HOME JOURNALS CONTACT

Pakistan Journal of Biological Sciences

Year: 2004 | Volume: 7 | Issue: 10 | Page No.: 1735-1740
DOI: 10.3923/pjbs.2004.1735.1740
Isolation and Identification of an Antifungal Sesquiterpene Alcohol from Amboyna Wood
Irawan W. Kusuma, Tomoko Ogawa, Kazutaka Itoh and Sanro Tachibana

Abstract: An antifungal compound was isolated from the n-hexane solubles in methanolic extracts of amboyna wood by bioassay-guided fractionation using Pleurotus pulmonarius, a wood-rotting fungus. The compound was identified as β-eudesmol, a sesquiterpene alcohol with an eudesmane skeleton, based on instrumental analyses (Ultraviolet absorption, Mass spectrometry and 1H and 13C-Nuclear Magnetic Resonance spectroscopy) and a melting point test. The compound showed 21% of the antifungal activity of the methanolic extract as a control. Antifungal assays against P. pulmonarius showed that addition of β-eudesmol at different concentrations affected the inhibition of fungal growth. Furthermore, the activity to inhibit the growth of P. pulmonarius seemed to be dependent on the concentration of β-eudesmol.

Fulltext PDF

How to cite this article
Irawan W. Kusuma, Tomoko Ogawa, Kazutaka Itoh and Sanro Tachibana, 2004. Isolation and Identification of an Antifungal Sesquiterpene Alcohol from Amboyna Wood. Pakistan Journal of Biological Sciences, 7: 1735-1740.

Keywords: amboyna wood, antifungal compound, β- eudesmol, bioassay guided fractionation and sesquiterpene

REFERENCES
  • Tachibana, S. and M. Sumimoto, 1989. Utilization of forest resources by microbial, enzymatical and chemical conversion I. Mokuzai Gakkaishi, 35: 42-50.

  • Tachibana, S., E. Watanabe, K. Itoh and T. Oki, 1994. Formation of taxol in Taxus cuspidata Sieb. et Zucc. variety nana rehder callus cultures. Mokuzai Gakkaishi, 40: 1254-1258.
    Direct Link    

  • Miyata, M., K. Itoh and S. Tachibana, 1998. Extractives of Juniperus chinensis L. I: Isolation of podophyllotoxin and yatein from the leaves of J. chinensis. J. Wood Sci., 44: 397-400.
    CrossRef    Direct Link    

  • Muranaka, T., M. Miyata, K. Itoh and S. Tachibana, 1998. Production of podophyllotoxin in Juniperus chinensis callus cultures treated with oligosaccharides and a biogenetic precursor. Phytochemistry, 49: 491-496.
    CrossRef    Direct Link    

  • Premjet, D., I. Kazutaka and T. Sanro, 2002. Stimulation of the production of podophyllotoxin by biogenetic precursors and an elicitor in Juniperus chinensis stem-derived callus cultures. Pak. J. Biol. Sci., 5: 313-316.
    CrossRef    Direct Link    

  • Yoshida, M., M. Toshio, I. Kazutaka and T. Sanro, 2002. Stimulation of the production of taxol by oligosaccharides in Taxus cuspidate variety nana callus cultures. Pak. J. Biol. Sci., 5: 461-465.
    CrossRef    Direct Link    

  • Ogata, K., 1985. Classification of Tropical Woods: Nihon Mokuzai Kako Gijutus Kyokai. New Japan Printing Co., Tokyo, Japan, pp: 40-41

  • Burkill, J.H., 1966. A Dictionary of Economic Products of the Malay Peninsula. Vol. 2, Art Printing Works Publishers, Kuala Lumpur, Malaysia

  • Hartwell, J.L., 1980. Plants Used Against Cancer. Quaterman, Lawrence, MA

  • Endo, H. and Y. Miyazaki, 1972. Antitumor substances in the leaves of Pterocarpus indicus and Pterocarpus vidalianus. Bull. Natl. Inst. Hyg. Sci., 90: 69-71.

  • Lewis, W.H. and M.P.H. Elvin-Lewis, 1977. Medical Botany. John Wiley and Sons Ltd., New York

  • Perry, L.M., 1980. Medicinal Plants of East and South-East Asia: Attributed Properties and Uses. MIT Press, Cambridge, Masachusetts and London, pp: 224

  • Khan, M.R. and A.D. Omoloso, 2003. Antibacterial activity of Pterocarpus indicus. Fitoterapia, 74: 603-605.

  • Adinarayana, D. and K.V. Syamasundar, 1982. A new sesquiterpene alcohol from Pterocarpus marsupium. Phytochemistry, 21: 1083-1085.

  • Parthasarathy, M.R. and T.R. Seshadri, 1965. Occurrence of β-eudesmol and pterocarpol in the heartwoods of Pterocarpus indicus and P. macrocarpus. Curr. Sci., 34: 115-116.

  • Varma, K.R., T.C. Jain and S.C. Bhattacharyya, 1962. Terpenoids-XXXIV: Structure and stereochemistry of zingiberol and juniper champor. Tetrahedron, 18: 979-984.

  • Barton, D.H.R., J.C. Beloeil, A. Billion, J. Boivin, J.V. Lallemand, P. Lelandais and S. Mergui, 1987. Functionalisation of saturated hydrocarbons. Part XI. Oxidation of cedrol, β-and γ-eudesmols, sclareol, manoyl oxide, 1, 9-dideoxyforskolin, methyl trans-dihydrojasmonate and tetrahydrolinalool by the Gif system. Helvetica Chim. Acta, 70: 2187-2199.

  • Cornwell, C.P., N. Reddy, D.N. Leach and S.G. Wyllie, 2000. Hydrolysis of hedycaryol: The origin of the eudesmol in the Myrtaceae. Flavour Fragrance J., 15: 421-431.

  • Threlfall, D.R. and I.M. Whitehead, 1991. Terpenoid Phytoalexins: Aspect of Biosynthesis, Catabolism and Regulation. In: Ecological Chemistry and Biochemistry of Plant Terpenoids, Harborne, J.B. and F.A. Thomas-Barberan (Eds.). Oxford Science Publication, Oxford, UK., pp: 159-208

  • Sundin, A., H. Anke, K. Bergquist, A. Mayer, W. Sheldrick, M. Stadler and O. Sterner, 1993. The structure determination of panellon and panellol, two 14-noreudesmanes isolated from Resupinatus leightonii. Tetrahedron, 49: 7519-7524.

  • Rudman, P., 1965. The causes of natural durability in timber. XVII. The causes of decay and termite resistance in Callitris columellaris. Holzforschung, 19: 52-57.

  • Achenbach, H., W. Reiner and I. Addae-Mensah, 1985. Sesquiterpenes from Carissa edulis. Phytochemistry, 24: 2325-2328.
    CrossRef    Direct Link    

  • Su, W.C., J.M. Fang and Y.S. Cheng, 1994. Sesquiterpenes from leaves of Cryptomeria japonica. Phytochemistry, 39: 603-607.

  • Mariotti, J.P., F. Tomi, J. Cassanova, J. Costa and F. Bernardini, 1997. Composition of the essential oil of Cistus ladaniferus L. cultivated in Corsica (France). Flavour Fragrance J., 12: 147-151.

  • Matsuda, H., T. Kageura, M. Oda, T. Morikawa, Y. Sakamoto and M. Yoshikawa, 2001. Effects of constitutent from the bark of Magnolia obovata on nitric oxide production in lipopolysaccharide-activated macrophages. Chem. Pharm. Bull., 49: 716-720.

  • Arora, C.K., R.B. Arora, C.K. Mesta, S.N. Shanbag, R. Seshari, M.L. Maheshari and S.C. Battacharya, 1967. Hypotensive activity of β-eudesmol and some related sesquiterpenes. Indian J. Med. Res., 55: 463-472.

  • Kiso, Y., M. Tohkin and H. Hikino, 1983. Antihepatotoxic principles of Atractylodes rhizomes. J. Nat. Prod., 46: 651-654.

  • Chiou, L.C., J.Y. Ling and C.C. Chang, 1997. Chinese herbs constituent β-eudesmol alleviated the electroshock seizures in mice and electrographic seizures in rat hippocampal slices. Neurosci. Lett., 231: 171-174.

  • Miyakado, M., T. Kato, N. Ohno and T.J. Mabry, 1975. Pinocembrin and (+)-β-eudesmol from Hymenoclea monogyra and Bacharis glutinosa. Phytochemistry, 15: 846-846.

  • Pregosin, P.S., E.W. Randall and T.B.H. McMurry, 1972. 13C fourier studies. The configurational dependence of the carbon-13 chemical shifts in santonin derivatives. J. Chem. Soc. Perkin Trans., 1: 299-301.
    CrossRef    Direct Link    

    • © Science Alert. All Rights Reserved