Methysticin

Methysticin
Names
	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 ;
3D model (JSmol)	Interactive image;
ChemSpider	4444889 ;
KEGG	C09952 ;
PubChem CID	5281567;
UNII	M832AIJ6HX ;
CompTox Dashboard (EPA)	DTXSID5033674 ;
	InChI InChI=1S/C15H14O5/c1-17-12-7-11(20-15(16)8-12)4-2-10-3-5-13-14(6-10)19-9-18-13/h2-6,8,11H,7,9H2,1H3/b4-2+/t11-/m0/s1 Key: GTEXBOVBADJOQH-FWEMWIAWSA-N ; InChI=1/C15H14O5/c1-17-12-7-11(20-15(16)8-12)4-2-10-3-5-13-14(6-10)19-9-18-13/h2-6,8,11H,7,9H2,1H3/b4-2+/t11-/m0/s1 Key: GTEXBOVBADJOQH-FWEMWIAWBD;
	SMILES COC1=CC(=O)O[C@H](C1)/C=C/C2=CC3=C(C=C2)OCO3;
Properties
Chemical formula	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).

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. 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]^[3]^[4]

References

^ Malani, Joji (2002-12-03). "Evaluation of the effects of Kava on the Liver" (PDF). Fiji School of Medicine. Archived from the original (PDF) on 2009-03-20. Retrieved 2009-09-04.
^ ^a ^b 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". Toxicological Sciences. 124 (2): 388–99. doi:10.1093/toxsci/kfr235. PMC 5736320. PMID 21908763.
^ 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. S2CID 24627183.

[Malani-1] Malani, Joji (2002-12-03). "Evaluation of the effects of Kava on the Liver" (PDF). Fiji School of Medicine. Archived from the original (PDF) on 2009-03-20. Retrieved 2009-09-04.

[pmid21908763-2] 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". Toxicological Sciences. 124 (2): 388–99. doi:10.1093/toxsci/kfr235. PMC 5736320. PMID 21908763.

[Beresford_AP-3] Beresford, AP (1993). "CYP1A1: friend or foe?". Drug Metab Rev. 25 (4): 503–17. doi:10.3109/03602539308993984. PMID 8313840.

[Uno_et_al-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. doi:10.1124/mol.65.5.1225. PMID 15102951. S2CID 24627183.

[1]

[2]

[3]

[4]

Names


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
3D model (JSmol)	Interactive image
ChemSpider	4444889
KEGG	C09952
PubChem CID	5281567
UNII	M832AIJ6HX
CompTox Dashboard (EPA)	DTXSID5033674
InChI InChI=1S/C15H14O5/c1-17-12-7-11(20-15(16)8-12)4-2-10-3-5-13-14(6-10)19-9-18-13/h2-6,8,11H,7,9H2,1H3/b4-2+/t11-/m0/s1 Key: GTEXBOVBADJOQH-FWEMWIAWSA-N InChI=1/C15H14O5/c1-17-12-7-11(20-15(16)8-12)4-2-10-3-5-13-14(6-10)19-9-18-13/h2-6,8,11H,7,9H2,1H3/b4-2+/t11-/m0/s1 Key: GTEXBOVBADJOQH-FWEMWIAWBD
SMILES COC1=CC(=O)O[C@H](C1)/C=C/C2=CC3=C(C=C2)OCO3
Properties
Chemical formula	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).