170713-71-0

Aureusimine B, also known as phevalin, is a natural pyrazinone produced by certain fungi and by Staphylococcus spp., including S. aureus. Its synthesis appears to be initiated by a conserved nonribosomal peptide synthetase that creates a dipeptide (phenylalanine-valine) aldehyde, which then undergoes cyclization and oxidation. Aureusimine B inhibits calpain in a casein hydrolysis assay (IC₅₀ = 1.3 μM), contributes to S. aureus infection in mice, and alters human keratinocyte gene expression.

Aureusimine B (phevalin) is a small molecular weight monoketopiperazine formed non-ribosomally by the fusion of phenylalanine and valine. Aureusimine B was isolated from S. aureus in 2010 as one of a pair of related metabolites, controversially identified as virulence factors in the pathology of Golden Staph. Aureusimine B is also an inhibitor of the protease, calpain.

Aureusimine B is a novel small molecule isolated from S. aureus as one of a pair of related metabolites controversially identified as virulence factors in the pathology of Golden Staph. Aureusimine B has also been reported as an inhibitor of the protease, calpain.

ChEBI: Phevalin is a member of the class of pyrazinones that is pyrazin-2(1H)-one substituted by an isopropyl and benzyl groups at position 3 and 6, respectively. It is a natural product found in Staphylococcus aureus that inhibits calpain in a casein hydrolysis assay (IC50 = 1.3 muM), contributes to S. aureus infection in mice, and alters human keratinocyte gene expression. It has a role as a bacterial metabolite and a calpain inhibitor. It is a member of benzenes and a pyrazinone.

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[1] M E ALVAREZ. Phevalin, a new calpain inhibitor, from a Streptomyces sp.[J]. Journal of Antibiotics, 1995, 48 10: 1165-1167. DOI: 10.7164/antibiotics.48.1165
[2] MICHAEL ZIMMERMANN  Michael A F. A family of pyrazinone natural products from a conserved nonribosomal peptide synthetase in Staphylococcus aureus.[J]. Chemistry & biology, 2010: 925-930. DOI: 10.1016/j.chembiol.2010.08.006
[3] PATRICK R SECOR. Phevalin (aureusimine B) production by Staphylococcus aureus biofilm and impacts on human keratinocyte gene expression.[J]. ACS Applied Bio Materials, 2012: e40973. DOI: 10.1371/journal.pone.0040973
[4] MORGAN A. WYATT. Staphylococcus aureus Nonribosomal Peptide Secondary Metabolites Regulate Virulence[J]. Science, 2010, 329 5989. DOI: 10.1126/science.1188888