ABSTRACT
The chemical constituents from the stems and leaves of Artocarpus tonkinensis in Artocarpus of Moraceae were systematically studied by means of silica gel, octadecylsilyl(ODS), and Sephadex LH-20 gel column chromatographies, as well as preparative high-performance liquid chromatography(Pre-HPLC) and a variety of chromatographic separation techniques. The spectral data and physicochemical properties of the compounds were obtained from separation and compared with those of the compounds reported in the literature. As a result, 11 compounds isolated from the 90% ethanol extract of the stems and leaves of A. tonkinensis were identified as artocatonkine(1), 5,6,7,4'-tetramethoxyflavone(2), apigenin-4'-O-ß-D-glucoside(3), rayalinol(4), psorachalcone A(5), 4-ketopinoresinol(6), ficusesquilignan B(7), pinnatifidanin AI(8), pinnatifidanin A(9), O-methylmellein(10), and trans-4-hydroxymellein(11). Among these compounds, compound 1 was a new prenylated flavone, and compounds 2-11 were isolated from the plants belonging to the genus Artocarpus for the first time. Furthermore, all compounds 1-11 were evaluated for their anti-rheumatoid arthritis activities, and the MTS method was used to measure their inhibitory effects on the proliferation of synovioblasts in vitro. The results of activity evaluation showed that flavonoid compounds 1-3, 5, and lignan compounds 8 and 9 displayed significant anti-rheumatoid arthritis activities, showing the IC_(50) values in inhibiting the proliferation of synovioblasts MH7A from(6.38±0.06) µmol·L~(-1) to(168.58±0.28)µmol·L~(-1).
Subject(s)
Artocarpus , Cell Proliferation , Plant Leaves , Plant Stems , Artocarpus/chemistry , Plant Leaves/chemistry , Plant Stems/chemistry , Cell Proliferation/drug effects , Humans , Drugs, Chinese Herbal/pharmacology , Drugs, Chinese Herbal/chemistry , Cell Line , Molecular Structure , Chromatography, High Pressure LiquidABSTRACT
Four new xanthones, cratocochinones A-D (1-4), together with eight known analogues (5-12), were isolated from the stems and leaves of Cratoxylum cochinchinense. The chemical structures of cratocochinones A-D (1-4) were elucidated by comprehensive spectroscopic analyses and the known compounds were identified by comparisons with the spectral data reported in the literature. All isolated compounds 1-12 were evaluated for their anti-inflammatory activities and anti-HIV-1 activities. Compounds 1-12 showed remarkable inhibitory activities on nitric oxide (NO) production induced by lipopolysaccharide in mouse macrophage RAW 264.7 cells in vitro, with IC50 values in the range of 0.86 ± 0.05 to 18.36 ± 0.21 µM. Meanwhile, compounds 1-12 exhibited significant anti-HIV-1 activities with EC50 which ranged from 0.22 to 11.23 µM. These findings indicate that the discoveries of these xanthones, isolated from the stems and leaves of C. cochinchinense, showing significant anti-inflammatory and anti-HIV-1 effects could be of great importance to the research and development of new natural anti-inflammatory and anti-HIV agents.
Subject(s)
Anti-HIV Agents , Clusiaceae , HIV-1 , Xanthones , Animals , Mice , Plant Leaves , Anti-HIV Agents/pharmacology , Anti-Inflammatory Agents/pharmacology , Xanthones/pharmacologyABSTRACT
Bradina is a species-rich genus that differs from most other Spilomelinae genera because of its distinctive wing venation. Most species of this genus are very similar in appearance. In this study, we have studied morphological characteristics of the genus and eight closely related species from China. Among them, B.falciculata Guo & Du, sp. nov., B.fusoidea Guo & Du, sp. nov., B.spirella Guo & Du, sp. nov., B.ternifolia Guo & Du, sp. nov. and B.torsiva Guo & Du, sp. nov. are described as new to science. Bradinamegesalis (Walker, 1859), B.translinealis Hampson, 1896 and B.subpurpurescens (Warren, 1896) are redescribed based on their holotypes and additional material, and the latter two are newly recorded from China and their genitalia are described for the first time. The images of the habitus and genitalia of these eight species are provided, with a key to their identification.
ABSTRACT
Background: Excessive doses of electromagnetic radiation pose a negative impact on the central nervous system and lead to mental disorders. Molecular hydrogen can scavenge intracellular hydroxyl radicals, acting as an antioxidant, anti-apoptotic and anti-inflammatory agent. We seek to assess the capability of molecular hydrogen to ameliorate brain damage induced by electromagnetic radiation. Methods: NEMP (nuclear electromagnetic pulse), a subset of electromagnetic pulse with high voltage value that could cause severe brain injury, was applied to this study. Male wild-type rats were divided into four groups: the control group, the H2 (Molecular hydrogen) group, the NEMP group and the NEMP+H2 group. Rats in the H2 group and the NEMP+H2 group were fed with saturated hydrogen-rich water from 3 days before NEMP exposure (electromagnetic field intensity 400 kV/m, rising edge 20 ns and pulse width 200 ns) to the day of sacrifice. One day after exposure, animal behavior experiments were performed, and samples for transcriptomics and metabolomics analysis were collected. Seven days after exposure, histopathological experiments were conducted. Results: The data from the elevated plus maze and the open field test showed that NEMP exposure elicited anxiety-like behavior in rats, which could be alleviated by H2 treatment. Histopathological results manifested that NEMP exposure-induced injuries of the neurons in the hippocampus and amygdala could be attenuated by H2 treatment. Transcriptomic results revealed that NEMP exposure had a profound effect on microtubule structure in the brain. And the combined analysis of transcriptomics and metabolomics showed that H2 has a significant impact on the neuroactive ligand-receptor interaction, synaptic vesicle cycle and synapse etc. Moreover, it was indicated that the glutathione metabolic pathway played a vital role in the NEMP exposure-induced damage and the protective activity of H2. Conclusions: H2 is identified as a potent agent against NEMP exposure-induced brain damage and has the potential to be a promising electromagnetic radiation protectant.
Subject(s)
Brain Injuries , Transcriptome , Rats , Male , Animals , Oxidative Stress , Electromagnetic Phenomena , Hydrogen/chemistry , Hydrogen/pharmacology , BrainABSTRACT
An efficient approach to access chiral N-α indole substituted pyrrolidine and piperidine skeletons has been developed through a AgSbF6-catalyzed N-α aza-Friedel-Crafts alkylation of N,O-acetals 6a, 6b, 9, and 11a-11d with indoles. As a result, a series of 2,3-trans N-α indole substituted pyrrolidines 8a-8x and piperidines 10a-10j were prepared in moderate to excellent yields and with excellent diastereoselectivities (dr up to 99 : 1). Moreover, several 2,5-cis-N-α indole substituted pyrrolidine derivatives 12a-12k were synthesized according to this strategy with moderate to good yields and diastereoselectivities (dr up to 99 : 1).
ABSTRACT
Infertility has got to be a broadly concerned social issue these days, in which the malefactor cannot be overlooked. Numerous studies have shown that electromagnetic pulse (EMP) radiation may have seriously damaging effects on reproductive health, through nonthermal effects and oxidative stress. Molecular hydrogen, a selective hydroxyl radical scavenger, explains the protective effects against many diseases closely associated with oxidative damage, such as ionizing radiation (IR). We sought to characterize the beneficial effects of molecular hydrogen on the male reproductive system in a rodent EMP exposure model. The 8-week-old male Sprague-Dawley rats were exposed to EMP (peak intensity 1000 kV/m, pulse edge 20 ns, pulse width 200 ns, 1 Hz, and 200 pulses), with or without hydrogen-rich water. The pathological structure of the testis, the rate of apoptosis of the testis, the serum testosterone level, the sperm parameters, and the activity of the antioxidant enzymes of the testis were measured. Then, transcriptomic and untargeted metabolomic analyses were applied to uncover the underlying mechanism. Exposure to EMP increased testicular apoptosis rate and apoptosis protein level, decreased sperm viability and motility, decreased serum testosterone levels, and diminished testicular antioxidant capacity. Molecular hydrogen-alleviated damage decreased the testicular apoptosis rate and apoptosis protein level, increased sperm motility, increased serum testosterone levels, and improved antioxidative capacity. Omics results showed that molecular hydrogen has a strong influence on metabolic pathways, and EMP affects mainly oxidative phosphorylation, TNF signaling pathways, and cytokine-receptor interactions. The mechanism of molecular hydrogen's effect may be related to the reversal of some metabolite levels. These observations warrant molecular hydrogen as an innovative approach for potential protection against EMP.
Subject(s)
Antioxidants , Rodentia , Animals , Antioxidants/pharmacology , Cytokines/metabolism , Electromagnetic Phenomena , Hydrogen/metabolism , Hydrogen/pharmacology , Hydroxyl Radical/metabolism , Male , Oxidative Stress , Rats , Rats, Sprague-Dawley , Rodentia/metabolism , Semen/metabolism , Sperm Motility , Testis/metabolism , Testosterone , Water/pharmacologyABSTRACT
The present study established a determination method of Psoraleae Fructus by quantitative analysis of multi-components by the single marker(QAMS) and further improved the thin-layer chromatography(TLC) method. The QAMS method was established by UPLC with psoralen as the internal marker, and the content of psoralenoside, isopsoralenoside, psoralen, and isopsoralen was simultaneously determined. As revealed by the comparison with results of the external standard method, the QAMS method was accurate and feasible. According to the current quality standards of Psoraleae Fructus, the TLC method was further optimized and improved, and bakuchiol was added for identification based on the original TLC method with psoralen and isopsoralen as indicators. This study provides a reference for improving the quality control method of Psoraleae Fructus.
Subject(s)
Drugs, Chinese Herbal , Furocoumarins , Psoralea , Chromatography, High Pressure Liquid/methods , Drugs, Chinese Herbal/analysis , Ficusin , Fruit/chemistry , Furocoumarins/analysisABSTRACT
An efficient approach to access α-arylacetylene-substituted pyrrolidine and piperidine derivatives has been developed through a samarium diiodide-mediated addition-elimination process of pyrrolidine and piperidine N-α-radicals with arylacetylene sulfones.
Subject(s)
Samarium , Sulfones , Iodides , Piperidines , PyrrolidinesABSTRACT
An efficient approach to functionalized (E)-3-cinnamyl-3-methyl-2,3-dihydrobenzofurans and (E)-(3-methyl-2,3-dihydrobenzofuran-3-yl)but-2-enones has been developed through a Pd-catalyzed one-pot cascade process involving two sequential Heck reactions, that is, an intramolecular Heck reaction of olefin-tethered aryl iodides and an intermolecular Heck reaction with substituted styrenes and α,ß-unsaturated ketones. As a result, a series of desired products were obtained in moderate to good yields and with exclusive E-form selectivities.
Subject(s)
Alkenes , Palladium , Catalysis , Iodides , StyrenesABSTRACT
A catalyzed process for the synthesis of the 4,6-substituted 3,4-dihydro-1,3-oxazin-2-one skeleton has been developed through cycloaddition of in situ generated acyliminium intermediates with alkynes. A range of chain N,O-acetals and terminal alkynes were amenable for this mild transformation. As a result, a series of desired cycloaddition products were obtained in moderate to good yields.
Subject(s)
Alkynes , Skeleton , Catalysis , Cycloaddition Reaction , Ions , Molecular StructureABSTRACT
Regioselective C-H alkenylation of N,N-dialkylanilines with ynamides was developed using AgNTf2 as a catalyst. This approach represents a facile hydroarylation of ynamides, allowing for the introduction of an alkenyl group exclusively at the para position of aniline derivatives. As a result, a series of 4-alkenyl N,N-dialkylanilines were synthesized with excellent regioselectivities.
Subject(s)
CatalysisABSTRACT
@#Abstract: Objective ( ) To compare the measured results of arsenic in urine by atomic fluorescence spectrometry AFS and - ( - ), Methods inductively coupled plasma mass spectroscopy ICP MS and analyze the reasons of the difference. The samples WS/T 474-2015 Determination of Arsenic in Urine by Hydride Generation Atomic Fluorescence were pretreated according to Spectrometry, ( ∶ ∶ ∶∶ ,V/V/V) and digested with mixed acid nitric acid sulfuric acid perchloric acid=3 1 1 and then determined by - - AFS and ICP MS. The samples were diluted with 0.50% nitric acid and determined by ICP MS. The samples included urine , , ( arsenic quality control samples inorganic arsenic supplemented samples and organic arsenic arsenic choline and arsenic ) - betaine supplemented samples. Standard curve method was used to compare the results of AFS method and ICP MS method. Results ( ) ( ) The results of quality control samples by AFS method digestion and ICP-MS method without digestion were , - within the range of reference values but the values obtained by AFS method were lower than those obtained by ICP MS method. - - - , The recovery of AFS and ICP MS was 97.79% 100.82% and 99.55% 99.98% respectively. In the middle and high , - ( P ) concentration groups the measured values of inorganic arsenic by AFS were lower than that by ICP MS all <0.01 . The ( ) - recovery of arsenic betaine and arsenic choline by AFS method digestion was only 2.17% 2.63%. The values of arsenic betaine ( ) - ( and arsenic choline measured by AFS method digestion were lower than those measured by ICP MS method without ) - ( )( P )Conclusion digestion and ICP MS method digestion all <0.01 . The result of urine arsenic measured by AFS method - , was lower than that measured by ICP MS method which may be related to the mixed acid digestion of AFS method. Keywords: ; - ; ; ; ; ;
ABSTRACT
A unique prenylated bicarbazole alkaloid, clausanisumine (1), and two biogenetically related known monomer carbazole alkaloids, mukonal (2) and 3-methylcarbazole (3), were isolated from the fruits of Clausena anisum-olens. Clausanisumine (1) was an uncommon prenylated bicarbazole alkaloid, possessing an unprecedented carbon skeleton, which was composed of a simple carbazole alkaloid and a prenylated carbazole alkaloid. The chemical structure of 1 was established by a combination of comprehensive spectral methods. A plausible biosynthetic pathway of 1 was also proposed. Additionally, the potential anti-HIV activities of all isolates 1-3 in vitro were evaluated. Compound 1 exhibited remarkable anti-HIV-1 reverse transcriptase effects showing an EC50 value of 18.58 nM. The discovery of the prenylated bicarbazole alkaloid from C. anisum-olens with notable anti-HIV activity would be meaningful to discovering and developing new anti-HIV drugs.
Subject(s)
Alkaloids , Anti-HIV Agents , Clausena , Alkaloids/pharmacology , Anti-HIV Agents/pharmacology , Carbazoles/pharmacology , Fruit , Molecular StructureABSTRACT
The chemical constituents from the stems and leaves of Clausena excavata were isolated and purified by column chromatography with silica gel, ODS, Sephadex LH-20 and RP-HPLC. The chemical structures of the isolated compounds were identified on the basis of physicochemical properties, spectroscopic analysis, as well as the comparisons with the data reported in literature. Nineteen compounds were isolated from the 90% ethanol extract of the stems and leaves of C. excavata, which were identified as methyl orsellinate(1), syringaresinol(2), lenisin A(3), scopoletin(4), osthenol(5), N-benzoyltyrarnine methyl ether(6), N-p-coumaroyltyramine(7), aurantiamide acetate(8), 1H-indole-3-carboxaldehyde(9), furostifoline(10), clausenalansine E(11), 3-formylcarbazole(12), clausine L(13), clausine E(14), methyl carbazole-3-carboxylate(15), glycosinin(16), murrayafoline A(17), clausine H(18) and 2,7-dihydroxy-3-formyl-1-(3'-methyl-2'-butenyl)carbazole(19). Among these isolated compounds, compounds 1-11 were isolated from C. excavata for the first time, and compounds 1, 2 and 10 were isolated from the genus Clausena for the first time. In addition, this study evaluated the anti-rheumatoid arthritis activities of compounds 1-19 by measuring their anti-proliferative effects on synoviocytes in vitro according to MTS method. Compounds 10-19 displayed remarkable anti-rheumatoid arthritis activities, which exhibited the inhibitory effects on the proliferation of MH7 A synovial fibroblast cells with the IC_(50) values ranging from(27.63±0.18) to(235.67±2.16) µmol·L~(-1).
Subject(s)
Clausena , Synoviocytes , Cell Proliferation , Chromatography, Reverse-Phase , Plant LeavesABSTRACT
A novel approach to 2-substituted-2-(dimethoxyphosphoryl)-pyrrolidines 7a-7o and 9a-9r has been developed, which features a TMSOTf-mediated one-pot intramolecular cyclization and phosphonylation of substituted tert-butyl 4-oxobutylcarbamates. The major advantages of this method include simple operation under mild reaction conditions, the use of cheap Lewis acid, and good to excellent yields with high diastereoselectivities (dr up to 99:1).
Subject(s)
Lewis Acids , Pyrrolidines , Cyclization , Phosphites , StereoisomerismABSTRACT
The phytochemical investigation on the fruits of Clausena anisum-olens led to the isolation of 18 carbazole alkaloids (1-18), containing three new ones, clausenanisines A-C (1-3), and three new naturally occurring carbazole alkaloids, clausenanisines D-F (4-6), as well as 12 known analogues (7-18). The chemical structures of clausenanisines A-F (1-6) were elucidated by extensive spectroscopic methods. Notably, clausenanisine A (1) was a novel carbazole alkaloid with a unique five-membered cyclic ether, while clausenanisine E (5) is an unusual carbazole alkaloid owning an unprecedented naturally occurring carbon skeleton possessing 14 carbon atoms. The known carbazole alkaloids (7-18) were identified by the comparison of their spectral data with those data reported in the literature. All known carbazole alkaloids 7-18 were isolated from C. anisum-olens for the first time. Moreover, all isolated compounds 1-18 were assessed for their protein tyrosine phosphatase 1B (PTP1B) and α-glucosidase inhibitory activities in vitro. Compounds 1-18 exhibited remarkable PTP1B inhibitory activities with IC50 values in the range of 0.58 ± 0.05 to 38.48 ± 0.32 µM, meanwhile, compounds 1-18 displayed significant α-glucosidase inhibitory activities with IC50 values ranging from 3.28 ± 0.16 to 192.23 ± 0.78 µM. These research results imply that the separation and identification of these carbazole alkaloids showing notable PTP1B and α-glucosidase inhibitory activities from the fruits of C. anisum-olens can be very significant for discovering and developing new PTP1B inhibitors and α-glucosidase inhibitors for the treatment of diabetes mellitus.
Subject(s)
Alkaloids/pharmacology , Carbazoles/pharmacology , Clausena/chemistry , Enzyme Inhibitors/pharmacology , Protein Tyrosine Phosphatase, Non-Receptor Type 1/antagonists & inhibitors , alpha-Glucosidases/metabolism , Alkaloids/chemistry , Alkaloids/isolation & purification , Carbazoles/chemistry , Carbazoles/isolation & purification , Dose-Response Relationship, Drug , Enzyme Inhibitors/chemistry , Enzyme Inhibitors/isolation & purification , Fruit/chemistry , Humans , Molecular Docking Simulation , Molecular Structure , Protein Tyrosine Phosphatase, Non-Receptor Type 1/metabolism , Structure-Activity RelationshipABSTRACT
The investigation on the stems and leaves of Clausena lenis led to the isolation of a previously undescribed carbazole alkaloid, clausenalenine A (1), along with seven known analogues (2-8). The structure of 1 was elucidated based on comprehensive spectroscopic analyses and the known compounds were identified by comparisons with data reported in the literatures. All known compounds (2-8) were isolated from C. lenis for the first time. All isolated compounds were evaluated for their neuroprotective activities against 6-hydroxydopamine induced cell death in human neuroblastoma SH-SY5Y cells in vitro. Compounds 1-8 showed significant neuroprotective effects with EC50 values ranging from 0.68 to 18.76 µM.
Subject(s)
Alkaloids/pharmacology , Clausena/chemistry , Neuroprotective Agents/chemistry , Neuroprotective Agents/pharmacology , Alkaloids/chemistry , Carbazoles/chemistry , Cell Line, Tumor , Drug Evaluation, Preclinical , Humans , Molecular Structure , Plant Leaves/chemistry , Plant Stems/chemistry , Spectrometry, Mass, Electrospray IonizationABSTRACT
In the presence of the chiral Pd(0)/ligand complex, vinyl benzoxazinanones underwent the [4+2] cycloaddition with alkylidene pyrazolones smoothly and delivered spiropyrazolones in reasonable yields, diastereoselectivities, and eneantioselectivities (up to >99% yield, >99:1 dr and 99% ee). The absolute configuration of the obtained spiropyrazolones was unambiguously characterized with the use of X-ray single-crystal structure analysis. Moreover, the reaction mechanism was assumed to interpret the formation of the target compounds.
ABSTRACT
Toona sinensis, popularly known as Chinese toon or Chinese mahogany, is a perennial deciduous arbor belonging to the genus Toona in the Meliaceae family, which is widely distributed and cultivated in eastern and southeastern Asia. Its fresh young leaves and buds have been consumed as a very popular nutritious vegetable in China and confirmed to display a wide variety of biological activities. To investigate the chemical constituents and their potential health benefits from the fresh young leaves and buds of T. sinensis, a phytochemical study on its fresh young leaves and buds was therefore undertaken. In our current investigation, 16 limonoids (1-16), including four new limonoids, toonasinenoids A-D (1-4), and a new naturally occurring limonoid, toonasinenoid E (5), were isolated and characterized from the fresh young leaves and buds of T. sinensis. The chemical structures and absolute configurations of limonoids 1-5 were elucidated by comprehensive spectroscopic data analyses. All known limonoids (6-16) were identified via comparing their experimental spectral data containing mass spectrometry data, 1H and 13C nuclear magnetic resonance data, and optical rotation values to the data reported in the literature. All known limonoids (6-16) were isolated from T. sinensis for the first time. Furthermore, the neuroprotective effects of all isolated limonoids 1-16 against 6-hydroxydopamine-induced cell death in human neuroblastoma SH-SY5Y cells were assessed in vitro. Limonoids 1-16 exhibited notable neuroprotective activities, with EC50 values in the range from 0.27 ± 0.03 to 17.28 ± 0.16 µM. These results suggest that regular consumption of the fresh young leaves and buds of T. sinensis might prevent the occurrence and development of Parkinson's disease (PD). Moreover, the isolation and characterization of these limonoids that exhibit notable neuroprotective activities from the fresh young leaves and buds of T. sinensis could be very significant for researching and developing new neuroprotective drugs used for the prevention and treatment of PD.
Subject(s)
Drugs, Chinese Herbal/chemistry , Limonins/chemistry , Neuroprotective Agents/chemistry , Plant Extracts/chemistry , Plant Leaves/chemistry , Plant Shoots/chemistry , Toona/chemistry , Drugs, Chinese Herbal/isolation & purification , Humans , Limonins/isolation & purification , Molecular Structure , Neuroprotective Agents/isolation & purification , Plant Extracts/isolation & purificationABSTRACT
Three new carbazole alkaloids, zanthoaustrones A-C (1-3), as well as nine known compounds 4-12, were isolated and characterized from the roots of Zanthoxylum austrosinense Huang (Rutaceae). Their chemical structures were elucidated on the basis of extensive and comprehensive spectroscopic methods, while the known alkaloids were identified by the comparison of their observed spectroscopic data including NMR data, MS data and optical rotation values with the data described in the literature. Furthermore, the antiproliferative activities as well as the anti-inflammatory effects of all isolated alkaloids in vitro were evaluated. All obtained alkaloids 1-12 displayed notable antiproliferative activities against diverse human cancer cell lines exhibiting IC50 values in range of 0.85 ± 0.06 to 29.56 ± 0.17 µM, which is equivalent to the positive control (cisplatin) showing IC50 values ranging from 1.58 ± 0.09 to 28.69 ± 0.21 µM. Moreover, compounds 1-12 exhibited pronounced inhibitory activities on nitric oxide (NO) production with IC50 values displaying IC50 values in range of 0.89 ± 0.05 to 9.62 ± 0.15 µM, which is comparable to the positive control (hydrocortisone) holding an IC50 value of 4.06 ± 0.11 µM. These findings indicate that the separation and characterization of these alkaloids displaying significant antiproliferative activities together with anti-inflammatory effects from the roots of Z. austrosinense could be meaningful to the research and development of new anti-cancer drugs as well as anti-inflammatory agents.