Lupiwighteone is an isoflavone found widely in wild plants and has antioxidant, antibacterial and anti-cancer activities. Lupiwighteone induces caspase-dependent and -independent apoptosis in human breast cancer/tumor cells by inhibiting the PI3K/Akt/mTOR pathway.

Physicochemical Properties

Molecular Formula	C20H18O5
Molecular Weight	338.3539
Exact Mass	338.115
CAS #	104691-86-3
PubChem CID	5317480
Appearance	Off-white to light yellow solid powder
Density	1.4±0.1 g/cm3
Boiling Point	583.5±50.0 °C at 760 mmHg
Melting Point	133-135℃
Flash Point	211.8±23.6 °C
Vapour Pressure	0.0±1.7 mmHg at 25°C
Index of Refraction	1.667
LogP	5.05
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	3
Heavy Atom Count	25
Complexity	554
Defined Atom Stereocenter Count	0
InChi Key	YGCCASGFIOIXIN-UHFFFAOYSA-N
InChi Code	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
Chemical Name	5,7-dihydroxy-3-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)chromen-4-one
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage.
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ln Vitro	Lupiwighteone (2-100 μM; 72 hours) demonstrates cytotoxicity against many cell lines, with IC50s of 23.7 μM and 21 μM, respectively, against DU-145 and SGC-7901 cells [2]. In 48 hours, lupiwighteone (20–60 μM) causes cell cycle arrest in DU-145 cells [2]. In 48 hours, lupiwighteone (20–60 μM) causes apoptosis [2]. The expression of cell cycle-related proteins in DU-145 cells is lowered in a dose-dependent manner by lupiwighteone (20–60 μM; 48 hours) [2]. A dose-dependent increase in ROS generation is induced by lupiwighteone (20–60 μM; 48 hours) [2]. Inducing mitochondria-based intrinsic apoptosis in DU-145 cells, lupiwighteone up-regulates cytochrome c and caspase-3, cleaves PARP-1, and down-regulates p-Akt/Akt ratio and VEGF expression [2].
Cell Assay	Cell viability assay[2] Cell Types: DU-145 cells, C4-2 cells, SGC-7901 cells, Hela cells, HUVEC, MCF-7 cells, CNE cells, Vero Tested Concentrations: 2 μM, 5 μM, 25 μM, 50 μM, 100 μM Incubation Duration: 72 hrs (hours) Experimental Results: Inhibitory effect on the survival of various cancer cell lines and HUVEC Cell cycle analysis [2] Cell Types: DU-145 Cell Tested Concentrations: 20 μM, 40 μM, 60 μM Incubation Duration: 48 hour Experimental Results: Induction of cell cycle arrest. Apoptosis analysis[2] Cell Types: DU-145 Cell Tested Concentrations: 20 μM, 40 μM, 60 μM Incubation Duration: 48 hrs (hours) Experimental Results: Induction of apoptosis. Western Blot Analysis [2] Cell Types: DU-145 Cell Tested Concentrations: 20 μM, 40 μM, 60 μM Incubation Duration: 48 hrs (hours) Experimental Results: CDK1, 2, 4, 6, cyclinD1 and cyclinB1 protein expression diminished in a dose-dependent manner.
References	[1]. 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. [2]. Isoflavone lupiwighteone induces cytotoxic, apoptotic, and antiangiogenic activities in DU-145 prostate cancer cells. Anticancer Drugs. 2015 Jul;26(6):599-611. [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.
Additional Infomation	Lupiwighteone is a member of isoflavones. Lupiwighteone has been reported in Cadophora gregata, Glycyrrhiza uralensis, and other organisms with data available.

Solubility Data

Solubility (In Vitro)

DMSO : ~100 mg/mL (~295.55 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (7.39 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.9555 mL	14.7776 mL	29.5552 mL
	5 mM	0.5911 mL	2.9555 mL	5.9110 mL
	10 mM	0.2956 mL	1.4778 mL	2.9555 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.