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Microbial Transformation of a Monoterpene, Geraniol, by the Marine-derived Fungus Hypocrea sp.

  • Leutou, Alain S. (Department of Chemistry, Pukyong National University) ;
  • Yang, Guohua (Department of Chemistry, Pukyong National University) ;
  • Nenkep, Viviane N. (Department of Chemistry, Pukyong National University) ;
  • Siwe, Xavier N. (Department of Chemistry, Pukyong National University) ;
  • Feng, Zhile (Department of Chemistry, Pukyong National University) ;
  • Khong, Thang T. (Department of Chemistry, Pukyong National University) ;
  • Choi, Hong-Dae (Department of Chemistry, Dongeui University) ;
  • Kang, Jung-Sook (College of Dentistry, Pusan National University) ;
  • Son, Byeng-Wha (Department of Chemistry, Pukyong National University)
  • Published : 2009.10.31

Abstract

Geraniol (1) is the biogenetic precursor of a number of monoterpenes. We tested various marine-derived microorganisms to determine their ability to biotransform 1. Only Hypocrea sp. was capable of transforming 1 into its oxidized derivative, 1,7-dihydroxy-3,7-dimethyl-(E)-oct-2-ene (2). The structure of the metabolite obtained was assigned on the basis of detailed spectroscopic data analyses.

Keywords

References

  1. Kitagawa, I. 1982. Natural products from mevalonic acid pathway, pp. 320-338. In S. Shibata, H. Itokawa, U. Sankawa, J. Shoji, and M. Takido (eds.). Natural Products for Medicinal Use. Nanzando Company, Tokyo
  2. Lee, Y. J., B.-G. Kim, Y. Park, Y. Lim, H.-G. Hur, and J.-H. Ahn. 2006. Biotransformation of flavonoids with Omethyltransferase from Bacillus cereus. J. Microbiol. Biotechnol. 16: 1090-1096
  3. Li, X., S.-K. Kim, J. H. Jung, J. S. Kang, H. D. Choi, and B. W. Son. 2005. Biological synthesis of polyketides from 6-npentyl-$\alpha$-pyrone by Streptomyces sp. Bull. Korean Chem. Soc. 26: 1889-1890 https://doi.org/10.5012/bkcs.2005.26.11.1889
  4. Li, X., Y. H. Kim, J. H. Jung, J. S. Kang, D.-K. Kim, H. D. Choi, and B. W. Son. 2007. Microbial transformation of the bioactive sesquiterpene, cyclonerodiol, by the ascomycete Penicillium sp. and the actinomycete Streptomyces sp. Enz. Microbial Technol. 40: 1188-1192 https://doi.org/10.1016/j.enzmictec.2006.09.002
  5. Li, X., S. M. Lee, H. D. Choi, J. S. Kang, and B. W. Son. 2003. Microbial transformation of terreusinone, an ultraviolet-A (UVA) protecting dipyrroloquinone, by Streptomyces sp. Chem. Pharm. Bull. 51: 1458-1459 https://doi.org/10.1248/cpb.51.1458
  6. Mateo, J. J., N. Gentilini, T. Huerta, M. Jimenez, and R. Di Stefano. 1997. Fractionation of glycoside precursors of aroma in grapes and wine. J. Chromatogr. A 778: 219-224 https://doi.org/10.1016/S0021-9673(97)00566-9
  7. Park, M.-K., K.-H. Liu, Y. Lim, Y.-H. Lee, H.-G. Hur, and J.-H. Kim. 2003. Biotransformation of a fungicide ethaboxam by soil fungus Cunninghamella elegans. J. Microbiol. Biotechnol. 13:43-49
  8. Rasor, J. P. and E. Voss. 2001. Enzyme-catalyzed processes in pharmaceutical industry. Appl. Catal. A Gen. 221: 145-158 https://doi.org/10.1016/S0926-860X(01)00804-3
  9. Skouroumounis, G. K. and M. A. Sefton. 2000. Acid-catalyzed hydrolysis of alcohols and their $\beta$-D-glucopyranosides. J. Agric. Food Chem. 48: 2033-2039 https://doi.org/10.1021/jf9904970
  10. Smith, R. V. and J. P. Rosazza. 1975. Microbial models of mammalian metabolism. J. Pharm. Sci. 64: 1737-1759 https://doi.org/10.1002/jps.2600641104
  11. Takabe, K., T. Katagiri, and J. Tanaka. 1975. A new route to 3,7-dimethyl-2,6-octadien-1-ol and 3,7-dimethyl-2-octene-1,7-diol from isoprene. Chem. Lett. 1031-1032
  12. Tang, W. and G. Eisenbrand (Eds.). 1992. Chinese Drugs of Plant Origin, pp. 87-93. Springer-Verlag, Berlin

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