On the basis of recent observations it is supposed that seminal fluids may contain — mainly in hydroxymethyl groups — formaldehyde (HCHO) and quaternary ammonium compounds as potential HCHO generators, therefore, preliminary investigations were carried out for the identification of these compounds in pig seminal fluids using OPLC, HPLC and MALDI MS techniques. The fresh pig seminal fluid was frozen in liquid nitrogen, powdered and aliquots (0.25 g) were treated with 0.7 ml ethanolic dimedone solution. The suspension was centrifuged and the clear supernatant was used for analysis by OPLC or after dilution with HPLC or MALDI MS technique. After OPLC separation of formaldemethone the fully N-methylated compounds which are stayed on the start point were separated by OPLC using an other eluent system. It has been established that the HCHO is really a normal component of the pig seminal fluid, as well. It can be isolated and identified in dimedone adduct form. The measurable amount of HCHO depended on the concentration applied of dimedone. According to OPLC and MALDI MS investigations L-carnitine is the main quaternary ammonium compound in pig seminal fluid which can generate a protection of the sperm cells against environmental and other influences. Considerable differences have been found among individuals concerning concentrations of quaternary ammonium compounds in the seminal fluid of pigs.
Chelvarajan, R. L., Fannin, F. F., Bush, L. P. (1993) Study on nicotine demethylation in Nicotiana otophora. J. Agric. Food Chem. 41, 858–862.
Huszti, S., Tyihák, E. (1986) Formation of formaldehyde from S-adenosyl-L-(methyl-3H) methionine during enzymatic transmethylation of histamine. FEBS Letters 209, 362–366.
Kalász, H. (2003) Biological role of formaldehyde, and cycles related to methylation, demethylation and formaldehyde production. Med. Chem. Mini Rev. 3, 175–192.
Lenzi, A., Lombardo, F., Gandini, L., Dondero, F. (1992) Metabolism and action of L-carnitine: its possible role in sperm tail function. Arch. Ital. Urol. Nefrol. Androl. 64, 187–196.
Majumder, P. K., Kumar, V. L. (1995) Inhibitory effects of formaldehyde on the reproductive system of male rats. Indian J. Physiol. Pharmacol. 39, 80–82.
Mazzuca, S., Bitonti, M. B., Innocenti, A. M., Francis, D. (2000) Inactivation of DNA replication origins by the cell cycle regulator, trigonelline, in root meristems of Lactuca sativa. Planta 35, 127–132.
Mishkinsky, J., Joseph, B., Sulman, F. G. (1967) Hypoglycaemic effect of trigonelline. Lancet 35, 1311–1312.
Odeigah, P. G. (1997) Sperm head abnormalities and dominant lethal effects of formaldehyde in albino rats. Mutat. Res. 389, 141–148.
Rétfalvi, T., Németh, Zs., Sarudi, I., Albert, L. (1998) Alteration of endogenous formaldehyde level following mercury accumulation in different pig tissues. Acta Biol. Hung. 49, 375–379.
Rozylo, T. K., Siembida, R., Nemeth, Zs. I., Albert, L., Tyihak, E. (2000) HPLC-OPLC-MS investigation of change of formaldehyde and its generators in human teeth of different physiological stage. Biomed. Chromatogr. 14, 173–179.
Sárdi, É., Tyihák, E. (1998) Relationship between dimedone conventration and formaldehyde captured in plant tissues. Acta Biol. Hung. 49, 291–301.
Sinclair, S. (2000) Male infertility: nutritional and environmental considerations. Altern. Med. Rev. 5, 28–38.
Szende, B., Tyihák, E., Szókán, Gy., Kátay, Gy. (1995) Possible role of formaldehyde in the apoptotic and mitotic effect of 1-methyl-ascorbigen. Path. Oncol. Res. 1, 38–42.
Szende, B., Tyihák, E., Trézl, L., Szoke, É., László, I., Kátay, Gy., Király-Véghely, Zs. (1998) Formaldehyde generators and capturers as influencing factors of mitotic and apoptotic processes. Acta Biol. Hung. 49, 323–329.
Szilágyi, M. (1998): L-Carnitine as essential methylated compound in animal metabolism. Acta Biol. Hung. 49, 209–218.
Trézl, L., Pipek, J. (1988) Formation of excited formaldehyde in model reactions simulating real biological systems. J. Mol. Struct. (Theochem) 170, 213–223.
Tyihák, E. (1987) Overpressured layer chromatographic methods in the study of the formaldehyde cycle in biological systems. Trends Anal. Chem. 6, 90–94.
Tyihák, E., Albert, L., Németh, Zs. I., Kátay, Gy., Király-Véghely, Zs., Szende, B. (1998a) Formaldehyde cycle and the natural formaldehyde generators and capturers. Acta Biol. Hung. 35, 225–238.
Tyihák, E., Trézl, L., Szende, B. (1998b) Formaldehyde cycle, and the phases of stress syndrome. In: Csermely, P. (ed.) Stress of Life: from Molecules to Man. Ann. New York Acad. Sciences, 851, 259–270.
Wentworth, P. Jr., Nieva, J., Takeuchi, C., Galve, R., Wentworth, A. D., Dilley, R. B., CeLaria, G. A., Saven, A., Babior, B. M., Janda, K. D., Eschenmoser, A., Lerner, R. A. (2003) Evidence for ozone formation in human atherosclerotic arteries. Science 302, 1053–1056.
Yu, P. H. (1998) Increase of formation of methylamine and formaldehyde in vivo after administration of nicotine and the potential cytotoxicity. Neurochem. Res. 23, 1205–1210.
Zopfgen, A., Priem, F., Sudhoff, F., Jung, K., Lenk, S., Loening, S. A., Sinha, P. (2000) Relationship between semen quality and the seminal plasma components carnitine, alpha-glucosidase, fructose, citrate and granulocyte elastase in infertile men compared with a normal population. Hum. Reprod. 15, 840–845.
The skillful assistance of Mrs Edit Dobos-Harsányi is gratefully acknowledged.
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Szilágyi, M., Németh, Z.I., Albert, L. et al. Formaldehyde and Some Fully N-Methylated Substances in Boar Seminal Fluids. BIOLOGIA FUTURA 57, 133–136 (2006). https://doi.org/10.1556/ABiol.57.2006.1.13
- seminal fluid