SENECIONINE-N-OXIDE
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Drawn and modelled with RDKit, 3D viewer 3Dmol.js. PubChem CID 5380876
Name
SENECIONINE-N-OXIDE
IUPAC name
(5R,6R,9a1R,14aR,Z)-3-ethylidene-6-hydroxy-5,6-dimethyl-2,7-dioxo-2,3,4,5,6,7,9,9a1,11,13,14,14a-dodecahydro-12H-[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine 12-oxide
SMILES
C/C=C\1/C[C@H]([C@@](C(=O)OCC2=CC[N+]3([C@H]2[C@@H](CC3)OC1=O)[O-])(C)O)C
Molecular formula
C18H25NO6
Molecular weight
351.40 g/mol
Monoisotopic mass
351.1682 Da
Chemical classification: NPClassifier (Kim et al., 2021)
| Plant | Plant part | Amount | Reference |
|---|---|---|---|
| Senecio vulgaris L. subsp. vulgaris | - | - |
Kery, A. (1973). Changes in the tertiary and n-oxide alkaloids of Senecio vulgaris by organs during the vegetative period. Herba Hung, 12(3), 29
|
| Senecio vulgaris L. subsp. vulgaris | - | - |
Tu, Z.B., Konno, C., Soejato, D.D., Waller, D.P., Bingel, A.S., Molyneux, R.J., Edgar, J.A., Cordell, G.A., Fong, H.H.S. (1988). Identification of Senecionine and Senecionine-n-oxide as antifertility constituents in Senecio vulgaris. J Pharm Sci, 77(5), 461-463 doi:10.1002/jps.2600770522
|
| Senecio vulgaris L. subsp. vulgaris | aerial parts | - |
Ingolfsdottir, K., Hylands, P.J. (1990). Pyrrolizidine alkaloids in Senecio vulgaris L. growing in iceland. Acta Pharm Nordica, 2(5), 343-348
|
| Senecio vulgaris L. subsp. vulgaris | cell culture | - |
Ehmke, A., Vonborstel, K., Hartmann, T. (1988). Alkaloid n-oxides as transport and vacuolar storage compounds of pyrrolizidine alkaloids in Senecio vulgaris L. Planta, 176, 83-90 doi:10.1007/bf00392483
|
| Senecio vulgaris L. subsp. vulgaris | cell culture | - |
Graser, G., Hartmann, T. (1997). Biosynthetic incorporation of the aminobutyl group of spermidine into pyrrolizidine alkaloids. Phytochemistry, 45(8), 1591-1595 doi:10.1016/s0031-9422(97)00193-3
|
| Senecio vulgaris L. subsp. vulgaris | leaf | - |
Kery, A. (1975). Free and n-oxide alkaloids of Senecio vulgaris. changes in the contents of alkaloids in various organs during the vegetation period. Acta Agron Acad Sci Hung, 24, 3
|
| Senecio vulgaris L. subsp. vulgaris | root | - |
Hartmann, T., Adolph, R.D., Ehmke, A., Sander, H., Toppel, G., Witte, L. (1987). The role of the n-oxides in biosynthesis and accumulation of pyrrolizidine alkaloids. Pharm Weekbl(Sci Ed), 9(4), 216
|