Lochnericine

{{Short description|Chemical compound}}

{{Drugbox

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| IUPAC_name = 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

| image = Lochnericine.png

| image_class = skin-invert-image

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| CAS_number_Ref =

| CAS_number =72058-36-7

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| PubChem = 11382599

| ChemSpiderID_Ref =

| ChemSpiderID =391593

| KEGG = C11676

| UNII_Ref =

| UNII = WY97J4B4AM

| ChEBI = 6510

| ChEMBL_Ref =

| ChEMBL = CHEMBL2011514

| C=21 | H=24 | N=2 | O=3

| StdInChI=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

| StdInChIKey = AUVZFRDLRJQTQF-KXEYLTKFSA-N

| SMILES = CC[C@]12CC(=C3[C@@]4([C@H]1N(CC4)C[C@H]5[C@@H]2O5)C6=CC=CC=C6N3)C(=O)OC

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Lochnericine is an indole alkaloid present in the roots of Catharanthus roseus. It is also present in Tabernaemontana divaricata.{{cite journal | vauthors = Carqueijeiro I, Brown S, Chung K, Dang TT, Walia M, Besseau S, Dugé de Bernonville T, Oudin A, Lanoue A, Billet K, Munsch T, Koudounas K, Melin C, Godon C, Razafimandimby B, de Craene JO, Glévarec G, Marc J, Giglioli-Guivarc'h N, Clastre M, St-Pierre B, Papon N, Andrade RB, O'Connor SE, Courdavault V | display-authors = 6 | title = Two Tabersonine 6,7-Epoxidases Initiate Lochnericine-Derived Alkaloid Biosynthesis in Catharanthus roseus | journal = Plant Physiology | volume = 177 | issue = 4 | pages = 1473–1486 | date = August 2018 | pmid = 29934299 | pmc = 6084683 | doi = 10.1104/pp.18.00549 }}

Chemistry

= Synthesis =

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

=Derivatives=

See also

References