Bufothionine

Bufothionine is a sulfur-containing compound which is present in the bufotoxins secreted by the parotoid gland of certain toads of the genera Bufo and Chaunus. This specific compound can be found in the skin of certain species of toad such as the Asiatic Toad,[1][2] Chaunus arunco, Chaunus crucifer, Chaunus spinulosus, and Chaunus arenarum.[3]

Bufothionine
Names
Preferred IUPAC name
5,5-Dimethyl-6-(sulfinooxy)-1,3,4,5-tetrahydropyrrolo[4,3,2-de]quinolin-5-ium
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C12H14N2O3S/c1-14(2)6-5-8-7-13-9-3-4-10(17-18(15)16)12(14)11(8)9/h3-4,7,13H,5-6H2,1-2H3/p+1
  • O=S(O)Oc1ccc2c3c1[N+](CCc3c[nH]2)(C)C
Properties
C12H15N2O3S+
Molar mass 267.32 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Research

In ancient times, cinobufacini, which is extracted from the skin and the parotid venom glands of toad of the bufo genus[4] was used to treat symptoms like swelling and pain. In the present time, cinobufacinin injections are used to achieve satisfactory effect on Hepatocellular carcinoma (HCC) in China.[5] Bufothionine is a major active component of cinobufacini. Bufothionine has been shown to suppress growth of cancerous liver cells in vitro . In vivo, bufothionine has also been showing relieved symptoms and anti inflammatory activities in tumor bearing mice.[5] Experiments were conducted in which cultured cancer cells were shown to have an increase in G2-M damage checkpoint, ensuring that growth of the cell will not continue until the damage to the DNA is corrected while also showing a drop in the G0 and G1 activity, which pertains to phase where there is cell growth and RNA production.[6]  

Bufothionine is shown to induce autophagy in hepatocellular carcinomas by inhibiting JAK2/STAT3 pathways, which may present possibilities of anti cancer mechanism in bufothionine through cinobufacini injections.[5] Similarly, bufothionine has also been shown to increase the chances of cell death and decrease cell growth of gastric cancer related cells by inhibiting the PIM3 gene, which, in cancerous cells, increases the resistance of chemotherapeutic treatments.[7] In glioblastoma multiforme (GBM), bufothionine presents anti-tumor activities in the GBM cells lines U87 and U373 by triggering endoplasmic reticulum stress to lead cell death in the U87 and U373 cells.[8]

References
  1. Dai, L. P.; Gao, H. M.; Wang, Z. M.; Wang, W. H. (2007). "Isolation and structure identification of chemical constituents from the skin of Bufo bufo gargarizans". Yao Xue Xue Bao = Acta Pharmaceutica Sinica. 42 (8): 858–861. PMID 17944235.
  2. Dai, L. P.; Wang, Z. M.; Gao, H. M.; Jiang, X.; Ding, G. Z. (2007). "Determination of bufothionine in skin of Bufo bufo gargarizans and Huachansu injection". Zhongguo Zhong Yao Za Zhi = Zhongguo Zhongyao Zazhi = China Journal of Chinese Materia Medica. 32 (3): 224–226. PMID 17432144.
  3. V Deulofeu; Enrique Duprat (February 10, 1944). "The Basic Constituents of the Venom of some South American Toads" (PDF). Journal of Biological Chemistry. American Society for Biochemistry and Molecular Biology. 153 (2): 459–463. doi:10.1016/S0021-9258(18)71987-X.
  4. Wang, Guojun; Liu, Guanghui; Ye, Yanwei; Fu, Yang; Zhang, Xiefu (September 2019). "Bufothionine exerts anti-cancer activities in gastric cancer through Pim3". Life Sciences. 232: 116615. doi:10.1016/j.lfs.2019.116615. PMID 31260686. S2CID 195772507.
  5. Kong, Wei-Song; Shen, Fang-Xue; Xie, Rui-Fang; Zhou, Gui; Feng, Yi-Ming; Zhou, Xin (April 2021). "Bufothionine induces autophagy in H22 hepatoma-bearing mice by inhibiting JAK2/STAT3 pathway, a possible anti-cancer mechanism of cinobufacini". Journal of Ethnopharmacology. 270: 113848. doi:10.1016/j.jep.2021.113848. PMID 33485977. S2CID 231703160.
  6. Xie, Rui-Fang; Li, Zhi-Cheng; Gao, Bo; Shi, Zhi-Na; Zhou, Xin (2012-06-01). "Bufothionine, a possible effective component in cinobufocini injection for hepatocellular carcinoma". Journal of Ethnopharmacology. Modernization of Traditional Chinese Medicine. 141 (2): 692–700. doi:10.1016/j.jep.2011.12.018. ISSN 0378-8741. PMID 22210051.
  7. Wang, Guojun; Liu, Guanghui; Ye, Yanwei; Fu, Yang; Zhang, Xiefu (2019-09-01). "Bufothionine exerts anti-cancer activities in gastric cancer through Pim3". Life Sciences. 232: 116615. doi:10.1016/j.lfs.2019.116615. ISSN 0024-3205. PMID 31260686. S2CID 195772507.
  8. Sun, Yafeng; Zhang, Xianhong (November 2019). "Bufothionine Promotes Apoptosis via Triggering ER Stress and Synergizes with Temozolomide in Glioblastoma Multiforme Cells". The Anatomical Record. 302 (11): 1950–1957. doi:10.1002/ar.24194. ISSN 1932-8486. PMID 31177611. S2CID 182949594.
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