Microbial Metabolism of Yangonin, a Styryl Lactone from Piper Methysticum(Kava)
Natural Product Sciences 16(3) : 148-152 (2010) Microbial Metabolism of Yangonin, a Styryl Lactone from Piper methysticum (Kava) Ji Hye Kim1, Hyun Jung Kim2, and Ik-Soo Lee* College of Pharmacy and Research Institute of Drug Development, Chonnam National University, Gwangju 500-757, Republic of Korea 1Marine Natural Products Chemistry Laboratory, Korea Ocean Research & Development Institute, Ansan 426-744, Republic of Korea 2Medical Research Center for Gene Regulation and the Brain Korea 21 Project, Chonnam National University Medical School, Gwangju 501-746, Republic of Korea 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 − Microbial metabolism, Yangonin, Styryl lactone, Piper methysticum, Kava Introduction et al., 2003) studies provided several derivatives or metabolites including glucuronylated, hydroxylated, deme- The roots of the kava shrub (Piper methysticum G. thylated, and dehydrated metabolites. Microbial metabolism Forst, Piperaceae) have been used to prepare an intoxicating studies on kavalactones have been reported for kawain, beverage for South Pacific Islanders’ social occasions methysticin (Abourashed and Khan, 2000), and dihydro- (Whitton, et al., 2003). In Western countries, kava extracts kawain (Herath, et al., 2004).
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