Tabersonine

Tabersonine is a terpene indole alkaloid found in the medicinal plant Catharanthus roseus and also in the genus Voacanga[1] (both taxa belonging to the alkaloid-rich family Apocynaceae). Tabersonine is hydroxylated at the 16 position by the enzyme tabersonine 16-hydroxylase (T16H) to form 16-hydroxytabersonine.[2] The enzyme leading to its formation is currently unknown. Tabersonine is the first intermediate leading to the formation of vindoline one of the two precursors required for vinblastine biosynthesis.

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
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
  • InChI=1/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-ACRUOGEOBF
  • 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

See also

References
  1. Voacanga, (Apocynaceae), a review of its taxonomy, phytochemistry, ethnobotany and pharmacology. Leeuwenberg et al Agric. Univ. Wagenigen papers #85-3, 1985. Page 8
  2. St-Pierre and De Luca (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
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