Tremorgenic toxins

SUBSTANCES ACTING ON THE NERVOUS SYSTEM Tremorgenic Toxins... 

A weakly neurotoxic metabolite, neoxaline (58) 107), mp 202°C (dec.), —16.3° (CHCI3), is described here even though it does not possess a diketopiperazine system in the molecule. It was isolated from cultures of Asp. japonicus (yield, 230 mg/18 liters) (see this treatise, Vol. 22 (1984), p. 317) 108). Its physicochemical properties are very similar to oxaline (59), isolated from Pen. oxalicum, and the unique structure was determined by correlation with oxaline (709). The efficient conversion of roquefortine (60) to oxaline (24.3%) is known (770), and neoxaline is probably also biosynthesized from 60, which has been isolated from Pen. roquefortii 111) as a tremorgenic toxin and has a tryptophan-histidine-derived diketopiperazine system in the molecule. 

Wilson BJ, Wilson CH, Hayes AW (1968) Tremorgenic toxin from Penicillium cyclopium grown on food materials. Nature 220 77... 

C32H35NO4, Mr 501.67, needles, mp, 222-224°C, component of Aspergillus /ZavMS- sclerotia and myce-lia, belongs to the class of tremorgenic toxins which cause trembling and cramps in animals (see also pas-palin under paspalitrems). In sclerotia A. has been attributed a protective function against animal attack. Lit. Cole-Cox, p. 410-413 Science 144, 177 (1964) Tetrahedron Lett. 1980, 239. - [CAS 70553-75-2]... 

Yamazaki, M., K. Sasago, and K. Miyaki The Structure of Fumitremorgin B (FTB), a Tremorgenic Toxin from Aspergillus fumigatus Fres. J. Chem. Soc. Chem. Commun. 1974, 408. 

Ling KH Territrems, tremorgenic mycotoxins isolated from Aspergillus terreus. J Toxicol Toxin Rev 1995 13 243-252. 

P. roqueforti that produce toxic metabolites which include the tremorgenic indoles and a group of sesquiterpenoids. PR Toxin (5.34) and the eremofortins are the best known of these highly oxygenated eremophilane sesquiterpenes. 

In 1972, a new tremorgenic mycotoxin was obtained in the United States from a strain of Penicillium verruculosum isolated from peanuts. The toxin was named verruculogen, and a close resemblance to fumitremorgin was evident. Oral administration of this toxin to mice caused tremor and convulsions and the toxin s LD50 was 126.7 mg/kg in mice. Intraperitoneal... 

Buchi et al. (1973) reported that tryptoquivaline and tryptoquivalone were tremor-producing toxins, and that the four newly isolated metabolites were also toxic (Biichi et al., 1977). However, details of their toxicity have not been described. Yamazaki et al., (1976) examined the tremorgenicity of the tryptoquivalines isolated in their laboratory and recognized no detectable tremorgenic activity from these metabolites. No antimicrobial activity was exhibited by tryptoquivaline and tryptoquivalone against 29 strains of yeast, two molds, and 46 bacteria (Demain et al., 1976). 

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