Bioactive Indolyl Diketopiperazines from the Marine Derived Endophytic Aspergillus versicolor DY180635

Abstract

<jats:p>Four new indolyl diketopiperazines, aspamides A–E (1–4) and two new diketopiperazines, aspamides F–G (5–6), along with 11 known diketopiperazines and intermediates were isolated from the solid culture of Aspergillus versicolor, which is an endophyte with the sea crab (Chiromantes haematocheir). Further chiral high-performance liquid chromatography resolution gave enantiomers (+)- and (−)-4, respectively. The structures and absolute configurations of compounds 1–6 were determined by the comprehensive analyses of nuclear magnetic resonance (NMR), high-resolution mass spectrometry (HR-MS), and electronic circular dichroism (ECD) calculation. All isolated compounds were selected for the virtual screening on the coronavirus 3-chymoretpsin-like protease (Mpro) of Severe Acute Respiratory Syndrome Coronavirus 2 (SARS-CoV-2), and the docking scores of compounds 1–2, 5, 6, 8 and 17 were top among all screened molecules, may be helpful in fighting with Corona Virus Disease-19 (COVID-19) after further studies.</jats:p>

Bioactive Indole Diketopiperazine Alkaloids from the Marine Endophytic Fungus Aspergillus sp. YJ191021

“…In summary, six new prenylated indole diketopiperazine alkaloids, asperthrins A-F (1-6), along with eight known analogues (7)(8)(9)(10)(11)(12)(13)(14), were isolated from the solid rice cultures of the marine-derived fungus Aspergillus sp. YJ191021.…”

“…In this study, we described the isolation and structure identification of six new prenylated indole diketopiperazine alkaloids (1)(2)(3)(4)(5)(6), together with eight known analogues: Gartryprostatin A (7) [15], gartryprostatin B (8) [15], sclerotiamide (9) [16], notoamide H (10) [17], 6-epi-notoamide R (11) [18], notoamide R (12) [19], (-)-notoamide I (13) [20], and gartryprostatin C (14) [15] (Figure 1) from the marine-derived endophytic fungus Aspergillus sp. YJ191021.…”

“…Various endophytic fungi have drawn substantial attention due to their potential to produce chemically diverse and biologically active secondary metabolites with anti-cancer, anti-microbial, anti-viral, and insecticidal activities [ 3 , 4 , 5 , 6 ]. In our continuous searching for novel bioactive secondary metabolites from marine endophytic fungi [ 7 , 8 , 9 ], the Aspergillus sp. YJ191021 attracted our attention, not only for the characteristic indole diketopiperazine ultraviolet (UV) absorptions of the crude extracts, but also for their potent antimicrobial activities against agricultural pathogenic fungi.…”

Diketopiperazine Gels: New Horizons from the Self-Assembly of Cyclic Dipeptides

“…CDPs are indeed attracting interest as drug carriers, thanks to their demonstrated ability to cross membranes and penetrate cells [ 29 ]. Their aggregates can display fluorescence [ 30 ], and they are widely studied for their diverse biological activities [ 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 ], which make them promising for biomedical applications, as recently reviewed [ 39 ]. Further, they are being investigated also for optoelectronic [ 40 ] and catalytic [ 41 ] applications, as biodegradable and environmentally-friendly substitutes of more traditional options.…”

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.…”