Some Metabolic Products of Basidiomycetes 3 



ture liquids of Copnnus similis and Lentinus degener. It fits into a 

 series of oxygenated quinones, two closely related members of which, 

 fumigatin (II) and spinulosin (III), were isolated from species of 

 Penicillium and Aspergillus. 4 Another closely related quinone, 2,5- 

 dimethoxyquinone (IV) has been isolated from the basidiomycete, 

 Polyporus jumosus. 5 



O 



CH 3 O^L J CH 3 



, CH 3 hOitSch, 



u 



HO ljil CH3 [fi] 0CH3 



CH 3 olL^OH CH30IJ 



II II 



o o 



III IV 



Sesquiterpenes 



The compounds included here, solely on the basis of their molecular 

 formulas, are illudin M and illudin S, isolated from culture liquids 

 of Clitocybe illudens, and marasmic acid, from culture liquids of 

 Marasmius conigenus. Illudin M, C15H20O3, and illudin S, Ci 5 H 2 o0 4 * 

 (previously reported as C15H22O4), 6 show striking resemblance in 

 their chemical behavior to santonin, Ci 5 Hi 8 3 , and pseudosantonin, 

 C15H20O4, which have been isolated from higher plants. All four com- 

 pounds possess carbonyl groups. The santonins, and probably the 

 illudins, possess a lactone ring. Pseudosantonin and illudin S yield 

 acetates. Oxygen is lost on catalytic reduction of the illudins, but in 

 the santonins straightforward saturation of the double bonds and 

 reduction of the carbonyl group occur (also hydrogenolysis of the 

 lactone ring of pseudosantonin). 7 The behavior of the two groups of 

 compounds towards reduction is not understood because the mechanism 

 of oxygen loss in the illudins is unknown. All four compounds undergo 

 acidic rearrangements which yield more than one product, and, in each 

 case, one of the products is phenolic. Marasmic acid, 8 C15H18O4,* like 



* Unpublished work. 



