Name | bufogenin |
Synonyms | rbg bufogenin BUFOGENIN bufogenina RESIBUFOGENIN 3-hydroxy-14,15-epoxybufa-20,22-dienolide 20,22,5BETA-BUFADIENOLID-14BETA,15BETA-EPOXY-3BETA-OL 5-beta-Bufa-20,22-dienolide, 14,15-beta-epoxy-3-beta-hydroxy- (3beta,5beta,15beta)-3-hydroxy-14,15-epoxybufa-20,22-dienolide (3BETA,5BETA,15BETA)-14,15EPOXY-3-HYDROXY-5-BUFA-20,22-DIENOLIDE (3beta,5beta,8xi,9xi,15beta)-3-hydroxy-14,15-epoxybufa-20,22-dienolide |
CAS | 465-39-4 |
InChI | InChI=1/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 |
Molecular Formula | C24H32O4 |
Molar Mass | 384.51 |
Density | 1.0474 (rough estimate) |
Melting Point | 113-140°/155-168° |
Boling Point | 431.17°C (rough estimate) |
Specific Rotation(α) | D22 -7.1° (c = 1.259 in chloroform); D16 -5.4° (c = 2.030 in chloroform) |
Flash Point | 190.7°C |
Solubility | Soluble in chloroform, methanol, DMSO and other organic solvents, insoluble in water. |
Vapor Presure | 1.26E-14mmHg at 25°C |
Appearance | White crystal |
pKa | 15.14±0.70(Predicted) |
Storage Condition | under inert gas (nitrogen or Argon) at 2-8°C |
Refractive Index | 1.4860 (estimate) |
MDL | MFCD00210361 |
Safety Description | 24/25 - Avoid contact with skin and eyes. |
UN IDs | 3172 |
HS Code | 29322090 |
Hazard Class | 6.1(a) |
Packing Group | II |
Toxicity | LD50 oral in mouse: 59800mg/kg |
Reference Show more | 1. Li Zhidong, Zhu Shichun, GE Zhaohui. HPLC Determination of different batches of Shexiang Baoxin pills Chinese toad venom base and xenopan venom ligand content [J]. Strait pharmacy 2017 029(012):72-74. 2. Sun Aiping, Sun Ping, Li Na. Study on extraction and purification process of Xenopus venom ligands from venenum bufonis [J]. Chinese herbal medicine, 2019, 50(03):74-80. 3. Cao Yueting, Cui, cocoa, Wu, Jiheng, et al. Study on the correlation of the components of the venom of Chinese big toad [J]. Chinese Journal of Traditional Chinese Medicine 2019(9). 4. Zhang Mei-Tuo et al. [IF = 2.193]. "Strategic Combination of Isocratic and Gradient Elution for Simultaneous Separation of Polar compositions in Traditional Chinese Medicines by HPLC." J Anal Methods Chem. 2018;2018:7569283 5. [IF = 4.411] Yueting Cao et al."Chemical Profile and Multicomponent Quantitative Analysis for the Quality Evaluation of Toad Venom from Different Origins."Molecules. 2019 Jan;24(19):3595 6. [IF=4.379] Cao Yueting et al."The impact of multiple climatic and geographic factors on the chemical defences of Asian toads (Bufo gargarizans Cantor)."Sci Rep-Uk. 2019 Nov;9(1):1-11 7. [IF=1.902] Ke-ke Cui et al."Quantitative analysis of multicomponents by a single marker and quality evaluation of Venenum Bufonis from different geographical origins."Biomed Chromatogr. 2019 Sep;33(9):e4555 |
application | the main pharmacological effect of ester bufenotoxin is anti-tumor. Using modern chromatographic technology to separate cinobufagin injection, ester toad poison ligand components were obtained, and the main monomers of ester toad poison ligand compounds were analyzed and identified by HPLC-DAD-FT-ICR-MS. Through in vitro cell screening of the anti-tumor activity of the ester bufad toxin ligand, a nude mouse model of pancreatic cancer was established in vivo to evaluate the efficacy of the ester bufad toxin ligand, and the main active monomer of the ester bufad toxin ligand was isolated in vitro for anti-pancreatic cancer activity screening. The results showed that the half inhibitory concentrations of the ester bufagin in cinobufagin injection on liver cancer BEL7402 cells, gastric cancer BGC823 cells and pancreatic cancer SW1990,MIA Pa Ca-2 cells were 0.47±0.03,0.06±0.01,0.06±0.02,0.11±0.03g/L respectively, and the half lethal dose of ester bufagin was 20 mg/kg. The therapeutic effect of SW1990 tumor-bearing nude mice in vivo was close to that of chemotherapy drug gemcitabine, in vitro anti-pancreatic cancer activity of 12 active substances isolated and identified from the ester bufadotoxin ligand was screened out that the activity of the day bufadotoxin, sand bufadotoxin and hellebore aglycone had obvious inhibitory effects on SW1990 and BxPC-3 cells. Therefore, the inhibition rate of ester bufogene on pancreatic cancer cells in vitro is almost the same as that of gastric cancer, and it has a significant therapeutic effect on pancreatic cancer-bearing nude mice in vivo. At the same time, the monomer components of ester bufogene in the ester bufogene have obvious inhibitory effects on pancreatic cancer cells in vitro. |
pharmacokinetics | 2, 5, 10, 15, 20, 30, 45, 60, 90 min after giving toad venom extract 0.8 mg/kg to rat tail iv, blood was taken from orbit, and plasma samples were pretreated by combining acetonitrile precipitated protein with liquid-liquid extraction, HPLC method was used to determine the mass concentrations of bufalin, bufensu and bufenotoxin in rat plasma, and the pharmacokinetic parameters were fitted by Kinetica software. The results showed that Bufalin, Bufalin venom and Ester toad venom ligand were well separated, with good reproducibility, precision and linearity, which met the requirements of in vivo analysis. After non-atrioventricular model fitting, the main pharmacokinetic parameters of Bufalin, Ester toad venom and Ester toad venom ligand in rats were obtained. iv When administered for 30 min, the blood drug concentration decreased to less than 1/5 of Cmax. Toad steroids are metabolized rapidly in rats. |
overview | as one of the effective components of toad venom, it is speculated that the natural Chinese medicine monomer molecule ester toad venom can induce osteosarcoma cells Apoptosis, thereby inhibiting the proliferation of tumor cells. MTT assay was used to detect the proliferation of osteosarcoma cells treated with different concentrations of ester bufad toxin ligand. MTT test results showed that ester bufad toxin ligand could effectively inhibit the proliferation of osteosarcoma cells in vitro, and its effect on tumor proliferation was dose-dependent. In addition, the Western Blotting results show that ester bufadine can up-regulate the expression of P53 protein in osteosarcoma cells, which suggests that ester bufadine may inhibit the growth of tumor cells by triggering apoptosis of osteosarcoma cells. |
biological activity | Resibufogenin (Bufogenin, Recibufogenin) is an anticancer component of huachansu cinobufagin, which triggers necrosis by up-regulating the receptor-interacting protein kinase 3 (RIP3) and phosphorylated mixed lineage kinase domain-like protein Ser358 site to trigger necrosis. Resibufogenin can exert cytotoxic effect by inducing reactive oxygen species (ROS) accumulation. Resibufogenin can induce apoptosis and caspase-3 and caspase-8 activities. Resibufogenin increased the expression of Bax/Bcl-2 and inhibited the protein expression of cyclin D1, cyclin E, PI3K, p-AKT, p-GSK3β and β-catenin. |
Target | Value |
use | used for content determination/identification/pharmacological experiments, etc. |
category | toxic substances |
toxicity classification | highly toxic |
acute toxicity | oral administration-mouse LD50: 6.4 mg/kg; Abdominal cavity-mouse LD50: 16.3 mg/kg |
flammability hazard characteristics | thermal decomposition discharges toxic, spicy and irritating smoke |
storage and transportation characteristics | warehouse ventilation and low temperature drying; Separate from food raw materials |
fire extinguishing agent | water, dry powder, dry sand, carbon dioxide, foam, 1211 fire extinguishing agent |