Antibacterial Alkaloids and Polyketide Derivatives from the Deep Sea-Derived Fungus Penicillium cyclopium SD-413

Abstract

Nine secondary metabolites (1–9), including two new polyketide derivatives 9-dehydroxysargassopenilline A (4) and 1,2-didehydropeaurantiogriseol E (5), along with seven known related secondary metabolites (1–3 and 6–9), were isolated and identified from the deep sea-derived fungus Penicilliumcyclopium SD-413. Their structures were elucidated on the basis of 1D/2D NMR spectroscopic and mass spectrometric analysis and the absolute configurations were determined by the combination of NOESY correlations and time-dependent density functional (TDDFT) ECD calculations. Compounds 1–9 inhibited some pathogenic bacteria including Escherichia coli, E. ictaluri, Edwardsiella tarda, Micrococcus luteus, Vibrio anguillarum, and V. harveyi, with MIC (minimum inhibitory concentration) values ranging from 4 to 32 μg/mL.

Lithocarpins E—G, Potent Anti‐Tumor Tenellone‐Macrolides from the Deep‐Sea Fungus Phomopsis lithocarpusFS508

“…Deep‐sea marine fungi, surviving in the extreme environmental condition, is well regarded as a strategically treasure resource of pharmaceutically and industrially meaningful lead molecules, attributed to their diverse bioactivities such as antiallergic, [ 7 ] antibacterial, [ 8 ] and cytotoxic activities. [ 9 ] A plethora of natural products and their synthetic analogues derived from marine fungi were developed and clinically applied as chemotherapeutic drugs toward various cancers including phenylahistin, fingolimod, sorbicillactone A, and so on in recent years.…”

Uncommon N‐Methoxyindolediketopiperazines from Acrostalagmus luteoalbus, a Marine Algal Isolate of Endophytic Fungus

“…[ 3 ] IDPs are characterized by the condensation of a complete tryptophan and a second amino acid, and the potent bioactivities such as antimicrobial, [ 4 ] anticancer, [ 5 ] immunomodulatory, [ 6 ] antioxidant, [ 7 ] and insecticidal activities [ 8 ] have attracted considerable attention from chemists and/or pharmacologists. During our exploration for novel and active metabolites from marine‐related fungi, [ 9‐12 ] Acrostalagmus luteoalbus TK‐43, an algicolous endophytic fungus obtained from the freshly collected marine green alga Codium fragile , was selected for further chemical investigations. As a result, three pairs of IDP enantiomers (acrozines A—C) having uncommon N ‐methoxy substitutions were identified from the EtOAc extract of A. luteoalbus TK‐43.…”

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

“…The eutypellazines P-R (37-39) ( Figure 4) exhibited moderate inhibitory effects against Staphylococcus aureus and VRE [34]. Eutypellol A (40), the first norsesquiterpenoid of the sequicarene family, as well as eutypellol B (41), a rare 7-methyl oxidized 2-carene derivative, and new 2-(2-hydroxy-4-methylcyclohex-3-enyl)propanoic acid (42), along with eight known terpenoids, were isolated from Eutypella scoparia FS46 (the South China Sea). Compounds 40 and 41 showed a weak antibacterial activity against S. aureus [35].…”

“…9-Dehydroxysargassopenilline A ( 56 ) and 1,2-didehydropeaurantiogriseol E ( 57 ) were isolated from Penicillium cyclopium SD-413 (the East China Sea). Compounds inhibited growth of some pathogenic bacteria including Escherichia coli , E. ictaluri , Edwardsiella tarda , Micrococcus luteus , Vibrio anguillarum , and V. harveyi [ 42 ].…”

“…ZZ1283 Karachi, Pakistan, The Arabian Sea Antibacterial (MRSA, E. coli ), antifungal ( Candida albicans) [ 40 ] Penicyrone ( 52 ) Penicillium sp. Y-50-10 Kueishantao, Taiwan, The East China Sea Antibacterial (Bacillus subtilis) [ 41 ] Norpenicyrone ( 53 ) Methyl norpenicyrone ( 54 ) Methyl penicyrone ( 55 ) 9-Dehydroxysargassopenilline A ( 56 ) Penicillium cyclopium SD-413 The East China Sea Antibacterial (E. coli , E. ictaluri , Edwardsiella tarda , Micrococcus luteus , Vibrio anguillarum , and V. harveyi) [ 42 ] 1,2-Didehydropeaurantiogriseol E ( 57 ) Tyrosol ( 58 ) Penicillium chrysogenum DXY-1 Taiwan Strait Antibacterial (inhibitor of the quorum sensing (QS) system in Chromobacterium violaceum andPseudomonas aeruginosa, biofilm formation in P. aeruginosa ) [ 43 ] Penijanthines C ( ...…”