Chelerythrine

Chelerythrine

Names
IUPAC name 1,2-Dimethoxy-12-methyl[1,3]benzodioxolo[5,6-c]phenanthridin-12-ium
Identifiers
CAS Number	34316-15-9
3D model (Jmol)	Interactive image
ChEBI	CHEBI:78373
ChEMBL	ChEMBL258893
ChemSpider	2602
ECHA InfoCard	100.047.194
IUPHAR/BPS	5953
PubChem	2703
UNII	E3B045W6X0
InChI 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 Key: LLEJIEBFSOEYIV-UHFFFAOYSA-N 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
SMILES O1c3c(OC1)cc2ccc4c5c(c[n+](c4c2c3)C)c(OC)c(OC)cc5
Properties
Chemical formula	C21H18NO4
Molar mass	348.38 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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] It is also found in the plants Zanthoxylum clava-herculis and Zanthoxylum rhoifolium, exhibiting antibacterial activity against Staphylococcus aureus and other human pathogens.^[3][4]

References

1. Chelerythrine 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. 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.
4. 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. doi:10.1371/journal.pone.0097000. PMC 4019524. PMID 24824737.