Chemistry:Methysticin
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| Preferred IUPAC name
(6R)-6-[(E)-2-(2H-1,3-Benzodioxol-5-yl)ethen-1-yl]-4-methoxy-5,6-dihydro-2H-pyran-2-one | |
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| Properties | |
| C15H14O5 | |
| Molar mass | 274.272 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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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] Additionally, methysticin has been shown to potentiate GABAA receptor activity, contributing to the overall anxiolytic profile of the kava plant.[3]
Toxicity
Methysticin induces the function of the hepatic enzyme CYP1A1. This enzyme is involved in the toxification of benzo[a]pyrene into (+)-benzo[a]pyrene-7,8-dihydrodiol-9,10-epoxide, a highly carcinogenic substance. Another related compound is dihydromethysticin, which also induces the function of CYP1A1.[2][4][5] No report so far has described enhancement of CYP1A1 expression in animals or humans in vivo from any constituent of kava.[6]
References
- ↑ Malani, Joji (2002-12-03). "Evaluation of the effects of Kava on the Liver". Fiji School of Medicine. http://www.spc.int/cis/documents/Kava%20article%20DrMalani.pdf. Retrieved 2009-09-04.
- ↑ 2.0 2.1 "Methysticin and 7,8-dihydromethysticin are two major kavalactones in kava extract to induce CYP1A1.". Toxicological Sciences 124 (2): 388–99. Dec 2011. doi:10.1093/toxsci/kfr235. PMID 21908763.
- ↑ Boonen, G.; Häberlein, H. (1998). "Influence of genuine kavapyrone enantiomers on the GABA-A binding site". Planta Medica 64 (6): 504–506. doi:10.1055/s-2006-957502. PMID 9776662. https://pubmed.ncbi.nlm.nih.gov/9776662/.
- ↑ Beresford, AP (1993). "CYP1A1: friend or foe?". Drug Metab Rev 25 (4): 503–17. doi:10.3109/03602539308993984. PMID 8313840.
- ↑ 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. doi:10.1124/mol.65.5.1225. PMID 15102951.
- ↑ Yamazaki, Yuko; Hashida, Hiroko; Arita, Anna; Hamaguchi, Keiko; Shimura, Fumio (2008). "High dose of commercial products of kava (Piper methysticum) markedly enhanced hepatic cytochrome P450 1A1 mRNA expression with liver enlargement in rats". Food and Chemical Toxicology 46 (12): 3732–3738. doi:10.1016/j.fct.2008.09.052. ISSN 0278-6915. PMID 18930106. https://pubmed.ncbi.nlm.nih.gov/18930106/.
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