Studies on structure-activity relationship of gossypol, gossypol ethers and three naptaldehydes in the inhibition of spermatozoal metabolism
| Autor: | T. Krusius, J. Puranen, R. Sinervirta, Karri Wichmann, J. Jänne |
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| Rok vydání: | 1986 |
| Předmět: |
Male
Ether Fructose Naphthalenes Biology Spermatocidal Agents 010402 general chemistry 01 natural sciences Aldehyde Structure-Activity Relationship chemistry.chemical_compound Humans Structure–activity relationship chemistry.chemical_classification Aldehydes 010405 organic chemistry Gossypol Obstetrics and Gynecology Metabolism Spermatozoa Tautomer Sperm 0104 chemical sciences Reproductive Medicine chemistry Biochemistry Fructolysis Energy Metabolism |
| Zdroj: | Contraception. 33:519-528 |
| ISSN: | 0010-7824 |
| DOI: | 10.1016/s0010-7824(86)80010-5 |
| Popis: | Gossypol tetramethyl ether [C 30 H 24 O 2 (OCH 3 ) 4 ]and gossypol hexamethyl ether [C 30 H 24 O 2 (OCH 3 ) 6 ], which in contrast to gossypol are stable compounds, were tested for their ability to depress fructose degradation in fresh human sperm cells. Both ethers inhibited spermatozoal fructolysis, yet less effectively than did the parent compound. A synthetic compound, O-hydroxylnaphtaldehyde, and two commercially available preparations, 1- and 2-naphtaldehydes, were also tested under the same experimental conditions. These preparations represent about half of the gossypol molecule and possess a reactive aldehyde group in their molecules. Their inhibitory effect on fructose degradation in fresh human sperm cells, however, was considerably smaller than that of gossypol itself. It thus appears that the whole ring structure of gossypol rather than the intact aldehyde group is required for an effective inhibition of spermatozoal energy metabolism. |
| Databáze: | OpenAIRE |
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