12771-72-1
Chemical Structure
Verruculogen
- CAS. Nr.: 12771-72-1
- Formula:C27H33N3O7
- Molecular Weight:511.57
IUPAC Name: (5R,10S,10aR,14aS,15bS)-10,10a-dihydroxy-7-methoxy-2,2-dimethyl-5-(2-methylprop-1-en-1-yl)-1,10,10a,12,13,14,14a,15b-octahydro-5H,15H-3,4-dioxa-5a,11a,15a-triazacycloocta[lm]indeno[5,6-b]fluorene-11,15(2H)-dione
InChIKey: LRXYHMMJJCTUMY-GWXUGYLUSA-N
SMILES: C/C(C)=C\[C@@H]1N2C3=C([C@@H]([C@@]4(N(C([C@@]5([H])N(CCC5)C4=O)=O)[C@@]3([H])CC(C)(OO1)C)O)O)C6=CC=C(OC)C=C62
Biological Activity: Verruculogen is a tremorgenic mycotoxin and inhibitor of the M phase of the mammalian cell cycle. Verruculogen is produced by Penicillium and Aspergillus species. Verruculogen enhances the binding of ChTX to maxi-k channels with a K1/2 value of 170 nM. Verruculogen inhibits the amplitude of Ca2+-activated K+ currents. Verruculogen induces severe tremors in infected animals[1][2][3][4][5].
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Verruculogen | 98.08% | Verruculogen is a tremorgenic mycotoxin and inhibitor of the M phase of the mammalian cell cycle. Verruculogen is produced by Penicillium and Aspergillus species. Verruculogen enhances the binding of ChTX to maxi-k channels with a K1/2 value of 170 nM. Verruculogen inhibits the amplitude of Ca2+-activated K+ currents. Verruculogen induces severe tremors in infected animals. | ||||||||||||||||||||
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References
- [1]. Luciane M. Kawashima, et al. The development of an analytical method for two mycotoxins, patulin and verruculogen, and survey of their presence in commercial tomato pulp. Brazilian Journal of Microbiology
- [2]. Knaus HG, et al. Tremorgenic indole alkaloids potently inhibit smooth muscle high-conductance calcium-activated potassium channels. Biochemistry. 1994 May 17;33(19):5819-28. [Content Brief]
- [3]. Cui CB, et al. Novel mammalian cell cycle inhibitors, tryprostatins A, B and other diketopiperazines produced by Aspergillus fumigatus. II. Physico-chemical properties and structures. J Antibiot (Tokyo). 1996 Jun;49(6):534-40. [Content Brief]
- [4]. Huang MH, et al. Stimulatory actions of thymol, a natural product, on Ca(2+)-activated K(+) current in pituitary GH(3) cells. Planta Med. 2005 Dec;71(12):1093-8. [Content Brief]
- [5]. Intorre L, et al. Behavioural and biochemical effects of the Tremorgenic Mycotoxin Verruculogen. Toxicological & Environmental Chemistry, 1994, 46(1-2): 119-125.
