World Applied ISSN 1818-4952 ‘© IDOSI Publications, 2008 720-723, 2008 Antimicrobial Activity of Stable Spiro-Endoperoxides by Sunlight Mediated Photooxygenation of 1,2-0-Alkylidene-5()-eno-5,6,8- trideoxy-o-D-ylo-oct-1,4- furano-7-aloses 'Mustafa Oskay, ‘Nilgiin Yenil and *Kadir Ay "Department Biology, Faculty of Sciences and Arts, Celal Bayar University, ‘Campus of Muradiye, 45030, Manisa, Turkey "Department of Chemistry, Faculty of Sciences and Arts, Celal Bayar University, Campus of Muradiye, 45030, Manisa, Turkey Abstract: Some 1,2-O-alkylidene-5(F)-en0-5,68-trideoxy-o-D=ylo-oct-1 4-furano-7-uloses derivatives were evaluated for their i vitro antimicrobial activities against Staphylococcus aureus (ATCC 6538P), methicillin, resistant Staphplococeus aureus (ATCC 95047), Escherichia coli, Sarcina lutea (ATCC 9341NA), Salmonella typhimurium (CCM. 5445), Pseudomonas fluorescens, Serratia marcescens (CCM. 583), Enterobacter aerogenes (ATCC 13047D) and Candida albicans. All synthesized compounck showed significant activity against the tested microorganisms with inhibition zones ranging from 8 to 18 mm, Key words: Antimicrobial activity * Medicinal chemicals + Synthetic substances * Spiro-endoperoxides + Twkey INTRODUCTION Miorabial. diseases are now more fiequent than doing the fist af of the contary, being sil difficult to diagnose clinically. During the later half of the century, particularly during the past two decades, a number of different classes of antibacterial and antsfiangal agents hhave been discovered [1-4]. Although. since the iscovery of several aynthetio and semi-synthatic antibacterial sulfa drugs, nitrofuranes, penicillin, cephalosporins, tetaeyclies, macrolides and ‘oxazolidinones and antifungal agents such as faconazole, ketoconazole and miconazole, inching amphotericin B, there has been much progress in this field. Despite advances in antibacterial and antifungal therapies, many problems remainto be solved for most antimicrobial drugs available [2,5], For example, appearance of multi-drug resistant Gram-positive bacteria, in particular, meticlline resistant Staphylococcus aureus and vaneomyeine sesiatant Baterocooe is causing a serious menace [1,3] In our previous study [68], we reported the synthesis of various spito-endoperoxides by sunlight- mediated photooxygenaton of 1,2-O-alkylidene-5(E)-eno- 5,6,8+trideoxy-@-D-xylo-oct-l,4-furano-7-uloses derivatives and now we wish to report the antimicrobial activities of the some of these compounds against some Gram positive, Gram negative bacteria and Candida albicans. MATERIALS AND METHODS ‘Tested Compounds: The tested compounds (2a-c) which hhaye been previously synthesized [68] by sunlight- mediated photooxygenation of 3-O-acsty] and 3-O-methyl erivatives of 1,2-O-alkylideno-5(B)-eno-5,6,8+rideoxy-0.- Dexylo-cet-1,4-furano-7-uloses are shown in Figure 1 Microorganisms and Growth Conditions: For the evaluation of the antimicrobial activity of the substances in vitro, the following strains were used: Staphylococcus ‘aureus ATOC 6538P, methicillin resistant Staphylococcus aureus ATCC 95047 (MRSA), Escherichia coli, Sarcina lutea ATCC 934INA, Salmonella typhimurium CCM. 54443, Pseudomonas fluorescens, Serratia marvescens CCM 583, Enierobacier aerogenes ATCC 13047D and for yeast Candida albicans ATCC 10231, Cultures of these bacteria were grown in Mueller-Hinton Broth at 37°C for 24h and the smdied yeast was incubated in Corresponding Author: Dr. Mustafa Oskay, Department of Biology, Faculty of Sciences and Arts, Celal Bayar University, Campus of Muradiye, 45030, Manisa, Turkey 720World App, Set. J, 4 (9 720723, 2008 9 San ight 0, £0 > to, co GR, ®, PSe Lo R, a { & 1a 22 (40%) th RCRA“ BR, 2 (64a) te R=COR= FR, 2e (omy Fig. 1: The tested compounds (24-c) synthesized by sunlight-nediated photooxygenation, "2 (R)-3-0-AcetylSeno-47-epidieny-1,2-0 -isopropylisene-5,68-trideaxy-o-D-threo-1,4-furano-4,7- ccescns CCM S88 0 o a mo a 30 ND E eropemes ATCC SOND 26 o o a 30 @ ne xo C alicane 8700 10281 nD. 6 6 6 x 6 »» 2 Baca teed in MIA mein yen inPDA 1 NA - Nols oc (30 pases NV - Nowebinin (30 nde AMP ~ Anil (10 uisesP-Penicilne G 10 iu.ees ERY - throm (15 pe IPM mien (10 pie: VA - Vans 0 pac; CHL -Chlrapbenizl 0p), NYS - Netti 0 ps), Diameter fini kin zone in mm ncating se ime (6) * essa “ail inition; 6-no xiv; ND not detent ‘against Sarcina Iu‘eo but lower than that of standard antibiotics (Table 2), except the nalidixic acid and vancomycin. The compounds were also tested against Candida albicans for their antimycotic activity and inhibitions for 2a, 2b and 2ewere observed 12, 14 and 10 mum, respectively. On the other hand, negative contol inhibited test microorganisms ranged from 2 to mm and not included ealeulations. ‘The results of the present investigation clearly indicate that the compouncis with spiroketal groups are also important, since they are found in some biologically ative moleoules. For example, polyether antibiotics such as salinomycin and narasin contain spiroketal rings. Carbohydrate based compounds having such peroxyhemiketal groups could be used for treatment of infectious diseases caused by C. albicans and some pathogenic bacteria such as MRSA, S. aureus, E.coli and S. yphimmurium, Fusther, they could also be converted to now sugar derivatives, which otherwise would be difficult tosynthesize, For example, deoxygenation of the peroxide ‘group could lead to new spirodifuranose derivatives [8]. ‘The demansl for new effective antimicrobials is urgent and of great importance in the clinial health. Allied with this demand is the need for assays to detect new and previously undiscovered antimicrobials fom synthetic substances. REFERENCES Osterblad, M,,H. Anti, M, Raija, L, Tiina, P. Reijo, ‘M. Olli, H. Pentti and K. Pirkko, 2000, A Between- Species Comparison of Antimicrobial Resistance in Enterobacteria in Feeal Flora, Antimicrob, Agents (Chemother, 44: 1479-1484, Cuevas, 0, C.Emilia, V. Ana, G- Fesus, $C. Matilde, S. 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