Biological activities of selected mono- and sesquiterpenes: Possible uses in medicine

Natural Products: Phytochemistry, Botany and Metabolism of Alkaloids, Phenolics and Terpenes

Volumn , Issue , 2013, Pages 4109-4159

  Buchbauer, Gerhard ^a   Ilic, Anja ^a  

^a UNIVERSITY OF VIENNA   (Austria)

Author keywords

(+) limonene; ( ) menthol; 1,8 cineol; Biological activity; Bisabolol; Camphor; Carvacrol; Citral; Farnesol; Linalool; Monoterpenes; Myrcene; Nerolidol; Perillyl alcohol; Pulegone; Sesquiterpenes; Thujone; Thymol; humulene; caryophyllene

Indexed keywords

EID: 84976446656     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1007/978-3-642-22144-6_183     Document Type: Chapter

References (158)

1. Maffei ME (2010) Sites of synthesis, biochemistry and functional role of plant volatiles. J Afr J Bot 76:612-6311
2. Maffei ME, Gertsch J, Appendino G (2011) Plant volatiles: production, function and pharmacology. Nat Prod Rep 28:1359-1380
3. Buchbauer G (2002) Lavender oil and its therapeutic properties. In: Lis-Balchin M (ed) Lavender. The genus Lavandula. Taylor & Francis, London/New York, pp 124-139
4. Buchbauer G (2010) Biological activities of essential oils. In: Baser KHC, Buchbauer G (eds) Handbook of essential oils, science, technology and applications. CRC Press/Taylor 6 Francis, Boca Raton/London/New York, pp 235-280
5. Adorjan B, Buchbauer G (2010) Biological properties of essential oils: an updated review. Flavor Fragr J 25:407-426
6. Dobetsberger C, Buchbauer G (2011) Actions of essential oils on the central nervous system: an updated review. Flavor Fragr J 26:300-316
7. Lang G, Buchbauer G (2012) A review on recent research results (2008-2010) on essential oils as antimicrobials and antifungals. A review. Flavor Fragr J 27:13-39
8. Heuberger E, Nunes DS, de Moura Linck V, da Silva AL, Figueiro M, Elisabetsky E (2010) Effects of essential oils in the central nervous system. In: Baser KHC, Buchbauer G (eds) Handbook of essential oils, science, technology and applications. CRS Press/Taylor & Francis, Boca Raton/London/New York, pp 281-314
9. Harris B (2010) Phytotherapeutic uses of essential oils. In: Baser KHC, Buchbauer G (eds) Handbook of essential oils, science, technology and applications. CRS Press/Taylor & Francis, Boca Raton/London/New York, pp 315-351
10. Muller M, Buchbauer G (2011) Essential oil components as pheromones. A review. Flavour Fragr J 26:357-377
11. Ohloff G (1990) Riechstoffe und Geruchssinn. Die molekulare Welt der Dufte. Springer, Berlin/Heidelberg/New York, p 130
12. Friedman L, Miller JG (1971) Odor incongruity and chirality. Science 172:1044
13. Legrum W (2011) Riechstoffe zwischen Gestank und Duft. Vorkommen, Eigenschaften und Anwendung von Riechstoffen und deren Gemischen, Vieweg + Teubner, Wiesbaden, p 45
14. 2 modulation and cell proliferation. Basic Clin Pharmacol Toxicol 106(1):38-44
15. Singh P, Shukla R, Prakash B, Kumar A, Singh S, Mishra PK, Dubey NK (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(6):1734-1740
16. United States Environmental Protection Agency (1994) Prevention, pesticides and toxic substances (7508 W) EPA-738-F-94-030
17. Chaudhary SC, Siddiqui MS, Athar M, Alam MS (2012) D-Limonene modulates inflammation, oxidative stress and Ras-ERK pathway to inhibit murine skin tumorigenesis. Hum Exp Toxicol. doi:10.1177/0960327111434948
18. Victor Antony Santiago J, Jayachitra J, Shenbagam M, Nalini N (2012) Dietary d-limonene alleviates insulin resistance and oxidative stress-induced liver injury in high-fat diet and L-NAME-treated rats. Eur J Nutr 51(1):57-68
19. Park HM, Lee JH, Yaoyao J, Jun HJ, Lee SJ (2011) Limonene, a natural cyclic terpene, is an agonistic ligand for adenosine A(2A) receptors. Biochem Biophys Res Commun 404(1): 345-348
20. Fletcher WR, Lea Sanford R, Kapoor R, Andersen OS (2011) Limonene, a natural cyclic terpene, is an agonistic ligand for adenosine A(2A) receptors. Biophys J 100(3 Suppl 1):500a
21. Komori T, Fujiwara R, Tanida M, Nomura J (1995) Potential antidepressant effects of lemon odor in rats. J Eur Neuropsychopharmacol 5(4):477-480
22. de Almeida AA, Costa JP, de Carvalho RB, de Sousa DP, de Freitas RM (2012) Evaluation of acute toxicity of a natural compound (+)-limonene epoxide and its anxiolytic-like action. Brain Res 1448:56-62
23. Gertsch J, Leonti M, Raduner S, Racz I, Chen JZ, Xie XQ, Altmann KH, Karsak M, Zimmer A (2008) Beta-caryophyllene is a dietary cannabinoid. Proc Natl Acad Sci USA 105(26):9099-9104
24. Reinsvold RE, Jinkerson RE, Radakovits R, Posewitz MC, Basu C (2011) The production of the sesquiterpene ß-caryophyllene in a transgenic strain of the cyanobacterium Synechocystis. J Plant Physiol 168(8):848-852
25. Sharma GD, He J, Bazan HE (2003) p38 and ERK1/2 coordinate cellular migration and proliferation in epithelial wound healing: evidence of cross-talk activation between MAP kinase cascades. J Biol Chem 278(24):21989-21997
26. Horvath B, Mukhopadhyay P, Kechrid M, Patel V, Tanchian G, Wink DA, Gertsch J, Pacher P (2012) ß-Caryophyllene ameliorates cisplatin-induced nephrotoxicity in a cannabinoid 2 receptor-dependent manner. Free Radic Biol Med 52(8):1325-1333
27. 2receptor activation and PPARg pathway. Am J Pathol 178(3):1153-1166
28. Leonhardt V, Leal-Cardoso JH, Lahlou S, Albuquerque AA, Porto RS, Celedonio NR, Oliveira AC, Pereira RF, Silva LP, Garcia-Teofilo TM, Silva AP, Magalhaes PJ, Duarte GP, Coelho-de-Souza AN (2010) Antispasmodic effects of essential oil of Pterodon polygalaeflorus and its main constituent ß-caryophyllene on rat isolated ileum. Fundam Clin Pharmacol 24(6):749-758
29. Di Sotto A, Evandri MG, Mazzanti G (2008) Antimutagenic and mutagenic activities of some terpenes in the bacterial reverse mutation assay. Mutat Res 653(1-2):130-133
30. Legault J, Pichette A (2007) Potentiating effect of beta-caryophyllene on anticancer activity of alpha-humulene, isocaryophyllene and paclitaxel. J Pharm Pharmacol 59(12): 1643-1647
31. Di Sotto A, Mazzanti G, Carbone F, Hrelia P, Maffei F (2010) Inhibition by beta-caryophyllene of ethyl methanesulfonate-induced clastogenicity in cultured human lymphocytes. Mutat Res 699(1-2):23-28
32. Neuenschwander U, Czarniecki B, Hermans I (2012) Origin of regioselectivity in a-humulene functionalization. J Org Chem 77(6):2865-2869
33. Nissen L, Zatta A, Stefanini I, Grandi S, Sgorbati B, Biavati B, Monti A (2010) Characterization and antimicrobial activity of essential oils of industrial hemp varieties (Cannabis sativa L.). Fitoterapia 81(5):413-419
34. Chaves JS, Leal PC, Pianowisky L, Calixto JB (2008) Pharmacokinetics and tissue distribution of the sesquiterpene alpha-humulene in mice. Planta Med 74(14):1678-1683
35. Fernandes ES, Passos GF, Medeiros R, da Cunha FM, Ferreira J, Campos MM, Pianowski LF, Calixto JB (2007) Anti-inflammatory effects of compounds alpha-humulene and (-)-trans-caryophyllene isolated from the essential oil of Cordia verbenacea. Eur J Pharmacol 569(3):228-236
36. Rogerio AP, Andrade EL, Leite DF, Figueiredo CP, Calixto JB (2009) Preventive and therapeutic anti-inflammatory properties of the sesquiterpene alpha-humulene in experimental airways allergic inflammation. Br J Pharmacol 158(4):1074-1087
37. El Hadri A, Gomez del Rio MA, Sanz J, Coloma AG, Idaomar M, Ozonas BR, Gonzalez JB, Sanchez Reus MI (2010) Actividad citotoxica del a-humuleno y del tras-cariofileno de Salvia officinalis en dos lineas celulares tumorales animal y humana. Anales de la Real Academia Nacional de Farmacia 76(3):343-356
38. Behr A, Johnen L (2009) Myrcene as a natural base chemical in sustainable chemistry: a critical review. ChemSusChem 2(12):1072-1095
39. Chan PC, Cesta MF, Sills RC, Bishop JB, Bristol DW, Bucher JR, Chhabra RS, Foster PM, Herbert RA, Hooth MJ, King-Herbert AP, Kissling GE, Malarkey DE, Roycroft JH, Sanders JM, Smith CS, Travlos GS, Walker NJ, Witt KL (2010) NTP technical report on the toxicology and carcinogenesis studies of beta-myrcene (CAS No. 123-35-3) in F344/N rats and B6C3F1 mice (Gavage studies). Natl Toxicol Program Tech Rep Ser 557:1-163
40. Galeotti N, Di Cesare Mannelli L, Mazzanti G, Bartolini A, Ghelardini C (2002) Menthol: a natural analgesic compound. Neurosci Lett 322(3):145-148
41. Kahnert S, Nair U, Mons U, Potschke-Langer M (2012) Effects of menthol as an additive in tobacco products and the need for regulation. Bundesgesundheitsblatt Gesundheitsforschung Gesundheitsschutz 55(3):409-415
42. Willis DN, Liu B, Ha MA, Jordt SE, Morris JB (2011) Menthol attenuates respiratory irritation responses to multiple cigarette smoke irritants. FASEB J 25(12):4434-4444
43. Abobo CV, Ma J, Liang D (2012) Effect of menthol on nicotine pharmacokinetics in rats after cigarette smoke inhalation. Nicotine Tob Res 14(7):801-808
44. Kreslake JM, Yerger VB (2010) Tobacco industry knowledge of the role of menthol in chemosensory perception of tobacco smoke. Nicotine Tob Res 12(Suppl 2):S98-S101
45. Kim SH, Nam JH, Park EJ, Kim BJ, Kim SJ, So I, Jeon JH (2009) Menthol regulates TRPM8-independent processes in PC-3 prostate cancer cells. Biochim Biophys Acta 1792(1):33-38
46. Bhadania M, Joshi H, Patel P, Kulkarni VH (2012) Protective effect of menthol on ß-amyloid peptide induced cognitive deficits in mice. Eur J Pharmacol 681(1-3):50-54
47. Hiki N, Kaminishi M, Hasunuma T, Nakamura M, Nomura S, Yahagi N, Tajiri H, Suzuki H (2011) A phase I study evaluating tolerability, pharmacokinetics, and preliminary efficacy of L-menthol in upper gastrointestinal endoscopy. Clin Pharmacol Ther 90(2):221-228
48. Topp R, Winchester LJ, Schilero J, Jacks D (2011) Effect of topical menthol on ipsilateral and contralateral superficial blood flow following a bout of maximum voluntary muscle contraction. Int J Sports Phys Ther 6(2):83-91
49. Topp R, Winchester L, Mink AM, Kaufman JS, Jacks DE (2011) Comparison of the effects of ice and 3.5% menthol gel on blood flow and muscle strength of the lower arm. J Sport Rehabil 20(3):355-366
50. Braca A, Siciliano T, D’Arrigo M, Germant, MP (2008) Chemical composition and antimicrobial activity of Momordica charantia seed essential oil. Fitoterapia 79(2):123-125
51. Peres VF, Moura DJ, Sperotto AR, Damasceno FC, Caramao EB, Zini CA, Saffi J (2009) Chemical composition and cytotoxic, mutagenic and genotoxic activities of the essential oil from Pipergaudichaudianum Kunth leaves. Food Chem Toxicol 47(9):2389-2395
52. Marques AM, Barreto AL, Batista EM, Curvelo JA, Velozo LS, Moreira Dde L, Guimaraes EF, Soares RM, Kaplan MA (2010) Chemistry and biological activity of essential oils from Piper claussenianum (Piperaceae). Nat Prod Commun 5(11):1837-1840
53. Lapczynski A, Bhatia SP, Letizia CS, Api AM (2008) Fragrance material review on nerolidol (isomer unspecified). Food Chem Toxicol 46(Suppl 11):S247-S250
54. Williams AC, Barry BW (2004) Penetration enhancers. Adv Drug Deliv Rev 56(5):603-618
55. Cornwell PA, Barry BW, Bouwstrab JA, Gooris GS (1996) Modes of action of terpene penetration enhancers in human skin differential scanning calorimetry, small-angle X-ray diffraction and enhancer uptake studies. Int J Pharm 127(1):9-26
56. Wattenberg LW (1991) Inhibition of azoxymethane-induced neoplasia of the large bowel by 3-hydroxy-3,7,11-trimethyl-1,6,10-dodecatriene (nerolidol). Carcinogenesis 12(1): 151-152
57. Inoue Y, Shiraishi A, Hada T, Hirose K, Hamashima H, Shimada J (2004) The antibacterial effects of terpene alcohols on Staphylococcus aureus and their mode of action. FEMS Microbiol Lett 237(2):325-331
58. Lee SJ, Han JI, Lee GS, Park MJ, Choi IG, Na KJ, Jeung EB (2007) Antifungal effect of eugenol and nerolidol against Microsporum gypseum in a guinea pig model. Biol Pharm Bull 30(1):184-188
59. Arruda DC, D’Alexandri FL, Katzin AM, Uliana SR (2005) Antileishmanial activity of the terpene nerolidol. Antimicrob Agents Chemother 49(5):1679-1687
60. Klopell FC, Lemos M, Sousa JP, Comunello E, Maistro EL, Bastos JK, de Andrade SF (2007) Nerolidol, an antiulcer constituent from the essential oil of Baccharis dracunculifolia DC (Asteraceae). Z Naturforsch C 62(7-8):537-542
61. Hollis J (2009) Biopesticides registration action document. Farnesol Nerolidol
62. Ferreira FM, Palmeira CM, Oliveira MM, Santos D, Simoes AM, Rocha SM, Coimbra MA, Peixoto F (2012) Nerolidol effects on mitochondrial and cellular energetics. Toxicol In Vitro 26(2):189-196
63. Piculo F, Guiraldeli Macedo C, de Andrade SF, Luis Maistro E (2011) In vivo genotoxicity assessment of nerolidol. J Appl Toxicol 31(7):633-639
64. Pammi M, Liang R, Hicks JM, Barrish J, Versalovic J (2011) Famesol decreases biofilms of Staphylococcus epidermidis and exhibits synergy with nafcillin and vancomycin. Pediatr Res 70(6):578-583
65. Decanis N, Tazi N, Correia A, Vilanova M, Rouabhia M (2011) Farnesol, a fungal quorumsensing molecule triggers Candida albicans morphological changes by downregulating the expression of different secreted aspartyl proteinase genes. Open Microbiol J 5:119-126
66. Meigs TE, Simoni RD (1997) Farnesol as a regulator of HMG-CoA reductase degradation: characterization and role of farnesyl pyrophosphatase. Arch Biochem Biophys 345(1):1-9
67. Joo JH, Jetten AM (2010) Molecular mechanisms involved in farnesol-induced apoptosis. Cancer Lett 287(2):123-135
68. Qamar W, Khan AQ, Khan R, Lateef A, Tahir M, Rehman MU, Ali F, Sultana S (2012) Benzo(a)pyrene-induced pulmonary inflammation, edema, surfactant dysfunction, and injuries in rats: alleviation by farnesol. Exp Lung Res 38(1):19-27
69. Khan R, Sultana S (2011) Farnesol attenuates 1,2-dimethylhydrazine induced oxidative stress, inflammation and apoptotic responses in the colon of Wistar rats. Chem Biol Interact 192(3)
70. de Oliveira Junior WM, Benedito RB, Pereira WB, de Arruda Torres P, Ramos CA, Costa JP, da Rocha Tome A, de Sousa DP, de Freitas RM, De Fatima Formiga Melo Diniz M, De Almeida RN (2012) Farnesol: antinociceptive effect and histopathological analysis of the striatum and hippocampus of mice. Fundam Clin Pharmacol. doi:10.1111/j.1472-8206.2012.01030.x
71. Duncan RE, Archer MC (2008) Farnesol decreases serum triglycerides in rats: identification of mechanisms including up-regulation of PPARalpha and down-regulation of fatty acid synthase in hepatocytes. Lipids 43(7):619-627
72. Goto T, Kim YI, Funakoshi K, Teraminami A, Uemura T, Hirai S, Lee JY, Makishima M, Nakata R, Inoue H, Senju H, Matsunaga M, Horio F, Takahashi N, Kawada T (2011) Am J Farnesol, an isoprenoid, improves metabolic abnormalities in mice via both PPARa-dependent and-independent pathways. Physiol Endocrinol Metab 301(5):E1022-E1032
73. Cavanagh HMA, Wilkinson JM (2002) Biological activities of lavender essential oil. Phytother Res 16:301-308
74. Linck VM, da Silva AL, Figueiro M, Caramao EB, Moreno PR, Elisabetsky E (2010) Effects of inhaled Linalool in anxiety, social interaction and aggressive behavior in mice. Phytomedicine 17(8-9):679-683
75. Takahashi M, Satou T, Ohashi M, Hayashi S, Sadamoto K, Koike K (2011) Interspecies comparison of chemical composition and anxiolytic-like effects of lavender oils upon inhalation. Nat Prod Commun 6(11):1769-1774
76. Coelho VR, Gianesini J, Von Borowski R, Mazzardo-Martins L, Martins DF, Picada JN, Santos AR, Brum LF, Pereira P (2011) (-)-Linalool, a naturally occurring monoterpene compound, impairs memory acquisition in the object recognition task, inhibitory avoidance test and habituation to a novel environment in rats. Phytomedicine 18(10):896-901
77. Sampaio Lde F, Maia JG, de Parijos AM, de Souza RZ, Barata LE (2012) Linalool from rosewood (Aniba rosaeodora Ducke) oil inhibits adenylate cyclase in the retina, contributing to understanding its biological activity. Phytother Res 26(1):73-77
78. de Sousa DP, Nobrega FF, Santos CC, de Almeida RN (2010) Anticonvulsant activity of the linalool enantiomers and racemate: investigation of chiral influence. Nat Prod Commun 5(12):1847-1851
79. Cho SY, Jun HJ, Lee JH, Jia Y, Kim KH, Lee SJ (2011) Linalool reduces the expression of 3-hydroxy-3-methylglutaryl CoA reductase via sterol regulatory element binding protein-2-and ubiquitin-dependent mechanisms. FEBS Lett 585(20):3289-3296
80. Gu Y, Ting Z, Qiu X, Zhang X, Gan X, Fang Y, Xu X, Xu R (2010) Linalool preferentially induces robust apoptosis of a variety of leukemia cells via upregulating p53 and cyclin-dependent kinase inhibitors. Toxicology 268(1-2):19-24
81. Rocha NF, Rios ER, Carvalho AM, Cerqueira GS, Lopes Ade A, Leal LK, Dias ML, de Sousa DP, de Sousa FC (2011) Anti-nociceptive and anti-inflammatory activities of (-)-a-bisabolol in rodents. Naunyn Schmiedebergs Arch Pharmacol 384(6): 525-533
82. Seki T, Kokuryo T, Yokoyama Y, Suzuki H, Itatsu K, Nakagawa A, Mizutani T, Miyake T, Uno M, Yamauchi K, Nagino M (2011) Antitumor effects of a-bisabolol against pancreatic cancer. Cancer Sci 102(12):2199-2205. doi:10.1111/j.1349-7006.2011.02082
83. Moura Rocha NF, Venüncio ET, Moura BA, Gomes Silva MI, Aquino Neto MR, Vasconcelos Rios ER, de Sousa DP, Mendes Vasconcelos SM, de Franca Fonteles MM, de Sousa FC (2010) Gastroprotection of (-)-alpha-bisabolol on acute gastric mucosal lesions in mice: The possible involved pharmacological mechanisms. Fundam Clin Pharmacol 24(1):63-71
84. Rocha NF, Oliveira GV, Araujo FY, Rios ER, Carvalho AM, Vasconcelos LF, Macüdo DS, Soares PM, Sousa DP, Sousa FC (2011) (-)-a-Bisabolol-induced gastroprotection is associated with reduction in lipid peroxidation, superoxide dismutase activity and neutrophil migration. Eur J Pharm Sci 44(4):455-461
85. Cavalieri E, Rigo A, Bonifacio M, Carcereri de Prati A, Guardalben E, Bergamini C, Fato R, Pizzolo G, Suzuki H, Vinante F (2011) Pro-apoptotic activity of a-bisabolol in preclinical models of primary human acute leukemia cells. J Transl Med 21:9-45
86. De Siqueira RJ, Freire WB, Vasconcelos-Silva AA, Fonseca-Magalhües PA, Lima FJ, Brito TS, Mourao LT, Ribeiro RA, Lahlou S, Magalhaes PJ (2012) In-vitro characterization of the pharmacological effects induced by (-)-a-bisabolol in rat smooth muscle preparations. Can J Physiol Pharmacol 90(1):23-35
87. Alves Ade M, Goncalves JC, Cruz JS, Araujo DA (2010) Evaluation of the sesquiterpene (-)-alpha-bisabolol as a novel peripheral nervous blocker. Neurosci Lett 472(1):11-15
88. Jayakumar S, Madankumar A, Asokkumar S, Raghunandhakumar S, Gokula Dhas K, Kamaraj S, Divya MG, Devaki T (2012) Potential preventive effect of carvacrol against diethylnitrosamine-induced hepatocellular carcinoma in rats. Mol Cell Biochem 360(1-2):51-60
89. Austgulen LT, Solheim E, Scheline RR (1987) Metabolism in rats of p-cymene derivatives: carvacrol and thymol. Pharmacol Toxicol 61(2):98-102
90. Xu H, Delling M, Jun JC, Clapham DE (2006) Oregano, thyme and clove-derived flavors and skin sensitizers activate specific TRP channels. Nat Neurosci 9(5):628-635
91. Parnas M, Peters M, Dadon D, Lev S, Vertkin I, Slutsky I, Minke B (2009) Carvacrol is a novel inhibitor of Drosophila TRPL and mammalian TRPM7 channels. Cell Calcium 45(3):300-309
92. Hotta M, Nakata R, Katsukawa M, Hori K, Takahashi S, Inoue H (2010) Carvacrol, a component of thyme oil, activates PPARalpha and gamma and suppresses COX-2 expression. J Lipid Res 51(1):132-139
93. Liu Y, Song M, Che TM, Bravo D, Pettigrew JE (2012) Anti-inflammatory effects of several plant extracts on porcine alveolar macrophages in vitro. J Anim Sci. doi:10.2527/jas.2011-4304
94. Guimaraes AG, Xavier MA, de Santana MT, Camargo EA, Santos CA, Brito FA, Barreto EO, Cavalcanti SC, Antoniolli AR, Oliveira RC, Quintans-Jilnior LJ (2012) Carva-crol attenuates mechanical hypernociception and inflammatory response. Naunyn Schmiedebergs Arch Pharmacol 385(3):253-263
95. Boskabady MH, Tabanfar H, Gholamnezhad Z, Sadeghnia HR (2011) Inhibitory effect of Zataria multiflora Boiss and carvacrol on histamine (H(1)) receptors of guinea-pig tracheal chains. Fundam Clin Pharmacol. doi:10.1111/j.1472-8206.2011.00971.x
96. Aristatile B, Al-Numair KS, Al-Assaf AH, Pugalendi KV (2011) Pharmacological effect of carvacrol on D:-galactosamine-induced mitochondrial enzymes and DNA damage by single-cell gel electrophoresis. J Nat Med 65(3-4):568-577
97. Yin QH, Yan FX, Zu XY, Wu YH, Wu XP, Liao MC, Deng SW, Yin LL, Zhuang YZ (2012) Anti-proliferative and pro-apoptotic effect of carvacrol on human hepatocellular carcinoma cell line HepG-2. Cytotechnology 64(1):43-51
98. Dong RH, Fang ZZ, Zhu LL, Liang SC, Ge GB, Yang L, Liu ZY (2012) Investigation of UDP-glucuronosyltransferases (UGTs) inhibitory properties of carvacrol. Phytother Res 26(1):86-90. doi:10.1002/ptr.3525
99. Yu H, Zhang ZL, Chen J, Pei A, Hua F, Qian X, He J, Liu CF, Xu X (2012) Carvacrol, a food-additive, provides neuroprotection on focal cerebral ischemia/reperfusion injury in mice. PLoS One 7(3):e33584
100. Azizi Z, Ebrahimi S, Saadatfar E, Kamalinejad M, Majlessi N (2012) Cognitive-enhancing activity of thymol and carvacrol in two rat models of dementia. Behav Pharmacol 23(3):241-249
101. Nostro A, Papalia T (2012) Antimicrobial activity of carvacrol: current progress and future prospectives. Recent Pat Antiinfect Drug Discov 7(1):28-35
102. Inamuco J, Veenendaal AK, Burt SA, Post JA, Tjeerdsma-van Bokhoven JL, Haagsman HP, Veldhuizen EJ (2011) Sub-lethal levels of carvacrol reduce Salmonella Typhimurium motility and invasion of porcine epithelial cells. Vet Microbiol 157(1-2):200-207
103. Archana PR, Nageshwar Rao B, Satish Rao BS (2011) Modulation of gamma ray-induced genotoxic effect by thymol, a monoterpene phenol derivative of cymene. Integr Cancer Ther 10(4):374-383
104. Satooka H, Kubo I (2012) Effects of thymol on b16-f10 melanoma cells. J Agric Food Chem 60(10):2746-2752
105. Kaji I, Karaki S, Kuwahara A (2011) Effects of luminal thymol on epithelial transport in human and rat colon. Am J Physiol Gastrointest Liver Physiol 300(6):G1132-G1143
106. Engelbertz J, Lechtenberg M, Studt L, Hensel A, Verspohl EJ (2012) Bioassay-guided fractionation of a thymol-deprived hydrophilic thyme extract and its antispasmodic effect. J Ethnopharmacol 141(3):848-853
107. Xuan NT, Shumilina E, Schmid E, Bhavsar SK, Rexhepaj R, Gotz F, Gulbins E, Lang F (2010) Role of acidic sphingomyelinase in thymol-mediated dendritic cell death. Mol Nutr Food Res 54(12):1833-1841
108. 2+ homeostasis and viability in human glioblastoma cells. Eur J Pharmacol 670(1):85-91
109. 2+ homeostasis and viability in MG63 human osteosarcoma cells. Pharmacology 88(3-4):201-212
110. Satooka H, Kubo I (2011) Effects of thymol on mushroom tyrosinase-catalyzed melanin formation. J Agric Food Chem 59(16):8908-8914
111. Deb DD, Parimala G, Saravana Devi S, Chakraborty T (2011) Effect of thymol on peripheral blood mononuclear cell PBMC and acute promyelotic cancer cell line HL-60. Chem Biol Interact 193(1):97-106
112. Archana PR, Nageshwar Rao B, Satish Rao BS (2011) In vivo radioprotective potential of thymol, a monoterpene phenol derivative of cymene. Mutat Res 726(2):136-145
113. Garcia DG, Amorim LM, de Castro Faria MV, Freire AS, Santelli RE, Da Fonseca CO, Quirico-Santos T, Burth P (2010) The anticancer drug perillyl alcohol is a Na/K-ATPase inhibitor. Mol Cell Biochem 345(1-2):29-34
114. da Fonseca CO, Simao M, Lins IR, Caetano RO, Futuro D, Quirico-Santos T (2011) Efficacy of monoterpene perillyl alcohol upon survival rate of patients with recurrent glioblastoma. J Cancer Res Clin Oncol 137(2):287-293
115. da Fonseca CO, Schwartsmann G, Fischer J, Nagel J, Futuro D, Quirico-Santos T, Gattass CR (2008) Preliminary results from a phase I/II study of perillyl alcohol intranasal administration in adults with recurrent malignant gliomas. Surg Neurol 70(3):259-266, Discussion 266-7
116. De Saldanha Da Gama Fischer J, Costa Carvalho P, da Fonseca CO, Liao L, Degrave WM, Da Gloria Da Costa Carvalho M, Yates JR, Domont GB (2011) Chemo-resistant protein expression pattern of glioblastoma cells (A172) to perillyl alcohol. J Proteome Res 10(1): 153-160
117. da Silveira FD, Lopes BD, da Fonseca CO, Quirico-Santos T, de Palmer Paixao IC, de Amorim LM (2012) Analysis of EGF + 61A > G polymorphism and EGF serum levels in Brazilian glioma patients treated with perillyl alcohol-based therapy. J Cancer Res Clin Oncol. doi:10.1007/s00432-012-1203-5
118. Khan AQ, Nafees S, Sultana S (2011) Perillyl alcohol protects against ethanol induced acute liver injury in Wistar rats by inhibiting oxidative stress, NFk-B activation and proinflammatory cytokine production. Toxicology 279(1-3):108-114
119. Kirsch F, Beauchamp J, Buettner A (2012) Time-dependent aroma changes in breast milk after oral intake of a pharmacological preparation containing 1,8-cineole. Clin Nutr
120. Datenblatt Merck’s 1,8-cineole data sheet, called up 3.5.2012
121. Juergens UR, Dethlefsen U, Steinkamp G, Gillissen A, Repges R, Vetter H (2003) Antiinflammatory activity of 1.8-cineol (eucalyptol) in bronchial asthma: a double-blind placebocontrolled trial. Respir Med 97(3):250-256
122. Juergens UR, Engelen T, Racke K, Stober M, Gillissen A, Vetter H (2004) Inhibitory activity of 1,8-cineol (eucalyptol) on cytokine production in cultured human lymphocytes and monocytes. Pulm Pharmacol Ther 17(5):281-287
123. Worth H, Schacher C, Dethlefsen U (2009) Concomitant therapy with Cineole (Eucalyptole) reduces exacerbations in COPD: a placebo-controlled double-blind trial. Respir Res 10:69
124. Rahimi-Nasrabadi M, Ahmadi F, Batooli H (2012) Chemical composition of essential oil and in vitro antioxidant activities of the essential oil and methanol extracts of Eucalyptus loxophleba. Nat Prod Res 26(7):669-674
125. Culic M, Kekovic G, Grbic G, Martac L, Sokovic M, Podgorac J, Sekulic S (2009) Wavelet and fractal analysis of rat brain activity in seizures evoked by camphor essential oil and 1.8-cineole. Gen Physiol Biophys 28:33-40
126. Yoshimura H, Sawai Y, Tamotsu S, Sakai A (2011) 1,8-cineole inhibits both proliferation and elongation of BY-2 cultured tobacco cells. J Chem Ecol 37(3):320-328
127. Tomsheck AR, Strobel GA, Booth E, Geary B, Spakowicz D, Knighton B, Floerchinger C, Sears J, Liarzi O, Ezra D (2010) Hypoxylon sp., an endophyte of Persea indica, producing 1.8-cineole and other bioactive volatiles with fuel potential. Microb Ecol 60(4):903-914
128. Alkhateeb H, Bonen A (2010) Thujone, a component of medicinal herbs, rescues palmitate-induced insulin resistance in skeletal muscle. Am J Physiol Regul Integr Comp Physiol 299(3):R804-R812
129. Lachenmeier DW, Uebelacker M (2010) Risk assessment of thujone in foods and medicines containing sage and wormwood-evidence for a need of regulatory changes? Regul Toxicol Pharmacol 3:437-443
130. Raal A, Orav A, Arak E (2007) Composition of the essential oil of Salvia officinalis L. from various European countries. Nat Prod Res 21(5):406-411
131. National Toxicology Program (2011) Toxicology and carcinogenesis studies of alpha, beta-thujone (CAS No. 76231-76-0) in F344/N rats and B6C3F1 mice (gavage studies). Natl Toxicol Program Tech Rep Ser 570:1-260
132. Abass K, Reponen P, Mattila S, Pelkonen O (2011) Metabolism of a-thujone in human hepatic preparations in vitro. Xenobiotica 41(2):101-111
133. Szczot M, Czyzewska MM, Appendino G, Mozrzymas JW (2012) Modulation of GABAergic synaptic currents and current responses by a-thujone and dihydroumbellulone. J Nat Prod 75(4):622-629
134. Biswas R, Mandal SK, Dutta S, Bhattacharyya SS, Boujedaini N, Khuda-Bukhsh AR (2011) Thujone-rich fraction of Thuja occidentalis demonstrates major anti-cancer potentials: evidences from in vitro studies on A375 cells. Evid Based Complement Altern Med 2011:568148
135. Siveen KS, Kuttan G (2011) Thujone inhibits lung metastasis induced by B16F-10 melanoma cells in C57BL/6 mice. Can J Physiol Pharmacol 89(10):691-703
136. Laciar A, Ruiz ML, Flores RC, Saad JR (2009) Antibacterial and antioxidant activities of the essential oil of Artemisia echegarayi Hieron. (Asteraceae). Rev Argent Microbiol 41(4):226-231
137. Jankelowitz S, Mohamed A, Burke D (2009) Axonal effects of camphor poisoning. J Clin Neurosci 16(12):1639-1641
138. Kumar M, Ando Y (2007) Carbon nanotubes from camphor: an environment-friendly nanotechnology. J Phys Conf Ser 61:643. doi:10.1088/1742-6596/61/1/129
139. Pearce JM (2008) Leopold Auenbrugger: camphor-induced epilepsy-remedy for manic psychosis. Eur Neurol 59(1-2):105-107
140. Peters AL, Dekker E, Michels WM (2011) Camphor poisoning following ingestion of mothballs ‘for headache’. Ned Tijdschr Geneeskd 155(42):A3676
141. Moqrich A, Hwang SW, Earley TJ, Petrus MJ, Murray AN, Spencer KS, Andahazy M, Story GM, Patapoutian A (2005) Impaired thermosensation in mice lacking TRPV3, a heat and camphor sensor in the skin. Science 307(5714):1468-1472
142. Marsakova L, Touska F, Krusek J, Vlachova V (2012) Pore helix domain is critical to camphor sensitivity of transient receptor potential vanilloid 1 channel. Anesthesiology 116(4):903-917
143. Nikolic B, Mitic-Culafic D, Vukovic-Gacic B, KneZevic-Vukcevic J (2011) Modulation of genotoxicity and DNA repair by plant monoterpenes camphor, eucalyptol and thujone in Escherichia coli and mammalian cells. J Food Chem Toxicol 49(9):2035-2045
144. Modak T, Mukhopadhaya A (2011) Effects of citral, a naturally occurring antiadipogenic molecule, on an energy-intense diet model of obesity. Indian J Pharmacol 43(3):300-305
145. Devi RC, Sim SM, Ismail R (2011) Spasmolytic effect of citral and extracts of Cymbopogon citratus on isolated rabbit ileum. J Smooth Muscle Res 47(5):143-156
146. Katsukawa M, Nakata R, Takizawa Y, Hori K, Takahashi S, Inoue H (2010) Citral, a component of lemongrass oil, activates PPARa and g and suppresses COX-2 expression. Biochim Biophys Acta 1801(11):1214-1220
147. Bachiega TF, Sforcin JM (2011) Lemongrass and citral effect on cytokines production by murine macrophages. J Ethnopharmacol 137(1):909-913
148. Ortiz MI, Gonzalez-Garcia MP, Ponce-Monter HA, Castaüeda-Hernandez G, Aguilar-Robles P (2010) Synergistic effect of the interaction between naproxen and citral on inflammation in rats. Phytomedicine 18(1):74-79
149. Chaimovitsh D, Rogovoy Stelmakh O, Altshuler O, Belausov E, Abu-Abied M, Rubin B, Sadot E, Dudai N (2012) The relative effect of citral on mitotic microtubules in wheat roots and BY2 cells. Plant Biol (Stuttg) 14(2):354-364
150. Echeverrigaray S, Michelim L, Longaray Delamare AP, Andrade CP, Pinto da Costa SO, Zacaria J (2008) The effect of monoterpenes on swarming differentiation and haemolysin activity in Proteus mirabilis. Molecules 13(12):3107-3116
151. Aiemsaard J, Aiumlamai S, Aromdee C, Taweechaisupapong S, Khunkitti W (2011) The effect of lemongrass oil and its major components on clinical isolate mastitis pathogens and their mechanisms of action on Staphylococcus aureus DMST 4745. Res Vet Sci 91(3): e31-e37
152. Somolinos M, Garcia D, Condon S, Mackey B, Pagan R (2010) Inactivation of Escherichia coli by citral. J Appl Microbiol 108(6):1928-1939
153. Machado M, Pires P, Dinis AM, Santos-Rosa M, Alves V, Salgueiro L, Cavaleiro C, Sousa MC (2012) Monoterpenic aldehydes as potential anti-leishmania agents: activity of Cymbopogon citratus and citral on L. infantum, L. Tropica and L. major. Exp Parasitol 130(3):223-231
154. Da Rocha MS, Dodmane PR, Arnold LL, Pennington KL, Anwar MM, Adams BR, Taylor SV, Wermes C, Adams TB, Cohen SM (2012) Mode of action of pulegone on the urinary bladder of F344 rats. Toxicol Sci. doi:10.1093/toxsci/kfs135
155. National Toxicology Program (2011) Toxicology and carcinogenesis studies of pulegone (CAS No. 89-82-7) in F344/N rats and B6C3F1 mice (gavage studies). Natl Toxicol Program Tech Rep Ser 563:1-201
156. de Sousa DP, Nobrega FF, de Lima MR, de Almeida RN (2011) Pharmacological activity of (R)-(+)-pulegone, a chemical constituent of essential oils. Z Naturforsch C 66(7-8):353-359
157. 2+ homeostasis and causes negative inotropism in mammalian myocardium. Eur J Pharmacol 672(1-3):135-142
158. Umezu T (2010) Evidence for dopamine involvement in ambulation promoted by pulegone in mice. Pharmacol Biochem Behav 94(4):497-502