Chelerythrine

Chelerythrine
Skeletal formula of chelerythrine
Ball-and-stick model of the chelerythrine molecule
Names
Preferred IUPAC name
1,2-Dimethoxy-12-methyl-9H-[1,3]benzodioxolo[5,6-c]phenanthridin-12-ium
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.047.194 Edit this at Wikidata
EC Number
  • 251-930-0
  • chloride: 223-444-9
KEGG
UNII
  • InChI=1S/C21H18NO4/c1-22-10-16-13(6-7-17(23-2)21(16)24-3)14-5-4-12-8-18-19(26-11-25-18)9-15(12)20(14)22/h4-10H,11H2,1-3H3/q+1 checkY
    Key: LLEJIEBFSOEYIV-UHFFFAOYSA-N checkY
  • InChI=1/C21H18NO4/c1-22-10-16-13(6-7-17(23-2)21(16)24-3)14-5-4-12-8-18-19(26-11-25-18)9-15(12)20(14)22/h4-10H,11H2,1-3H3/q+1
    Key: LLEJIEBFSOEYIV-UHFFFAOYAP
  • chloride: InChI=1S/C21H18NO4.ClH/c1-22-10-16-13(6-7-17(23-2)21(16)24-3)14-5-4-12-8-18-19(26-11-25-18)9-15(12)20(14)22;/h4-10H,11H2,1-3H3;1H/q+1;/p-1
    Key: WEEFNMFMNMASJY-UHFFFAOYSA-M
  • O1c3c(OC1)cc2ccc4c5c(c[n+](c4c2c3)C)c(OC)c(OC)cc5
  • chloride: C[n+]1cc2c(ccc(c2OC)OC)c3c1c4cc5c(cc4cc3)OCO5.[Cl-]
Properties
C21H18NO4
Molar mass 348.378 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Chelerythrine is a benzophenanthridine alkaloid present in the plant Chelidonium majus (greater celandine). It is a potent, selective, and cell-permeable protein kinase C inhibitor in vitro.[1] And an efficacious antagonist of G-protein-coupled CB1 receptors.[2] This molecule also exhibits anticancer qualities and it has served as a base for many potential novel drugs against cancer. Structurally, this molecule has two distinct conformations, one being a positively charged iminium form, and the other being an uncharged form, a pseudo-base.[3]

It is also found in the plants Zanthoxylum clava-herculis and Zanthoxylum rhoifolium, exhibiting antibacterial activity against Staphylococcus aureus and other human pathogens.[4][5]

  1. ^ Chelerythrine Chloride from Fermentek
  2. ^ Dhopeshwarkar, Amey S.; Jain, Saurabh; Liao, Chengyong; Ghose, Sudip K.; Bisset, Kathleen M.; Nicholson, Russell A. (2011-03-01). "The actions of benzophenanthridine alkaloids, piperonyl butoxide and (S)-methoprene at the G-protein coupled cannabinoid CB₁ receptor in vitro". European Journal of Pharmacology. 654 (1): 26–32. doi:10.1016/j.ejphar.2010.11.033. ISSN 1879-0712. PMID 21172340.
  3. ^ Dostál, Jiří; Táborská, Eva; Slavík, Jiří; Potáček, Milan; de Hoffmann, Edmond (May 1995). "Structure of Chelerythrine Base". Journal of Natural Products. 58 (5): 723–729. doi:10.1021/np50119a010. ISSN 0163-3864.
  4. ^ Gibbons, Simon; Leimkugel, Julia; Oluwatuyi, Moyo; et al. (2003). "<Activity of Zanthoxylum clava-herculis extracts against multi-drug resistant methicillin-resistant Staphylococcus aureus (mdr-MRSA)>". Phytotherapy Research. 17 (3): 274–275. doi:10.1002/ptr.1112. PMID 12672160. S2CID 32722743.
  5. ^ Tavares, Luciana de C; Zanon, Graciane; Weber, Andréia D.; et al. (2014). "<Structure-activity relationship of benzophenanthridine alkaloids from Zanthoxylum rhoifolium having antimicrobial activity>". PLOS ONE. 9 (5): e97000. Bibcode:2014PLoSO...997000T. doi:10.1371/journal.pone.0097000. PMC 4019524. PMID 24824737.