Diterpenoid Alkaloids from Delphinium ajacis and Their Anti-inflammatory Activity.

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 compounds (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 compounds (1-9) was conducted, focusing on nitric oxide (NO) production in LPS-induced BV-2 cells. The results indicated compounds 1-3, 7, and 8 have potential anti-inflammatory activity.

Phenolic and flavonoid compounds from the fruit shell of Camellia oleifera.

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.

Lycopodium Alkaloids from Huperzia serrata and Their Anti-acetylcholinesterase Activities.

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 in vitro, and compound 7 showed significant anti-acetylcholinesterase activity with an IC50 value of 16.18±1.64 µM.

Water-soluble matrine-type alkaloids with potential anti-neuroinflammatory activities from the seeds of Sophora alopecuroides.

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.

One new sesquiterpene pyridine alkaloid from the stems and leaves of Euonymus fortunei.

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].

Chemical constituents from the thorns of Gleditsia sinensis and their cytotoxic activities.

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].

Alopecuroides A-E, Matrine-Type Alkaloid Dimers from the Aerial Parts of Sophora alopecuroides.

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.

Matrine-Type Alkaloids from the Roots of Sophora flavescens and Their Antiviral Activities against the Hepatitis B Virus.

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.

New Acetophenone Derivatives from Acronychia oligophlebia and Their Anti-inflammatory and Antioxidant Activities.

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.

Diterpenoid Alkaloids from Delphinium ajacis and Their Anti-RSV Activities.

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.

Six New Pentacyclic Triterpenoids from the Fruit of Camptotheca acuminata.

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.

Six New Acylphloroglucinols from Dryopteris championii.

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.

Phorbol ester-type diterpenoids from the twigs and leaves of Croton tiglium.

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.

Dimeric Matrine-Type Alkaloids from the Roots of Sophora flavescens and Their Anti-Hepatitis B Virus Activities.

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.

Drychampones A-C: Three Meroterpenoids from Dryopteris championii.

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.

New labdane diterpenoids from Croton laui and their anti-inflammatory activities.

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.

[Chemical Constituents from Thalictrum fortune].

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) 、4-( 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( 1→6)-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( 1→6)-ß-D-glucopyranosyl( 1→4)-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.

Phenolic Compounds from the Flowers of Bombax malabaricum and Their Antioxidant and Antiviral Activities.

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.

[Chemical Constituents from Syzygium samarangense Branches and Leaves].

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.

Lidocaine potentiates the deleterious effects of triamcinolone acetonide on tenocytes.

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.