Stemmadenine

Stemmadenine
Names
IUPAC name
Methyl (19E)-17-hydroxy-2,7,19,20-tetradehydro-3,7-seco-15β-curan-16-carboxylate
Systematic IUPAC name
Methyl (5E,6R,7S)-5-ethylidene-7-(hydroxymethyl)-1,4,5,6,7,8-hexahydro-2H-3,6-ethanoazonino[5,4-b]indole-7-carboxylate
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
UNII
  • InChI=1S/C21H26N2O3/c1-3-14-12-23-10-8-16-15-6-4-5-7-18(15)22-19(16)21(13-24,20(25)26-2)17(14)9-11-23/h3-7,17,22,24H,8-13H2,1-2H3/b14-3-/t17-,21+/m1/s1
    Key: MBXJCHZRHROMQA-YVDMJPQFSA-N
  • InChI=1/C21H26N2O3/c1-3-14-12-23-10-8-16-15-6-4-5-7-18(15)22-19(16)21(13-24,20(25)26-2)17(14)9-11-23/h3-7,17,22,24H,8-13H2,1-2H3/b14-3-/t17-,21+/m1/s1
    Key: MBXJCHZRHROMQA-YVDMJPQFBN
  • C/C=C\1/CN2CC[C@H]1[C@](C3=C(CC2)C4=CC=CC=C4N3)(CO)C(=O)OC
Properties
C21H26N2O3
Molar mass 354.450 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Stemmadenine is a terpene indole alkaloid. Stemmadenine is believed to be formed from preakuammicine by a carbon-carbon bond cleavage. Cleavage of a second carbon-carbon bond is thought to form dehydrosecodine. The enzymes forming stemmadenine and using it as a substrate remain unknown to date. It is thought to be intermediate compound in many different biosynthetic pathways such as in Aspidosperma species. Many alkaloids are proposed to be produced through intermediate stemmadenine. Some of them are:

It is also present as product in plant like in Tabernaemontana dichotoma seeds.

Pharmacology

It has hypotensive and weak muscle relaxant properties.

See also

References

  1. ↑ Scott AI, Qureshi AA (1969). "Biogenesis of Strychnos, Aspidosperma, and Iboga alkaloids. Structure and reactions of preakuammicine". Journal of the American Chemical Society. 91 (21): 5874–6. doi:10.1021/ja01049a032. PMID 5812148.
  2. 1 2 Qu Y, Easson ME, Simionescu R, Hajicek J, Thamm AM, Salim V, De Luca V (March 2018). "Solution of the multistep pathway for assembly of corynanthean, strychnos, iboga, and aspidosperma monoterpenoid indole alkaloids from 19E-geissoschizine". Proceedings of the National Academy of Sciences of the United States of America. 115 (12): 3180–3185. Bibcode:2018PNAS..115.3180Q. doi:10.1073/pnas.1719979115. PMC 5866588. PMID 29511102.
  3. 1 2 Kalshetti MG, Argade NP (2020). "The indole-based subincanadine alkaloids and their biogenetic congeners". The Alkaloids. Chemistry and Biology. 83: 187–223. doi:10.1016/bs.alkal.2019.12.001. ISBN 9780128209813. PMID 32098650. S2CID 211524741.{{cite journal}}: CS1 maint: periodical has ISBN (link)
  4. 1 2 El-Sayed M, Choi YH, Frédérich M, Roytrakul S, Verpoorte R (May 2004). "Alkaloid accumulation in Catharanthus roseus cell suspension cultures fed with stemmadenine". Biotechnology Letters. 26 (10): 793–8. doi:10.1023/b:bile.0000025879.53632.f2. hdl:1887/4092402. PMID 15269549. S2CID 22411370.
  5. ↑ de Almeida VL, Silva CG, Silva AF, Campana PR, Foubert K, Lopes JC, Pieters L (March 2019). "Aspidosperma species: A review of their chemistry and biological activities". Journal of Ethnopharmacology. 231: 125–140. doi:10.1016/j.jep.2018.10.039. hdl:10067/1556490151162165141. PMID 30395977. S2CID 53223901.
  6. 1 2 Perera P, Kanjanapothy D, Sandberg F, Verpoorte R (May 1985). "Muscle relaxant activity and hypotensive activity of some Tabernaemontana alkaloids". Journal of Ethnopharmacology. 13 (2): 165–73. doi:10.1016/0378-8741(85)90004-2. PMID 4021514.