Resibufogenin (also known as Bufogenin; Recibufogenin; RBG), a component of huachansu, is a natural product with the potential for the treatment of pancreatic cancer. It has been shown to exhibit the anti-proliferative effect against cancer cells, and this may be attributed to the degradation of cyclin D1 caused by the activation of GSK-3β.

Physicochemical Properties

Molecular Formula	C24H32O4
Molecular Weight	384.5085
Exact Mass	384.23
CAS #	465-39-4
PubChem CID	6917974
Appearance	White to off-white solid powder
Density	1.3±0.1 g/cm3
Boiling Point	554.9±50.0 °C at 760 mmHg
Melting Point	155ºC
Flash Point	190.7±23.6 °C
Vapour Pressure	0.0±3.4 mmHg at 25°C
Index of Refraction	1.603
LogP	2.89
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	1
Heavy Atom Count	28
Complexity	786
Defined Atom Stereocenter Count	9
SMILES	O1[C@]2([H])C([H])([H])[C@]([H])(C3=C([H])OC(C([H])=C3[H])=O)[C@@]3(C([H])([H])[H])C([H])([H])C([H])([H])[C@]4([H])[C@@]5(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]([H])(C([H])([H])[C@@]5([H])C([H])([H])C([H])([H])[C@@]4([H])[C@]132)O[H]
InChi Key	ATLJNLYIJOCWJE-CWMZOUAVSA-N
InChi Code	InChI=1S/C24H32O4/c1-22-9-7-16(25)11-15(22)4-5-18-17(22)8-10-23(2)19(12-20-24(18,23)28-20)14-3-6-21(26)27-13-14/h3,6,13,15-20,25H,4-5,7-12H2,1-2H3/t15-,16+,17+,18-,19-,20-,22+,23-,24-/m1/s1
Chemical Name	5-[(1R,2S,4R,6R,7R,10S,11S,14S,16R)-14-hydroxy-7,11-dimethyl-3-oxapentacyclo[8.8.0.02,4.02,7.011,16]octadecan-6-yl]pyran-2-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
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

References

:J Asian Nat Prod Res. 2011 Sep;13(9):831-7.;Nat Prod Commun. 2011 Nov;6(11):1581-4.

Additional Infomation

Bufogenin is a steroid lactone of Chan su (toad venom), a Chinese medicine obtained from the skin venom gland of toads. A specific Na/K-ATPase protein inhibitor, it is used as a cardiotonic and central nervous system (CNS) respiratory agent, an analgesic and anesthetic, and as a remedy for ulcers. It has a role as an EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor. It is a steroid lactone and an epoxy steroid. It is functionally related to a bufanolide. Resibufogenin has been reported in Phrynoidis asper, Bufo gargarizans, and other organisms with data available. Bufogenin is a bufadienolide toxin originally isolated from the venom of the Chinese toad Bufo gargarizans; it is also one of the glycosides in the traditional Chinese medicine ChanSu, with potential cardiotonic activity. Although the mechanism of action of bufogenin is still under investigation, this agent is a specific Na+/K+-ATPase inhibitor and has been shown to reduce blood pressure in a rat model of preeclampsia.

Solubility Data

Solubility (In Vitro)

DMSO : ~100 mg/mL (~260.07 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.75 mg/mL (7.15 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (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 27.5 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.75 mg/mL (7.15 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (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 27.5 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.75 mg/mL (7.15 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 27.5 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	2.6007 mL	13.0036 mL	26.0071 mL
	5 mM	0.5201 mL	2.6007 mL	5.2014 mL
	10 mM	0.2601 mL	1.3004 mL	2.6007 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.