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Chemical Constituents with Free-Radical-Scavenging Activity from the Leaves of Lantana montevidensis (Spreng.) Briq.

Research Abstract
Background: Seventy percent aqueous methanolic extract of the leaves of Lantana montevidensis exhibited antibacterial, anti-inflammatory, anti-pyretic, antioxidant, and analgesic activities. Previous phytochemical study of the leaves led to the isolation of various flavones, pentacyclic triterpenoids, β-sitosterol and benzoic acid. Materials and Methods: The 70% aqueous methanolic extract of L. montevidensis (Spreng.) Briq. leaves was partitioned between water and n-hexane, CHCl3, EtOAc, and n-BuOH, successively. By using a series of different chromatographic techniques, the CHCl3 and EtOAc extracts afforded nine compounds. The isolated compounds were identified by spectroscopic techniques and by comparison with literature values and/or authentic samples. The free radical scavenging activity of some of the isolated compounds was evaluated. Results: Hispidulin-7-O-glucurnoide methyl ester (1), hispidulin-7-O-glucoside (2), cinaroside (3), nepetin-7-O-glucoside (4) pectolinarigenin (5), apigenin (6), luteolin (7) in addition to salicylic acid (8) and β-sitosterol-3-O-glucoside (9) have been isolated. Compounds 1-4 are first report from the genus Lantana, whereas compounds 5, 8 and 9 are first report from this plant. The structures of these compounds were elucidated on the basis of spectral methods, including 2D nuclear magnetic resonance experiments, and confirmed by comparing with the literature data and/or authentic samples. Additionally, some of the isolated flavonoids exhibited free radical scavenging activity. Conclusion: L. montevidensis (Spreng.) Briq. cultivated in Egypt is rich in biologically active ingredients.
Research Authors
Makboul A. Makboul, Ahmed A. Attia, Salwa Farouk Farag, Nesma M. Mohamed, Samir A. Ross
Research Department
Research Journal
Phcog. J., DOI: 10.5530/pj.2014.6.6
Research Member
Research Rank
1
Research Vol
Vol. 6, No. 6
Research Year
2014

Chemical Constituents with Free-Radical-Scavenging Activity from the Leaves of Lantana montevidensis (Spreng.) Briq.

Research Abstract
Background: Seventy percent aqueous methanolic extract of the leaves of Lantana montevidensis exhibited antibacterial, anti-inflammatory, anti-pyretic, antioxidant, and analgesic activities. Previous phytochemical study of the leaves led to the isolation of various flavones, pentacyclic triterpenoids, β-sitosterol and benzoic acid. Materials and Methods: The 70% aqueous methanolic extract of L. montevidensis (Spreng.) Briq. leaves was partitioned between water and n-hexane, CHCl3, EtOAc, and n-BuOH, successively. By using a series of different chromatographic techniques, the CHCl3 and EtOAc extracts afforded nine compounds. The isolated compounds were identified by spectroscopic techniques and by comparison with literature values and/or authentic samples. The free radical scavenging activity of some of the isolated compounds was evaluated. Results: Hispidulin-7-O-glucurnoide methyl ester (1), hispidulin-7-O-glucoside (2), cinaroside (3), nepetin-7-O-glucoside (4) pectolinarigenin (5), apigenin (6), luteolin (7) in addition to salicylic acid (8) and β-sitosterol-3-O-glucoside (9) have been isolated. Compounds 1-4 are first report from the genus Lantana, whereas compounds 5, 8 and 9 are first report from this plant. The structures of these compounds were elucidated on the basis of spectral methods, including 2D nuclear magnetic resonance experiments, and confirmed by comparing with the literature data and/or authentic samples. Additionally, some of the isolated flavonoids exhibited free radical scavenging activity. Conclusion: L. montevidensis (Spreng.) Briq. cultivated in Egypt is rich in biologically active ingredients.
Research Authors
Makboul A. Makboul, Ahmed A. Attia, Salwa Farouk Farag, Nesma M. Mohamed, Samir A. Ross
Research Department
Research Journal
Phcog. J., DOI: 10.5530/pj.2014.6.6
Research Member
Research Rank
1
Research Vol
Vol. 6, No. 6
Research Year
2014

Chemical Constituents with Free-Radical-Scavenging Activity from the Leaves of Lantana montevidensis (Spreng.) Briq.

Research Abstract
Background: Seventy percent aqueous methanolic extract of the leaves of Lantana montevidensis exhibited antibacterial, anti-inflammatory, anti-pyretic, antioxidant, and analgesic activities. Previous phytochemical study of the leaves led to the isolation of various flavones, pentacyclic triterpenoids, β-sitosterol and benzoic acid. Materials and Methods: The 70% aqueous methanolic extract of L. montevidensis (Spreng.) Briq. leaves was partitioned between water and n-hexane, CHCl3, EtOAc, and n-BuOH, successively. By using a series of different chromatographic techniques, the CHCl3 and EtOAc extracts afforded nine compounds. The isolated compounds were identified by spectroscopic techniques and by comparison with literature values and/or authentic samples. The free radical scavenging activity of some of the isolated compounds was evaluated. Results: Hispidulin-7-O-glucurnoide methyl ester (1), hispidulin-7-O-glucoside (2), cinaroside (3), nepetin-7-O-glucoside (4) pectolinarigenin (5), apigenin (6), luteolin (7) in addition to salicylic acid (8) and β-sitosterol-3-O-glucoside (9) have been isolated. Compounds 1-4 are first report from the genus Lantana, whereas compounds 5, 8 and 9 are first report from this plant. The structures of these compounds were elucidated on the basis of spectral methods, including 2D nuclear magnetic resonance experiments, and confirmed by comparing with the literature data and/or authentic samples. Additionally, some of the isolated flavonoids exhibited free radical scavenging activity. Conclusion: L. montevidensis (Spreng.) Briq. cultivated in Egypt is rich in biologically active ingredients.
Research Authors
Makboul A. Makboul, Ahmed A. Attia, Salwa Farouk Farag, Nesma M. Mohamed, Samir A. Ross
Research Department
Research Journal
Phcog. J., DOI: 10.5530/pj.2014.6.6
Research Member
Research Rank
1
Research Vol
Vol. 6, No. 6
Research Year
2014

Chemical Constituents with Free-Radical-Scavenging Activity from the Leaves of Lantana montevidensis (Spreng.) Briq.

Research Abstract
Background: Seventy percent aqueous methanolic extract of the leaves of Lantana montevidensis exhibited antibacterial, anti-inflammatory, anti-pyretic, antioxidant, and analgesic activities. Previous phytochemical study of the leaves led to the isolation of various flavones, pentacyclic triterpenoids, β-sitosterol and benzoic acid. Materials and Methods: The 70% aqueous methanolic extract of L. montevidensis (Spreng.) Briq. leaves was partitioned between water and n-hexane, CHCl3, EtOAc, and n-BuOH, successively. By using a series of different chromatographic techniques, the CHCl3 and EtOAc extracts afforded nine compounds. The isolated compounds were identified by spectroscopic techniques and by comparison with literature values and/or authentic samples. The free radical scavenging activity of some of the isolated compounds was evaluated. Results: Hispidulin-7-O-glucurnoide methyl ester (1), hispidulin-7-O-glucoside (2), cinaroside (3), nepetin-7-O-glucoside (4) pectolinarigenin (5), apigenin (6), luteolin (7) in addition to salicylic acid (8) and β-sitosterol-3-O-glucoside (9) have been isolated. Compounds 1-4 are first report from the genus Lantana, whereas compounds 5, 8 and 9 are first report from this plant. The structures of these compounds were elucidated on the basis of spectral methods, including 2D nuclear magnetic resonance experiments, and confirmed by comparing with the literature data and/or authentic samples. Additionally, some of the isolated flavonoids exhibited free radical scavenging activity. Conclusion: L. montevidensis (Spreng.) Briq. cultivated in Egypt is rich in biologically active ingredients.
Research Authors
Makboul A. Makboul, Ahmed A. Attia, Salwa Farouk Farag, Nesma M. Mohamed, Samir A. Ross
Research Department
Research Journal
Phcog. J., DOI: 10.5530/pj.2014.6.6
Research Rank
1
Research Vol
Vol. 6, No. 6
Research Year
2014

The Effect of Azobenzene Cross-Linker Position on the Degree of Helical Peptide Photo-Control

Research Abstract
Photo-switchable α-helical peptides offer a valuable tool to probe protein-biomacromolecule interactions in a spatiotemporally controlled manner. We synthesized a series of 32 residue peptides (AA32 s) with the core structure Ac-W-(E1A2A3A4R5)6-Q-NH2 and introduced the azobenzene based cross-linker BSBCA via reaction with Cys residues spaced at i, i + 7 intervals in different positions along the helix. UV/Vis measurements show that the composition of the photostationary state as well as thermal relaxation rates do not change considerably with changes in cross-linker position. CD analysis shows that photo-control of helix folding/unfolding is most effective when the cross-linker is targeted to the middle of the peptide so long as this segment has a high intrinsic helical propensity. The largest degree of photo-controlled conformational change occurred when a cross-linked central region of high intrinsic helicity was followed on the C-terminal side by a region of lower intrinsic helicity. This indicates the BSBCA cross-linker can act as a nucleation site for N-to-C propagation of a helix. These data help to guide the choice of cross-linking site in larger peptides and proteins where photo-control of conformation is desired.
Research Authors
Ahmed M. Ali, G. Andrew Woolley
Research Journal
Organic & Biomolecular Chemistry
Research Publisher
NULL
Research Rank
1
Research Vol
Vol. 11
Research Website
DOI: 10.1039/c3ob40684a
Research Year
2013

Zeaoxazolinone, a New Antifungal Agent from Zea mays Roots

Research Abstract
A new 7-methoxy-2-benzoxazolinone dimer named zeaoxazolinone (2), together with four known compounds; 9-Z-hexadecenoic acid (1), 6-methoxy-benzoxazolinone (3), gallic acid (4), and -sitosterol-3-O--D-glucopyranoside (5) were isolated from Zea mays L. roots. The structural elucidation of isolatedmetabolites was established on the basis of UV, IR, 1D, 2D NMR, and MS spectral analyses. Compound 2 exhibited a potent antifungal activity against Aspergillus flavus, Fusarium oxysporum, and Candida albicans.
Research Authors
Gamal A. Mohamed, Sabrin R.M. Ibrahim, Mohamed S.A. Abdelkader, Nawal M. Al-Musayeib, Mohamed Ghoneim, Samir A. Ross
Research Department
Research Journal
Med. Chem. Res., DOI: 10.1007/s00044-014-1026-9
Research Rank
1
Research Vol
Vol. 23
Research Year
2014

Dendronephthols A-C, New Sesquiterpenoids from the Red Sea Soft Coral Dendronephthya sp.

Research Abstract
Three new ylangene-type sesquiterpenoids: dendronephthol A (7,13-dihydroxy-3,4-dihydro--ylang-5-one) (1), dendronephthol B (6,7,13-trihydroxy-3,4-dihydro--ylangene) (2), and dendronephthol C (6,7,13-trihydroxy--ylang-5-one) (3), together with two known compounds: dendronesterone A and cholesterol were isolated from the CHCl3 fraction of Red Sea soft coral Dendronephthya sp. (Nephtheidae). The structures of the new compounds were established on the basis of one- and two-dimensional NMR spectroscopic studies (1H, 13C, DEPT, COSY, HSQC, HMBC, and NOESY) as well as MS spectroscopy and by comparison of the spectral data with those of related known compounds. Compounds 1 and 3 showed cytotoxic activity against the murine lymphoma L5187Y cancer cell line with ED50 values of 8.4 and 6.8 µg/mL, respectively.
Research Authors
Ehab S. Elkhayat, Sabrin R.M. Ibrahim, Mostafa A. Fouad, Gamal A. Mohamed
Research Department
Research Journal
Tetrahedron
Research Rank
1
Research Vol
Vol. 70
Research Website
http://dx.doi.org/10.1016/j.tet.2014.03.056
Research Year
2014

Urgineaglyceride A: A New Monoacylglycerol from the Egyptian Drimia maritima Bulbs

Research Abstract
One new compound, (2S)-1-O-(Z)-tetracos-6-enoate glycerol (1) named urgineaglyceride A, along with six known compounds, 3,5,7,3',5'-pentahydroxydihydroflavonol (2), stigmasterol (3), (25S)-5-furostane-3-22-26-triol (4), scillaridin A (5), (2S)-(+)-2-hydroxynaringenin-4'-O--D-glucopyranoside (6) and quercetin-3'-O--Dglucopyranoside (7), were isolated from the EtOAc fraction of Drimia maritima (L.) Stearn bulbs. Their structures were secured based on their IR, UV, 1D and 2D NMR data, in addition to HR-MS data and comparison with the literature data. The isolated compounds were evaluated for their in vitro growth inhibitory activity against A549 non-small cell lung cancer (NSCLC), U373 glioblastoma (GBM) and PC-3 prostate cancer cell lines. Compounds 2 and 3 displayed variable activities against the tested cancer cell lines. Compound 2 was a selective inhibitor of the NSCLC cell line with an IC50 of 2.3 µM, whereas 3 was selective against GBM with IC50 of 0.5 µM and against PC-3 with 2.0 µM.
Research Authors
Gamal A. Mohamed, Sabrin R.M. Ibrahim, Lamiaa A. Shaala, Khalid Z. Alshali, Diaa T.A. Youssef
Research Department
Research Journal
Nat. Prod. Res.
Research Rank
1
Research Vol
Vol. 28, No. 19
Research Website
http://dx.doi.org/10.1080/14786419.2014.927468
Research Year
2014

Theonellamide G, a Potent Antifungal and Cytotoxic Bicyclic Glycopeptide from the Red Sea Marine Sponge Theonella swinhoei

Research Abstract
In our search for bioactive metabolites from marine organisms, we have investigated the polar fraction of the organic extract of the Red Sea sponge Theonella swinhoei. Successive chromatographic separations and final HPLC purification of the potent antifungal fraction afforded a new bicyclic glycopeptide, theonellamide G (1). The structure of the peptide was determined using extensive 1D and 2D NMR and high-resolution mass spectral determinations. The absolute configuration of theonellamide G was determined by chemical degradation and 2D NMR spectroscopy. Theonellamide G showed potent antifungal activity towards wild and amphotericin B-resistant strains of Candida albicans with IC50 of 4.49 and 2.0 μM, respectively. Additionally, it displayed cytotoxic activity against the human colon adenocarcinoma cell line (HCT-16) with IC50 of 6.0 μM. These findings provide further insight into the chemical diversity and biological activities of this class of compounds.
Research Authors
Diaa T.A. Youssef, Lamiaa A. Shaala, Gamal A. Mohamed, Jihan M. Badr, Faida H. Bamanie, Sabrin R.M. Ibrahim
Research Department
Research Journal
Marine Drugs, doi: 10.3390/md12041911
Research Rank
1
Research Vol
Vol. 12
Research Year
2014

New Thiophene and Flavonoid from Tagetes minuta Leaves Growing in Saudi Arabia

Research Abstract
Phytochemical investigation of the methanolic extract of Tagetes minuta L. (Asteraceae) leaves resulted in the isolation and identification of two new compounds: 5-methyl-2,2',5',2'',5'',2''',5''',2''''-quinquethiophene (1) and quercetagetin-6-O-(6-O-caffeoyl--D-glucopyranoside) (9), in addition to seven known compounds: quercetin-3,6-dimethyl ether (2), quercetin-3-methyl ether (3), quercetin (4), axillarin-7-O--D-glucopyranoside (5), quercetagetin-3,7-dimethoxy-6-O--D-glucopyranoside (6), quercetagetin-7-methoxy-6-O--D-glucopyranoside (7), and quercetagetin-6-O--D-glucopyranoside (8). The compounds were identified by UV, IR, 1D, 2D NMR, and HRESIMS spectral data. They showed significant antioxidant activity, comparable with that of propyl gallate. Compounds 8 and 3 showed weak to moderate antileishmanial and antimalarial activities, with IC50 values of 31.0 μg/mL and 4.37 μg/mL, respectively.
Research Authors
Nawal M. Al-Musayeib, Gamal A. Mohamed, Sabrin R.M. Ibrahim, Samir A. Ross
Research Department
Research Journal
Molecules, doi: 10.3390/molecules19032819
Research Rank
1
Research Vol
Vol. 19
Research Year
2014
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