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Open Access Articles- Top Results for Methysticin

Methysticin

Methysticin
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IUPAC name
(2R)-2-[(E)-2-(1,3-Benzodioxol-5-yl)ethenyl]-4-methoxy-2,3-dihydropyran-6-one
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495-85-2 7pxY
ChemSpider 4444889 7pxN
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KEGG C09952 7pxN
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C15H14O5
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Infobox references

Methysticin is one of the six major kavalactones found in the kava plant.[1] Research suggests that methysticin and the related compound dihydromethysticin have CYP1A1 inducing effects which may be responsible for their toxicity.[2]

Toxicity

Methysticin induces the function of the hepatic enzyme CYP1A1, an enzyme involved in the toxification of benzo[a]pyrene into benzopyrene-7,8-dihydrodiol-9,10-epoxide, one of the most highly carcinogenic substances known. This property is shared by the related compound dihdromethysticin, both of which occur in significant quantities in Piper methysticum.[2][3][4]

References

  1. Malani, Joji (2002-12-03). "Evaluation of the effects of Kava on the Liver" (PDF). Fiji School of Medicine. Retrieved 2009-09-04. 
  2. 2.0 2.1 Li Y, Mei H, Wu Q, Zhang S, Fang JL, Shi L, Guo L (Dec 2011). "Methysticin and 7,8-dihydromethysticin are two major kavalactones in kava extract to induce CYP1A1.". Toxicology Sciences 124 (2): 388–99. PMID 21908763. doi:10.1093/toxsci/kfr235. 
  3. Beresford, AP (1993). "CYP1A1: friend or foe?". Drug Metab Rev 25 (4): 503–17. PMID 8313840. doi:10.3109/03602539308993984. 
  4. Uno, S; Dalton TP; Durkenne S; Curran CP (2004). "Oral exposure to benzo[a]pyrene in the mouse: detoxication by inducible cytochrome P450 is more important than metabolic activation.". Molecular Pharmacology 65 (5): 1225–37. PMID 15102951. doi:10.1124/mol.65.5.1225.