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Chemical compound
Voacristine
Other names 19(S)-Heyneanine
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 )
Formula C 22 H 28 N 2 O 4
Molar mass 384.476 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
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]
See also
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 .