ABSTRACT
A new diphenolic derivative asperdiphenol A (1), along with nine known compounds (2-10), was isolated from the marine-derived fungus Aspergillus niger 102. Their structures were elucidated on the basis of spectroscopic analysis including NMR and MS spectrometry. Compound 1 was suggested to be a chiral mixture by the specific rotation and chiral HPLC. Compound 1 was evaluated for its anti-inflammatory, antibacterial, and cytotoxic activity.
Subject(s)
Aspergillus niger/metabolism , Cyclopentanes/isolation & purification , Phenols/isolation & purification , Animals , Cell Line, Tumor , Cyclopentanes/chemistry , Cyclopentanes/pharmacology , Fermentation , Magnetic Resonance Spectroscopy , Marine Biology , Mice , Phenols/chemistry , Phenols/pharmacology , RAW 264.7 CellsABSTRACT
Two undescribed prenylbenzaldehyde derivatives, cristaldehydes A and B, and an undescribed quinone derivative, cristaquinone A, along with seven known compounds were isolated from the fungus Eurotium cristatum. The structures of undescribed compounds were determined by spectroscopic analysis including NMR, HR-ESIMS, and single-crystal X-ray diffraction. This is the first report of identification of a dibenzannulated 6,6-spiroketal derivative, cristaldehyde B, in a natural product. Cytotoxic and anti-inflammatory activities of all compounds were evaluated. Cristaldehyde A and cristaquinone A along with five known compounds showed significant anti-inflammatory activities with IC50 values in the range from 0.37 to 14.50⯵M.
Subject(s)
Anti-Inflammatory Agents, Non-Steroidal/chemistry , Anti-Inflammatory Agents, Non-Steroidal/pharmacology , Benzaldehydes/chemistry , Benzaldehydes/pharmacology , Eurotium/chemistry , Animals , Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Cell Line, Tumor , Crystallography, X-Ray , Drug Evaluation, Preclinical/methods , Humans , Inhibitory Concentration 50 , Magnetic Resonance Spectroscopy , Mice , Molecular Structure , RAW 264.7 Cells , Spectrometry, Mass, Electrospray IonizationABSTRACT
Five new naphthalenones, two enantiomers (−)-1 and (+)-1 leptothalenone A, (−)-4,8-dihydroxy-7-(2-hydroxy-ethyl)-6-methoxy-3,4-dihydro-2H-naphthalen-1-one ((−)-2), (4S, 10R, 4’S)-leptotha-lenone B (5), (4R, 10S, 4’S)-leptothalenone B (6), and a new isocoumarine, 6-hydroxy-5,8-dimethoxy-3-methyl-1H-isochromen-1-one (4), along with two known compounds (+)-4,8-dihydroxy-7-(2-hydroxy-ethyl)-6-methoxy-3,4-dihydro-2H-naphthalen-1-one ((+)-2) and (+)-10-norparvulenone (3) were isolated from the marine-derived fungus Leptosphaerulina chartarum 3608. The structures of new compounds were elucidated by HR-ESIMS, NMR, and ECD analysis. All compounds were evaluated for cytotoxicity and anti-inflammatory activity. Compound 6 showed moderate anti-inflammatory activity by inhibiting the production of nitric oxide (NO) in lipopolysaccharide-stimulated RAW264.7 cells, with an IC50 value of 44.5 μM.
Subject(s)
Anti-Inflammatory Agents, Non-Steroidal/isolation & purification , Aquatic Organisms/chemistry , Ascomycota/chemistry , Drug Discovery , Macrophages/drug effects , Naphthalenes/isolation & purification , Animals , Anti-Inflammatory Agents, Non-Steroidal/chemistry , Anti-Inflammatory Agents, Non-Steroidal/pharmacology , Aquatic Organisms/growth & development , Aquatic Organisms/isolation & purification , Ascomycota/growth & development , Ascomycota/isolation & purification , Cell Line, Tumor , China , Chromatography, High Pressure Liquid , Echinodermata/growth & development , Echinodermata/microbiology , Humans , Macrophages/immunology , Macrophages/metabolism , Magnetic Resonance Spectroscopy , Mice , Molecular Structure , Naphthalenes/chemistry , Naphthalenes/pharmacology , Naphthols/chemistry , Naphthols/isolation & purification , Naphthols/pharmacology , Pacific Ocean , RAW 264.7 Cells , Spectrometry, Mass, Electrospray Ionization , StereoisomerismABSTRACT
Two new sesquiterpenes, leptoterpenes A (1) and B (2) were isolated from the fungus Leptosphaerulina Chartarum sp. 3608, derived from a crinoid. It was the first chemical study on this species. The structures of these compounds were elucidated by spectroscopic methods including NMR and MS spectrometry. The absolute configurations of the new compounds were determined on the basis of the single-crystal X-ray diffraction and electronic circular dichroism data analysis. All compounds were tested for their anti-inflammatory activity and the inhibitory effects on Tyrosyl DNA phosphodiesterase II (TDP2).
