ABSTRACT
The structures, properties, methods of chemical synthesis, and insect hormonal activities of insecticides of a new 1-alkyl-1,2-diacylhydrazine series are reviewed. They are agonists of ecdysteroids, insect molting hormones, in their action mechanism. The English version of the paper: Russian Journal of Bioorganic Chemistry, 2004, vol. 30, no. 6; see also http://www.maik.ru.
Subject(s)
Ecdysteroids/antagonists & inhibitors , Hydrazines/chemistry , Insecticides/chemistry , Animals , Hydrazines/chemical synthesis , Insecta/physiology , Insecticides/chemical synthesis , MoltingABSTRACT
Progesterone biotransformation with recombinant yeast Yarrowia lipolytica E129A15 and Saccharomyces cerevisiae GRF18/YEp5117 alpha expressing bovine adrenocortical cytochrome P45017 alpha yielded 17 alpha-hydroxyprogesterone and two diols, 17 alpha, 20 beta- and 17 alpha, 20 alpha-dihydroxypregn-4-en-3-one. The oxidation of mixtures of the three steroids with chromic acid resulted in the cleavage of 17-20 bonds in the diols with the formation of androst-4-ene-3,17-dione. The biotransformation of pregn-4-ene-20 beta-ol-3-one by means of Y. lipolytica E129A15 was accompanied by the following reactions: the primary oxidation of these compounds to progesterone and the subsequent successive reactions of 17 alpha-hydroxylation and 20 alpha- and 20 beta-reduction. The results widen the possibilities for enzymatic and chemical modifications of steroids. The English version of the paper: Russian Journal of Bioorganic Chemistry, 2003, vol. 29, no. 6; see also http://www.maik.ru.
Subject(s)
Pregnanes/chemistry , Progesterone/pharmacokinetics , Steroid 17-alpha-Hydroxylase/metabolism , Adrenal Cortex/enzymology , Animals , Biotransformation , Cattle , Oxidation-Reduction , Saccharomyces cerevisiae/genetics , Steroid 17-alpha-Hydroxylase/genetics , Yarrowia/geneticsABSTRACT
Although the involvement of 3-oxo-delta 4 compounds as intermediates in arthropod ecdysteroid biosynthesis has been postulated for a long time, it has not yet been directly demonstrated. In the present study, 3-oxo-delta 4-steroids have been synthesized and incubated in vitro with dissociated moulting gland cells from the crab Carcinus maenas. The tritiated compounds were converted into 3-dehydroecdysone, ecdysone and/or 25-deoxyecdysone, i.e. final ecdysteroids. This means that the 3-oxo-delta 4 compounds had undergone a 5 beta-reduction, to give the 5 beta-conformation of ecdysteroids. Our results suggest that the 3-oxo-delta 4-steroid 4,7-cholestadien-14 alpha-ol-3,6-dione may be an intermediate in the biosynthetic pathway. The 5 beta-reduction reaction involves a cytosolic enzyme which requires NADPH as electron donor and seems specific for 3-oxo-delta 4 substrates. This reaction was the most active in crab Y-organs, as compared with other tissues. The characteristics of the 5 beta-reductase (subcellular localization, substrate and cofactor requirements) appear similar to those of the vertebrate 3-oxo-delta 4-steroid 5 beta-reductase involved in steroid hormone catabolism and bile acid biosynthesis.
Subject(s)
Brachyura/metabolism , Insect Hormones/biosynthesis , Steroids/biosynthesis , Animals , Brachyura/growth & development , Chromatography, High Pressure Liquid , Ecdysteroids , Insect Hormones/chemistry , Ketosteroids/chemical synthesis , Ketosteroids/metabolism , Molecular Structure , Oxidation-Reduction , Radioisotope Dilution Technique , Steroids/chemistry , TritiumABSTRACT
It was shown that a phytosteroid ecdisterone which is the principle of a new tonic drug ecdisten in doses of 5-20 mg/kg is able to stimulate the primary immune reaction slightly effecting the indices of T-cell immunity activity and phagocyte functions. On increasing ecdisterone dose to 50 mg/kg inhibition of the number of antibody cells in the mouse spleen was marked.