Biosynthesis of Eudesmane-type Sesquiterpenoids by The Wood-rotting Fungus, Polyporus brumalis, on Specific Medium, including Inorganic Magnesium Source

Lee, Su-Yeon;Ryu, Sun-Hwa;Choi, In-Gyu;Kim, Myungkil

  • Received : 2016.01.29
  • Accepted : 2016.03.12
  • Published : 2016.03.25


Fungi, such as the wood-rotting Polyporus brumalis, are excellent sources of pharmaceutically interesting natural products such as sesquiterpenoids. In this study, we investigated the biosynthesis of P. brumalis sesquiterpenoids on modified medium. Ten additional species of white rot fungi were inoculated in medium containing nutrients such as $C_6H_{12}O_6$, $C_4H_{12}N_2O_6$, $KH_2PO_4$, $MgSO_4$, and $CaCl_2$ at $28^{\circ}C$ for 25 days. After 10 days of incubation, eudesmane-type sesquiterpenes, ${\beta}$-eudesmane and ${\beta}$-eudesmol, were only synthesized during the growth phase of P. brumalis. Experiments excluding one nutrient at a time were conducted to determine the effects of inorganic nutrients on sesquiterpene biosynthesis. In conclusion, GC-MS analysis showed that biosynthesis of sesquiterpenes was differentially regulated by inorganic nutrients such as $MgSO_4$, $C_4H_{12}N_2O_6$, and $KH_2PO_4$. We found $MgSO_4$ supplementation to be vital for eudesmane-type sesquiterpene biosynthesis in P. brumalis; nitrogen ($C_4H_{12}N_2O_6$) and phosphate ($KH_2PO_4$) inhibited the synthesis of P. brumalis metabolites. Magnesium is a known cofactor of sesquiterpene synthase, which promotes ${\beta}$-eudesmol synthesis. To mechanistically understand eudesmane-type sesquiterpene biosynthesis in P. brumalis, further research into the genes regulating the dynamics of such biosynthesis is warranted.


wood rot fungi;Polyporus brumalis;sesquiterpene biosynthesis;${\beta}$-eudesmol


  1. Abrahanr, W.-R., Abate, D. 1995. Chromanones from Lentinus crinitus (basidiomycetes).
  2. Agger, S.A., Lopez-Gallego, F., Hoye, T.R., Schmidt-Dannert, C. 2008. Action of sesquiterpene synthases from Nostoc punctiforme PCC 73102 and Nostoc sp. strain pcc 7120. 190(18): 6084-6096.
  3. Buckley, S.L., Harwood, L.M., Macias-Sanchez, A.J. 2002. Synthesis of (${\pm}$)-mevalonic acid lactone via a meso-dialdehyde: a model for desymmetrization. ARKIVOC 8: 46-56.
  4. Calvo, A.M., Wilson, R.A., Bok, J.-W., Keller, N.P. 2008. Relationship between secondary metabolism and fungal development. 66: 447-459.
  5. Daniewski, W., Vidari, G. 1999. Constituents of Lactarius (mushrooms). Pages 69-171. Fortschritte der chemie organischer naturstoffe/Progress in the chemistry of organic natural products, Springer.
  6. Degenhardt, J., Kollner, T.G., Gershenzon, J. 2009. Monoterpene and sesquiterpene synthases and the origin of terpene skeletal diversity in plants. Phytochemistry 70: 1621-1637.
  7. Dondorp, A.M., Nosten, F., Yi, P., Das, D., Phyo, A.P., Tarning, J., Lwin, K.M., Ariey, F., Hanpithakpong, W., Lee, S.J. 2009. Artemisinin resistance in Plasmodium falciparum malaria. New England journal of medicine 361: 455-467.
  8. Fleck, W.F., Schlegel, B., Hoffmann, P., Ritzau, M., Heinze, S., Grafe, U. 1996. Isolation of isodrimenediol, a possible intermediate of drimane biosynthesis from Polyporus arcularius. Journal of natural products 59: 780-781.
  9. Fraga, B.M. 1999. Natural sesquiterpenoids. Natural product reports 16: 711-730.
  10. Harper, D.B., Buswell, J.A., Kennedy, J.T. 1991. Effect of chloromethane on veratryl alcohol and lignin peroxidase production by the fungus Phanerochaete chrysosporium. Journal of general microbiology 137: 2867-2872.
  11. Hoffmann, P., Esser, K. 1978. Genetics of speciation in the basidiomycetous genus Polyporus. Theoretical and applied genetics 53: 273-282.
  12. Hoffmeister, D., Keller, N.P. 2007. Natural products of filamentous fungi: enzymes, genes, and their regulation. Natural product reports 24: 393-416.
  13. Morath, S.U., Hung, R., Bennett, J.W. 2012. Fungal volatile organic compounds: A review with emphasis on their biotechnological potential. British mycological society. 26: 73-83.
  14. Olennikov, D.N., Agafonova, SyV., Penzina, TyA., Borovskii, G.B. 2014. Fatty acid composition of fourteen wood-decaying basidiomycete species growing in permafrost conditions. Records of natural products 8.
  15. Polovinka, M.P., Korchagina, D.V., Gatilov, Y.V., Bagrianskaya, I.Y., Barkhash, V.A., Perutskii, V.B., Ungur, N.D., Vlad, P.F., Shcherbukhin, V.V., Zefirov, N.S. 1994. Cyclization and rearrangements of farnesol and nerolidol stereoisomers in superacids. The Journal of organic chemistry 59: 1509-1517.
  16. Rowinsky, E.K., Onetto, N., Canetta, R., Arbuck, S. 1992. Taxol: the first of the taxanes, an important new class of antitumor agents. Seminars in oncology. pp. 646-662.
  17. Schmidt, O. 2006. Wood and tree fungi: Springer.
  18. Schuffler, A., Anke, T. 2009. Secondary metabolites of basidiomycetes. Physiology and genetics, Springer. pp. 209-231.
  19. Seo, M.-J., Kim, S.-J., Kang, T.-H., Rim, H.-K., Jeong, H.-J., Um, J.-Y., Hong, S.-H., Kim, H.-M. 2011. The regulatory mechanism of ${\beta}$-eudesmol is through the suppression of caspase-1 activation in mast cell-mediated inflammatory response. Immunopharmacology and immunotoxicology 33: 178-185.
  20. Toyomasu, T., Tsukahara, M., Kaneko, A., Niida, R., Mitsuhashi, W., Dairi, T., Kato, N., Sassa, T. 2007. Fusicoccins are biosynthesized by an unusual chimera diterpene synthase in fungi. Proceedings of the national academy of sciences 104: 3084-3088.
  21. Tsuneki, H., Ma, E.-L., Kobayashi, S., Sekizaki, N., Maekawa, K., Sasaoka, T., Wang, M.-W., Kimura, I. 2005. Antiangiogenic activity of ${\beta}$-eudesmol in vitro and in vivo. European journal of pharmacology 512: 105-115.
  22. Wu, Q.-X., Shi, Y.-P., Jia, Z.-J. 2006. Eudesmane sesquiterpenoids from the Asteraceae family. Natural product reports 23: 699-734.


Grant : 목재이용 기반기술 연구

Supported by : 국립산림과학원