dermatologic assessment of linalool and related esters when used as fragrance ingredients, Food Chem. Toxicol., 41, 919, 10.1016/S0278-6915(03)00016-4

Jenner, 1964, Food flavorings and compounds of related structure. I. acute oral toxicity, Food Cosmet. Toxicol., 2, 327, 10.1016/S0015-6264(64)80192-9

Letizia, 2003, Fragrance material review on linalool, Food Chem. Toxicol., 41, 943, 10.1016/S0278-6915(03)00015-2

Powers, 1985, Toxicolgical aspects of linalool: A review, Vet. Hum. Toxicol., 27, 484

Fujii, 1972, Studies on compounded perfumes for toilet goods. On the non-irritative compounded perfumes for soaps, Yukagaku, 21, 904

Bicas, 2011, Evaluation of the antioxidant and antiproliferative potential of bioflavors, Food Chem. Toxicol., 49, 1610, 10.1016/j.fct.2011.04.012

Placzek, 2007, Evaluation of phototoxic properties of fragrances, Acta Derm. Venereol., 87, 312, 10.2340/00015555-0251

Cruz, 2012, Composition and biological activity of the essential oil from Thapsia minor, a new source of geranyl acetate, Ind. Crop. Prod., 35, 166, 10.1016/j.indcrop.2011.06.030

Kakarla, 2009, Antimicrobial activity of essential oils of four lemongrass (Cymbopogon flexuosus Steud) varieties, Med. Aromat. Plant Sci. Biotechnol., 3, 107

Mortelmans, 1986, Salmonella mutagenicity tests: II. Results from the testing of 270 chemicals, Environ. Mutagen., 8, 1, 10.1002/em.2860080802

Shelby, 1993, Evaluation of a three-exposure mouse bone marrow micronucleus protocol: Results with 49 chemicals, Environ. Mol. Mutagen., 21, 160, 10.1002/em.2850210210

Kim, 2004, Evaluation of antioxidant activity of Australian tea tree (Melaleuca alternifolia) oil and its components, J. Agric. Food Chem., 52, 2849, 10.1021/jf035377d

Li, 2009, Chemical composition and antiproliferative activity of essential oil from the leaves of a medicinal herb, Schefflera heptaphylla, Phytother. Res., 23, 140, 10.1002/ptr.2567

Pirila, 1964, On the chemical nature of the eczematogenic agent in oil of turpentine. IV. the primary irritant effect of terpenes, Dermatologica, 128, 16, 10.1159/000254716

Schlede, 2003, Chemical substances and contact allergy—244 substances ranked according to allergenic potency, Toxicology, 193, 219, 10.1016/S0300-483X(03)00266-X