Methysticin
| Methysticin | ||
|---|---|---|
 | ||
| IUPAC name (2R)-2-[(E)-2-(1,3-benzodioxol-5-yl)ethenyl]-4-methoxy-2,3-dihydropyran-6-one | ||
| Identifiers | ||
| CAS number | 495-85-2  | |
| PubChem | 5281567 | |
| Jmol-3D images | {{#if:COC1=CC(=O)O[C@H](C1)/C=C/C2=CC3=C(C=C2)OCO3|Image 1 | |
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| Properties | ||
| Molecular formula | C15H14O5 | |
| Molar mass | 274.27 g mol−1 | |
(verify) (what is: / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | ||
| Infobox references | ||
Methysticin is one of the six major kavalactones found in the kava plant.[1] Research suggests that the CYP1A1 inducing effects of methysticin and the related compound 7,8-dihydromethysticin may indicate that kava has potentially carcinogenic effects.[2]
Toxicity
Methysticin induces the function of the hepatic enzyme CYP1A1, an enzyme involved in the toxification of benzo(a)pyrene (an already very toxic substance) into benzopyrene-7,8-dihydrodiol-9,10-epoxide, one of the most highly carcinogenic substances yet discovered (often called the ultimate carcinogen). This property is shared by the related compound 7,8-dihdromethysticin, both of which occur in significant quantities in Piper methysticum, indicating that kava and its extracts may be carcinogenic.[2][3] As benzo(a)pyrene occurs in tobacco smoke, the carcinogenic effects of tobacco may also be increased by kava consumption.[4]
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References
- ↑ Malani, Joji (2002-12-03). "Evaluation of the effects of Kava on the Liver". Fiji School of Medicine. Retrieved 2009-09-04.
- ↑ 2.0 2.1 Li Y, Mei H, Wu Q, Zhang S, Fang JL, Shi L, Guo L. "Methysticin and 7,8-dihydromethysticin are two major kavalactones in kava extract to induce CYP1A1.". Toxicology Sciences. PMID 21908763.
- ↑ Beresford, AP (1993). "CYP1A1: friend or foe?". Drug Metab Rev 25 (4): 503–17. doi:10.3109/03602539308993984. PMID 8313840.
- ↑ M J Kaiserman, W S Rickert. "Carcinogens in tobacco smoke: benzo[a]pyrene from Canadian cigarettes and cigarette tobacco.". AM J Public Health. PMC 1694072.
See also
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