12-ヒドロキシセネシオナン-11,16-ジオン 化学特性,用途語,生産方法
解説
セネシオニン，キク目ハンゴンソウSenecio platyphyllos，ダンドボロギクErechtites hieracifoliaなどに広く分布するセネシオアルカロイドの一種．板状晶．融点236 ℃，昇華点129 ℃(27 Pa)．[α]D－56°(クロロホルム)．水に不溶，有機溶媒に可溶．加水分解によって，セネシン酸(senecic acid，融点147 ℃)と，レトロネシンとを与える．肝臓毒で肺障害を起こす．家畜類に対する去痰(たん)剤として用いられる．
説明
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.
定義
ChEBI: A pyrrolizidine alkaloid isolated from the plant species of the genus Senecio.
安全性プロファイル
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.
参考文献
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)
12-ヒドロキシセネシオナン-11,16-ジオン 上流と下流の製品情報
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