Comparison of Antifungal Activites of Monoterpenes and Sesquiterpenes in Essential Oil from Chamaecyparis obtusa against Dermatophytes

피부사상균에 대한 편백정유의 Mono- 및 Sesquiterpene 항진균 활성 비교

  • Gwak, Ki-Seob (Dept. of Forest Sciences, College of Agriculture & Life Sciences, Seoul National University) ;
  • Park, Mi-Jin (Dept. of Forest Sciences, College of Agriculture & Life Sciences, Seoul National University) ;
  • Jeung, Eui-Bae (College of Veterinary Medicine, Chungbuk National University) ;
  • Chang, Je-Won (Enbita Co. LTD.) ;
  • Choi, In-Gyu (Dept. of Forest Sciences, College of Agriculture & Life Sciences, Seoul National University)
  • 곽기섭 (서울대학교 농업생명과학대학 산림과학부) ;
  • 박미진 (서울대학교 농업생명과학대학 산림과학부) ;
  • 정의배 (충북대학교 수의과대학 수의학과) ;
  • 장제원 (엔바이타(주)) ;
  • 최인규 (서울대학교 농업생명과학대학 산림과학부)
  • Received : 2006.02.24
  • Accepted : 2006.03.28
  • Published : 2006.05.25

Abstract

This study was to compare the antifungal activitiy of monoterpenes with that of sesquiterpenes, which were major constituents of antifungal active essential oil of Chamaecyparis obtusa, to investigate which constituents had more effective against dermatophytes, and to evaluate the synergistic effect of combination of the antifungal active constituents. The antifungal activities of seven fractions (A, B, C, D, E, F, and G) from C obtusa essential oil by column chromatography were tested against Trichophyton mentagrophytes. Fraction D, E, F, and G were more active than fraction A, B, and C, and their major compounds were mono- and sesquiterpenes analyzed by GC/MS. Borneol, linalool, and ${\alpha}$-terpineol were selected as monoterpenes, and ${\alpha}$-cedrol, nerolidol, and ${\beta}$-eudesmol as sesquiterpenes, respectively. The antifungal activities of the constituents were respectively examined against Trichophyton mentagrophytes (KCTC6077), Microsporum canis (KCTC6591), and Microsporum gypseum. The constituents of sesquiterpenes were more active than those of monoterpenes. By comparing single and combined sesquiterpenes with fraction F containing the higher ratio of sesquiterpenes, combined sesquiterpenes were the most active. This result indicated that there was the synergistic antifungal effect against dermatophytes when sesquiterpenes were combined together.

본 연구는 피부사상균에 항진균 활성을 보이는 편백정유에 대하여 이를 구성하고 있는 mono- 및 sesquiterpene 성분들 중 어떠한 성분들에 의해 항진균 활성이 나타나는지 탐색하고 성분들 간의 synergy 효과가 존재하는지 알아보고자 피부사상균인 Trichophyton mentagrophytes (KCTC6077), Microsporum canis (KCTC6591), Microsporum gypseum에 대하여 디스크확산법, 한천희석법을 이용하여 항진균 활성을 평가, 비교하였다. Column chromatography를 이용하여 편백정유를 7개(A, B, C, D, E, F, G)로 분획하고, 각각의 분획들에 대하여 한천희석법을 이용하여 T. mentagrophytes에 대한 항진균 활성을 실험한 결과, 분획 D, E, F, G의 항진균 활성이 높았다. GC/MS 분석을 실시하여 높은 항진균 활성을 나타내는 분획의 주성분을 확인하고 그 중 monoterpene인 borneol, linalool, ${\alpha}$-terpineol과, sesquiterpene인 ${\alpha}$-cedrol, nerolidol, ${\beta}$-eudesmol을 선택하였다. 단일 terpene의 항진균 활성 비교 시 monoterpene보다 sesquiterpene이 더 높은 활성을 보였다. 높은 활성을 보이는 sesquiterpene의 단일 및 혼합 성분들과 편백정유의 분획 중 항진균 활성이 높고 sesquiterpene의 함유량이 높은 분획 F의 비교 시, sesquiterpene의 조합 성분들이 높은 항진균 활성을 나타냈다. 이는 sesquiterpene 성분들의 혼합에 의하여 항진균 활성의 synergy 효과가 발현됨을 의미하였다.

Keywords

Acknowledgement

Supported by : 농림기술관리센타

References

  1. 박미진, 이수민, 곽기섭, 정의배, 장제원, 최인규, 2005 피부사상균 Microsporum canis 및 Trichophyton mentagrophytes에 대한 편백정유의 항진균활성물칠 탐색, 목재공학 33(3): 72-78
  2. 이성숙, 강하영, 최인규. 2002. 수목 정유의 생리활성에 관한 연구( I ) 목재공학 30(1): 48-55
  3. 이현욱, 백승화, 한동민. 2001. 편백정유의 항균효과. Kor. J. Appl. Microbiol. Biotechnol. 29(4): 253-257
  4. 홍철운, 김철생, 김남균, 김영희. 2001. 편백과 화백의 잎 과 열매에서 분리한 정유성분의 조성. J. Korea Soc. Agric. Chem. Biotechnol. 44(2): 116-121
  5. Bauer, K., D. Garbe, and H. Surburg. 2001. Common fragrance and flavor materials: preparation, properties and uses. Wiley-VCH, Weinheim: p. 293
  6. Carson, C.F. and T.V. Riley. 1995. Antimicrobial activity of the major components of the essential oil of Melaleuca alternifolia. J Appl. Bacteriol. 78(3): 264- 269 https://doi.org/10.1111/j.1365-2672.1995.tb05025.x
  7. Carson, C. F., B. J. Mee, and T. V. Riley. 2002. Mechanism of action of Melaleuca alternifolia (tea tree) oil on Staphylococcus aureus determined by time-kill, lysis, leakage, and salt tolerance assays and electron microscopy. Antimicrob. Agents Ch. 46: 1914 -1920. https://doi.org/10.1128/AAC.46.6.1914-1920.2002
  8. Cassella, S., John P. Cassella, and I. Smith. 2002. Synergistic antifungal activity of tea tree (Melaleuca alternifolia) and lavender (Lavandula angustifolia) essential oils against dermatophyte infection. The International Journal of Aromatherapy 12(1): 2-15 https://doi.org/10.1054/ijar.2001.0127
  9. Cox, S. D., C. M. Mann, J. L. Markham, H. C. Bell, J. E. Gustafson, J. R. Warmington, and S. G. Wyllie. 2000. The mode of antimicrobial action of the essential oil of Melaleuca alternifolia (tea tree oil). J Appl. Microbiol. 88: 170-175 https://doi.org/10.1046/j.1365-2672.2000.00943.x
  10. Cox, S. D., C. M. Mann, and J. L. Markham. 2001. Interaction between components of the essential oil of Melaleuca alternifolia. J. Appl. Microbiol. 91: 492-497 https://doi.org/10.1046/j.1365-2672.2001.01406.x
  11. Griffin, Shane G., S. Grant Wyllie, Julie L. Markham, and David N. Leach. 1999. The role of structure and molecular properties of terpenoids in determining their antimicrobial activity. Flavour Frag. J. 14: 322-332 https://doi.org/10.1002/(SICI)1099-1026(199909/10)14:5<322::AID-FFJ837>3.0.CO;2-4
  12. Hammer, K. A., C. F. Carson, and T. V. Riley. 2002. In vitro activity of Melaleuca alternifolia (tea tree) oil against dermatophytes and other filamentous fungi. J. Antimicrob. Chemother. 50: 195-199 https://doi.org/10.1093/jac/dkf112
  13. Hammer, K. A., C. F. Carson, and T. V. Riley. 2003Antifungal activity of the components of Melaleuca alternifolia(tea tree) oil. J. Appl. Microbiol. 95: 853-860 https://doi.org/10.1046/j.1365-2672.2003.02059.x
  14. Marino, M, C Bersani, and G. Comi. 2001. Impedance measurements to study the antimicrobial activity of essential oils from Lamiacea and Compositae. Int. J. Food Microbiol. 67: 187-195 https://doi.org/10.1016/S0168-1605(01)00447-0
  15. Paster, N., M. Menasherov, U. Ravid, and B. Juven. 1995. Antifungal activity of oregano and thyme essential oils applied as fumigants against fungi attacking stored grain. J. Food Prot. 58(1): 81-85 https://doi.org/10.4315/0362-028X-58.1.81
  16. Price, S. and L. Price. 1999. Aromatherapy for Health Professionals. 2nd edn. Churchill Livingstone, London
  17. Senatore, F. 1996. Influence of harvesting time on yield and composition of the essential oil of thyme (Thymus pulegioides L.) growing wild in Compania (Southern Italy). J. Agric. Food Chem. 44: 1327-1332 https://doi.org/10.1021/jf950508z
  18. Sikkema, J., J. A. M.de Bont, and B. Poolman. 1995. Mechanisms of membrane toxicity of hydrocarbons. Microbiological Reviews 59: 201-222
  19. Uribe, S., J. Ramirez, and A. Pena. 1985. Effects of $\beta$ -pinene on yeast membrane functions. J Bacterial 161: 1195-1200