A tremorgenic mycotoxin
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Verruculogen

Item No. 11351

Technical Information
Formal Name
(5R,10S,10aR)-1,10,10a,14,14aS,15bS-hexahydro-10,10a-dihydroxy-7-methoxy-2,2-dimethyl-5-(2-methyl-1-propen-1-yl)-5H,12H-3,4-dioxa-5a,11a,15a-triazacyclooct[lm]indeno[5,6-b]fluorene-11,15(2H,13H)-dione
CAS Number
12771-72-1
Synonyms
  • NA 209A
  • TR 1
Molecular Formula
C27H33N3O7
Formula Weight
Purity
≥95%
Formulation
A solid
DMF: SolubleDMSO: SolubleEthanol: SolubleMethanol: Soluble
SMILES
O=C1N2[C@](CCC2)([H])C(N3[C@@H]4C5=C(C(C=CC(OC)=C6)=C6N5[C@@H](/C=C(C)/C)OOC(C)(C)C4)[C@H](O)[C@]31O)=O
InChi Code
InChI=1S/C27H33N3O7/c1-14(2)11-20-29-18-12-15(35-5)8-9-16(18)21-22(29)19(13-26(3,4)37-36-20)30-24(32)17-7-6-10-28(17)25(33)27(30,34)23(21)31/h8-9,11-12,17,19-20,23,31,34H,6-7,10,13H2,1-5H3/t17-,19-,20+,23-,27+/m0/s1
InChi Key
LRXYHMMJJCTUMY-GWXUGYLUSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Verruculogen is a tremorgenic mycotoxin isolated from species of Penicillium, Aspergillus, and other fungi.1,2 It selectively inhibits the activation of large-conductance calcium-activated potassium channels (KCa1.1/BK) potassium channels by charybdotoxin with a K1/2 value of 170 nM.3 Verruculogen also promotes the release of excitatory neurotransmitters when injected directly into the brain of rats and, at high doses, arrests mouse mammary carcinoma cells in M phase of the cell cycle (MIC = 12.2 μM).4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Cole, R.J., Kirksey, J.W., Moore, J.H., et alTremorgenic toxin from Penicillium veruculosum. Appl. Microbiol. 24(2), 248-250 (1972).

    2. Abad, A., Fernández-Molina, J.V., Bikandi, J., et alWhat makes Aspergillus fumigatus a successful pathogen? Genes and molecules involved in invasive aspergillosis. Rev. Iberoam. Micol. 27(4), 155-182 (2010).

    3. Knaus, H.G., McManus, O.B., Lee, S.H., et alTremorgenic indole alkaloids potently inhibit smooth muscle high-conductance calcium-activated potassium channels. Biochemistry 33(19), 5819-5828 (1994).

    4. Peterson, D.W., Bradford, H.F., and Mantle, P.G. Actions of a tremorgenic mycotoxin on amino acid transmitter release in vivo. Biochem. Pharmacol. 31(17), 2807-2810 (1982).

    5. Cui, C.B., Kakeya, H., Okada, G., et alNovel mammalian cell cycle inhibitors, tryprostatins A, B and other diketopiperazines produced by Aspergillus fumigatus. I. Taxonomy, fermentation, isolation and biological properties. J. Antibiot. (Tokyo) 49(6), 527-533 (1996).