Glioperazine B, as a new antimicrobial agent against Staphylococcus aureus, and glioperazine C: Two new dioxopiperazines from Bionectra byssicola

• Published in: Bioscience, biotechnology, and biochemistry Vol. 71; no. 8; pp. 1979 - 1983
• Main Authors: Zheng, C.J.(Korea Research Inst. of Bioscience and Biotechnology, Daejeon (Korea R.)), Kim, Y.H, Kim, W.G
• Format: Journal Article
• Language: English
• Published: Tokyo Japan Society for Bioscience, Biotechnology, and Agrochemistry 01.08.2007; Japan Society for Bioscience Biotechnology and Agrochemistry
• Subjects: Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - isolation & purification; Anti-Bacterial Agents - pharmacology; antibacterial; BACTERICIDAS; BACTERICIDE; BACTERICIDES; Biological and medical sciences; Bionectra byssicola; CHAMPIGNON; dioxopiperazine; Drug Resistance; Fundamental and applied biological sciences. Psychology; FUNGI; Fungi - chemistry; Fungi - metabolism; HONGOS; Indole Alkaloids - chemistry; Indole Alkaloids - isolation & purification; Indole Alkaloids - pharmacology; Methicillin - pharmacology; Microbial Sensitivity Tests; Molecular Structure; PIPERACINAS; PIPERAZINE; PIPERAZINES; Piperazines - chemistry; Piperazines - isolation & purification; Piperazines - pharmacology; Quinolones - pharmacology; STAPHYLOCOCCUS AUREUS; Staphylococcus aureus - drug effects; dioxopiperazine; Bacteria; Micrococcales; Micrococcaceae; antibacterial; Antibacterial agent; Bionectra byssicola; Antimicrobial agent; Staphylococcus aureus
• ISSN: 0916-8451; 1347-6947
• DOI: 10.1271/bbb.70167

In the course of our screening for new antibacterials from microbial metabolites, two new dioxopiperazine metabolites, glioperazines B (1) and C (2), together with the known compound, glioperazine (3), were isolated from the mycelia of a liquid fermentation culture of the fungus, Bionectra byssicola F120. The structures of compounds 1 and 2 were assigned on the basis of MS and NMR data. Compound 1 is an unusual dioxopiperazine metabolite containing an OMe group at the alpha-carbon of the amino acid residue. Compound 1 showed weak antibacterial activity against various strains of S. aureus, including methicillin-resistant S. aureus (MRSA) and quinolone-resistant S. aureus (QRSA), while 2 and 3 did not show such activity.