0000000000016681
AUTHOR
Tarik A. Mohamed
Cytotoxic and chemotaxonomic study of isolated metabolites from Centaurea aegyptiaca
Oxygenated Cembrene Diterpenes from Sarcophyton convolutum: Cytotoxic Sarcoconvolutum A–E
The soft coral genus Sarcophyton contains the enzymatic machinery to synthesize a multitude of cembrene-type diterpenes. Herein, highly oxygenated cembrenoids, sarcoconvolutum A–E (1–5) were purified and characterized from an ethyl acetate extract of the red sea soft coral, Sarcophyton convolutum. Compounds were assemblies according to spectroscopic methods including FTIR, 1D- and 2D-NMR as well as HRMS. Metabolite cytotoxicity was tested against lung adenocarcinoma, cervical cancer, and oral-cavity carcinoma (A549, HeLa and HSC-2, respectively). The most cytotoxic compound, (4) was observed to be active against cell lines A549 and HSC-2 with IC50 values of 49.70 and 53.17 μM, respectively.
In silico drug discovery of major metabolites from spices as SARS-CoV-2 main protease inhibitors
Coronavirus Disease 2019 (COVID-19) is an infectious illness caused by Severe Acute Respiratory Syndrome Coronavirus 2 (SARS-CoV-2), originally identified in Wuhan, China (December 2019) and has since expanded into a pandemic. Here, we investigate metabolites present in several common spices as possible inhibitors of COVID-19. Specifically, 32 compounds isolated from 14 cooking seasonings were examined as inhibitors for SARS-CoV-2 main protease (Mpro), which is required for viral multiplication. Using a drug discovery approach to identify possible antiviral leads, in silico molecular docking studies were performed. Docking calculations revealed a high potency of salvianolic acid A and curcu…
Recent Advances in Kaempferia Phytochemistry and Biological Activity : A Comprehensive Review
Background: Plants belonging to the genus Kaempferia (family: Zingiberaceae) are distributed in Asia, especially in the southeast region, and Thailand. They have been widely used in traditional medicines to cure metabolic disorders, inflammation, urinary tract infections, fevers, coughs, hypertension, erectile dysfunction, abdominal and gastrointestinal ailments, asthma, wounds, rheumatism, epilepsy, and skin diseases. Objective: Herein, we reported a comprehensive review, including the traditional applications, biological and pharmacological advances, and phytochemical constituents of Kaempheria species from 1972 up to early 2019. Materials and methods: All the information and reported stu…
Sarcoehrenbergilides D–F: cytotoxic cembrene diterpenoids from the soft coral Sarcophyton ehrenbergi
A solvent extract of the soft coral Sarcophyton ehrenbergi afforded cembrene diterpenoids, sarcoehrenbergilid D–F (1–3). Chemical structures were established by modern spectroscopic techniques with absolute stereochemistries determined by circular dichroism (CD) and time-dependent density functional theory electronic CD calculations (TDDFT-ECD). Cytotoxicity activities for 1–3 were evaluated against three human cancer cell lines: lung (A549), colon (Caco-2) and liver (HepG2).
Two novel oxetane containing lignans and a new megastigmane from Paronychia arabica and in silico analysis of them as prospective SARS-CoV-2 inhibitors
The chemical characterization of the extract of the aerial parts of Paronychia arabica afforded two oxetane containing lignans, paronychiarabicine A (1) and B (2), and one new megastigmane, paronychiarabicastigmane A (3), alongside a known lignan (4), eight known phenolic compounds (5–12), one known elemene sesquiterpene (13) and one steroid glycoside (14). The chemical structures of the isolated compounds were constructed based upon the HRMS, 1D, and 2D-NMR results. The absolute configurations were established via NOESY experiments as well as experimental and TDDFT-calculated electronic circular dichroism (ECD). Utilizing molecular docking, the binding scores and modes of compounds 1–3 tow…
Antiulcer activity of Cyperus alternifolius in relation to its UPLC-MS metabolite fingerprint: A mechanistic study
Abstract Background Gastric ulcer is one of the main prevalent gastrointestinal multi-etiological disorders with many associated complications and adverse effects. Our aim was to develop safer antiulcer therapies based on methanol or ethyl acetate extracts of tubers and aerial parts from Cyperus alternifolius. Methods Gastric ulceration was experimentally generated by administration of single oral doses of indomethacin (30 mg/kg) to fasted rats. The animals received methanol or ethyl acetate extracts of C. alternifolius tuber and methanol or ethyl acetate extracts of aerial parts at two dose levels (50 or 100 mg/kg). Ranitidine (50 mg/kg) was used as standard anti-ulcer drug. After 4 h, the…
New antimicrobial metabolites from the medicinal herb Artemisia herba-Alba
Artemisia herba-alba is widely used in traditional medicines for the treatment of several diseases. From the aerial parts organic extract of A. herba-alba, two new compounds, 1,3,8-trihydroxyeudesm-4-en-7α,11βH-12,6α-olide (1) and 5-β-D-glucopyranosyloxy-7-methoxy-6H-benzopyran-2-one (2), respectively, together with five known metabolites: 3α,8β-dihydroxygermacr-4(15),9(10)-dien-7β,11αH,12,6α-olide (3), 1β,8α-dihydroxy-11α,13-dihydrobalchanin (4), 11-epiartapshin (5), tomenin (6) and benzoic acid, p-(β-D-glucopyranosyloxy)-methyl ester (7), were isolated and identified. The chemical structures were proven depending upon spectroscopic analysis, including 1 D/2D NMR as and ESI-MS…
The natural compound chrysosplenol-D is a novel, ultrasensitive optical sensor for detection of Cu(II)
Abstract Herein, we introduce a novel, ultrasensitive optical sensor for determination of Cu(II) ions over the concentration range of 0 to 1 μM Cu(II). The optical sensor is based on the natural molecule chrysosplenol-D (Chp-D) extracted from the flowering plant Chiliadenus montanus (Vahl.) Brullo. Free Chp-D emits fluorescence at 566 nm when excited at 292 nm. Chp-D chelates Cu(II) ions to form a 1:1 (metal:ligand) complex, which quenches the fluorescence emission peak of the free probe at 566 nm. “Turn-off” luminescence could be easily determined and provided distinct proof of the chelation of Cu(II) ions by Chp-D. This novel optical sensor offers a considerable fluorescence mechanism (ch…
Euphosantianane E–G: Three New Premyrsinane Type Diterpenoids from Euphorbia sanctae-catharinae with Contribution to Chemotaxonomy
Euphorbia species were widely used in traditional medicines for the treatment of several diseases. From the aerial parts of Egyptian endemic plant, Euphorbia sanctae-catharinae, three new premyrsinane diterpenoids, namely, euphosantianane E&ndash
Phytochemical constituents and chemosystematic significance of Pulicaria jaubertii E.Gamal-Eldin (Asteraceae)
Abstract The chemical characterization of methylene chloride/methanol (1:1) extract of the air-dried whole medicinal plant, Pulicaria jaubertii E. Gamal-Eldin, led to isolation and identification of two new hydroquinone compounds; 2-(2-acetoxy propyl), 5-methyl hydroquinone (1) and 2-(2-hydroxy propyl), 5-methyl hydroquinone-4-O-β-D-glucopyranoside (2), four known flavonols (3-6) and 7 known dihydroflavonols (7-13). The structures were established depending upon comprehensive analysis of the NMR, IR and HR/EI-MS data. Herein, compounds 6, and 10-13 were isolated for the first time from this plant. The chemotaxonomic significance of the isolated flavonoids from P. jaubertii comparing with th…
Cytotoxicity of 40 Egyptian plant extracts targeting mechanisms of drug-resistant cancer cells
Abstract Background The multidrug resistance (MDR) phenotype encounters a major challenge to the success of established chemotherapy in cancer patients. We hypothesized that cytotoxic medicinal plants with novel phytochemicals can overcome MDR and kill MDR-cells with similar efficacy as drug sensitive cells. Purpose We evaluated plant extracts from an unexplored ecosystem in Egypt with unusual climate and nutrient conditions for their activity against sensitive and multidrug-resistant cancer cell lines. Material and methods/study design Methylene chloride: methanol (1:1) and methanol: H2O (7:3) extracts of 40 plants were prepared resulting in a sum of 76 fraction containing compounds with v…
Cytotoxic polyoxygenated isopimarane diterpenoids from the edible rhizomes of Kaempferia galanga (kencur)
Abstract Kaempferia galanga (Family Zingiberaceae) is a widely distributed Asian medicinal plant and cultured crop. Several traditional uses of the rhizomes of this plant have been reported with widely using as flavors and spice in cooking. The present work concerned the isolation and identification as well as antiproliferative activity of metabolites of the rhizomes of K. galanga. Three new polyoxygenated isopimarane diterpenoids, kaemgalangols B-D (1-3), were isolated and identified in addition to 20 knowns (4-27), one monoterpene (28), and five known phenolic compounds (29-33). The chemical structures of the isolated compounds were established mainly based upon the spectroscopic analysis…
Terpenoid bio-transformations and applications via cell/organ cultures: a systematic review.
Structurally diverse natural products are valued for their targeted biological activity. The challenge of working with such metabolites is their low natural abundance and complex structure, often with multiple stereocenters, precludes large-scale or unsophisticated chemical synthesis. Since select plants contain the enzymatic machinery necessary to produce specialized compounds, tissue cultures can be used to achieve key transformations for large-scale chemical and/or pharmaceutical applications. In this context, plant tissue-culture bio-transformations have demonstrated great promise in the preparation of pharmaceutical products. This review describes the capacity of cultured plant cells t…
Antibacterial activity and cytotoxicity of selected Egyptian medicinal plants.
Medicinal plants have been used as a source of remedies since ancient times in Egypt. The present study was designed to investigate the antibacterial activity and the cytotoxicity of the organic extracts from 16 selected medicinal plants of Egypt. The study was also extended to the isolation of the antiproliferative compound jaeschkeanadiol p-hydroxybenzoate (FH-25) from Ferula hermonis. The microbroth dilution was used to determine the minimal inhibitory concentration (MIC) of the samples against twelve bacterial strains belonging to four species, Providencia stuartii, Pseudomonas aeruginosa, Klebsiella pneumoniae, and Escherichia coli, while a resazurin assay was used to assess the cytoto…
New phenolics, cytotoxicity and chemosystematic significance of Atriplex semibaccata
Abstract The chemical characterization of the 70% hydromethanolic extract of Atriplex semibaccata (family: Chenopodiaceae) afforded a new methoxylated flavonol triglycoside, atrisemibaccatoside A (1), and a new lignanamide, (N-[(E)-m-hydroxycinnamoyl]tyramine (7), as well as, five known flavonols (2–6) and two lignanamides (8–9). The structures of the isolated compounds were established depending upon LR&HR-FAB-MS, 1D and 2D NMR spectroscopic analyses. The cytotoxic activity of the isolated compounds (1–4, and 7–9) was investigated. Compounds 7, 8 and 9 weakly inhibited the proliferation of leukemia CCRF-CEM cells with IC50 values of 78.5, 46.3, and 71.2 μg/ml, respectively, and exhibited n…
Two new diterpenoids from kencur (Kaempferia galanga): Structure elucidation and chemosystematic significance
Abstract Aromatic ginger or kencur (Kaempferia galanga L.) rhizomes are ground as a spice or pickled for consumption in south-east Asian cuisines; although widely used, until recently it has been less studied chemically than white and red ginger. Hydro-distillate extracts have identified several compounds that exhibit anticancer activity against select tumor cell lines in vitro, and most recently chemical analyses have focused on rhizome metabolites present in organic extracts. Here we report on two new diterpenoids including Δ8(14),15 polyhydroxlated isopimardienes, 1α-hydroperoxy-2α,6,7-trihydroxy-isopimara-6(7),8(14),15-triene (kaemgalangol E; 1) and 1α,7β-hydroxy-isopimara-8(14),15-dien…
Cytotoxic neo-clerodane diterpenes from Stachys aegyptiaca
Abstract Two new E/Z neo-clerodane diterpene isomers, trivially named stachaegyptin D (1) and E (2), together with known compounds, stachysolon monoacetate (3) and stachysolon diacetate (4), were isolated from an organic-solvent extract of the medicinal herb Stachys aegyptiaca. Structures were elucidated by a combination of spectroscopic methods, including HREIMS, 1H, 13C, DEPT, and 2D NMR analysis, as well as, first time X-ray analysis for stachysolone (3). All isolated metabolites showed some activity against the human hepatocellular cell line, HepG2. Compound 4 was the most active with an IC50 of 59.5 μM.