Lochnericine

Lochnericine is a major monoterpene indole alkaloid present in the roots of Catharanthus roseus. It is also present in Tabernaemontana divaricata.[1]

Lochnericine
Identifiers
  • methyl (1R,12S,13R,15S,20R)-12-ethyl-14-oxa-8,17-diazahexacyclo[10.7.1.01,9.02,7.013,15.017,20]icosa-2,4,6,9-tetraene-10-carboxylate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Chemical and physical data
FormulaC21H24N2O3
Molar mass352.434 g·mol−1
3D model (JSmol)
  • CC[C@]12CC(=C3[C@@]4([C@H]1N(CC4)C[C@H]5[C@@H]2O5)C6=CC=CC=C6N3)C(=O)OC
  • InChI=1S/C21H24N2O3/c1-3-20-10-12(18(24)25-2)16-21(13-6-4-5-7-14(13)22-16)8-9-23(19(20)21)11-15-17(20)26-15/h4-7,15,17,19,22H,3,8-11H2,1-2H3/t15-,17-,19-,20+,21-/m0/s1
  • Key:AUVZFRDLRJQTQF-KXEYLTKFSA-N


Chemistry

Synthesis

Lochnericine is formed from stereoselective epoxidation of carbons 6 and 7 of tabersonine.[1]

See also

References
  1. Carqueijeiro I, Brown S, Chung K, Dang TT, Walia M, Besseau S, et al. (August 2018). "Two Tabersonine 6,7-Epoxidases Initiate Lochnericine-Derived Alkaloid Biosynthesis in Catharanthus roseus". Plant Physiology. 177 (4): 1473–1486. doi:10.1104/pp.18.00549. PMC 6084683. PMID 29934299.
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