Simple Compounds With Vitamin K Activity

Abstract

Communications to the Editor Vol. 61 substituted naphthoquinones. A positive color reaction for 2-hydroxy-1,4-naphthoquinones [ibid., 58, 1174 (1936)] was obtained with highly purified concentrates of vitamin K from alfalfa. The positions of ultraviolet absorption maxima reported in vitamin K concentrates, especially at 328 and 248 µ [Helv. Chim. Acta, 22, 310 (1939)], are close to the 334 and 250 maxima of phthiocol [/. Biol. Chern., 115, 479 (1936)], and the general shapes of the absorption curves are similar.We have made quantitative assays by our improved method [Biochem. J., in press] of phthiocol and several related compounds. In addition to the substances listed in Table I,we have tested lapachol and lomatiol. Both of these proved inactive, first at a 20-mg. level and later at a 100-mg. level. A preliminary test of a preparation of phthiocol monoacetate indicated a greater degree of activity than that of phthiocol.An aqueous solution of phthiocol was made by dissolving 2 mg. in each cc. of a 0.05 molal phosphate buffer, pH 7.4. The pH of the final solution was 7.0. Sufficient of this solution was injected daily into the breast muscle of chicks to equal the amount consumed by chicks on the 20-mg. level. A control group received the same amount of solution orally. The average prothrombin time for 6 injected chicks was 31.9 seconds, while that for 6 orally fed chicks was 32.4 seconds. An 0.05 molal phosphate buffer, pH 7.8, dissolved 4 mg. of phthiocol per cc. to a final pH of 7.1. Chicks receiving no vitamin K in the diet were given intravenously 2 mg. each of phthiocol in aqueous solution. A comparable group of chicks was

A Vitamin K Analogue in Obstructive Jaundice

“…The methods of biological test used did not differ substantially from those described by a number of previous investigators (Schonheyder, 1936;Almquist and Stokstad, 1937;Ansbacher, 1939;Thayer et al, 1938), and we would only call attention to certain points of technique, some of which constitute minor modifications in this type of work and may be of interest.…”

“…In other words, the test has a high inherent error, due both to high variance of the animals in a test group and also to variations in the slope of the dosage/response curve. Although a number of workers have published particulars of tests carried out at various dose levels (notably Ansbacher, 1939, andThayer et al, 1939c), such publications have not always included adequate statistical analysis of the results.…”

Vitamin K.

“…These include phthiocol (13,18,29,72,79,181), 3,4dihydroxy-1 ,2-naphthoquinone (134), 2-allyl-3-hydroxy-1 ,4-naphthoquinone (134), 2-n-butyl-3-hydroxy-1,4-naphthoquinone (134), a-lapachone (80,134), lapachol (14,80,82,85,133), lomatiol (14,80,82), hydrolapachol (15,80,82), phthiocol ethyl ether (15), phthiocol octadecyl ether (15)) phthiocol phytyl ether (15), dihydrophthiocol triacetate (15) (83), and p , /3-dimethyldihydrofurano-1 ,4-naphthoquinone (134). These include phthiocol (13,18,29,72,79,181), 3,4dihydroxy-1 ,2-naphthoquinone (134), 2-allyl-3-hydroxy-1 ,4-naphthoquinone (134), 2-n-butyl-3-hydroxy-1,4-naphthoquinone (134), a-lapachone (80,134), lapachol (14,80,82,85,133), lomatiol (14,80,82), hydrolapachol (15,80,82), phthiocol ethyl ether (15), phthiocol octadecyl ether (15)) phthiocol phytyl ether …”

Contribution a l’étude de quelques mycobactéries: metabolites et antibiotiques

“…L'intérêt de ces 2 corps réside dans le fait qu'ils sont voisins de la vitamine K par leurs propriétés physiques et chimiques et qu'ils présentent, comme elle, un pouvoir antihémorragique (14,15,16,17,18,19).…”