Microbial transformation of kawain and methysticin.
The styryl alpha-pyrones, d-kawain (1) and d-methysticin (2) are two of the major kavalactone constituents of the anxiolvtic herb Piper methysticum, commonly known as kava. The use of fungal models to mimic the mammalian metabolism of 1 resulted in the production of 4'-hydroxykawain (1a) from the culture broth of Cunninghamella elegans (ATCC 9245), the same metabolite identified in rat urine. The fungus Torulopsis petrophilum (ATCC 20225) biotransformed 2 to 3'-hydroxy-4'-methoxykawain (2c) which is analogous, but not identical, to a known rat metabolite of methysticin.
Abourashed
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EA
National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences and Department of Phlarmacognosy, School of Pharmacy, The University of Mississippi, University 38677, USA.
Khan
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IA
D000818:Animals; D014151:Anti-Anxiety Agents / Q000378:metabolism / Q000652:urine; D001711:Biotransformation; D020093:Cunninghamella / Q000378:metabolism*; D018696:Neuroprotective Agents / Q000378:metabolism / Q000652:urine; D011714:Pyrans / Q000378:metabolism* / Q000652:urine; D011753:Pyrones / Q000378:metabolism* / Q000652:urine; D051381:Rats
D014151:Anti-Anxiety Agents; D018696:Neuroprotective Agents; D011714:Pyrans; D011753:Pyrones; C076881:methysticin; C011889:kavain