A pyrrolizidine alkaloid with hepatotoxic properties
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Senecionine

Item No. 25145

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
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(Learn about Variance in Solubility)
DMF: 5 mg/mlDMSO: 2 mg/mlEthanol: 1 mg/mlPBS (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.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    5 mg

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    10 mg

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    Product Description

    Senecionine is a pyrrolizidine alkaloid that has been found in S. vulgaris and has hepatotoxic properties.1 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.2,3 Senecionine (20 μM) induces mitochondrial depolarization and fragmentation in primary cultured mouse hepatocytes and increases apoptosis in a concentration-dependent manner.2 In rats, senecionine (35 mg/kg, p.o.) induces liver injury, increases serum levels of bilirubin (Item No. 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.1 Senecionine-induced hepatotoxicity is associated with lipid peroxidation and glutathione depletion.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Xiong, A., Yang, F., Fang, L., et al. Metabolomic and genomic evidence for compromised bile acid homeostasis by senecionine, a hepatotoxic pyrrolizidine alkaloid. Chem. Res. Toxicol. 27(5), 775-786 (2014).

    2. Yang, X., Wang, H., Ni, H.-M., et al. Inhibition of Drp1 protects against senecionine-induced mitochondria-mediated apoptosis in primary hepatocytes and in mice. Redox Biol. 12, 264-273 (2017).

    3. Miranda, C.L., Reed, R.L., Guengerich, F.P., et al. Role of cytochrome P450IIIA4 in the metabolism of the pyrrolizidine alkaloid senecionine in human liver. Carcinogenesis 12(3), 515-519 (1991).