Flavokavain A

Flavokavain A
Names
	Preferred IUPAC name 2′-Hydroxy-4,4′,6′-trimethoxychalcone
	Other names Flavokawain A
Identifiers
CAS Number	37951-13-6 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	2224776
ChEBI	CHEBI:157725;
ChEMBL	ChEMBL243829;
ChemSpider	4511445;
EC Number	636-475-1;
PubChem CID	5355469;
UNII	8OM2XZ2ZM3 ;
CompTox Dashboard (EPA)	DTXSID601317535 ;
	InChI InChI=1S/C18H18O5/c1-21-13-7-4-12(5-8-13)6-9-15(19)18-16(20)10-14(22-2)11-17(18)23-3/h4-11,20H,1-3H3/b9-6+ Key: CGIBCVBDFUTMPT-RMKNXTFCSA-N;
	SMILES O=C(C2=C(O)C=C(OC)C=C2OC)/C=C/C1=CC=C(OC)C=C1;
Properties
Chemical formula	C18H18O5
Molar mass	314.337 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Flavokavain A is a flavokavain found in the kava plant.^[1] It induces apoptosis in bladder cancer cells via a Bax protein-dependent and mitochondria-dependent apoptotic pathway.^[2]

Flavokavains A and B enhance hepatotoxicity of paracetamol, underscoring a potentially serious interaction between paracetamol and kava.

References

^ Dharmaratne, H. Ranjith W.; N. P. Dhammika Nanayakkara; Ikhlas A. Khan (February 2002). "Kavalactones from Piper methysticum, and their 13C NMR spectroscopic analyses". Phytochemistry. 59 (4): 429–33. doi:10.1016/S0031-9422(01)00443-5. PMID 11830162.
^ Zi X, Simoneau AR (April 2005). "Flavokawain A, a novel chalcone from kava extract, induces apoptosis in bladder cancer cells by involvement of Bax protein-dependent and mitochondria-dependent apoptotic pathway and suppresses tumor growth in mice" (PDF). Cancer Research. 65 (8): 3479–86. doi:10.1158/0008-5472.CAN-04-3803. PMID 15833884.

External links

Flavokawain A at the United States National Library of Medicine

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[Dharmaratne_2002-01-30-1] Dharmaratne, H. Ranjith W.; N. P. Dhammika Nanayakkara; Ikhlas A. Khan (February 2002). "Kavalactones from Piper methysticum, and their 13C NMR spectroscopic analyses". Phytochemistry. 59 (4): 429–33. doi:10.1016/S0031-9422(01)00443-5. PMID 11830162.

[2] Zi X, Simoneau AR (April 2005). "Flavokawain A, a novel chalcone from kava extract, induces apoptosis in bladder cancer cells by involvement of Bax protein-dependent and mitochondria-dependent apoptotic pathway and suppresses tumor growth in mice" (PDF). Cancer Research. 65 (8): 3479–86. doi:10.1158/0008-5472.CAN-04-3803. PMID 15833884.

[1]

[2]

v t e Chalconoids and their glycosides
Chalconoids	Butein Isoliquiritigenin Methyl hydroxychalcone Okanin
Chalconoid glycosides	Carthamin Marein okanin 3,4,3′-trimethyl ether 4′-glucoside okanin 4-methyl ether 4′-glucoside okanin 4-methyl ether 4′-glucoside monoacetate Okanin 3,4-dimethyl ether 4′-glucoside
Acylated chalconoids	Licochalcone A Sophoradin (prenylated) Tephrospinosin (3′,5′-diisopentenyl-2′,4′-dihydroxychalcone) (prenylated) Xanthohumol (prenylated)
O-methylated chalconoids	Cardamomin Flavokawin B Okanin 3,4,3′,4′-tetramethyl ether Pashanone (2',6'-Dihydroxy-3',4'-dimethoxychalcone)
Flavokavains	Flavokavain A Flavokavain B Flavokavain C
Synthetic	Sofalcone

See also

References

External links