{{Chembox | ImageFile = Verruculogen.svg | ImageSize = 200px | ImageAlt = | PIN =(5''R'',10''S'',10a''R'',14a''S'',15b''S'')-10,10a-Dihydroxy-7-methoxy-2,2-dimethyl-5-(2-methylprop-1-en-1-yl)-1,10,10a,12,13,14,14a,15b-octahydro-5''H'',15''H''-3,4-dioxa-5a,11a,15a-triazacycloocta[''lm'']indeno[5,6-''b'']fluorene-11,15(2''H'')-dione | OtherNames = |Section1={{Chembox Identifiers | CASNo = 12771-72-1 | ChemSpiderID = 10405461 | EINECS = 634-189-1 | KEGG = C20045 | PubChem = 104862 | StdInChI=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 | StdInChIKey = LRXYHMMJJCTUMY-UHFFFAOYSA-N | 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 | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }}
'''Verruculogen''' is a mycotoxin produced by certain strains of ''aspergillus'' that belongs to a class of naturally occurring 2,5-diketopiperazines.<ref>{{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}}</ref> 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.<ref>{{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}}</ref>
==Synthesis== Both verruculogen and its isoprenyl derivative fumitremorgin A belong to the only family of alkaloids with an eight-membered endoperoxide ring, and both have been synthesised involving ligand-controlled C–H borylation.<ref name="pmid226256033">{{ cite journal |vauthors=Feng Y, Holte D, Zoller J, Umemiya S, Simke LR, Baran PS | title = Total Synthesis of Verruculogen and Fumitremorgin A Enabled by Ligand-Controlled C–H Borylation | journal = Journal of the American Chemical Society | volume = 137 | issue = 32 | pages = 10160–10163 | date= August 2015| pmid = 26256033 | doi = 10.1021/jacs.5b07154 | pmc = 4777340 | bibcode = 2015JAChS.13710160F }}</ref>
==References== {{reflist}}
Category:Mycotoxins Category:Diketopiperazines Category:Organic peroxides Category:Indole alkaloids Category:Heterocyclic compounds with 6 rings Category:Methoxy compounds Category:Diols