A Suitable Base Material for Composite Resin Restorations

sustenance for thought and chemical substance Toxicology 45 ( cardinal hundred7) 16501661 www. elsevier. com/locate/foodchemtox A comparison of chemical, emmetioxidant and germicide studies of cinnamon bark sputter paging and shinny explosive crude rock crude food colours, oleoresins and their liftstituents q Gurdip Singh b a,* , Sumitra Maurya a,1 , M. P. deLampasona b, Cesar A. N. Catalan b a chemistry Department, DDU Gorakhpur University, Gorakhpur 273 009, India Instituto de Quimica Organica, Universidad Nacional de Tucuman, Ayacucho 471, S. M. de Tucuman 4000, Argentina Received 31 August cc5 accepted 22 February 2007Abstract The antioxidant, antimycotic agent and antibacterial potencys of inconstant inuncts and oleoresin of Cinnamomum zeylanicum Blume ( toss and utter) were investigated in the exemplify study. The oleoresins be withdraw shown excellent natural help for the prohibition era of unproblematic and secondary c rock petroleum oxidation pr oducts in chinese chinese mustard anoint added at the absorption of 0. 02% which were evaluated utilize peroxide, thiobarbituric paneling, p-anisidine and carbonylicicic reputes. Moreover, it was that supported by other complementary antioxidant check- step forward procedures such as ferrous thiocyanate mode in linoleic acid system, cut down power, chelating and scavenging e? cts on 1,1 0 -diphenyl-2-picrylhydrazyl (DPPH) and hydroxyl al-Qaidas. In anti microbial investigations, victimization invert petriplate and food poisonous substance techniques, the alternate and shin volatile petroleums has been ready to be highly e? elelectroconvulsive therapyroshock therapyive against each the probeed fungus kingdom tho genus genus Aspergillus ochraceus. However, pagination oleoresin has shown stifling sensation for genus Penicillium citrinum whereas speak oleoresin has ca calld bring to pass mycelial regularize subdueion for Aspergillus ? avus and A. och raceus on with Aspergillus niger, Aspergillus terreus, P. citrinum and Penicillium viridicatum at 6 lL. education nutrient agar well di? sion method acting, thumb volatile crude embrocate and oleoresin have shown best(p) results in comparison with bark volatile crude color, oleoresin and commercial bactericide, i. e. , ampicillin. flub chromatographicalmass spectroscopy studies on folio volatile inunct and oleoresin resulted in the identi? cation of 19 and 25 subdivisions, which accounts for the 99. 4% and 97. 1%, respectively of the tot numerate and the study element was eugenol with 87. 3% and 87. 2%, respectively. The analytic thinking of cinnamon bark volatile fossil petroleum color showed the strawman of 13 components method of accounting for blow% of the total amount. E)-cinnamaldehyde was put in as the major component along with d-cadinene (0. 9%), whereas its bark oleoresin showed the presence of 17 components accounting for 92. 3% of the total amo unt. The major components were (E)-cinnamaldehyde (49. 9%), along with some(prenominal)(prenominal) other components. O 2007 Elsevier Ltd. All rights reserved. Keywords Cinnamomum zeylanicum Blume Eugenol Cinnamaldehyde Antioxidant assay 1. entering Free foundation receptions occur in human corpse and food systems. Free stands, in the digit of reactive type O and crack up 57.Corresponding author. Tel. +91 551 2200745 (R)/2202856 (O) fax +91 551 2340459. E-mail address emailprotected com (G. Singh). 1 afford address Agarkar Research give, Pune 411 004, India. * q nitrogen species, ar an integral part of common physiology. An over production of these reactive species arouse occur, due to oxidative straining brought ab prohibited by the imbalance of bodily antioxidant defence system and easy radical formation. These reactive species can react with biomolecules, ca using cellular crack and death.This may lead to the development of chronic diseases such as cancers and t hose that drive the cardio- and cerebrovascular systems. The consumption of fruits and vegetables (Peschel et al. , 2006) chastening antioxidants has been found to o? er protection 0278-6915/$ converge front matter O 2007 Elsevier Ltd. All rights reserved. doi10. 1016/j. fct. 2007. 02. 031 G. Singh et al. / regimen and chemic Toxicology 45 (2007) 16501661 1651 against these diseases. Dietary antioxidants can augment cellular defences and help to delay oxidative damage to cellular components (Halliwell, 1989).Besides playing an important role in physiological systems, antioxidants have been utilise in food industry to suffer the shelf life of foods, especially those rich in polyunsaturated fats. These components in food are readily oxidized by molecular oxygen and are major cause of oxidative deterioration, nutritional losses, o? ?avour development and discoloration. The extension of synthetical antioxidants, such as propyl gallate, hardlyylated hydroxylanisole (BHA), bu tylated hydroxyltoluene (BHT) and tertiary butylhydroquinone has been wide utilize industrially to realise lipide oxidation in foods.However, the use of these synthetic antioxidants has been questioned due to their say-so health risks and toxicity (Kahl and Kappus, 1993). The search for antioxidants from immanent sources has real such(prenominal) attention and e? orts have been put in to identify compounds that can act as suitable antioxidants to replace synthetic ones. In addition, these naturally occurring antioxidants can be formulated as operational foods and nutraceuticals that can help to prevent oxidative damage from occurring in the body.Plants contain a variety of substances called Phytochemicals (Pratt, 1992), that owe to naturally occurring components present in sows (Caragay, 1992). The phytochemical preparations with forked functionalities in preventing lipid oxidation and antimicrobial properties have tremendous potential for extending shelf life of food produ cts. Several research groups around the populace have succeeded in ? nding and identifying natural antioxidants from herbs and spicinesss using di? erent model systems.The antioxidant fulfill at law of mot family herbs such as rosemary, discerning, summer savory and borage are overly well documented (Bandoniene et al. , 2002 Djarmati et al. , 1991 Ho et al. , 2000 Aruoma et al. , 1996 Cuvelier et al. , 1994 Wong et al. , 1995 Chang et al. , 1997 Madsen et al. , 1996 Gordon and Weng, 1992 Takacsova et al. , 1995). However, the redolent(p) spicy and medicinal plants from Laureceae family are less extensively studied. cinnamon bark (Cinnamomum zeylanicum Blume, syn C. verum, family Laureceae) is a widely used spice and have many applications in perfumery, ? voring and pharmaceutical industries. Although, the chemical constituents of leaf and bark inbred vegetable oils of cinnamon have been studied (Raina et al. , 2001 ? Simic et al. , 2004 Jayaprakash et al. , 1997), the poten tial antioxidant properties have soon enough not been studied and it seems that investigation on oleoresins are scarce. Hence, in the present work, attempt has been made to explore the possible antioxidant and antimicrobial properties by di? erent methods which can give much comprehensive information especially when the e? ectiveness of multi component natural oleoresins is investigated.The objective of present investigation is to compare the chemical motif of leaf and bark essential oils and oleoresins as well as abut the possibility of protecting the stored food materials against micro-organism and antioxidative behaviour on mustard oil using as additive by various methods. 2. Materials and methods 2. 1. chemics Thiobarbituric acid, pure components eugenol and cinnamaldehyde were received form Merck, Germany. Diphenylpicrylhydrazyl (DPPH), carbendazim were procured from Sigma (SigmaAldrich GmbH, Sternheim, Germany) and linoleic acid from Across ( immature Jersey, USA).BHT, BH A, and 2,4-dinitrophenylhydrazine were purchased from s. d ? ne-chem Ltd, Mumbai, India. ampicillin was purchased from Ranbaxy Fine chemicals Ltd. , New Delhi, India. Crude mustard oil was purchased from local oil mill, Gorakhpur, India. All solvents used were of analytical grade. 2. 2. Sample extraction Cinnamon leaves and barks were purchased from local market of Gorakhpur, Uttar Pradesh, during January 2004 and coupon specimens were kept at the Herbarium of the Science faculty, DDU Gorakhpur University, Gorakhpur.Cinnamon leaves (250 g) and barks (50 mesh particle size) were hydrodistilled using Clevengers apparatus to yield essential oils (3. 1% and 2. 5%, respectively). Oleoresins were obtained by extracting 25 g of powdered spice with 250 mL of acetone for 2 h in a Soxhlet extractor. The solvent was evaporated by placing the sample in a vacuum drier under reduced pressure. The viscous oleoresins for leaves and barks, with yield 6. 9% and 9. 7%, respectively, were obtained. Bo th essential oils and oleoresins were stored in cold condition and until further use. 2. 3. chemical characterization 2. . 1. Gas chromatography (GC) A Hewlett Packard 6890 (Analytical Technologies SA, Buenos Aires, Argentina) gas chromatograph equipped with chromatography column HP-5 (5% phenyl methylsiloxane, length 30 m knowledgeable diameter 0. 25 mm ? lm thickness 0. 25 lm) was used for the analysis whose injector and detector temperatures were well-kept at 240 and 250 C, respectively. The amount of the samples injected was 0. 1 lL in split mode (801). toter gas used was helium with a ? ow rate of 1. 0 mL minA1. The oven temperature for essential oils were programmed linearly as follows 60 C (1 min), 60 185 C (1. C minA1), 185 C (1 min), 185275 C (9 C minA1 ), 275 C (5 min) whereas for oleoresins it was as follows 70 C (1 min), 70one hundred seventy C (1. 5 C minA1), 170 C (1 min), 170180 C (9 C minA1), 280 C (5 min). 2. 3. 2. Gas chromatographymass spectrometry (GCMS) c ompend of volatile oils and oleoresins were disappear on a Hewlett Packard (6890) GCMS system (Analytical Technologies SA, Buenos Aires, Argentina) coupled to a quadrupole mass spectrometer (model HP 5973) with a capillary column of HP-5MS (5% phenyl methylsiloxane, length = 30 m, inner diameter = 0. 25 mm and ? lm thickness = 0. 5 lm). The injector, GCMS interface, ion source and selective mass detector temperatures were retained at 280, 280, 230 and 150 C respectively. The oven temperature programmed for the volatile oils were same as provided for GC whereas for oleoresins, it was programmed linearly as follows 60 185 C (1. 5 C minA1), 185 C (1 min), 185275 C (9 C minA1), 275 C (2 min). The extract was held at 70 C (5 min), 70220 C (3 C minA1), 220280 C (5 C minA1) and held at 280 C for 5 min. 2. 3. 3. Components identi? cation The components of essential oil and oleoresins were identi? d on the posterior of comparison of their property indices and mass spectra with published entropy (Adams, 2001 plenitudeda, 1976) and computer matching with WILEY 275 and National contribute of Standards and Technology (NIST 3. 0) libraries provided with computer controlling the GCMS system. The results were also con? rmed by the comparison of the compounds elution order of battle with their relative retention indices on non-polar form 1652 G. Singh et al. / provender and chemic Toxicology 45 (2007) 16501661 2. 4. 2. DPPH and hydroxyl radical scavenging e? ects The DPPH assay was carried out as described by Brand-Williams and his co-workers (1995). , 10, 15, 20, 25 lL of the sample were added to 5 mL of 0. 004% methanol outcome of DPPH. after a 30 min incubation period at room temperature, the absorbance was read against a vacuous at 515 nm. The assay was carried out in triplicate and analyses of all samples were run in duplicate and results are averaged. This test was adopted from a method described by Halliwell et al. (1987). Solutions of the reagents were alwa ys prepared freshly. The response mix contained in a ? nal account book of 1. 0 mL, one hundred lL of 2-deoxy-2ribose (28 mM in KH2PO4K2HPO4 bu? er, pH 7. ), 500 lL of various concentrations of the tested oils or the pure compounds in bu? er, 200 lL of 1. 04 mM EDTA and 200 lM FeCl3 (11 v/v), degree centigrade lL of 1. 0 mM H2O2 and one C lL of 1. 0 mM ascorbic acid. Test samples were kept at 37 C for 1 h. The bare(a) radical damage compel on the substrate, deoxyribose, was measured using the thiobarbituric acid test (Ohkawa et al. , 1979 Shimada et al. , 1992). 1. 0 mL of TBA (1%), and 1. 0 mL tricholoroacetic acid (2. 8%) were added to the test tubes and were incubated at deoxycytidine monophosphate C for 20 min. later cooling, absorbance was measured at 532 nm against a blank containing deoxyribose and bu? r. Reactions were carried out in triplicate. Inhibition (I) of deoxyribose degradation in pct was calculated in the chase way I? %? ? speed of lightX ? A0 A A1 =A0 ? where A0 is the absorbance of the control reaction, and A1 is the absorbance of the test compound. 2. 4. 3. Chelating e? ect and reducing power Chelating e? ect was determined according to the method of Shimada et al. (1992). To 2 mL of the mixture, consisting of 30 mM hexamine, 30 mM potassium chloride and 9 mM ferrous sulfate were added to 5, 10, 15, 20, 25 lL of essential oil or oleoresin in methanol (5 mL) and 200 lL of 1 mM tetramethyl murexide. subsequently 3 min at room temperature, the absorbance of the mixture was determined at 485 nm. A lower absorbance indicates a higher chelating power. EDTA was used as a positive control. The reducing power was carried out as described before (Oyaizu, 1986). Various amount (5, 10,15, 20 lL) of essential oil or oleoresin (dissolved in 2. 5 mL of methanol) abstruse with 2. 5 mL of 200 mM orthophosphate bu? er (pH = 6. 6) and 2. 5 mL of 1% potassium ferricyanide, and the mixture was incubated at 50 C for 20 min. After adding 2. 5 mL of 10% trichloroacetic acid, the mixture was centrifuged at 200 g for 10 min in Sigma 3K30 model centrifuger.The organic layer (5 mL) was immix with 5 mL of deionised water and 1 mL of 0. 1% ferric chloride and the absorbance read at 700 nm in a UV perceptible spectrophotometer. reported in the literature (Adams, 2001). The retention indices were calculated for all volatile constituents using a homologous series of n-alkanes C8C16. 2. 3. 4. Antioxidative assays in mustard oil Oxidative deterioration was monitored under modi? ed Shaal Oven test (Economou et al. , 1991). leafage and bark essential oils and oleoresins along with synthetic antioxidants and major components were added individually to unre? ned mustard oil at trains of 0. 2% (v/v). The initial PV value of oil is 1. 7 meq of O2/kg. Oxidative deterioration was periodically assessed by measuring the antioxidant parameters such as peroxide (PV), thiobarbituric acid (TBA), p-anisidine (p-An) and total carbonyl (TC) values. 2. 3. 5. PV and TBA values The rate of oil oxidation was monitored by the increase of peroxide values. About 3 g of each oil sample was weighed and subjected to iodimetric determination (AOCS, 1990). TBA values were evaluated according to the methods antecedently stated by some authors (Sidwell et al. , 1954) with clarified changes. To 10 g of oil sample, 0. 7% aq. thiobarbituric acid (20 mL) and benzene (25 mL) solution were added. This mixture was shaken continuously for 2 h using mechanical shaker. After 2 h, supported was taken and placed in boiling water-bath for 1 h. After cooling, absorbance of supernatant was measured at 540 nm with Hitachi-U-2000 spectrophotometer. 2. 3. 6. p-Anisidine value The test was per create according to the methods (AOCS, 1998,) antecedently stated by prior workers (Ottolenghi, 1959 Kikuzaki and Nakatani, 1993). In a 50 mL volumetric ? ask, 0. 6 g of oil sample was taken and volume was made using isoctane solution.From this solution, 5 mL was tr eated with 1 mL of 0. 25% of p-anisidine reagent and kept in dark for 10 min and absorbance was measured at 350 nm using a UVVIS spectrophotometer. 2. 3. 7. Total carbonyl value Carbonyl value was evaluated according to the methods as reported earlier (Frankel, 1998). About 4 g of sample was taken in a 50 mL volumetric ? ask and the volume was made up using carbonyl free benzene. Out of this, 5 mL was pippeted out and mixed with 3 mL of 4. 3% trichloroacetic acid and 5 mL of 2,4-dinitrophenyl hydrazine (0. 05% in benzene) in 50 mL volumetric ? asks.The mixture was incubated at 60 C for half an hour to convert free carbonyls into hydrazones. After cooling, 10 mL of KOH solution (4% in ethanol) was added and the volume was made with ethanol. After 10 min, absorbance was measured at 480 nm using UVVIS spectrophotometer. blank shell was prepared in the same manner substituting 5 mL of benzene instead of sample. A standard curve was drawn using valeraldehyde (50250 lg) in 5 mL of benzen e instead of sample. The total carbonyl was calculated with the help of the standard curve and expressed as mg of valeraldehyde per atomic number 6 g of sample. 2. 5. disinfectant use 2. 5. . Antifungal investigations In order to determine the antifungal e? cacy of the volatile oil and its oleoresin, the pathogenic fungus Aspergillus niger, Aspergillus ? avus, Aspergillus ochraceus, Aspergillus terreus, Fusarium moniliforme, Fusarium graminearum, Penicillium citrinum and Penicillium viridicatum were undertaken. These fungi were uninvolved from food materials such as onion, vegetable waste, wheat straw, fruits of Musa species, enjoyable potato, decaying vegetation and vegetable, respectively and were procured from Microbial Type Culture assembly (MTCC), Institute of Microbial Technology, Chandigarh, India.The MTCC code No. of these strains are 2479, 1884, 1810, 3374, 1893, 2088, 2553 and 2007, respectively. Cultures of each of the fungi were maintained on Czapek (DOX) agar medi a with adjusting pH 6. 06. 5 and slants were stored at 4 C. The antifungal natural action of the volatile oil and oleoresin against fungi were undertaken using inverted petriplate (Ramdas et al. , 1998) and poison food techniques (Amvam Zolla et al. , 1998). In inverted petriplate method, the required dose (2, 4 and 6 lL) of undiluted sample were soaked on a small piece (diameter 12 mm) of Whatmann No. 1 ? ter paper and it was kept on the lid of petriplate which is in inverted position whereas in poison food 2. 4. Complementary antioxidant assays 2. 4. 1. Antioxidant activity in linoleic acid system Antioxidant activity was carried out using the method proposed by Osawa and Namaki (1983) with small changes. Samples (1 mL) in ethanol were mixed with 2. 5% linoleic acid in ethanol (4. 1 mL), 0. 05 M phosphate bu? er (pH = 7, 8 mL) and distilled water (3. 9 mL) and kept in sack out cap containers under dark condition at 40 C. This solution (0. 1 mL) was added to the solution of 9. 7 mL of 75% ethanol and 0. mL of 30% ammonium thiocyanate. After 3 min, 0. 1 mL of 0. 02 M ferrous chloride in 3. 5% hydrochloric acid was added to the reaction mixture, the absorbance of red color was measured at 500 nm in the spectrophotometer, for e actually two days. The control and standards were subjected to the same procedure except for the control, where there was no addition of sample and for the standard 1 mL of sample was replaced with 1 mg of BHA and BHT. G. Singh et al. / feed and chemical Toxicology 45 (2007) 16501661 technique, the required dose (2, 4 and 6 lL) of the undiluted sample were mixed with the 20 mL of culture medium.Each test was replicated for three magazines and fungi toxicity was measured after 6 days in terms of percent mycelial zone inhibition. 2. 5. 2. bactericide investigations sextette pathogenic bacteria Bacillus cereus (430), Bacillus subtilis (1790), Staphylococcus aureus (3103) (gram-positive), Escherichia coli (1672), Salmonella typhi (733), genus Pseudomonas aeruginosa (1942) (gram-negative) were selected for present study. All the bacterial strains were procured from Microbial Type Culture Collection (MTCC), Institute of Microbial Technology, Chandigarh, India. They were sub cultured on nutrient agar broth (Hi-media) and stored at 4 C.Active cultures for experiments were prepared by transferring one loopful of cells from stockpile cultures to ? ask of nutrient agar broth, which were incubated without agitation for 24 h at 37 C. In order to determine the antibacterial activity of the essential oils and oleoresins, agar well di? usion method was followed. 0. 1 mL of 101 time diluted bacterial strain in ringers solution were ? ood inoculated on to the grow of well settled sterilized culture medium. The wells (10 mm diameter) were lop off from agar, and 0. 2 mL of sample (2, 4 and 6 lL of essential oil or oleoresin diluted in 1 mL of DMSO) was delivered into them.For standard, 0. 2 mL of aqueous solution of ampicillin (1 mg mLA1) was used. After incubation for 24 h at 37 C, all plates were examined for any zones of growth inhibition according to method developed by Davidson and Parish (1989). All the plates were replicated twice and the results were averaged. 2. 5. 3. statistical analysis For the oil or oleoresin, three samples were prepared for each experiment. The data were presented as mean standard deviation of three determinations (data were not shown). The quantifiable data of major components of oil and oleoresin were statistically examined by analysis of deviation (Sokal, 1973) and signi? ant di? erences among several groups of data were examined by Ducans multiple seethe test. A probability value of p 0. 05 was considered signi? banking company. elude 1 Chemical composition of cinnamon leaf volatile oil and oleoresin Compound quicksilver(a) oil MS % a-Thujene a -Pinene b-Pinene Myrcene a-Phellandrene p-Mentha-1(7),8-diene p-Cymene 1,8-Cineole Terpinolene a-Terpineol a-Cubebene E ugenol b-Caryophyllene Aromadendrene a-Amorphene Germacrene-D Bicyclogermacrene d-Cadinene Spathulenol Sabinene c-Terpinene Terpinen-4-ol d-Elemene Viridi? orol Methoxy-eugenol Isospathulenol Neophytadiene Docosane Nonacosane Vitamin-E Total 0. 1 0. tr tr 1. 9 tr 0. 7 0. 7 tr tr tr 87. 3 1. 9 1. 1 tr 0. 6 3. 6 0. 4 0. 5 99. 4% a 1653 Oleoresin KI 931 941 980 993 atomic number 67 1011 1026 1033 1088 1191 1350 1358 1420 1441 1490 1490 1496 1527 1576 MSa % 0. 3 tr tr 87. 2 1. 4 0. 8 0. 4 0. 2 1. 7 0. 6 1. 7 tr tr tr 1. 0 0. 3 0. 1 0. 3 0. 3 0. 1 0. 1 0. 2 97. 1% KI vitamin C7 1026 1191 1358 1420 1441 1490 1490 1496 1527 1576 975 1064 1177 1340 1594 3. Results and discussion 3. 1. Chemical analysis GC and GCMS analysis of cinnamon leaf volatile oil showed the presence of 19 components accounting for 99. % of the total amount (Table 1). The major component was eugenol (87. 3%) followed by bicyclogermacrene (3. 6%), a-phellanderene (1. 9%), b- carryophyllene (1. 9%), aromadendrene (1. 1%), p-cymene (0. 7%) and 1,8-cineole (0. 7%). Moreover, its oleoresin showed the presence of 25 components accounting for 97. 1% of the total amount (Table 1). The major components accounting were eugenol (87. 2%), spathulenol (1. 7%), bicyclogermacrene (1. 7%), b-caryophyllene (1. 4%) and d-elemene (1. 0%). The analysis of cinnamon bark volatile oil showed the presence of 13 components accounting for degree Celsius% of the total amount (Table 2). E)-cinnamaldehyde was found as the major component along with d-cadinene (0. 9%), a-copaene (0. 8%) and a-amorphene (0. 5%), whereas its bark oleoresin showed the presence of 17 components accounting for 92. 3% of the total amount (Table 2). The major components were (E)-cinnamaldehyde (49. 9%), coumarin (16. 6%), d-cadinene (7. 8%), a-copaene (4. 6%), (Z)-cinnamaldehyde (1. 5%), ortho-methoxy cinnamaldehyde (1. 5%) and b-bisabolene (1. 4%) along with several other compo- Percentages are the mean of three runs and were obtained from electronic integration measurements using selective mass detector tr 0. 1. a nents. Recently, Raina et al. (2001) reported eugenol (76. 6%), linalool (8. 5%) and pipertone (3. 31%) as major components from its leaf oil braggart(a) in pocket-size Andman whereas the steam distilled volatile oil of cinnamon fruit ? grown at Karnataka and Kerala consists (Simic et al. , 2004 Jayaprakash et al. , 1997) of hydrocarbons (32. 8% and 20. 8%) and oxygenated compounds (63. 7% and 73. 4%) and trans-cinnamyl acetate and b-caryophyllene were found to be major component. 3. 2. Antioxidative assays in mustard oil The changes of PV in mustard oil of all investigated samples are presented in Fig. 1.The rate of oxidative reactions in mustard oil with additives was intimately similar to that of the blank sample. The stability of the mustard oil samples to the formation of peroxides can be ranked in the following descending order interchange oleoresin BHT PG % eugenol utter oleoresin % BHA Leafoil cinnamaldehyde bark oil 1654 G. Singh et al. / diet and Chemical Toxicology 45 (2007) 16501661 Table 2 Chemical composition of cinnamon bark volatile oil and extract Compound Volatile oil MS % a-Pinene Camphene Sabinene b-Pinene Limonene 1,8-Cineole Camphor Z-cinnamaldhyde E-cinnamaldhyde a-Copaene a-Amorphene -Cadinene Terpinen-4-ol b-Caryophyllene Coumarin a-Muurolene b-Bisabolene Cadina-1(2), 4-diene Ortho-methoxy cinnamadehyde Cubenol 1-Heptadecene 1-Nonadecene Tetracosane Octacosane Nonacosane Total a a Oleoresin KI 941 953 975 980 1031 1035 1144 1225 1279 1379 1490 1527 MSa % 1. 5 50. 0 4. 6 7. 8 0. 1 1. 0 16. 6 4. 4 1. 4 1. 8 1. 5 0. 5 0. 2 0. 4 0. 1 0. 1 0. 2 92. 3% KI 1225 1279 1379 1527 1177 1420 1436 1500 1506 1530 1532 tr tr tr tr tr tr tr tr 97. 7 0. 8 0. 5 0. 9 blow% ays. The e? ects of volatile oils and oleoresins on malonaldehyde formation for mustard oil in terms of incuba tion time versus TBA value at 60 C are shown in Fig. 2. The malondehyde formation of all the additives increases with storage time. The oil showed a moderate inhibition at 0. 02% concentration, and was comparable to BHA and PG but much lower than BHT. These results were well correlated with p-anisidine and total carbonyl values (Fig. 4). However, the age is slightly di? erent as compared with the one obtained during measurements of peroxide values.For instance, bark oleoresin had a superficial greater activity for preventing the formation of secondary oxidation products than primary ones. On contrary, volatile oils were slightly less e? ective in preventing the formation of secondary oxidation products than primary ones. From the above results, it should be said that the formation of the primary oxidation species, peroxides, were also quite similar with the secondary oxidation products, and the changes of twain oxidation characteristics are in a bully correlation. Hence, the inh ibition activity of leaf and bark oleoresins were excellent among all the additives and there was a signi? ant di? erence amidst the blank and antioxidants at the P 0. 05 level. 3. 3. Antioxidant activity in linoleic acid system To evaluate the antioxidant potential of volatile oils and oleoresins of leaf and bark, their lipid repressing activities were compared with selected antioxidants and their major components by using ferric thiocyanate method of measuring the amounts of peroxides formed in emulsion during incubation. High absorbance is an indication of a high concentration of formed peroxides. The absorbance values of volatile oils and oleoresins of cinnamon along with synthetic antioxidants are shown in Fig. . The absorbance Percentages are the mean of three runs and were obtained from electronic integration measurements using selective mass detector tr 0. 01. Simultaneously with the measurements of peroxide value, the changes the secondary oxidation products such as mal onaldehyde and 2-alkenals, which are measured by thiobarbituric (Fig. 2), p-anisidine (Fig. 3) and total carbonyl values (Fig. 4), were also determined after every 7 long hundred have got BHT C. L. crude oil C. L. Oleoresin eugenol BHA PG C. B. Oil C. B. Oleoresin E-cinnamaldehyde 100 Peroxide value (meq/kg) 80 60 40 20 0 0 7 14 21 28Incubation time (days) Fig. 1. Inhibitory e? ect of volatile oil and oleoresin of cinnamon leaf and bark on the primary oxidation of mustard oil measured using peroxide value method. G. Singh et al. / Food and Chemical Toxicology 45 (2007) 16501661 1655 6 5 Control BHT Leaf oil Leaf oleoresin Eugenol BHA PG skin oil sputter oleoresin E-cinnamaldehyde TBA value (meq/g) 4 3 2 1 0 0 7 14 21 28 Incubation time (days) Fig. 2. Inhibitory e? ect of volatile oil and oleoresin of cinnamon leaf and bark on the malonaldehyde formation in mustard oil measured using TBA value method. 7 6 Control BHT C. L. Oil C. L.Oleoresin eugenol BHA PG C. B. Oil C. B. Oleores in E-cinnamaldehyde p-anisidine value 5 4 3 2 1 0 0 7 14 21 28 Incubation time (days) Fig. 3. Inhibitory e? ect of volatile oil and oleoresin of cinnamon leaf and bark on the formation of 2-alkenals in mustard oil measured using p-anisidine method. 16 14 Carbonyl value (mg) 12 10 8 6 4 2 0 7 Control BHT C. L. Oil C. L. Oleoresin Eugenol BHA PG C. B. Oil C. B. Oleoresin E-cinnamaldehyde 14 21 28 Incubation time (days) Fig. 4. Inhibitory e? ect volatile oil and oleoresin of cinnamon leaf and bark on the total carbonyls present in mustard oil. 1656 G. Singh et al. Food and Chemical Toxicology 45 (2007) 16501661 1. 9 1. 7 Absorbance at 500 nm 1. 5 1. 3 1. 1 0. 9 0. 7 0. 5 0 Control BHT Leaf oleoresin Bark oleoresin Cinnamaldehyde BHA Leaf oil bark oil eugenol 25 50 75 100 one hundred twenty-five 150 175 200 Incubation time (h) Fig. 5. Inhibitory e? ect of volatile oil and oleoresin of cinnamon leaf and bark on the primary oxidation of linoleic acid system measured using ferric thiocyan ate method. of linoleic acid emulsion without additive change magnitude rapidly, and there was a signi? patois di? erence among blank and antioxidants at the P 0. 05 level. As can be seen in this ? , bark oleoresin was most e? ective among all the additives followed by leaf oleoresin. However, there are no signi? cant (p 0. 05%) di? erences between antioxidative activities of oleoresins, oils, BHA, BHT and PG. 3. 4. DPPH and hydroxyl radical scavenging e? ects Table 6 shows the DPPH and hydroxyl radical scavenging activity of leaf and bark volatile oils and oleoresins with various concentrations. As positive control, BHA and BHT were also examined. Bark oleoresin showed the best result through all concentrations for DPPH assay. The volatile oils have shown almost equal and moderate radical scavenging activity.At a concentration of 5 lL, signi? cant di? erences in DPPH scavenging activities was observed between BHA (78. 4%), BHT (81. 2%) and oleoresins of both leaf (51. 3%) and bark (75. 6%). However, as concentration increased, the di? erences in scavenging activities between BHA, BHT and oleoresins become less signi? cant. For hydroxyl radical scavenging test AOH radicals were generated by reaction of ferric-EDTA together with H2O2 and ascorbic acid to attack the substrate deoxyribose. The resulting products of the radical attack form a pink chromogen when heated with TBA in acid solution (Ohkawa et al. , 1979 Shimada et al. 1992). When the oils or oleoresins were incubated with this reaction mixture they were able to interfere with free radical reaction and could prevent damage to the sugar. The results are shown in Table 6. At 5 lL, scavenging e? ects on hydroxyl radicals were 31. 2%, 51. 2%, 43. 6% and 57. 6% for leaf and bark volatile oils and oleoresin. However, at 25 lL BHA and BHT exhibited scavenging activities of 84. 9% and 83. 2%, respectively. There was a little change in the order of DPPH and hydroxyl radical scavenging activity of leaf oleor esin (86. 1%), bark volatile oil (79. 6%) and bark oleoresin (78. 6%).A close to linear correlation between radical scavenging activity and concentration of poly phenolic resin compounds in various vegetable and fruits have been reported (Pyo et al. , 2004 Robards et al. , 1999). These reports indicated that the radical scavenging activity of oleoresins might be mostly a? ected by position of the phenolic hydroxyl group which is present in eugenol. Yepez et al. (2001) used eugenol as standard which removed 95% of the initial DPPH free radical. 3. 5. Chelating e? ect and reducing power Chelating e? ects of the leaf and bark oleoresins on ferrous ions increased from 20. 5% at 5 lL to 24. % at 10 lL and maintained a plateau of 28. 235. 5% at 15 25lL (Fig. 6). The bark oleoresin showed a better chelating e? ect than those leaf oleoresin and both volatile oils. In addition, chelating e? ects of oleoresins were relatively parallel and increased from 20. 523. 6% at 5 lL to 38. 5 42% at 25 lL. However, at 5 lL, the chelating ability of EDTA was 90. 4%. Apparently, the cinnamon leaf and bark oleoresins could chelate ferrous ions but were not as e? ective chelators as EDTA. Reducing powers of leaf and bark oleoresins of cinnamon were excellent and were in the range 56. 058. 4, comparable with that of BHA (63. ) and BHT (65. 2) at 5 lL (Fig. 7). However, at 25 lL, the reducing power of the leaf and bark oleoresins, BHA and BHT were comparable (78. 587. 9). The reducing powers of the oleoresins might be due to the hydrogen donating abilities (Shimada et al. , 1992). 3. 6. Antimicrobial studies The results of volatile oils and oleoresins of cinnamon leaf and bark by inverted petriplate and poison food tech- G. Singh et al. / Food and Chemical Toxicology 45 (2007) 16501661 1657 100 90 Chelating effect (%) 80 70 60 50 40 30 20 10 0 0 EDTA Leaf oleoresin Bark oleoresin E-Cinnamaldehyde Leaf oil Bark oil Eugenol 10 15 20 25 30 Concentration ( L) Fig. 6. Chelating e? ect of vol atile oil and oleoresin of cinnamon leaf and bark along with synthetic antioxidants. 100 Reducing power (%) 80 BHA Leaf oil Bark oil Eugenol BHT Leaf oleoresin Bark oleoresin Cinnamaldehyde 60 40 20 0 5 10 15 20 25 30 Concentration ( L) Fig. 7. Reducing power of volatile oil and oleoresin of cinnamon leaf and bark along with synthetic antioxidants. niques are reported in Tables 3 and 4, respectively. using inverted petriplate method (Table 3), the leaf volatile oil was found to be 100% antifungal against all the tested fungi except A. chraceus and A. terreus at 6 lL. It was interesting to note that complete inhibition against A. ?avus was obtained just at 2 lL. However, leaf oleoresin has shown complete mycelial zone inhibition save for P. citrinum. More than 75% activity was obtained for P. veridicatum, F. moniliforme and A. ?avus. Bark volatile oil has shown complete inhibition against the fungi such as F. gramenearum, F. moniliforme, P. citrinum, P. viridicatum and A. terreus at 6 lL. Using poison food technique (Table 4), leaf volatile has caused complete inhibition against all the tested fungi except P. itrinum whereas oleoresin has caused complete inhibition only against P. citrinum. Bark volatile oil has shown complete inhibition against almost all the tested fungi except for A. ?avus, A. ochraceus whereas its oleoresin has caused complete inhibition for A. ?avus and A. ochraceus along with A. niger, A. terreus, P. citrinum and P. viridicatum at 6 lL. Using agar well di? usion method (Table 5), leaf volatile oil has shown better results in comparison with oleoresin and commercial bactericide, i. e. , ampicillin. Complete mycelial zone inhibition was obtained using leaf volatile oil against P. eruginosa and B. cereus. However, it has moderate inhibitory e? ect on B. subtilis and S. aureus whereas its oleoresin has shown almost 100% activities against S. typhi and B. cereus. Bark volatile oil has been found to be better than bark oleoresin as it has c aused more than 50% inhibition against all the tested fungi. There are several reports (Singh et al. , 1995 Hili et al. , 1997) stating that C. zeylanicum Blume exhibit antimicrobial activity. Their results demonstrate that the leaf oil completely inhibit the growth of E. coli, S. aureus and P. aeruginosa at the 1658 G. Singh et al. Food and Chemical Toxicology 45 (2007) 16501661 Table 3 Antifungal activity of volatile oils and oleoresins of cinnamon leaf and bark by inverted petriplate method Test process (lL) Percent mycelial inhibition zonea AN Leaf volatile oil 2 4 6 2 4 6 2 4 6 2 4 6 2 4 6 2 4 6 91. 5 100 100 25. 0 50. 0 58. 7 85. 3 93. 1 100 6. 3 38. 7 87. 2 62. 5 100 100 6. 3 35. 1 78. 3 AF 100 100 100 45. 6 76. 3 89. 3 100 100 100 6. 3 8. 8 13. 8 81. 2 100 100 65. 3 93. 2 100 AO 18. 7 56. 3 87. 5 46. 3 56. 3 68. 7 15. 6 52. 8 85. 3 12. 5 25. 0 37. 5 54. 3 78. 7 100 12. 5 25. 0 30. 8 FG 50. 0 52. 5 100 37. 5 50. 56. 3 36. 3 45. 8 95. 2 87. 5 87. 5 100 25. 0 50. 0 58. 7 75. 0 87. 5 100 FM 50. 0 52. 5 100 57. 5 80. 0 92. 5 31. 2 43. 2 83. 6 75. 0 87. 5 100 58. 6 79. 5 83. 3 58. 7 75. 3 83. 8 PC 37. 5 56. 3 100 67. 8 93. 3 100 25. 5 45. 8 86. 3 100 100 100 100 100 100 100 100 100 PV 37. 5 56. 3 100 38. 9 65. 5 87. 5 28. 5 47. 3 93. 7 100 100 100 76. 5 87. 5 100 85. 5 91. 5 100 AT 18. 7 36. 5 75. 0 46. 3 56. 3 68. 7 41. 3 53. 2 69. 1 37. 5 56. 3 100 87. 5 94. 1 100 56. 3 85. 6 100 Leaf oleoresin Eugenol Bark volatile oil Bark oleoresin E-cinnamaldehyde AN = Aspergillus niger AF = Aspergillus ? vus AO = Aspergillus ochraceus FG = Fusarium graminearum FM = Fusarium moniliforme PC = Penicillium citrinum PV = Penicillium viridicatum AT = Aspergillus terreus. a comely of three replicates. Table 4 Antifungal activity of volatile oils and oleoresins of cinnamon leaf and bark by food poisoned method Test Dose (ppm)a Percent mycelial inhibition zonea AN Leaf volatile oil 2 4 6 2 4 6 2 4 6 2 4 6 2 4 6 2 4 6 kilobyte 2000 3000 100 100 100 62. 5 77. 5 87. 5 100 100 100 73. 5 100 100 48. 9 65. 3 83. 6 52. 3 68. 7 72. 3 78. 2 82. 2 96. 3 AF 31. 3 87. 5 100 18. 8 50. 0 100 15. 6 63. 2 95. 6 () 51. 3 87. 5 88. 7 91. 3 100 52. 87. 6 91. 2 85. 3 91. 2 96. 2 AO 50. 0 100 100 35. 0 82. 5 97. 5 45. 6 95. 6 100 75. 0 81. 2 100 100 100 100 100 100 100 84. 2 91. 2 98. 4 FG 75. 0 100 100 62. 5 77. 5 87. 5 63. 5 82. 1 93. 8 50. 0 75. 0 87. 5 65. 3 83. 2 100 47. 2 67. 8 85. 3 90. 2 96. 3 94. 5 FM 100 100 100 38. 7 46. 3 78. 7 45. 6 53. 6 78. 3 75. 0 83. 2 100 48. 7 56. 3 78. 7 63. 2 65. 8 87. 1 97. 2 100 100 PC 50. 0 75. 0 87. 5 35. 0 62. 5 97. 5 48. 6 73. 1 82. 6 43. 7 51. 3 65. 0 100 100 100 85. 2 89. 7 91. 2 100 100 100 PV 87. 5 100 100 50. 0 65. 5 70. 0 73. 2 85. 6 93. 6 50. 0 75. 0 87. 5 60. 0 85. 3 100 55. 3 63. 1 91. 2 100 100 100 AT 18. 7 50. 0 56. () 50. 0 100 15. 5 50. 0 75. 2 32. 5 45. 0 76. 3 35. 0 76. 2 83. 7 42. 3 45. 6 89. 3 98. 5 100 100 Leaf oleoresin Eugenol Bark volatile oil Bark oleoresin E-cinnamaldehyde Carbendazimb AN = Aspergillus nig er AF = Aspergillus ? avus AO = Aspergillus ochraceus FG = Fusarium graminearum FM = Fusarium moniliforme PC = Penicillium citrinum PV = Penicillium viridicatum AT = Aspergillus terreus. a Average of three replicates. b sedimentary solution was used. G. Singh et al. / Food and Chemical Toxicology 45 (2007) 16501661 Table 5 Antibacterial activity of volatile oils and oleoresins of cinnamon leaf and bark by agar well di? sion method Test Concentration (ppm) Inhibition zone (mm)a guanine (+) bacteria Bs Leaf volatile oil 1000 2000 3000 1000 2000 3000 1000 2000 3000 1000 2000 3000 1000 2000 3000 1000 2000 3000 1000 2000 3000 17. 1 0. 4 20. 0 0. 6 32. 6 1. 2 14. 6 1. 2 19. 0 0. 2 25. 4 0. 8 14. 3 0. 6 17. 0 0. 3 29. 6 1. 2 14. 2 0. 5 18. 3 0. 3 26. 7 0. 7 16. 2 1. 3 20. 2 1. 1 25. 3 0. 3 12. 3 0. 1 17. 3 0. 5 23. 7 0. 6 32. 5 1. 2 34. 3 0. 3 41. 2 0. 2 Sa 26. 1 1. 5 34. 9 1. 3 48. 7 0. 5 27. 1 0. 1 38. 9 0. 2 49. 3 2. 2 23. 1 1. 1 26. 9 1. 3 38. 7 0. 3 27. 0 0. 9 44. 6 0. 56. 7 0. 1 23. 1 0. 4 28. 7 0. 2 33. 6 0. 3 23. 0 0. 7 41. 6 0. 8 53. 7 0. 1 29. 5 0. 6 32. 6 1. 6 37. 5 0. 2 Bc 43. 3 1. 7 58. 0 0. 6 + 64. 5 0. 6 80. 4 1. 1 + 33. 3 1. 5 56. 0 0. 8 72. 3 0. 2 41. 3 1. 7 52. 6 1. 2 56. 3 0. 5 38. 6 0. 2 41. 3 0. 4 45. 6 0. 7 31. 3 1. 2 48. 6 0. 2 52. 3 0. 3 31. 4 0. 2 34. 6 0. 1 38. 2 0. 3 Gram (A) bacteria Ec 13. 0 0. 2 18. 2 1. 1 25. 8 0. 5 11. 4 0. 6 13. 1 0. 7 18. 5 1. 1 11. 3 0. 1 17. 2 1. 6 21. 8 0. 3 28. 1 0. 2 33. 2 1. 3 35. 1 0. 3 33. 4 0. 5 35. 4 0. 3 37. 1 0. 3 26. 1 0. 5 33. 1. 8 34. 1 0. 2 33. 6 0. 8 37. 8 1. 4 39. 5 0. 6 St 12. 5 0. 8 14. 6 1. 1 17. 9 0. 2 53. 6 1. 3 73. 8 0. 5 78. 1 0. 8 12. 5 0. 8 14. 6 1. 1 17. 9 0. 2 20. 6 1. 8 32. 7 2. 0 41. 3 0. 3 17. 2 0. 1 18. 6 0. 7 19. 3 0. 5 18. 6 1. 4 31. 7 1. 0 40. 3 0. 3 21. 9 0. 5 25. 6 0. 7 28. 9 1. 3 Pa 1659 25. 7 0. 6 + + 20. 5 0. 1 21. 4 0. 8 25. 8 0. 1 26. 7 0. 5 + + 50. 2 1. 2 56. 5 0. 8 60. 2 0. 3 40. 6 0. 4 45. 3 0. 8 56. 2 0. 7 30. 2 1. 1 48. 5 0. 6 59. 2 0. 1 24. 3 0. 4 26. 3 1. 5 27. 3 1. 1 Leaf oleoresin Eugenol Bark volatile oilBark oleoresin E-cinnamaldehyde Ampicillin Bs = Bacillus subtilis Sa = Staphylococcus aureus Bc = Bacillus cereus Ec = Escherichia coli St = Salmonella typhi Pa = Pseudomonas aeruginosa. (+) indicates complete inhibition. a Average of three replicates. level of 500 lg mLA1. Another report (Smith-Palmer et al. , 1998) found the MICs of C. zeylanicum against E. coli and S. aureus were 0. 05% and 0. 04%, respectively. To con? rm the relationship of the constituents in cinnamon leaf and bark and antimicrobial activity, the major components were tested for antimicrobial activity. The results are shown in Tables 35.Among both constituents, E-cinnamaldehyde possessed better activity and these ? ndings are quite similar with the results of Chang et al. (2001). However, eugenol, in spite of being phenolic compound, failed to inhib it the fungal growth by inverted petriplate method but when it was added directly to the growth media in higher concentrations, it appeared to inhibit completely the microbial growth. Nevertheless, it is worth noting that essential oils and oleoresins are very heterogeneous mixtures of a single substances, biological actions are primarily due to these components in a very complicated concert of synergistic or antagonistic e? cts. Table 6 Comparison of scavenging e? ects of cinnamon leaf and bark volatile oils and oleoresins against DPPH and hydroxyl radicals Sample Radical scavenging activitya (%) DPPH radical 5 lL Leaf oil Leaf oleoresin Eugenol Bark oil Bark oleoresin E-cinnamaldehyde BHA BHT a Hydroxyl radical 15 lL 69. 9 74. 1 65. 2 76. 2 89. 3 72. 3 92. 1 89. 2 20 lL 72. 1 76. 7 71. 3 82. 1 91. 2 75. 1 94. 7 91. 7 25 lL 73. 9 91. 2 92. 9 83. 6 95. 3 78. 3 96. 4 94. 9 5 lL 31. 2 43. 6 39. 4 51. 2 57. 6 49. 8 71. 3 66. 2 10 lL 55. 7 57. 1 45. 1 57. 6 62. 3 53. 6 75. 1 72. 1 15 lL 63. 5 70. 4 54. 3 73. 1 68. 9 57. 1 78. 75. 3 20 lL 68. 1 73. 6 61. 5 76. 9 71. 2 65. 2 81. 7 77. 5 25 lL 72. 2 86. 1 68. 2 79. 6 78. 6 68. 3 84. 9 83. 2 10 lL 58. 7 58. 9 56. 8 73. 5 87. 5 68. 1 89. 3 85. 1 45. 2 51. 3 41. 3 71. 1 75. 6 65. 3 78. 4 81. 2 Average of three replicates. 1660 G. Singh et al. / Food and Chemical Toxicology 45 (2007) 16501661 Chang, S. T. , Chen, P. F. , Chang, S. C. , 2001. 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