Zusammenfassung
Gereinigtes Agaritin [N′-(γ-L(+)glutamyl)-p-hydroxymethylphenylhydrazin]; (ein im ZuchtchampignonAgaricus bisporus vorkommender Inhaltsstoff),p-Hydrazinobenzoesaure (eine hypothetische Vorstufe von Agaritin) sowie einige Abbauprodukte von Agaritin wurden mit Hilfe desSalmonella/Säuger-Mikrosomen-Tests (Ames Test) auf mutagene Aktivität untersucht. In Übereinstimmung mit Literaturdaten zeigte Agaritin eine deutliche direkt wirkende mutagene Aktivitat mitSalmonella typhimurium TA1537 (30 Revertanten/gmol) and TA97. Inkubation von Agaritin bei alkalischem pH führte zu einem pH-abhangigen Anstieg der Mutagenität. Inkubation von Agaritin mitγ-Glutamyltransferase (GT) während 10 h (Zimmertemperatur; pH 8.2) führte sogar zu einer 8- bis 16 fachen Zunahme der Mutagenität. Synthetischesp-Hydroxymethylphenylhydrazin (das vermutliche Produkt des durch die GT katalysierten Abbaus von Agaritin) zeigte allerdings eine nur etwa 3- bis 6 mal höhere mutagene Aktivität als Agaritin. Das hypothetische ultimate Mutagen, das Hydroxymethyldiazonium-Ion, welches auch inA. bisporus vorkommt, zeigte die höchste Mutagenität (TA1537: ca. 300 bis 1000 Revertanten/gmol).
Summary
Purified agaritine (N′-(γ-L(+)-glutamyl)-p-hydroxymethylphenylhydrazine) isolated fromAgaricus bisporus,p-hydrazinobenzoic acid (its presumptive precursor) and some agaritine-degradation products were tested for mutagenic activity with theSalmonella/mammalian microsome assay (Ames test). Consistent with the literature, agaritine showed a distinct direct-acting mutagenicity with the strain TA1537 (30 revertants/gmol) and with TA97. Incubation of agaritine at alkaline pH increased the mutagenic effect. Pre-incubation of agaritine with γ-glutamyl transferase (GT) during 10 h at room temperature (pH 8.2) even enhanced the mutagenicity by a factor of 8 to 16 depending on the strain. In accordance with this finding, syntheticp-hydroxymethylphenylhydrazine (the presumptive product of the GT catalyzed degradation) showed also a distinct direct-acting mutagenicity, but the increase was only about 3- to 6-times compared with agaritine. The hypothetical ultimate mutagenic metabolite of agaritine, thep-hydroxymethylbenzenediazonium ion, a compound occuring naturally inA. bisporus, showed the highest mutagenic activity (with TA1537 approximately 300 to 1000 revertants/μol).
Article PDF
Explore related subjects
Discover the latest articles, news and stories from top researchers in related subjects.Avoid common mistakes on your manuscript.
References
Toth B (1975) Cancer Res 35:3693
Levenberg B (1964) J Biol Chem 239:2267
Lawson T, and Toth B (1983) Proc Am Assoc Cancer Res 24:77
Toth B, Nagel D, Patil K, Erickson J, Antonson K (1979) Cancer Res 38:177
Toth B (1979) J Toxicol Environ Health 5:193
Toth B, Tompa A, Patil K (1977) Z Krebsforsch Klin Onkol 89:245
Toth B, Patil K, Jae HS (1981) Cancer Res 41:2444
Toth B, Raha CR, Wallcave L, Nagel D (1981) Anticancer Res 1:255
Rogan EG, Walker BA, Gingell R, Nagel D, Toth B (1982) Mutat Res 102:413
Toth B, Nagel D, Shimizu H, Somson H, Issenberg P, Erickson J (1975) Proc Am Assoc Cancer Res 16:61
Sterner O, Bergman R, Kesler E, Magnusson G, Nilsson L, Wickberg B, Zimerson E (1982) Mutat Res 101:269
Ames BN, McCann J, Yamasaki E (1975) Mutat Res 31:347
Yahagi T, Nagao M, Seino Y, Matsushima T, Sugimura T, Okada M (1977) Mutat Res 48:121
Ames BN, Lee FD, Durston WE (1973) Proc Natl Acad Sci USA 70:782
McCann J, Choi E, Yamasaki E, Ames BN (1975) Proc Natl Acad Sci USA 72:5135
Toth B, Malick L, Shimizu H (1976) Am J Pathol 84:69
Parodi S, DeFlora S, Cavanna M, Pino A, Robbiani L, Bennicelli C, Brambilla G (1981) Cancer Res 41:1469
DeFlora S (1981) Carcinogenesis 2:283
Innes JRM et al (1969) J Natl Cancer Inst 42:1101
Shimizu H, Hayashi K, Takemura N (1978) Jpn J Hyg 33:474
Fischer B, Lüthy J, Schlatter Ch (1984) Z Lebensmittel Unters Forsch 179:218
Stark AA, Giroux CN (1982) Mutat Res 106:195
Fischer B (in preparation) Thesis ETH Zürich
Ross AE, Nagel DL, Toth B (1982) J Agric Food Chem 30:521
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Fredrich, U., Fischer, B., Lüthy, J. et al. The mutagenic activity of agaritine — a constituent of the cultivated mushroomAgaricus bisporus —and its derivatives detected with the Salmonella/mammalian microsome assay (Ames Test). Z Lebensm Unters Forch 183, 85–89 (1986). https://doi.org/10.1007/BF01041921
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF01041921