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J. Agric. Food Chem. 2004, 52, 3292−3296
Chemical Constituents, Antifungal and Antioxidative Effects of Ajwain Essential Oil and Its Acetone Extract
GURDIP SINGH,*,† SUMITRA MAURYA,† C. CATALAN,‡
Chemistry Department, D.D.U. Gorakhpur University, Gorakhpur-273009, India, and Instituto de Quimica, Organica Universidad Nacinal de Tucuman, Ayacucho 471, S.M. de Tucuman 4000, Argentina
GC and GC-MS analysis of ajwain essential oil showed the presence of 26 identified components which account for 96.3% of the total amount. Thymol (39.1%) was found as a major component along with p-cymene (30.8%), γ-terpinene (23.2%), β-pinene (1.7%), terpinene-4-ol (0.8%) whereas acetone extract of ajwain showed the presence of 18 identified components which account for 68.8% of the total amount. The major component was thymol (39.1%) followed by oleic acid (10.4%), linoleic acid (9.6%), γ-terpinene (2.6%), p-cymene (1.6%), palmitic acid (1.6%), and xylene (0.1%). Moreover, the oil exhibited a broad spectrum of fungitoxic behavior against all tested fungi such as Aspergillus niger, Aspergillus flavus, Aspergillus oryzae, Aspergillus ochraceus, Fusarium monoliforme, Fusarium graminearum, Pencillium citrium, Penicillium viridicatum, Pencillium madriti, and Curvularia lunata as absolute mycelial zone inhibition was obtained at a 6-µL dose of the oil. However, the acetone extract showed better antioxidative activity for linseed oil as compared with synthetic antioxidants such as butylated hydroxyl toluene and butylated hydroxyl anisole.
KEYWORDS: Trachyspermum ammi (L.); antioxidant; antifungal; thymol; acetone extract; Aspergillus;
Ajwain, Trachyspermum ammi (L.) Sprague, is an erect annual herb with striate stem, originated in eastern regions of Persia and India. The most utilized part of ajwain is the small carawaylike fruit, which is particularly popular in Indian savory recipies, savory pastries, and snacks. In Ayurvedic medicines, it is used as a medicinal plant for its antispasmodic, stimulant, tonic, and carminative properties (1). Aroma chemicals present in spices have wide application in aromatherapy since ancient times suggesting that they have some beneficial health effects in addition to pleasant flavor (2). Furthermore, they inhibit (35) other undesirable changes in food affecting its nutritional quality, flavor, and texture. However, due to possible toxicological (6, 7) side effects of synthetic food additives on human health, the general trend toward reducing the use of synthetic food additives resulted in an expansion of the search for natural substances (8-11) possessing antimicrobial and antioxidant properties and hence they are valuable in preventing cellular damage, the cause of aging, and human diseases. For this purpose, essential oils and extracts are widely used globally because it has a complex composition, containing constituents of mostly hydrocarbons and oxygenated compounds. On the basis of this background, many studies are in progress (12* To whom correspondence should be addressed. Tel.: 91-551-2200745 (R) 2202856 (O). Fax: 91-551-2340459. E-mail: email@example.com. † Gorakhpur University. ‡ Organica Universidad Nacinal de Tucuman.
15). In literature, there are many reports available on chemical composition and antimicrobial studies (16-22) of volatile oil of ajwain. However, the anti- oxidative properties of its volatile oil and acetone extract seem not to have been reported before. As a part of our ongoing research program (20-24), chemical constituents and antifungal and antioxidative studies of volatile oil and acetone extract used as a natural food additive have been undertaken. The objective of present investigation is to compare the chemical composition of volatile oil and its extract as well as to determine the antifungal and antioxdative behavior on linseed oil using as additive by various methods.
MATERIALS AND METHODS Plant Material. Fruits of ajwain were purchased from the local market of Gorakhpur during April, and voucher specimens were deposited at the Herbarium of the Science Faculty of DDU Gorakhpur University, Gorakhpur. Extraction of the Essential Oil. The fruits of ajwain were powdered (800 mesh size) using domestic model mixi and were subjected to hydrodistillation in a Clevenger type apparatus for 6 h in accordance with European pharmacopeia procedure (25). Yellow-colored oil (yield 2.2%) with characterstic odor and sharp taste was obtained. It was dried over anhydrous sodium sulfate to remove traces of moisture and stored in refrigerator in dark at 4 °C until use. Isolation of the Acetone Extract. After the isolation of the essential oil, the powdered fruits were dried at 25 °C. Extract was obtained by extracting 20 g of dried fruits with 900 mL of acetone for 6 h in a Soxhlet apparatus. The extract was concentrated up to 20 mL. The
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5 75.1 0.5 °C min-1). A control sample was prepared under .0 37.4 tr tr 0.3.1 mL min-1. To assess the antioxidant activity (29-31) of ajwain volatile oil and acetone extract.2 meq kg-1 was taken for present investigation. 280.3 87.0 11.7 12.0 13.7 37.5 26.5 50.2 tr tr 1. GC-MS.2 0. 230. and 275 °C (2 min).7 4 µL 25. The mixtures were thoroughly homogenized and placed into an 80 °C thermostat. Using a Hewlett-Packard 5890 series II gas chromatograph equipped with flame ionization detector (FID) and silica column.0 50. Aspergillus flaVus (AF).0 50.2 0. and it was kept on the lid of Petriplate. Aspergillus ochraceus (AO′). These fungi were isolated from food materials such as onion. Identification of Components. GC.25 18.0 6 µL 37.1 0. dants such as BHA and BHT. 85 °C (1 min). Penicillium Viridicatum (PV). In inverted Petriplate method. 0.1 0.5 25.0 43.0 a Average of three replicates. 1884. whereas in food poison technique. sweet potato.5 4 µL 87.0 87. vegetable waste. 0.3 50. 105-275 °C (10 °C min-1).5 1. The amount of the samples injected was 0.1 tr tr tr 0807 0872 0931 0941 0953 0975 0980 0993 1007 1013 1020 1026 1030 1035 1064 1088 1098 1099 1177 1189 1291 1298 1492 1499 1583 3293 Table 1. and 2073. 60-85 °C (0. which is in inverted position.Ajwain Essential Oil remaining acetone was evaporated by placing the samples in a vacuum drier under reduced pressure. Cultures of each of the fungi were maintained on Czapek (DOX) agar media with adjusting pH 6.0 87. Each test was performed at three concentrations (2.6 tr tr 39. No. GC-MS interphase.5 18. For measuring the peroxide value (32. 2004 Extracta compound 2-methyl but-3-ene-2-ol 2-methyl(methyl butanoate) alpha-thujene alpha-pinene camphene sabinene beta-pinene myrcene alpha-phellandrene delta-3-carene alpha-terpinene p-cymene beta-phellandrene 1.7 0.8 0. Antifungal Investigations. b For all tested fungi.5 52.5 100 75. ion source and selective mass detector temperatures were maintained at 270. 85-105 °C (1 °C min-1).3 87. The oven temperature was programmed as follows: 60 °C (1 min).8-cineole gamma-terpinene terpinolene trans-sabinenhydrate linalool terpinen-4-ol alpha-terpineol thymol carvacrol beta-selinene alpha-selinene caryophyllene oxide delta-dodecalactone 4-methylpent-3-ene-2-one 4-hydroxy-4-methylpent-2-one xylene (isomer not identified) undecane thymoquinone 2. known as oleoresin (yield 3. respectively.6 9. and CurVularia lunata (CL) were undertaken.5 and slants were stored at 5 °C.4 96. 30 m.3 0. 33) a modified oven test (34) was used. 3003. the data was found to be highly significant (p < 0. 60-85 °C (0. film thickness.8 25. India. Table 2. respectively. Chemical constituents were identified by comparing their mass spectra with the library (26. Qualitative and quantitative analysis of volatile oil and acetone extract were undertaken by gas chromatography (GC) and gas chromatography-mass spectroscopy (GC-MS) techniques. 105 °C (2 min). Pencillium citrium (PC). Food Chem. and 6 µL) and replicated three times. tr ) trace. and 280 °C (20 min). the gas chromatograms of the oil and acetone extract were obtained. vegetable. 52. and the results of volatile oil and its acetone extract were reported in Table 1.5 mL min-1.5 56. The column was an HP-5 (5% phenyl methyl silicone. and 275 °C (2 min). 105 °C (2 min).6 10. 4.7 43. and 280 °C(20 min). Chemical Investigation. the required dose (2. 2088. fruits of Musa species. The results taken by inverted Petriplate and food poison technique are given in Tables 2 and 3.6 tr 23. Fusarium graminearum (FG). The volatile oil and acetone extract were subjected to GCMS analysis using a Hewlett-Packard mass detector (model 5973) and an HP-5 MS column (length. respectively. Aspergillus oryzae (AO). 1810. 30-m × 0.8 0.. Fusarium monoliforme (FM). crude linseed oil. The antifungal activity of the volatile oil and acetone extract against fungi were undertaken using inverted Petriplate and food poison techniques (28).1 0. 1846.3 2.0 12. and the test was replicated three times. decaying vegetation. The antioxidant activity of volatile oil and acetone extract were compared with synthetic antioxi- J. and 150 °C.2 0.4. To determine the antifungal efficacy of the volatile oil and its extract. That for acetone extract was as follows: 100 °C (1 min). < 0. and cheese. 85 °C (1 min).5 12.5 °C min-1). 100280 °C (5 °C min-1).7 62.5 100 100 87. were stored in a freezer at 4 °C until use.0 75. Carrier gas used for oil and acetone extract was He with a flow rate of 1. The viscous extract. Antioxidant Activity.1 0.3 0. 1893.25-µm) whose injector and detector temperatures were maintained at 250 and 270 °C.5 21. The injector.5 100 100 100 93.1 µL (in split mode 80:1 for oil and 85:1 for acetone extract).2 30.25 mm. respectively. The MTCC code numbers of these strains are 2479. The percentages of components were obtained from electronic integration measurements using flame ionization detection (FID). the pathogenic fungus Aspergillus niger (AN).3% 68. Vol.0-6.1 tr 0. The retention indices were calculated for all volatile constituents using a homologous series of n-alkanes C8-C16. The oil was selected due to its high degree of unsaturation and generally used as edible oil in Central Europe and Asia. respectively. 2553. 100280 °C (5 °C min-1). 11.1 39.0 87.5 6.7 75.5 12.5 50. having initial peroxide value 4. 2007. Carrier gas used for oil and acetone extract was N2 with a flow rate 1. 1 filter paper. The peroxide values were measured every 7 days.8% a Percentages are the mean of three runs and were obtained from electronic integrations measurements using flame ionization detection (FID).6 1. 4. 27) NBS 75K and/or by co-injection with authentic samples.6-tetramethyl phenol palmitic acid linoleic acid oleic acid total essential oil %FID KIb tr tr 0.7 6 µL 100 100 100 100 100 100 100 100 100 100 ajwain acetone extract 2 µL 12. 4. Antifungal Investigations of Ajwain Essential Oil and Acetone Extract by Using Inverted Petriplate Technique %mycelial zone inhibition at different dose of samplea ajwain essential oil fungusb Aspergillus niger (AN) Aspergillus flavus (AF) Aspergillus oryzae (AO) Aspergillus ochraceus (AO′) Fusarium graminearum (FG) Fusarium monoliforme (FM) Penicillium citrium (PC) Penicillium viridicatum (PV) Penicillium madriti (PM) Curvularia lunata (CL) 2 µL 68. Chemical Composition of Ajwain Essential Oil and Acetone % FID of acetone extract tr 0.05%). and 6 µL) of undiluted sample were soaked on a small piece (diameter 12 mm) of Whatman No. and 6 µL) of the undiluted sample were mixed with the 20 mL of culture medium.1 and 1. The calculated quantities of each (200 ppm) were added to 30 g of linseed oil in an open mouthed beaker.2 1. Agric. and purchased from Microbial Type Culture Collection (MTCC).32-mm × 0. wheat straw. b The retention indices were calculated for all volatile constituents using a homologous series of n-alkanes C8−C16. Pencillium madriti (PM).0 38. 105-275 °C (10 °C min-1).6%). The oven temperature programmed for the volatile oil was as follows: 60° C (1 min). 85-105 °C (1 °C min-1). Peroxide Value Method.2 0. Chandigarh.5 75. respectively. That for acetone extract was as follows: 100 °C (1 min). inner diameter.25 µm).01%. curd.1 1.3 0. the required doses (2.
0 100. Thymol (39.0 18.8 100. and for the standard. using a mechanical shaker.36) with small changes.0 75.0 26. The same sample as prepared for the peroxide value method was used. similar conditions without any additive. Inhibitory effect of ajwain oil and its acetone extract for linseed Average of three replicates. FM. p-cymene (1. . the supernatant was taken and placed in a boiling water bath for 1 h. Using inverted Petriplate technique. and CL was obtained even at a 6-µL dose. Antioxidant activity was carried out using the method (37) proposed by Osawa and Namiki (38) with small changes.5% hydrochloric acid was added to the reaction mixture. oil measured using thiobarbituric acid value method at 80 °C. AO.15 × W where OD ) absorbance of supernatant solution and W ) amount of sample (in grams) The results in the form of plot of incubation time verses TBA value are shown in Figure 2. Determination of Antioxidant Activity in Linoleic Acid System.0 75.3 Figure 2. AO′.0 100. 0.7 27.4%). It is interesting to note that thymol content in both the oil and acetone extract was almost the same. After 2 h.0 100. This mixture was shaken continuously for 2 h.2 100.7 mL of 75% ethanol and 0.5 25. the oil was also found to be active against AO′.5 25.5 25.0 26.0 46.5% linoleic acid in 99.0 100.8%). 11. 0.5 × OD 0. Food Chem. 0.6%).0 50. PC. whereas using the same method. (16) have already reported that thymol is a major component of this oil and there is a compositional variation between a steam distilled oil and oleoresin. followed by oleic acid (10. Table 3. Agric. and several other components in minor percentages. Chialva et al.0 50. γ-terpinene (2. Antifungal Investigations of Ajwain Essential Oil and Acetone Extract Using Food Poison Technique %mycelial zone inhibition at different dose of samplea ajwain essential oil fungusb Aspergillus niger (AN) Aspergillus flavus (AF) Aspergillus oryzae (AO) Aspergillus ochraceus (AO′) Fusarium graminearum (FG) Fusarium monoliforme (FM) Penicillium citrium (PC) Penicillium viridicatum (PV) Penicillium madriti (PM) Curvularia lunata (CL) a ajwain acetone extract 2 µL 18. where there was no addition of sample.7 46.7 100. in the spectrophotometer every 2 days. Samples (4 mg) in 99.1 mL of this solution was added to 9.3 41. β-pinene (1..5 62. Moreover.1 mL of 30% ammonium thiocyanate.3 62.5 87.8 4 µL 26.0 75. which account for 96. as only more than 50% mycelial zone inhibition of AF.1%). AF.5% ethanol were mixed with 2.1 mL). and CL at a 2-µL dose as more than 80% mycelial zone inhibition was obtained. 52. RESULTS AND DISCUSSION Figure 1. 8 mL) and distilled water (3.5 50.0 56. The quantitative data of major components of oil and acetone extract were statistically examined by analysis of variance (ANOVA).05M phosphate buffer (pH ) 7.3% of the total amount.3 50.5% ethanol (4.1%).7 4 µL 100.3 2 µL 100. Thiobarbituric Acid Value (TBA). 2004 Singh et al.3 6 µL 38.0 40.6%). The TBA value (meq/g) was calculated using the following formula: TBA value ) 3. To 0. terpinene-4-ol (0. It was highly effective in controlling mycelial growth of tested Penicillium species even at a 2-µL dose of the oil. acetone extract was found less effective than the volatile oil. The volatile oil on analysis showed the presence of 26 identified components (Table 1).0 87.0 37. FM.5 18. palmitic acid (1. and significant differences among several groups of data were examined by Ducan’s multiple range test. FM.1 mL of 0.9 mL) and kept in screw cap containers under dark conditions at 40 °C.3 62.0 18. The effect of oil and acetone extract on linseed oil in terms of incubation time versus TBA value at 80 °C is shown in Figure 2. acetone extract showed the presence of 18 identified components (Table 1).8% of the total amount.0 77. The effect of oil and acetone extract in terms of linseed oil peroxidation at 80 °C are shown in Figure 1.3 43. b For all tested fungi.0 87. Moreover.6%). Statistical Analysis. No.5 50.0 6. the absorbance of red color was measured at 500 nm The investigation of aroma compounds of the essential oils and acetone extract of dried fruits of ajwain was carried out by means of GC and GC-MS to identify the odorous target component responsible for characteristic odor of valuable spice and food flavoring products.05%). linoleic acid (9.0 100. The analysis of oil and acetone extract of ajwain was undertaken by using previously stated HP-5 series. γ-terpinene (23. using food poison technique (Table 3). the oil was found highly effective against AN. and PV as absolute mycelial zone inhibition was obtained at 6 µL.6%).0 100.8%). The major component was thymol (39. Moreover.5 46. the data was found to be highly significant (p < 0. absorbance of supernatant was measured at 500 nm with Hitachi-U-2000 spectrophotometer.8 31.02 M ferrous chloride in 3. AO′.0 87.5 87. and 4-hydroxy-4-methylpenta-2-one (1. The test was performed according to the methods previously stated by some authors (35.0 37.67% aq thiobarbituric acid (20 mL) and benzene (25 mL) solution were added.5 52. After 3 min.7%).0 6.5 50.3%).0 100. It is very interesting to note that 100% activity of the fungi AN. which account for 68. FG.0 25. The control and standard were subjected to the same procedure except for the control. To 10 g of sample.5 60.0 13. Vol.1%) was found as a major component along with p-cymene (30. 4 mg of sample was replaced with 4 mg of BHA and BHT.3 100. The incubation time versus absorbance is plotted in Figure 3. After cooling. the oil was found to be 100% antifungal against all the tested fungi at a 6-µL dose (Table 2).3 6 µL 100. Inhibitory effect on peroxide accumulation of ajwain Oil and its acetone extract for linseed oil at 80 °C.3294 J.
which refers. K. Agric. The initial stage of peroxide level of lipid oxidation was measured using linoleic acid system. The volatile oil and acetone extract both contain thymol (39. antioxidative properties of these extracts. which is measured by the TBA method. Probably other substances. J. Most likely.05) more effective than the control. DDU Gorakhpur University. Besides this. the volatile oil and acetone extract have been proven to be alternative sources of natural antioxidants and more efficacious than various synthetic antioxidants. the compound used as an index of lipid peroxidation. ACKNOWLEDGMENT We are thankful to the head of the Chemistry Department. During the oxidation process. BHA. Various researchers (17. . hydrolysis and other cleavage processes can release such compounds. 1. The inhibitor activities against lipid peroxidation in linoleic acid caused by additives were evaluated by measuring concentration of ferric thiocynate. The samples with volatile oil and acetone extract were found to be significantly (p < 0. V. Determination of antioxidant activity by linoleic acid method at 40 °C. Status Report on Aromatic and Essential Oil-Bearing Plants in NAM Countries. which needs further investigations. and PV was obtained even at a 2-µL dose of the oil. 19) have already reported that this oil exhibited a broad fungitoxic spectrum. Singh. G. and 300 ppm. acetone extract. 2000. Moreover. 187. BHA and BHT become less effective than acetone extract in stabilizing linseed oil. 11. acetone extract. Med.05). heat. Moreover. and it is more stable at high temperatures than BHT (40). (2) Husain. for 12 days. Their activity is quite comparable to that of BHA and BHT. It is interesting to note that. The oxidation of lipids has been classified as a major deterioration process affecting both the sensory and nutritional quality of food. peroxide value of control sample (without additive) increased to 239 meq/kg. Publication and Information Directorate (CSIR). One such compound is malonaldehyde. S Yadav of our Department is also thanked for providing the spectral facility. During this time. Food Chem. Plants 2002. It should be mentioned that peroxide value method is a widely used measure of primary lipid oxidation. and BHT. peroxides are generally decomposed to lower molecular weight compounds. we can say that the ajwain volatile oil. BHT is very effective in animal fat but less effective in vegetable oils. BHA. LITERATURE CITED (1) Singh. Gorakhpur for providing laboratory facilities. Furthermore. along with the control. acetone extracts are more effective than BHA and BHT at high temperature. the data was found to be highly significant (p < 0. Volatile oil and BHT may also be lost during heating because of their volatility. 63. The results in Figure 1 show that all samples reduce the oxidation rate of linseed oil at 80 °C in terms of formation of peroxide. which could be present in acetone extract and not identified by GC. as only more than 70% mycelial zone inhibition was obtained for FG. 2004 3295 Figure 3. K.. In terms of retarding the formation of primary and secondary oxidation products. and BHT. Several factors can induce changes in the antioxidant activity during the distillation of volatile constituents from spices. These results are well correlated with those obtained previously by peroxide value and TBA methods. 200. PC. Prof. inhibiting the mycelial growth of a number of fungi at 100. Hydroperoxides are primary oxidation products. indicating the amount of peroxides formed in fats and oils during oxidation. Recent Prog. can contribute to improve antioxidant activity of acetone extract. Malonaldehyde. Vol. 1. Peroxide value was measured at time periods of 28 days of storage. after a certain duration (21 days). N. H. BHA and BHT. Low absorbance values indicate high levels antioxidative activity. in general. Concluding these results. Figure 3 shows absorbance values measured for oil. the effectiveness of samples added to the concentration of 200 ppm can be put into the following order: acetone extract > oil > BHA > BHT > control. The curves in Figure 1 demonstrate peroxide value (meq/kg) changes in linseed oil treated with volatile oil..Ajwain Essential Oil J. and PM. which is rich in thymol.6%) do not possess antioxidant activity.05) lower TBA values than the control up to 28 days of incubation at 80 °C. It is known that the effectiveness of added antioxidants varies depending on the food and on the processing and storage conditions (30).1%) as a major component. Govil. No. oleic acid (10. The oil was thermostable and more efficacious than various synthetic fungicides. D.and water-induced chemical reactions can also change the activity of a complex extract system consisting of numerous compounds with different chemical and physical properties. FM. exhibited a broad fungitoxic spectrum by inhibiting the mycelial growth of all tested fungi. was determined by selective third order derivative spectrophotometric method previously developed by some authors (39). 52. Figure 2 shows that volatile oil and acetone extract had significantly (P < 0. BHA is known to be very effective antioxidant for vegetable oils.4%) and linoleic acid (9.. In acetone extract. whereas using the same method acetone extract was found to be comparatively less effective than the volatile oil. The values obtained without additives were taken for 100% lipid peroxidation.
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