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Voacristine

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Chemical compound

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Pharmaceutical compound
Voacristine
Clinical data
Other names19(S)-Heyneanine
Identifiers
IUPAC name
  • methyl (1S,15R,17S,18S)-17--7-methoxy-3,13-diazapentacyclononadeca-2(10),4(9),5,7-tetraene-1-carboxylate
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC22H28N2O4
Molar mass384.476 g·mol
3D model (JSmol)
SMILES
  • C(1C2C3(1N(C2)CCC4=C3NC5=C4C=C(C=C5)OC)C(=O)OC)O
InChI
  • InChI=1S/C22H28N2O4/c1-12(25)16-8-13-10-22(21(26)28-3)19-15(6-7-24(11-13)20(16)22)17-9-14(27-2)4-5-18(17)23-19/h4-5,9,12-13,16,20,23,25H,6-8,10-11H2,1-3H3/t12-,13+,16+,20-,22+/m0/s1
  • Key:OYMQKBZMKFJPMH-VJMPXSKLSA-N

Voacristine is a indole alkaloid occurring in Voacanga and Tabernaemontana genus. It is also an iboga type alkaloid.

Chemistry

Its structure is almost similar to voacangine, an alkaloid used in semi-synthesis of ibogaine. Compared to voacangine, it has an extra O-atom. When it is degraded, iboxygaine and ibogaine are formed.

Sources

Voacristine is found in multiple species of Tabernaemontana including Tabernaemontana divaricata, Tabernaemontana heyneana, Tabernaemontana ventricosa, and Voacanga africana.

See also

References

  1. Lo MW, Matsumoto K, Iwai M, Tashima K, Kitajima M, Horie S, Takayama H (January 2011). "Inhibitory effect of Iboga-type indole alkaloids on capsaicin-induced contraction in isolated mouse rectum". Journal of Natural Medicines. 65 (1): 157–65. doi:10.1007/s11418-010-0478-6. PMID 21042867. S2CID 25706616.
  2. Renner U, Prins DA (December 1959). "". Experientia (in German). 15: 456–7. doi:10.1007/BF02158249. PMID 14437366. S2CID 26926236.
  3. Henriques AT, Melo AA, Moreno PR, Ene LL, Henriques JA, Schapoval EE (January 1996). "Ervatamia coronaria: chemical constituents and some pharmacological activities". Journal of Ethnopharmacology. 50 (1): 19–25. doi:10.1016/0378-8741(95)01328-8. PMID 8778503.
  4. Srivastava S, Singh MM, Kulshreshtha DK (August 2001). "A new alkaloid and other anti-implantation principles from Tabernaemontana heyneana". Planta Medica. 67 (6): 577–9. doi:10.1055/s-2001-16495. PMID 11509989. S2CID 260252763.
  5. Andima M, Ndakala A, Derese S, Biswajyoti S, Hussain A, Yang LJ, Akoth OE, Coghi P, Pal C, Heydenreich M, Wong VK, Yenesew A (January 2021). "Antileishmanial and cytotoxic activity of secondary metabolites from Taberneamontana ventricosa and two aloe species". Natural Product Research. 36 (5): 1365–1369. doi:10.1080/14786419.2021.1871906. PMID 33459049. S2CID 231635212.
  6. Chen HM, Yang YT, Li HX, Cao ZX, Dan XM, Mei L, Guo DL, Song CX, Dai Y, Hu J, Deng Y (2016). "Cytotoxic monoterpenoid indole alkaloids isolated from the barks of Voacanga africana Staph". Natural Product Research. 30 (10): 1144–9. doi:10.1080/14786419.2015.1046132. PMID 26140390. S2CID 23406913.


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