Clitocybe

P. olearius ( Jack O Lantern several synonyms, including Clitocybe illudens and Ompbalotus olearius), P. japonicus (syn. Lampteromyces japonicus), P. noctilucens... 

Identification of an Antibiotic Polyacetylene from Clitocybe diatreta as... 

Structurally rather complicated target molecules can be synthesized with the aid of thi-olate 1,6-addition reactions to acceptor-substituted dienes as well. For example, a richly functionalized proline derivative with a 2,4-pentadienal side chain was converted into the corresponding 6-phenylthio-3-hexen-2-one derivative by 1,6-addition of phenylthiolate, treatment of the adduct with methyl lithium and oxidation (equation 46)127. The product was transformed into acromelic acid A, the toxic principle of clitocybe acromelalga ichimura. Similarly, the 1,6-addition reaction of cesium triphenylmethylthiolate to methyl 2,4-pentadienoate served for the construction of the disulfide bridge of the macrobicyclic antitumor depsipeptide FR-901,228128. 

The process of forest litter decomposition is one of the key processes leading to the redistribution of Cs among the ecosystem components. It is affected by two major factors the rate of decomposition, which is dependent on the composition of the litter and the time since the introduction of Cs, which determines the level of decomposition of the uppermost, most heavily contaminated layer. The distribution of i Cs between the separate litter layers is important, since Of and Oh are critical for the roots of many undergrowth plant species (such as V. myrtillus, V. vitis-idaea, V. uUginosu and L. palustre ) and fungal saprotrophs (Clitocybe,... 

Anchel, M. Metabolic Products of Clitocybe diatreta. III. Characterization of diatretyne 3 as trans-10-hydroxy-dec-2-cn-4,6,8-tr5moic acid. Arch. Bioch. Biophys. 85, 569 (1959). 

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. 

Anchel M, Metabolic products of Clitocybe diatreta. I. Diatretyne amide and diatretyne nitrile. Arch Biochem Biophys 78 100—110, 1958. 

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). 

Acromelic acid A (260), isolated from Clitocybe acromelaga, displays the most potent polarizing effect of aU known kainoids. By application of the same intramolecular aziridine thermolysis route described above, Takano et al. (80) outlined a concise entry into such compounds. Thermolysis of the chiral aziridine 261, derived from (5)-0-benzylglycidol in 1,2-dichlorobenzene at 200 °C, furnished the single reaction product 262 in 73% yield. The complete control over the... 

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)...

Wood WF, Clark TJ, Bradshaw DE, Foy BD, Largent DL, Thompson BL (2004) Clitolac-tone A Banana Slug Antifeedant from Clitocybe flaccida. Mycologia 96 23... 

Amone A, Cardillo R, Di Modugno V, Nasini G (1988) Secondary Mould Metabolites. XXII. Isolation and Structure Elucidation of Melledonals D and E and Melleolides E-H, Novel Sesquiterpenoid Aryl Esters from Clitocybe elegans and Armillaria mellea. Gazz Chim Ital 118 517... 

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... 

Further investigation of the metabolites of Clitocybe illudens has revealed the presence of neoilludol (160), the allylic isomer of illudol (161).75 A new synthetic... 

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... 

D-Ribofuranosyl)purine Nebularine Agaricus (clitocybe)nebularis and S. yokosukanensis) B-70MI40900, p. 261... 

Scheme 3. Possible and Cjo precursors incorporated (T5-4%) by cultures of the fungus Clitocybe rhizophora into CH3CH2CH(OH)(C=C)2CH(OH)CHjOH (38).

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. 

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