サンギナリン 化学特性,用途語,生産方法
解説
C20H15NO5(349.34)．サンギナリンは，ケシ科Sanguinaria canadensis，あるいはStrylophorum diphyllumなどの根に含有されるベルベリン型イソキノリンアルカロイド．融点266 ℃(分解)．水に不溶，エタノール，アセトン，クロロホルムに可溶．ベルベリンと同様な互変異性をもつと考えられ，遊離塩基は無色であるが，酸に溶けて赤色(四級塩型)となる．抗菌性，消炎鎮痛作用があるので，歯磨き粉や口腔のうがいに用いられる．LD50 19.4 mg/kg(ネズミ，皮下)．森北出版「化学辞典（第2版）
説明
A naphthoisoquinoline alkaloid, this base occurs in the roots of Chelidonium majus L., Glaucium fimbrilligerum and Sanguinaria canadensis L. The alkaloid was stated by Schmidt, Konig and Tietz to crystallize from EtOH or AcOEt as colourless needles, m.p. 213°C but this low melting point was found to be due to the presence of chelerythrine as an impurity. Once this is removed as the pseudocyanide, the base crystallizes from Et
20 and has the above melting point or 242-3°C on slow heating. Obtained from EtOH it forms the alcoholate, m.p. 195-7°C. The hydrochloride forms long, slender, bloodred needles. On distillation with Zn dust, the alkaloid furnishes a-naphthaphenanthridine and the structure given above has been further confirmed by synthesis.
使用
Sanguinarium induces HO-1 expression thus inhibiting MMP-9 and COX-2 expression in TPA-induced breast cancer cells.
定義
Sanguinarine is a benzophenanthridine alkaloid derived from the root of Sanguinaria canadendid. Limited available evidence indicates that it may be used to prevent and treat UV-induced
skin damage. Specifically, topical application of sanguinarine on the skin of SKH-1 hairless mice before or after UVB irradiation resulted in significantly lower UVB-mediated skin edema, skin hyperplasia and
infiltration of leukocytes, and markers of oxidative stress (e.g., H2O2).
参考文献
Dana., Mag. Pharm., 23, 125 (1829)
Bruchhausen, Bersch., Ber., 63, 2520 (1930)
Spath, Kuffner., ibid, 64, 370, 1123, 2034 (1931)
Synthesis:
Dyke, Moon, Sainsbury., Tetrahedron Lett., 3933 (1968)
サンギナリン 上流と下流の製品情報
原材料
準備製品