scholarly journals Unusual Secondary Metabolites of the Aerial Parts of Dionysia diapensifolia Bioss. (Primulaceae) and Their Anti-Inflammatory Activity

Biomolecules ◽  
2020 ◽  
Vol 10 (3) ◽  
pp. 438
Author(s):  
Mostafa Alilou ◽  
Stefania Marzocco ◽  
Hossein Batooli ◽  
Jakob Troppmair ◽  
Stefan Schwaiger ◽  
...  

The genus Dionysia, belonging to the Primulaceae family, encompasses more than 50 species worldwide with a center of diversity located in the arid Irano-Turanian mountains. In this study, a phytochemical investigation of the aerial parts of D. diapensifolia Bioss. led to the isolation of 24 phenolic compounds 1–7 and 9–25, and one sesquiterpenoid 8. Compound 1 was identified as new natural product, while isolation of 2 and 3, already known as synthetic products, from a natural source is reported for the first time in the present study. Isolation of compound 8 from a Dionysia species and indeed the whole Primulaceae family is reported for the first time too. Structure elucidation was performed by extensive spectroscopic analyses (1D-, 2D-NMR, and MS), and by comparison with reported literature data. Furthermore, DP4+ chemical shift probability calculations were performed to establish the relative configuration of compound 1. Additionally, subfractions obtained by liquid-liquid extraction of the methanolic extract of the plant, and subsequently the isolated new and selected known compounds 1–4, 6, 8–11 obtained from the diethyl ether subfraction were investigated for their inhibitory effect on NO release and iNOS and COX-2 expression in J774A.1 murine macrophages. The results showed a potential anti-inflammatory activity of the obtained subfractions, of which the diethyl ether subfraction was the most active one in inhibiting NO release and COX-2 expression (p < 0.001). Among the investigated isolated compounds, compound 4 significantly (p < 0.001) inhibited NO release and iNOS and COX-2 expression in a comparable manner like the used positive controls (L-NAME and indomethacin, respectively). Moreover, other isolated substances displayed moderate to high inhibitory activities, illustrating the potential anti-inflammatory activity of Dionysia diapensifolia.

2012 ◽  
Vol 7 (4) ◽  
pp. 1934578X1200700 ◽  
Author(s):  
Sung-Fei Hsieh ◽  
Tain-Jye Hsieh ◽  
Mohamed El-Shazly ◽  
Ying-Chi Du ◽  
Chin-Chung Wu ◽  
...  

Two new eremophilenolides, 6β8β10β-trihydroxyeremophil-7(11)-en-12,8-olide (1) and 3βacetoxy-8α-hydroxy-6β-methoxyeremophila-7(11),9-dien-12,8-olide (2) along with twenty-nine other compounds were obtained from the methanolic extracts of the aerial parts and rhizomes of Farfugium japonicum (L.) Kitam. v ar. formosanum (Hayata) Kitam. (Compositae = Asteraceae). The structures of the isolated compounds were characterized and identified by spectral techniques. Compounds 5, 6, 10, 12-24, 29, and 30, were reported for the first time from this genus. Cytotoxicity and anti-inflammatory activity of the isolated compounds were evaluated. Compounds 3 and 16 possessed moderate cytotoxicity against human breast cancer cell line (MCF 7). Compounds 3, 16, 25 and 26 exhibited moderate cytotoxicity against hepatoma cells (Hep G2 and Hep 3B). With respect to the anti-inflammatory activity, compounds 15 and 16 (each 10 μg/mL) inhibited superoxide anion generation by human neutrophils in response to fMLP/CB by 92.0% and 87.3%, respectively.


2012 ◽  
Vol 64 (3) ◽  
pp. 1059-1063 ◽  
Author(s):  
Jamal Elmezogi ◽  
Abdulmottaleb Zetrini ◽  
Ghazala Ben-Hussein ◽  
Masoud Anwair ◽  
Abdul Gbaj ◽  
...  

Ballota pseudodictamnus (L.) Benth. (Lamiaceae), Salvia fruticosa Mill. (Lamiaceae) and Thapsia garganica L. (Apiaceae) are three well-known medicinal plants from the Libyan flora, which have long been used for the treatment of inflammations. The aim of the present study was to investigate, for the first time, the anti-inflammatory property of the methanol (MeOH) extracts of the aerial parts of these plants. Shade-dried and ground aerial parts of B. pseudodictamnus, S. fruticosa) and T. garganica were Soxhlet-extracted with MeOH. The extracts were concentrated by evaporation under reduced pressure at 40?C. The anti-inflammatory activity of the extracts was evaluated using the carrageenan-induced mice paw edema model. The administration of the extracts at a dose of 500 mg/kg body weight produced statistically significant inhibition (p < 0.05) of edema within 3 h of carrageenan administration. The results demonstrated significant anti-inflammatory properties of the test extracts. Among the extracts, the S. fruticosa extract exhibited the most significant inhibition of inflammation after 3 h (62.1%). Thus, S. fruticosa could be a potential source for the discovery and development of newer anti-inflammatory ?leads? for drug development. The anti-inflammatory activity of B. pseudodictamnus and S. fruticosa could be assumed to be related to high levels of phenolic compounds, e.g., flavonoids, present in these plants.


2009 ◽  
Vol 32 (1) ◽  
pp. 75-78 ◽  
Author(s):  
Premysl Landa ◽  
Ladislav Kokoska ◽  
Marie Pribylova ◽  
Tomas Vanek ◽  
Petr Marsik

2006 ◽  
Vol 61 (3-4) ◽  
pp. 165-170 ◽  
Author(s):  
Paolo Grassi ◽  
Tomás S. Urías Reyes ◽  
Silvio Sosa ◽  
Aurelia Tubaro ◽  
Otmar Hofer ◽  
...  

Separation and isolation of the two main compounds suaveolol and methyl suaveolate from leaves of chichinguaste (Hyptis suaveolens Poit., Lamiaceae) could be achieved by means of repeated column chromatography and repeated preparative thin layer chromatography. Their chemical structures were approved by MS, 1H NMR, 13C NMR and 2D-NMR experiments. The anti-inflammatory activity of the two compounds was tested for the first time as inhibition of croton oil-induced dermatitis of the mouse ear. Suaveolol and methyl suaveolate showed nearly the same dose-dependent topical anti-inflammatory activity, only two to three times lower than that of the reference drug indomethacin. The anti-inflammatory properties of these compounds could contribute to the antiphlogistic activity of extracts of Hyptis species and confirm the rational use of Hyptis suaveolens extracts in dermatological diseases.


2018 ◽  
Vol 13 (3) ◽  
pp. 1934578X1801300
Author(s):  
Erzsébet Háznagy-Radnai ◽  
Laura Fási ◽  
Edit Wéber ◽  
Gyula Pinke ◽  
Gergely Király ◽  
...  

Melampyrum barbatum Waldst. & Kit. ex Willd. (Scrophulariaceae) has been used in traditional medicine for the treatment of rheumatic complaints and different skin diseases. In the course of our study the anti-inflammatory activity of the aerial parts of M. barbatum was evaluated. A MeOH extract was prepared and consecutively partitioned with CHCl3, EtOAc and n-BuOH. The fractions were assayed in in vivo carrageenan-induced rat paw oedema model. The intraperitoneally administered n-BuOH phase exerted marked inhibitory effect (33.6 %, p < 0.01). Multistep chromatographic separation afforded mussaenoside and aucubine from n-BuOH fraction. Moreover, 8-epiloganin, loganic acid and mussaenoside were obtained from EtOAc fraction and apigenin, luteolin, benzoic acid and galactitol from CHCl3 fraction. These data validate the ethnomedicinal use of M. barbatum for the treatment of inflammatory diseases and reveal that iridoids and flavonoids could be responsible for the anti-inflammatory effect of this species.


2015 ◽  
Vol 10 (1) ◽  
pp. 1934578X1501000 ◽  
Author(s):  
Daniel Winekenstädde ◽  
Apostolis Angelis ◽  
Birgit Waltenberger ◽  
Stefan Schwaiger ◽  
Job Tchoumtchoua ◽  
...  

The aim of this study was to investigate the phytochemical profile of the methanol extract of the aerial parts of Sedum sediforme and to identify its secondary metabolites. By means of chromatographic separation and enrichment of compounds, HPLC-ESI-MS, HRMS, 1D-, 2D- NMR and/or comparison with reference compounds, three triterpenes, two sterols, ten flavonoids and twelve phenolic compounds were identified, together with two new compounds, i.e. (2 R*, 3 R*)-5,7-dihydroxy-2,3-dimethyl-4-chromanone-7- O-ß-D-glucoside (27) and butan-2- O-rutinoside (28). Out of the 29 identified secondary metabolites, 18 are described as ingredients of S. sediforme herein for the first time. Furthermore, myricitrin, one of the major constituents, was tested for its ability to inhibit different enzymes within the arachidonic acid cascade in order to determine its anti-inflammatory properties. Whereas there was only either weak or no inhibition of the microsomal prostaglandin E2 synthase-1 (mPGES-1) and the soluble epoxide hydrolase (sEH), myricitrin showed strong inhibition of 5-lipoxygenase (5-LO), with an IC50 of 7.8 ± 0.2 μM.


2020 ◽  
Vol 2020 ◽  
pp. 1-11
Author(s):  
Alice Nabatanzi ◽  
Sanah M. Nkadimeng ◽  
Namrita Lall ◽  
John D. Kabasa ◽  
Lyndy J. McGaw

Kigelia africana is used to manage inflammation among indigenous communities. We hypothesized that K. africana extracts contain phytoconstituents with good antioxidant and anti-inflammatory activities. The methanolic extract of K. africana fruits and Spathodea campanulata leaves (SPK04), K. africana aqueous fruit extract (KFM02), and K. africana acetone fruit extract (KFM05) were subjected to antioxidant and anti-inflammatory assays. Antioxidant activity was evaluated using the ABTS radical scavenging assay, and the MTT cell viability assay was used for cytotoxicity. The extracts were preincubated with enzymes and assayed for 15-LOX and COX-2 enzyme activity using an ELISA method. Nitric oxide (NO) inhibitory effect of the extracts was evaluated and measurement of proinflammatory cytokines (IL-1β, TNF-α, and IL-6) and the anti-inflammatory cytokine (IL-10) was done using ELISA kits. SPK04 had the highest antioxidant activity with a mean inhibition of 99.37 ± 0.56% and an IC50 of 4.28 µg/mL. SPK04 and KFM05 did not inhibit 15-LOX as their IC50 values were >1000 μg/mL. All extracts were safe on Vero cells at the highest concentration (200 µg/mL) tested. KFM02 was the best inhibitor of NO production and had the highest cell viability at both the lowest (50 µg/mL) and highest concentrations (200 µg/mL). SPK04 was the best COX-2 inhibitor while KFM05 expressed the strongest suppression effect for IL-β and IL-6. KFM02 did not inhibit IL-6 at the highest concentration (200 µg/mL). The order of suppression of TNF-α by the extracts differed across concentrations, KFM05 > SPK04 > KFM02 at 200 µg/mL, KFM02 > SPK04 > KFM05 at 100 µg/mL, and SPK04 > KFM02 > KFM05 at 50 µg/mL. All the tested extracts had no inhibitory effect against IL-10. SPK04, KFM05, and KFM02 had good antioxidant and anti-inflammatory activity and this supports their use as potential anti-inflammatory therapies. This study presents for the first time the antioxidant and anti-inflammatory activity of K. africana and S. campanulata polyherbal extract. It is also among the very few studies that have reported the inhibitory effect of cytokines IL-1β, TNF-α, IL-6, and IL-10 by K. africana.


2021 ◽  
Vol 12 ◽  
Author(s):  
Qianqian Xu ◽  
Yuben Qiao ◽  
Zijun Zhang ◽  
Yanfang Deng ◽  
Tianqi Chen ◽  
...  

Two new polyketide compounds, asperulosins A and B (1–2), and one new prenylated small molecule, asperulosin C (3), along with nine known compounds (4–12), were isolated and identified from a fungus Aspergillus rugulosa. Their structures were extensively elucidated via HRESIMS, 1D, and 2D NMR analysis. The absolute configurations of the new compounds were determined by the comparison of their electronic circular dichroism (ECD), calculated ECD spectra, and the detailed discussion with those in previous reports. Structurally, compounds 1 and 2 belonged to the polyketide family and were from different origins. Compound 2 was constructed by five continuous quaternary carbon atoms, which occur rarely in natural products. All of the isolates were evaluated for anti-inflammatory activity against the production of nitric oxide (NO) in lipopolysaccharide (LPS)-induced RAW264.7 cells. Among those, compounds 1 and 5 showed a significant inhibitory effect on NO production with IC50 values of 1.49 ± 0.31 and 3.41 ± 0.85 μM, respectively. Additionally, compounds 1 and 5 markedly increased the secretion of anti-inflammatory cytokine IL10 while suppressing the secretion of pro-inflammatory cytokines IL6, TNF-α, IFN-γ, MCP-1, and IL12. Besides, 1 and 5 inhibited the transcription level of pro-inflammatory macrophage markers IL6, IL1β, and TNF-α while remarkably elevating the anti-inflammatory factor IL10 and M2 macrophage markers ARG1 and CD206. Moreover, 1 and 5 restrained the expression and nuclear translocation of NF-κB, as well as its downstream signaling proteins COX-2 and iNOS. All these results suggest that 1 and 5 have potential as anti-inflammatory agents, with better or comparable activities than those of the positive control, dexamethasone.


2021 ◽  
pp. 17-24
Author(s):  
Ifora Ifora ◽  
Bella Sintia ◽  
Yoneta Srangenge

Inflammation is a normal protective response to tissue damage that mediated by Cyclooxygenase-2 (COX-2) enzyme. The enhancement incidence and impact of inflammatory diseases have encouraged the search for new pharmacological strategies to overcome the problem. Ketumbar (Coriandrumsativum L.) has been traditionally used as an anti-inflammatory and antioxidant, thus giving chance for anti-inflammatory studies. This study aims to determine the ethanol extract of Ketumbar (Coriandrumsativum L.) leaves anti-inflammatory activity and inhibitory effect on COX-2 enzyme. This study uses male wistar rats with 180–220 g body weights. The rats is divided into six groups by the dose of 125 mg/kg BW, 250 mg/kg BW, and 500 mg/kg BW; positive control (Carrageenan 1%); negative control (Na. CMC 0,5%); and comparative group (Celecoxib 9 mg/kg BW). Determining the anti-inflammatory activity, the oedema formation is measured using a plethysmometer and the inhibition activity is determined by ELISA methods. The results showed that the ethanol extract of Ketumbar leaves by the dose of 125 mg/kg BW, 250 mg/kg BW, and 500 mg/kg BW was significantly inhibitted COX-2 valued 65,61%, 76,83%, and 62,93%. The anti-inflammatory activity was shown by inhibiting oedema valued of 62.26%, 70.59%, and 54.90% respectively. These findings suggested that the ethanol extract of Ketumbar leaves had anti-inflammatory activity, that was possibly mediated through inhibition of COX-2 enzymes


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