Tabersonine

Tabersonine
Names

IUPAC name Methyl (5α,12β,19α)-2,3,6,7-tetradehydroaspidospermidine-3-carboxylate
Identifiers
CAS Registry Number	29479-00-3
ChemSpider	19292
InChI 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
Jmol-3D images	Image
PubChem	20485
SMILES CC[C@]12CC(=C3[C@@]4([C@H]1N(CC4)CC=C2)c5ccccc5N3)C(=O)OC
Properties
Molecular formula	C₂₁H₂₄N₂O₂
Molar mass	336.43 g·mol⁻¹
Except where noted otherwise, data is 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. Tabersonine is hydroxylated at the 16 position by the enzyme tabersonine 16-hydroxylase (T16H) to form 16-hydroxytabersonine.^[1] 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.

References

↑ 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