Two new metabolites from Portulaca oleracea and their anti-inflammatory activities

Two new metabolites, identified as 6-phenylbenzofuran-4-ol, named olerabenzofuran (1), and 2-(furan-2-yl)− 6-hydroxy-1 H-inden-1-one, named oleraindenone (2), together with eight furan compounds obtained for the first time, (+)-pinoresinol (3), (-)-syringaresinol (4), (+)-diasyringaresinol (5), (+)-episyringaresinol (6), (2 S)− 1-[2-(furan-2-yl)− 2-oxoethyl]− 5-oxopyrrolidine-2-carboxylic acid (7), methyl (2 S)− 1[2-(furan-2-yl)− 2-oxoethyl]− 5-oxopyrrolidine-2-carboxylate (8), drynaran (9), and 2-furoic acid (10), were isolated from Portulaca oleracea L., and spectroscopic methods, including 1D and ²D NMR and UHPLC-ESI-QTOF/MS spectrometry techniques, were employed to determine their structures. It was suggested that both olerabenzofuran (1) and oleraindenone (2) could significantly inhibit inflammatory factor interleukin-1β (IL-1β) in RAW 264.7 cells induced by LPS.     

Compounds from the fruits of Nicandra physaloides and their potential anti-inflammatory activities

Twenty-one compounds were isolated and identified from the ethanol extract of the fruits of Nicandra physaloides, including four new (1–4) and 17 known compounds (5–21). All the compounds were isolated from the genus Physalis for the first time. In this study, NMR spectroscopy was used to study the compound structures by comparing their data with those reported in the literature. Moreover, the potential anti-inflammatory activity of RAW264.7 cells induced by lipopolysaccharide (LPS) was evaluated. Among the monoterpenoids, compounds (5–7, 9) exhibited weak anti-inflammatory activities, with IC₅₀ values ranging from 29.10 to 68.30 μM.     

Jatrophane polyesters from the leaves of Euphorbia peplus with anti-inflammatory activity

Three new jatrophane polyesters, Euphopepluanones M-O (1–3), along with eight known ones (4-11), were isolated from the leaves of Euphorbia peplus Linn. Their chemical structures were established based on extensive spectroscopic analysis. The absolute configurations of compound 1 were assigned by X-ray crystallographic analysis. In addition, their anti-inflammatory effects on lipopolysaccharide-induced RAW264.7 macrophages were evaluated in vitro. Among them, 2 and 7 exhibited significant anti-inflammatory activity.     

Novel phenolic and diterpenoid compounds isolated from the fruit spikes of Prunella vulgaris L. and their anti-inflammatory activities

Two novel phenolic compounds, prunellanate A (1) and prunellanate B (2), together with a diterpenoid compound, prunelladiterpenol A (3), were successfully isolated from the fruit spikes of Prunella vulgaris L. (Figure 1). Their structures were determined after extensive spectroscopic analyses including IR NMR, HR-ESI-MS empirical electronic circular dichroism (ECD), and X-ray diffraction. The biological activities of these new compounds on NO production in LPS (Lipopolysaccharide)-simulated RAW264.7 cells were evaluated. Compounds 1 and 3 showed significant anti-inflammatory activities revealing IC₅₀ values of 6.77 and 8.61 μM, respectively (aminoguanidine as positive control, IC₅₀ 20.33 ± 1.08 μM).     

New labdane diterpenoids from Leonurus japonicus and their anti-inflammatory activity

Two new, 16-oxo-leoheteronone A (1) and 15-methoxyleoheteronin B (2), and four known, 8,9-secohispanolone (3), galeopsin (4), hispanone (5), and leoheteronin B (6), labdane diterpenoids were isolated from the aerial parts of Leonurus japonicus. Compound 3 was isolated for the first time as a naturally occurring compound. Structures of the two compounds were determined on the basis of extensive spectroscopic techniques, including 1D, 2D NMR, and HREIMS. In addition, compounds 1–3, 5 and 6 were examined for inhibition of superoxide anion generation and elastase release, and the results suggested that compound 5 possesses anti-inflammatory activity.     

Two New Antioxidant Phenylpropanoids from Lindelofia stylosa

Two new phenylpropanoids were isolated from Lindelofia stylosa (Kar . and Kir .) and characterized as 4‐hydroxy‐N‐{4‐[(E)‐3‐(4‐hydroxy‐3‐methoxyphenyl)prop‐2‐enamido]butyl}benzamide ( 1 ) and 2‐[3‐hydroxy‐4‐(4‐hydroxyphenoxy)phenyl]‐1‐(methoxycarbonyl)ethyl (E)‐3‐(3,4‐dihydroxyphenyl)prop‐2‐enoate ( 2 ). Four known compounds, i.e. two phenylpropanoids, p‐coumaric acid (=(E)‐3‐(4‐hydroxyphenyl)prop‐2‐enoic acid; 3 ) and ferulic acid (=(E)‐3‐(4‐hydroxy‐3‐methoxyphenyl)prop‐2‐enoic acid; 4 ), and two naphthalene glycosides, 8‐O‐β‐D ‐glucopyranosyltorachrysone ( 5 ) and 8‐O‐β‐D ‐glucopyranosyl‐6‐demethoxytorachrysone ( 6 ), were also isolated for the first time from the plant. Compounds 1 – 6 were subjected to various antioxidant assays, including DPPH radical‐ and superoxide anion‐scavenging, and Fe²⁺‐chelation assays. Compound 2 was found to be most active in all assays with potency nearly similar to that of propyl gallate. Besides 2 , compounds 1 and 5 were also found to be active in DPPH radical‐scavenging standard assay.     

Phenylpropanoids from Thapsia transtagana

Five phenylpropanoids have been isolated from the roots of Thapsia transtagana. Their structures have been elucidated by spectroscopic means.     

New phenylpropanoids with cytotoxic activities from Drypetes hainanensis

Phytochemical investigation on Drypetes hainanensis has resulted in the isolation of three new phenylpropanoids, named drypetesins A–C (1–3). Their structures were elucidated by applying various spectroscopic techniques (NMR, UV, IR, MS, and CD). The antiproliferative activities of these compounds were evaluated in vitro against three cultured cancer cell lines. Those new isolates exhibited potent cytotoxic activities against human hepatoma (HepG2), human breast adenocarcinoma (MCF-7), and human lung carcinoma (A-549) cancer cell lines with IC₅₀ value range 5.6–14.8 μM.     

Two new flavanone glycosides from Scutellaria galericulata with anti-inflammatory activities

Two new flavanone glycosides, named scugalerosides A and B (1-2), were isolated from the whole plant of Scutellaria galericulata. Their chemical structures including absolute configurations were established on the basis of detailed physical data analyses. In vitro, two new compounds showed anti-inflammatory activities, with the inhibition rates of release of β-glucuronidase from polymorphonuclear leukocytes of rats being 43.7% and 45.1% at concentrations of 10 μM.     

New polyacetylene glucosides from the florets of Carthamus tinctorius and their weak anti-inflammatory activities

Eight new linear polyacetylene glucosides (1–8), containing two C₁₀-, one C₁₃- and five C₁₄-acetylenes, together with three known polyacetylenes (9–11) were isolated from the florets of Carthamus tinctorius L. Their structures were elucidated by means of spectroscopic methods and chemical evidence. The absolute configurations of compounds 3–9 were confirmed by Snatzke and Gerards’s method, observing the induced circular dichroism after addition of dirhodium tetrakis (trifluoroacetate) [Rh₂(OCOCF₃)₄] in CHCl₃. All the isolated compounds (1–11) were also tested for inhibitory activities against LPS-induced NO production in murine macrophages and just showed weak activities at concentrations of 1 × 10⁻⁵ M.     

Steroidal saponins from Smilax china and their anti-inflammatory activities

Steroidal saponins, 1, 2, 3 and 4, were isolated from the BuOH extract of Smilax china L., along with 13 known compounds, 5-17. Their structures were elucidated on the basis of MS, 1D and 2D NMR spectroscopic analyses and chemical evidence. In the bioassay tests, all compounds showed inhibitory effects on cyclooxygenase-2 enzyme (COX-2) activities at final concentration of 10(-5) M, and only compound 5 showed an inhibitory effect on production of TNFalpha (tumor necrosis factor alpha) in murine peritoneal macrophages at the same concentration.     

Phenylpropanoids from Paspalum atratum (Poaceae)

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New compounds with anti-inflammatory potential from Disporum cantoniense

Phytochemical investigation of Disporum cantoniense has resulted in the isolation of two new compounds, namely (3S,4S,5S)-5-C-(4-hydroxy-3-methoxybenzyl)-γ-lactone-2-deoxy-pentonic acid(1) and (3R,4S,5R)-5-C-(4-hydroxy-3-methoxybenzyl) -γ-lactone-2-deoxy-pentonic acid(2). Their structures were elucidated by various spectroscopic techniques. The absolute configurations of compounds were determined by ECD calculations analysis. Compound 1 showed significant inhibition of nitric oxide (NO) release in LPS-induced RAW264.7 macrophages with the IC50 value of 6.43 ± 0.68 μM, comparable to that of positive control amino guanidine (9.14 ± 0.62 μM). Herein we report the isolation, structure elucidation, as well as the evaluation of the anti-inflammatory activities of these two compounds.     

Further sesquiterpenoids from the rhizomes of Homalomena occulta and their anti-inflammatory activity

The rhizomes of Homalomena occulta are called Qian-nian-jian in Traditional Chinese Medicine (TCM), which is widely consumed in China owing to its health benefits for the treatment of rheumatoid arthritis and for strengthening tendons and bones. A phytochemical investigation on this famous TCM yielded 19 sesquiterpenoids (1–19) with various carbocyclic skeletons including isodaucane (2, 8, and 9), guaiane (3), eudesmane (4 and 10–15), oppositane (5, 16, and 17), and aromadendrane (18 and 19) types. The structures of new compounds, Homalomenins A-E (1–5), were determined by diverse spectroscopic data. Compound 1 possessed a rare sesquiterpenoid skeleton and compound 5 represented the first example of 1,4-oxa-oppositane sesquiterpenoid. These isolates were evaluated for their inhibitory effects on COX-2 mRNA, COX-2 protein expression, and prostaglandin E2 (PGE2) production in Raw264.7 cells, which demonstrated that compounds 5, 18, 19 showed potent anti-inflammatory activity by suppressing LPS-induced COX-2 expression and PGE2 production in a dose-dependent manner.     

Triterpenoid saponins from Clematis chinensis and their inhibitory activities on NO production

Four new triterpenoid saponins, clematochinenoside H–K (1–4), and five known structures (5–9), were isolated from the roots and rhizomes of Clematis chinensis. Their structures were elucidated on the basis of spectroscopic evidence and hydrolysis products. All isolates were evaluated for inhibitory effects against nitric oxide (NO) production in LPS-induced RAW 246.7 macrophages. Monodesmosidic saponins (1–3, 5, and 6) with a free carboxylic acid function at C-28 exhibited potent inhibitory activities with IC₅₀ values in the range of 12.9–32.3 μM, where as bisdesmosidic saponin (4, and 7–9) showed modest inhibitory effects with the inhibition ratios (%) from 39.9 to 59.0 at 50 μM. In addition, the hydroxyl group at C-21 showed negative effect on the NO production inhibitory activity.     

Chemical constituents from the stems of Tripterygium regelii

Phytochemical investigation on the stems of Tripterygium regelii resulted in the isolation of fourteen compounds, including six flavonoids (1–6), seven lignans (7–13), and one cyanogenic glycoside (14). This is the first report of the four dimeric flavonoids bis-8, 8′-catechinylmethane (2), bis (8-epicatechinyl) methane (3), bis-6, 8′-catechinylmethane (4) and montahomobisflavan B (5) from a species of Tripterygium. Previously, these dimeric flavonoids have been mainly identified from species of gymnosperms. This research has shown that the main secondary metabolisms identified in T. regelii were flavonoids and lignans. These data enable this species to be differentiated from T. wilfordii and T. hypoglaucum that contain the triptolide-resembling diterpenoids.     

Triterpene glycosides from red ginseng marc and their anti-inflammatory activities

Three new triterpene glycosides ursan-3β,19α,22β-triol-3-O-β-d-glucopyranosyl (2′→1″)-β-d-glucopyranoside (1), ursan-3α,11β-diol-3-O-α-d-glucopyranosyl-(6′→1″)-α-d-glucopyranosyl-(6″→1‴)-α-d-glucopyranosyl-(6‴→1‴′)-α-d-glucopyranoside (2) and lanost-5,24-dien-3β-ol-3-O-β-d-glucopyranosyl-(6′→1″)-β-d-glucopyranosyl-(6″→1‴)-β-d-glucopyranoside (3), together with one known compound were isolated and identified from the marc of red ginseng. Their structures were elucidated by spectroscopic data analysis. Compounds (1–3) were investigated for anti-inflammatory effects using the RAW 264.7 macrophage cell line. In the cell proliferation assay, lipopolysaccharide stimulation decreased cell proliferation of RAW 264.7 macrophage cells, but the suppression of cell proliferation was significantly protected by treatment with compounds 2 and 3. Compounds 2 and 3 had a suppressive effect on the production of nitric oxide (NO), and they inhibited mRNA expression of proinflammatory mediators such as inducible nitric oxide synthase, and cyclooxygenase-2, and proinflammatory cytokines such as two interleukins and tumor necrosis factor-α. These findings suggest that compounds 2 and 3 have potential anti-inflammatory activities.     

Anti-nociceptive,anti-inflammatory and sedative activities of the extracts and chemical constituents of Diospyros lotus L.

Diospyros lotus L. is traditionally used in various diseases including pain and sleep disorders. The pain and inflammation are the common problems, which are treated with various synthetic analgesic drugs, and associated the side effects. The natural products have gained significant importance over synthetic drugs. The importance of phyto-medicine the current study has been designed with the aim to investigate the analgesic and anti-inflammatory effects of Diospyros lotus and bioassay guided isolation from its crude fractions. Seven known compounds; lupeol (1), 7-methyljuglone (2), β-Sitosterol (3), stigmasterol (4) betulinic acid (5), diospyrin (6; DS) and 8-hydroxyisodiospyrin (7; HDS) which were hitherto unreported from D. lotus. The chloroform fraction (CFDL) and isolated compounds DS and HDS were evaluated for anti-nociceptive, sedative and anti-inflammatory effects. The acetic acid induced writing was significantly (p < 0.001) protected by CFDL (72.43%), DS (40.87%) and HDS (65.76%) at higher doses which exhibited peripheral and central analgesic effects in acetic acid and hot-plat pain paradigms. Regarding the anti-inflammatory effect the CFDL (77.43%), DS (80.54%) and HDS (75.87%) protected the carrageenan paw edema after 3rd h. The central analgesic effect was significantly antagonized with naloxone (0.5 mg/kg), showing opiodergic mechanism of action. The CFDL, DS and HDS were also proved sedative in open field animal models. In acute toxicity study the chloroform fraction [CFDL (50, 100 and 150 mg/kg)], DS (5 and 10 mg/kg) and HDS (5 and 10 mg/kg) were found safe.Our study concluded that CFDL, DS and HDS have marked anti-nociceptive, anti-inflammatory and sedative effect. The anti-nociceptive and anti-inflammatory effects of the roots of D. lotus are partially attributed due to the presence of analgesic constituents like diospyrin (DS), 8-hydroxyisodiospyrin (HDS) and strongly supports the ethno-pharmacological uses of D. lotus as anti-nociceptive, anti-inflammatory and sedative.     

Chemical constituents of the roots of Eupatorium chinense and their anti-inflammatory activities

In this study, three new compounds (1-3), together with fifteen known ones (4-18) were isolated from a petroleum ether extract of the roots of Eupatorium chinense. The structures of new compounds were elucidated by 1D, 2D nuclear magnetic resonance (NMR), circular dichroism spectrum (CD), mass spectrum (MS) along with other spectroscopy methods. In addition, twelve compounds were evaluated in vitro for their anti-inflammatory activities, while compounds 3 and 5 exhibited moderate activities with inhibition rates of 23.08 % and 25.19 %, respectively.