Clitocybe mushrooms

COjH >j C02H Japanese mushroom -Clitocybe acromelalga Acromeiic acids A-C -cytotoxic nonprotein amino acids 230... 

Toadstool -Clitocybe acromelalga Clithioneine - betaine from mushroom 217... 

From recent literature it must be coneluded that mushrooms of the genera Inocybe and Clitocybe contain toxic components that are different from muscarine. The severe symptoms reported of an Israeli ehild poisoned with /. tristis therefore departed from what is known of musearine poisoning (Amitai et al., 1982). The toxic activities of C. acromelalga and C. amoenolens, two Clitocybe species containing clitidine and acromelic acid A, respectively, were studied in rats (Fukuwatari et al., 2001 Saviuc et al., 2003). 

Fukawatari, T., Suigimoto, E. and Shibata, K. (2001). Effect of feeding with a poisonous mushroom Clitocybe acromelalga on the metabolism of tryptophan-niacin in rats. Shokuhin Eiseigaku Zasshi, 42, 190-196. 

Saviuc, P., Dematteis, M., Mezin, P., Danel, V. and Mallaret, M. (2003). Toxicity of the Clitocybe amoenolens mushroom in rat, Vet. Hum. Toxicol, 45, 180-182. Seeger, R. (1984). Zeitungspapiertest fiir Amanitine - falsch-positive Ergebnisse, Z. 

Atropine is used as an antidote in poisoning by an overdose of a cholinesterase inhibitor (see Chapter 14). It also is used in cases of poisoning from species of mushroom that contain high concentrations of muscarine and related alkaloids (e.g., Clitocybe dealbata). 

Muscarine Muscarine, molecular formula C9H2qN02, first isolated from fly agaric Amanita muscaria, occurs in certain mushrooms, especially in the species of the genera Inocybe and Clitocybe. It is a parasympathomimetic substance. It causes profound activation of the peripheral parasympathetic nervous system, which may result in convulsions and death. Muscarine mimics the action of the neurotransmitter acetylcholine at the muscarinic acetylcholine receptors. 

The Amanita muscaria mushroom from which muscarine is isolated is also psychoactive. It was believed at first that muscarine was the primary CNS agent. However, more detailed research indicated that muscarine only constituted 0.003% of the fungus. Other species of Inocybe and Clitocybe have more muscarine than muscaria. Other isoxazole components of the muscaria mushroom, such as ibotenic acid and its metabolites, are the main causes of amanita intoxication. This mushroom is believed to have been involved in ancient rituals of the Old World, especially in the Ayrian culture which lived in Siberia around 2000 B.C. This rite worshipped a god called Soma whose presence on earth occurred in the mushroom. Amanita muscaria. Rituals involved brewing a juice with the mushrooms which was consumed by priests. Their urine (isoxazole metabolites) was collected and drunk by others. This ceremony could involve many people and several metabolic rounds until everyone was intoxicated. 

Fig. 3.13 Clitocybe flaccida, the mushroom that contains the antifeedant clitolactone (907) (Photo W. F. Wood)...

A number of kainoids have been isolated from the poisonous Japanese mushroom, Clitocybe acromelalga. Acromelic acid A 5 and acromelic acid B 6 were isolated from this source by Shirahama and co-workers6 in 1983, their structures being confirmed from total syntheses by Takano et al.7,8 and semisynthetic approaches by Shirahama.9-11 More recently, an additional three acromelates have been isolated acromelic acids C... 

Natural products that contain the imidazole nucleus have been found in such diverse sources as mushrooms and broiled fish. In the former, the fresh fruiting bodies of Clitocybe acromelalga contain the new amino-acid betaine clithioneine... 

Acromelic acid A] Clitocybe acromelaga (mushroom) Non-NMDA-Glu-R (K-R)... 

Amanita muscaria (fly agaric mushroom) (Amanitaceae), Inocybe spp. (mushroom) (Cortinariaceae), Clitocybe spp. (mushroom) (Tricholomataceae) Synthetic... 

Illudin S (70) and illudin M (71) are two cyclopropane-containing toxins isolated from the bioluminescent mushroom Clitocybe illudens or Lampteromyces japonicus The... 

Muscarinic, e.g. from Inocybe and Clitocybe fungi (mushrooms), causing salivation, lachrymation, miosis, perspiration, bradycardia and bronchoconstriction, also hallucinations. 

Muscarine is present in certain mushrooms in many genera, notably the Inocybe and Clitocybe genera, but small amounts are also present in the fly agaric, Amanita muscaria. The ecological function of this nerve poison in the fungus is not understood. In mammals, the typical symptoms are unrest, irritability, excitement, sweating, salivation, respiratory trouble, feeble pulse,... 

Clitocine. Clitocine [105798-74-1] (178), C9H13N506, isolated from the mushroom, Clitocybe inversa, is... 

Muscarine-histamine poisoning occurs when mushrooms from the Inocybe or Clitocybe species such as I. geophylla, or C. dealbata (Sweat mushrooms) are eaten. 

Generally these mushrooms are small, brown and leathery (Inocybe species) or small white and leathery (Clitocybe species)... 

Over 30 sesquiterpene aryl esters have been isolated from Armillaria spp. of these, eight are esterified with chlorinated orsellinate. The honey mushroom, A. mellea, produces 70 mg of the chlorinated compound armillaridin (122) per kg dry mycelium [148], while liquid cultures of A. ostoyae contain the chlorinated compounds, melledonal C (123) (50 mg/1) and melleolide D (35 mg/1) (124) [149]. Clitocybe elegans is the only other genus for which chlorinated sesquiterpene aryl esters have been reported [150], including melledonal D (125), which has not yet been detected in Armillaria spp. The pathogenic basidiomycete, Armillaria causes root disease in both coniferous and deciduous trees. Armillaria... 

Mushrooms are a rich source of toxins mushroom poisoning has increased as the result of the popularity of hunting wild mushrooms. High concentrations of muscarine are present in various species o/Inocybe and Clitocybe. The symptoms of muscarine intoxication (salivation, lacrima-tion, nausea, vomiting, headache, visual disturbances, abdominal colic, diarrhea, bronchospasm, bradycardia, hypotension, shock) develop within 30-60 minutes of ingestion. Treatment with atropine (1-2 mg intramuscularly every 30 minutes) effectively blocks these effects. 

C. Reversal of central (by atropine) and peripheral (by atropine and glycopyrrolate) muscarinic symptoms in patients with intoxication by Clitocybe or In-ocybe mushroom species. 

Nebularine 9-P-D-ribofutanosylpurme [M, 2S223, m. 181-182°C, fajo -48.6° (c = 1, water)], a pitrine antibiotic (see Nucleoside antibiotics) synthesized by the mushroom Agaricus (Clitocybe) nebularis, and by Streptomyces spp. N. is selectively active against mycobacteria It has ntarked cytostatic properties, and in animals it is among the most poisonous of the pmine derivatives. 

Kubo, I. et al., Clitocine, a new insecticidal nucleoside from the mushroom Clitocybe inversa. Tetrahedron Lett., 21, 4277, 1986. 

Nucleoside antibiotic. Isol. from the mushroom Clitocybe nebularis (clouded agaric), from Streptomyces yokosukaen-sis and Microbispora sp. nov. Shows tuberculostatic and antimitotic activity. Adenosine deaminase inhibitor. Investigated as an antileukaemic agent in combination therapies. Needles (MeOH). 

Stimulates muscarinic receptors of the po tgar glionic parasympathetic effector organs mushroom ger>era (e.g., Inocybe, Boletus, Clitocybe) contain muscarine or other cholineigic toxins that cause acute onset of cholinergic signs blood-brain barrier prevents access to CNS... 

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