17-Hydroxybrevianamide N And Its N1-Methyl Derivative, Quinazolinones From A Soft-Coral-Derived Aspergillus Sp. Fungus: 13s Enantiomers As The True Natural Products

Under the guidance of MS/MS-based molecular networking and HPLC-UV, two new alkaloid racemates, (+/-)-17-hydroxybrevianamide N (1) and (+/-)-N1-m e thyl-17-hydroxybrevianamide N (2), featuring a rare o-hydroxyphenylalanine residue and an imide subunit, were isolated from a soft-coral-derived Aspergillus sp. fungus. The true natural products (+)-1 and (+)-2 were further monitored and obtained from the freshly prepared EtOAc extracts, while (-)-1 and (-)-2 are artifacts generated during extraction and purification processes. Simultaneously, the structures including absolute configurations of (+)-13S-1, (-)-13R-1, (+)-13S-2, and (-)-13R-2 were elucidated on the basis of comprehensive spectroscopic analysis, ECD calculations, and X-ray diffraction data. Interestingly, basic solution promotes the racemization of (+)-1 and (-)-1, whereas acidic solution suppresses the transformation. The current research was concerned with the true natural products and their artifacts, providing critical insight into the isolation and identification of natural products.