Publications by authors named "Seif-Eldin N Ayyad"

30 Publications

  • Page 1 of 1

Polymorphisms of interleukin 4 and interleukin 4 receptor genes and bronchial asthma risk among Egyptian children.

Clin Biochem 2021 Jul 20;93:66-72. Epub 2021 Apr 20.

Chemistry Department, Faculty of Science, Damietta University, Damietta, Egypt.

Background: Interleukin 4 (IL4) is a key cytokine that regulates the inflammatory cascade in bronchial asthma. We investigated the association between the IL4 and IL4R polymorphisms and the susceptibility for bronchial asthma among Egyptian children.

Methods: IL4 VNTR and IL4R c.1902 A>G p.(Q576R) polymorphisms were investigated among 100 children with bronchial asthma and 100 healthy controls using PCR method. Serum levels of IL4 and immunoglobulin E (IgE) were assessed by ELISA.

Results: The frequencies of (A1A2 + A2A2) genotypes and A2-allele of the IL4 VNTR variant were significantly higher among asthmatic patients than controls (p = 0.01, OR = 2.34, 95% CI = 1.24-4.44; p = 0.01, OR = 2.27, 95% CI = 1.29-3.99, respectively). The frequencies of (AG + GG) genotypes and G-allele of the IL4R (A1902G) variant were significantly higher among asthmatic patients than controls (p = 0.003, OR = 2.52, 95% CI = 1.39-4.58; p = 0.002, OR = 2.25, 95% CI = 1.35-3.76, respectively). There was a significant association between (A1A2 + A2A2) genotypes of the IL4 VNTR variant and high serum IL4 level among asthmatic patients (p < 0.001). The (AG + GG) genotypes of the IL4R (A1902G) variant were significantly associated with exposure to triggers, atopic dermatitis and higher serum IgE level in asthmatic patients (p = 0.02, 0.04 and 0.01, respectively).

Conclusion: IL4 VNTR and IL4R (A1902G) polymorphisms could be associated with higher risks of bronchial asthma among Egyptian children.
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http://dx.doi.org/10.1016/j.clinbiochem.2021.04.006DOI Listing
July 2021

Gene Expression Profiling to Delineate the Anticancer Potential of a New Alkaloid Isopicrinine From .

Integr Cancer Ther 2020 Jan-Dec;19:1534735420920711

King Abdulaziz University, Jeddah, Saudi Arabia.

has been used as a folkloric medicinal herb for treating various diseases such as diabetes, inflammatory disorders, and sore throat. Several studies have revealed the potential of this plant as an important source of phytochemicals with anticancer properties. The present study was designed to isolate a novel anticancer compound from and elucidate its mechanism of action using genomics approach. leaves extract was prepared, and several alkaloids were purified and characterized. These alkaloids were screened for their anticancer potential. One of the alkaloids, termed as isopicrinine, showed efficient cytotoxicity against MCF7 breast cancer cell line and was selected for further analysis. RNA-Seq transcription profiling was conducted to identify the affected genes and cellular pathways in MCF7 cells after treatment with isopicrinine alkaloid. In vitro studies revealed that newly identified isopicrinine alkaloid possess efficient anticancer activity. Exposure of MCF7 cells with isopicrinine affected the expression of various genes involved in p53 signaling pathway. One of the crucial proapoptotic genes, significantly upregulated in MCF7 after exposure to alkaloid, was (p53 upregulated modulator of apoptosis), which is involved in p53-dependent and -independent apoptosis. Moreover, exposure of sublethal dose of isopicrinine alkaloid in breast cancer cell line led to the downregulation of survivin, which is involved in negative regulation of apoptosis. Besides, several genes involved in mitosis and cell proliferation were significantly downregulated. In this article, we report the determination of a new alkaloid isopicrinine from the aerial parts of with anticancer property. This compound has the potential to be developed as a drug for curing cancer.
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http://dx.doi.org/10.1177/1534735420920711DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7262827PMC
July 2021

Cytotoxic Metabolites from Display Antiproliferative Activity by Inducing Apoptosis in HCT-116 Cells.

Pharmacogn Mag 2017 Jan 7;13(Suppl 1):S37-S40. Epub 2017 Apr 7.

Department of Pharmacology and Toxicology, Faculty of Pharmacy, King Abdulaziz University, Jeddah, Saudi Arabia.

Objectives: To evaluate the antiproliferative effect of the isolated metabolites from .

Methods: Different chromatographic methods have been done on the organic extract of the marine sponge aiming at isolating the bioactive metabolites. The cytotoxicity of the isolated compounds has been evaluated against the human colorectal cancer cell line; HCT-116, employing SRB assay. The flow cytometry assay was applied to measure the cell cycle analysis.

Results: Six metabolites (1-6) were obtained. The compounds 4-6 exhibited IC values (μM ± SD) of 95.80± 1.34, 14.8 ± 2.33, and 19.8 ± 3.78, respectively. Cell cycle distribution analysis revealed that sipholenol A (5) and sipholenol L (6) induced G2/M and S phase arrest with concomitant increase in the pre-G cell population. Furthermore, 5 and 6 increased the nuclear expression of the pro-apoptotic protein-cleaved caspase-3 that effectively drives cellular apoptosis via caspase-3-dependent pathway.

Conclusions: The antiproliferative activity of 5 and 6 can be recognized, at least partly, due to their ability to induce cellular apoptosis.

Summary: Several metabolites were isolated from the marine sponge Callyspongia siphonella. Sipholenol A and sipholenol L exhibited effective cytotoxicity against HCT-116 cells. The observed cytotoxicity involves induction of cellular apoptosis. A549 (human lung carcinoma), Caco-2 (Human ColonCarcinoma), CHCl3 (Chloroform), HCT 116 (Human Colon Carcinoma), HepG2 (Liver Hepatocellular Carcinoma), HT-29 (Human Colorectal Adenocarcinoma), MCF-7 (Michigan Cancer Foundation-7; Human Breast Adenocarcinoma), MeOH (Methanol), NMR Nuclear Magnetic Resonance), PBS (Phosphate Buffered Saline), PC-3 (Human Prostate Cancer), PTLC (Preparative Thin Layer Chromatography), RPMI-1640 (Roswell Park Memorial Institute medium), TLC (ThinLayer Chromatography).
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http://dx.doi.org/10.4103/0973-1296.203970DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5407114PMC
January 2017

Isolation, antimicrobial and antitumor activities of a new polyhydroxysteroid and a new diterpenoid from the soft coral Xenia umbellata.

Z Naturforsch C J Biosci 2017 Jan;72(1-2):27-34

Department of Chemistry, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah 21589, Saudi Arabia.

A new C-30 steroid, 3β-,5α-,6β-,11α-,20β-pentahydroxygorgosterol (1), and a new diterpenoid, xeniumbellal (2), along with three known aromadendrane-type sesquiterpenes, aromadendrene (3), palustrol (4) and viridiflorol (5), were isolated from the soft coral Xenia umbellata. Chemical structures were determined by analyzing their NMR and MS data. The antimicrobial and antitumor activities of the isolated compounds were examined. Both 1 and 2 showed moderate antibacterial activities, especially against the multidrug-resistant Acinetobacter baumannii (MIC 0.22 and 0.28 mM, respectively); while 2 showed antitumor activity against a lymphoma cell line with LD50 0.57 mM and was nontoxic to Artemia salina at all tested concentrations up to about 4 mM.
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http://dx.doi.org/10.1515/znc-2015-0228DOI Listing
January 2017

Antiproliferative effects of triterpenoidal derivatives, obtained from the marine sponge Siphonochalina sp., on human hepatic and colorectal cancer cells.

Z Naturforsch C J Biosci 2016 ;71(1-2):29-35

Three triterpenoidal derivatives [Sipholenol A (1), sipholenol L (2) and sipholenone A (3)] were isolated from the Red Sea sponge Siphonochalina sp. The structures were determined based on spectroscopic measurements (NMR, UV, IR and MS). The isolated compounds were evaluated for their cytotoxic activity against three cancer cell lines; HepG2, Caco-2 and HT-29. Moreover, the effects of these metabolites on cell cycle progression as well as cell cycle regulating proteins were assessed. Compounds 1, 2 and 3 showed moderate activity against HepG2 cells with IC(50) values of 17.18 ± 1.18, 24.01 ± 0.59 and 35.06 ± 1.10 μM, respectively. Compounds 1 and 2 exerted a considerable antiproliferative effect with IC(50) values of 4.80 ± 0.18 and 26.64 ± 0.30 μM, respectively, against Caco-2 cells. Finally, 1 and 2 exhibited antiproliferative activity against colorectal cancer cells (HT-29) with IC(50) values of 24.65 ± 0.80 and 4.48 ± 0.1 μM, respectively. Cell cycle analysis indicated that these compounds induced cell cycle arrest particularly in G0/G1 and S phases. Furthermore, the triterpenoids increased the expression of cyclin-B1, cyclin-D1 and cleaved caspase-3, as determined by immunofluorescence, indicating an important role of apoptosis in cell death induced by these compounds.
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http://dx.doi.org/10.1515/znc-2015-0160DOI Listing
August 2016

New cytotoxic cyclic peroxide acids from sp. marine sponge.

ARKIVOC 2015;2015(5):164-175. Epub 2015 Apr 5.

Department of Chemistry, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah 21589, Saudi Arabia; Department of Chemistry, Faculty of Science, Damietta University, Damietta, Egypt.

Bioassay-guided fractionation of the extract of Jamaican marine sponge sp. followed by preparative TLC and HPLC yielded several known methyl ester cyclic peroxides (), known plakortides (), known bicyclic lactone () and new cyclic peroxide acids (). The chemical structures were elucidated by extensive interpretation of their spectroscopic data. These natural products showed remarkable in vitro cytotoxicity against several cancer cell lines.
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http://dx.doi.org/10.3998/ark.5550190.p008.948DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4732738PMC
April 2015

Cytotoxic scalarane-type sesterterpenes from the Saudi Red Sea sponge Hyrtios erectus.

J Asian Nat Prod Res 2016 Jun 2;18(6):611-7. Epub 2015 Dec 2.

b Faculty of Science, Department Chemistry , King Abdulaziz University , Jeddah 21589 , Saudi Arabia.

The CHCl3/MeOH extract of the marine sponge Hyrtios erectus showed cytotoxicity against three cancer cell lines HepG2, A549, and PC-3 with IC50 0.055, 0.044, and 0.023 μg/ml, respectively. The CH2Cl2 soluble fraction afforded three scalarane sesterterpenes (1-3) along with a cholestane derivative (4) and an indole alkaloid (5). Chemical structures were established by spectroscopic techniques and comparison with data reported in the literature. Scalarinol (1) was found as a new metabolite, while heteronemin (2) and 12-O-deacetyl-19-deoxyscalarin (3) are known compounds. 1-3 exhibited cytotoxic activity against the cancer cell lines with IC50 values ranging from 14 to 230 μM. The molecular affinity to the DNA was employed as marker to examine the proposed mechanism of cytotoxic activities. Compound 2, with IC50 28 μg/ml, displayed the highest affinity to the DNA.
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http://dx.doi.org/10.1080/10286020.2015.1115019DOI Listing
June 2016

Two new polyacetylene derivatives from the Red Sea sponge Xestospongia sp.

Z Naturforsch C J Biosci 2015 Nov;70(11-12):297-303

Two new polyacetylenes (1 and 2), along with two known C-30 steroids (3 and 4) were identified from the Red Sea sponge, Xestospongia sp. The chemical structures were determined based on extensive spectroscopic measurements 1D (1H, 13C and DEPT) and 2D (COSY, HSQC and HMBC) NMR, UV, IR and MS. The new compounds 1 and 2 were evaluated for their antimicrobial and antitumor activities. 1 and 2 were active against multidrug- resistant bacteria with MICs ranged from 2.2 to 4.5 μM. No toxicity was recorded for the two tested compounds up to 5 μM using Artemia salina as a test organism. Compound 2 showed excellent antifungal activity against some pathogenic fungi such as Aspergillus niger and Candida albicans (MIC 2.2-2.5 μM) and antitumor activity against both Ehrlich ascites carcinoma and lymphocytic leukemia (LD50 5.0 μM).
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http://dx.doi.org/10.1515/znc-2015-5015DOI Listing
November 2015

A review of steroids from Sarcophyton species.

Nat Prod Res 2016 24;30(8):869-79. Epub 2015 Aug 24.

b Faculty of Marine Science, Department of Marine Chemistry , King Abdul Aziz University , Jeddah , Saudi Arabia.

This review reports the structural diversity of steroids from Sarcophyton species based on literature from the beginning of marine steroid research until now. There are 65 compounds studied from eight species. Most of them are polyhydroxy-type steroids of C-27-C-31 carbon skeleton. Their biological activities are highly diverse ranging from cytotoxic, antibacterial, antifungal, antiviral, anti-inflammatory, antidiabetic to antiosteoporosis properties.
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http://dx.doi.org/10.1080/14786419.2015.1079187DOI Listing
November 2016

The role of new eudesmane-type sesquiterpenoid and known eudesmane derivatives from the red alga Laurencia obtusa as potential antifungal-antitumour agents.

Nat Prod Res 2016 16;30(10):1150-5. Epub 2015 Jul 16.

e Department of Pharmacognosy , Faculty of Pharmacy, Mansoura University , Mansoura 35516 , Egypt.

A new eudesmane sesquiterpenoid, eudesma-4(15),7-diene-5,11-diol (1) along with the known trinor-sesquiterene, teuhetenone (2), and a seco-eudesmane sesquiterpene, chabrolidione B (3), have been isolated from the Red Sea red alga Laurencia obtusa. The chemical structures were elucidated on the basis of extensive spectroscopic analysis. The antifungal and cytotoxic activities of the isolated metabolites were tested against several fungi, yeast and human mammary carcinoma cell line (MCF-7). Compounds 1 and 3 showed a much better activity [minimum inhibitory concentration (MIC): 2.9 μM] than that of amphotericin B (MIC: 4.6 μM). Interestingly, compound 2, the least active antifungal compound, retained the high anticancer activity against MCF-7 (22 μM) in comparison with cisplatin (59 μM), which was determined by employing lactate dehydrogenase assay. Compounds 1-3 are recorded here for the first time from algal flora. The chemotaxonomic importance of the isolated metabolites was discussed.
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http://dx.doi.org/10.1080/14786419.2015.1046378DOI Listing
October 2016

Differential cytotoxic activity of the petroleum ether extract and its furanosesquiterpenoid constituents from Commiphora molmol resin.

Z Naturforsch C J Biosci 2015 ;70(3-4):87-92

This study revealed a differential cytotoxic activity of the petroleum ether extract (IC₅₀ =5 μg/mL) of the resinous exudates of Commiphora molmol against two mouse cell lines KA31T and NIH3T3 (untransformed and transformed mouse fibroblasts, respectively). Four new compounds (1-4) and five known compounds (5-9) were isolated from the petroleum ether extract. The identity of these new compounds was determined as γ-elemane lactone (1), 5-αH,8-βH-eudesma-1,3,7(11)-trien-8,12-olide (2), 2-hydroxy-11,12-dihydrofuranodiene (3), and 2-hydroxyfuranodiene (4). 1 and 2 displayed the highest cytotoxic activity against NIH3T3 cells. 7 and 9 exhibited moderate cytotoxic activity against KA31T cells. Compounds 3-6 showed weak cytotoxic activities against both cell lines. These results may explain the high efficacy of the petroleum ether fraction in several myrrh-derived pharmaceutical preparations.
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http://dx.doi.org/10.1515/znc-2014-4191DOI Listing
October 2015

New cytotoxic isoprenoid derivatives from the Red Sea soft coral Sarcophyton glaucum.

Nat Prod Res 2015 30;29(1):24-30. Epub 2014 Aug 30.

a Department of Natural Products and Alternative Medicine , Faculty of Pharmacy, King Abdulaziz University , P.O. Box 80260, Jeddah 21589 , Saudi Arabia.

Chemical investigation of the soft coral Sarcophyton glaucum collected from the Red Sea led to isolation of 11 isoprenoidal metabolites (1-11). A new sesquiterpenoid, 6-oxo-germacra-4(15),8,11-triene (1), a new natural cembranoid, sarcophinediol, along with two known sesquiterpenoids (2 and 3) and seven known cembranoids (5-11) was obtained. The structures of the compounds were established based on their NMR, MS, IR and UV spectral data. All compounds were evaluated for their cytotoxicity employing three cancer cell lines (HepG2, MCF-7 and HCT116). Compounds 4 and 6 showed significant cytotoxicity towards HepG2 with IC50 values of 18.8 ± 0.07 and 19.9 ± 0.02 μM; respectively. Compounds 5-7 exhibited potent cytotoxicity against MCF-7 cells with IC50 values of 9.9 ± 0.03, 2.4 ± 0.04 and 3.2 ± 0.02 μM, respectively. Compounds 1, 4 and 5 showed significant activities towards HCT116 cells with IC50 values of 29.4 ± 0.03, 19.4 ± 0.02 and 25.8 ± 0.03 μM, respectively.
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http://dx.doi.org/10.1080/14786419.2014.952637DOI Listing
March 2015

Cytotoxic neviotane triterpene-type from the red sea sponge Siphonochalina siphonella.

Pharmacogn Mag 2014 Apr;10(Suppl 2):S334-41

Department of Chemistry, Dammietta University, New Dammietta, Egypt.

Background: Siphonochalina siphonella is a marine sponge collected from saudi Red Sea water and scare study from this region.

Objective: To isolate the anticancer triterpenes with potent cytotoxicity from marine sponge, Siphonochalina siphonella and state the mode of action in cancer cell lines.

Materials And Methods: The sponge material was collected, extracted with organic solvent, and fractionated on different adsorbents. The structure of the pure metabolites were elucidated employing different spectroscopic techniques including 1D ((1)H and (13)C) and 2D (COSY, HMQC and HMBC) NMR, and MS spectroscopy.

Results: A new Neviotine-C (1) was obtained, along with four known metabolites (2-5). All compounds, except 5, were tested towards MCF-7, PC-3 and A549 and showed effects with IC50 in range 7.9-87 μM, whilst, 3 showed potent anti-proliferative activity against PC-3 and A549 with IC50 = 7.9 ± 0.120 and 8.9 ± 0.010 μM, respectively.

Conclusion: Compounds (1-4) showed significant cytotoxic activities, while 3 showed potent effect. The antiproliferative of 3 was attributed to significant S-phase cell cycle arrest.
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http://dx.doi.org/10.4103/0973-1296.133292DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4078349PMC
April 2014

Cytotoxic polyacetylenes from the Red Sea sponge Siphonochalina siphonella.

Z Naturforsch C J Biosci 2014 Mar-Apr;69(3-4):117-23

Two new polyacetylenes, callyspongenol-D (1) and callyspongendiol (2), the known polyacetylene dehydrosiphonochalynol (3), and the known triterpenoid sipholenol-A (4) were isolated from the Red Sea sponge Siphonochalina siphonella. Their chemical structures were elucidated on the basis of spectroscopic analyses. The cytotoxicity of the isolated compounds towards the human mammary carcinoma cell line MCF-7 was determined by the lactate dehydrogenase (LDH) assay, and compounds 4 and 1 were found to be the most toxic of the four, with IC50 values of 8.8 and 11.7 microM, respectively.
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http://dx.doi.org/10.5560/znc.2013-0088DOI Listing
June 2014

Three new cembranoid-type diterpenes from Red Sea soft coral Sarcophyton glaucum: isolation and antiproliferative activity against HepG2 cells.

Eur J Med Chem 2014 Jun 5;81:314-22. Epub 2014 May 5.

Department of Pharmacognosy, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt.

Three new cembranoids: sarcophytolol (1), sarcophytolide B (2), and sarcophytolide C (3), along with three known metabolites: 10(14)aromadendrene (4), deoxosarcophine (5), and sarcophine (6) were obtained from the soft bodied coral Sarcophyton glaucum. The structures were determined based on spectroscopic measurements (NMR, UV, IR and MS). Compounds 1, 3, and 4 had similar significant cytotoxic effects towards HepG2 (Human hepatocellular liver carcinoma; IC50 = 20 μM). 2 and 3 showed activity against MCF-7 (Human breast adenocarcinoma; IC50 25 ± 0.0164 and 29 ± 0.030 μM, respectively). Finally, 4 showed potent activity towards PC-3 (Prostate cancer; IC50 9.3 ± 0.164 μM). The antiproliferative activity of 1, 3 and 4, can be attributed, at least partly, to their ability to induce cellular apoptosis.
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http://dx.doi.org/10.1016/j.ejmech.2014.05.016DOI Listing
June 2014

Cytotoxic effects of three new metabolites from Red Sea marine sponge, Petrosia sp.

Environ Toxicol Pharmacol 2014 May 15;37(3):928-35. Epub 2014 Mar 15.

Department of Marine Chemistry, Faculty of Marine Sciences, King Abdulaziz University, PO. Box 80207, Jeddah 21589, Saudi Arabia.

Marine sponges represent an affluent source of biogenetically unprecedented array of biologically active compounds. This study revealed the isolation of ten compounds from marine sponge of Petrosia sp. Their chemical structures were determined by using 1D and 2D NMR, UV, IR and MS measurements. A polyoxygenated steroid (3β,7β,9α-trihydroxycholest-5-en (1), a purine-derivative (3,7-dimethyl-2-(methylamino)-3H-purin-6(7H)-one (2) and a sphingolipid (N-((3S,E)-1,3-dihydroxytetracos-4-en-2-yl)stearamide (3) proved to be new compounds. Meanwhile, seven known compounds; (4-10) were also identified. The cytotoxicity of the total extract and the isolated compounds were subjected to cytotoxicity evaluation employing two cancer cell lines; HepG2 and MCF-7. All tested compounds exhibited cytotoxic effect on both cancer cell lines with IC(50) in range of 20-500 μM. The proposed mechanism of cytotoxic activities was examined through its molecular affinity to the DNA. Compound 5 showed the highest affinity to the DNA with IC(50) 30 μg/mL.
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http://dx.doi.org/10.1016/j.etap.2014.03.005DOI Listing
May 2014

Selective cytotoxic effects on human breast carcinoma of new methoxylated flavonoids from Euryops arabicus grown in Saudi Arabia.

Eur J Med Chem 2013 Aug 5;66:204-10. Epub 2013 Jun 5.

Department of Marine Chemistry, Faculty of Marine Sciences, King Abdulaziz University, PO Box 80207, Jeddah 21589, Saudi Arabia.

The chloroform-methanol extract of Euryops arabicus, collected from Saudi provenance, yielded a new kaurane diterpene (1) and seven methoxylated flavones (2-8), two of which are new (2 and 3). Structures of the compounds were elucidated through interpretation of spectral data of NMR, MS and comparison with literature values. All compounds were evaluated for their anti-tumor activities, employing four different cancer cell lines (WI-38, VERO, HepG2 and MCF-7), ABTS free radical scavenging and immunemodulatory effects. All metabolites had considerable antioxidant and immunestimulatory effects. All compounds showed anticancer activity with IC₅₀ in range 10-125 μM, whilst 2 and 6 showed significant anti-proliferative activity against HepG2 (IC₅₀ = 20 and 15 μM) and MCF-7 (IC₅₀ = 15 and 10 μM), respectively. This effect was attributed to significant S-phase cell cycle arrest.
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http://dx.doi.org/10.1016/j.ejmech.2013.05.025DOI Listing
August 2013

New diarylheptanoids and a hydroxylated ottelione from Ottelia alismoides.

Nat Prod Commun 2013 Mar;8(3):351-8

Department of Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, USA.

Ten new diarylheptanoids (2, 3, 4, 5a-d, 6, 7, and 8) have been isolated from an extract of Ottelia alismoides. The structures of these previously unknown metabolites were determined by NMR spectroscopic analysis. A previously unknown, hydroxylated analog of the known otteliones A and B (1a and 1b)--namely, 3a-hydroxyottelione (13)--was also isolated. The 1H NMR analysis of the Mosher esters of alcohols derived from otteliones A and B (S-17/R-17 and S-20/R-20) are also reported.
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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4726472PMC
March 2013

A new cytotoxic brominated acetylenic hydrocarbon from the marine sponge Haliclona sp. with a selective effect against human breast cancer.

Z Naturforsch C J Biosci 2013 Jan-Feb;68(1-2):70-5

Department of Marine Chemistry, Faculty of Marine Sciences, King Abdulaziz University, PO Box 80207, Jeddah 21589, Saudi Arabia.

Three acetylenic brominated derivatives were isolated from a Red Sea sponge, Haliclona sp. One of them, 18-bromooctadeca-9(E),17(E)-dien-7,15-diynoic acid (3), is a known metabolite, and the other two are new compounds, (1E,5E,12E,19E)-1,22-dibromodocosa-1,5,12,19-tetraen-3,14,21-triyne (1) and methyl 18-bromooctadeca-9(E),17(E)-dien-7,15-diynoate (2) which was isolated for the first time as a natural metabolite. Structures of all compounds were determined based on extensive spectroscopic measurements [1D (1H, 13C and DEPT) and 2D (HSQC, HMBC and NOESY) NMR, MS, UV, and IR]. All compounds, except 3, were evaluated for their cytotoxicity employing four cancer cell lines, i.e. MCF-7 (human breast cancer), HepG2 (human hepatocellular carcinoma), WI-38 (skin carcinoma), and Vero (African green monkey kidney). Compounds 1 and 2 had potent selective antitumour activity towards MCF-7 cells with IC50 values of 32.5 and 50.8 microM, respectively.
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June 2013

Laurene-type sesquiterpenes from the Red Sea red alga Laurencia obtusa as potential antitumor-antimicrobial agents.

Eur J Med Chem 2012 Sep 7;55:462-6. Epub 2012 Jul 7.

Department of Marine Chemistry, Faculty of Marine Sciences, King Abdulaziz University, PO. Box 80207, Jeddah 21589, Saudi Arabia.

Three new laurene-type sesquiterpenes, 12-hydroxy isolaurene (1), 8,11-dihydro-12-hydroxy isolaurene (2) and isolauraldehyde (3) were isolated from the organic extract of the red alga Laurencia obtusa. The chemical structures of isolates were determined by interpretation of their spectral data 1D and 2D NMR, UV, IR and MS. The newly isolated compounds were tested for their antimicrobial and antitumor activities. Compounds (1-3) exhibited potent activity against the gram-positive Bacillus subtilis and Staphylococcus aureus, where 3 proved to be the most active (MIC 35 and 27 μg/mL, respectively). Moreover, compound 3 exhibited a significant activity against Candida albicans (MIC of 70 μg/mL) and revealed to have very promising activity in an in vitro model of Ehrlich ascites Carcinoma.
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http://dx.doi.org/10.1016/j.ejmech.2012.06.060DOI Listing
September 2012

New antifungal cholestane and aldehyde derivatives from the red alga Laurencia papillosa.

Nat Prod Commun 2011 Dec;6(12):1821-4

Department of Marine Chemistry, Faculty of Marine Sciences, King AbdulAziz University, P.O. Box 80207, Jeddah 21589, Saudi Arabia.

The chloroform/methanol extract of the red alga, Laurencia papillosa, collected from the Red Sea in Saudi Arabia, was found to contain two cholestane derivatives: 3alpha, 6alpha-dihydroxy-5beta-cholestan-12-one (1) and the known, 6beta-hydroxycholest-4-en-3-one (2), which was isolated separately in a pure form for the first time. In addition to these compounds, a new aldehyde derivative, (E)-2-{(E) tridec-2-en-2-yl} heptadec-2-enal (3), was isolated. The structures of all compounds were established based on extensive spectroscopic (1D and 2D NMR, UV, IR) and mass spectrometric studies. All compounds, except 2, were tested for their antifungal activity. Significant activities were associated with 1 and 3 against Candida albicans, Aspergillus fumigatus, and A. flavus.
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December 2011

In vitro and in vivo study of cucurbitacins-type triterpene glucoside from Citrullus colocynthis growing in Saudi Arabia against hepatocellular carcinoma.

Environ Toxicol Pharmacol 2012 Mar 16;33(2):245-51. Epub 2011 Dec 16.

Department of Chemistry, Faculty of Science, King Abdulaziz University, PO Box 80203, Jeddah 21589, Saudi Arabia.

Chromatographic investigation of fruits obtained from Citrullus colocynthis, growing in Saudi Arabia, led to isolation of two compounds; Cucurbitacin E glucoside (Cu E, 1), and Cucurbitacin I glucoside (Cu I, 2). The chemical structures of 1 and 2, were elucidated by spectroscopic analyses include; 1D ((1)H and (13)C) and 2D (COSY, HMQC and HMBC) NMR and ESI-MS spectroscopy. The in vitro cytotoxic activity against hepatoma cell line (HepG2) and mice-bearing tumor of Ehrlich's ascites carcinoma (EAC) of the compounds were estimated. Both compounds had potent inhibitory activity on HepG2 with IC(50) 3.5 and 2.8 nmol/mL, respectively. In addition to these activities, the in vivo study employing EAC, showed the capability of both compounds to prolong the survival time, life span and normalize the biochemical parameters of the infected mice with EAC.
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http://dx.doi.org/10.1016/j.etap.2011.12.010DOI Listing
March 2012

Cucurbitacins-type triterpene with potent activity on mouse embryonic fibroblast from Cucumis prophetarum, cucurbitaceae.

Pharmacognosy Res 2011 Jul;3(3):189-93

Department of Chemistry, Faculty of Science, King Abdulaziz University, P. O. Box 80203, Jeddah 21589, Saud Arabia.

Background: Higher plants are considered as a well-known source of the potent anticancer metabolites with diversity of chemical structures. For instance, taxol is an amazing diterpene alkaloid had been lunched since 1990.

Objective: To isolate the major compounds from the fruit extract of Cucumis prophetarum, Cucurbitaceae, which are mainly responsible for the bioactivities as anticancer.

Materials And Methods: Plant material was shady air dried, extracted with equal volume of chloroform/methanol, and fractionated with different adsorbents. The structures of obtained pure compounds were elucidated with different spectroscopic techniques employing 1D ((1)H and (13)C) and 2D (COSY, HMQC and HMBC) NMR (Nuclear Magnetic Resonance Spectrometry) and ESI-MS (Eelectrospray Ionization Mass Spectrometry) spectroscopy. The pure isolates were tested towards human cancer cell lines, mouse embryonic fibroblast (NIH3T3) and virally transformed form (KA3IT).

Results: Two cucurbitacins derivatives, dihydocucurbitacin B (1) and cucurbitacin B (2), had been obtained. Compounds 1 and 2 showed (showed potent inhibitory activities toward NIH3T3 and KA31T with IC(50) 0.2, 0.15, 2.5 and 2.0 μg/ml, respectively.

Conclusion: The naturally cucurbitacin derivatives (dihydocucurbitacin B and cucurbitacin B) showed potent activities towards NIH3T3 and KA31T, could be considered as a lead of discovering a new anticancer natural drug.
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http://dx.doi.org/10.4103/0974-8490.85006DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3193620PMC
July 2011

Antioxidant, cytotoxic, antitumor, and protective DNA damage metabolites from the red sea brown alga Sargassum sp.

Pharmacognosy Res 2011 Jul;3(3):160-5

Department of Chemistry, Faculty of Science, King Abdul Aziz University, P. O. 80203, Jeddah 21589, KSA.

Background: Macroalgae can be viewed as a potential antioxidant and anti-inflammatory sources owing to their capability of producing compounds for its protection from environmental factors such as heat, pollution, stress, oxygen concentration, and UV radiations.

Objective: To isolate major compounds which are mainly responsible for the pharmacological activity of brown alga under investigation, Sargassum sp.

Materials And Methods: Algal material was air dried, extracted with a mixture of organic solvents, and fractionated with different adsorbents. The structures of obtained pure compounds were elucidated with different spectroscopic techniques, and two pure materials were tested for protection of DNA from damage, antioxidant, antitumor, and cytotoxicity.

Results: Four pure compounds were obtained, of which fucosterol (1) and fucoxanthin (4) were tested; it was found that fucoxanthin has strong antioxidant and cytotoxicity against breast cancer (MCF-7) with IC(50) = 11.5 μg/ml.

Conclusion: The naturally highly conjugated safe compound fucoxanthin could be used as antioxidant and as an antitumor compound.
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http://dx.doi.org/10.4103/0974-8490.85000DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3193615PMC
July 2011

Antigenotoxic ketosteroid from the red algae Jania adhaerens.

Nat Prod Res 2012 22;26(9):785-91. Epub 2011 Aug 22.

Department of Marine Chemistry, Faculty of Marine Sciences, King Abdulaziz University, PO Box 80207, Jeddah 21589, Saudi Arabia.

A new ketosteroid, 6β,16β-dihydroxycholest-4-en-3-one (1), in addition to the known 6β-hydroxycholest-4-en-3-one (2), 6β-hydroxycholest-4,22-dien-3-one (3) and 16β-hydroxy-5α-cholestan-3,6-dione (4), was isolated from the red alga Jania adhaerens. The structures were assigned on the basis of (1)H- and (13)C-NMR experiments. The new compound (1) was evaluated for its genotoxic and cytotoxic activities and found to possess protective antigenotoxicity in human peripheral blood cells.
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http://dx.doi.org/10.1080/14786419.2010.548336DOI Listing
August 2012

Cytotoxic and protective DNA damage of three new diterpenoids from the brown alga Dictoyota dichotoma.

Eur J Med Chem 2011 Jan 4;46(1):175-82. Epub 2010 Nov 4.

Department of Chemistry, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah 21589, Saudi Arabia.

Three new diterpenes Amijiol acetate (3), dolabellane, Dolabellatrienol (4), and dolastane, Amijiol-7, 10-diacetate (9) were isolated together with the previously described Pachydictyol A (1), Isopachydictyol A (2), 8β-hydroxypachydictyol A (5), Amijiol (6), Isodictyohemiacetal (7) and Dictyol C (8) from the Red Sea brown alga Dictyota dichotoma var. implexa. The structures and relative stereochemistry of the new diterpenoids were proposed on the basis of their spectral data. Compounds 3 and 9 have potent activity against DNA damage, cytotoxicity against WI-38, HepG2, and MCF-7 cell lines, and antioxidant using ABTS and erythrocytes hemolysis.
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http://dx.doi.org/10.1016/j.ejmech.2010.10.033DOI Listing
January 2011

Isolation and structure determination of the biologically active sphingolipids from marine sponge Haliclona species.

Nat Prod Res 2009 ;23(1):44-50

Faculty of Science, Department of Chemistry, King Abdulaziz University, Jeddah, Saudi Arabia.

In a continuation to our study on the marine sponge Haliclona species we have isolated three new cytotoxic components of sphingolipids (1-3). Methanolysis of the sphingolipid 1a-d in methanol produces fatty acid methyl ester. GC/MS was used to determine the length. The structure of each isolated compound has been determined on the basis of spectroscopic data and chemical evidence.
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http://dx.doi.org/10.1080/14786410701768246DOI Listing
February 2009

The structural determination of a new steroidal metabolite from the brown alga Sargassum asperifolium.

Z Naturforsch C J Biosci 2003 May-Jun;58(5-6):333-6

Department of Chemistry, Dammietta Faculty of Science, Mansoura University, New Dammietta P. O. 34517, Egypt.

An investigation of the natural products chemistry of the brown alga Sargassum asperifolium from the red sea yielded a new steroidal metabolite, 24-vinyl cholest-4-ene-24-ol-3-one, saringosterone (3), a known steroidal metabolite, 24-vinyl cholest-5-ene-3b,24-diol, saringosterol (4), and known diterpene with a hydroazulene skeleton, dictyone (1). The identification of the isolated metabolites was established mainly by spectral methods and chemical transformation of the dictyone (1) to its acetate (2).
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http://dx.doi.org/10.1515/znc-2003-5-607DOI Listing
October 2003

Cytotoxic hydroazulene diterpenes from the brown alga Cystoseira myrica.

Z Naturforsch C J Biosci 2003 Jan-Feb;58(1-2):33-8

Department of Chemistry, Faculty of Science, Mansoura University, New Damietta, Egypt.

Cytotoxicity-guided fractionation of the alcohol extract of the brown alga, Cystoseira myrica, afforded four new cytotoxic hydroazulene diterpenes, dictyone acetate (2), dictyol F monoacetate (4), isodictytriol monoacetate (6), and cystoseirol monoacetate (8), together with two known cytotoxic hydroazulene diterpenes, pachydictyol A (1) and dictyone (3). The constitution of each isolated compound has been determined on the basis of spectroscopic and chemical evidence.
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http://dx.doi.org/10.1515/znc-2003-1-205DOI Listing
April 2003

Toward computing relative configurations: 16-epi-latrunculin B, a new stereoisomer of the actin polymerization inhibitor latrunculin B.

J Am Chem Soc 2002 Jun;124(25):7405-10

Department of Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, USA.

The title compound, 16-epi-latrunculin B (3), has been isolated from the sponge Negombata magnifica collected from the Red Sea near Hurghada, Egypt. This new natural product was determined to be an epimer of latrunculin B (1), which was found in the same sponge collection. The structure of 3 was initially deduced from proton and carbon NMR chemical shift trends and proton-proton nuclear Overhauser effect experiments. The cytotoxicity (murine tumor and normal cell lines) and antiviral (HSV-1) properties of 3 and 1 were determined. A computational study applicable to this class of stereochemical problems was then investigated. Specifically, the complete set of vicinal and allylic coupling constants was calculated for each of the four diastereomers whose configurations differed at C(8) and C(16). These computed J's were then compared with the experimental J values (28 in number) determined for 1 and 3. This analysis resulted in the same assignment of relative configuration for compound 3 reached using the more classical methods. The validity of the method is established by the fact that the 28 computed coupling constants for (known) 1 and (newly determined) 3 varied from the experimental J values with an average of just 0.57 and 0.53 Hz, respectively. This strategy represents a general, powerful, and readily adoptable tool for determining the relative configuration of complex molecules.
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http://dx.doi.org/10.1021/ja025734lDOI Listing
June 2002
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