Investigation of the anti-melanogenic and antioxidant characteristics of Eucalyptus camaldulensis flower essential oil and determination of its chemical composition

International Journal of Molecular Sciences

Volumn 16, Issue 5, 2015, Pages 10470-10490

  Huang, Huey Chun ^a   Ho, Ya Chi ^b   Lim, Jia Min ^b   Chang, Tzu Yun ^b   Ho, Chen Lung ^c   Chang, Tsong Min ^b  

^a CHINA MEDICAL UNIVERSITY   (Taiwan)

^b HUNGKUANG UNIVERSITY   (Taiwan)

^c TAIWAN FORESTRY RESEARCH INSTITUTE   (Taiwan)

Author keywords

Eucalyptus camaldulensis; Melanin; Melanogenesis; ROS; Tyrosinase

Indexed keywords

ALPHA MUUROLENE; ALPHA PHELLANDRENE; ALPHA THUJENE; AROMADENDRENE; BETA ELEMENE; BETA PINENE; BORNEOL; CALAMENENE; CINEOLE; CYCLIC AMP DEPENDENT PROTEIN KINASE; DELTA CADINENE; ESSENTIAL OIL; EUCALYPTUS CAMALDULENSIS FLOWER OIL; GAMMA CADINENE; HUMULENE; JASMONE; LINALOOL; MITOGEN ACTIVATED PROTEIN KINASE; MYRCENE; OCIMENE; PARA CYMENE; PINENE; REACTIVE OXYGEN METABOLITE; SESQUITERPENE; TERPENE; TERPINENE; TERPINEOL; TERPINOLENE; UNCLASSIFIED DRUG; UNINDEXED DRUG; VIRIDIFLORENE; ANTINEOPLASTIC AGENT; ANTIOXIDANT; PLANT EXTRACT;

ANIMAL CELL; ANTIMELANOGENIC ACTIVITY; ANTIOXIDANT ACTIVITY; ARTICLE; CONTROLLED STUDY; DEPIGMENTATION; DRUG ACTIVITY; ENZYME ACTIVITY; EUCALYPTUS CAMALDULENSIS; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; MELANOGENESIS; NONHUMAN; SKIN CARE; WESTERN BLOTTING; ANIMAL; CHEMISTRY; DRUG EFFECTS; EUCALYPTUS; FLOWER; MELANOMA; METABOLISM; MOUSE; SIGNAL TRANSDUCTION; TUMOR CELL LINE;

BASIDIOMYCOTA; EUCALYPTUS CAMALDULENSIS;

ANIMALS; ANTINEOPLASTIC AGENTS; ANTIOXIDANTS; CELL LINE, TUMOR; EUCALYPTUS; FLOWERS; MAP KINASE SIGNALING SYSTEM; MELANOMA; MICE; OILS, VOLATILE; PLANT EXTRACTS; TERPENES;

EID: 84929340104     PISSN: 16616596     EISSN: 14220067     Source Type: Journal    
DOI: 10.3390/ijms160510470     Document Type: Article

References (62)

1. Panich, U.; Tangsupa-A-Nan, V.; Onkoksoong, T.; Kongtaphan, K.; Kasetsinsombat, K.; Akarasereenont, P.; Wongkajornsilp, A. Inhibition of UVA-mediated melanogenesis by ascorbic acid through modulation of antioxidant defense and nitric oxide system. Arch. Pharm. Res. 2011, 34, 811–820.
2. Slominski, A.; Zmijewski, M.A.; Pawelek, J. L-Tyrosine and L-dihydroxyphenylalanine as hormone-like regulators of melanocyte functions. Pigment Cell Melanoma Res. 2012, 25, 14–27.
3. Briganti, S.; Camera, E.; Picardo, M. Chemical and instrumental approaches to treat hyperpigmentation. Pigment Cell Res. 2003, 16, 101–110.
4. Garcia, A.; Fulton, J.E., Jr. The combination of glycolic acid and hydroquinone or kojic acid for the treatment of melasma and related conditions. Dermatol. Surg. 1996, 22, 443–447.
5. Virador, V.M.; Kobayashi, N.; Matsunaga, J.; Hearing, V.J. A standardized protocol for assessing regulators of pigmentation. Anal. Biochem. 1999, 270, 207–219.
6. Sarkar, R.; Bhalla, M.; Kanwar, A.J. A comparative study of 20% azelaic acid cream monotherapy vs. a sequential therapy in the treatment of melasma in dark-skinned patients. Dermatology. 2002, 205, 249–254.
7. Rendon, M.I.; Gaviria, J.I. Review of skin-lightening agents. Dermatol. Surg. 2005, 31, 886–889.
8. García-Gavín, J.; González-Vilas, D.; Fernández-Redondo, V.; Toribio, J. Pigmented contact dermatitis due to kojic acid. A paradoxical side effect of a skin lightener. Contact Dermat. 2010, 62, 63–64.
9. Cheng, S.L.; Liu, R.H.; Sheu, J.N.; Chen, S.T.; Sinchaikul, S.; Tsay, G.J. Toxicogenomics of A375 human malignant melanoma cells treated with arbutin. J. Biomed. Sci. 2007, 14, 87–105.
10. Balina, L.M.; Graupe, K. The treatment of melasma: 20% Azelaic acid vs. 4% hydroquinone cream. Int. J. Dermatol. 1991, 30, 893–895.
11. Halliwell, B. Free radicals, antioxidants, and human disease: Curiosity, cause, or consequence? Lancet 1994, 344, 721–724.
12. Finkel, T.; Holbrook, N.J. Oxidants, oxidative stress and the biology of ageing. Nature 2000, 408, 239–247.
13. Wlaschek, M.; Briviba, K.; Stricklin, G.P.; Sies, H.; Scharffetter-Kochanek, K. Singlet oxygen may mediate the ultraviolet A-induced synthesis of interstitial collagenase. J. Investig. Dermatol. 1995, 104, 194–198.
14. Sárdy, M. Role of matrix metalloproteinases in skin ageing. Connect. Tissue Res. 2009, 50, 132–138.
15. Büyükokuroǧlu, M.E.; Gülçin, I.; Oktay, M.; Küfrevioǧlu, Ö.I. In vitro antioxidant properties of dantrolene sodium. Pharmacol. Res. 2001, 44, 491–494.
16. Shahidul Alam, M.; Quader, M.A.; Rashid, M.A. HIV-inhibitory diterpenoid from Anisomeles indica. Fitoterapia 2000, 71, 574–576.
17. Gülçin, I.; Oktay, M.; Küfrevioǧlu, Ö.I.; Aslan, A. Determination of antioxidant activity of lichen Cetraria islandica (L) Ach. J. Ethnopharmacol. 2002, 79, 325–329.
18. Guo, C.H.; Liu, P.J.; Lin, K.P.; Chen, P.C. Nutritional supplement therapy improves oxidative stress, immune response, pulmonary function, and quality of life in allergic asthma patients: An open-label pilot study. Altern. Med. Rev. 2012, 17, 42–56.
19. Dinis, T.C.P.; Madeira, V.M.C.; Almeida, L.M. Action of phenolic derivatives (acetaminophen, salicylate, and 5-aminosalicylate) as inhibitors of membrane lipid peroxidation and as peroxyl radical scavengers. Arch. Biochem. Biophys. 1994, 315, 161–169.
20. Roméro-Graillet, C.; Aberdam, E.; Clément, M.; Ortonne, J.P.; Ballotti, R. Nitric oxide produced by ultraviolet-irradiated keratinocytes stimulates melanogenesis. J. Clin. Investig. 1997, 99, 635–642.
21. Sasaki, M.; Horikoshi, T.; Uchiwa, H.; Miyachi, Y. Up-regulation of tyrosinase gene by nitric oxide human melanocytes. Pigment Cell Res. 2000, 13, 248–252.
22. Chakraborty, A.K.; Funasaka, Y.; Slominski, A.; Ermak, G.; Hwang, J.; Pawelek, J.M.; Ichihashi, M. Production and release of proopiomelanocortin (POMC) derived peptides by human melanocytes and keratinocytes in culture: Regulation by ultraviolet B. Biochim. Biophys. Acta-Mol. Cell Res. 1996, 1313, 130–138.
23. Yasui, H.; Sakurai, H. Age-dependent generation of reactive oxygen species in the skin of live hairless rats exposed to UVA light. Exp. Dermatol. 2003, 12, 655–661.
24. Funasaka, Y.; Komoto, M.; Ichihashi, M. Depigmenting effect of α-tocopheryl ferulate on normal human melanocytes. Pigment Cell Res. 2000, 13, 170–174.
25. Ormancey, X.; Sisalli, S.; Coutiere, P. Formulation of essential oils in functional perfumery. Parfums Cosmet. Actual. 2001,157, 30–40.
26. Huang, H.C.; Wang, H.F.; Yih, K.H.; Chang, L.Z.; Chang, T.M. Dual bioactivities of essential oil extracted from the leaves of Artemisia argyi as an antimelanogenic vs. antioxidant agent and chemical composition analysis by GC/MS. Int. J. Mol. Sci. 2012, 13, 14679–14697.
27. Huang, H.C.; Chang, T.Y.; Chang, L.Z.; Wang, H.F.; Yih, K.H.; Hsieh, W.Y.; Chang, T.M. Inhibition of melanogenesis versus antioxidant properties of essential oil extracted from leaves of vitex negundo linn and chemical composition analysis by GC-MS. Molecules 2012, 17, 3902–3916.
28. Huang, H.C.; Wang, H.F.; Yih, K.H.; Chang, L.Z.; Chang, T.M. The dual antimelanogenic and antioxidant activities of the essential oil extracted from the leaves of Acorus macrospadiceus (Yamamoto) F. N. Wei et Y. K. Li. Evid.-Based Complement. Altern. Med. 2012, 2012, 781280.
29. Woolf, A. Essential oil poisoning. J. Toxicol.-Clin. Toxicol. 1999, 37, 721–727.
30. Thomson, K.F.; Wilkinson, S.M. Allergic contact dermatitis to plant extracts in patients with cosmetic dermatitis. Br. J. Dermatol. 2000, 142, 84–88.
31. Ghisalberti, E.L. Bioactive acylphloroglucinol derivatives from Eucalyptus species. Phytochemistry 1996, 41, 7–22.
32. Leung, A.Y.; Foster, S. Encyclopedia of Common Natural Ingredients Used in Food, Drugs, and Cosmetics, 2nd ed.; John Willey & Sons: New York, NY, USA, 1996.
33. Cimanga, K.; Kambu, K.; Tona, L.; Apers, S.; de Bruyne, T.; Hermans, N.; Totté, J.; Pieters, L.; Vlietinck, A.J. Correlation between chemical composition and antibacterial activity of essential oils of some aromatic medicinal plants growing in the Democratic Republic of Congo. J. Ethnopharmacol. 2002, 79, 213–220.
34. Silva, J.; Abebe, W.; Sousa, S.M.; Duarte, V.G.; Machado, M.I.L.; Matos, F.J.A. Analgesic and anti-inflammatory effects of essential oils of Eucalyptus. J. Ethnopharmacol. 2003, 89, 277–283.
35. Siramon, P.; Ohtani, Y.; Ichiura, H. Biological performance of Eucalyptus camaldulensis leaf oils from Thailand against the subterranean termite Coptotermes formosanus Shiraki. J. Wood Sci. 2009, 55, 41–46.
36. Cheng, S.S.; Huang, C.G.; Chen, Y.J.; Yu, J.J.; Chen, W.J.; Chang, S.T. Chemical compositions and larvicidal activities of leaf essential oils from two Eucalyptus species. Bioresour. Technol. 2009, 100, 452–456.
37. Watanabe, K.; Shono, Y.; Kakimizu, A.; Okada, A.; Matsuo, N.; Satoh, A.; Nishimura, H. New mosquito repellent from Eucalyptus camaldulensis. J. Agric. Food Chem. 1993,41, 2164–2166.
38. Siramon, P.; Ohtani, Y. Antioxidative and antiradical activities of Eucalyptus camaldulensis leaf oils from Thailand. J. Wood Sci. 2007, 53, 498–504.
39. Francisco, J.D.C.; Järvenpää, E.P.; Huopalahti, R.; Sivik, B. Comparison of Eucalyptus camaldulensis Dehn. oils from Mozambique as obtained by hydrodistillation and supercritical carbon dioxide extraction. J. Agric. Food Chem. 2001, 49, 2339–2342.
40. Ciftci, O.; Ozdemir, I.; Tanyildizi, S.; Yildiz, S.; Oguzturk, H. Antioxidative effects of curcumin, β-myrcene and 1,8-cineole against 2,3,7,8-tetrachlorodibenzo-p-dioxin-induced oxidative stress in rats liver. Toxicol. Ind. Health 2011, 27, 447–453.
41. Fadel, H.; Marx, F.; el-Sawy, A.; el-Ghorab, A. Effect of extraction techniques on the chemical composition and antioxidant activity of Eucalyptus camaldulensis var. brevirostris leaf oils. Zeitschrift fur Lebensmittel -Untersuchung und -Forschung 1999, 208, 212–216.
42. Hussain, A.I.; Anwar, F.; Chatha, S.A.S.; Jabbar, A.; Mahboob, S.; Nigam, P.S. Rosmarinus officinalis essential oil: Antiproliferative, antioxidant and antibacterial activities. Braz. J. Microbiol. 2010, 41, 1070–1078.
43. Abad, M.J.; Bedoya, L.M.; Apaza, L.; Bermejo, P. The Artemisia L. genus: A review of bioactive essential oils. Molecules 2012, 17, 2542–2566.
44. Buscà, R.; Ballotti, R. Cyclic AMP a key messenger in the regulation of skin pigmentation. Pigment Cell Res. 2000, 13, 60–69.
45. Abdel-Malek, Z.; Swope, V.; Collins, C.; Boissy, R.; Zhao, H.; Nordlund, J. Contribution of melanogenic proteins to the heterogeneous pigmentation of human melanocytes. J. Cell Sci. 1993, 106, 1323–1331.
46. Kameyama, K.; Sakai, C.; Kuge, S.; Nishiyama, S.; Tomita, Y.; Ito, S.; Wakamatsu, K.; Hearing, V.J. The expression of tyrosinase, tyrosinase-related proteins 1 and 2 (TRP1 and TRP2), the silver protein, and a melanogenic inhibitor in human melanoma cells of differing melanogenic activities. Pigment Cell Res./Spons. Eur. Soc. Pigment Cell Res. Int. Pigment Cell Soc. 1995, 8, 97–104.
47. Levy, C.; Khaled, M.; Fisher, D.E. MITF: Master regulator of melanocyte development and melanoma oncogene. Trends Mol. Med. 2006, 12, 406–414.
48. Hirobe, T. Basic fibroblast growth factor stimulates the sustained proliferation of mouse epidermal melanoblasts in a serum-free medium in the presence of dibutyryl cyclic AMP and keratinocytes. Development 1992, 114, 435–445.
49. Galibert, M.D.; Carreira, S.; Goding, C.R. The Usf-1 transcription factor is a novel target for the stress-responsive p38 kinase and mediates UV-induced Tyrosinase expression. EMBO J. 2001, 20, 5022–5031.
50. Singh, S.K.; Sarkar, C.; Mallick, S.; Saha, B.; Bera, R.; Bhadra, R. Human placental lipid induces melanogenesis through p38 MAPK in B16F10 mouse melanoma. Pigment Cell Res. 2005, 18, 113–121.
51. Oyaizu, M. Studies on products of browing reaction: Antioxidative activity of product of browing reaction preapared from glucosamine. Jpn. J. Nutr. 1986, 44, 307–315.
52. Yu, L.; Haley, S.; Perret, J.; Harris, M.; Wilson, J.; Qian, M. Free radical scavenging properties of wheat extracts. J. Agric. Food Chem. 2002, 50, 1619–1624.
53. Emerit, I. Free radicals and aging of the skin. In Free Radicals and Aging; Birkhäuser: Basel, Switzerland, 1992; pp. 328–341.
54. Adama, R.P. Identification of Essential Oil Components by Gas Chromatography/Mass Spectroscopy; Allured Publishing Co.: Carol Stream, IL, USA, 1995; pp. 57–322.
55. Van den Dool, H.; Dec. Kratz, P. A generalization of the retention index system including linear temperature programmed gas—Liquid partition chromatography. J. Chromatogr. A 1963, 11, 463–471.
56. Bilodeau, M.L.; Greulich, J.D.; Hullinger, R.L.; Bertolotto, C.; Ballotti, R.; Andrisani, O.M. BMP-2 stimulates tyrosinase gene expression and melanogenesis in differentiated melanocytes. Pigment Cell Res. 2001, 14, 328–336.
57. Tada, H.; Shiho, O.; Kuroshima, K.-I.; Koyama, M.; Tsukamoto, K. An improved colorimetric assay for interleukin 2. J. Immunol. Methods 1986, 93, 157–165.
58. Tsuboi, T.; Kondoh, H.; Hiratsuka, J.; Mishima, Y. Enhanced melanogenesis induced by tyrosinase gene-transfer increases boron-uptake and killing effect of boron neutron capture therapy for amelanotic melanoma. Pigment Cell Res. 1998, 11, 275–282.
59. Yang, J.Y.; Koo, J.H.; Song, Y.G.; Kwon, K.B.; Lee, J.H.; Sohn, H.S.; Park, B.H.; Jhee, E.C.; Park, J.W. Stimulation of melanogenesis by scoparone in B16 melanoma cells. Acta Pharmacol. Sin. 2006, 27, 1467–1473.
60. Brand-Williams, W.; Cuvelier, M.E.; Berset, C. Use of a free radical method to evaluate antioxidant activity. LWT-Food Sci. Technol. 1995, 28, 25–30.
61. Re, R.; Pellegrini, N.; Proteggente, A.; Pannala, A.; Yang, M.; Rice-Evans, C. Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radic. Biol. Med. 1999, 26, 1231–1237.
62. Murrant, C.L.; Reid, M.B. Detection of reactive oxygen and reactive nitrogen species in skeletal muscle. Microsc. Res. Tech. 2001, 55, 236–248.