verruculogen

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| ImageFile = Verruculogen.svg

| ImageSize = 200px

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| PIN =(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

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| CASNo = 12771-72-1

| PubChem = 104862

| ChemSpiderID = 10405461

| KEGG = C20045

| SMILES = CC(=CC1N2C3=C(C=CC(=C3)OC)C4=C2C(CC(OO1)(C)C)N5C(=O)C6CCCN6C(=O)C5(C4O)O)C}}

|Section2={{Chembox Properties

| C=27 | H=33 | N=3 | O=7

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Verruculogen is a mycotoxin produced by certain strains of aspergillus that belongs to a class of naturally occurring 2,5-diketopiperazines.{{Cite journal | title = 2,5-Diketopiperazines: Synthesis, Reactions, Medicinal Chemistry, and Bioactive Natural Products | author = Borthwick AD | journal = Chemical Reviews | year = 2012 | volume = 112 | issue = 7 | pages = 3641–3716 | doi = 10.1021/cr200398y | pmid = 22575049}} It is an annulated analogue of cyclo(L-Trp-L-Pro) which belongs to the most abundant and structurally diverse class of tryptophan-proline 2,5-diketopiperazine natural products. It produces tremors in mice due to its neurotoxic properties. It also tested positive in a Salmonella/mammalian microsome assay and was shown to be genotoxic. It is a potent blocker of calcium-activated potassium channels.{{cite web|url=http://www.sigmaaldrich.com/catalog/product/sigma/v7755?lang=en®ion=US|title=Verruculogen from Penicillium verruculosum|website=sigmaaldrich.com|access-date=25 September 2023}}