Tremorgenic mycotoxins

Neoxaline, C23H25N5O4, a new metabolite of Aspergillus japonicus, exhibits similarities to oxaline in its i.r. and n.m.r. spectra, and may be an indole derivative, but nothing further is known of its constitution as yet.38a Similarly, three new tremorgenic mycotoxins from Penicillium janthinellum, janthitrems A, B, and C, may also be indole derivatives.386... 

IP3-R (Precursor of mACh-R agonist tremorgen Lolitrem B) [tremorgen mycotoxin]... 

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

Steyn PS Mycotoxins, general view, chemistry and structure. Toxicol Lett 1995 82 843-851. Yamaguchi T, Nozawa K, Hosoc T, Nakajima S, Kawai KL Indoloditerpenes related to tremorgenic mycotoxin penitrems, from Penicillium crustosum. Phytochemistry 1993 32 1177-1181. Penn J, Swift R, Wigley LJ, Mantle PG, Bilton JN, Sheppard RN Janthitrems B and C, two principal indole-diterpenoids produced by Penicillium janthinellum. Phytochemistry 1993 32 1431-1434. 

An improved procedure for the production of the tremorgenic mycotoxins trypto-quivaline and tryptoquivalone by Aspergillus clavatus, has been reported this makes use of pearled barley in a procedure based on Hesseltine s solid substrate fermentation technique. 

Munday-Finch SC, Wilkins AL, Miles CO, Tomoda H, Omura S. Isolation and structure elucidation of lolilline, a possible biosynthetic precursor of the lolitrem family of tremorgenic mycotoxins. J Agric Food Chem 45 199-204, 1997. 

Steyn PS, Vleggaar R. Tremorgenic mycotoxins. Prog Chem Org Nat Prod 48 1 -80,1985. 

Similar structural features are also demonstrated by penitrems A to F (Fig. 18), which form a small family of tremorgenic mycotoxins produced by the ergot fungus Penicillium crustosum. The structure of these alkaloids was elucidated by Steyn and co-workers (238-241), and an approach to the total synthesis of penitrem D was also presented (242). 

Penitrem D (226) (Scheme 41) is one member of the penitrem family, which is a small family of structurally complex tremorgenic mycotoxins, and was isolated from the ergot fungus Penicillium crustosum by Steyn and coworkers in 1981 [90]. 

Contents P. S. Steyn and R. Vleggaar Tremorgenic Mycotoxins. — R. E. Moore Structure of Palytoxin. — P. Crews and S. Naylor Sesterterpenes An Emerging Group of Metabolites from Marine and Terrestrial Organisms. 

Total synthesis of fumitremorgins and verruculogens, tremorgenic mycotoxins— pentacyclic systems with 3-carboline fragments 97H(46)673. 

Four paspalitrem-type tremorgenic mycotoxins (paxilline, paspaline, paspalinine and paspalicine) extracted from molds were baseline resolved on a silica column (A = 230nm) using a 90/10 DCM/ethyl ether mobile phase. Peak shapes were excellent and elution was complete in 5 min. Linear working curves from 2 to 300 ng/pL and detection limits of 0.5 pg/mL were reported [787]. 

Five tremorgenic mycotoxins, containing indole condensed with a diterpenoid unit, have been isolated from Claviceps paspali paraziting on the grass Paspalum dilatatum (Acklin et al, 1977 Cole et al, 1977 Scott, 1984). Their structures are in the Figure 18. 

The rice leaf binding component, prodnced in aerobic cnltures of the strain Claviceps purpurea ATCC 9605 or of a number of other microorganisms (Oishi et al., 1984), can be used to increase the rice crop. The active component increases the yield and shortens the production period. Also other metabolites of Claviceps can find application in agriculture practice. Patent of Dowd et al. (1988) describes the use of tremorgenic mycotoxins as insecticides against corn earworm and fall armyworm. Gubanski and Lowkis (1964) have demonstrated the inhibition of the tobacco mosaic virus by a substance isolated from C. purpurea. 

Tremorgens were found in a number of commodities, such as maize, wheat, nuts, silage and other feeds. Tremorgenic mycotoxins... 

The various derivatives of lysergic acid, including the tremorgenic mycotoxins, are associated with reduced concentration or function of the inhibitory amino acids [e.g., v-aminobutyric acid (GABA), glycine]. 

A specific inhibitor of BCRP is the tremorgenic mycotoxin fumitremorgin C (FTC). FTC blocked mitoxantrone transport by BCRP without affecting P-gp or MRPl-mediated drug resistance (Rabindran et al., 2000). However, due to neurotoxic effects in vivo apvplication is still not possible. 

Nozawa, K., Udagawa, S., Nakajima, S., and Kawai, K.J. (1987) Stnicture of two stereoisomers of a new type of indoloditerpene related to the tremorgenic mycotoxin paxiUine, from Emericetta desertorum and Emericdla striata.]. Chem. Soc. Chem. Commun., 1157-1159. 

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... 

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