:Flavokavain A

{{Chembox

| Watchedfields = changed

| verifiedrevid = 455169884

| ImageFile = Flavokavain A.svg

| ImageSize = 200px

| PIN = 2′-Hydroxy-4,4′,6′-trimethoxychalcone

| OtherNames = Flavokawain A

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 37951-13-6

| Beilstein = 2224776

| ChEBI = 157725

| ChEMBL = 243829

| ChemSpiderID = 4511445

| EC_number = 636-475-1

| UNII_Ref = {{fdacite|correct|FDA}}

| PubChem = 5355469

| UNII = 8OM2XZ2ZM3

| StdInChI=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+

| StdInChIKey = CGIBCVBDFUTMPT-RMKNXTFCSA-N

| SMILES = O=C(C2=C(O)C=C(OC)C=C2OC)/C=C/C1=CC=C(OC)C=C1

}}

|Section2={{Chembox Properties

| C=18 | H=18 | O=5

| Appearance =

| Density =

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|Section3={{Chembox Hazards

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Flavokavain A is a flavokavain found in the kava plant.{{cite journal|title=Kavalactones from Piper methysticum, and their 13C NMR spectroscopic analyses|journal=Phytochemistry|date=February 2002|first=H. Ranjith W.|last=Dharmaratne|author2=N. P. Dhammika Nanayakkara |author3=Ikhlas A. Khan |volume=59|issue=4|pages=429–33|pmid=11830162 |doi=10.1016/S0031-9422(01)00443-5 |bibcode=2002PChem..59..429R }}

A systematic review of studies on kava found evidence that its bioactive compounds, particularly flavokavain A and 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.{{cite journal |last1=Celentano |first1=Antonio |last2=Tran |first2=Andrew |last3=Testa |first3=Claire |last4=Thayanantha |first4=Krishen |last5=Tan-Orders |first5=William |last6=Tan |first6=Stephanie |last7=Syamal |first7=Mitali |last8=McCullough |first8=Michael J. |last9=Yap |first9=Tami |year=2019 |title=The protective effects of Kava (Piper methysticum) constituents in cancers: A systematic review |journal=Journal of Oral Pathology & Medicine |volume=48 |issue=7 |pages=510–529 |doi=10.1111/jop.12900 |pmid=31172600}} It shows strong anticancer effects—particularly against bladder cancer—by inducing apoptosis through Bax-dependent pathways and inhibiting key anti-apoptotic proteins, with promising results in both cell cultures and animal models.{{cite journal|title=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.|vauthors=Zi X, Simoneau AR |journal=Cancer Research|pmid=15833884|doi=10.1158/0008-5472.CAN-04-3803|volume=65|issue=8|date=April 2005|pages=3479–86|doi-access=free|url=https://aacr.figshare.com/articles/journal_contribution/Supplementary_Figure_S1_from_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/22365111/1/files/39809379.pdf}}

Kava alone is not hepatotoxic in mice, but its chalcone compounds flavokavains A and B significantly increase acetaminophen-induced liver toxicity, suggesting that herb-drug interactions may explain rare severe liver damage seen with kava use in humans.{{cite journal |last1=Narayanapillai |first1=Sreekanth C |last2=Leitzman |first2=Pablo |last3=O'Sullivan |first3=M Gerard |last4=Xing |first4=Chengguo |title=Flavokawains A and B in Kava, Not Dihydromethysticin, Potentiate Acetaminophen-Induced Hepatotoxicity in C57BL/6 Mice |journal=Chemical Research in Toxicology |date=Sep 3, 2014 |volume=27 |issue=10 |pages=1871–1876 |doi=10.1021/tx5003194 |pmid=25185080 |pmc=4203398 }}