verruculogen

Toxin: 

y

Systematic name: 

(5R-(5alpha, 10 alpha, 10aalpha, 14aalpha, 15balpha))-1, 10, 10a, 14, 14a, 15b-Hexahydro-10, 10a-dihydroxy-7-methoxy-2, 2-dimethyl-5-(2-methyl-1-propenyl)-5H, 12H-3, 4-dioxa-5a, 11a, 15a-triaza cyclooct (1m) indeno (5,6-b)fluorene-11, 15(2H,13H)-dione 10

Molecular formulae: 

C27H33N3O7

Molecular weight: 

511.567

Chem abstract number: 

12771-72-1

Literature reference: 

Patterson DS, Shreeve BJ, Roberts BA, MacDonald SM. Verruculogen Produced by soil fungi in England and Wales. Appl Environ Microbiol. 1981 Nov;42(5):916-7.
Shreeve BJ, Patterson DS, Roberts BA, MacDonald SM. Tremorgenic fungal toxins. Vet Res Commun. 1983 Dec;7(1-4):155-60.
Nielsen PV, Beuchat LR, Frisvad JC. Growth of and fumitremorgin production by Neosartorya fischeri as affected by temperature, light, and water activity. Appl Environ Microbiol. 1988 Jun;54(6):1504-10.

Chemical type: 

Indole Alkaloid

Toxicity: 

Verruculogen is a tremorgen. Tremorgenic mycotoxins are lipophilic molecules that may cross the blood brain barrier and gain access to the centeral nervous system, clinical studies indicate that these compounds affect neurotransmitter release. Verruculogen increases spontaneous glutamate and aspartate release. In vivo, in guinea pig ileum preparations, verruculogen causes an increase in contractile responses due to electrical field stimulation, attributed to enhancement of acetylcholine from presynaptic nerve terminals. Verruculogen also was shown to increase presynaptic neurotransmitter release at the locust neuromuscular junction. chicken LD50 intraperitoneal 15200ug/kg (15.2mg/kg) Journal of Antibiotics. Vol. 41, Pg. 1868, 1988. >Link to PubMed chicken LD50 oral 266mg/kg (266mg/kg) Journal of Antibiotics. Vol. 41, Pg. 1868, 1988. >Link to PubMed mouse LD50 intraperitoneal 2400ug/kg (2.4mg/kg) Journal of Antibiotics. Vol. 41, Pg. 1868, 1988. >Link to PubMed mouse LD50 oral 127mg/kg (127mg/kg) Journal of Antibiotics. Vol. 41, Pg. 1868, 1988. >Link to PubMed mouse LD50 unreported 2400ug/kg (2.4mg/kg) "Toxicology, Biochemistry and Pathology of Mycotoxins," Uraguchi, K. and M. Yamazaki, eds., New York, John Wiley & Sons, Inc., 1978Vol. -, Pg. 108, 1978.

History: 

Structure image: 

Aspergillus Species known to produce this metabolite: 

Date uploaded: 

2005-12-16 00:00:00