Bionectins A−C, Epidithiodioxopiperazines with Anti-MRSA Activity, from Bionectra byssicola F120

• Published in: Journal of natural products (Washington, D.C.) Vol. 69; no. 12; pp. 1816 - 1819
• Main Authors: Zheng, Chang-Ji, Kim, Chang-Jin, Bae, Kyung Sook, Kim, Young-Ho, Kim, Won-Gon
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.12.2006; Amer Chemical Soc; American Society of Pharmacognosy
• Subjects: Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - isolation & purification; Anti-Bacterial Agents - pharmacology; antibacterial properties; Antibiotics (antibacterial agents, antifungal agents); Antibiotics, microbial producers, chemotherapic agents, antiseptics, disinfecting agents; Applied microbiology; Biological and medical sciences; bionectin; Bionectra byssicola; chemical structure; Chemistry, Medicinal; epidithiodioxopiperazine; Fundamental and applied biological sciences. Psychology; Fungi - chemistry; Life Sciences & Biomedicine; Methicillin Resistance; Microbial Sensitivity Tests; Microbiology; Molecular Structure; Pharmacology & Pharmacy; Piperazines - chemistry; Piperazines - isolation & purification; Piperazines - pharmacology; Plant Sciences; Science & Technology; spectral analysis; Staphylococcus aureus; Staphylococcus aureus - drug effects; MARINE ALGA; CYTOTOXIC METABOLITES; LEPTOSINS; Pentacyclic compound; Sulfur nitrogen heterocycle; Nitrogen heterocycle; Lactam; Tetracyclic compound; In vitro; Biological activity; Meticillin; Fungi; Resistance; Disulfide bond; Bacteria; Micrococcales; Isolation; Micrococcaceae; Aromatic compound; Antibacterial agent; Indole derivatives; Mycelium; Quinolone derivatives; Staphylococcus aureus; Thallophyta; Structural analysis
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np060348t

Three new epidithiodioxopiperazine compounds, bionectins A (1), B (2), and C (3), along with a known compound, verticillin D (4), have been isolated from the mycelium of liquid fermentation cultures of the fungus Bionectra byssicola F120. The structures of compounds 1−3 were assigned on the basis of MS and NMR data. Compounds 1 and 2 incorporate a dioxopiperazine moiety with a disulfide bridge in their molecules, while 3 contains a dioxopiperazine ring with two methylsulfanyl groups. Compounds 1 and 2 exhibited antibacterial activity against S. aureus including methicillin-resistant S. aureus (MRSA) and quinolone-resistant S. aureus (QRSA), with MIC values of 10−30 μg/mL, while 3 showed no antibacterial activity even at 100 μg/mL.