SENECIPHYLLINE
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Drawn and modelled with RDKit, 3D viewer 3Dmol.js. PubChem CID 5281750
Name
SENECIPHYLLINE
IUPAC name
(6R,9a1R,14aR,Z)-3-ethylidene-6-hydroxy-6-methyl-5-methylene-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/CC(=C)[C@@](C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC1=O)(C)O
Molecular formula
C18H23NO5
Molecular weight
333.38 g/mol
Monoisotopic mass
333.1576 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
|
| 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 vulgaris L. subsp. vulgaris | - | - |
Chizzola, R. (1994). Rapid sample preparation technique for the determination of pyrrolizidine alkaloids in plant extracts. J Chromatogr A, 668(2), 427-433 doi:10.1016/0021-9673(94)80135-5
|
| 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 | - | - |
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 | - | - |
Willaman, J.J., Schubert, B.G. (1961). Alkaloid bearing plants and their contained alkaloids.
|
| 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 | - |
Molyneux, R.J., Johnson, A.E., Boitman, J.N., Benson, M.E. (1979). Chemistry of toxic range plants. determination of pyrrolizidine alkaloid content and composition in Senecio species by nuclear magnetic resonance spectroscopy. J Agr Food Chem, 27(3), 494 doi:10.1021/jf60223a002
|
| 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 | 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
|