Wiegrebe W, Gerber A, Kappler J, Bayerl C
Arzneimittelforschung. 1979;29(8):1083-8.
The metabolisation of the antipsoriatically active molecules 1,8,9-triacetoxy-anthracene und 1,8-diacetoxy-9-anthrone by serum is described. Under these conditions 1,8-dihydroxy-9-anthrone, 1-hydroxy-8-acetoxy-9-anthrone, 1,8,1',8'-tetrahydroxy-bisanthrone, 1,8-dihyroxy-anthraquinone, 1,8-diacetoxy-anthraquinone and 1-hydroxy-8-acetoxy-anthraquinone arise from both educts. Quantitative determinations of these metabolites indicate that hydrolytic reactions occur prior to oxidation. Contrary to 1,8-dihydroxy-9-anthrone, 1,8,9-triacetoxyanthracene and 1,8-diacetoxy-9-anthrone are effective against psoriatic lesions without accompanying inflammations of the skin. 1,8,9-Trimethoxy-anthracene, however, is ineffective, also indicating that at least 1,8,9-triacetoxy-anthracene is a prodrug.--In agreement with Krebs' hypothesis 10,10-dialkylated 1,8-dihydroxy-9-anthrones described in this paper are ineffective against psoriasis.
描述了血清对具有抗银屑病活性的分子1,8,9 - 三乙酰氧基蒽和1,8 - 二乙酰氧基 - 9 - 蒽酮的代谢作用。在这些条件下，两种起始物质都会生成1,8 - 二羟基 - 9 - 蒽酮、1 - 羟基 - 8 - 乙酰氧基 - 9 - 蒽酮、1,8,1',8' - 四羟基 - 双蒽酮、1,8 - 二羟基 - 蒽醌、1,8 - 二乙酰氧基 - 蒽醌和1 - 羟基 - 8 - 乙酰氧基 - 蒽醌。对这些代谢产物的定量测定表明，水解反应先于氧化反应发生。与1,8 - 二羟基 - 9 - 蒽酮不同，1,8,9 - 三乙酰氧基蒽和1,8 - 二乙酰氧基 - 9 - 蒽酮对银屑病皮损有效且不会伴随皮肤炎症。然而，1,8,9 - 三甲氧基蒽无效，这也表明至少1,8,9 - 三乙酰氧基蒽是一种前药。——与克雷布斯假说一致，本文所述的10,10 - 二烷基化1,8 - 二羟基 - 9 - 蒽酮对银屑病无效。
