130-01-8 Usage
Description
Senecionine is a hepatotoxic pyrrolizidine alkaloid that is widely distributed among the Senecio species. 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 has been found to induce mitochondrial depolarization, fragmentation, and apoptosis in primary cultured mouse hepatocytes in a concentration-dependent manner. It also causes liver injury, increases serum levels of bilirubin and various bile acids, and raises the activity of alanine aminotransferase and aspartate aminotransferase in rats.
Used in Pharmaceutical Industry:
Senecionine is used as a research compound for studying its hepatotoxic properties and exploring its potential applications in drug development. Its metabolism and toxic effects can provide insights into the development of new drugs targeting specific enzymes or pathways involved in liver injury and disease.
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)
Check Digit Verification of cas no
The CAS Registry Mumber 130-01-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,3 and 0 respectively; the second part has 2 digits, 0 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 130-01:
(5*1)+(4*3)+(3*0)+(2*0)+(1*1)=18
18 % 10 = 8
So 130-01-8 is a valid CAS Registry Number.
InChI:InChI=1/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
130-01-8Relevant articles and documents
Total synthesis of optically active integerrimine, a twelve-membered dilactonic pyrrolizidine alkaloid of retronecine type. III. Regioselective elaboration of the unsymmetrical twelve-membered dilactone and total synthesis of (-)-integerrimine
Niwa,Miyachi,Uosaki,et al.
, p. 4609 - 4610 (1986)
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Identification of senecionine and senecionine N-oxide as antifertility constituents in Senecio vulgaris
Tu,Konno,Soejarto,Waller,Bingel,Molyneux,Edgar,Cordell,Fong
, p. 461 - 463 (1988)
The MeOH extract of Senecio vulgaris L., administered po to rats on Days 1-10 postcoitum, significantly decreased the number of normal fetuses per pregnant rat found at autopsy on Day 16. Additional experiments showed a similar activity for its hepatotoxic constituents senecionine and senecionine N-oxide, suggesting that the latter two compounds were probably responsible for the effect seen with the extract. No antifertility effects were seen in MeOH extract-treated hamsters.
Total Synthesis of Optically Active Integerrimine, a Twelve-membered Dilactonic Pyrrolizidine Alkaloid of Retronecine Type
Niwa, Haruki,Miyachi, Yasuyoshi,Okamoto, Osamu,Uosaki, Youichi,Kuroda, Akio,et al.
, p. 393 - 412 (2007/10/02)
A total synthesis of the natural enantiomer of integerrimine (1), a twelve-membered dilactonic pyrrolizidine alkaloid of retronecine type has been achieved through the enantioselective synthesis and regioselective coupling of (+)-retronecine (4) and (+)-integerrinecic acid (methylthio)methyl ether (6).