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
CAS Number	4429-63-4 ; 29479-00-3 (hydrochloride) ;
3D model (JSmol)	Interactive image;
ChemSpider	19292;
ECHA InfoCard	100.022.378
PubChem CID	20485;
UNII	MN955K48NB ;
CompTox Dashboard (EPA)	DTXSID30196102 ;
	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;
	SMILES CC[C@]12CC(=C3[C@@]4([C@H]1N(CC4)CC=C2)c5ccccc5N3)C(=O)OC;
Properties
Chemical formula	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 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.

References

^ Voacanga, (Apocynaceae), a review of its taxonomy, phytochemistry, ethnobotany and pharmacology. Leeuwenberg et al Agric. Univ. Wagenigen papers #85-3, 1985. Page 8
^ 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

[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

[1]

[2]

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
CAS Number	4429-63-4^Y 29479-00-3 (hydrochloride)^Y
3D model (JSmol)	Interactive image
ChemSpider	19292
ECHA InfoCard	100.022.378
PubChem CID	20485
UNII	MN955K48NB^Y
CompTox Dashboard (EPA)	DTXSID30196102
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
SMILES CC[C@]12CC(=C3[C@@]4([C@H]1N(CC4)CC=C2)c5ccccc5N3)C(=O)OC
Properties
Chemical formula	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

See also

References