Flavokavain B

Last updated
Flavokavain B
Flavokavain B.svg
Names
Preferred IUPAC name
2′-Hydroxy-4′,6′-dimethoxychalcone
Other names
Flavokawain B
Identifiers
3D model (JSmol)
2059845
ChEBI
ChEMBL
ChemSpider
PubChem CID
UNII
  • 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
  • O=C(C2=C(O)C=C(OC)C=C2OC)/C=C/C1=CC=CC=C1
Properties
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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Flavokavain B is a flavokavain found in the kava plant. [1]

Contents

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]

See also

References

  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


This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.