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Anti-Inflammatory Activity of Four Triterpenoids Isolated from Poriae Cutis.

ABSTRACT: In this study, triterpenoid compounds from Poriae Cutis were separated by high-speed countercurrent chromatography (HSCCC) and identified using ultra-high performance liquid chromatography quadrupole time-of-flight tandem mass spectrometry (UHPLC-QTOF-MS/MS) and nuclear magnetic resonance (NMR). The in vitro anti-inflammatory activities of the purified triterpenoids on RAW 264.7 cells were also investigated. Triterpenoids, poricoic acid B, poricoic acid A, dehydrotrametenolic acid, and dehydroeburicoic acid were obtained; their levels of purity were 90%, 92%, 93%, and 96%, respectively. The results indicated that poricoic acid B had higher anti-inflammatory activity than those of poricoic acid A by inhibiting the generation of NO in lipopolysaccharide (LPS)-induced RAW 264.7 cells. However, dehydrotrametenolic acid and dehydroeburicoic acid had no anti-inflammatory activity. In addition, the production of cytokines (TNF-α, IL-1β, and IL-6) in cells treated with poricoic acid B decreased in a dose-dependent manner in the concentration range from 10 to 40 μg/mL. The results provide evidence for the use of Poriae Cutis as a natural anti-inflammatory agent in medicines and functional foods.

SUBMITTER: Zhang L

PROVIDER: S-EPMC8700795 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Anti-inflammatory triterpenoids from the stems of Microtropis fokienensis.

Project description:Three new ursane- and four new oleanane- type triterpenoids 1-7 were isolated, along with six known compounds 8-13, from the methanolic extract of Microtropis fokienensis. All structures were elucidated by mass and NMR spectroscopic methods. The isolates 4-10 and known compounds 14-17 that were previously isolated from this material were evaluated for anti-inflammatory activity based on effects against superoxide anion generation and elastase release by neutrophils in response to fMLP/CB. 11α,30-Dihydroxy-2,3-seco-olean-12-en-2,3-dioic anhydride (7) was the first triterpene anhydride from the genus of Microtropis to have the ring A expanded to a seven-membered ring; it showed significant anti-inflammatory activity against superoxide anion generation and elastase release. Unexpectedly, 30-hydroxy-2,3-seco-lup-20(29)-ene-2,3-dioic acid (17) showed the best effect against superoxide anion generation and elastase release with IC50 values of 0.06±0.01 and 1.03±0.35 µg/mL, respectively. Compound 17 had a dioic acid function, and compound 7 had an anhydride function modification in ring A; both showed promising activity in the target assays.

| S-EPMC6271155 | biostudies-literature

Triterpenoids from Euphorbia maculata and Their Anti-Inflammatory Effects.

Project description:Euphorbia maculata is a medicinal plant of the Euphorbiaceae family, which can produce anti-inflammatory and cancer chemopreventive agents of triterpenoids. The present study reports on the bioactive triterpenoids of this plant. Two new lanostane-type triterpenoids, named (3S,4S,7S,9R)-4-methyl-3,7-dihydroxy-7(8→9) abeo-lanost-24(28)-en-8-one (1) and 24-hydroperoxylanost-7,25-dien-3β-ol (2), together with 15 known triterpene derivatives, were isolated from Euphorbia maculata. The structures of the new compounds were determined on the basis of extensive spectroscopic data (UV, MS, ¹H and 13C-NMR, and 2D NMR) analysis. All tetracyclic triterpenoids (1⁻11) were evaluated for their anti-inflammatory effects in the test of TPA-induced inflammation (1 μg/ear) in mice. The triterpenes exhibited significant anti-inflammatory activities.

| S-EPMC6225269 | biostudies-literature

New Triterpenoids from the Fruiting Bodies of Laetiporus sulphureus and Their Anti-Inflammatory Activity.

Project description:Laetiporus sulphureus is a popular medicinal mushroom with diverse pharmacological activities in many Asian countries. Four new triterpenoids, named sulphurenoids A-D (1-4), along with 12 known analogues, were isolated from the fruits of L. sulphureus. Nuclear magnetic resonance, infrared spectroscopy, and high-resolution electrospray ionization mass spectrometry (HR-ESI-MS) techniques were used for the investigation of the chemical structure of isolated compounds. In addition, the anti-inflammatory activity of three new compounds (2-4) was tested for NO production in lipopolysaccharide-induced RAW 264.7 cells. The IC50 values of isolated triterpenoids ranged from 14.3 to 42.3 μM, which were more effective than the positive control (IC50 for minocycline was 73.0 μM). The experimentally obtained anti-inflammatory activity data of L. sulphureus are in agreement with its traditional use.

| S-EPMC9366770 | biostudies-literature

Triterpenoids and steroids isolated from Anatolian Capparis ovata and their activity on the expression of inflammatory cytokines.

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| S-EPMC7534286 | biostudies-literature

Anti-Inflammatory Activity of Triterpenes Isolated from Protium paniculatum Oil-Resins.

Project description:Protium is the main genus of the Burseraceae family and one of the most common genera in South America, with an important species called "breu." Gum and oil-resins of this species are used as tonic and stimulant and for the treatment of ulcers and inflammation. The present study aims to isolate and investigate the anti-inflammatory activity of triterpene compounds isolated from oil-resin of Protium paniculatum. The pentacyclic triterpenes ?,?-amyrin, acetylated ?,?-amyrin, ?,?-amyrone, and brein/maniladiol did not alter the viability of murine J774 macrophages (IC50 > 20?µg/mL), with the exception of mixture of brein/maniladiol which showed moderate cytotoxic activity. Also it was observed that compounds at 10?µg/mL inhibited more than 80% of production of NO(•), although only ?,?-amyrin was able to inhibit the production of TNF-? (52.03 ± 2.4%). The compounds inhibited the production of IL-6 and induced the production of IL-10 in murine J774 macrophages stimulated by LPS. ?,?-Amyrone inhibited the expression of COX-2 and also inhibited the formation of paw or ear edema in rats and mice, having a quick and immediate effect. This study may provide the basis for future investigations on the therapeutic role of ?,?-amyrone in treating inflammation.

| S-EPMC4806667 | biostudies-literature

Anti-Inflammatory Triterpenoids from the Caulophyllum robustum Maximin LPS-Stimulated RAW264.7 Cells.

Project description:Caulophyllum robustum Maxim is widely distributed in China and used as a traditional herbal medicine to induce childbirth, ease the pain of labor, rectify delayed or irregular menstruation, alleviate heavy bleeding and pain during menstruation, and treat external injuries and irregular menses. According to our detailed chemical investigation, three new triterpene derivatives (1⁻3), together with seven known compounds, were isolated from the root and rhizome of C. robustum Maxim. Their structures were elucidated by 1D- and 2D-NMR spectroscopic analysis and physio-chemical methods. They were identified as (1) 23-hydroxy-3,19-dioxo-olean-12-en-28-oic-acid; (2) 23-hydroxy-3,11-dioxo-olean-12-en-28-oic acid; and (3) 16α,23-dihydroxy-3-oxo-olean-12-en-28-oic acid. Compounds (1⁻10) inhibited the LPS-activated NO production in RAW264.7 cells. Furthermore, the anti-inflammatory characteristics of these compounds were confirmed on the basis of decreases in iNOS and NF-κB protein expression in RAW264.7 cells.

| S-EPMC6099581 | biostudies-literature

Four New Triterpenoids from Callicarpa kwangtungensis.

Project description:Four new triterpenoids which were identifed as 2α,3β,6β,19α-tetrahydroxy- oleanolic acid 28-O-β-D-glucopyranoside (1), 2-O-β-D-glucopyranosyloxy-3α,19α-di-hydroxyoleanolic acid (2), 2-O-β-D-glucopyranosyloxy-3α,19α-dihydroxyursolic acid (3), 2α,3α,6β,19α-tetrahydroxyursolic acid 28-O-β-D-glucopyranoside (4), were isolated from the aerial parts of Callicarpa kwangtungensis together with three known triterpenoids identified as 2α,3β,21β-trihydroxyursolic acid 28-O-β-D-glucopyranoside (5), 2α,3α,19α,23-tetrahydroxyoleanolic acid 28-O-β-D-glucopyranoside (6), 2α,3α,19α,23-tetrahydroxyursolic acid 28-O-β-D-glucopyranoside (7). Their structures were elucidated by the combination of mass spectrometry (MS), one and two-dimensional NMR experiments.

| S-EPMC6272150 | biostudies-literature

Anti-Inflammatory Activity of Piquerol Isolated from Piqueria trinervia Cav.

Project description:BackgroundInflammation is a complex process as a response to several stimuli, such as infection, a chemical irritant, and the attack of a foreign body. Piquerol was isolated from Piqueria trinervia, and its anti-inflammatory activity was evaluated using in vivo and in vitro models.MethodsPiquerol is a monoterpene that was identified using NMR, FT-IR spectroscopy, and mass spectrometry analysis. The anti-inflammatory activity was tested in vivo in ear edema induced with TPA in mice. Piquerol was also tested on J774A.1 macrophages stimulated with lipopolysaccharide (LPS), and the levels of NO, NF-κB, TNF-α, IL-1β, IL-6, and IL-10 were determined using ELISA.ResultsThe results show that piquerol diminished ear edema (66.19%). At 150.51 µM, it also inhibited the levels of NO (31.7%), TNF-α (49.8%), IL-1β (69.9%), IL-6 (47.5%), and NF-κB (26.7%), and increased the production of IL-10 (62.3%). Piquerol has a membrane stabilization property in erythrocyte, and at 100 µg/mL, the membrane protection was of 86.17%.ConclusionsPiquerol has anti-inflammatory activity, and its possible mechanism of action is through the inhibition of pro-inflammatory mediators. This compound could be a candidate in the development of new drugs to treat inflammatory problems.

| S-EPMC9324079 | biostudies-literature

Anti-inflammatory activity of nicotine isolated from Brassica oleracea in rheumatoid arthritis.

Project description:ObjectivesRheumatoid arthritis (RA) is an autoimmune disease, associated with chronic inflammation of synoviocytes. Tumor necrosis factor α (TNF-α) plays a crucial role in the pathogenesis of RA through pro-inflammatory cytokines. Nicotine, an alkaloid used as herbal medicine, often worked as an anti-inflammatory agent. In the present study, we tried to uncover the anti-inflammatory impact of nicotine against RA.Materials and methodsNicotine was isolated from Brassica oleracea, purified by high profile/phase liquid chromatography (HPLC). In-silico docking was carried out using bioinformatics tools SwissADME (absorption, distribution, metabolism and excretion), PASS, and Drug-induced Gene Expression Profile (DIGEP)-Pred to determine drug likeliness of nicotine. The in-vitro study was performed in TNFα-induced SW982 synoviocytes by qPCR. mRNA expression of pro-inflammatory cytokines (TNF, IL6, IL1β) and proteins (TRAF2, P50, P65) were analyzed followed by validation of P65 (RELA), pP65, IkBα by Western blot analysis.ResultsNicotine compound was extracted from Brassica oleracea and purified by HPLC method (Rt values at 2.67 min). The physicochemical, pharmacokinetic properties and drug-likeliness of nicotine were studied by in-silico analysis. In-vitro studies revealed that nicotine lowers the expression of inflammatory cytokines (TNF, IL6, IL1β) and proteins (TNF receptor-associated factor 2 (TRAF2), P50, P65) at 1 µg/ml in TNFα-induced SW982 cells.ConclusionNicotine from natural sources (Brassica oleracea) has been found to be an effective anti- inflammatory compound at a low dosage; thus, identifying the role of nicotine present in the natural sources as a therapeutic option for RA, may be recommended as remedial drug instead of synthetic drug.

| S-EPMC9069442 | biostudies-literature

Antibacterial and Synergistic Activity of Pentacyclic Triterpenoids Isolated from Alstonia scholaris.

Project description:(1) BACKGROUND: Alstonia scholaris (Apocynaceae) is an important medicinal plant that has been historically used in "Dai" ethnopharmacy to treat infectious diseases in China. Although various pharmacological activities have been reported, the antimicrobial constitutes of A. scholaris have not yet been identified. The objective of this study is to evaluate the antibacterial constitutes from the leaf extract of A. scholaris and to assess the synergistic effects of isolated compounds with antibiotics against bacterial pathogens.; (2) METHODS: The chemical constitutes isolated from the leaf extract of A. scholaris were structurally identified by NMR. The antibacterial and synergistic effect of compounds was assessed by calculating the minimal inhibitory concentration (MIC), checkerboard dilution test, and time-kill assay.; (3) RESULTS: Six pentacyclic triterpenoids were structurally identified as (1) lupeol, (2) betulin, (3) 3-hydroxy-11-ursen-28,13-olide, (4) betulinic acid, (5) oleanolic acid and (6) ursolic acid. Both oleanolic and ursolic acid showed antibacterial activity but were limited to Gram-positive bacteria. Ursolic acid showed a synergistic effect with ampicillin and tetracycline against both Bacillus cereus and S. aureus.; (4) CONCLUSION: These findings reflect that pentacyclic triterpenoids are the antibacterial chemicals in A. scholaris. The ability of ursolic acid to enhance the activity of antibiotics can constitute a valuable group of therapeutic agents in the future.

| S-EPMC6273878 | biostudies-other

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