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jfpe_347 175..185

RUI WANG, RUIJIANG WANG1 and BAO YANG South China Botanical Garden Chinese Academy of Sciences Guangzhou 510650, China
Accepted for Publication September 19, 2008

ABSTRACT Cinnamon is an important herbal medicine with good effects of health promotion and disease prevention. In this work, the volatile compounds of cinnamon bark were extracted by hydrodistillation and solid phase microextraction techniques. Gas chromatography/mass spectrometry was used to identify and quantify the volatile compound composition. The results indicated that trans-cinnamaldehyde was the major component with the highest area percentage of 68.67% in the volatile oils extracted by hydrodistillation. The next were glycerol 1-methyl ether and o-methoxycinnamaldehyde with area percentages of 23.29 and 1.44%, respectively. The number of alkenes, alkanes, alcohols, aldehydes, amines, carboxylic acids, ethers, esters and ketones were 17, 1, 12, 8, 2, 2, 6, 3 and 6, respectively. The volatile compounds extracted by headspace solid phase microextraction were apparently different from those by hydrodistillation. Three major volatile compounds were 1,2,3,4,4a,5,6,8aoctahydro-7-methyl-4-methylene-1-(1-methylethyl)-naphthalene, 1,2,3,4a,5, 8,8a-hexahydro-4,7-methyl-1-methylene-1-(1-methylethyl)-naphthalene and copaene with area percentages of 20.18%, 17.21% and 16.51%, respectively. Alkenes (31), alcohols (10), aldehydes (4), carboxylic acids (2) and ethers (3) were found in this assay.

PRACTICAL APPLICATIONS Cinnamon bark has been taken as an important traditional herbal medicine due to its disease prevention effect. The volatile compounds of cinnamon

Corresponding author. TEL: +86-20-37252662; FAX: +86-20-37252662; EMAIL: wangrj@ scbg.ac.cn

Journal of Food Process Engineering 34 (2011) 175185. All Rights Reserved. Copyright the Authors Journal Compilation 2009 Wiley Periodicals, Inc. DOI: 10.1111/j.1745-4530.2008.00347.x




bark contribute much to its bioactivities. In this work, the volatile oils were extracted by hydrodistillation technique. Head space solid phase microextraction technique was also used to detect the volatile compounds. Gas chromatography/mass spectrometry analysis showed the signicant difference of volatile compound composition between two extractions. transCinnamaldehyde was conrmed to be the major component of volatile oils that has good pharmacological properties. This work is helpful for extensive development of this medicinal herb.

INTRODUCTION Cinnamon belongs to the family Lauraceae. It is one of the oldest herbal medicines, which has been recorded in Chinese publications 4,000 years before (Qin et al. 2003). The cinnamon bark is frequently used as a avoring spice in food preparation in many Asian countries, such as India and China (Sharma et al. 2001). Its potential properties of health promotion and disease prevention have attracted increasing attention in recent years. Cinnamon has been used to treat dyspepsia, gastritis, blood circulation disturbance and inammatory diseases in many countries since ancient age (Yu et al. 2007). The signicant anti-allergic, anti-ulcerogenic, antipyretic, anaesthetic and analgesic activities have been conrmed previously (Kurokawa et al. 1998; Lee and Ahn 1998). The in vitro investigation of cinnamon has revealed that its extract mimics the function of insulin, which potentiates insulin action in isolated adipocytes (Broadhurst et al. 2000). Moreover, cinnamon extract can also improve the insulin receptor function (Jarvill-Taylor et al. 2001). Volatile oils, also named as essential oils, occur in many medicinal plants, which are responsible for the fragrance of plants. They are commonly extracted by hydrodistillation or solvent extraction (Benchaar et al. 2008). The volatile compound composition of essential oils of one material will be different depending on the species, location and extraction method. Essential oils are important components of cinnamon bark, which are natural harmless preservatives applied in food products (Matan et al. 2006). Cinnamaldehyde is an important component in cinnamon oils. It has been identied as an effective fungitoxic substance, and also conrmed to be a good immunomodulator and anticancer agent (Koh et al. 1998; Lee et al. 1999). The Food and Drug Administration of U.S.A. has approved cinnamaldehyde as a safe food additive due to its special avor. Moreover, essential oils are well known inhibitors of microorganisms. The cinnamon essential oils have been proved to inhibit the growth of molds, yeasts and bacteria (Soliman and Badeaa 2002). Up to now, publications on the chemical composition of volatile compounds in cinnamon bark are few. Identication of volatile compounds in cinnamon


bark will be helpful to understand this medicinal herb. Therefore, in this work, volatile compounds were extracted by hydrodistillation and identied by GC/MS. Headspace solid phase microextraction was also used to compare the difference of two extraction methods.

MATERIALS AND METHODS Plant Material Cinnamon (Cinnamomum cassia Presl) barks were collected from Fangcheng, Guangxi province of China. They were air dried in an oven (DGG-9240A, Shanghai Linpin Experiment Instrument Co., Shanghai, China) at 50C for 24 h. Then they were subjected to pulverization by a cutting mill (DFT-50, Lingda Mechanics Co, Zhejiang, China) and sieved through a 60-mesh sieve. Preparation of Volatile Compounds by Hydrodistillation The volatile oils of cinnamon bark were obtained by hydrodistillation in a Clevenger-type apparatus, according to the method of Demirci et al. (2008) with slight modication. Fifty grams of cinnamon bark powder were precisely weighed and mixed with 200 mL of distilled water. They were heated at 100C for 5 h. Ethyl ether (200 mL) was used to extract volatile compounds from the water phase for three times. The ethyl ether fraction was dehydrated over anhydrous sodium sulphate and ltered through a mid-speed lter paper. After concentration by rotary evaporation at room temperature (25C), the resulting volatile extract was kept at 4C for further analysis. Preparation of Volatile Compounds by Headspace Solid Phase Microextraction The preparation of volatile compounds by headspace solid phase microextraction was done following the method of Wu et al. (2008). Ten grams of cinnamon bark was precisely weighed and mixed with 150 mL of distilled water in a conical ask, which was sealed by a teon/silicone septum. A headspace solid phase microextraction ber (Supelco, Bellefonte, PA) with 50/30 mm of divinylbenzene/carboxen on polydimethylsiloxane coating was inserted through the septum and exposed to the headspace of the ask. The volatile compounds were absorbed by the ber when heating at 50C for 2 h by a magnetic stirrer (JB-3, Rongguan Instrument Company, Changzhou, China). Then, the ber with target compounds was subjected to gas chromatography/



mass spectrometry (GC/MS) analysis directly. The ber needed to be conditioned before use according to the manufacturers prescription. GC/MS Analysis GC/MS analysis was performed on a GC-2010 gas chromatograph (Shimadzu, Japan) equipped with a GCMS-QP2010 Plus mass spectrometer (Shimadzu, Japan). A Rxi-5MS capillary column (30 m 0.25 mm i.d., lm thickness 0.25 mm, Shimadzu, Japan) was used for separation. A split/splitless injector was used. Oven temperature was kept at 40C for 3 min, increasing to 120C at 5C/min and holding for 3 min, then to 180C at 2C/min and holding for 3 min, and nally to 230C at 5C/min and holding for 3 min. Injector temperature was 250C, while the detector temperature was 250C. The ion source temperature was 250C. Helium was used as the carrier gas with a ow rate of 30 mL/min. Identication of compounds was based on comparison of their mass spectra with those recorded in the National Institute of Standards and Technology database. Quantitative analysis of each essential oil component (expressed as area percentage) was carried out by peak area normalization measurement. For the volatile compounds prepared by hydrodistillation, sample (0.2 mL) was injected into the injector with a split ratio of 1:50. For identication of volatile compounds prepared by headspace solid phase microextraction, the ber was injected into the injector directly and a split ratio of 1:5 was used. RESULTS AND DISCUSSION The Volatile Compounds Obtained by Hydrodistillation The essential oil yield was 1.3 0.2% (w/w) by hydrodistillation. GC/MS was used to identify the volatile compounds in the extract of hydrodistillation and those absorbed on the ber of solid phase microextraction instrument. The volatile compound compositions of two extracts are listed in Tables 1 and 2, respectively. As shown in Table 1, the volatile oil of cinnamon bark consisted of 57 kinds of volatile compounds, including alcohols, aldehydes, alkanes, alkenes, amines, carboxylic acids, ethers, esters and ketones. GC/MS analysis revealed that trans-cinnamaldehyde was identied as the major component with the highest area percentage of 68.67%. The area percentages of glycerol 1-methyl ether and o-methoxycinnamaldehyde were 23.29% and 1.44%, respectively. Other volatile compounds identied from the extract were lower than 1%. Seventeen alkenes were found in the extract, while the numbers of alkanes, alcohols, aldehydes, amines, carboxylic acids, ethers, esters and ketones were 1, 12, 8, 2, 2, 6, 3 and 6, respectively.



Compound Type Retention time (min) Area percentage (%) 23.29 0.12 0.06 0.01 0.01 0.01 0.01 0.55 0.01 0.01 0.23 0.17 0.02 0.03 0.02 0.01 0.05 0.46 0.27 0.04 0.08 0.01 0.03 0.01 0.02 0.22 68.67 0.39 0.05 0.23 0.91 0.08 0.04 0.30 0.08 0.15 0.59 0.01 0.02 0.06 0.01 0.11 0.01 0.31 1.44 0.10 0.05 0.05 0.03 0.15 0.14 0.05 0.01 0.12 0.02 0.04 0.03

Glycerol 1-methyl ether Cinnamene Isopropyl acetate 2-Isopropoxyethylamine 2,4,6-Trimethyl-trioxane Ethyl isopropyl ether Propylbenzene Benzaldehyde Ethenyl benzeneethanol 2,4-Dimethyl-3-hexanone Propenyl benzene Benzeneacetaldehyde Acetophenone a-Methyl benzeneacetaldehyde Benzeneethanol 2-Methyl-3-phenyloxirane 1-Isopropylvinyl benzene Glycerin Hydrocinnamaldehyde Phenyl ethyl ketone Borneol Benecarboxylic acid 1,2-Naphthalenedione Terpineol 6-Ethyl-2-methyl decane b-Methyl benzenepropanal trans-Cinnamaldehyde Benzenepropanol trans-Benzalacetone 2-Phenylhexane 5-(2-Propenyl)-1,3-benzodioxole Cinnamyl alcohol b-Methyl-benzenepropanal Eugenol Copaene a-Ethyl-benzenemethanol Cinnamic acid N-Benzoyl-alanine Ethyl cinnamate Germacrene a-Curcumene Muurolene Myrcene Cadina-1(10),4-diene o-Methoxycinnamaldehyde 1,2,3,4,4a,7-Hexahydro-1,6-dimethyl-4-(1-methylethyl)-naphthalene 4-(2,6,6-Trimethyl-2-cyclohexen-1-ylidene)-2-butanone trans-8-Ethyl-bicyclo(4.3.0)non-3-ene Artemesia triene Cedr-9-ene Muurolol a-Cadinol a-Bisabolol 2-Methyl-benzofuran 1,5-Diphenyldex-3-ene Vinyl trans-cinnamate 1-Butylheptyl-benzene

Ether Alkene Ester Amine Ether Ether Alkene Aldehyde Alcohol Ketone Alkene Aldehyde Ketone Aldehyde Alcohol Ether Alkene Alcohol Aldehyde Ketone Alcohol Carboxylic acid Ketone Alcohol Alkane Aldehyde Aldehyde Alcohol Ketone Alkene Ether Alcohol Aldehyde Alcohol Alkene Alcohol Carboxyl acid Amine Ester Alkene Alkene Alkene Alkene Alkene Aldehyde Alkene Ketone Alkene Alkene Alkene Alcohol Alcohol Alcohol Ether Alkene Ester Alkene

5.716 7.510 8.154 8.506 9.296 9.467 9.556 9.732 10.807 11.122 11.900 12.458 13.182 14.350 14.662 14.765 14.898 15.366 16.162 16.235 16.286 16.759 16.886 17.034 17.313 17.602 17.880 18.185 18.975 19.125 20.079 20.527 21.219 22.477 23.284 23.768 25.699 26.391 27.204 27.791 28.085 28.934 29.348 30.041 30.296 30.458 32.411 33.061 35.001 35.180 35.874 36.089 38.128 59.712 60.929 61.191 62.336



Compound Type Retention Area time (min) percentage (%) 2.171 4.829 12.687 16.173 16.303 17.869 18.838 19.580 20.202 22.641 22.896 23.740 24.107 24.304 24.620 24.853 25.052 25.277 25.418 25.657 25.974 26.090 26.586 26.805 26.990 27.099 27.260 27.747 28.104 28.230 28.356 28.460 28.795 29.774 30.629 30.968 31.277 31.565 32.264 32.740 33.170 33.613 34.040 34.590 35.328 36.009 36.188 36.558 37.388 38.185 0.09 0.07 0.10 0.14 0.09 0.31 0.07 1.95 1.76 0.46 0.89 16.51 1.55 1.15 0.17 0.68 0.31 1.70 0.25 0.30 1.02 0.38 0.38 2.09 0.60 0.68 0.15 1.84 1.07 0.71 0.78 0.22 2.44 20.18 17.21 7.62 3.46 0.26 0.75 0.25 1.22 0.35 0.71 0.84 2.64 1.90 0.64 0.37 0.32 0.35

Formic acid Acetol b-Ocimene Hydrocinnamaldehyde Borneol trans-Cinnamaldehyde 5-hydroxymethyl-2-furancarboxaldehyde 5-Norbornene-2-carboxylic acid 5-(2-propenyl)-1,3-benzodioxole 3-Allyl-6-methoxyphenol Octahydro-1,7a-dimethyl-5-(1-methylethyl)-1,2,4-metheno-1H-indene Copaene 1-Ethenyl-1-methyl-2,4-bis(1-methylethenyl)-cyclohexane Octahydr-4-methyl-8-methylene-7-(1-methylethyl)-1,4-Methano-1H-indene 1-Propyl-1-nonenyl-benzene (-)-Isosativene 2,6-Dimethyl-6-(4-methyl-3-pentenyl)-2-norpinene Caryophyllene b-Humulene Octahydro-7-methyl-3-methylene-4-(1-methylethyl)Cyclopental(1,3)cyclopropal(1,2)benzene 2,6-Dimethyl-6-(4-methyl-3-pentenyl)-bicyclo(3.1.1)hept-2-ene 1,2,3,4,5,6,7,8-Octahydro-1,4-dimethyl-7-(1-methylethenyl)-azulene 3,4,4a,5,6,8a-Hexahydro-2,5,5,8a-tetramethyl-2H-1-benzopyran 1,5,9,9-Tetramethyl-1,4,7-cycloundecatriene 4,5-Dimethyl-2,6-octadiene Decahydro-1,1,7-trimethyl-4-methylene-1H-cycloprop(e)azulene 1,8-Dimethyl-4-(1-methylethenyl)-spiro(4,5)dec-7-ene (+)-Epi-bicyclosesquiphellandrene 1,2,4a,5,6,8a-Hexahydro-4,7-dimethyl-1-(1-methylethyl)-naphthalene 1-Methyl-4-(1,2,2-trimethylcyclopentyl)-benzene Eudesma-4(14),11-diene 2-Methylene-4,8,8-trimethyl-4-vinyl-biocyclo(5.2.0)nonane 1a,2,3,5,6,7,7a,7b-Octahydro-1,1,4,7-tetramethyl-1H-cycloprop(e)azulene 1,2,3,4,4a,5,6,8a-Octahydro-7-methyl-4-methylene-1-(1-methylethyl)naphthalene 1,2,3,4a,5,8,8a-Hexahydro-4,7-methyl-1-methylene-1-(1-methylethyl)naphthalene 2,6,6,9-Tetramethyl-tricyclo([2,8])undec-9-ene 4-(1,5-Dimethyl-1,4-hexadienyl)-1-methyl-cyclohexene 1-Ethenyl-1-methyl-2-(1-methylethenyl)-4-(1-methylethylidene)-cyclohexane Longifolenaldehyde (-)-Spathulenol 1-Ethenyl-1-methyl-2-(1-methylethenyl)-4-(1-methylethylidene)-cyclohexane Diepi-a-cedrene epoxide 8-(1,4,4a,5,6,7,8,8a-Octahydro-2,5,5,8a-tetramethylnaphth-1-yl)-6methyl-oct-5-en-2-ol Carotol 2,6,6,9-Tetramethyl-tricyclo([2,8])undec-9-ene 1,2,3,4,4a,7,8,8a-Octahydro-1,6-dimethyl-4-(1-methylethyl)-1-naphthalenol 1,2,3,4,4a,7,8,8a-Octahydro-1,6-dimethyl-4-(1-methylethyl)-1-naphthalenol a-Cadinol 1-(1,5-Dimethyl-4-hexenyl)-4-methyl-3-cyclohexen-1-ol a-Bisabolol

Carboxylic acid Alcohol Alkene Aldehyde Alcohol Aldehyde Aldehyde Carboxyl acid Ether Alcohol Alkene Alkene Alkene Alkene Alkene Alkene Alkene Alkene Alkene Alkene Alkene Alkene Ather Alkene Alkene Alkene Alkene Alkene Alkene Alkene Alkene Alkene Alkene Alkene Alkene Alkene Alkene Alkene Aldehyde Alcohol Alkene Ether Alcohol Alcohol Alkene Alcohol Alcohol Alcohol Alkene Alcohol


Hydrodistillation is known to be one of the most common methods for the extraction of volatile compounds from different matrix (Golmakani and Rezaei 2008). Though it has some disadvantages, such as loss of some volatile compounds, low extraction efciency, possible degradation of unsaturated compounds through thermal or hydrolytic effects (Bayramoglu et al. 2008), it is still widely used due to free of organic solvent during extraction, convenience and cost-effectiveness. Singh et al. (2007) have reported the major volatile compounds in essential oil of Cinnamomum zeylanicum Blume bark prepared by hydrodistillation. They have indicated that trans-cinnamaldehyde was the major component accounting for 97.7%, along with cadinene (0.9%). The cinnamon cultivar and location should be responsible for the difference from our results. Tung et al. (2008) have measured the essential oils extracted from twig of cinnamon by hydrodistillation. The main components are L-bornyl acetate (15.89%), caryophyllene oxide (12.98%), g-eudesmol (8.03%), b-caryophyllene (6.60%), T-cadinol (5.49%), d-cadinene (4.79%), trans-b-elemenone (4.25%), cadalene (4.19%) and trans-cinnamaldehyde (4.07%), respectively. This indicates that the volatile compound compositions are correlated with growth stage and different parts of cinnamon tree. From the results obtained in this work, the volatile oils of cinnamon bark enriched in alcohols, aldehydes and alkenes. These compounds have good potential as antioxidant. Tomaino et al. (2005) have suggested that essential oils of cinnamon possess good 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity. They can also prevent a-tocopherol from oxidative degradation. The essential oils of cinnamon bark have been found to have signicant inhibition of nitric oxide production (Lee et al. 2002), which is closely correlated with the pathophysiology of many diseases and inammations. The antimicrobial and antifungal activities of cinnamon essential oils have also drawn much attention from some researchers (Singh et al. 1995). trans-Cinnamalhyde was detected to be the major volatile compounds in the volatile oils. It is also a good bioactive substance, which has many pharmacological properties. Oral administration of cinnamaldehyde can signicantly decrease the glycosylated hemoglobin, serum total cholesterol, triglyceride levels and increase the plasma insulin, hepatic glycogen and high density lipoprotein-cholesterol levels of diabetic rats (Babu et al. 2007). The Volatile Compounds Obtained by Headspace Solid Phase Microextraction Table 2 lists the volatile compounds obtained by headspace solid phase microextraction. Fifty volatile compounds were identied in this assay. Alcohols, aldehydes, alkenes, carboxylic acids and ethers were involved. Three major volatile compounds were shown in Table 2. They



were 1,2,3,4,4a,5,6,8a-octahydro-7-methyl-4-methylene-1-(1-methylethyl)naphthalene, 1,2,3,4a,5,8,8a-hexahydro-4,7-methyl-1-methylene-1-(1methylethyl)-naphthalene and copaene with area percentages of 20.18%, 17.21% and 16.51%, respectively. This result was completely different from the major volatile compounds in the extract obtained by hydrodistillation. The area percentage of trans-cinnamaldehyde was only 0.31% in this analysis. The number of alkenes was 31, much more than that of alcohols (10), aldehydes (4), carboxylic acids (2) and ethers (3). The number and total area percentage of alkenes indicated that they are the major volatile compounds absorbed to the ber. Headspace solid phase microextraction was introduced as an effective extraction technique for volatile compounds decades before (Zygmunt et al. 2001). This technique is mainly used for air analysis in which the exposed ber is suspended over the sample in a sealed environment. The volume of sample has a signicant effect on the analysis due to its effect on the depletion rate of individual species in the headspace (Grecki 1997). Sampling time and ber coating composition are also important for accurate determination, because they will affect the absorption to the ber coating, degradation and cross reaction of analytes (Lpez et al. 2006). In this work, the analytic conditions were chosen basing on our previous work. The ber with coating of divinylbenzene/carboxen/polydimethylsiloxane was chosen. The volume of sample (150 mL) and sampling time (2 h) were set. The results obtained in this work indicated that the volatile compounds obtained by headspace solid phase microextraction were apparently different from those by hydrodistillation. The ber coating composition should be correlated with the results due to its afnity to analytes (Kataoka et al. 2000). Polydimethylsiloxane ber is preferred to extraction of nonpolar analytes. Mixing with divinylbenzene/carboxen can increase the retention capacity of polydimethylsiloxane due to mutual effect of adsorption and distribution to the stationary phase. This might explain that the alkenes were easier to be absorbed to the coating than others in this work. The volatility of analytes is another factor affecting the analysis. The very volatile analytes are more difcult to be extracted by hydrodistillation than the semi-volatile analytes. However, they can be extracted by solid phase microextraction due to low temperature and sealed environment. The above reasons led to the difference in the composition of volatile compounds obtained by two extraction techniques. CONCLUSIONS Through GC/MS analysis, the composition of volatile compounds of cinnamon bark obtained by hydrodistillation was apparently different from


those by headspace solid phase microextraction. trans-Cinnamaldehyde was the major component with the highest area percentage of 68.67% in the volatile oils extracted by hydrodistillation. Fifty-seven volatile compounds were found in the volatile oils, including alkenes (17), alkanes (1), alcohols (12), aldehydes (8), amines (2), carboxylic acids (2), ethers (6), esters (3) and ketones (6). While fty volatile compounds with alkenes (31), alcohols (10), aldehydes (4), carboxylic acids (2) and ethers (3) were identied for the extract obtained by headspace solid phase microextraction. Three major volatile compounds were 1,2,3,4,4a,5,6,8a-octahydro-7-methyl-4methylene-1-(1-methylethyl)-naphthalene, 1,2,3,4a,5,8,8a-hexahydro-4,7methyl-1-methylene-1-(1-methylethyl)-naphthalene and copaene with area percentages of 20.18%, 17.21% and 16.51%, respectively. Hydrodistillation reected the true composition of volatile oils in cinnamon bark, while headspace solid phase microextraction just gave the prole of readily volatile compounds absorbed on the ber coating. Further measurement of the bioactivity of cinnamon bark volatile oils will be interesting. The comparison of volatile compounds between cultivars is also undergoing in our work. ACKNOWLEDGMENTS The nancial support from Guangdong Science and Technology Program (No. 2006B23004003) was appreciated. REFERENCES BABU, P.S., PRABUSEENIVASAN, S. and IGNACIMUTHU, S. 2007. Cinnamaldehyde a potential antidiabetic agent. Phytomedicine 14, 1522. BAYRAMOGLU, B., SAHIN, S. and SUMNU, G. 2008. Solvent-free microwave extraction of essential oil from oregano. J. Food Eng. 88, 535540. BENCHAAR, C., CALSAMIGLIA, S., CHAVES, A.V., FRASER, G.R., COLOMBATTO, D., MCALLISTER, T.A. and BEAUCHEMIN, K.A. 2008. A review of plant-derived essential oils in ruminant nutrition and production. Anim. Feed Sci. Tech. 145, 209228. BROADHURST, C.L., POLANSKY, M.M. and ANDERSON, R.A. 2000. Insulin-like biological activity of culinary and medicinal plant aqueous extracts in vitro. J. Agric. Food Chem. 48, 849852. DEMIRCI, F., GUVEN, K., DEMIRCI, B., DADANDI, M.Y. and BASER, K.H.C. 2008. Antibacterial activity of two Phlomis essential oils against food pathogens. Food Control 19, 11591164.



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