Senecionine

Senecionine (Senecionan-11,16-dione, 12-hydroxy-) is a pyrrolizidine alkaloid isolated from Senecio vulgaris. Senecionine is toxic to animals and humans.

Product information

CAS Number: 130-01-8

Molecular Weight: 335.39

Formula: C18H25NO5

Synonym:

Senecionan-11,16-dione, 12-hydroxy-

Aureine

Senecionin

Chemical Name: (1R,4Z,6R,7R,17R)-4-ethylidene-1,17-dihydrogenio-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione

Smiles: C[C@@H]1C/C(=C/C)/C(=O)O[C@@H]2CCN3CC=C(COC(=O)[C@]1(C)O)[C@@H]32

InChiKey: HKODIGSRFALUTA-JTLQZVBZSA-N

InChi: 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

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

Pyrrolizidine alkaloids (PAs) are considered to be one of the most hepatotoxic groups of compounds of plant origin and are present in about 3% of the world's flowering plants. Most PAs represent a considerable health hazard to both livestock and humans through the consumption of plants and PA-contaminated products such as milk, honey, herbal teas, and medicines.

In Vivo:

Upon intravenous administration and oral administration of Senecionine and Adonifoline, significant differences in pharmacokinetics were observed, with the Senecionine and Adonifoline being absorbed fast with lower bioavailability and being quickly metabolized to PA N-oxides and hydroxylation products of PAs or their N-oxides. Senecionine fails to stimulate epoxide hydrase, it diminishs the activity of glutathione-s-transferase, aminopyrine demethylase and AHH. Twice-weekly injections of a third constituent, senecionine, beginning on Day 12 or later, results in premature deliveries in three of seven rats, and the pups from all litters are stillborn or die shortly after birth.

References:

1. Wang C, et al. The comparative pharmacokinetics of two pyrrolizidine alkaloids, senecionine and adonifoline, and their main metabolites in rats after intravenous and oral administration by UPLC/ESIMS. Anal Bioanal Chem. 2011 Jul;401(1):275-87.
2. Kakrani HK, et al. Effect of seneciphylline and senecionine on hepatic drug metabolizing enzymes in rats. J Ethnopharmacol. 1984 Dec;12(3):271-8.
3. Tu ZB, et al. Identification of senecionine and senecionine N-oxide as antifertility constituents in Senecio vulgaris. J Pharm Sci. 1988 May;77(5):461-3.

Products are for research use only. Not for human use.