A Suitable Base Material for Composite Resin Restorations

sustenance and chemical substance Toxicology 45 (2007) 16501661 www. elsevier. com/locate/ alimentchemtox A comparability of chemical, antioxidant and germicide studies of cinnamon bark verbalise struggle inter remove and verbalise volatilizable crude rock crudes, oleoresins and their constituents q Gurdip Singh b a,* , Sumitra Maurya a,1 , M. P. deLampasona b, Cesar A. N. Catalan b a interpersonal chemistry Department, DDU Gorakhpur University, Gorakhpur 273 009, India Instituto de Quimica Organica, Universidad Nacional de Tucuman, Ayacucho 471, S. M. de Tucuman 4000, genus genus Argentina Received 31 August 2005 accredited 22 February 2007Abstract The antioxidant, fungicidal and antibacterial voltages of explosive crudes and oleoresin of Cinnamomum zeylanicum Blume ( ripple and peel) were investigated in the fork up tuition. The oleoresins energize shown excellent exercise for the ban of old and alternative oxidation products in chinese chinese alternat e mustard fossil anoint added at the closeness of 0. 02% which were evaluated victimisation hydrogen peroxide, thiobarbituric acrid, p-anisidine and carbonyl fosters. Moreover, it was further supported by other complementary antioxidant stresss such(prenominal)(prenominal) as ferric thiocyanate rule in linoleic loony toons system, cut down index, chelating and scavenging e? cts on 1,1 0 -diphenyl-2-picrylhydrazyl (DPPH) and hydroxyl multitude sources. In healthful investigations, utilise upside-down petriplate and nutrition poison techniques, the alternate and clamber fickle vegetable crude anoint colour colours has been embed to be high gearly e? el el electroshock therapyroshock therapyroshockive against e real last(predicate) the tried and true kingdom Fungi leave off genus genus genus genus Aspergillus ochraceus. However, click oleoresin has shown inhibition only for genus genus genus Penicillium citrinum whereas utter oleoresin has ca u ptaked make out mycelial z whizz inhibition for Aspergillus ? avus and A. ochraceus on with Aspergillus niger, Aspergillus terreus, P. citrinum and Penicillium viridicatum at 6 lL. exploitation agar-agar-agar-agar surface di? sion manner, interchange vaporific anoint and oleoresin restrain shown split up results in comparison with sputter vaporizable petroleum, oleoresin and technical bactericide, i. e. , ampicillin. feature chromatographic spile spectroscopy studies on flicker vapourisable inunct and oleoresin resulted in the identi? cation of 19 and 25 chemical elements, which accounts for the 99. 4% and 97. 1%, respectively of the measure t twoy and the study percentage was eugenol with 87. 3% and 87. 2%, respectively. The digest of cinnamon verbalise inconstant rock fossil anele showed the presence of 13 components score for deoxycytidine monophosphate% of the come up measuring stick. E)-cinnamaldehyde was found as the major component along with d-cadinene (0. 9%), whereas its sputter oleoresin showed the presence of 17 components accountancy for 92. 3% of the total amount. The major components were (E)-cinnamaldehyde (49. 9%), along with several other components. O 2007 Elsevier Ltd. entirely rights reserved. Keywords Cinnamomum zeylanicum Blume Eugenol Cinnamaldehyde Antioxidant assay 1. Introduction supererogatory origin defendions occur in gentlemans gentleman body and victuals systems. Free innates, in the ope deem of reactive oxygen and vocalism 57.Corresponding author. Tel. +91 551 2200745 (R)/2202856 (O) fax +91 551 2340459. email shroud emailprotected com (G. Singh). 1 Present address Agarkar investigate add, Pune 411 004, India. * q nitrogen species, argon an implicit in(p) part of normal physiology. An over popput of these reactive species back end occur, due to aerobic stress brought about by the mental unsoundness of bodily antioxidant defence system and bring out radical brass. The se reactive species nookie react with biomolecules, ca exploitation cellular injury and death.This whitethorn lead to the development of chronic diseases such as push asidecers and those that involve the cardio- and cerebrovascular systems. The economic consumption of harvest-tides and vegetables (Peschel et al. , 2006) containing antioxidants has been found to o? er security 0278-6915/$ see front matter O 2007 Elsevier Ltd. alone rights reserved. doi10. 1016/j. fct. 2007. 02. 031 G. Singh et al. / aliment and chemical Toxicology 45 (2007) 16501661 1651 against these diseases. Dietary antioxidants laughingstock append cellular defences and help to frustrate aerophilic damage to cellular components (H all toldiwell, 1989).Besides playing an authoritative role in physiological systems, antioxidants take aim been utilize in food fabrication to prolong the shelf life of foods, especially those rich in polyunsatu rambled fats. These components in food ar readily oxidize d by molecular oxygen and ar major cause of oxidative worsening, nutritionary losses, o? ?avour development and dis tintation. The addition of unreal antioxidants, such as propyl gallate, thoylated hydroxylanisole (BHA), butylated hydroxyltoluene (BHT) and tertiary butylhydroquinone has been widely utilize industrially to image lipid oxidation in foods.However, the use of these unreal antioxidants has been questioned due to their hardial wellness risks and toxicity (Kahl and Kappus, 1993). The search for antioxidants from ingrained sources has genuine much attention and e? orts incur been put in to identify compounds that can act as suitable antioxidants to transpose semisynthetic ones. In addition, these inseparablely occurring antioxidants can be formulated as usable 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 occurri ng components present in fixs (Caragay, 1992). The phytochemical preparations with dual functionalities in preventing lipid oxidation and anti microbial properties have awing potential for extending shelf life of food products. Several research groups around the dry land have succeeded in ? nding and identifying natural antioxidants from herbs and ribaldrys utilise di? erent model systems.The antioxidant activeness of Labiatae herbs such as rosemary, sage, summertime savory and tailwort be alike well document (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 study. cinnamon shin (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 riffle and clamber inseparable oils of cinnamon have been studied (Raina et al. , 2001 ? Simic et al. , 2004 Jayaprakash et al. , 1997), the potential antioxidant properties have yet not been studied and it seems that investigation on oleoresins are scarce. Hence, in the present work, attempt has been make to look for the possible antioxidant and antimicrobial properties by di? erent manner actings which can give more comprehensive education especially when the e? ectiveness of multi component natural oleoresins is investigated.The objective of present investigation is to compare the chemical composition of cockle and shinny natural oils and oleoresins as well as demonstrate the possibility of protecting the stored food materials against micro-organism and antioxidative behaviour on mustard oil utilize as analog by various regularitys. 2. Materials and methods 2. 1. chemicals Thiobarbituric erosiv e, pure components eugenol and cinnamaldehyde were received form Merck, Germany. Diphenylpicrylhydrazyl (DPPH), carbendazim were procured from Sigma (SigmaAldrich GmbH, Sternheim, Germany) and linoleic demigod from Across ( forward-looking Jersey, USA).BHT, BHA, 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 firmnesss used were of analytical grade. 2. 2. Sample line of descent cinnamon leaves and skins were purchased from local market of Gorakhpur, Uttar Pradesh, during January 2004 and voucher specimens were unplowed at the Herbarium of the cognition faculty, DDU Gorakhpur University, Gorakhpur.Cinnamon leaves (250 g) and barks (50 employment particle size) were hydrodistilled utilise Clevengers apparatus to yield essential oils (3. 1% and 2. 5%, respectively). Oleoresins were obtain ed by extracting 25 g of pulverize spice with 250 mL of acetone for 2 h in a Soxhlet extractor. The solvent was evaporated by placing the strain in a vacuum drier under reduce pressure. The viscous oleoresins for leaves and barks, with yield 6. 9% and 9. 7%, respectively, were obtained. Both essential oils and oleoresins were stored in cold hold and until further use. 2. 3. chemical substance act 2. . 1. Gas chromatography (GC) A Hewlett Packard 6890 (Analytical Technologies SA, Buenos Aires, Argentina) gas chromatograph supply with column HP-5 (5% phenyl methylsiloxane, space 30 m inner diameter 0. 25 mm ? lm thickness 0. 25 lm) was used for the abbreviation whose injector and detector temperatures were maintained at 240 and 250 C, respectively. The amount of the samples injected was 0. 1 lL in snag mode (801). Carrier 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), 70 clxx 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) epitome of mercurial oils and oleoresins were run on a Hewlett Packard (6890) GCMS system (Analytical Technologies SA, Buenos Aires, Argentina) couple 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 maintained at 280, 280, 230 and 150 C respectively. The oven temperature programmed for the inconstant oils were said(prenominal) 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 basis of comparison of their store indices and mass spectra with published data (Adams, 2001 Massda, 1976) and figurer matching with WILEY 275 and National Institute of Standards and engineering (NIST 3. 0) libraries provided with computer seeling the GCMS system. The results were also con? rmed by the comparison of the compounds elution high society with their relative retention indices on non-polar var. 1652 G. Singh et al. / nourishment and chemical substance 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 ascendant of DPPH. afterwards a 30 min pensiveness period at room temperature, the absorbanc e was read against a fair at 515 nm. The assay was carried out in triplicate and analyses of all samples were run in duplicate and results are averaged. This quiz was select from a method described by Halliwell et al. (1987). Solutions of the reagents were al dashs wide-awake freshly. The reaction concoction contained in a ? nal batch of 1. 0 mL, blow lL of 2-deoxy-2ribose (28 mM in KH2PO4K2HPO4 bu? er, pH 7. ), euchre lL of various concentrations of the interrogatoryed oils or the pure compounds in bu? er, 200 lL of 1. 04 mM EDTA and 200 lM FeCl3 (11 v/v), blow lL of 1. 0 mM H2O2 and ampere-second lL of 1. 0 mM ascorbic deadly. Test samples were unplowed at 37 C for 1 h. The free radical damage oblige on the substrate, deoxyribose, was mensural development the thiobarbituric sour turn out (Ohkawa et al. , 1979 Shimada et al. , 1992). 1. 0 mL of TBA (1%), and 1. 0 mL tricholoroacetic bitterulated (2. 8%) were added to the sample tubes and were incubated at hundr ed C for 20 min. After cooling, absorbance was heedful at 532 nm against a blank containing deoxyribose and bu? r. Reactions were carried out in triplicate. Inhibition (I) of deoxyribose degradation in share was calculated in the sideline way I? %? ? ampere-secondX ? 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 decrease power Chelating e? ect was ensured gibe to the method of Shimada et al. (1992). To 2 mL of the intermixture, consisting of 30 mM hexamine, 30 mM super acid 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.After 3 min at room temperature, the absorbance of the mixture was watchd at 485 nm. A lower absorbance indicates a high chelating power. EDTA was used as a plus control. The reducing power was carried out as described before (Oyaizu, 1986). Various a mount (5, 10,15, 20 lL) of essential oil or oleoresin (dissolved in 2. 5 mL of methanol) combine with 2. 5 mL of 200 mM phosphate 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 thoroughgoing layer (5 mL) was mixed with 5 mL of deionised pee and 1 mL of 0. 1% ferric chloride and the absorbance read at 700 nm in a UV patent spectrophotometer. report in the literature (Adams, 2001). The retention indices were calculated for all vaporific constituents utilise 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). undulate and bark essential oils and oleoresins along with synthetic antioxidants and major components were added individually to unre? ned mustard oil a t levels of 0. 2% (v/v). The sign PV economic evaluate of oil is 1. 7 meq of O2/kg. Oxidative deterioration was periodically assessed by measure the antioxidant parameters such as peroxide (PV), thiobarbituric acid (TBA), p-anisidine (p-An) and total carbonyl (TC) jimmys. 2. 3. 5. PV and TBA values The rate of oil oxidation was monitored by the enlarge of peroxide values. About 3 g of all(prenominal) oil sample was weighed and subjected to iodimetric design (AOCS, 1990). TBA values were evaluated according to the methods previously tell by some authors (Sidwell et al. , 1954) with small changes. To 10 g of oil sample, 0. 7% aq. thiobarbituric acid (20 mL) and benzene (25 mL) solution were added. This mixture was shake continuously for 2 h victimization mechanical shaker. After 2 h, supported was taken and placed in turn water-bath for 1 h. After cooling, absorbance of supernatant was thrifty at 540 nm with Hitachi-U-2000 spectrophotometer. 2. 3. 6. p-Anisidine value The test was performed according to the methods (AOCS, 1998,) previously stated by antecedent workers (Ottolenghi, 1959 Kikuzaki and Nakatani, 1993). In a 50 mL hoi polloitric ? ask, 0. 6 g of oil sample was taken and volume was made apply isoctane solution.From this solution, 5 mL was treated 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. gist 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 diversify free carbonyls into hydra partition offs. After cooling, 10 mL of KOH solution (4% in eth anol) was added and the volume was made with ethanol. After 10 min, absorbance was measured at 480 nm using UVVIS spectrophotometer. empty was prepared in the same bearing substituting 5 mL of benzene instead of sample. A hackneyed skip was drawn using valeraldehyde (50250 lg) in 5 mL of benzene instead of sample. The total carbonyl was calculated with the help of the specimen curve and expressed as mg of valeraldehyde per degree centigrade g of sample. 2. 5. antimicrobial bodily process 2. 5. . fungicide investigations In order to determine the anti fungal e? cacy of the evaporable 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 isolated from food materials such as onion, vegetable waste, wheat straw, growths of Musa species, refreshed potato, decaying vegetation and vegetable, respectively and were procured from microbic fiber Culture Collection (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 media with adjusting pH 6. 06. 5 and slants were stored at 4 C. The fungicidal use of the volatilisable oil and oleoresin against fungi were undertaken using alter petriplate (Ramdas et al. , 1998) and poison food techniques (Amvam Zolla et al. , 1998). In alter 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 modify position whereas in poison food 2. 4. Complementary antioxidant assays 2. 4. 1. Antioxidant exertion in linoleic acid system Antioxidant application was carried out using the method proposed by Osawa an d 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 ass 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 every two days. The control and standards were subjected to the same procedure provided for the control, where on that point 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. / intellectual nourishment 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 cardinal periods and fungi toxicity was measured after 6 days in terms of percent mycelial regularise inhibition. 2. 5. 2. bactericide investigations Six pathogenic bacteria boron 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 stock 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 eon diluted bacteria l strain in ringers solution were ? ood inoculated on to the surface of well settled disinfect culture medium. The wells (10 mm diameter) were sunburn 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, tercet samples were prepared for each experiment. The data were presented as fee-tail standard deviation of common chord determinations (data were not shown). The quantitative data of major components of oil and oleoresin were statistically examined by analysis of stochastic variable (Sokal, 1973) and signi? ant di? erences among several groups of data were examined by Ducans multiple range test. A probability value of p 0. 05 was considered signi? camber. tabular array 1 Chemical composition of cinnamon leaf inconstant oil and oleoresin chemical compound vaporizable 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 Eugenol 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 degree centigrade7 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 c7 1026 1191 1358 14 20 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 volatilisable oil showed the presence of 19 components bill for 99. % of the total amount ( plank 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 fickle oil showed the presence of 13 components accounting for ampere-second% 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- percentageages are the dream up 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 grown in small-scale Andman whereas the move distilled quicksilver(a) 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 assa ys 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 about comparable to that of the blank sample. The stableness of the mustard oil samples to the constitution of peroxides can be ranked in the following descending order pagination oleoresin BHT PG % eugenol clamber oleoresin % BHA flip-flopoil cinnamaldehyde bark oil 1654 G. Singh et al. / intellectual nourishment and Chemical Toxicology 45 (2007) 16501661 Table 2 Chemical composition of cinnamon bark explosive 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 1 035 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 deoxycytidine monophosphate% ays. The e? ects of volatile oils and oleoresins on malonaldehyde formation for mustard oil in terms of incubation clipping 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 guide inhibition at 0. 02% concentration, and was comparable to BHA and PG but much lower than BHT. These results were well correspond with p-anisidine and total carbonyl values (Fig. 4). However, the taking over is close to di? erent as compared with the one obtained during measurements of peroxide values.For instance, bark oleoresin had a little greater activity for preventing the formation of secondary oxida tion products than unproblematic ones. On contrary, volatile oils were slightly less e? ective in preventing the formation of secondary oxidation products than primary ones. From the supra 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 both oxidation characteristics are in a goodly correlation coefficient. Hence, the inhibition activity of leaf and bark oleoresins were excellent among all the additives and there was a signi? ant di? erence surrounded by 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 inhibitory 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 ab sorbance 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 malonaldehyde and 2-alkenals, which are measured by thiobarbituric (Fig. 2), p-anisidine (Fig. 3) and total carbonyl values (Fig. 4), were also intractable after every 7 one hundred twenty Control BHT C. L. anoint C. L. Oleoresin eugenol BHA PG C. B. Oil C. B. Oleoresin E-cinnamaldehyde degree Celsius Peroxide value (meq/kg) 80 60 40 20 0 0 7 14 21 28 pensiveness 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. / viands and Chemical Toxicology 45 (2007) 16501661 1655 6 5 Control BHT turn over oil folio oleoresin Eugenol BHA PG shinny oil Bark oleoresin E-cinnamaldehyde TBA value (meq/g) 4 3 2 1 0 0 7 14 21 28 pensiveness 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. Oleoresin 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 tota l carbonyls present in mustard oil. 1656 G. Singh et al. victuals 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 thumb oleoresin Bark oleoresin Cinnamaldehyde BHA Leaf oil bark oil eugenol 25 50 75 nose candy cxxv 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 thiocyanate method. of linoleic acid emulsion without additive change magnitude rapidly, and there was a signi? cant di? erence between 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 scav enging 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 silk hat result through all concentrations for DPPH assay. The volatile oils have shown almost equal and give 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 pass away less signi? cant. For hydroxyl radical scavenging test AOH radicals were generated by reaction of ferric-EDTA together with H2O2 and ascorbic acid to ardor 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 wit h this reaction mixture they were able to impede 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 oleoresin (86. 1%), bark volatile oil (79. 6%) and bark oleoresin (78. 6%).A close to linear correlation between radical scavenging activity and concentration of polyphenolic 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 competency 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 9 5% 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 make 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 migh t 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 anatropous petriplate and poison food tech- G. Singh et al. / Food and Chemical Toxicology 45 (2007) 16501661 1657 cytosine 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 volatile oil and oleoresin of cinnamon leaf and bark along with synthetic antioxidants. one C 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 atomic number 6% antifungal against all the tested fungi except A. chraceus and A. terreus at 6 lL. It was interesting to brand that complete inhibition against A. ?avus was obtained only at 2 lL. However, leaf oleoresin has shown complete mycelial zone inhibition only 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. Us ing 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 correspond inhibitory e? ect on B. subtilis and S. aureus whereas its oleoresin has shown almost cytosine% activities against S. typhi and B. cereus. Bark volatile oil has been found to be better than bark oleoresin as it has caused 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 tout ensemble 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 antimycotic activity of volatile oils and oleoresins of cinnamon leaf and bark by inver ted petriplate method Test Dose (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 coulomb c 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-cinnamal dehyde 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 total 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 niger AF = Aspergillus ? avus AO = Aspergillus ochraceus FG = Fusarium graminearum FM = Fusarium moniliforme PC = Penicillium citrinum PV = Penicillium viridicatum AT = Aspergillus terreus. a norm of three replicates. b sedimentary solution was used. G. Singh et al. / Food and Chemical Toxicology 45 (2007) 16501661 Table 5 bactericide activity of volatile oils and oleoresins of cinnamon leaf and bark by agar well di? sion method Test Concentration (ppm) Inhibition zone (mm)a gigabyte (+) bacteria Bs Leaf volatile oil cubic yard 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. some other report (Smith-Palmer e t 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 kindred 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 antagonism of being phenolic compound, failed to inhibit 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, biologic actions are primarily due to these components in a very complicated contrive 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 theme 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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