SENECIONINE
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Drawn and modelled with RDKit, 3D viewer 3Dmol.js. PubChem CID 5280906
Name
SENECIONINE
IUPAC name
(5R,6R,9a1R,14aR,Z)-3-ethylidene-6-hydroxy-5,6-dimethyl-3,4,5,6,9,9a1,11,13,14,14a-decahydro-[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione
SMILES
C/C=C\1/C[C@H]([C@@](C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC1=O)(C)O)C
Molecular formula
C18H25NO5
Molecular weight
335.40 g/mol
Monoisotopic mass
335.1733 Da
Chemical classification: NPClassifier (Kim et al., 2021)
| Plant | Plant part | Amount | Reference |
|---|---|---|---|
| Jacobaea erucifolia (L.) G.Gaertn., B.Mey. & Scherb. subsp. erucifolia | - | - |
Kompis, I., Santavy, F. (1962). Alkaloids of Senecio erucifolius. Collect Czech Chem Commun, 27, 1413
|
| Jacobaea erucifolia (L.) G.Gaertn., B.Mey. & Scherb. subsp. erucifolia | flower | - |
Ferry, S., Brazier, J.L. (1976). Some indigenous Senecio alkaloids. 2. indentification and structures. Ann Pharm Fr, 34, 133-138
|
| Leucanthemum vulgare (Vaill.) Lam. subsp. vulgare | flower | - |
Sagareishvili, T.G. (2000). Alkaloids of Leucanthemum vulgare. Chem Nat Comp, 36(3), 327 doi:10.1007/bf02238350
|
| Petasites hybridus (L.) G.Gaertn., B.Mey. & Scherb. subsp. hybridus | - | - |
Duke, James A. 1992. Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.
|
| Petasites hybridus (L.) G.Gaertn., B.Mey. & Scherb. subsp. hybridus | leaf | - |
Wichtl, M. 1984. Teedrogen. Ein Handbuch fur Apotheker und Arzte. Wissenschaftliche Verlagsgesellscharft. mbH Stuttgart. 393 pp.
|
| Petasites hybridus (L.) G.Gaertn., B.Mey. & Scherb. subsp. hybridus | root | - |
Duke, James A. 1992. Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.
|
| Senecio inaequidens DC. | - | - |
Bicchi, C., Rubiolo, P., Frattini, C., Sandra, P., David, F. (1991). Off-line supercritical fluid extraction and capillary gas chromatography of pyrrolizidine alkaloids in Senecio species. J Nat Prod, 54(4), 941-945 doi:10.1021/np50076a003
|
| Senecio inaequidens DC. | aerial parts | - |
Rubiolo, P., Pieters, L., Calomme, M., Bicchi, C., Vlietinck, A., Vandenberghe, D. (1992). Mutagenicity of pyrrolizidine alkaloids in the salmonella typhimurium/mammalian microsome system. Mutat Res, 281(2), 143-147 doi:10.1016/0165-7992(92)90050-r
|
| Senecio ovatus (G.Gaertn., B.Mey. & Scherb.) Willd. subsp. alpestris (Gaudin) Herborg | - | - |
Wiedenfeld, H., Hendriks, H., Roder, E. (1986). The alkaloid content of Senecio nemorensis, ssp. nemorensis and Senecio nemorensis, ssp. fuchsii. Planta Med, 52(5), 426 doi:10.1055/s-2007-969230
|
| Senecio ovatus (G.Gaertn., B.Mey. & Scherb.) Willd. subsp. alpestris (Gaudin) Herborg | aerial parts | - |
Wiedenfeld, H., Pastewka, W., Stengl, P., Roder, E. (1981). On the gas-chromatographical determination of the pyrrolizidine alkaloids of some Senecio-species. Planta Med, 41, 124-126
|
| Senecio vulgaris L. subsp. vulgaris | - | - |
Barger, G., Blackie, J.J. (1936). Alkaloids of Senecio. ii. Senecionine and squalidine. J Chem Soc, 743-745 doi:10.1039/jr9360000743
|
| Senecio vulgaris L. subsp. vulgaris | - | - |
Chen, K.K., Harris, P.N., Rose, C.I. (1940). The action and toxicity of platyphylline and seneciphylline. J Pharmacol Exp Ther, 68, 130 doi:10.1016/s0022-3565(25)06450-x
|
| Senecio vulgaris L. subsp. vulgaris | - | - |
Reed, R.L., Reed, B.M., Buhler, D.R. (1985). Biosynthesis of radiolabeled pyrrolizidine alkaloids from Senecio jacobaea and Senecio vulgaris. Planta Med, 51(5), 472 doi:10.1055/s-2007-969565
|
| Senecio vulgaris L. subsp. vulgaris | aerial parts | - |
No reference
|
| Senecio vulgaris L. subsp. vulgaris | aerial parts | - |
Luthy, J., Heim, T.H., Schlatter, C.H. (1983). Transfer of [3-h]pyrrolizidine alkaloids from Senecio vulgaris L. and metabolites into rat milk and tissues. Toxicol Lett, 17(3/4), 283-288 doi:10.1016/0378-4274(83)90239-4
|
| Senecio vulgaris L. subsp. vulgaris | aerial parts | - |
Willaman, J.J., Schubert, B.G. (1961). Alkaloid bearing plants and their contained alkaloids.
|
| 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 | leaf | - |
Ehmke, A., Proksch, P., Witte, L., Hartmann, T., Isman, M.B. (1989). Fate of ingested pyrrolizidine alkaloid n-oxide in the grasshopper Melanoplus sanguinipes. Naturwissenschaften, 76(1), 27-29 doi:10.1007/bf00368308
|
| 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 | - |
Dorling, P.R., Mccomb, J., Colegate, S.M., Lambert, K., Jawaheer, S. (1998). [14-c]senecionine production in Senecio vulgaris root culture. Toxic Plants Other Nat Toxicants [Proc Int Symp Poisonous Plants] 5Th 1997, 55-61
|
| Senecio vulgaris L. subsp. vulgaris | seed | - |
Candrian, U., Luethy, J., Schlatter, C. (1985). In vivo covalent binding of retronecine-labeled [h]senseciphylline and [h]Senecionine to dna of rat liver, lung and kidney. Chem Biol Interact, 54(1), 57-69 doi:10.1016/s0009-2797(85)80152-6
|
| Senecio vulgaris L. subsp. vulgaris | seedling | - |
Reed, R.L., Reed, B.M., Buhler, D.R. (1985). Biosynthesis of radiolabeled pyrrolizidine alkaloids from Senecio jacobaea and Senecio vulgaris. Planta Med, 51(5), 472 doi:10.1055/s-2007-969565
|