Natural Product Sciences

The Korean Society of Pharmacognosy (한국생약학회)
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Microbial Metabolism of Yangonin, a Styryl Lactone from Piper methysticum (Kava)

  • Kim, Ji-Hye (Marine Natural Products Chemistry Laboratory, Korea Ocean Research & Development Institute) ;
  • Kim, Hyun-Jung (Medical Research Center for Gene Regulation and the Brain Korea 21 Project, Chonnam National University Medical School) ;
  • Lee, Ik-Soo (College of Pharmacy and Research Institute of Drug Development, Chonnam National University)
  • Received : 2010.08.26
  • Accepted : 2010.09.08
  • Published : 2010.09.30
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Abstract

Microbial metabolism studies of yangonin (1), a major styryl lactone from Piper methysticum, have resulted in the production of three hydroxylated metabolites (2-4). The chemical structures of these compounds were elucidated to be 4-methoxy-6-(12-hydroxystyryl)-2-pyrone (2),4-methoxy-6-(11,12-dihydroxystyryl)-2-pyrone (3),and 4,12-dimethoxy-6-(7,8-dihydroxy-7,8-dihydrostyryl)-2-pyrone (4) on the basis of the chemical and spectroscopic analyses. The compounds 3 and 4 are reported herein as microbial metabolites of yangonin for the first time.

Keywords

References

  1. Abourashed, E.A. and Khan, I.A., Microbial transformation of kawain and methysticin. Chem. Pharm. Bull., 48, 1996-1998 (2000). https://doi.org/10.1248/cpb.48.1996
  2. Adam, W., Saha-Moeller, C.R., Veit, M., and Welke, B., A convenient synthesis of hispidin from piperonal. Synthesis, 11, 1133-1134 (1994).
  3. Bilia, A.G., Gallori, S., Vincieri, F.F., Kava-kava and anxiety: Growing knowledge about the efficacy and safety. Life Sci., 70, 2581-2597 (2002). https://doi.org/10.1016/S0024-3205(02)01555-2
  4. Clark, A.M., McChesney, J.D., and Hufford, C.D., The use of microorganisms for the study of drug metabolism. Med. Res. Rev., 5, 231-253 (1985). https://doi.org/10.1002/med.2610050203
  5. Dharmaratne, H.R.W., Nanayakkara, N.P.D., and Khan, I.A., Kavalactones from Piper methysticum, and their $^{13}C$ NMR spectroscopic analyses. Phytochemistry, 59, 429-433 (2002). https://doi.org/10.1016/S0031-9422(01)00443-5
  6. Dong, H., Chen, S.X., Xu, H.X., Kadota, S., and Namba, T., A New Antiplatelet Diarylheptanoid from Alpinia blepharocalyx. J. Nat. Prod., 61, 142-144 (1998). https://doi.org/10.1021/np970293i
  7. Duffield, A.M., Jamieson, D.D., Lidgard, R.O., Duffield, P.H., and Bourne, D.J., Identification of some human urinary metabolites of the intoxicating beverage kava. J. Chromatogr., 475, 273-281 (1989). https://doi.org/10.1016/S0021-9673(01)89682-5
  8. Edwards, R.L., Lewis, D.G., and Wilson, D.V., Constituents of the higher fungi. Part I. Hispidin, a new 4-hydroxy-6-styryl-2-pyrone from Polyporus hispidus. J. Chem. Soc., 4995-5002 (1961). https://doi.org/10.1039/jr9610004995
  9. Edwards, R.L. and Mir, I., Constituents of the higher fungi. Part VI. Some analogs of hispidin. J. Chem. Soc., 6, 411-413 (1967).
  10. Hashimoto, T., Suganuma, M., Fujiki, H., Yamada, M., Kohno, T., and Asakawa, X., Isolation and synthesis of $TNF-\alpha$ release inhibitors from Fijian kawa (Piper methysticum). Phytomedicine, 10, 309-317 (2003). https://doi.org/10.1078/094471103322004802
  11. Herath, W., Ferreira, D., Mikell, J.R., and Khan, I.A., Microbial metabolism. Part 5. Dihydrokawain. Chem. Pharm. Bull., 52, 1372- 1374 (2004). https://doi.org/10.1248/cpb.52.1372
  12. Johnson, B.M., Qiu, S.X., Zhang, S., Zhang, F., Burdette, J.E., Yu, L., Bolton, J.L., and van Breemen, R.B., Identification of novel electrophilic metabolites of Piper methysticum Forst (Kava). Chem. Res. Toxicol., 16, 733-740 (2003). https://doi.org/10.1021/tx020113r
  13. Matsuda, H., Hirata, N., Kawaguchi, Y., Naruto, S., Takata, T., Oyama, M., Iinuma, M., and Kubo, M., Melanogenesis stimulation in murine B16 melanoma cells by kava (Piper methysticum) rhizome extract and kavalactones. Biol. Pharm. Bull., 29, 834-837 (2006). https://doi.org/10.1248/bpb.29.834
  14. Rasmussen, A.K., Scheline, R.R., Solheim, E., and Haensel, R., Metabolism of some kava pyrones in the rat. Xenobiotica, 9, 1-16 (1979). https://doi.org/10.3109/00498257909034699
  15. Shao, Y., He, K., Zheng, B., and Zheng, Q., Reversed-phase highperformance liquid chromatographic method for quantitative analysis of the six major kavalactones in Piper methysticum. J. Chromatogr. A, 825, 1-8 (1998). https://doi.org/10.1016/S0021-9673(98)00699-2
  16. Singh, Y.N. and Blumenthal, M., Kava: An Overview. Distribution, mythology, botany, culture, chemistry, and pharmacology of the South Pacific's most revered herb. HerbalGram, 39, 33-55 (1997).
  17. Singh, Y.N. and Singh, N.N., Therapeutic potential of kava in the treatment of anxiety disorders. CNS Drugs, 16, 731-743 (2002). https://doi.org/10.2165/00023210-200216110-00002
  18. Tarbah, F., Mahler, H., Kardel, B., Weinmann, W., Hafner, D., and Daldrup, T., Kinetics of kavain and its metabolites after oral application. J. Chromatogr. B, 789, 115-130 (2003). https://doi.org/10.1016/S1570-0232(03)00046-1
  19. Venisetty, R.K. and Cidii, V., Application of microbial biotransformation for the new drug discovery using natural drugs as substrates. Curr. Pharm. Biotechnol., 4, 153-167 (2003). https://doi.org/10.2174/1389201033489847
  20. Volz, H.P. and Kieser, M., Kava-kava extract WS 1490 versus placebo in anxiety disorders- a randomized placebo-controlled 25-week outpatient trial. Pharmacopsychiatry, 30, 1-5 (1997).
  21. Whitton, P.A., Lau, A., Salisbury, A., Whitehouse, J., and Evans, C.S., Kava lactones and the kava-kava controversy. Phytochemistry, 64, 673-679 (2003). https://doi.org/10.1016/S0031-9422(03)00381-9