Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Phragmalin-Type Limonoids from the Fruits of Chukrasia tabularis and Their Anti-Inflammatory Activity.

ABSTRACT: Phytochemical investigation on the fruits of C. tabularis led to the isolation of five new phragmalin-type limonoids (1-5) and four known ones (6-9). The structures of the new compounds 1-5, named chuktabamalins A-E, were elucidated via spectroscopic techniques (HRESIMS, 1D and 2D NMR) and were comparable with the literature data of known compounds. In addition, new compounds were evaluated for in vitro anti-inflammatory activity. Compounds 1, 2, 3 and 5 showed moderate anti-inflammatory activity with IC₅₀ values of 21.72 ± 2.79, 23.29 ± 1.00, 47.08 ± 3.47 and 66.67 ± 2.89 μM, respectively.

SUBMITTER: Dai S

PROVIDER: S-EPMC10343657 | biostudies-literature | 2023 Jun

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Phragmalin-Type Limonoids from the Fruits of Chukrasia tabularis and Their Anti-Inflammatory Activity.

Dai Shujun S Wu Yuzhen Y Xin Xiujuan X An Faliang F

Molecules (Basel, Switzerland) 20230630 13

Phytochemical investigation on the fruits of C. tabularis led to the isolation of five new phragmalin-type limonoids (1-5) and four known ones (6-9). The structures of the new compounds 1-5, named chuktabamalins A-E, were elucidated via spectroscopic techniques (HRESIMS, 1D and 2D NMR) and were comparable with the literature data of known compounds. In addition, new compounds were evaluated for in vitro anti-inflammatory activity. Compounds 1</ ...[more]

PMID: 37446797

Similar Datasets

New Phragmalin-Type Limonoids from Chukrasia tabularis and Their α-Glucosidase Inhibitory Activity.

Project description:Phytochemical investigation on the stems of C. tabularis led to the isolation of five new phragmalin-type limonoids and six known ones. The structures of the new compounds 1-5, named chukbularisins A-E, were elucidated by spectroscopic techniques (IR, HRESIMS, 1D and 2D NMR) and comparisons with published data. All the compounds were evaluated for in vitro α-glucosidase inhibitory activity. Compounds 2, 3, 4, 5, and 8 exhibited inhibitory activity against α-glucosidase with IC50 values of 0.06 ± 0.008, 0.04 ± 0.002, 0.52 ± 0.039, 1.09 ± 0.040, and 0.20 ± 0.057 mM, respectively (using acarbose as positive control, IC50 0.95 ± 0.092 mM).

| S-EPMC6274087 | biostudies-literature

Six New Phragmalin Limonoids from the Stems of Chukrasia tabularis A. Juss.

Project description:Six new phragmalin limonoids, named moluccensin Z1 (1), moluccensin Z2 (2), carapanolide Y (3), tabulalin N (4), chukvelutilide A1 (5), and velutinasin J (6), as well as two known compounds, chukvelutilide A (7) and velutinasin D (8) were isolated from the stems of Chukrasia tabularis A. Juss. The structures of the new compounds 1⁻6 were confirmed by spectroscopic methods, including IR and HRESIMS, as well as 1D and 2D NMR, and by comparisons with the data of known analogues. All compounds were tested for α-glucosidase and acetylcholinesterase inhibitory activities. However, none of the compounds was active against α-glucosidase and acetylcholinesterase in vitro.

| S-EPMC6278448 | biostudies-literature

Bioactivity-guided isolation of anti-inflammatory limonins from Chukrasia tabularis.

Project description:Chukrasia tabularis is an economically important tree and widely cultured in the southeast of China. Its barks, leaves, and fruits are consumed as a traditional medicine and perceived as a valuable source for bioactive limonin compounds. The extracts from root barks of C. tabularis showed significant anti-inflammatory effect. The aim of this research was to explore the material basis of C. tabularis anti-inflammatory activity, and to purify and identify anti-inflammatory active ingredients. By a bioassay-guided isolation of dichloromethane fraction obtained two novel phragmalin limonins, Chukrasitin D and E (1 and 2), together with 12 known limonins (3-14). The chemical structure of these compounds is determined on the basis of extensive spectral analysis and chemical reactivity. In addition, the activities of these isolated limonins on the production of nitric oxide (NO), tumor necrosis factor alpha (TNF-α), and nuclear factor kappa B (NF-κB) in RAW264.7 cells induced by lipopolysaccharide (LPS) were evaluated. Limonins 1 and 2 indicated significant anti-inflammatory activity with IC50 values of 6.24 and 6.13 μM. Compound 1 notably inhibited the production of NF-κB, TNF-α and interleukin 6 (IL-6) in macrophages. The present results suggest that the root barks of C. tabularis exhibited anti-inflammatory effect and the limonins may be responsible for this activity.

| S-EPMC9731525 | biostudies-literature

Chukrasia tabularis limonoid plays anti-inflammatory role by regulating NF-κB signaling pathway in lipopolysaccharide-induced macrophages.

Project description:BackgroundChukrasia tabularisis, a well-known tropical tree native to southeastern China, has anti-inflammatory and antioxidant activities, and contains large amounts of limonoids and triterpenoids.ObjectiveThe aim of this study was to investigate the potential anti-inflammatory activity of limonoids from C. tabularis on lipopolysaccharide (LPS)-mediated RAW264.7 cells.Methods and resultsUsing a bioassay-guided approach, the chemical fraction with high anti-inflammatory activity was found and its chemical constituents were investigated. Phytochemical studies on active extracts resulted in the separation of three novel phragmalin limonoids (1-3), together with two known limonoids (4-5) and 11 tirucallane triterpenes (6-16). The activity of these isolated compounds in the production of nitric oxide (NO) on LPS-reated macrophages was evaluated. Limonoid 2 indicated significant anti-inflammatory activities with IC50 value of 4.58 μM. Limonoid 2 notably inhibited the production of NO, interleukin- 6 and tumor necrosis factor-α on macrophage. Signal transduction and activation of STAT and NF-κB activators were effectively blocked by limonoid 2.ConclusionsThese results indicate that limonoid 2 has an anti-inflammatory effect by the inhibiting JAK2/STAT3, iNOS/eNOS, and NF-κB signaling pathways and regulating inflammatory mediators.

| S-EPMC10392864 | biostudies-literature

Anti-inflammatory Limonoids From Cortex Dictamni.

Project description:The root barks of perennial herb Dictamnus dasycarpus (Cortex Dictamni) were reported to be rich in anti-inflammation activity constituents, limonoids. Then, the investigation of anti-inflammation therapeutic limonoids from this plant was developed in the present study. Through the combination of various chromatographies isolation, six new limonoids, named dictamlimonol A (1), dictamlimonoside B (2), and dictamlimonols C-F (3-6), along with seven known ones (7-13), were obtained. Their structures were ascertained based on the extensive spectroscopic methods and ECD data analysis. Among them, compound 1 was the first 7,19-epoxy limonoid found in natural products. The anti-inflammatory effects of all limonoids were evaluated in lipopolysaccharide (LPS)-treated RAW 264.7 cell lines. Compounds 5, 7-11, and 13 were found to inhibit LPS-induced nitric oxide (NO) production. Moreover, dictamlimonol D (5), fraxinellone (11), and dasylactone A (13) were found to reduce the LPS-induced expressions of interleukin-6 (IL-6), tumor necrosis factor (TNF-α), inducible nitric oxide synthase (iNOS), nuclear factor kappa-light-chain-enhancer of activated B cells (NF-κB), and cyclooxygenase-2 (COX-2) at the protein levels in a dose-dependent manner. These findings support that the administration of Cortex Dictamni may be beneficial for inflammation.

| S-EPMC7058982 | biostudies-literature

Limonoids from the fruits of Khaya ivorensis.

Project description:Two new limonoids, namely 14,15-didehydroruageanin A (1) and 3-O-methyl- butyrylseneganolide A (2), were isolated from the fruits of Khaya ivorensis along with six known limonoids: seneganolide A (3), 1,3-dideacetylkhivorin (4), 7-deacetylkhivorin (5), 3-deacetylkhivorin (6), 1-deacetylkhivorin (7), and 3-deacetyl-7-oxokhivorin (8). All the compounds were evaluated for their cytotoxicity against five tumor cell lines.

| S-EPMC6271042 | biostudies-literature

Bioactive compounds, antioxidant capacity and anti-inflammatory activity of native fruits from Brazil.

Project description:The purpose of this study was to extract, identify, and quantify the phenolic compounds in grumixama (Eugenia brasilienses Lam.) and guabiju (Myrcianthes pungens), native fruits from southern region of Brazil, and to explore their antioxidant and anti-inflammatory properties. The phenolic compounds were extracted with acidified water and acidified methanol and evaluated for their bioactive constituents, antioxidant capacity, and anti-inflammatory properties. Spectrophotometric quantification shows tannins to be the most prevalent at 2.3 to 5.8 g/100g fresh fruit with acidified methanol containing higher concentrations of different phenolics than acidified water. HPLC analysis indicates that gallic acid, catechin, vanillic acid, and ellagic acid are the most prevalent phenolics in the two fruits extracts. Scavenging of DPPH and NO radicals showed inhibition by as much as 95% and 80%, respectively, at 2.5 gallic acid equivalent (GAE)/mL of the extract. At 50 μg GAE/mL, the release of pro-inflammatory molecules NO and IL-6 was significantly reduced with acidified methanol extract having higher inhibitory activity. Our results revealed that these native fruits, grown in the south of Brazil, are rich sources of phenolic compounds and have great antioxidant and anti-inflammatory activity.

| S-EPMC10171607 | biostudies-literature

In Vitro Anti-Inflammatory Study of Limonoids Isolated from Chisocheton Plants.

Project description:Chisocheton plants from the family Meliaceae have traditionally been used to treat several diseases; however, scientific evidence is limited. The most abundant chemical constituents of this plant are the limonoids, which are known for their various biological activities, including anti-inflammatory effects. However, the anti-inflammatory effects and underlying mechanisms of action of the constituents of Chisocheton plants have not been fully explored. In this report, we evaluated the anti-inflammatory activity of 17 limonoid compounds from Chisocheton plant primarily by measuring their inhibitory effects on the production of pro-inflammatory cytokines, including TNF-α, IL-6, IL-1β, and MCP-1, in LPS-stimulated THP-1 cells using an ELISA assay. Compounds 3, 5, 9, and 14-17 exhibited significant activity in inhibiting the evaluated pro-inflammatory markers, with IC50 values less than 20 µM and a high selectivity index (SI) range. Compounds 3, 5, 9, and 15 significantly suppressed the expression of phosphorylated p38 MAPK in THP-1 cells stimulated with LPS. These findings support the use of limonoids from Chisocheton plants as promising candidates for anti-inflammatory therapy.

| S-EPMC10814725 | biostudies-literature

Sudachinoid- and Ichangensin-Type Limonoids from Citrus junos Downregulate Pro-Inflammatory Cytokines.

Project description:Limonoids, a dominant group of phytochemicals in the Rutaceae family, are known to exhibit several pharmacological activities. To identify natural products having efficacy against inflammatory bowel disease (IBD), we isolated 13 limonoids including a new compound, methyl sudachinoid A, from the seeds of Citrus junos and investigated their anti-inflammatory effects by assessing the expression of pro-inflammatory cytokines in lipopolysaccharide-stimulated RAW 264.7 mouse macrophages and HT-29 human colon epithelial cells. Our findings revealed that limonoids significantly downregulated the pro-inflammatory cytokines, such as interleukin (IL)-1β, IL-6, IL-8, tumor necrosis factor-α, and nuclear transcription factor κB. In particular, sudachinoid-type compounds, methyl sudachinoid A and sudachinoid B, and ichangensin-type compound, 1-O-methyichangensin downregulated the expression of pro-inflammatory cytokines more potently than other limonoids, nomilin and limonin, which have been previously reported to exhibit anti-inflammatory activities in other cells; nomilin and limonin were therefore employed as positive controls in this study. Herein, we reveal that the anti-inflammatory activities of limonoids including a new compound methyl sudachinoid A from C. junos were mediated via the downregulation of pro-inflammatory cytokines and these limonoids can be employed as potential therapeutic phytochemicals for IBD.

| S-EPMC7555237 | biostudies-literature

Anti-inflammatory lignans from the fruits of Acanthopanax sessiliflorus.

Project description:A new lignan, named acanthosessilin A (1), as well as eight known lignan and lignan glycosides 2-9 were isolated from an ethanolic extract of Acanthopanax sessiliflorus fruits. The chemical structures were determined by spectroscopic methods, including HR-EIMS, 1D NMR (1H, 13C, DEPT), 2D NMR (gCOSY, gHSQC, gHMBC, NOESY), and IR spectroscopy. All isolated compounds were tested for the ability to inhibit LPS-induced nitric oxide production in RAW264.7 macrophages.

| S-EPMC6270163 | biostudies-literature