Verruculogen

Last updated
Verruculogen
Verruculogen.svg
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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.162.193 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 634-189-1
KEGG
PubChem CID
  • 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
    Key: LRXYHMMJJCTUMY-UHFFFAOYSA-N
  • CC(=CC1N2C3=C(C=CC(=C3)OC)C4=C2C(CC(OO1)(C)C)N5C(=O)C6CCCN6C(=O)C5(C4O)O)C
Properties
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).

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

  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.
  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. Bibcode:2015JAChS.13710160F. doi:10.1021/jacs.5b07154. PMC   4777340 . PMID   26256033.
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