Secondary metabolites trivial name - verruculogen
Species A. egyptiacus, A. fumigatus, Neosartorya fischeri
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
Chemical abstracts number 12771-72-1
PubChem URL Go to PubChem link
Selected references 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.
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.
Structure diagram
3D Structure
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