ABSTRACT
Three novel diterpenoid alkaloids, comprising two C19 -diterpenoid alkaloids (1 and 2) and one C20 -diterpenoid alkaloid (3), were isolated from Delphinium ajacis, alongside the six known compoundsâ (4-9). Their structures were elucidated by spectroscopic methods (MS, UV, IR, 1D and 2D NMR) and chemical properties. Simultaneously, the anti-inflammatory properties of all compoundsâ (1-9) was conducted, focusing on nitric oxide (NO) production in LPS-induced BV-2 cells. The results indicated compoundsâ 1-3, 7, and 8 have potential anti-inflammatory activity.
Subject(s)
Alkaloids , Delphinium , Diterpenes , Delphinium/chemistry , Magnetic Resonance Spectroscopy , Alkaloids/pharmacology , Alkaloids/chemistry , Diterpenes/pharmacology , Diterpenes/chemistry , Anti-Inflammatory Agents/pharmacology , Molecular StructureABSTRACT
A new phenolic compound oleiphenol (1), and a new dihydrochalcone oleifechalcone (2) along with seven known compounds (3-9) were isolated from the fruit shell of Camellia oleifera Abel. The planar structures of compounds 1 and 2 were determined on the basis of extensive spectroscopic analyses (IR, UV, NMR, and HR-ESI-MS) and comparison with literature data. The absolute configurations of the new structures were determined by ECD calculations and chemical methods. In addition, compounds 1-9 underwent a series of pharmacological activity tests, including cytotoxic, anti-inflammatory, anti-RSV and antioxidant activities.
Subject(s)
Camellia , Fruit , Flavonoids/pharmacology , Camellia/chemistry , Antioxidants/pharmacology , Antioxidants/chemistry , Magnetic Resonance SpectroscopyABSTRACT
One new fawcettimine-type alkaloid (1), one new miscellaneous-type alkaloid (2), four new lycodine-type alkaloids (3-6), and eight known ones (7-14) were isolated from the whole plants of Huperzia serrata. Their structures and absolute configurations were elucidated based on spectroscopic data, X-ray diffraction, ECD calculation and Mosher's method. Compound 1 was a rare C18 N2 -type Lycopodium alkaloid, possessing serratinine skeleton with an amide side chain in C-5. The absolute configuration of the 18-OH of compounds 4-6 were first determined by Mosher's method. Moreover, compounds 1-14 were assayed anti-acetylcholinesterase effect inâ vitro, and compound 7 showed significant anti-acetylcholinesterase activity with an IC50 value of 16.18±1.64â µM.
Subject(s)
Alkaloids , Huperzia , Lycopodium , Acetylcholinesterase , Alkaloids/pharmacology , Alkaloids/chemistry , Cholinesterase Inhibitors/pharmacology , Cholinesterase Inhibitors/chemistry , Huperzia/chemistry , Lycopodium/chemistry , Molecular StructureABSTRACT
A phytochemical investigation on the alkaloids from water-soluble part of Sophora alopecuroides led to obtain forty matrine-type alkaloids (1-40) including eighteen new ones (1-18), which covers almost all positions of the oxygen substitution in matrine-type structure. Notably, eight compounds (1-8) belong to rare bis-amide matrine-type alkaloid. The new structures were determined based on extensive spectroscopic data, electronic circular dichroism (ECD) calculations, and six instances, verified by X-ray crystallography. Most of isolates showed anti-neuroinflammatory activities based on the expression of tumor necrosis factor (TNF)-α and interleukin (IL)-6 in BV2 microglia cells. Especially, compound 39 can suppress those two mediator secretions in a dose-dependent manner with IC50 values of 21.6 ± 0.5 and 16.7 ± 0.8 µM, respectively. Further mechanistic study revealed that 39 suppressed the phosphorylation of IκBα and p65 subunit to regulate the NF-κB signaling pathway.
Subject(s)
Alkaloids/pharmacology , Anti-Inflammatory Agents/pharmacology , Quinolizines/pharmacology , Sophora/chemistry , Alkaloids/chemistry , Alkaloids/isolation & purification , Animals , Anti-Inflammatory Agents/chemistry , Anti-Inflammatory Agents/isolation & purification , Cell Line , Crystallography, X-Ray , Dose-Response Relationship, Drug , Interleukin-6/antagonists & inhibitors , Interleukin-6/metabolism , Mice , Models, Molecular , Molecular Structure , NF-kappa B/antagonists & inhibitors , NF-kappa B/metabolism , Quinolizines/chemistry , Quinolizines/isolation & purification , Seeds/chemistry , Signal Transduction/drug effects , Solubility , Structure-Activity Relationship , Tumor Necrosis Factor-alpha/antagonists & inhibitors , Tumor Necrosis Factor-alpha/metabolism , Water/chemistry , MatrinesABSTRACT
A new sesquiterpene pyridine alkaloid (1), along with four known compounds (2-5), were isolated from the stems and leaves of Euonymus fortunei. The new structure was determined by extensive spectroscopic analyses (IR, UV, NMR, HRESIMS and ECD). In addition, compound 3 showed a stronger anti-respiratory syncytial virus (RSV) activity with an IC50 value of 1.20 ± 0.10 µM than the positive control ribavirin with an IC50 value of 5.62 ± 0.49 µM.[Formula: see text].
Subject(s)
Alkaloids , Euonymus , Sesquiterpenes , Molecular Structure , Plant Leaves , PyridinesABSTRACT
A new aromatic glycoside (1) and a new natural product, neolignan (2), along with twenty-three known compounds (3-25), were isolated from the thorns of Gleditsia sinensis. According to the spectroscopic analyses (IR, UV, HRESIMS, NMR and ECD), the structures of isolates were elucidated. Herein, compounds 4, 6-8, 10-13, 15, 16, 18, 20, 23 were isolated from the plant of G. sinensis for the first time. Moreover, compounds 4, 6, 15 and 24 showed cytotoxic effects on human ovarian cancer (SKOV-3) cells with IC50 values of 24.83 ± 4.90, 48.86 ± 9.11, 80.13 ± 5.62, 15.38 ± 2.21 µM, respectively. [Formula: see text].
Subject(s)
Antineoplastic Agents , Gleditsia , Glycosides/pharmacology , Humans , Molecular Structure , Plant ExtractsABSTRACT
Five new matrine-type alkaloid dimers, alopecuroides A-E, were isolated from the aerial parts of Sophora alopecuroides. Alopecuroides A and B represent the first dimeric matrine-type alkaloids possessing a cyano group and an epoxy moiety. Alopecuroides C and D are dimeric matrine-type alkaloids connected via C-2-C-9' and C-10-C-3' bonds, respectively. The chemical structures of alopecuroides A-E were elucidated by spectroscopic methods combined with single-crystal X-ray diffraction analysis. The anti-inflammatory effects of alopecuroides A-E were evaluated, and alopecuroide B exhibited the most significant activity, better than that of matrine, the representative compound from S. alopecuroides.
Subject(s)
Alkaloids/chemistry , Plant Components, Aerial/chemistry , Quinolizines/chemistry , Sophora/chemistry , Alkaloids/isolation & purification , Alkaloids/pharmacology , Animals , Anti-Inflammatory Agents/pharmacology , Crystallography, X-Ray , Dimerization , Mice , Molecular Structure , RAW 264.7 Cells , Spectrum Analysis/methods , MatrinesABSTRACT
Eight new matrine-type alkaloids, flavesines G-J (1-4), alopecurine B (5), 7,11-dehydro-oxymatrine (6), 10-oxy-5,6-dehydromatrine (7), and 10-oxysophoridine (8), along with nine known analogues (9-17) were isolated from the roots of Sophora flavescens. Compounds 1-3 are the first natural matrine-type alkaloids with an open-loop ring D, while compound 4 represents an unprecedented dimerization pattern constructed from matrine and piperidine, and 5 is the first example of a matrine-type alkaloid with cleavage of the C-5-C-6 bond. The new structures were elucidated by means of spectroscopic data analysis (including NMR, MS, IR, and UV), and the absolute configurations were determined using single-crystal X-ray diffraction and ECD data. The isolated alkaloids were evaluated for their antiviral activity against hepatitis B virus, and compounds 1, 4, 5, 10, and 14 exhibited comparable antiviral potencies to matrine.
Subject(s)
Alkaloids/chemistry , Alkaloids/pharmacology , Antiviral Agents/pharmacology , Hepatitis B virus/drug effects , Plant Roots/chemistry , Quinolizines/chemistry , Quinolizines/pharmacology , Sophora/chemistry , Antiviral Agents/chemistry , Magnetic Resonance Spectroscopy , Mass Spectrometry , Molecular Structure , Spectrophotometry, Infrared , Spectrophotometry, Ultraviolet , X-Ray Diffraction , MatrinesABSTRACT
Seven new acetophenone derivatives (acroliones A - G, 1 - 7) and three known ones (8 - 10) were isolated from the leaves of Acronychia oligophlebia. Their structures were elucidated based on extensive spectroscopic analyses (IR, UV, HR-ESI-MS, 1D- and 2D-NMR), X-ray diffraction and comparison with literature data. The anti-inflammatory and antioxidant activities of all isolates were evaluated.
Subject(s)
Acetophenones/pharmacology , Anti-Inflammatory Agents, Non-Steroidal/pharmacology , Antioxidants/pharmacology , Biphenyl Compounds/antagonists & inhibitors , Nitric Oxide/antagonists & inhibitors , Picrates/antagonists & inhibitors , Rutaceae/chemistry , Acetophenones/chemistry , Acetophenones/isolation & purification , Animals , Anti-Inflammatory Agents, Non-Steroidal/chemistry , Anti-Inflammatory Agents, Non-Steroidal/isolation & purification , Antioxidants/chemistry , Antioxidants/isolation & purification , Crystallography, X-Ray , Mice , Models, Molecular , Molecular Structure , Nitric Oxide/biosynthesis , Plant Leaves/chemistry , RAW 264.7 CellsABSTRACT
Five new diterpenoid alkaloids, ajacisines A-E (1-5), were isolated from Delphinium ajacis, along with seven known alkaloids (6-12). On the basis of their spectral data (IR, UV, HR-ESI-MS, 1D and 2D NMR) and chemical properties, the structures of compounds 1-12 were identified. All isolated compounds were evaluated for their in vitro antiviral activities against respiratory syncytial virus, and compounds 3-5 and 8 exhibited moderate to weak effects with IC50 values of 75.2 ± 1.1, 35.1 ± 0.6, 10.1 ± 0.3, and 50.2 ± 0.5 µM, respectively.
Subject(s)
Alkaloids/pharmacology , Antiviral Agents/pharmacology , Delphinium/chemistry , Diterpenes/pharmacology , Molecular Structure , Respiratory Syncytial Virus, Human/drug effects , Alkaloids/chemistry , Alkaloids/isolation & purification , Antiviral Agents/chemistry , Antiviral Agents/isolation & purification , Cell Line, Tumor , Diterpenes/chemistry , Diterpenes/isolation & purification , Humans , Magnetic Resonance Spectroscopy , Plant Roots/chemistry , Plant Stems/chemistryABSTRACT
Six new pentacyclic triterpenoids were isolated from the fruit of Camptotheca acuminata. The chemical structures of the new compounds were elucidated by extensive spectroscopic analysis including HR-ESI-MS, IR, UV, 1D- and 2D-NMR. Moreover, the antibacterial activities of compounds 1, 2, 4, 5, and 6 were evaluated against Staphylococcus aureus, Escherichia coli, Bacillus subtilis and Dickeya zeae. All these tested compounds showed moderate antibacterial activity against Bacillus subtilis and Dickeya zeae.
Subject(s)
Anti-Bacterial Agents/isolation & purification , Camptotheca/chemistry , Pentacyclic Triterpenes/isolation & purification , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Bacteria/drug effects , Fruit/chemistry , Molecular Structure , Pentacyclic Triterpenes/chemistry , Pentacyclic Triterpenes/pharmacologyABSTRACT
Six new acylphloroglucinols (1 - 6) were isolated from Dryopteris championii. Their structures were established on the basis of extensive analysis of spectroscopic data and comparison with reported data. The antibacterial activities of the isolates were evaluated against Staphylococcus aureus, Escherichia coli, Bacillus subtilis, and Dickeya zeae.
Subject(s)
Anti-Bacterial Agents/isolation & purification , Dryopteris/chemistry , Phloroglucinol/isolation & purification , Anti-Bacterial Agents/chemistry , Bacteria/drug effects , Molecular Structure , Phloroglucinol/chemistry , Phloroglucinol/pharmacology , Plant Extracts/chemistry , Plant Extracts/pharmacology , Spectrum AnalysisABSTRACT
Phytochemical investigation of the ethanol extract from the twigs and leaves of Croton tiglium led to the isolation of two new phorbol esters (1-2) and seven known ones (3-9). Their structures were elucidated by the analyses of extensive spectroscopic data (IR, MS, and 1D and 2D NMR) and comparing with related compounds. Meanwhile, compounds 1-9 were determined for their cytotoxic activities on human lung cancer cell line A549. Among them, 1-2 were inactive against the cell line A549 (IC50 > 100 µM), but compounds 3 and 7 showed weak activities.
Subject(s)
Antineoplastic Agents, Phytogenic/isolation & purification , Croton/chemistry , Diterpenes/isolation & purification , Phorbol Esters/isolation & purification , Plant Components, Aerial/chemistry , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/pharmacology , Diterpenes/chemistry , Diterpenes/pharmacology , Drug Screening Assays, Antitumor , Humans , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Phorbol Esters/economics , Phorbol Esters/pharmacologyABSTRACT
Three novel sesquiterpenoid-based meroterpenoids, drychampones A-C (1-3, respectively), were isolated from Dryopteris championii. Compounds 1 and 3 possessed a novel carbon skeleton which was constructed by an 11/6/6 ring system coupled with a pyronone moiety, and 1-3 were three racemates. Their structures and absolute configurations were elucidated by NMR, MS, and computational methods. The hypothetical biosynthetic pathways of these meroterpenoids and their antibacterial activities were also discussed.
Subject(s)
Dryopteris/chemistry , Sesquiterpenes/isolation & purification , Anti-Bacterial Agents/pharmacology , Bacillus subtilis/drug effects , Carbon-13 Magnetic Resonance Spectroscopy , Circular Dichroism , Escherichia coli/drug effects , Microbial Sensitivity Tests , Molecular Structure , Proton Magnetic Resonance Spectroscopy , Sesquiterpenes/chemistry , Sesquiterpenes/pharmacology , Spectrometry, Mass, Electrospray Ionization , Staphylococcus aureus/drug effectsABSTRACT
Six unusual matrine-type alkaloid dimers, flavesines A-F (1-6, respectively), together with three proposed biosynthetic intermediates (7-9) were isolated from the roots of Sophora flavescens. Compounds 1-5 were the first natural matrine-type alkaloid dimers, and compound 6 represented an unprecedented dimerization pattern constructed by matrine and (-)-cytisine. Their structures were elucidated by NMR, MS, single-crystal X-ray diffraction, and a chemical method. The hypothetical biogenetic pathways of 1-6 were also proposed. Compounds 1-9 exhibited inhibitory activities against hepatitis B virus.
Subject(s)
Alkaloids/chemistry , Hepatitis B virus/drug effects , Quinolizines/chemistry , Sophora/chemistry , Alkaloids/pharmacology , Carbon/chemistry , Dimerization , Hep G2 Cells , Humans , Inhibitory Concentration 50 , Magnetic Resonance Spectroscopy , Molecular Structure , Plant Extracts/chemistry , Plant Extracts/pharmacology , Plant Roots/chemistry , Quinolizines/pharmacology , Real-Time Polymerase Chain Reaction , Spectrophotometry , X-Ray Diffraction , MatrinesABSTRACT
Nine new labdane diterpenoids (1-9) were isolated from the aerial parts of Croton laui, along with eight known analogues (10-17). Their structures were identified on the basis of the spectral data (IR, UV, HRESIMS, 1D and 2D NMR), and the structure of 8 was confirmed by single crystal X-ray diffraction analyses. In addition, compounds 1, 4, 7, 8, and 14 showed weak anti-inflammatory activities in LPS-stimulated RAW 264.7 cells.
Subject(s)
Anti-Inflammatory Agents/pharmacology , Croton/chemistry , Diterpenes/isolation & purification , Animals , Cell Line , Diterpenes/pharmacology , Mice , Spectrum Analysis/methodsABSTRACT
Objective: To investigate the chemical constituents of Thalictrum fortunei. Methods: Compounds were separated and purified by chromatographic methods and the structures were identified by their physicochemical properties and spectroscopic data. Results: Ten compounds were isolated and identified as bergenin( 1),1-( 4-hydroxy-3-methoxy)-phenyl-2-[4-( 1,2,3-trihydroxypropyl)-2-methoxy]-phenoxym-1,3-propandiol( 2) ã4-( 2-hydroxyethyl)-2-methoxyphenyl-O-ß-D-glucopyranoside( 3),meliasendanin D( 4),2-( 4-hydroxy-3-methoxyphenyl)-ethyl-O-ß-D-glucopyranoside( 5),kizutasaponin C( 6),2-( 3-hydroxy-4-methoxyphenyl)-ethyl-O-ß-Dglucopyranoside( 7),ß-sitosterol( 8),3-O-ß-D-glucopyranosyl( 1â6)-ß-D-glucopyranosyl( 22 S,24Z)-cycloart-24-en-3ß,22,30-tetraol-26-O-ß-D-glucopyranoside( 9) and 3-O-ß-D-quinovopyranosyl( 1â6)-ß-D-glucopyranosyl( 1â4)-ß-D-fucopyranosyl( 22 S,24Z)-cycloart-24-en-3ß,22,26-triaol-26-O-ß-D-glucopyranoside( 10). Conclusion: Compounds 1 ~ 6 are isolated form this plant for the first time.
Subject(s)
Thalictrum , Chromatography , Magnetic Resonance Spectroscopy , Molecular Structure , Plant ExtractsABSTRACT
Three new phenolic compounds 1-3 and twenty known ones 4-23 were isolated from the flowers of Bombax malabaricum. Their chemical structures were elucidated by spectroscopic analyses (IR, ESI-MS, HR-ESI-MS, 1D- and 2D-NMR) and chemical reactions. The antioxidant capacities of the isolated compounds were tested using FRAP and DPPH radical-scavenging assays, and compounds 4, 6, 8, 12, as well as the new compound 2, exhibited stronger antioxidant activities than ascorbic acid. Furthermore, all of compounds were tested for their antiviral activities against RSV by the CPE reduction assay and plaque reduction assay. Compounds 4, 10, 12 possess in vitro antiviral activities, and compound 10 exhibits potent anti-RSV effects, comparable to the positive control ribavirin.
Subject(s)
Antioxidants/pharmacology , Antiviral Agents/pharmacology , Bombax/chemistry , Flowers/chemistry , Phenols/pharmacology , Plant Extracts/pharmacology , Antioxidants/chemistry , Antiviral Agents/chemistry , Cell Line , Humans , Inhibitory Concentration 50 , Microbial Sensitivity Tests , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Phenols/chemistry , Plant Extracts/chemistry , Respiratory Syncytial Virus, Human/drug effectsABSTRACT
OBJECTIVE: To investigate the chemical constituents from the branches and leaves of Syzygium samarangense. METHODS: The dried branches and leaves of Syzygium samarangense were powdered and extracted with 95% ethanol, then partitioned with petroleum ether, chloroform and ethyl acetate. The chloroform fraction was subjected to silica gel, Sephdex L-20 and preparative HPLC. The structures were identified by physicochemical properties and spectral data. RESULTS: 14 compounds were respectively isolated and identified as ursolic aldehyde(1), betulin(2), betulinic aldehyde(3), betulinic acid(4), lupeol(5), ß-sitosterol(6), 5, 7-dihydroxy-6-methylflavanone(7), 2', 4'-dihydroxy-6'-methoxy-3'-methyldihydrochalcone (8), 2', 4'-dihydroxy-6'-methoxy-3'-methylchalcone (9), 5, 7-dihydroxy-6, 8-dimethylflavanone (10), 5, 7-dihydroxyflavanone (11), 2', 4'-dihydroxy-6'-methoxy-3', 5'-dimethyldihydrochalcone (12), 2'-hydroxy-4', 6'-dimethoxy-3'-methylchalcone(13) and p-hydroxyb6nzaldehyde(14). CONCLUSION: Compounds 1 - 4 and 14 are isolated from this plant for the first time.
Subject(s)
Phytochemicals/chemistry , Plant Extracts/chemistry , Plant Leaves/chemistry , Syzygium/chemistry , Pentacyclic Triterpenes , Phytochemicals/isolation & purification , Sitosterols , Triterpenes , Betulinic AcidABSTRACT
BACKGROUND: Local anesthetics are commonly used for the treatment of a variety of tendinopathies in combination with corticosteroids injection. The goal of this study was to evaluate the effects of lidocaine and triamcinolone acetonide (TA) on cultured rat tenocytes and to determine whether there is a synergistic effect. MATERIAL/METHODS: Rat patellar tendon-derived tenocytes were cultured with or without TA and lidocaine, and the culture without any additive served as the control. Cell morphology and cell viability were evaluated. Expressions of tenocyte-related genes were measured by qRT-PCR. RESULTS: TA, when exposed to tenocytes in vitro, significantly decreased cell viability. The cells cultured with TA had a flattened shape. Moreover, the expressions of tenocyte-related genes in tenocytes were markedly decreased in the TA-treated group. We found that 1% lidocaine synergistically increased the deleterious effects of TA. CONCLUSIONS: Our data provide evidence of the detrimental effects of these drugs on tendon tissues. Injection of TA in combination with 1% lidocaine should be used with caution.