Weiser H, Kormann A W
Int J Vitam Nutr Res. 1983;53(2):143-55.
Relative antihemorrhagic properties of structural analogs of transphylloquinone (vitamin K1) have been determined by curative prothrombin time tests with vitamin K-deficient chicks. Analogs (where applicable) and the phylloquinone standard had (all-) rac-trans configuration, and all compounds were well characterized (structure, purity, trans: cis). Compounds were administered as single oral doses according to the up-and-down procedure. Estimation of mean effective doses allowed a reliable calculation of relative activities for analogs in comparison with vitamin K1 standard. 2', 3'-Dihydro-phylloquinone had a relative activity of only 6.7%, i.e. it was about 15 times less active than phylloquinone. Further reduction of this analog led to 2',3',5,6,7,8-hexahydro-phylloquinone which was completely inactive. Analogs with oxygen functions in the side chain, 6'-hydroxy-K1, 6'-oxo-K1, and 7'-hydroxy-6'-oxo-K1, displayed relative activities of 20.5%, 31.9%, and 30.5%, respectively. Phylloquinone-2,3-epoxide was 1.7 times more active than the phylloquinone standard. An analog with a 7-carbon side chain ending with a carboxy group (in mammals a urinary metabolite of vitamin K1) and its corresponding ethyl ester derivative were practically inactive.
通过对维生素K缺乏的雏鸡进行凝血酶原时间治疗试验，测定了反式叶绿醌（维生素K1）结构类似物的相对抗出血特性。类似物（如适用）和叶绿醌标准品具有（全）消旋反式构型，所有化合物均得到了充分表征（结构、纯度、反式：顺式）。化合物按照序贯法以单次口服剂量给药。通过估计平均有效剂量，可以可靠地计算出类似物相对于维生素K1标准品的相对活性。2',3'-二氢叶绿醌的相对活性仅为6.7%，即其活性约为叶绿醌的15分之一。该类似物的进一步还原产物2',3',5,6,7,8-六氢叶绿醌完全无活性。侧链带有氧官能团的类似物，6'-羟基-K1、6'-氧代-K1和7'-羟基-6'-氧代-K1，相对活性分别为20.5%、31.9%和30.5%。叶绿醌-2,3-环氧化物的活性比叶绿醌标准品高1.7倍。一种带有以羧基结尾的7碳侧链的类似物（在哺乳动物中是维生素K1的尿液代谢产物）及其相应的乙酯衍生物几乎没有活性。
