130-01-8 Usage
Description
Different sources of media describe the Description of 130-01-8 differently. You can refer to the following data:
1. 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).
2. 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.
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)
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).