Verruculogen

Specifications / Handling

More Information
Product Details
Synonyms	NA 209A; TR 1
Product Type	Chemical
Properties
Formula	C₂₇H₃₃N₃O₇
MW	511.6
CAS	12771-72-1
RTECS	JH4920000
Source/Host Chemicals	Isolated from Aspergillus fumigatus.
Purity Chemicals	≥98% (HPLC)
Appearance	White to off-white solid.
Solubility	Soluble in DMSO, 100% ethanol, methanol or dichloromethane.
Identity	Determined by ¹H-NMR and MS.
Declaration	Manufactured by BioViotica.
InChi Key	LRXYHMMJJCTUMY-GWXUGYLUSA-N
Smiles	O=C(N[C@H](CCCC)C(O[Na])=O)[C@@H](C1=CN(C(OC)=O)C2=C1C=CC=C2)NC([C@H](CC(C)(C)C)NC(N3[C@H](C)CCC[C@@H]3C)=O)=OO=C1N2[C@](CCC2)([H])C(N([C@@]1(O)[C@H]3O)[C@@]4([H])CC(C)(C)OO[C@@](/C=C(C)\C)([H])N5C4=C3C6=C5C=C(OC)C=C6)=O
Shipping and Handling
Shipping	AMBIENT
Short Term Storage	+4°C
Long Term Storage	-20°C
Handling Advice	Protect from light when in solution.
Use/Stability	Stable for at least 2 years after receipt when stored at -20°C. Store solutions at -20°C in the dark.
Documents
MSDS	Download PDF
Product Specification Sheet
Datasheet	Download PDF

Product-specific References

Description

Fumitremorgin-type alkaloid.
Tremorgenic neurotoxic mycotoxin.
Selective blocker of KCa1.1 (high-conductance Ca²⁺-activated K⁺; BK; maxi-K) channels.
Decreases GABA levels in CNS.
Increases spontaneous glutamate and aspartate release.
At toxic doses, increases the number and decreases the affinity of DHP receptors in rat cortex.
Cell cycle inhibitor at the M phase.
Inhibits calmodulin and PKC activity.
Has apoptotic effects on human T lymphocytes.
Stimulates the growth of seedling roots of buckwheat.

Product References

Tremorgenic toxin from Penicillium veruculosum: R.J. Cole, et al.; Appl. Microbiol. 24, 248 (1972)
The structure of verruculogen. A tremor producing epoxide from Penicillium erruculosum: J. Fayos, et al.; JACS 96, 6785 (1974)
Verruculogen: a new substance for decreasing of GABA levels in CNS: L. Hotujac, et al.; Pharmacol. 14, 297 (1976)
Actions of tremorgenic fungal toxins on neurotransmitter release: P.J. Norris, et al.; J. Neurochem. 34, 33 (1980)
Actions of a tremorgenic mycotoxin on amino acid transmitter release in vivo: D.W. Peterson, et al.; Biochem. Pharmacol. 31, 2807 (1982)
In vitro effects of tremorgenic mycotoxins: M.I. Selala, et al.; J. Nat. Prod. 54, 207 (1991)
Tremorgenic indole alkaloids potently inhibit smooth muscle high-conductance calcium-activated potassium channels: H.H. Knaus, et al.; Biochemistry 33, 5819 (1994)
Behavioral and biochemical effects of the tremorgenic mycotoxin verruculogen: L. Intorre, et al.; Environ. Toxicol. Chem. 46, 119 (1994)
Novel mammalian cell cycle inhibitors, tryprostatins A, B and other diketopiperazines produced by Aspergillus fumigatus. II. Physico-chemical properties and structures: C.B. Cui, et al.; J. Antibiot. 49, 534 (1996)
Total synthesis of fumitremorgins and verruculogens: T. Hino & M. Nakagawa; Heterocycles 46, 673 (1997)
Modulation of calmodulin and protein kinase C activities by Penicillium mycotoxins: I. Pala, et al.; Int. J. Toxicol. 18, 91 (1999)
Genotoxicity assessment of five tremorgenic mycotoxins (fumitremorgen B, paxilline, penitrem A, verruculogen and verrucosidin) produced by molds isolated from fermented meats: M. Sabater-Vilar, et al.; J. Food Protect. 66, 2123 (2003)
Influence alkaloids from the marine-derived strain of the fungus Aspergillus fumigatus Fresen. on the growth of seedling roots of buckwheat (Fagopyrum esculentum Moench): M. Anisimov, et al.; Int. J. Res. Rev. Appl. Sci. 13, 326 (2012)
Aspergillus fumigatus toxins cause cytotoxic and apoptotic effects on human T lymphocytes (Jurkat cells): H. Malekinejad, et al.; World Mycotoxin 6, 65 (2013)

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