Chaetomium cochliodes

Urushiol Rhus vernicefera, Rhus toxicodendron 0-orsellinic acid Chaetomium-cochliodes... 

Safe S, Taylor A, Sporidesmins. XIII. Ovine Ill-thrifr in Nova Scotia. III. Characterization of chetomin, a toxic metabolite of Chaetomium cochliodes and Chaetomium globosum, J Chem Soc Perkin Tmm 74 472—479, 1972. 

Abraham et al. [144-146] studied the biotransformation of caryophyllene (190) and humulene (196) by Diplodia gossypina (ATCC 10936) and two strains of Chaetomium cochliodes (DSM 63353 and ATCC 10195), Fig. (38) and Fig. (39). Sixty three products, including 49 that had never been described previously, were obtained and tested for their biological activity [147]. More recently, the bioconversion of (-)-caryophyllene by Chaetomium cochliodes IFO 30576 was also studied by another group [148]. The substrate was first epoxidized at the C-C double bond, producing (-)-caryophyllene-4,5-oxide (191), which was then hydroxylated at the ge/n-dimethyl group and C-7 position giving 193. 

Fig. (38). Main biotransformation products of caryophyllene by Diplodia gossypina and Chaetomium cochliodes (after [144,145])...

Calycanthine and chimonanthine have been found to occur in Palicourea fendleri 142 this is the second report of the occurrence of calycanthine in the genus Palicourea. The structure of the antibiotic chetomin (241) has been elucidated,143 mainly by 1SN and 13C n.m.r. spectroscopy on 15N-enriched material obtained from the culture of Chaetomium cochliodes in a nutrient medium containing Na15N03. 

Tryptophan and its relative indolylpyruvic acid (3.42) have been shown to precursors of hinnuliquinone (3.41), which is a pigment of Nodulisporium hin-nuleum. Typical of many fungal indoles in which alkylation by a dimethylallyl or isopentenyl group has occurred, mevalonate was also a precursor. However, the stage at which prenylation of a monomer or a dimer took place was unclear. Asterriquinone (3.43) from Aspergillus terreus and cochliodinol (3.44) from Chaetomium cochliodes are similar metabolites. Fission of the hydroxyquinone in the latter followed by lactonization leads to cochliodinone (3.45) in a sequence that is similar to that which inter-relates the terphenyls and pulvinic acids described in Chapter 7. 

Chetomin, a toxic metabolite from Chaetomium cochliodes and C. glohosum, has been assigned the structure (101) as the most reasonable working possibility on present evidence. Analyses revealed the presence of two acylatable and... 

Sporidesmin and its metabolites were isolated from Chaetomium cochliodes and show structural similarity to 308. They also inhibit the... 

Chaetoglobosins. Ch. A - G and J are metabolic products from Chaetomium cochliodes, Ch. globosum, and other Chaetomium species (Ascomycetes) Ch. K,... 

FIGURE 20.131 Biotransformation of (-)-P-caryophyllene (451) by Pseudomonas cruciviae, Diplodia gossypina, and Chaetomium cochliodes. 

Mosbach, K. (1959). Das Vorkommen von Orsellinsaure in Chaetomium cochliodes. Z. Natur-forsch. B 14, 69. 

Chaetomin, Chaetomin (79,162), CHONS (empirical formula unknown), not crystalline, m.p. 218-220°C. dec., neutral substance soluble in acetone, ethyl acetate, chloroform, and benzene less soluble in ether and alcohol insoluble in water and petroleum ether. Chaetomin can be heated in water to 100°C. for ten minutes. It is stable in alcoholic solution and in 0.01 N hydrochloric acid at room temperature for 24 hours. It is destroyed in 24 hours at room temperature by 5% sodium carbonate solution. Chaetomin is produced by Chaetomium cochliodes grown on Czapek-Dox and corn-steep media in static and shaken cultures. Most (95%) of the chaetomin is found in the mycelium. A liter of culture fluid may yield... 

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