Isovoacristine

Isovoacristine
Identifiers
	IUPAC name methyl (1S,15S,17S,18S)-17-[(1S)-1-hydroxyethyl]-6-methoxy-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4(9),5,7-tetraene-1-carboxylate;
CAS Number	438201-17-3;
PubChem CID	12304498;
ChemSpider	23249593;
ChEMBL	ChEMBL360973;
Chemical and physical data
Formula	C22H28N2O4
Molar mass	384.476 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@@H]([C@H]1C[C@H]2C[C@@]3([C@H]1N(C2)CCC4=C3NC5=C4C=CC(=C5)OC)C(=O)OC)O;
	InChI InChI=1S/C22H28N2O4/c1-12(25)17-8-13-10-22(21(26)28-3)19-16(6-7-24(11-13)20(17)22)15-5-4-14(27-2)9-18(15)23-19/h4-5,9,12-13,17,20,23,25H,6-8,10-11H2,1-3H3/t12-,13-,17+,20-,22+/m0/s1; Key:XGWIRMWTCWJZPG-ZHBRIVESSA-N;

Isovoacristine is an ibogan-type indole alkaloid, primarily isolated from plants of the Tabernaemontana genus such as Tabernaemontana calcarea,^[1] Tabernaemontana divaricata,^[2] and Tabernaemontana laurifolia.^[3] It has anticholinergic and antihistaminic properties.^[4] It also has demonstrated cytotoxic effects against the A2780 ovarian cancer cell line.^[5]

References

^ Prakash Chaturvedula VS, Sprague S, Schilling JK, Kingston DG (April 2003). "New cytotoxic indole alkaloids from Tabernaemontana calcarea from the Madagascar rainforest". Journal of Natural Products. 66 (4): 528–31. Bibcode:2003JNAtP..66..528P. doi:10.1021/np020548e. PMID 12713407.
^ Arambewela LS, Ranatunge T (January 1991). "Indole alkaloids from Tabernaemontana divaricata". Phytochemistry. 30 (5): 1740–1741. Bibcode:1991PChem..30.1740A. doi:10.1016/0031-9422(91)84254-P.
^ Cava MP, Mowdood SK, Beal JL (1965). "Isovoacristine: a new iboga-type alkaloid from Tabernaemontana laurifolia". Chemistry & Industry. 51. London, United Kingdom: 2064.
^ Singh A, ed. (2011). Herbalism, Phytochemistry and Ethnopharmacology. p. 45. doi:10.1201/b10878. ISBN 978-1-4398-5361-0.
^ Oliveros-Díaz A, Olivero-Verbel J, Pájaro-González Y, Díaz-Castillo F (June 2021). "Molecular Human Targets of Bioactive Alkaloid-Type Compounds from Tabernaemontana cymose Jacq". Molecules. 26 (12). Basel, Switzerland: 3765. doi:10.3390/molecules26123765. PMC 8234993. PMID 34205626.