PEROXIDATION IN POSITION C-6 OF PROGESTERONE-3-ETHANOLIMINE IS INCREASED BY THE PRESENCE OF ENZYMES GENERATING OXYGEN RADICALS

被引:3
作者
ERIKSSON, CG
ENEROTH, P
机构
[1] Department of Clinical Chemistry and Blood Coagulation, Karolinska Hospital, Stockholm
[2] Unit for Applied Biochemistry, The Clinical Research Centre, Huddinge Hospital, Huddinge
关键词
STEROIDS; PEROXIDATION; PROGESTERONE-3-IMINE; ANDROSTENEDIONE-3-IMINE;
D O I
10.1016/0039-128X(90)90061-F
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The generation of 6-oxygenated (6-beta-hydroxy, 6-beta-hydroperoxy, and 6-oxo) progesterone derivatives during the hydrolysis of progesterone-3-ethanolimine has been shown to be increased in the presence of xanthine/xanthine oxidase. The combination of xanthine/xanthine oxidase with other enzymes and/or reagents that catalyze transformation (or formation) of oxygen radicals suggested that the most likely oxygen species participating in the 6-oxygenation was the protonated acid of the superoxide anion, i.e., the hydroperoxy radical. The suggestion was further supported by experiments with oxygen scavengers. However, the data presented do not rule out a radical propagation reaction since the steroid compound used may be more reactive than the scavengers tested. A stimulation of 6-oxygenation of progesterone-3-ethanolimine by NADPH-supplemented rat liver microsomes was found. This reaction was inhibited by the only oxygen scavenger (reduced glutathione) found to be effective in the xanthine/xanthine oxidase experiments. The similarities between the two oxygenation systems may implicate a mechanism for 6-beta-hydroperoxidation of 3-oxo-4-ene steroids in rat liver microsomes.
引用
收藏
页码:366 / 372
页数:7
相关论文
共 26 条
[1]  
Smith, Teng, Mechanism of microsomal lipid sterol metabolism XXIX. On the peroxidation in rat liver, J Am Chem Soc, 96, pp. 2640-2647, (1974)
[2]  
Smith, Teng, Lin, Seitz, McGehee, Lipid peroxidations of cholesterol, Lipid Peroxides in Biology and Medicine, pp. 89-105, (1982)
[3]  
Yu, Tan, Formation of 6β-hydroperoxyprogester-one in rat liver microsomes, Journal of Steroid Biochemistry, 17, pp. 89-94, (1982)
[4]  
Yu, Tan, Synthesis and properties of two new steroid hydroperoxides
[5]  
an alternative pathway for the formation of 6β-hydroxyprogesterone, Journal of Steroid Biochemistry, 8, pp. 825-834, (1977)
[6]  
Eriksson, Eneroth, Nordstrom, 6-Oxygenation of 3-oxo-4-ene steroids in high yields after 3-imine formation, Journal of Steroid Biochemistry, 22, pp. 549-655, (1985)
[7]  
Tien, Aust, Comparative aspects of several model lipid peroxidation systems, Lipid Peroxides in Biology and Medicine, pp. 23-39, (1982)
[8]  
Ambruso, Johnston, Lactoferrin enhances hydroxy radical production by human neutrophils, neutrophil particulate fractions and an enzymatic generating system, J Clin Invest, 67, pp. 352-360, (1981)
[9]  
Eriksson, Bergman, Eneroth, Nordstrom, Formation of inline derivatives between biologically occurring amines and oxo-steroids, J Steroid Biochem, 21, pp. 643-651, (1984)
[10]  
Eriksson, Eneroth, Nordstrom, Formation of imine derivatives between tris(hydroxymethyl)-amino-methane and saturated 3-oxo steroids during conventional work up of biological samples dissolved in Tris-HCl buffers, J Steroid Biochem, 19, pp. 1199-1203, (1983)