Senecionine

Senecionine is a pyrrolizidine alkaloid that has been found in S. vulgaris and has hepatotoxic properties. It is metabolized by the cytochrome P450 (CYP) isoform CYP3A in the liver to the detoxification product senecionine N-oxide and reactive metabolites including dehydropyrrolizidine alkaloids and dehydrotetronecine. Senecionine (20 µM) induces mitochondrial depolarization and fragmentation in primary cultured mouse hepatocytes and increases apoptosis in a concentration-dependent manner. In rats, senecionine (35 mg/kg, p.o.) induces liver injury, increases serum levels of bilirubin (Cay-17161) and various bile acids, including taurocholic acid, glycocholic acid, and deoxycholic acid, and increases the activity of alanine aminotransferase and aspartate aminotransferase in serum. Senecionine-induced hepatotoxicity is associated with lipid peroxidation and glutathione depletion.Formal Name: (3Z,5R,6R,14aR,14bR)-3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-5,6-dimethyl-[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione. CAS Number: 130-01-8. Synonyms: NSC 89935, (-)-Senecionine. Molecular Formula: C18H25NO5. Formula Weight: 335.4. Purity: >98%. Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: 5 mg/ml, DMSO: 2 mg/ml, Ethanol: 1 mg/ml, PBS (pH 7.2): 0.1 mg/ml. SMILES: O=C(/C(C[C@@H](C)[C@@]1(C)O)=C\C)O[C@]2([H])CCN3[C@]2([H])C(COC1=O)=CC3. InChi Code: InChI=1S/C18H25NO5/c1-4-12-9-11(2)18(3,22)17(21)23-10-13-5-7-19-8-6-14(15(13)19)24-16(12)20/h4-5,11,14-15,22H,6-10H2,1-3H3/b12-4-/t11-,14-,15-,18-/m1/s1. InChi Key: HKODIGSRFALUTA-JTLQZVBZSA-N. Origin: Plant/Senecio scandens Buch.-Ham..