Stemmadenine Explained

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
• Subincanadines D-F in Aspidosperma subincanum

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

Pharmacology

It has hypotensive and weak muscle relaxant properties.

See also

• Secologanin
• Strictosidine

Notes and References

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