Gyromitrin, das Gift der Frühjahrslorchel. 16. Mitt. über Pilzinhaltsstoffe

List, Paul Heinz; Luft, Petra

doi:10.1002/ardp.19683010410

Cited by 62 publications

(12 citation statements)

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“…Only two fungal metabolites have been reported, agaritine from the cultivated mushroom Agaricus bisporus 14 and gyromitrin from the false morel Gyromitra esculenta. 15 As far as we know, elaiomycins B (2) and C (3) are the first natural occurring alkylhydrazides with therapeutic potential as shown by their inhibitory activity against clinically relevant enzymes.…”

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confidence: 99%

Elaiomycins B and C, novel alkylhydrazides produced by Streptomyces sp. BK 190

et al. 2011

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Dereplicated novel actinomycetes from neglected habitats provide high quality biological material for screening programs designed to detect novel bioactive secondary metabolites. 2 Such organisms include neutrotolerant acidophilic streptomycetes which grow from pH 4.5 to 7.5, with an optimum between pH 5.0 and 5.5. 3 Members of this group were isolated from a hay meadow soil taken from Cockle Park Experimental Farm in Northumberland, UK. The isolates were grown as submerged cultures in complex media, and extracts from the culture filtrates and mycelia included in our HPLC-diode array screening program to detect novel secondary metabolites by means of an in-house HPLC-UV-Vis database, which contains approximately 950 natural products, mainly antibiotics. 4 Strain BK 190 was of interest because of the presence of three prominent peaks in the HPLC profile of a culture filtrate extract. The strain was assigned to the genus Streptomyces by its morphological and chemotaxonomic properties. 5 Strain BK 190 formed an extensively branched substrate mycelium, a grey aerial spore mass and aerial hyphae, which differentiated into spiral chains of smooth-surfaced spores on oatmeal agar, contained LL-diaminopimelic acid, galactose, glucose and xylose as major sugars, N-acetylated muramic acid, predominant amounts of hexa-and octa-hydrogenated menaquinones with nine isoprene units, and produced iso-and anteiso-branched fatty acids with C 15:0 and iso-C 16:0 as major components. The temperature and pH ranges for growth were 10-35 1C and pH 4.0-8.0, respectively. Phylogenetic analyses showed that the organism was most closely related to the type strain of Streptomyces sanglieri; the two organisms shared a 16S rRNA similarity of 99.9%, a value that corresponds to a single nucleotide difference at 1434 locations.The metabolite with retention time of 12.3 min in our standardized reversed-phase gradient elution profile was identified by HPLC-diode array and HPLC-ESI-MS analysis to be elaiomycin (1), an azoxy antibiotic that was first isolated from Streptomyces hepaticus and found to strongly inhibit the growth of Mycobacterium tuberculosis. 6 Two further prominent peaks, elaiomycin B (2) with a retention time of 16.4 min, and elaiomycin C (3) with a retention time of 17.2 min showed characteristic UV-vis spectra that differed from those of all of the reference compounds stored in the database. A significant production of 1-3 was observed in oatmeal medium in the 100 ml shake flask scale, which was reproducible in a scale up to a 20-liter fermentor. Strain BK 190 reached a maximal biomass of 12 volume (%) at a cultivation time of 96 h and this correlated with the highest production of elaiomycins, which reached yields of 24 mg l À1 elaiomycin (1), 15 mg l À1 elaiomycin B (2) and 9.5 mg l À1 elaiomycin C (3) in the culture filtrate, and 15 mg l À1 of 2 and 12 mg l À1 of 3 in the mycelium, respectively. Compounds 1-3 were isolated from the culture filtrate by separation on an Amberlite XAD-16 column (Rohm and Haas Deutschland, Frankfurt...

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Elaiomycins B and C, novel alkylhydrazides produced by Streptomyces sp. BK 190

et al. 2011

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“…These chemicals are indeed powerful carcinogens, since they induced tumours in over two dozen tissues and organs of mice, hamsters and rats (Juih'asz et al, 1957;Biancifiori & Ribacchi, 1962;Morris et al, 1969;Druckrey, 1970;Toth, 1975Toth, , 1980. It is of interest to note here that the human population is exposed to about one half of these compounds in the form of drugs, agricultural herbicides or industrial chemicals, and as naturally occurring substances such as ingredients of edible mushrooms and tobacco (Levenberg, 1960;List & Luft, 1968;Merck Index, 1976;Schmeltz et al, 1977;LaRue, 1977).…”

Section: Discussionmentioning

confidence: 99%

“…Earlier investigations were performed in this species with structural homologues of PFH, including N-methyl-N-formylhydrazine (MFR), N-ethyl-Nformylhydrazine and N-n-butyl-N-formylhydrazine (Totli & Nagel, 1978;Toth et al, 1979Toth & Nagel, 1908a. At the beginning, we selected MFH as the first step in otir inquiry because this chemical is an ingredient of the edible false morel mushroom Gyroinitra e8culenta (List & Luft, 1968; Schmidliii-Me'sza'ros, 1-975;Pyysalo & Niskaneii, 1977). It is known that the human poptilation is exposed to some extent, in certain areas, to this hazardous chemical (Miller, 1972).…”

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Tumorigenesis by N-n-propyl-N-formylhydrazine in mice

Tóth¹,

Nagel²,

Patil³

1980

Br J Cancer

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Summary.-Continuous administration of 0.040/0 N-n-propyl-N-formylhydrazine (PFH) for life in drinking water to 6-week-old randomly bred Swiss mice induced tumours of the lungs, preputial glands, liver and gall bladder. The tumour incidences in these 4 tissues were 91, 22, 8 and 6%, whereas in the untreated controls they were 25,0,0-5 and 0.50", respectively. The higher dose of 0.080/( PFH, given under identical conditions, induced only tumours of the lungs, liver and gall bladder in lower incidences, since the compound was too toxic for the mice. Histopathologically, the tumours were classified as adenomas and adenocarcinomas of the lungs, squamouscell papillomas, and carcinomas and fibrosarcoma of preputial glands, benign hepatomas and liver-cell carcinoma, as well as adenomas and adenocarcinoma of the gall bladder.

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“…The findings in the first case clearly demonstrated the diminishing role of increased methyl substitution in the carcinogenic process [14], while in the latter it was concluded that additional experimentation was needed [15]Hydrazines, hydrazides and hydrazones are capable of inducing tumors in experimental laboratory animals in a large variety of tissues. To date, over 40 such com pounds are known to possess cancer-inducing abilities in mice, hamsters and rats [1,2], From an environ mental viewpoint, it appears important that the human population is exposed to approximately one-half of these chemicals in the form of drugs, agricultural her bicides, industrial agents [3] and naturally occurring substances, such as the ingredients of tobacco and edible mushrooms [4][5][6]16].…”

Section: Discussionmentioning

confidence: 99%

“…To date, over 40 such compounds were reported to produce neoplasms in the lungs, liver, kidneys, blood vessels, bladder, heart, intestines, gallbladder, bile ducts, stomach, lymphoreticular and nerve tissues, etc. of mice, hamsters and rats [1,2], A number of these compounds are used in industry, agriculture and medi cine [3] and some also occur in nature [4][5][6], There fore, from an environmental viewpoint, it appears pro mising to study their carcinogenic potential, since the human population is considerably exposed to a subs tantial number of these chemicals. Some of these stu dies are also aimed at revealing the possible relationship between chemical structure and tumor development at specific organ sites.…”

Section: Introductionmentioning

confidence: 99%

Nicotinic Acid Hydrazide Carcinogenesis in Mice

Tóth¹

1981

Oncology

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Nicotinic acid hydrazide was administered as a 0.125% solution in drinking water continuously for life from 6 weeks of age to randomly bred Swiss albino mice. As a result of treatment, the lung tumor incidence rose from 25 to 76% in females and from 26 to 42% in males. The treatment had no statistically significant effect on the development of other types of tumors. Histopathologically the tumors were classified as adenomas and adenocarcinomas of the lungs. The study thus demonstrates the tumorigenicity of this compound which is a structural homologue of the tuberculostatic and carcinogenic isonicotinic acid hydrazide.

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Gyromitrin, das Gift der Frühjahrslorchel. 16. Mitt. über Pilzinhaltsstoffe

Abstract: Das Gift der Frühjahrslorchel wurde als N‐Methyl‐N‐formylhydrazon des Acetaldehyds aufgeklärt und synthetisiert.

Cited by 62 publications

References 9 publications

Elaiomycins B and C, novel alkylhydrazides produced by Streptomyces sp. BK 190

Elaiomycins B and C, novel alkylhydrazides produced by Streptomyces sp. BK 190

Tumorigenesis by N-n-propyl-N-formylhydrazine in mice

Nicotinic Acid Hydrazide Carcinogenesis in Mice

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