Three New Metabolites From the Marine-Derived Fungus Aspergillus sp. WHUF03110

Abstract

Two new xanthone derivatives, spinosusones A (1) and B (2), and a new tryptoquivaline analogue, asperdiazapinone G (3), together with nine known compounds (4-12) were isolated from the EtOAc extract of the marine-derived fungus Aspergillus sp . WHUF03110. The structures of 1-3 were determined by spectroscopic analysis, and comparison with literature data. Most of these isolated compounds were evaluated for their antimicrobial activities against ten Gram-negative and seven Gram-positive bacteria, Mycobacterium smegmatis ATCC 607, Candida albicans ATCC SC5314, and C. albicans YY-1-4. Compound 10 displayed strong antibacterial activity against five Gram-positive bacteria ( Bacillus subtilis 168, Staphylococcus aureus ATCC25923, S. aureus NEWMAN, S. aureus USA300, S. aureus NRS 271) with MIC values ranging from 1.0 to 2.0 μg/mL, and displayed moderate antibacterial activity against four Gram-negative bacteria ( Helicobacter pylori 26695, H. pylori G27, H. pylori 159, H. pylori 129) and M. smegmatis ATCC 607 with a MIC value of 8.0 μg/mL.

Marine-Derived Xanthone from 2010 to 2021: Isolation, Bioactivities and Total Synthesis

“…Then, the cultured broth is filtered and extracted, most often, with EtOAc. This extract is subjected to a vacuum liquid chromatography over a silica gel column [ 15 , 16 , 21 , 23 ], flash chromatography [ 19 ] or, most commonly, to normal column chromatography (CC) [ 14 , 17 , 18 , 20 , 22 ], originating different fractions, which can be subjected to analysis by HPLC or TLC, obtaining sub-fractions, or be directly purified to obtain pure compounds. Most of the xanthones herein referred to were obtained after semi-preparative HPLC purifications of these sub-fractions.…”

“…Naturally, the eluents and gradients used differ depending on the extracts/fractions being analyzed. The most common eluents used are organic solvents mixtures, such as n -hexane/CH 2 Cl 2 /MeOH [ 16 ], n -hexane/EtOAc [ 15 ], CH 2 Cl 2 /MeOH [ 15 , 18 , 20 , 21 , 23 ], gradient of petroleum ether/EtOAc [ 14 , 17 , 18 ], but mixtures of H 2 O/MeOH can also be used successfully [ 19 ].…”

“…The new xanthone derivatives isolated include simple ones ( Figure 2 ), mainly isolated from marine-derived fungi found in marine sediments [ 15 , 18 , 20 , 31 , 32 , 33 , 34 , 35 , 36 , 46 , 47 , 48 , 49 ]. These xanthones are usually highly substituted, with different substituent patterns being the substituents found to be essential for four types; hydroxy, methoxy, methyl, and methoxycarbonyl groups.…”

“…In addition, the marine environment, the least explored area of this planet, has also proven to be an invaluable source [ 10 , 11 ]. Many xanthones have been isolated from marine-derived fungi [ 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 ], which can be found in marine sediments and associated with other marine organisms [ 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , …”

“…These unique defenses can lead to the biosynthesis of new secondary metabolites, different from those synthesized by terrestrial sources [ 41 ]. The chemically different/unique structures allow xanthones to have important biological activities, such as cytotoxic [ 12 , 15 , 16 , 17 , 21 , 22 , 23 , 27 , 32 , 37 , 43 ], antibacterial [ 12 , 16 , 17 , 18 , 19 , 20 , 22 , 26 , 29 , 30 , 35 , 36 , 39 ], and antifungal [ 20 , 22 , 33 , 40 ] activities, giving them great potential as natural products with medicinal value [ 1 ].…”