Voacristine

Voacristine
Clinical data
Other names	19(S)-Heyneanine
Identifiers
	IUPAC name 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	545-84-6;
PubChem CID	196982;
ChemSpider	170602;
ChEMBL	ChEMBL463317;
CompTox Dashboard (EPA)	DTXSID40969687 ;
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=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.^[1]

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 including Tabernaemontana divaricata,^[3] Tabernaemontana heyneana,^[4] Tabernaemontana ventricosa,^[5] and Voacanga africana.^[6]

References

^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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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[pmid21042867-1] 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.

[pmid14437366-2] 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.

[pmid8778503-3] 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.

[pmid11509989-4] 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.

[pmid33459049-5] 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.

[pmid26140390-6] 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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Voacristine

Contents

Chemistry

Sources

See also

References