ABSTRACT
Continued interest in bioactive alkaloids led to the isolation of two undescribed alkaloids, ophiorrhines F (1) and G (2), from the aerial parts of Ophiorrhiza japonica. Their structures were elucidated based on spectroscopic methods, electronic circular dichroism, and calculated NMR with DP4+ analysis. These two alkaloids represent key biological genetic intermediates in the formation of ring C in the ophiorrhines. Compound 1 exhibited good inhibition on LPS-induced B cell proliferation with an IC50 value of 0.38 µM and showed significant selective inhibitory activity on a B cell proliferation response with a selective index of 548.42. A preliminary study indicated that 1 may have a new mechanism of immunosuppression.
Subject(s)
Alkaloids , Rubiaceae , Alkaloids/chemistry , Alkaloids/pharmacology , Cell Proliferation , Immunosuppressive Agents/pharmacology , Molecular Structure , Rubiaceae/chemistryABSTRACT
Three new vibralactone derivatives, namely vibralactones U-W (1-3), together with vibralactone (4), have been isolated from cultures of the basidiomycete Boreostereum vibrans. Their structures were determined on the basis of spectroscopic methods and literature data. All compounds showed no activities to five human cancer cell lines.
Subject(s)
Antibiotics, Antineoplastic/chemistry , Antibiotics, Antineoplastic/pharmacology , Basidiomycota/chemistry , Lactones/chemistry , Lactones/pharmacology , Cell Line, Tumor , Drug Screening Assays, Antitumor , Humans , Molecular Structure , Nuclear Magnetic Resonance, BiomolecularABSTRACT
The first chain-Like vibralactone derivative, vibralactone Z4 (1), together with three known ones (2-4), were isolated from cultures of the basidiomycete Boreostereum vibrans. Vibralactone Z4 (1) is likely to be a key intermediate from 3 to 4 in their biosynthetic pathway. It showed a weak cytotoxicity to human cancer cell line SW480 (IC50 29.2 ± 1.38 µM).
Subject(s)
Antineoplastic Agents/pharmacology , Basidiomycota/metabolism , Lactones/metabolism , Lactones/pharmacology , Antineoplastic Agents/chemistry , Basidiomycota/cytology , Biosynthetic Pathways , Cell Line, Tumor , Drug Screening Assays, Antitumor , Humans , Lactones/chemistry , Magnetic Resonance Spectroscopy , Molecular Structure , Spectrometry, Mass, Electrospray IonizationABSTRACT
Two monoterpenoid indole alkaloids, ophiorrhines A (1) and B (2), were obtained from plant Ophiorrhiza japonica BI. Their structures were elucidated by extensive spectroscopic methods and single crystal X-ray diffraction. Compounds 1 and 2 possess a novel spirocyclic ring system. Its biosynthesis pathway is proposed. Compound 2 exhibits potent inhibitory activity against concanavalin A (Con A) induced T cell proliferation and lipopolysaccharide (LPS) induced B lymphocyte cell proliferation with IC50 values 13.3 and 7.5 µM, respectively. Compound 1 exhibits significant inhibition specifically against the LPS-induced proliferation of B lymphocyte cells with IC50 value 18.6 µM.
Subject(s)
Leukemia, B-Cell/drug therapy , Rubiaceae/chemistry , Secologanin Tryptamine Alkaloids/pharmacology , Cell Line, Tumor , Cell Proliferation/drug effects , Dose-Response Relationship, Drug , Humans , Leukemia, B-Cell/chemically induced , Leukemia, B-Cell/pathology , Lipopolysaccharides/antagonists & inhibitors , Lipopolysaccharides/pharmacology , Molecular Structure , Secologanin Tryptamine Alkaloids/chemistry , Secologanin Tryptamine Alkaloids/isolation & purification , Structure-Activity RelationshipABSTRACT
Five vibralactone derivatives containing γ, δ, ε-lactone cores, namely vibralactones X (1), Y (2), and Z1-Z3 (3-5), together with the known vibralactone, have been isolated from cultures of the basidiomycete Boreostereum vibrans. Compounds 3-5 possessed a novel bis-γ-lactone group which was found in vibralactone derivatives for the first time. Compounds 3 and 5 exhibited moderate cytotoxicities to human cancer cell lines referring to that of cisplatin.
Subject(s)
Antineoplastic Agents/isolation & purification , Basidiomycota/chemistry , Lactones/isolation & purification , Antineoplastic Agents/pharmacology , Cell Line, Tumor , Humans , Lactones/pharmacology , Molecular StructureABSTRACT
Three new podocarpane diterpenoids, namely anemhupehins A-C (1-3), together with four known analogues (4-7), have been isolated from aerial parts of Anemone hupehensis. Their structures were characterized based on extensive spectroscopic data. Compounds 1 and 4 showed certain cytotoxicities against human cancer cell lines.
