SENECIONINE

Synonym(s):Aureine

CAS NO.：130-01-8
Empirical Formula: C18H25NO5
Molecular Weight: 335.39
MDL number: MFCD00221720
SAFETY DATA SHEET (SDS)
Update Date: 2024-11-19 23:02:33

What is SENECIONINE?

Description

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 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.

Description

This hepatotoxic alkaloid is widely distributed among the Senecio species, being found in S. aureus, S. ilicifolius Thunb., S. integerrirnus, S. pseudaarnica, S. squaUdus, S. viscosus and S. vulgaris. The base is laevorotatory with [α]_D - 54.6° (CHCI₃ ) and the crystals sublime at 130-140°CfO.2 mm. The nitrate has m.p. 214°C;[α]_D - 34.2° (H₂ 0); the aurichloride, m.p. 186°C; the picrate, m.p. 191°C and the methiodide, m.p. 249°C. Alkaline hydrolysis furnishes retronecine and senecic acid (6-hydroxy-5-methyl-2-heptene-3 :6-dicarboxylic acid).

The Uses of SENECIONINE

Senecionine is a pyrrolizidine alkaloid with the potential to affect hepatic drug metabolizing enzymes in rat cells.

Definition

ChEBI: A pyrrolizidine alkaloid isolated from the plant species of the genus Senecio.

Safety Profile

Poison by intravenous,intraperitoneal, and possibly other routes. Anexperimental teratogen. Other experimental reproductiveeffects. Mutation data reported. When heated todecomposition it emits toxic fumes of NOx.

References

Grandval, Lajoux., Cornpt. rend., 120,1120 (1895)
Grandval, Lajoux., Bull. Soc. Chirn. Fr., 13,942 (1895)
Manske., Can. J. Res., S, 651 (1931)
Manske., ibid, 14B, 6 (1936)
Barger, Blackie., J. Chern. Soc., 584 (1937)
Blackie., Pharrn. J., 138,102 (1937)
Manske., Can. J. Res., 17B, I (1939)

Properties of SENECIONINE

Melting point:	236 °C(lit.)
Boiling point:	472.03°C (rough estimate)
alpha	D25 -55.1° (c = 0.034 in chloroform)
Density	1.266 g/cm3
refractive index	1.5100 (estimate)
storage temp.	−20°C
solubility	DMF: 5 mg/ml; DMSO: 2 mg/ml; Ethanol: 1 mg/ml; PBS (pH 7.2): 0.1 mg/ml
pka	12.81±0.40(Predicted)
form	Solid
form	neat
color	White to off-white
optical activity	[α]25/D 55.1°, c = 0.034% in chloroform
BRN	8162955
EPA Substance Registry System	Senecionine (130-01-8)

Safety information for SENECIONINE

Signal word	Danger
Pictogram(s)	Skull and Crossbones Acute Toxicity GHS06
Precautionary Statement Codes	P262:Do not get in eyes, on skin, or on clothing. P280:Wear protective gloves/protective clothing/eye protection/face protection.