Production of (S)-3-chlorolactaldehyde from (S)-alpha-chlorohydrin by boar spermatozoa and the inhibition of glyceraldehyde 3-phosphate dehydrogenase in vitro.
The (S)-isomer of the male antifertility agent alpha-chlorohydrin was metabolized by mature boar spermatozoa in vitro to (S)-3-chlorolactaldehyde. This oxidative process, which did not occur when (R)-alpha-chlorohydrin was offered as a substrate, was catalysed by an NADP+-dependent dehydrogenase that converts glycerol to glyceraldehyde. (S)-3-chlorolactaldehyde, produced by this metabolic reaction or when added to suspensions of boar spermatozoa, was a specific inhibitor of glyceraldehyde 3-phosphate dehydrogenase as assessed by the accumulation of fructose 1,6-bisphosphate and the triosephosphates. When glycerol and (S)-alpha-chlorohydrin were added concomitantly to boar spermatozoa in vitro, the presence of glycerol decreased the degree of inhibition of glyceraldehyde 3-phosphate dehydrogenase. Extracts of glyceraldehyde 3-phosphate dehydrogenase that were obtained from boar spermatozoa incubated with (S)-alpha-chlorohydrin or (R,S)-3-chlorolactaldehyde showed significant reductions in their enzymic activity.
D000447:Aldehydes / Q000096:biosynthesis*; D000818:Animals; D002728:Chlorohydrins / Q000378:metabolism*; D003864:Depression, Chemical; D005987:Glyceraldehyde-3-Phosphate Dehydrogenases / Q000378:metabolism*; D005990:Glycerol / Q000494:pharmacology; D066298:In Vitro Techniques; D007536:Isomerism; D008297:Male; D010084:Oxidation-Reduction; D013094:Spermatozoa / Q000187:drug effects / Q000201:enzymology / Q000378:metabolism*; D013552:Swine; D000517:alpha-Chlorohydrin / Q000378:metabolism* / Q000494:pharmacology
D000447:Aldehydes; D002728:Chlorohydrins; C045799:3-chlorolactaldehyde; D000517:alpha-Chlorohydrin; D005987:Glyceraldehyde-3-Phosphate Dehydrogenases; D005990:Glycerol