Nitrophenyl dihydropyridine-derivatives from Seriphidium oliverianum (original) (raw)
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Anti-urease Secondary Metabolites from Seriphidium quettense
2016
Ethyl acetate layer of the methanolic extract of Seriphidium quettense was subjected to silica gel column chromatography to isolate one new; seriphiloid (1), and four known compounds; ilicic acid (2), 6hydroxy-8(10)-oplopen-14-one (3), 2-(4-hydroxyphenyl)-5,6,7-trimethoxy-4H-chromen-4-one (4) and 2-(3,4dihydroxyphenyl)-5,6,7-trimethoxy-4H-chromen-4-one (5). The chemical structure of the new isolate was established with the help of 1D, 2D NMR techniques and high resolution mass spectrometry. Known compounds were identified because of 1D NMR and mass spectrometric analysis and in comparison with the literature values. Compounds 1-5 were evaluated for their acetylcholinesterase, butyrylcholinesterase, -glucosidase and urease inhibitory activities. Most of the metabolites were found inactive; however, compounds 2 and 3 showed good antiurease activity with IC50 value 21.5±0.1 and 20.8±0.1 μg/mL, respectively.
Journal of Traditional Chinese Medicine, 2018
OBJECTIVE: To investigate the antimicrobial activity, hemagglutination and phytotoxic activity of crude ethanolic and aqueous extracts of Seriphidium kurramense. METHODS: The extracts were analyzed by agar well diffusion assays against five bacterial species: Staphylococcus aureus (S. aureus), methicillin-resistant S. aureus, Escherichia coli, Klebsiella pneumoniae, Bacillus subtilis, and Salmonella typhi. The extracts were also screened against six fungal species-Aspergillus niger, Aspergillus flavus, Alternaria solani, Rhizoctonia solani, Fusarium solani and Pleurotus floridausing the agar tube diffusion method. Additionally, hemagglutination and phytotoxic activities of the crude ethanolic and aqueous extracts were assessed. RESULTS: The crude ethanolic and aqueous extracts showed dose-dependent inhibition of the various tested fungal and bacterial strains. No hemagglutination activity was observed. Both the ethanolic and aqueous extracts showed dose-dependent phytotoxic activity toward Lemna minor. CONCLUSION: The crude ethanolic and aqueous extracts of Seriphidium kurramense possess good antimicrobial and phytotoxic activities, but no hemagglutination activity.
Antimicrobial Activity of Crude Protein Extracts of Seriphidium kurramense
Asian Journal of Chemistry, 2016
Current study was aimed at investigating antibacterial and antifungal activities of crude protein extracts of Seriphidium kurramense. Agar well diffusion assays were performed to screen crude protein extracts against methicillin resistant Staphylococcus aureus, Escherichia coli, Klebsiella pneumoniae, Bacillus subtillus, Staphylococcus aureus and Salmonella typhi. Antifungal assay was carried out against Aspergillus niger, Aspergillus flavus, Alternaria solani, Rhizoctonia solani, Fusarium solani and Pleurotus florida. Different dilutions of crude protein extracts were used. The protein extracts showed antimicrobial activity against bacterial and fungal strains. However, pure extracts were more potent than a 1:1 dilution of protein extracts.
Secondary metabolites from Opuntia ficus-indica var. saboten
Phytochemistry, 2006
A butanol fraction, from the methanolic extract of Opuntia ficus-indica var. saboten, on purification either by preparative TLC or reversed phase HPLC, yielded three chemical components: isorhamnetin 3-O-(6 00 -O-E-feruloyl)neohesperidoside (1), (6R)-9,10-dihydroxy-4,7-megastigmadien-3-one-9-O-b-D-glucopyranoside and (6S)-9,10-dihydroxy-4,7-megastigmadien-3-one-9-O-b-D-glucopyranoside (3) along with 15 known compounds. Structures of compounds (1-3) were elucidated by aid of spectroscopic analyses. The absolute stereochemistry in compounds 2 and 3 was established with the help of CD data analysis and comparison with the literature data analysis. In a DPPH radical scavenging assay, compound 1 showed moderate inhibitory activity (IC 50 = 45.58 lg/ml).
Hepatoprotective Screening of Seriphidium kurramense (Qazilb.) Y.R. Ling
BioMed Research International, 2021
Investigation on medicinal plants' therapeutic potential has gained substantial importance in the discovery of novel effective and safe therapeutic agents. The present study is aimed at investigating the hepatoprotective potential of Seriphidium kurramense methanolic extract (SKM) against carbon tetrachloride- (CCl4-) induced hepatotoxicity in rats. S. kurramense is one of the most imperative plants for its various pharmacological activities. Therefore, this study was aimed at evaluating the hepatoprotective potential against CCl4-induced liver toxicity. The serum samples were analyzed for alanine aminotransferase (ALT) and aspartate aminotransferase (AST) together with the oxidative stress mediator levels as nitric oxide (NO), malondialdehyde (MDA), glutathione (GSH), reduced glutathione (GSH), and superoxide dismutase (SOD) as well as peroxidation and H2O2 activity. CCl4 administration resulted in an elevated free radical generation, altered liver marker (AST and ALT) enzymes,...
European Journal of Medicinal Chemistry, 2010
a b s t r a c t N-aryl-1,4-dihydropyridines 2a-n were synthesized via iodine catalyzed three-component reaction of cinnamaldehydes, anilines and 2-keto esters in methanol. The synthesized compounds were screened for their antidyslipidemic and antioxidant activity in vivo and in vitro. Compounds 2a, 2g, and 2l have exhibited promising lipid and TG lowering activity, whereas compounds 2m and 2n have showed potent antioxidant activity.
Pyridine-4(1H)-one Alkaloids from Waltheria indica as Antitrypanosomatid Agents
Journal of Natural Products, 2020
Twelve new pyridine-4(1H)-one derivatives, namely, 8-demethoxywaltherione F (1), waltheriones R−V (2, 6, 7, 10, and 11), 1-methoxywaltherione O (3), (S)-15-hydroxywaltherione G (4), (8R)-8-hydroxywaltherione M (5), (9S,13S)-2hydroxymethylwaltherione C (8), (9S,10S,13S)-10-hydroxywaltherione C (9), and (S)-13-methoxywaltherione V (12), as well as melovinone (13) and 5′-methoxywaltherione A (14) were isolated from the CH 2 Cl 2 extract of the aerial parts of Waltheria indica. Their chemical structures were determined by means of a comprehensive analysis including 1 H NMR, DEPTQ, HSQC, HMBC, 1 H− 1 H COSY, ROESY, and HRESIMS data. The absolute configurations were assigned via comparison of the experimental and calculated ECD data. In addition, the isolated constituents as well as the known waltheriones M−Q were evaluated for their in vitro antitrypanosomal activity. Compounds 2, 5, and 7 as well as waltheriones M, P, and Q showed potent growth inhibition toward Trypanosoma cruzi with IC 50 values of 2.1, 0.8, 2.1, 1.3, 0.5, and 0.1 μM, respectively, and selectivity indices of >12, >33, >13, 5, 25, and 14. These findings further demonstrate that the waltheriones are a promising class of antichagasic compounds worthy of further investigations.
Journal of Medicinal Plants Research, 2010
Seriphidium kurramense is an endemic and economic medicinal plant growing in a small narrow valley of tribal region in Pakistan, Upper Kurram Agency, at Pakistan-Afghanistan border. GC-MS analysis of essential oils of S. kurramense identified 28 chemical constituents from 16 populations with two distinct chemotypes, A and B. Both chemotypes represented similar morphological features. Major chemical constituents of chemotype A comprising 12 populations, consisted of-thujone (26.0-73.4 %),-thujone (3.14-49.3 %), 1,8-cineole (10.2-22.3 %) and camphor (0-26.3 %), while the major chemical constituents of chemotype B from four populations were p-menthan-1,8-diol (23.1-35.2 %), 1,8-cineole (10.2-23.8 %) and an unknown chemical compound (12.5-25.9 %). Significant differences in toxicity levels were observed in all the 16 populations of S. kurramense. Chemotype B showed highest root and Hypocotyle inhibition of lettuce seeds as compared to Chemotype A.
Chemical Constituents of Nitraria retusa Grown in Egypt
Chemistry of Natural Compounds, 2017
Nitraria retusa Asch. is one of the native perennial halophyte species that belongs to the botanical family Nitrariaceae (Zygophyllaceae). It is a resistant shrub that grows in steppes and saline deserts, distributed in North Africa and restricted to Algeria, Egypt, and Tunisia >1, 2@. Previous phytochemical studies on N. retusa have led to the identification of a variety of compounds that include mainly flavonoids and their corresponding glucosides >3-7@. Recently, the phytochemical study of a Jordanian Nitraria retusa led to the isolation of two new quinazoline alkaloids, namely 5,7-dihydroxy-3-deoxyvasicine and 7-hydroxy-3-deoxy-1-vasiciene together with the known O-acetylnitraraine >8@. Due to our continuing interest in the chemical diversity of plants belonging to the Nitraria genus >9, 10@, we investigated the aerial parts of N. retusa growing in Egypt. Thus, we report herein the isolation and identification of three known compounds: two aromatics, vanillamide (1) and PABA (2), and one lignan, (+)-epi-syringaresinol (3). The description of the above-mentioned metabolites is noteworthy, as they have hitherto never been encountered in Nitraria species. Although the Nitraria genus is known to be rich in terms of diversity of alkaloids if not amounts, the alkaloidic extraction of the Egyptian N. retusa afforded only a small amount of material compared to its Jordanian congener. Furthermore, when the alkaloid extract was tested for the presence of alkaloids using Mayercs and Dragendorffcs reagents, the tests were negative. The absence of alkaloids in the so-called "alkaloidic extract" caught our attention and led us to analyze the methanolic one. Its extracted UV and MS data indicated characteristic evidences reminiscent of tricyclic quinazoline alkaloids >11@. Therefore, the putative detection of alkaloids in the methanolic extract may explain their absence in the alkaloid one. Indeed, due to their low basicity, alkaloids of the Egyptian N. retusa could not be extracted by the classical alkaloid extraction. On the other hand, the putative MS-based detection of the aforementioned tricylic quinazoline alkaloids in the methanolic extract of N. retusa is not an unexpected feature, because they were also identified in N. schoberi >10@, N. sibirica >12@ and N. komarovii >13@. Moreover, the distribution in Nature of the tricyclic quinazoline alkaloids, biosynthetically derived from anthranilic acid, is not restricted by the frameworks of any one or more taxonomic units. They are found most often in plants of the genera Peganum, Galega, Adhadota, Nitraria, Mackinlaya, etc. >14@. General. Optical rotations were measured at 25qC on an Anton Paar MCP200 polarimeter. UV spectra were recorded on a PerkinElmer Lambda 5 spectrophotometer. IR spectra were recorded with a Vector 22 Bruker spectrometer. The NMR spectra were recorded on Bruker AM-300 (300 MHz), AM-400 (400 MHz) apparatus using DMSO-d 6 , CD 3 OD, as solvents. HR-ESI-MS and LC/MS were run on a Thermoquest TLM LCQ Deca ion-trap spectrometer with an XBridge analytical C 18 column (150 u 2.1 mm; 3.5 Pm, Waters) and a preparative (150 u 19 mm, 5 Pm, Waters). Sunfire preparative C 18 columns (150 u 30 mm; i.d. 5 Pm, Waters) was used for preparative HPLC separations using a Waters Delta Prep column equipped with a binary pump (Waters 2525) and a UV-visible diode array detector (190-600 nm, Waters 2996). All other chemicals and solvents were purchased from Aldrich and SDS (France).
Hepatoprotective Screening of Seriphidium kurramense (Qazilb.)
2021
College of Life Science, Anhui Normal University, Wuhu 241000, China Leibniz Institute of Plant Biochemistry, Department of Bioorganic Chemistry, D-06120 Halle (Saale), Germany Department of Chemistry, University of Okara, Okara, Pakistan Department of Chemistry, University of Swabi, Anbar KPK, Pakistan Department of Botany, Government Post Graduate College Parachinar, Kurram 26000, Pakistan Department of Botany, University of Science & Technology Bannu, Pakistan Department of Biochemistry, Faculty of Biological Sciences, Quaid-i-Azam University, Islamabad, Pakistan Department of Biology, Faculty of Science, University of Tabuk, Tabuk, Saudi Arabia Department of Biology, Faculty of Science, Ibb University, Ibb, Yemen Department of Biochemistry, Abubakar Tafawa Balewa University, Bauchi 740272, Nigeria Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia Department of Pharmaceutical Chemistry, College of Pharmacy, King Khalid Un...