Catharanthine

Catharanthine
Names
IUPAC name
Methyl 3,4-didehydroibogamine-18-carboxylate
Systematic IUPAC name
Methyl (6R,6aR,9S)-7-ethyl-9,10,12,13-tetrahydro-5H-6,9-methanopyrido[1′,2′:1,2]azepino[4,5-b]indole-6(6aH)-carboxylate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.017.806 Edit this at Wikidata
UNII
  • InChI=1S/C21H24N2O2/c1-3-14-10-13-11-21(20(24)25-2)18-16(8-9-23(12-13)19(14)21)15-6-4-5-7-17(15)22-18/h4-7,10,13,19,22H,3,8-9,11-12H2,1-2H3/t13-,19+,21-/m0/s1
    Key: CMKFQVZJOWHHDV-NQZBTDCJSA-N
  • InChI=1/C21H24N2O2/c1-3-14-10-13-11-21(20(24)25-2)18-16(8-9-23(12-13)19(14)21)15-6-4-5-7-17(15)22-18/h4-7,10,13,19,22H,3,8-9,11-12H2,1-2H3/t13-,19+,21-/m0/s1
    Key: CMKFQVZJOWHHDV-NQZBTDCJBW
  • CCC1=C[C@H]2C[C@]3([C@@H]1N(C2)CCc4c3[nH]c5c4cccc5)C(=O)OC
Properties
C21H24N2O2
Molar mass 336.435 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Catharanthine is a terpene indole alkaloid produced by the medicinal plant Catharanthus roseus and Tabernaemontana divaricata. Catharanthine is derived from strictosidine, but the exact mechanism by which this happens is currently unknown. Catharanthine is one of the two precursors that form vinblastine, the other being vindoline.

Pharmacology

(+)-Catharanthine competitively inhibits α9α10 nAChRs with potencies higher than that at α3β4 and α4β2 nAChRs and directly blocks CaV2.2.[1] Catharanthine alkaloids are non competitive antagonist of muscle type nAChRs and this is thought to be the case due to presence of catharanthine moiety in those compounds.[2] In in vitro study, it increased the levels of cAMP by inhibiting cAMP phosphodiesterase in brain.[3] It is a potent inhibitor of TRPM8, similar to BCTC.[4] Structural analysis of catharanthine shows activity on TRPM8, TRPA1, and butyrylcholinesterase.[5]

See also

References

  1. ^ Arias HR, Tae HS, Micheli L, Yousuf A, Ghelardini C, Adams DJ, Di Cesare Mannelli L (September 2020). "Coronaridine congeners decrease neuropathic pain in mice and inhibit α9α10 nicotinic acetylcholine receptors and CaV2.2 channels". Neuropharmacology. 175: 108194. doi:10.1016/j.neuropharm.2020.108194. hdl:2158/1213504. PMID 32540451. S2CID 219705597.
  2. ^ Arias HR, Feuerbach D, Targowska-Duda KM, Jozwiak K (September 2010). "Catharanthine alkaloids are noncompetitive antagonists of muscle-type nicotinic acetylcholine receptors". Neurochemistry International. 57 (2): 153–61. doi:10.1016/j.neuint.2010.05.007. PMID 20493225. S2CID 24594292.
  3. ^ "Ethnobotany and ethnopharmacology of Tabernaemontana divaricata".
  4. ^ Terada Y, Kitajima M, Taguchi F, Takayama H, Horie S, Watanabe T (August 2014). "Identification of Indole Alkaloid Structural Units Important for Stimulus-Selective TRPM8 Inhibition: SAR Study of Naturally Occurring Iboga Derivatives". Journal of Natural Products. 77 (8): 1831–8. doi:10.1021/np500235b. PMID 25052206.
  5. ^ "Catharanthine". SwissTargetPrediction.
  • Jadhav, A.; Liang, W.; Papageorgiou, P. C.; Shoker, A.; Kanthan, S. C.; Balsevich, J.; Levy, A. S.; Heximer, S.; Backx, P. H.; Gopalakrishnan, V. (2013). "Catharanthine dilates small mesenteric arteries and decreases heart rate and cardiac contractility by inhibition of voltage-operated calcium channels on vascular smooth muscle cells and cardiomyocytes". The Journal of Pharmacology and Experimental Therapeutics. 345 (3): 383–392. doi:10.1124/jpet.112.199661. PMID 23532933. S2CID 206501362.

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