ABSTRACT
Six new α-pyrone meroterpenoid chevalones H-M (1-6), together with six known compounds (7-12), were isolated from the gorgonian coral-derived fungus Aspergillus hiratsukae SCSIO 7S2001 collected from Mischief Reef in the South China Sea. Their structures, including absolute configurations, were elucidated on the basis of spectroscopic analysis and X-ray diffraction data. Compounds 1-5 and 7 showed different degrees of antibacterial activity with MIC values of 6.25-100 µg/mL. Compound 8 exhibited potent cytotoxicity against SF-268, MCF-7, and A549 cell lines with IC50 values of 12.75, 9.29, and 20.11 µM, respectively.
Subject(s)
Anthozoa , Anti-Bacterial Agents/pharmacology , Antineoplastic Agents/pharmacology , Aspergillus , Pyrones/pharmacology , Animals , Anti-Bacterial Agents/chemistry , Antineoplastic Agents/chemistry , Aquatic Organisms , Cell Line, Tumor , China , Humans , Inhibitory Concentration 50 , Microbial Sensitivity Tests , Pyrones/chemistryABSTRACT
Three new tricyclic cyclopiazonic acid (CPA) related alkaloids asperorydines N-P (1-3), together with six known compounds (4-9) were isolated and characterized from the fungus Aspergillus flavus SCSIO F025 derived from the deep-sea sediments of South China Sea. The structures including absolute configurations of 1-3 were deduced from spectroscopic data, X-ray diffraction analysis, and electronic circular dichroism (ECD). All compounds were evaluated for the antioxidative activities against DPPH, cytotoxic activities against four tumor cell lines (SF-268, HepG-2, MCF-7, and A549), and antimicrobial activities. Compound 9 showed significant radical scavenging activities against DPPH with an IC50 value of 62.23 µM and broad-spectrum cytotoxicities against four tumor cell lines with IC50 values ranging from 24.38 to 48.28 µM. Furthermore, compounds 4-9 exhibited weak antimicrobial activities against E scherichia coli, and compound 9 also showed antibacterial activity against Bacillus thuringiensis, Micrococcus lutea, Staphylococcus aureus, Bacillus subtilis, Methicillin resistant Staphylococcus aureus.
Subject(s)
Alkaloids/pharmacology , Anti-Bacterial Agents/pharmacology , Antineoplastic Agents/pharmacology , Aspergillus flavus/chemistry , Indoles/pharmacology , Alkaloids/isolation & purification , Anti-Bacterial Agents/isolation & purification , Antineoplastic Agents/isolation & purification , Aquatic Organisms/chemistry , Bacillus/drug effects , Cell Line, Tumor , China , Escherichia coli/drug effects , Geologic Sediments/microbiology , Humans , Indoles/isolation & purification , Methicillin-Resistant Staphylococcus aureus/drug effects , Microbial Sensitivity Tests , Micrococcus/drug effects , Molecular Structure , Seawater/microbiologyABSTRACT
A new butenolide derivative (±)-asperteretal F (1) and related congener (2) recently reported containing an unusual 2-benzyl-3-phenyl substituted lactone core, together with five known compounds (3-7) were isolated and characterized from the fungus Aspergillus terreus. SCSIO FZQ028 derived from a deep-sea sediment of South China Sea. Their chemical structures were established on the basis of 1D- and 2D-NMR spectroscopic data, and HR-ESI-MS analysis. Additionally, all the compounds were evaluated for the antioxidative activities against DPPH, cytotoxic activities against two tumor cell lines (SF-268 and HepG-2), and antimicrobial activities. Compounds 2-4, and 7 showed significant activities against DPPH with IC50 ranging from 5.89 to 10.07 µg/mL. Compounds 2 and 4 showed moderate antimicrobial activities against all four tested bacteria.[Figure: see text].
Subject(s)
4-Butyrolactone/analogs & derivatives , Anti-Infective Agents/isolation & purification , Antineoplastic Agents/isolation & purification , Antioxidants/isolation & purification , Aspergillus/chemistry , 4-Butyrolactone/chemistry , 4-Butyrolactone/isolation & purification , 4-Butyrolactone/pharmacology , Anti-Infective Agents/chemistry , Anti-Infective Agents/pharmacology , Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Antioxidants/chemistry , Antioxidants/pharmacology , Bacteria/drug effects , Cell Line, Tumor , China , Fungi , Humans , Magnetic Resonance Spectroscopy , Mass Spectrometry , Molecular StructureABSTRACT
Three new prenylated indole 2,5-diketopiperazine alkaloids (1â»3) with nine known ones (5â»13), one new indole alkaloid (4), and one new bis-benzyl pyrimidine derivative (14) were isolated and characterized from the marine-derived fungus Eurotium sp. SCSIO F452. 1 and 2, occurring as a pair of diastereomers, both presented a hexahydropyrrolo[2,3-b]indole skeleton. Their chemical structures, including absolute configurations, were elucidated by 1D and 2D NMR, HRESIMS, quantum chemical calculations of electronic circular dichroism, and single crystal X-ray diffraction experiments. Most isolated compounds were screened for antioxidative potency. Compounds 3, 5, 6, 7, 9, 10, and 12 showed significant radical scavenging activities against DPPH with IC50 values of 13, 19, 4, 3, 24, 13, and 18 µM, respectively. Five new compounds were evaluated for cytotoxic activities.
