Curriculum Vitae
Prof.Dr. Seif-Eldin N. Ayyad
Present address
Department of Chemistry Phone: 0500096687
Faculty of Science
KingAbdulazizUniversityPO Box 80203
Jeddah 21589 E-mail
Saudi Arabia
Permanent address, Dept. of Chem., Dammietta Faculty of Science, MansouraUniversity, Mansoura, Egypt
Date of Birth May. 2, 1959
Place of Birth Dakahlia, Egypt
EDUCATION
B.Sc. 1981MansouraUniversity, Faculty of Science, Department of Chemistry, Mansoura, Egypt.
M. Sc. 1985 “Some Reactions on Unsaturated Keto Compounds.”MansouraUniversity, Faculty of Science, Department of Chemistry, Mansoura, Egypt.
Ph. D. 1990 “Chemical Studies of the Egyptian Alga, Laurencia obtusa.” MansouraUniversity, Faculty of Science,Department of Chemistry, Mansoura, Egypt
POSITIONS
2004- present Professor of organic chemistry (Natural products) Mansoura, University, Faculty of Science, Department of Chemistry,
1997- 2004 Associate Professor, MansouraUniversity, Faculty of Science, Department of Chemistry
1997- 1990 Lecturer, MansouraUniversity, Faculty of Science, Department of Chemistry
1990- 1985 Assistant lecturer, MansouraUniversity, Faculty of Science, Department of Chemistry
1985- 1981 Demonstrator, MansouraUniversity, Faculty of Science, Department of Chemistry,
PUBLICATIONS
1- Rinng Expansion of Carbocyclic -Ketoester with Acetylenic Esters.
Abou-Elzahab, M. M.; Ayyad, S. N.; Zimaity, M. T.
Z. Naturforsch.(1986), 41b, 363.
Abstract
Cyclohexenonecarboxylate I (R = Ph, PhCH:CH; R1 = CO2Et) were treated with NaH and then HC.tplbond.CCO2Et to give 60-65% oxocyclooctadienedicarboxylates II. Similar treatment of oxobicyclooctadienecarboxylate III with NaH and MeO2CC.tplbond.CCO2Me gave 70% the oxobicyclodecatrienetricarboxylate IV. In contrast, similar treatment of I (R = PhCH:CH, R1 = H) with NaH and MeO2CC.tplbond.CCO2Me gave I (R = PhCH:CH, R1 =MeO2CH:CCO2Me), which underwent photochem. cyclization to give tricyclooctanonedicarboxylate V. Other ring expansion reaction of I are also reported.
2- Novel Heterocyclic System. Synthesis ofAzabicyclo[3.3.1]non-6-ene and Azabicyclo[4.3.1]
deca-7-ene Derivatives.
Abou-Elzahab, M. M.; Sarhan, A. A.; El-Agamey, A. A.; Ayyad, S. N.
Proc. 1st Chem. Conf., Fac. Sci. Mans. Univ. September (1986),24-26.
3- Three Halogenated Metabolites from Laurencia obtusa.
Ayyad, S. N.; Dawidar, A. M.; Dias H. W.; Howie, R. A.; JakupovicJ.; Thomson,R. H.
Phytochemistry (1990), 29, 3193.
Abstract
New chamigrenes, hurgadol(I) and -snyderyl acetate(II), and a new C15-cyclic ether-enyne, hurgadenyne(III), have been isolated from L. obtusa. They were identified by spectroscopic methods. A crystal structure was obtained for I.
4- Phytochemical Study of the Red Alga Laurencia obtusa Grown in Egypt.
Dawidar, A. M.; Ayyad, S. N.; Abdel-Mogib, M.
J.Pharm. Sci. (1992), 33,921.
Abstract
Ten natural products were isolated from L. obtusa (collected from Hurgada). Seven of these are the known products n-heptadecane, obtusane, 3-bromo-8-epicaparrapi oxide, (E)-2-tridecyl-2-heptadecenal, -snyderol, palmitic acid, and cholesterol. The 3 new compds. were identified as hurgadenyne, -snyderyl acetate, and hurgadol.
5- Lactones from Pituranthos tortusus.
Abdel-Mogib, M.; Ayyad, S. N.;Metwally, M. A.; Dawidar, A. M.
Pak. J. Sci. Ind. Res.(1992), 35, 93.
Abstract
Ligustilide, ligusticumbisabolene, and myristicin were isolated from the aerial parts of Piturantho. tortusus.
6- A Sesquiterpene Glucoside from Reichardia tingitana.
Abdel-Mogib, M.; Ayyad, S. N.; Abou-Elzahab, M. M.; Dawidar, A.M.
Phytochemistry (1993), 34, 1434-1435.
Abstract
R. tingitana var. orientalis afforded, in addn. to lupeol, taraxasterol, and the corresponding acetates, three sesquiterpene lactones of the guaianolide type including a new glucoside. The structures were elucidated by spectral methods.
7- Synthetic approaches to some new fluorescent dyestuffs for synthetic polymer fibers.
Synthesis of new 2-(4'-hetarylphenyl)-1,2,3-triazolo(4,5-b)pyrido(1',2'-a)-benzimidazoles,
Girges, M. M.; Hanna, M. A.; Ayyad, S. N.
Presented in the Eighth European Symposium on Organic Chem. (ESOC 8),Barcelona,
Spain, (1993) August 29 - September 3.
Pigment & Resin Technology (1995), 24(2), 9-12
Abstract
Triazolo[4,5-b]pyrido[1,2-a]benzimidazole derivs. contg. oxazole, 1,2,4-triazole, and imidazole groups were prepd. as fluorescent brightening agents.
8- Triterpenes from Euphorbia retusa.
Ayyad, S. N.
Alex. J. Pharm. Sci.(1994), 8, 23.
Abstract
Phytochem. study of the E. retusa resulted in the isolation and identification of 4 triterpenes: erythrodiol, uvaol, betulin, and 24-methylene-9, 19-cyclolanostan-3-yl palmitate (I). I was isolated for the 1st time from this species. Identification of the isolated compds. was established by spectral methods.
9- A Sesquiterpene Ether from Laurencia obtusa.
Ayyad,S.N.; Jakupovic, J.; Abdel-Mogib, M.
Phytochemistry (1994),36, 1077-1078
Abstract
A new sesquiterpene ether, dactyloxene D (I), was isolated from Laurencia obtusa. The structure was identified by spectroscopic methods and stereochem. was established by NOE difference spectroscopy.
10-Epoxidation of the Natural b-Snyderol to Potential Alkylating Agents of DNA,
Ayyad, S. N.; Waly, M. A.; Girges, M. M.
Pharmazie (1994), 49, 534-535.
Abstract
Epoxidn. of the title compd. I by 3-ClC6H4C(O)OOH in CH2Cl2 gave 20% of the known E- and Z-epoxides and 30% monoepoxide II.
11- Caulerpin: An Antitumor Indole Alkaloid from Caulerpa racemosa.
Ayyad, S. N.; Badria, F. A.
Alex. J. Pharm. Sci. (1994), 8, 217.
Abstract
The presence of an antitumor compd. has been revealed in the ethanolic ext. of Caulerpa racemosa collected from Hurghada, Egypt. The physicochem. study (IR, MS, 1H- and 13C-NMR) resulted in full assignment of the antitumor compd. as caulerpin (I). I exhibited a moderate in-vitro antitumor activity against crown gall tumor.
12- Constituents of Onopordon alexandrinum.
Ayyad, S. N.; Hanna, M. A.; Abdel-Mogib, M.
Egypt. J. Pharm. Sci. (1994), 35, 553.
Abstract
Constituents of O. alexandrinum were extd., de-fatted and analyzed using column chromatog. to give taraxasterol, lupeol, -sitosterol, stigmasterol, scutellarein 4'-Me ether and takakin. The structure of the hitherto isolated products were inferred by high-field 1H-NMR spectroscopy.
13- Synthetic Approaches to Some New Sulfur-Containing Heterocycles of Anticipated
immunosuppressive Activity.
Girges, M. M.; Hanna, M. A.; Ayyad, S. N.
Phosphorous, Sulfur, Silicon Related Elements (1995), 104, 5-13.
Abstract
Several new isolated or fused heterocyclic ring systems, e.g., I, that accommodate the isothioureido functionality, often assocd. with immunosuppressive activity, were synthesized for possible use as immunosuppressive agents. Prepn. of these anchored heterocycles was achieved via a multi-step synthesis starting with the key intermediate thiazolyl thiourea deriv. II. Structure of the newly synthesized products was confirmed using both of elemental and spectral analyses. Test data were given for the prepd. heterocycles as immunosuppressive and antimicrobial agents.
14- Synthesis of 4H-Naphtho(1,2-b)pyrans, Benzocoumarins, 4H-Naphtho (2,1-b:6,5-b)
pyrans,4H-Naphtho(1,2-b:3,4-b) Dipyrans and Pyridine Derivatives.
El-Taweel, F. M.; Ayyad, S. N.; El-Agamey, A. A.; Sowellim, S. Z.
Anal. Quim. (1995), 91, 589-593.
Abstract
The reaction of (phenylmethylene)propanedinitriles with 1,6-naphthalenediol gave enaminonaphthopyrans I (R = H, OMe, Cl). The reaction of (arylidene)cyanoacetate with 1,6-naphthalenediol gave benzocoumarins. The naphthodipyrans such as II (X = cyano, ethoxycarbonyl; R = H, OMe, Cl) were also prepd.
15- Reaction on Activated Nitriles: Routes for Synthesis of Some New Fused Heterocycles
Containing Nitrogen.
Ayyad, S. N.; El-Taweel, F. M.; Sofan, M. A.; Abu El-Maati, T. M. El-Agamy, A. G.
Anal. Quim. (1995), 91, 711-715.
16- A Novel Synthesis of the Imidazo[4,5-d]azepine Ring System.
Waly, M. A.; Said, S. B.; Ayyad, S. N.
Polish J. Chem. (1996), 70, 296-301.
Abstract
A novel synthesis of imidazo[4,5-d]azepine I from -diketone was described. The starting materials N-(3-ethoxy-3-oxopropyl)-N-(phenylmethyl)--alanine Et ester or 3,3'-[(phenylmethyl)imino]bis[propanenitrile] were converted to I. Furthermore, tetrahydro-1-(phenylmethyl)-1H-azepine-4,5-dione was also converted to I by condensation with S-methylisothiourea sulfate.
17- Reaction of 1,3-Dicarbonyl Compounds with Nitriles: Synthesis of Pyrazolo [1,5-c]-
1,2,4-Triazines, Pyridines, 4H-Pyrans and 4H-Indeno[1,2-b]Pyran Derivatives
Seif-Eldin N. Ayyad, Fathy M. A. El-Taweel and Ahmed i. Osman
Alex. J. Pharm. Sci., (1995), 9(3), 217-220.
Abstract
Several new pyrazolopyridotriazines, pyridines, 4H-pyran and H-indeno[1,2-b]pyran derivs. were prepd. from -dicarbonyl compds. MeCOCH2CONHAr (Ar = Ph, C6H4OMe-4), indane-1,3-dione and ylidenes R1CR:C(CN)CN (R1 = Ph, C6H4Cl-4, C6H4OMe-4, 2-thienyl; R = H, Me) as starting materials.
18- Photooxygenation Reactions of Natural Piperine.
Ayyad, S. N.; Elgendy E. M.
Heterocyclic Comm. (1998), 4, 449-450.
Abstract
The natural piperine was photooxygenated using Tungsten-halogen lamp to give 1N-piperidino-1-oxo-5-(3'-formatyl-4'-hydroperoxyl phenyl)-2,4-pentadiene (I) and 1-N-piperidino-1-oxo-5-(4'-formatyl-3'-hydroperoxyl phenyl)-2,4-pentadiene (II), whereas, if the reaction was carried out using sodium lamp a mixt. of I and II in addn. to a cyclicperoxide deriv. was obtained.
19- Inhibitory Effects of Extracts from the Marine Alga,Caulerpa Taxifolia, and of Toxins from
Caulerpa Racemosa on Multixenobiotic Resistance in the Marine Sponge, Geodia Cydonium.
Schroder, H. C.; Badria, F. A.; Ayyad, S. N.; Batel, R.; Wiens, M.; Hassanein, H. M. A.;
Kurelec, B.; Muller, W. E. G.
Env. Tox. Pharm. (1998), 5, 119-126.
Abstract
The invasive growth of the introduced green alga Caulerpa taxifolia, already affecting the richness and diversity of the littoral ecosystems, has become a major ecol. problem in the Mediterranean Sea. Previously, the authors demonstrated that the water pollutant tributyltin induces apoptosis in tissue of the marine sponge Geodia cydonium at concns. of 3 M and higher. Here the authors show that exposure of G. cydonium to low (non-toxic) concns. of Caulerpa ext. or purified caulerpin (10 g/mL) together with low doses of tributyltin (1 M; non-toxic), results in a strong apoptotic effect. Evidence is presented that the enhancement of toxicity of tributyltin by Caulerpa ext. is at least partially caused by inhibition of the multixenobiotic resistance (MXR) pump by the algal toxin. Caulerpa ext., as well as caulerpin, strongly enhance the accumulation of the text substrate of MXR, rhodamine B, in the gills of the mussel Dreissena polymorpha, used as a model system for testing MXR-inhibiting potential.
20- Development of Synergistic NMR and Molecular Mechanics Strategies for Determining
Natural Product Stereochemistry.
Hoye, T. R.; Ayyad, S.N.; Judd, A. S.; Koltun, D. O.; Renner, M. K.
Pure Appl. Chem. (1998), 70, 2134-2134.
21-New antitumor agents: Structure and synthesis studies.
Hoye, Thomas R.; Ayyad, Seif-Eldin N.; Judd, Andrew S.; Shier, W. Thomas
Book of Abstracts, 216th ACS National Meeting, Boston, August 23-27 (1998
Abstract
Two isomeric 4-methylene-2-cyclohexenones sharing constitution 1 have been isolated from Ottelia alismoides, a water lilly growing in the delta region of the Nile River. Each shows impressive in vitro antitumor potency and selectivity profiles. Through a parallel set of nmr and computational studies, the relative configurations of the two isomers have been deduced. This has encouraged synthesis efforts. Details of the structure detn. and progress with the synthesis will be presented.
22- Otteliones A and B:Potently Cytotoxic 4-Methylene-2 cyclohexenones from Ottelia
alismoides.
Ayyad, S. N.; Judd, A. S.; Shier, W. T.; Hoye, T. R.
J. Org. Chem. (1998), 63, 8102-8106.
Abstract
Two diastereomeric 4-methylene-2-cyclohexenones, otteliones A and B (I), have been isolated from the freshwater plant Ottelia alismoides collected in the Nile Delta, Egypt. I show remarkable in vitro cytotoxicity against various cancer cell lines. Ottelione B proved to have a constitution identical to that of the known (constitution only) ottelione A. The relative configurations of I were studied by NOE and by the combination of mol. modeling and 1H NMR coupling const. anal. A unique relative configurational assignment ( was deduced for ottelione B; ottelione A was assigned one of two alternative diastereomers
23- Cytotoxic Bicyclic Diterpenes from the Brown Alga Sargassum crispum.
Ayyad, S.N.; Slama, O.M.; MoKhtar, A. H.; Anter, A.F.
Boll. Chim. Farmac. (2001), 140, 155-159.
Abstract
Study of the brown alga Sargassum crispum collected from Red Sea resulted in the isolation of a new diterpene with a hydroazulene skeleton, Sargassinone, some fatty acid Et esters and some fatty acids. The identification of the isolated metabolites was established mainly by spectral methods and chem. transformation of sargassinone to its acetate. The two new diterpenes exhibited substantial cytotoxic activities, as indicated by their IC50 values at the dose of 10 g/mL or less.
24- A New Cytotoxic Stigmastane Steroid from Pistia stratiotes,
Ayyad,S.N.
Pharmazie (2001), 56, 212-214
Abstract
A new cytotoxic stigmastane, 7-hydroxy-4,22-stigmastadien-3-one (I), together with two known cytotoxic stigmastanes and a norisoprenoid, have been isolated from the aquatic plant pistia stratiotes. The structure detn. was accomplished by spectroscopic methods.
25-Toward Computing Relative Configurations:16-epi-Latrunculin B, a New Stereoisomer of the
ctin Polymerization Inhibitor, Latrunculin B.
Hoye, T. R.; Ayyad, S. N.; Eklov, B. M.; Hashish, N. E.; Shier, W. T.; El Sayed, K. A.;
Hamann, M. T.
J. Am. Chem. Soc. (2002), 124, 7405-7410.
Abstract
The title compd., 16-epi-latrunculin B (I), has been isolated from the sponge Negombata magnifica collected from the Red Sea near Hurghada, Egypt. This new natural product was detd. to be an epimer of latrunculin B (II), which was found in the same sponge collection. The structure of I was initially deduced from proton and carbon NMR chem. shift trends and proton-proton nuclear Overhauser effect expts. The cytotoxicity (murine tumor and normal cell lines) and antiviral (HSV-1) properties of I and II were detd. A computational study applicable to this class of stereochem. problems was then investigated. Specifically, the complete set of vicinal and allylic coupling consts. was calcd. for each of the four diastereomers whose configurations differed at C(8) and C(16). These computed J's were then compared with the exptl. J values (28 in no.) detd. for I and II. This anal. resulted in the same assignment of relative configuration for compd. I reached using the more classical methods. The validity of the method is established by the fact that the 28 computed coupling consts. for (known) II and (newly detd.) I varied from the exptl. J values with an av. of just 0.57 and 0.53 Hz, resp. This strategy represents a general, powerful, and readily adoptable tool for detg. the relative configuration of complex mols.
26- NMR Application of Mosher’s Method: The absolute configurations of FucoXanthin from
Turbinaria triquatra
Ayyad,S. N. ; Diab, M.
Alex. J. Pharm. Sci. (2002), 16, 27-30
Abstract
Recent investigations on the constituents of the marine brown alga Turbinaria triquatra have led to the isolation of fucosterol and fucoxanthin. The abs. configuration of the secondary alc. in fucoxanthin was deduced by 1H-NMR anal. of Mosher ester derivs. Structure detn. of these compds. was accomplished by spectroscopic methods. Cytotoxicity of the ext. was assayed against NINH3T3 fibroblast and KA3IT cancer mouse cell lines.
27- Isolation and Structure of Biologically Active Glycosphingolipids from the marine Sponge
Haliclona species.
Seif-Eldin N. Ayyad.
8th IBN SINA International conference, (2002), February 16-19.
Mansoura Science Bulletin, A: Chemistry (2004), 31(1), 115-124.
Abstract
A new cytotoxic glycosphingolipid, haliclonacerebroside (I), together with the known carotenoid, zeaxanthin, and the known nucleoside, thymidine, were isolated from the marine sponge Haliclona. The structure of each isolated compd. has been detd. on the basis of spectroscopic and chem. evidence.
28- Cytotoxic Bicyclic Diterpenes from the Brown Alga Cystosira myrica.
Ayyad, S. N.; Abdel-Halim, O. B.; Shier, W. T.; Hoye,T. R.
Zeitschrift fur Naturforchung, (2003),58c, 33-38
Abstract
Cytotoxicity-guided fractionation of the alc. ext. of the brown alga Cystoseira myrica afforded four new cytotoxic hydroazulene diterpenes, dictyone acetate (I), dictyol F monoacetate (II), isodictytriol monoacetate (III), and cystoseirol monoacetate (IV), together with two known cytotoxic hydroazulene diterpenes, pachydictyol A and dictyone. The constitution of each isolated compd. has been detd. on the basis of spectroscopic and chem. evidence. The compds. were assayed against a normal fibroblast cell line and 2 virally transformed forms.
29- The Structural Determination of A New steroidal Metabolite from the Brown Alga
Sargassum asperifolium
Ayyad, S. N. ; Sowellim, S. Z.; El-Hosini, M.S.; Abo-Atia, A.
Zeitschrift fur Naturforchung, (2003), 58c, 333-336.
Abstract
An investigation of the natural products chem. of the brown alga S. asperfolium from the Red Sea yielded a new steroidal metabolite, saringosterone (I), known steroidal metabolite saringosterol, and a known diterpene with a hydroazulene skeleton, dictyone. The identification of the isolated metabolites was established mainly by spectral methods and chem. transformation of the dictyone to its acetate.
30- Cytotoxic Metabolites, New Plakortide, Bicyclic Lactone and Cyclic Peroxides from the
Marine Sponge Plakortis
T. R. Hoye, S. N. Ayyad, M, Abo-Elkarm and M. T. Hamann.
7th International Conference on Chemistry and its Role in Development. (2003),
April 14-17.
Mansoura Science Bulletin, A: Chemistry (2003), 30(2), 149-156
Abstract
As part of a program to discover new drugs for the treatment of tropical diseases, we use the bioassay-guided fractionation of the ext. of Jamaican Sponge Plakortis followed by preparative TLC and HPLC yielded several known and novel compd. (I). The structures of these compds. were elucidated by interpretation of spectroscopic data. These natural products show remarkable in vitro cytotoxicity against various cancer cell lines.
31- Sensitivity of Human breast Carcinoma Cells to Ottelione A and its analogues.
J. L. Dechaine, H. j. Lewis, S. N. Ayyad, T. R. Hoye, L. Sreerama.
Abstracts of Papers, 225th ACS National meeting, new Orleans, LA, United States,
(2003), March 23-27.
Abstract
Two diastereomeric 4-methylene-2-cyclohexenones, viz. otteliones A and B, have been isolated from a freshwater plant Ottelia alismoides and found to inhibit cell growth at nanomolar concns. Ottelione A has been shown to inhibit tubulin polymn.; accordingly exerts its cytotoxicity via apoptosis. We now report prepns. of several analogs of ottelione A and their cytotoxicities. Cytotoxicity was tested using a panel of 8 human breast carcinoma cell lines (24 h continuous exposure) and a colony-forming assay. The cell lines exhibit differential cellular sensitivity to these compds., e.g., the LC50 values for ottelione A were 25-50 nM; O-methylottelione A were 50-200 nM and otteliol A were 75-3000 nM. Ottelione A was found to be the most toxic and the modifications introduced on it led to decreased cellular sensitivity irresp. of the cell line tested.
32- Humulene Sesquiterpene Lactones from Asteriscus schimperi
A. M. Dawidar, S. N. Ayyad, M. Abdel-Mogib and W. M. Alarif
J. Saudi Chem. Soc., (2005), 9 (1), 137-142.
Abstract
Asteriscus schimperi is a rarely distributed species, belongs to the family Compositae. This species has not been previously investigated for natural products. In this article we report the isolation and structure elucidation of two bisabolone sesquiterpenes and four humulene sesquiterpene lactones. The bisabolone derivs. are bisabola-2,10-dien-1-one 1 and 6-hydroxybisabola-2,10-dien-1-one 2, while the humulene derivs. are 9-oxohumula-4-en-6,15-olide 3, 9-oxohumula-4,7(E)-dien-6,15-olide 4, 9-oxohumula-1(10)(Z),4,7(E)-trien-6,15-olide 5, and 9-oxohumula-1(10)(E),4,7(E)-trien-6,15-olide 6. The humulene sesquiterpene lactone 4 is a new one since it has not been previously isolated from any natural source. The structure elucidation of the isolated compds. is based on spectral anal.
33-Four pyrrole Alkaloids from Marin Spong Axinella carteriS. A. Basaif,* N. E. Hashish# and S. N. Ayyad*J. Saudi Chem. Soc., (2005), 9 (3), 683-686AbstractStudy of the marin sponge Axinella carteri collected from Red Sea in Jeddah, Saudi Arabia resulted in the isolation of four pyrrole alkaloids with pyrololactams skeleton. Compounds 3 and 4 have not been previously published from this species. The identification of the isolated metabolites was established mainly by 1H, 13C-NMR and HRMS spectra.
34- Structure of New Sphingolipids from the Marine Sponge Haliclona Species.
S. O. S. Bahaffi* N. E. Hashish# and S. N. Ayyad*
Natural Product Research (2007), gall proof 15-11-2007
Abstract
In a continuation of study the marine sponge Haliclona species we isolate a new cytotoxic four-component mixture of sphingolipids, (1a-d) and a known haliclonacerebroside (2). Methanolysis the sphingolipids 1a-d and haliclonacerebroside 2 in methanol to produce the fatty acid methyl ester (FAM) and using the GC/MS to determined the length of the fatty acid methyl ester. Also the structure of each isolated compound has been determined on the basis of spectroscopic data and chemical evidence.