ABSTRACT
Chemical investigation of an acetonitrile fraction from the endophytic fungus Phomopsis sp. led to the isolation of the new natural product 2-hydroxy-alternariol (7) together with the known compounds cytochalasins J (1) and H (2), 5'-epialtenuene (3) and the mycotoxins alternariol monomethyl ether (AME, 4), alternariol (AOH, 5) and cytosporone C (6). The structure of the new compound was elucidated by using 1-D and 2-D NMR (nuclear magnetic resonance) and high resolution mass spectrometry. The cytochalasins J (1) and H (2) and AOH (5) exhibited potent inhibition of the total ROS (reactive oxygen species) produced by stimulated human neutrophils and acted as potent potential anti-inflammatory agents. Moreover, cytochalasin H (2) demonstrated antifungal and acetylcholinesterase enzyme (AChE) inhibition in vitro.
Subject(s)
Anti-Inflammatory Agents, Non-Steroidal/pharmacology , Antifungal Agents/pharmacology , Ascomycota/metabolism , Anti-Inflammatory Agents, Non-Steroidal/chemistry , Antifungal Agents/chemistry , Antioxidants/chemistry , Antioxidants/pharmacology , Ascomycota/chemistry , Cholinesterase Inhibitors/chemistry , Cholinesterase Inhibitors/pharmacology , Cytochalasins/chemistry , Cytochalasins/pharmacology , Drug Evaluation, Preclinical/methods , Endophytes/metabolism , Humans , Lactones , Magnetic Resonance Spectroscopy , Molecular Structure , Mycotoxins/chemistry , Mycotoxins/metabolism , Neutrophils/drug effects , Neutrophils/metabolism , Reactive Oxygen Species/metabolism , Secondary Metabolism , Senna Plant/microbiology , Sesquiterpenes/chemistry , Sesquiterpenes/pharmacologyABSTRACT
A lignan with a new skeleton named chimarrhinin (1) was isolated from an extract of the leaves of Chimarrhis turbinata, a Rubiaceae plant species. (13)C NMR spectrometric techniques including 1D and 2D experiments and HRESIMS provided unequivocal structural confirmation of this new C(6).C(3) skeleton type. The relative configuration of 1 was established by 2D (1)H-H analysis and J couplings, while its conformation was evaluated through molecular modeling using the RM1 semiempirical method, with the aid of coupling constants obtained by NMR analysis. The antioxidant activity of the new derivative 1 and two known and previously isolated phenolic derivatives (2 and 3) was investigated. An IC(50) value of 7.50 ± 0.5 µmol L(-1) was obtained for the new derivative 1, while 2 and 3 showed IC(50) values of 18.60 ± 0.4 and 18.50 ± 0.6 µmol, respectively.
Subject(s)
Antioxidants/isolation & purification , Lignans/isolation & purification , Rubiaceae/chemistry , Antioxidants/chemistry , Antioxidants/pharmacology , Brazil , Lignans/chemistry , Lignans/pharmacology , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Plant Leaves/chemistryABSTRACT
Two unusual pyridine alkaloids, 7'-multijuguinone (1) and 12'-hydroxy-7'-multijuguinone (2), were isolated from the leaves of Senna multijuga, together with the known flavonoid rutin. The structures of the new alkaloids were established on the basis of spectroscopic data interpretation. Compounds 1 and 2 exhibited moderate in vitro acetylcholinesterase (AChE) inhibitory activity, in comparison with the standard compound physostigmine.
Subject(s)
Acetylcholinesterase/metabolism , Alkaloids/isolation & purification , Alkaloids/pharmacology , Cholinesterase Inhibitors/isolation & purification , Cholinesterase Inhibitors/pharmacology , Plants, Medicinal/chemistry , Pyridines/isolation & purification , Pyridines/pharmacology , Senna Plant/chemistry , Alkaloids/chemistry , Brazil , Cholinesterase Inhibitors/chemistry , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Plant Leaves/chemistry , Pyridines/chemistryABSTRACT
Bioactivity-guided fractionation of several bioactive exttracts obtained from Cerrado and Atlantic Forest plant species led to the isolation of potent DNA-damaging piperidine 1-5 and guanidine alkaloids 6-9 from Cassia leptophylla and Pterogyne nitens respectively, two common Leguminosae from Atlantic Forest. By means of biotechnological approach on Maytenus aquifolium, a species from Cerrado, moderate DNA-damaging sesquiterpene pyridine alkaloid 10-11 was isolated. Bioassay-guided fractionation on Casearia sylvestris, a medicinal plant species found in Cerrado and Atlantic Forest, led to the isolation of clerodane diterpenes 12-13 which showed effect on DNA. In addition, we have reported several interesting potent antifungal iridoids: 1beta-hydroxy-dihydrocornin (14), 1alpha-hydroxy-dihydrocornin (15), alpha-gardiol (16), beta-gardiol (17), plumericin (18), isoplumericin (19), 11-O-trans-caffeoylteucrein (20); ester derivative:2-methyl-4-hydroxy-butyl-caffeoate (21), amide N-[7-(3ï, 4ï-metrylenedioxyphenyl)-2Z, 4Z-heptadienoyl] pyrrolidine (22) and triterpene viburgenin (23).
