Tabersonine

Tabersonine
Names
IUPAC name
Methyl 2,3,6,7-tetradehydro-5α,12β,19α-aspidospermidine-3-carboxylate
Systematic IUPAC name
Methyl (3aR,3a1S,10bR)-3a-ethyl-3a,3a1,4,6,11,12-hexahydro-1H-indolizino[8,1-cd]carbazole-5-carboxylate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.022.378
KEGG
UNII
  • InChI=1S/C21H24N2O2/c1-3-20-9-6-11-23-12-10-21(19(20)23)15-7-4-5-8-16(15)22-17(21)14(13-20)18(24)25-2/h4-9,19,22H,3,10-13H2,1-2H3/t19-,20-,21-/m0/s1
    Key: FNGGIPWAZSFKCN-ACRUOGEOSA-N
  • CC[C@]12CC(=C3[C@@]4([C@H]1N(CC4)CC=C2)c5ccccc5N3)C(=O)OC
Properties
C21H24N2O2
Molar mass 336.435 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

Tabersonine is a terpene indole alkaloid found in the medicinal plant Catharanthus roseus and also plants in the genus Voacanga[1]: 8  (both taxa belonging to the alkaloid-rich family Apocynaceae). Tabersonine is hydroxylated at the 16 position by the enzyme tabersonine 16-hydroxylase to form 16-hydroxytabersonine.[2] Tabersonine is the first intermediate leading to the formation of vindoline one of the two precursors required for vinblastine biosynthesis.

Biosynthesis

Tabersonine is an indole alkaloid whose immediate precursor in Catharanthus roseus (Madagascar periwinkle) is the compound dehydrosecodine. This is cyclised by the enzyme tabersonine synthase:[3][4]

2D representation of the chemical structure of dehydrosecodine .
dehydrosecodine
Synthase
 
 
Rightward reaction arrow
 
 
 
2D representation of the chemical structure of tabersonine .
tabersonine

The biosynthetic pathway to vindoline and vinblastine continues when tabersonine is hydroxylated by the enzyme tabersonine 16-hydroxylase, giving 16-hydroxytabersonine:[4]

2D representation of the chemical structure of tabersonine .
tabersonine
 
O2
2 H2O
Rightward reaction arrow with minor substrate(s) from top left and minor product(s) to top right
 
 
 
2D representation of the chemical structure of 16-Hydroxytabersonine.
16-hydroxytabersonine

See also

References

  1. ↑ Van Beek, T.A.; Verpoorte, R.; Svendsen, A.Baerheim; Leeuwenberg, A.J.M.; Bisset, N.G. (1984). "Tabernaemontana L. (Apocynaceae): A review of its taxonomy, phytochemistry, ethnobotany and pharmacology". Journal of Ethnopharmacology. 10 (1): 1–156. doi:10.1016/0378-8741(84)90046-1. PMID 6371388.
  2. ↑ St-Pierre, B.; De Luca, V. (1995). "A Cytochrome P-450 Monooxygenase Catalyzes the First Step in the Conversion of Tabersonine to Vindoline in Catharanthus roseus". Plant Physiology. 109 (1): 131–139. doi:10.1104/pp.109.1.131. PMC 157569. PMID 12228585.
  3. ↑ Caputi, Lorenzo; Franke, Jakob; Farrow, Scott C.; et al. (2018). "Missing enzymes in the biosynthesis of the anticancer drug vinblastine in Madagascar periwinkle". Science. 360 (6394): 1235–1239. doi:10.1126/science.aat4100. PMID 29724909.
  4. 1 2 Demars, Matthew D.; o'Connor, Sarah E. (2024). "Evolution and diversification of carboxylesterase-like [4+2] cyclases in aspidosperma and iboga alkaloid biosynthesis". Proceedings of the National Academy of Sciences. 121 (7) e2318586121. doi:10.1073/pnas.2318586121. PMID 38319969.
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