Verruculogen

Verruculogen
Names
	Preferred 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
Identifiers
CAS Number	12771-72-1;
3D model (JSmol)	Interactive image;
ChemSpider	10405461;
ECHA InfoCard	100.162.193
KEGG	C20045;
PubChem CID	104862;
CompTox Dashboard (EPA)	DTXSID30894030 ;
	SMILES CC(=CC1N2C3=C(C=CC(=C3)OC)C4=C2C(CC(OO1)(C)C)N5C(=O)C6CCCN6C(=O)C5(C4O)O)C;
Properties
Chemical formula	C27H33N3O7
Molar mass	511.575 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Verruculogen is a mycotoxin produced by certain strains of aspergillus that belongs to a class of naturally occurring 2,5-diketopiperazines.^[1] 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.^[2]

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.^[3]

References

^ Borthwick AD (2012). "2,5-Diketopiperazines: Synthesis, Reactions, Medicinal Chemistry, and Bioactive Natural Products". Chemical Reviews. 112 (7): 3641–3716. doi:10.1021/cr200398y. PMID 22575049.
^ "Verruculogen from Penicillium verruculosum". sigmaaldrich.com. Retrieved 25 September 2023.
^ Feng Y, Holte D, Zoller J, Umemiya S, Simke LR, Baran PS (August 2015). "Total Synthesis of Verruculogen and Fumitremorgin A Enabled by Ligand-Controlled C–H Borylation". Journal of the American Chemical Society. 137 (32): 10160–10163. doi:10.1021/jacs.5b07154. PMC 4777340. PMID 26256033.

[1] Borthwick AD (2012). "2,5-Diketopiperazines: Synthesis, Reactions, Medicinal Chemistry, and Bioactive Natural Products". Chemical Reviews. 112 (7): 3641–3716. doi:10.1021/cr200398y. PMID 22575049.

[2] "Verruculogen from Penicillium verruculosum". sigmaaldrich.com. Retrieved 25 September 2023.

[pmid226256033-3] Feng Y, Holte D, Zoller J, Umemiya S, Simke LR, Baran PS (August 2015). "Total Synthesis of Verruculogen and Fumitremorgin A Enabled by Ligand-Controlled C–H Borylation". Journal of the American Chemical Society. 137 (32): 10160–10163. doi:10.1021/jacs.5b07154. PMC 4777340. PMID 26256033.

[1]

[2]

[3]