Biologically Active Echinulin-Related Indolediketopiperazines from the Marine Sediment-Derived Fungus Aspergillus niveoglaucus

Abstract

Seven known echinulin-related indolediketopiperazine alkaloids (1–7) were isolated from the Vietnamese sediment-derived fungus Aspergillus niveoglaucus. Using chiral HPLC, the enantiomers of cryptoechinuline B (1) were isolated as individual compounds for the first time. (+)-Cryptoechinuline B (1a) exhibited neuroprotective activity in 6-OHDA-, paraquat-, and rotenone-induced in vitro models of Parkinson’s disease. (−)-Cryptoechinuline B (1b) and neoechinulin C (5) protected the neuronal cells against paraquat-induced damage in a Parkinson’s disease model. Neoechinulin B (4) exhibited cytoprotective activity in a rotenone-induced model, and neoechinulin (7) showed activity in the 6-OHDA-induced model.

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

“…(−)-Cryptoechinuline B ( 212 ) and neoechinulin C ( 215 ) protected the Neuro-2a cells against paraquat toxicity. Neoechinulin B ( 214 ) exhibited cytoprotective activity against rotenone toxicity, and neoechinulin ( 213 ) showed activity against 6-OHDA [ 111 , 112 ].…”

“…SCSIO z015 Okinawa Trough, The East China Sea DPPH radical scavenging [ 107 ] Eurotiumins A–C ( 196 – 198 ) Eurotium sp. SCSIO F452 The South China Sea DPPH-radical scavenging [ 108 ] Eurotinoids A–C ( 199 – 204 ) [ 109 ] (+)-Dihydrocryptoechinulin D ( 205 ) Cytotoxicity (SF-268, HepG2) DPPH-radical scavenging (-)-Dihydrocryptoechinulin D ( 206 ) (+)-Euroticin B ( 207 ) Antioxidant activities [ 110 ] (–)-Euroticin B ( 208 ) Niveoglaucin A ( 209 ) Aspergillus niveoglaucus Nha Trang Bay, The South China Sea Suppression of ROS hyperproduction, Neuroprotective activity [ 111 ] Flavoglaucin ( 210 ) …”

“…New ergostanes, penicisteroids E (108), G(109) and H(110), together with known related penicisteroids A(111) and C(112) were isolated from Penicillium granulatum MCCC 3A00475 (Antarctica). Compounds 108-112 showed moderate antiproliferative effects selectively against 12 different cancer cell lines.…”

Molecular-biological and biomedical investigations in FEB RAS. Some modern results and perspectives of the marine natural products studies

“…Многие из них показали in vitro хорошую активность на различных моделях болезни Паркинсона. Было выделено два энантиомера криптоэхинулина В. Один из изомеров, (+)-криптоэхинулин B, демонстрировал хороший нейропротекторный эффект во всех экспериментах, а для его антипода такой эффект наблюдался только при использовании некоторых стимуляторов признаков этой болезни [9].…”

New Deoxyisoaustamide Derivatives from the Coral-Derived Fungus Penicillium dimorphosporum KMM 4689

“…Diketopiperazine alkaloids have shown various biological activities, including cytotoxic [ 10 , 11 , 12 , 13 ], antiphytopathogenic [ 14 ], anticancer [ 15 ] and neuroprotective effects [ 16 ]. Earlier it was reported that cryptoechinulin B and other echinuline-related compounds increased the viability of paraquat (PQ)-treated Neuro-2a cells, suppressing the upregulation of intracellular reactive oxygen species [ 17 ]. PQ is a bipyridyl quaternary ammonium herbicide and PQ poisoning is one of the leading intoxications worldwide.…”