Voacristine

Voacristine is a indole alkaloid occurring in Voacanga and Tabernaemontana genus. It is also an iboga type alkaloid.[1]

Voacristine
Clinical data
Other names19(S)-Heyneanine
Identifiers
  • methyl (1S,15R,17S,18S)-17-[(1S)-1-hydroxyethyl]-7-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
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC22H28N2O4
Molar mass384.476 g·mol−1
3D model (JSmol)
  • C[C@@H]([C@H]1C[C@@H]2C[C@@]3([C@H]1N(C2)CCC4=C3NC5=C4C=C(C=C5)OC)C(=O)OC)O
  • 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

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.[2]

Sources

Voacristine is found in multiple species of Tabernaemontana some of which are Tabernaemontana divaricata,[3] Tabernaemontana heyneana,[4] Tabernaemontana ventricosa[5] and in Voacanga africana.[6]

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). "[Voacanga alkaloids. III. Voacristine: identity with voacangarine and decomposition to iboxygaine and ibogaine]". 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.
  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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