Clitocybe nebularis

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

Nebularine has long been known as a metabolite of Clitocybe nebularis (383), revealing tuberculostatic and antimitotic activity (383-385). Few syntheses of this compound having a 9-(D-ribosyl)purine structure have been reported, namely, the Brown (386) approach, starting from a chloro-mercuri-6-purine and 2,3,5-tri-O-acetyl-D-ribofuranosyl chloride, the Fox (387) procedure, based on the transformation of inosine to nebularine via a desulfurization by Raney nickel of the thioinosine intermediate, and the Iwamura-Hashizume (384,388) method, in which nebularine and its N-7 isomer were synthesized simultaneously by the fusion of purine and tetra-O-acetyl-D-ribofuranose using bis(p-nitrophenyl)hydrogen phosphate as the catalyst. 

C10H12N4O4, Mr 252.23, cryst., mp. 182-183 °C, [a] -46.8° (H2O). A nucleoside antibiotic from the fungus Clitocybe nebularis, an agaric frequently found in Central European woods in autumn. N. has also been found in a Streptomyces species. N. has antimitotic and tuberculostatic activities, LD50 (rat/guinea-pig s.c.) 220/15 mg/kg. 

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. 

Nebulaiin Agaricus (Clitocybe) nebularis, Streptomyces spp. Purine Ribose Adenosine... 

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). 

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