Flavokavain B

Flavokavain B
Names
	Preferred IUPAC name 2′-Hydroxy-4′,6′-dimethoxychalcone
	Other names Flavokawain B
Identifiers
CAS Number	1775-97-9 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	2059845
ChEBI	CHEBI:65899;
ChEMBL	ChEMBL104255;
ChemSpider	4511912;
PubChem CID	5356121;
UNII	R9WC6SM4UQ ;
CompTox Dashboard (EPA)	DTXSID601028794 ;
	InChI InChI=1S/C17H16O4/c1-20-13-10-15(19)17(16(11-13)21-2)14(18)9-8-12-6-4-3-5-7-12/h3-11,19H,1-2H3/b9-8+ Key: QKQLSQLKXBHUSO-CMDGGOBGSA-N;
	SMILES O=C(C2=C(O)C=C(OC)C=C2OC)/C=C/C1=CC=CC=C1;
Properties
Chemical formula	C17H16O4
Molar mass	284.311 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 B is a flavokavain found in the kava plant.^[1]

A systematic review of studies on kava found evidence that its bioactive compounds, particularly flavokavain B, exert antiproliferative and pro-apoptotic effects across multiple cancer models, highlighting its potential chemotherapeutic use especially for epithelial cancers, though research on oral squamous cell carcinoma remains scarce.^[2]

It is a potent liver toxin that causes cell death by inducing oxidative stress and disrupting key cellular signaling pathways, but its harmful effects can be reversed by glutathione supplementation.^[3] Studies show that flavokavain B is present at much higher levels in “Two-Day” kava cultivars like Palisi compared to noble varieties, but current evidence does not conclusively prove it is responsible for kava-related liver toxicity in humans.^[4]

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.
^ Celentano, Antonio; Tran, Andrew; Testa, Claire; Thayanantha, Krishen; Tan-Orders, William; Tan, Stephanie; Syamal, Mitali; McCullough, Michael J.; Yap, Tami (2019). "The protective effects of Kava (Piper methysticum) constituents in cancers: A systematic review". Journal of Oral Pathology & Medicine. 48 (7): 510–529. doi:10.1111/jop.12900. PMID 31172600.
^ Zhou P., Gross S., Liu J.-H., Yu B.-Y., Feng L.-L., Nolta J., Sharma V., Piwnica-Worms D., Qiu S.X 'Flavokawain B, the hepatotoxic constituent from kava root, induces GSH-sensitive oxidative stress through modulation of IKK/NF-κB and MAPK signaling pathways . FASEB Journal 2010 24:12 (4722-4732)
^ Teschke, R., Qiu, S. X., & Lebot, V. (2011). Herbal hepatotoxicity by kava: Update on pipermethystine, flavokavain B, and mould hepatotoxins as primarily assumed culprits. Digestive and Liver Disease, 43(9), 676–681. https://www.dldjournalonline.com/article/S1590-8658(11)00048-X/fulltext

External links

Flavokawain B 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] Celentano, Antonio; Tran, Andrew; Testa, Claire; Thayanantha, Krishen; Tan-Orders, William; Tan, Stephanie; Syamal, Mitali; McCullough, Michael J.; Yap, Tami (2019). "The protective effects of Kava (Piper methysticum) constituents in cancers: A systematic review". Journal of Oral Pathology & Medicine. 48 (7): 510–529. doi:10.1111/jop.12900. PMID 31172600.

[3] Zhou P., Gross S., Liu J.-H., Yu B.-Y., Feng L.-L., Nolta J., Sharma V., Piwnica-Worms D., Qiu S.X 'Flavokawain B, the hepatotoxic constituent from kava root, induces GSH-sensitive oxidative stress through modulation of IKK/NF-κB and MAPK signaling pathways . FASEB Journal 2010 24:12 (4722-4732)

[4] Teschke, R., Qiu, S. X., & Lebot, V. (2011). Herbal hepatotoxicity by kava: Update on pipermethystine, flavokavain B, and mould hepatotoxins as primarily assumed culprits. Digestive and Liver Disease, 43(9), 676–681. https://www.dldjournalonline.com/article/S1590-8658(11)00048-X/fulltext

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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

Flavokavain B

Flavokavain B

Flavokavain B

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Flavokavain B

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