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
CAS Number	10012-73-4 [KEGG];
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:9260;
ChEMBL	ChEMBL486212;
ChemSpider	8242264;
KEGG	C11691;
PubChem CID	10066724;
UNII	7RBX39D6AB ;
	InChI 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;
	SMILES C/C=C\1/CN2CC[C@H]1[C@](C3=C(CC2)C4=CC=CC=C4N3)(CO)C(=O)OC;
Properties
Chemical formula	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). Infobox references

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.^[1] 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^[2]^[3]^[4] such as in Aspidosperma species.^[5] Many alkaloids are proposed to be produced through intermediate stemmadenine. Some of them are:

Catharanthine and Tabersonine in Catharanthus roseus^[4]^[2]
Subincanadines D-F in Aspidosperma subincanum^[3]

It is also present as product in plant like in Tabernaemontana dichotoma seeds.^[6]

Pharmacology

It has hypotensive and weak muscle relaxant properties.^[6]

References

^ 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.
^ ^a ^b 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.
^ ^a ^b 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.
^ ^a ^b 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. PMID 15269549. S2CID 22411370.
^ 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.
^ ^a ^b 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.

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[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.

[pmid29511102-2] 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.

[pmid32098650-3] 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.

[pmid15269549-4] 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. PMID 15269549. S2CID 22411370.

[pmid30395977-5] 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.

[pmid4021514-6] 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.

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[6]

Pharmacology

See also

References