A Diketopiperazine Dimer from a Marine-Derived Isolate of Aspergillus niger

• Published in: Journal of natural products (Washington, D.C.) Vol. 67; no. 12; pp. 2093 - 2095
• Main Authors: OVENDEN, Simon P. B., SBERNA, Gian, TAIT, R. Murray, WILDMAN, Howard G., PATEL, Rupal, LI, Bin, STEFFY, Kevin, NGUYEN, Natalie, MEURER-GRIMES, Barbara M.
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 01-12-2004; Glendale, AZ American Society of Pharmacognosy
• Subjects: Antibiotics, microbial producers, chemotherapic agents, antiseptics, disinfecting agents; Applied microbiology; Aspergillus niger; Aspergillus niger - chemistry; Australia; Biological and medical sciences; Chemotherapic agents; Chromatography, High Pressure Liquid; Chromones - chemistry; Chromones - isolation & purification; Coumarins - chemistry; Coumarins - isolation & purification; Diketopiperazines; Fundamental and applied biological sciences. Psychology; Marine; Microbiology; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Piperazines - chemistry; Piperazines - isolation & purification; Australia; Angular nitrogen heterocycle; Lactam; Tetracyclic compound; Fungi; Marine environment; Microbial origin; Aspergillus niger; Absolute configuration; Antiviral; Isolation; Aromatic compound; Dimer; Fungi Imperfecti; Thallophyta; Structural analysis
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np0497494

The new diketopiperazine dimer 1, as well as the known compounds TMC-256A1 (2), TMC-256C1 (3), and demethylkotanin (4), were isolated from a culture of Aspergillus niger. The gross structure of 1 was determined by 2D NMR studies and comparison with literature data, and the absolute stereochemistry was elucidated by chiral HPLC analysis of the hydrolysis products.