16-Methoxytabersonine
Names
IUPAC name
Methyl 16-methoxy-2,3,6,7-tetradehydro-5α,12β,19α-aspidospermidine-3-carboxylate
Systematic IUPAC name
Methyl (3aR,3a1S,10bS)-3a-ethyl-8-methoxy-3a,3a1,4,6,11,12-hexahydro-1H-indolizino[8,1-cd]carbazole-5-carboxylate
Other names
Ervamycine
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C22H26N2O3/c1-4-21-8-5-10-24-11-9-22(20(21)24)16-7-6-14(26-2)12-17(16)23-18(22)15(13-21)19(25)27-3/h5-8,12,20,23H,4,9-11,13H2,1-3H3/t20-,21-,22-/m0/s1
    Key: AEXBRBWRPNGGEZ-FKBYEOEOSA-N
  • InChI=1/C22H26N2O3/c1-4-21-8-5-10-24-11-9-22(20(21)24)16-7-6-14(26-2)12-17(16)23-18(22)15(13-21)19(25)27-3/h5-8,12,20,23H,4,9-11,13H2,1-3H3/t20-,21-,22-/m0/s1
    Key: AEXBRBWRPNGGEZ-FKBYEOEOBC
  • CC[C@]12CC(=C3[C@@]4([C@H]1N(CC4)CC=C2)c5ccc(cc5N3)OC)C(=O)OC
Properties
C22H26N2O3
Molar mass 366.461 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

16-Methoxytabersonine is a terpene indole alkaloid produced by the medicinal plant Catharanthus roseus. 16-methoxytabersonine is synthesized by methylation of the hydroxyl group at the 16 position of 16-hydroxytabersonine by tabersonine 16-O-methyltransferase (16OMT).[1] The compound is a substrate for hydration by two concerted enzymes Tabersonine-3-Oxidase (T3O) and Tabersonine-3-Reductase (T3R), which leads to the formation of 3-hydroxy-16-methoxy-2,3-dihydrotabersonine.[2]

References

  1. ↑ Levac, Murata, Kim and De Luca (2008) Application of carborundum abrasion for investigating the leaf epidermis: molecular cloning of Catharanthus roseus 16-hydroxytabersonine-16-O-methyltransferase. The Plant Journal. 53(2). 225-236
  2. ↑ Qu, Y., Easson, M. L., Froese, J., Simionescu, R., Hudlicky, T., & De Luca, V. (2015). Completion of the seven-step pathway from tabersonine to the anticancer drug precursor vindoline and its assembly in yeast. Proceedings of the National Academy of Sciences, 112(19), 6224-6229.
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