Asperienes A–D, Bioactive Sesquiterpenes from the Marine-Derived Fungus Aspergillus flavus

Abstract

Marine-derived fungi of the genera Aspergillus could produce novel compounds with significant bioactivities. Among these fungi, the strain Aspergillus flavus is notorious for its mutagenic mycotoxins production. However, some minor components with certain toxicities from A. flavus have not been specifically surveyed and might have potent biological activities. Our investigation of the marine-derived fungus Aspergillus flavus CF13-11 cultured in solid medium led to the isolation of four C-6′/C-7′ epimeric drimane sesquiterpene esters, asperienes A–D (1–4). Their absolute configurations were assigned by electronic circular dichroism (ECD) and Snatzke’s methods. This is the first time that two pairs of C-6′/C-7′ epimeric drimane sesquiterpene esters have successfully been separated. Aperienes A–D (1–4) displayed potent bioactivities towards four cell lines with the IC50 values ranging from 1.4 to 8.3 μM. Interestingly, compounds 1 and 4 exhibited lower toxicities than 2 and 3 toward normal GES-1 cells, indicating more potential for development as an antitumor agent in the future.

Metabolites of Marine Sediment-Derived Fungi: Actual Trends of Biological Activity Studies

“…Penijanthines C (59) and D (60) as well as penijanthoids A (61) and B (62), products of Penicillium janthinellum (the Bohai Sea) metabolism, displayed significant activity against three pathogenic Vibrio spp. [44].…”

“…Asperienes A–D ( 86 – 89 ), C-6′/C-7′ epimeric drimane sesquiterpene esters, were isolated from Aspergillus flavus CF13-11 (the Bohai Sea). Compounds 86 – 89 displayed potent activities towards HeLa, MCF-7, MGC-803, and A549 cell lines [ 59 ].…”

Antibacterial Secondary Metabolites from Marine-Derived Fungus Aspergillus sp. IMCASMF180035

“…Fungi of the Aspergillus genus isolated from a marine environment have been proven to be rich sources for discovering new chemical entries with antibacterial and antifungal [ 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 ], inflammatory [ 19 ], antiviral [ 20 , 21 ], and antitumor [ 22 , 23 ] activities. During our ongoing search for novel bioactive secondary metabolites against bacteria and mycobacteria from marine-derived fungi, the crude extract of the fungus Aspergillus sp.…”

Antimicrobial Meroterpenoids and Erythritol Derivatives Isolated from the Marine-Algal-Derived Endophytic Fungus Penicillium chrysogenum XNM-12

“…Fungal secondary metabolites of marine origin have drawn considerable attention because of their unique chemical structures and potential pharmaceutical applications [ 1 , 2 , 3 ]. Marine-derived filamentous fungi have been proven to be more prolific sources of bioactive natural products than those found in land-based systems [ 4 , 5 , 6 , 7 , 8 , 9 ]. Marine-derived fungi can be distributed in all marine habitats, ranging from marine plants to marine invertebrates and vertebrates and from marine sediments to deep-sea hydrothermal and cold springs [ 2 , 6 , 7 , 8 ].…”

“…In our ongoing efforts to discover structurally unique and biologically active secondary metabolites from algal-derived endophytic fungi, the fungal strain Penicillium chrysogenum XNM-12 from the marine brown alga Leathesia nana (Chordariaceae) was chosen for further chemical investigation. Solid regime cultivation of P. chrysogenum XNM-12 led to the isolation of one new meroterpenoid-type alkaloid (1) and two new erythritol derivatives (6 and 7), as well as four known meroterpenoids (2)(3)(4)(5) (Figure 1). The planar structures of these new compounds were determined by detailed analyses of their spectroscopic data, and their absolute configurations were assigned by comparing the experimental and calculated electronic circular dichroism (ECD) spectra and optical rotations with literature data.…”