Lupiwighteone

• CAT Number: M135845
• CAS Number: 104691-86-3
• Molecular Formula: C20H18O5
• Molecular Weight: 338.35
• Purity: ≥95%
• Synonyms: 5,7-dihydroxy-3-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)chromen-4-one
• InChI: InChI=1S/C20H18O5/c1-11(2)3-8-14-16(22)9-17(23)18-19(24)15(10-25-20(14)18)12-4-6-13(21)7-5-12/h3-7,9-10,21-23H,8H2,1-2H3
• InChIKey: YGCCASGFIOIXIN-UHFFFAOYSA-N
• SMILES: CC(=CCC1=C2C(=C(C=C1O)O)C(=O)C(=CO2)C3=CC=C(C=C3)O)C

Lupiwighteone is an isoflavone present widely in wild-growing plants, with antioxidant, antimicrobial and anticancer effects. Lupiwighteone induces caspase-dependent and -independent apoptosis on human breast cancer cells via inhibiting PI3K/Akt/mTOR pathway[1][2].
Lupiwighteone (2-100 μM; 72 hours) shows cytotoxicity towards various cell lines, especially on DU-145 cells and SGC-7901 cells with IC50s of 23.7 μM and 21 μM, respectively[2].
Lupiwighteone (20-60 μM; 48 hours) induces (cell cycle arrest in DU-145 cells[2].
Lupiwighteone (20-60 μM; 48 hours) induces cells apoptosis[2].
Lupiwighteone (20-60 μM; 48 hours) decreases the cell cycle-related protein expressions in a dose-dependent manner in DU-145 cells[2].
Lupiwighteone (20-60 μM; 48 hours) induces a dose-dependent increase in ROS production[2].
Lupiwighteone up-regulates of cytochrome c and caspase-3, and subsequent cleavage of PARP-1 and down-regulates of the p-Akt/Akt ratio and VEGF expression, suggests the activation of mitochondria-based intrinsic apoptosis in DU-145 cells[2].

Reference

[1]. Won YS, et al. Lupiwighteone induces caspase-dependent and -independent apoptosis on human breast cancer cells via inhibiting PI3K/Akt/mTOR pathway. Food Chem Toxicol. 2020 Jan;135:110863.
 [Content Brief]

[2]. Ren J, et al. Isoflavone lupiwighteone induces cytotoxic, apoptotic, and antiangiogenic activities in DU-145 prostate cancer cells. Anticancer Drugs. 2015 Jul;26(6):599-611.
 [Content Brief]

[3]. Li XL, Sui L, Lin FH, Lian Y, Ai LZ, Zhang Y. Differential effects of genistein and 8-prenylgenistein on reproductive tissues in immature female mice. Pharm Biol. 2019;57(1):226-230.
 [Content Brief]