ABSTRACT
Lycodine-type alkaloids have gained significant interest owing to their unique skeletal characteristics and acetylcholinesterase activity. This study established a rapid and reliable method using ultra-performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry (UPLC-ESI-Q/TOF-MS/MS) for comprehensive characterization of lycodine-type alkaloids for the first time. The lycodine-type alkaloids were detected successfully from Lycopodiastrum casuarinoides, Huperzia serrata and Phlegmarirus carinatus in seven plants of the Lycopodiaceae and Huperziaceae families, based on the established characteristic MS fragmentation of five known alkaloids. Furthermore, a total of 13 lycodine-type alkaloids were identified, of which three pairs of isomers were structurally characterized and differentiated. This study further improves mass analysis of lycodine-type alkaloids and demonstrates the superiority of UPLC with a high-resolution mass spectrometer for the rapid and sensitive structural elucidation of other trace active compounds. Copyright © 2016 John Wiley & Sons, Ltd.
Subject(s)
Alkaloids/analysis , Chromatography, High Pressure Liquid/methods , Heterocyclic Compounds, 4 or More Rings/analysis , Lycopodiaceae/chemistry , Plant Extracts/chemistry , Huperzia/chemistry , Spectrometry, Mass, Electrospray Ionization/methods , Tandem Mass Spectrometry/methodsABSTRACT
Relying on characteristic double UV absorptions (210 and 270 nm), sixteen phragmalins with three types of enolic acyl substituents at C-15 were isolated directly from EtOH extracts of the seeds of Chukrasia tabularis A. Juss. Eight of these compounds possessed a C-15-acetyl phragmalin skeleton, and the basic carbon skeleton and absolute configuration of one of these was determined by NMR and X-ray diffraction analysis, while the structures of the other phragmalins were determined via NMR, HR-MS, and CD spectra. Additionally, all of the isolates were tested for inhibition against lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW264.7 macrophages and cytotoxicity in SMMC-7721, MCF-7 and U2OS tumor cells.
Subject(s)
Limonins/chemistry , Meliaceae/chemistry , Animals , Cell Line/drug effects , Circular Dichroism , Crystallography, X-Ray , Drug Evaluation, Preclinical/methods , Humans , Limonins/pharmacology , Lipopolysaccharides/pharmacology , MCF-7 Cells/drug effects , Macrophages/drug effects , Macrophages/metabolism , Magnetic Resonance Spectroscopy , Mice , Molecular Structure , Nitric Oxide/metabolism , Spectrophotometry, UltravioletABSTRACT
Six new cassane diterpenoids, named caesalls H-M (1-6), were isolated from the seed kernels of Caesalpinia bonduc. Their structures were elucidated on the basis of spectroscopic analysis, mainly NMR and MS. The absolute configurations of compounds 1 and 3 were determined by a single-crystal X-ray study using a mirror CuKα radiation and circular dichroism (CD) spectra, respectively. None of the compounds were cytotoxic against HepG-2, MCF-7 and MG-63 cells.
Subject(s)
Caesalpinia/chemistry , Diterpenes/chemistry , Caesalpinia/metabolism , Cell Line, Tumor , Cell Survival/drug effects , Circular Dichroism , Crystallography, X-Ray , Diterpenes/isolation & purification , Diterpenes/toxicity , Hep G2 Cells , Humans , MCF-7 Cells , Magnetic Resonance Spectroscopy , Molecular Conformation , Seeds/chemistry , Seeds/metabolismABSTRACT
Psycacoraone A (1), a new acorane-type sesquiterpene possessing rare spirobicyclic carbon skeleton, was isolated from the aerial parts of Psychotria yunnanensis. Its structure was elucidated on the basis of spectroscopic methods including HR-ESI-MS, 1D and 2D NMR. The absolute configuration of 1 was determined by calculation of electronic circular dichroism using density functional theory.
Subject(s)
Plant Components, Aerial/chemistry , Psychotria/chemistry , Sesquiterpenes/chemistry , Animals , Cell Line , Macrophages/drug effects , Mice , Molecular Structure , Nitric Oxide/biosynthesis , Sesquiterpenes/isolation & purificationABSTRACT
Two new neo-clerodane diterpenoids, teucvisins A and B (1, 2), and three new 19-nor-neoclerodane diterpenoids, teucvisins C-E (3-5), together with ten known constituents (6-15) were isolated from the whole plants of Teucrium viscidum. All the isolates were evaluated for their inhibitory activities of lipopolysaccharide (LPS)-induced nitric oxide production in RAW264.7 macrophages. The results indicated that compounds 11 and 15 showed moderate inhibition with an IC50 value of 21.9 and 22.4 µM, respectively.
Subject(s)
Diterpenes, Clerodane/pharmacology , Macrophages/drug effects , Teucrium/chemistry , Animals , Diterpenes, Clerodane/chemistry , Diterpenes, Clerodane/isolation & purification , Dose-Response Relationship, Drug , Lipopolysaccharides/antagonists & inhibitors , Lipopolysaccharides/pharmacology , Macrophages/metabolism , Mice , Molecular Structure , Nitric Oxide/antagonists & inhibitors , Nitric Oxide/biosynthesis , Structure-Activity RelationshipABSTRACT
Six new withanolides (1-6), including two uncommon 1,10-seco withanolides (1 and 2), together with five known withanolides (7-11), were isolated from the whole plants of Physalis minima Linn.. The structures of new compounds were elucidated through spectroscopic methods, including (1)H, (13)C NMR, 2D-NMR, HRESIMS and circular dichroism (CD). Inhibitory effects of the isolates on nitric oxide (NO) production in lipopolysaccaride-activated RAW264.7 macrophages were evaluated. Compounds 2 and 5 showed strong inhibitory activities with IC50 values of 8.04 and 10.01 µM, respectively. Compounds 1, 9 and 10 exhibited moderate inhibitory activities with IC50 values from 25.54 to 43.58 µM.
Subject(s)
Nitric Oxide/antagonists & inhibitors , Physalis/chemistry , Plant Extracts/pharmacology , Withanolides/pharmacology , Animals , Cell Line , Dose-Response Relationship, Drug , Lipopolysaccharides/antagonists & inhibitors , Lipopolysaccharides/pharmacology , Macrophages/drug effects , Macrophages/metabolism , Mice , Molecular Conformation , Nitric Oxide/biosynthesis , Plant Extracts/chemistry , Plant Extracts/isolation & purification , Structure-Activity Relationship , Withanolides/chemistry , Withanolides/isolation & purificationABSTRACT
Panax ginseng C.A. Meyer has been known as a valuable traditional Chinese medicines for thousands years of history. Ginsenosides, the main active constituents, exhibit prominent immunoregulation effect. The present study first describes a holistic method based on chemical characteristic and lymphocyte proliferative capacity to evaluate systematically the quality of P. ginseng in thirty samples from different seasons during 2-6 years. The HPLC fingerprints were evaluated using principle component analysis (PCA) and hierarchical clustering analysis (HCA). The spectrum-efficacy model between HPLC fingerprints and T-lymphocyte proliferative activities was investigated by principal component regression (PCR) and partial least squares (PLS). The results indicated that the growth of the ginsenosides could be grouped into three periods and from August of the fifth year, P. ginseng appeared significant lymphocyte proliferative capacity. Close correlation existed between the spectrum-efficacy relationship and ginsenosides Rb1, Ro, Rc, Rb2 and Re were the main contributive components to the lymphocyte proliferative capacity. This comprehensive strategy, providing reliable and adequate scientific evidence, could be applied to other TCMs to ameliorate their quality control.
Subject(s)
Ginsenosides/chemistry , Ginsenosides/pharmacology , Panax/chemistry , Animals , B-Lymphocytes/drug effects , Cell Proliferation/drug effects , Chromatography, High Pressure Liquid/methods , Cluster Analysis , Male , Principal Component Analysis , Quality Control , Rats , Rats, Sprague-Dawley , Seasons , T-Lymphocytes/drug effectsABSTRACT
Phytochemical investigation of the stem and bark of Trichilia connaroides led to the isolation of eight new nortriterpenoids (1-8), along with fifteen known compounds (9-23). Their structures were established based on extensive spectroscopic analysis. The absolute configuration of 2 was confirmed by X-ray crystallographic study. The nitric oxide production and α-glucosidase inhibitory effects for these isolates were evaluated: moderate to strong nitric oxide production inhibitory activities were found for 5, 6, and 11-15, with IC50 values ranging from 7.5 to 26.3 µM; marked α-glucosidase inhibitory effects were observed for 22 and 23, with IC50 values of 2.3 and 0.4 µM, respectively.
Subject(s)
Drugs, Chinese Herbal/chemistry , Glycoside Hydrolase Inhibitors , Meliaceae/chemistry , Nitric Oxide/biosynthesis , Triterpenes/chemistry , Animals , Cell Line , Crystallography, X-Ray , Drugs, Chinese Herbal/isolation & purification , Drugs, Chinese Herbal/pharmacology , Inhibitory Concentration 50 , Lignans , Medicine, Chinese Traditional , Molecular Structure , Plant Bark/chemistry , Plant Stems/chemistry , Plants, Medicinal , Triterpenes/isolation & purification , Triterpenes/pharmacologyABSTRACT
Six new benzofuran neolignans (1-6) were isolated from the EtOAc-soluble fraction of the aerial part of Aristolochia fordiana, together with twelve known analogues (7-18). The structures of the isolated compounds were elucidated by spectroscopic methods. All isolates were evaluated for their inhibitory effects on nitric oxide production in lipopolysaccaride-activated RAW264.7 macrophages and for their cytotoxic activities on three human cancer cell lines. Compound 2 showed significant nitric oxide production inhibitory activity with an IC50 value of 10.00 µM, while compound 16 exhibited cytotoxic activity with an IC50 value of 11.9 µM against MG-63 and compound 18 of 9.15 µM against HepG2 cell lines, respectively.
Subject(s)
Aristolochia/chemistry , Benzofurans/isolation & purification , Lignans/isolation & purification , Nitric Oxide/metabolism , Plant Extracts/isolation & purification , Animals , Benzofurans/chemistry , Benzofurans/pharmacology , Cell Line , Cell Line, Tumor , Cell Survival , Humans , Inhibitory Concentration 50 , Lignans/chemistry , Lignans/pharmacology , Lipopolysaccharides/pharmacology , Macrophages/drug effects , Mice , Molecular Structure , Plant Extracts/chemistry , Plant Extracts/pharmacology , Plants, MedicinalABSTRACT
Aphanamenes A (1) and B (2), two unprecedented acyclic diterpene dimers formed via a [4 + 2]-cycloaddition, were isolated from the root bark of Aphanamixis grandifolia. Their structures were elucidated by spectroscopic analyses, and the absolute configuration of 1 was determined by ECD calculations. Both 1 and 2 showed significant inhibition on NO production on lipopolysaccharide-induced RAW264.7 macrophages.
Subject(s)
Diterpenes/chemistry , Macrophages/drug effects , Nitrogen Oxides/antagonists & inhibitors , Plant Bark/chemistry , Plant Roots/chemistry , Cycloaddition Reaction , Diterpenes/isolation & purification , Macrophages/chemistry , Meliaceae/chemistry , Molecular StructureABSTRACT
Amomaxins A (1) and B (2), featuring an unprecedented rearranged labdane norditerpene skeleton with a nine-membered ring, along with their biosynthetic related known compound isocoronarin D (3) were isolated from the roots of Amomum maximum. Their structures with absolute configurations were determined by spectroscopic data, CD experimentation, and single-crystal X-ray diffraction. Compound 2 showed an inhibitory effect on nitric oxide (NO) production in lipopolysaccharide-induced RAW264.7 macrophages.
