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Formation of Methylhydrazine from Acetaldehyde /V-Methyl-A/- Formylhydrazone, a Component of Gyromitra Esculenta ^

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Formation of Methylhydrazine from Acetaldehyde /V-Methyl-A/- Formylhydrazone, a Component of Gyromitra Esculenta ^ [CANCER RESEARCH 37, 3458-3460, September 1977] Brief Communication Formation of Methylhydrazine from Acetaldehyde /V-Methyl-A/- formylhydrazone, a Component of Gyromitra esculenta ^ Donald Nagel, L. Wallcave, Bela Toth, and Robert Kupper The Eppley Institute for Research in Cancer, University of Nebraska Medical Center, Omaha, Nebraska 68105 SUMMARY recently been confirmed at levels of 0.3% gyromitrin and 0.05% MFH in the dried mushrooms (14). Gyromitrin, acetaldehyde /V-methyl-N-formylhydrazone, An earlier study indicated that, MH, a known tumorigen is a toxin present in edible wild mushroom Gyromitra escu producing lung tumors in mice (17) and malignant histiocy- lenta. At 37°under different acidic conditions (pH 1 to 3), tomas and tumors of the cecum in hamsters (20), was mimicking the milieu of human stomach, gyromitrin is con formed from either gyromitrin or MFH by treatment with verted to methylhydrazine, a known tumor inducer in mice strong acid (11). The present study was undertaken to de and hamsters, through an intermediate, /v-methyl-/V-formyl- termine whether MH could be formed under pH conditions hydrazine. In addition, methylhydrazine is formed in the simulating the milieu of the human stomach and to attempt mouse stomach after p.o. administration of gyromitrin. an in vivo demonstration of its formation from gyromitrin in These findings imply that consumption of G. esculenta the mouse stomach. could present a carcinogenic, as well as an acutely toxic, health hazard. MATERIALS AND METHODS INTRODUCTION MH was purchased from Eastman Kodak Co., Rochester, N. Y. MFH was prepared by a modification of the original Gyromitra esculenta, false morel (a wild edible mush method (9) from MH and methyl formate in ethanol at -15°. room), grows in sandy soil under conifer trees in Europe, Gyromitrin was prepared from MFH and acetaldehyde in North America, and elsewhere (12, 13). It is collected and diethyl ether, as previously described (9). eaten on a considerable scale in Michigan, Idaho, Colo 1-Methyl-1[(2-nitrophenyl)methylene]diazane (2-nitro- rado, and North Carolina. Gourment shops in the United benzaldehyde methylhydrazone) was prepared by refluxing States also stock a variety canned in Europe (15). 3.0 g of nitrobenzaldehyde and 1.0 g of MH in 50 ml of G. esulenta is widely consumed, and over 500 poisonings methanol for 2 hr. Evaporation of the solvent left a red oil, resulting from its ingestion are documented in the literature which crystallized on standing in the cold. Recrystallization (4). Seventy-four of the poisoning were fatal (2, 5, 6). Fatal from ether-hexane gave bright orange-yellow needles, m.p. poisoning is obviously infrequent on a percentage basis, 39-40°[from the literature, 37-39°(8)]. The spectral charac and this is undoubtedly a result of the almost universal teristics (IR, UV, PMR, CMR) of these compounds were practice of boiling the mushroom a long time in a large consistent with the assigned structures. quantity of water and then discarding the liquid (15). Never PMR spectra were determined in D.,0 or CDCI;, solutions theless, fatalities have been reported in people who ate this on a Varian Model HA-100 nuclear magnetic resonance mushroom after cooking it and discarding the juice (7, 21, spectrometer, CMR spectra were determined on a Varian 22). Model CFT-20 spectrometer, IR spectra were determined on In G. esculenta the toxin was originally identified as hel- a Beckman Model IR-9 spectrophotometer, and UV spectra velic acid, but this was later found to be a mixture of fatty were determined on a Gary Model 14 spectrophotometer. acids (1). Recently, in a series of papers (9-11 ), 2 hydrazine GLC determinations of gyromitrin were performed on a derivatives (a hydrazone, acetaldehyde A/-methyl-/V-for- Beckman Model GC-45 Chromatograph with the use of 2-m mylhydrazone, which was termed gyromitrin, and a hydra- x 2-mm glass column of Chromosorb 103 (Supelco, Inc., zide, MFH2) were identified as toxins in this fungus. The Bellefonte, Pa.) (column temperature, 160°;helium flow latter structure was postulated as a hydrolysis product of rate, 20 ml/min). Under these conditions the retention gyromitrin. The presence of these hydrazine derivatives has time of gyromitrin was 17.0 min, and that of MFH was 15.7 min. GLC determinations of 1-methyl-2-[(2-nitro- ' Research supported by USPHS Contract 1 CP33278 from the National phenyl)methylene]diazene were performed on a Varian Cancer Institute, NIH. Model 3700 gas Chromatograph with the use of a 2-m x 2- 2 The abbreviations used are: MFH, A/-methyl-W-formylhydrazine; MH, mm glass column packed with 8% SE-30 on 100/120 mesh methylhydrazine; PMR, proton magnetic resonance; CMR, carbon magnetic Chromasorb W AW-DMCS (column temperature, 160°;he resonance; GLC, gas-liquid chromatography or Chromatograph. Received August 23, 1976; accepted June 21, 1977. lium flow, 20 ml/min). Under these conditions the retention 3458 CANCER RESEARCH VOL. 37 Downloaded from cancerres.aacrjournals.org on September 25, 2021. © 1977 American Association for Cancer Research. Gyromitrin Hydrolysis time of the hydrazone was 7.25 min and that of 2-nitrobenz- the blanks, there did not appear to be a correlation between aldehyde was 1.4 min. the time and the amount of MH present. The kinetic studies were conducted at 37°in potassium Product studies conducted in vitro at pH 1 indicated that chloride-hydrochloric acid buffer (pH 2) or potassium hy gyromitrin was converted to MFH, which in turn was hydrol- drogen phthalate-hydrochloric acid buffer (pH 2.5 and 3.0). ized to MH, as illustrated in Chart 1. The products were Aliquots of the gyromitrin-buffer mixture were taken at characterized by GLC, PMR, and CMR with the aid of au specified intervals, neutralized to pH 8 with 1.5 N sodium thentic synthetic compounds. No other products were no hydroxide, and injected on the GLC. The rate of reaction ticed. was monitored by integration of the gyromitrin and MFH At pH 2 at 37°,gyromitrin at an initial concentration of 1.0 peak areas. x 10~3M was hydrolyzed to MH with a half-life of 122 min, as The molar concentrations of gyromitrin and MFH were illustrated in Chart 2. At pH 2.5 the half-life for the formation calculated with the response from standard samples. The of MH was 10.5 hr, whereas at pH 3.0 only 9.0% MH was amount of MH formed at time f, [MHt], was calculated with produced in 72 hr. the formula: [MH,] = [G„]-[Gt] - [MFH,] DISCUSSION where [G„]isthe initial concentration of gyromitrin. These studies showed that MH was produced by acid For determination of the extent of MH formation from hydrolysis from gyromitrin through MFH. As would be ex gyromitrin in the mouse stomach, female Swiss mice from pected from the chemistry of hydrazones and hydrazides, the Eppley Institute colony, 10 weeks old, were fasted for 24 the rate of hydrolysis was strongly pH dependent (16). hr and given 4.0 mg of gyromitrin in 0.5 ml of distilled water MH formation was monitored by measuring the disap intragastrically. After the specified times, the animals were pearance of gyromitrin and MFH rather than the formation killed, the abdominal wall was incised, and the esophagus of MH, since the GLC of MH directly from aqueous solutions was ligated. The stomach was removed and slit, and the gave poorly reproducible results due to decomposition dur contents were gently scraped out. The inner surface was ing chromatography. washed with distilled water, and a combined volume of For determination of MH in the in vivo mouse experi about 4 ml was collected. After determination of the pH of ments, it was, of course, essential to measure MH in a more the stomach contents, 0.14 ml of 5.0 M potassium acetate Table 1 was added, followed by sufficient 5 M HCI (usually 0.04 MH in mouse stomach after p.o. administration of 4.0 mg of ml) to give a pH of 5.3 to 5.7. The buffered stomach sus gyromitrin pension was centrifuged, and the supernatant was trans Time(min)0153045120240MH"(/*g)0.42.55.511.05.06.08.010.512.06.06.57.0StomachpHND"2.42.45.62.93.52.22.24.24.83.6 ferred to a 2nd graduated centrifuge tube. The precipi tate was rinsed with about 1 ml of water. The combined volume was diluted, if necessary, to 5.0 ml, and 1.0 ml of a 0.6% solution of 2-nitrobenzaldehyde in methanol was added. The stoppered tube was kept in a bath at 50°for 30 min in the dark. One ml of carbon disulfide was added to the cooled mixture, and the contents were vigorously shaken for 1 min. After centrifugaron to break an emulsion, 3.0 /¿I of organic phase were used for GLC determination of 1- methyl-2-[(2-nitrophenyl)methylene]diazane. A calibration curve was prepared by adding measured quantities of MH, from 2.0 to 21.0 ¿tg,to5.0 ml of buffer at pH 5.5 and treating " Amount of MH found in 4 mg of gyromitrin in 0.5 ml of water. the solution with 2-nitrobenzaldehyde, as described. Simi Average of 3 determinations. Each value represents a single ani mal. larly, blanks were prepared from the reaction of 4.0 mg of * ND, not determined. gyromitrin in 5.0 ml of buffer with 2-nitrobenzaldehyde. At an electrometer setting of 4 x 10~" /ua, full-scale recorder CH, .CH, deflection was obtained with about 30 /^.gof hydrazine. The GYROMITRIN solution of the hydrazone in carbon disulfide was stable in HC the dark for 24 hr.
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