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Food and Bioproducts Processing

journal homepage: www.elsevier.com/locate/fbp

Effect of drying methods on volatiles of Chinese ginger (Zingiber ofcinale Roscoe)

S.H. Ding a,b,c , K.J. An a,b,c , C.P. Zhao a,b,c , Y. Li a,b,c , Y.H. Guo a,b,c , Z.F. Wang a,b,c,
a b c

College of Food Science and Nutritional Engineering, China Agricultural University, Beijing 100083, China National Engineering and Technology Research Center for Fruits and Vegetable Processing, Beijing 100083, China Key Laboratory of Fruits and Vegetables Processing, Ministry of Agriculture, Beijing 100083, China

a b s t r a c t
Fresh ginger slices were dehydrated by air drying (AD), microwave drying (MD), vacuum drying (VD), and freezing drying (FD). Volatiles were extracted from fresh ginger pulp and dried ground ginger powder with solid-phase microextraction (SPME), and identied by gas chromatographymass spectrometry (GCMS). Results indicated that, 19, 28, 21, 20, 31 and 20 novel compounds (70 in total) appeared in dried gingers treated by AD at 50, 60 and 70 C, MD at 60 W, VD in 13.3 kPa at 60 C and FD in 0.203 kPa at chamber temperature of 22 C, respectively. Principal component analysis for the main volatiles indicated that drying increased the relative contents of benzene,1-(1,5-dimethyl-4-hexenyl)-4-methyl-, 1,3-cyclohexadiene,5-(1,5-dimethyl-4-hexenyl)-2-methyl-,[S-(R*,S*)], -farnesene and cyclohexene,3-(1,5-dimethyl-4-hexenyl) -6-methylene-,[S-(R*,S*)]- while decreased those of 2,6-octadienal,3,7-dimethyl-,(Z) and 2,6-octadienal,3,7-dimethyl-. Cluster analysis disclosed that MD was the most favorite drying way, followed by AD at 60 C, VD, FD, and AD at 50 and 70 C. 2011 The Institution of Chemical Engineers. Published by Elsevier B.V. All rights reserved. Keywords: Ginger; Drying; Volatiles; Solid-phase microextraction(SPME); Gas chromatographymass spectrometry (GCMS); Principal component analysis; Cluster analysis

1.

Introduction

Ginger (Zingiber ofcinale Roscoe) has been cultivated in many tropical and subtropical countries including China, India, Nigeria, Australia, Jamaica and Haiti on account of its culinary and medicinal properties (Bartley and Jacobs, 2000). Its roots and the obtained extracts contain polyphenol compounds (6gingerol, 8-gingerol, 10-gingerol and its derivatives) (Pawar et al., 2011; Schwertner and Rios, 2007; Zhan et al., 2011), which have a high antioxidant activity (Stoilova et al., 2007) and antiinammatory effect (Dugasani et al., 2010). Ginger is typically consumed as a fresh paste, dried slices/powder, candy (crystallized ginger) or avoring tea and also used as a condiment in various industries of food, beverage, and fragrance, especially in China for its pungent constituents and aromatic volatile constituents. The volatile constituents play a dominating role in imparting the characteristic, pleasant smell in various ginger products.

The chemical composition of fresh ginger are different due to different geographical locations (Bartley and Foley, 1994; Bailey-Shaw et al., 2008; Macleod and Pieris, 1984; Vanbeek et al., 1987), varieties (Wohlmuth et al., 2006), extraction methods (Chen and Ho, 1988; Badalyan et al., 1998; Gong et al., 2004; Shao et al., 2003; Zancan et al., 2002) and processing technologies (Bartley and Jacobs, 2000; Mishra et al., 2004; Variyar et al., 2006). Drying reduces the moisture content and hence inhibits microbial growth and forestalls certain biochemical changes but, it does lead to loss of aroma and has an adverse effect on the nutrients, physical properties (Phoungchandang and Saentaweesuk, 2010) and antioxidant activity (Chan et al., 2009), at the same time, induces some novel components (Chen and Ho, 1989). Air drying (AD), microwave drying (MD), vacuum drying (VD) and freezing drying (FD) are widely used to dehydrate fruits and vegetables. So far, no other studies have been focused on the comparison of volatiles in ginger

Corresponding author at: P.O. Box 303 of China Agricultural University, Qinghua East Road No. 17, Haidian District, Beijing 100083, China. Tel.: +86 10 62737645; fax: +86 10 62737434x601. E-mail address: wzhfuwzhfu@163.com (Z.F. Wang). Received 7 June 2011; Received in revised form 26 September 2011; Accepted 12 October 2011 0960-3085/$ see front matter 2011 The Institution of Chemical Engineers. Published by Elsevier B.V. All rights reserved. doi:10.1016/j.fbp.2011.10.003

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dehydrated by different drying methods (AD, MD, VD and FD). Therefore, the purpose of this research was to investigate the inuence of those four drying methods on the avor of dehydrated ginger and recommend a best drying method by using principle analysis and cluster analysis.

culture dish, and dried in 13.3 kPa at 60 C for 490 min when the sample moisture content reduced to about 5% (w.b.).

2.2.4.

Freeze drying (FD)

2.
2.1.

Materials and methods

Raw materials

Matured, apparently healthy fresh ginger was purchased in March, 2011, from a local market, which was planted in a greenhouse in Laiwu County, Shandong province, China, and harvested in March, 2011 in its completely maturation stage. Prior to drying, the purchased ginger was stored for a couple of days in sand at about 15 C in a storage, and then samples were taken out of the storage, peeled manually and cut into cylindrical slices with thickness of 4 mm and diameter of 33.3 mm by using a cutting machine. All the slices used for drying were from the same batch. The initial moisture was determined by using a vacuum oven in 13.3 kPa at 70 C until the constant weight of sample reached (AOAC, 1990).

The freezing drying was conducted as follows: ginger slices of 0.1 kg were laid in a salver and put in an ultra low temperature refrigerator (80 C) for 4 h. The pre-frozen sample was put into a freezing dryer (type LGJ-10, Beijing Songyuan Huaxin Science and Technology Development Ltd. Co., Beiijing, China), and dried in the vacuum degree of 0.203 kPa at chamber and condenser temperature levels of 22 C and 55 C. According to our pre-experiment, the freezing drying lasted for 29 h when the moisture content of ginger slices reached about 5% (w.b.).

2.3. 2.3.1.

Analysis of volatiles Extraction and concentration of volatiles

2.2. 2.2.1.

Drying methods Air drying (AD)

Air drying of ginger slices was conducted in an electricheating air blast dryer with cavity dimension of 400 mm 400 mm 300 mm (DHG-9053A; Shanghai Jinghong Experimental Facilities Corporation Ltd., Shanghai, China). The dryer consists of temperature control unit that can set temperature between 20 and 120 C, a fan, a thermocouple (0.1 C) and a heating chamber. The mass of samples was about 0.10 kg for each batch. The samples were spread in a single layer on the stainless steel net in the middle of the chamber, and the thermocouple was located in a position at 5 102 m above the sample. The hot air owed from one side to the opposite side of the chamber, paralleling to the tray surface, at a constant speed of 0.75 0.03 m s1 . Three different drying temperature levels used for this study were 50, 60, and 70 C, respectively. At the last phase of drying the tray was taken out from time to time and weighted with an electrical balance, drying stopped when the sample moisture (w.b.) reached about 5%.

Fresh ginger was homogenized in a blender and dehydrated ginger was milled in a mortar at room temperature, and then the milled samples were sieved with an 80 mesh wire screen. The homogenized fresh ginger paste or sieved ginger powder samples of 1.0 g were placed in a 15 mL vial, and the homogenized sample was additionally mixed with 0.4 g sodium chloride in order to reach a saturated solution, and then all vials were sealed and stored at ambient temperature prior to extraction. According to Shao et al. (2003), a 100 m polydimethyl-siloxane (PDMS) bre proved to be the most useful in extraction of ginger volatiles when compared to 30 m PDMS, 75 m carboxen-polydimethylsiloxane (Carboxen-PDMS) and 65 m polydimethylsiloxanedivinylbenzene (PDMS-DVB). Therefore, the volatile components of ginger sample were isolated by solid-phase micro-extraction (SPME) with a 100 m length PDMS ber column (Supelco, USA) at 40 C for 30 min and eluted at 250 C for 5 min.

2.3.2. Gas chromatographymass spectrometry analysis (GCMS)

SPME ber was injected into the port of an Agilent 7890-5975C GC/MSD (Agilent Technology, USA) with a HP-5 (Agilent) elastic quartz capillary column (30 m 0.25 mm, 0.25 m lm thickness) and desorbed at 250 C for 5 min. The injection port was operated in split mode, the ow rate of high purity helium as carrier gas was 1 mL min1 . The initial oven temperature was 50 C, held for 1 min, ramped at 5 C min1 to 120 C, held for 40 min, and then ramped at 3 C min1 to 250 C. Mass detector was conducted with electronic impact (EI) mode at 70 eV, source temperature of 250 C, scanning rate of 1 scan s1 and mass acquisition range between 35 and 550 amu. Identication of the components was performed by comparing the mass spectra with those recorded in the NIST (including Wiley and Mainlib) library. Only compounds whose similarity is more than 78 (the maximum similarity is 100) were reported here. Quantitative analysis was based on the ratios between peak area of a particular component and the total peak area of components identied by GCMS.

2.2.2.

Microwave drying (MD)

The microwave drying was performed in an experimental microwave oven with cavity dimension of 350 mm 350 mm 240 mm, operating at 2455 MHz (N073J, Nanjing Jiequan Microwave Apparatus Co. Ltd., Nanjing, China). The experimental system can be linearly adjusted to power level from 0 to 700 W and time scope from 0 to 999 s or min. Ginger slices with an approximate mass of 0.10 kg were spread in a single layer on a glassy culture dish, and dried at 60 W of the microwave power. Based on pre-experiment, drying lasted for 320 min when the sample moisture reached about 5% (w.b.).

2.2.3.

Vacuum drying (VD)

2.4.

Principal component analysis and cluster analysis

The vacuum drying was carried out in a vacuum drying oven with cavity dimension of 415 mm 370 mm 345 mm (DZF6050, Shanghai CIMO Medical Instrumental Manufacturing Co., Ltd., Shanghai, China). Ginger slices with an approximate mass of 0.10 kg were spread in a single layer on a glassy

Principal composition analysis and cluster analysis were conducted by using SAS (Statistical Analysis System) v9.2 software in order to evaluate the inuence of different drying ways on the main volatiles of the ginger.

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3.

Results and discussion

3.1. Fresh ginger volatiles separated and identied by GCMS

Although nearly 100 peaks were separated by GC, due to their relative peak values only 55 components identied by MS were listed in Table 1. The components identied were mainly alkenes, ketones, alcohols, aldehydes and cyclones, accounting for more than 97% of the chromatographic area, and the remainder was unidentied components and impurities. The major components identied in fresh ginger were 1,3-cyclohexadiene, 5-(1,5-dimethyl4-hexenyl)-2-methyl-,[S-(R*,S*)]- (28.124%), 2,6-octadienal,3,7dimethyl- (15.713%), cyclohexene,3-(1,5-dimethyl-4-hexenyl)6-methylene-,[S-(R*,S*)]- (7.645%), -phellandrene (7.532%), -farnesene (6.905%), camphene (6.657%), eucalyptol (5.658%), and 2,6-octadienal,3,7-dimethyl-,(Z) (5.651%). Variyar et al. (1997) have reported that two main fractions of the volatile from fresh ginger oils were -phellandrene and camphene. Their peak area percentages were 4.9% and 1.9%, respectively. Bartley and Jacobs (2000) have also reported that the volatile components in supercritical uid extracts of fresh ginger, which identied 62 components, also include -phellandrene and camphene. However, the amount of the geranial was highest (18.47%) in the extracts of fresh ginger, followed by zingiberene (13.44%), zingerone (7.49%), 6-gingeol (6.30%) and -sesquiphellandrene (5.85%). Nishimura (1995) have used aroma extract dilution analysis and modied multidimensional GCMS to identify the characteristic odorants in fresh ginger and reported that compounds including linalool, geraniol, geranial, neral, isoborneol, borneol, 1,8-cineol, 2pinen-5-o1, geranyl acetate, (E)-2-octenal, (E)-2-decenal, and (E)-2-dodecenal presented high values of avor dilution factor. Comparing our results with those in the literature, it seems that some differences in the volatile composition arise, which could be attributed to the geographic origin of ginger and the methods of extraction, such as SPME, supercritical uid extraction (Bartley and Jacobs, 2000) and the organic solvent (n-hexane) extraction (Nishimura, 1995).

3.2.

Effect of drying methods on volatile composition

The volatile components of the dehydrated ginger were compared with those found in fresh ginger (Table 1). It was shown that alkenes and aldehydes were the main components of dehydrated ginger. Nearly 90 alkenes in total were identied by GCMS. There were 59, 63, 61, 59, 65, and 50 components identied in total for AD at 50 C, AD at 60 C, AD at 70 C, MD at 60 W, VD in 13.3 kPa at 60 C, and FD in 0.203 kPa at chamber and condenser temperatures of 22 and 55 C, respectively. The volatile fractions of products produced by AD at 50 C, AD at 60 C, AD at 70 C, MD, VD, and FD were dominated by 1,3-cyclohexadiene,5-(1,5-dimethyl-4-hexenyl)-2methyl-,[S-(R*,S*)]- (accounting for 43.241%, 41.960%, 45.972%, 45.158%, 45.018%, and 41.461%, respectively), -farnesene (accounting for 10.029%, 10.954%, 11.107%, 11.724%, 11.496%, and 12.022%, respectively), cyclohexene,3-(1,5-dimethyl-4hexenyl)-6-methylene-,[S-(R*, S*)]- (accounting for 10.635%, 9.774%, 11.545%, 11.348%, 11.321%, and 11.542%, respectively), 2,6-octadienal,3,7-dimethyl- (accounting for 12.776%, 13.390%, 10.995%, 10.627%, 7.772%, and 15.118%, respectively)

and benzene,1-(1,5-dimethyl-4-hexenyl)-4-methyl- (accounting for 4.092%, 5.546%, 4.272%, 5.311%, 5.123%, and 5.396%, respectively). Song et al. (2003) have reported camphene, -myrcene, -phellandrene, borneol and -farnesene to be the key components of ginger avor. These volatiles were also found to be responsible for the aroma of ginger slices exposed to AD, MD, VD, and FD, and -farnesene was found to be the major component while camphene, -myrcene, -phellandrene, and borneol were found to be the minor components for the different drying methods. Chen and Ho (1988) have adopted liquid carbon dioxide to extract ginger oil from FD ginger power and examined volatile components of the ginger oil. Out of 168 characterized components 90 were identied and the highest amount of the geranial was zingiberene (35.0%), followed by -sesquiphellandrene (14.19%) and -bisabolene (13.35%). Compared with volatiles of fresh ginger, drying increased the relative contents of 1,3-cyclohexadiene,5(1,5-dimethyl-4-hexenyl)-2-methyl-,[S-(R*,S*)]-, -farnesene and cyclohexene,3-(1,5-dimethyl-4-hexenyl)-6-methylene,[S-(R*,S*)]-, and decreased the relative contents of 2,6-octadienal,3,7-dimethyl-, -phellandrene, camphene, eucalyptol, and 2,6-octadienal,3,7-dimethyl-,(Z). The increase of these compounds, rstly, was possibly due to synthetization of short-chain alkenes and isomerization of similar compounds. Secondly, since fresh ginger pulp was water-rich materials, whose moisture content was 94.52 0.30% (wet base), and moisture will restrict the volatile components to release completely. And it was more likely that moisture reduction and cell damage during the drying process resulted in greater release of these compounds. Macleod and Pieris (1984) have reported that both varieties of Sri Lankan ginger showed considerable decrease in monoterpene content and very high increase in sesquiterpene concentration and a number of the identied compounds have not previously been reported including trans--ocimene, thujyl alcohol, terpinen-4-ol, myrtenal, guaiene, -cubebene, -cadinene, and farnesol due to drying process. Comparing indicated that the volatiles in Laiwu ginger (in this study) and Sri Lankan ginger were not completely the same. This can be attributed to the origin of ginger and the methods of drying involved. The decrease in the relative concentration of some terpenes such as 1R--pinene, camphene, -myrcene, -phellandrene, and -phellandrene in dried ginger powder when compared to that of fresh ginger may be resulted from the change of conformation compounds and dehydration of oxygenated compounds. It is possible that the reduction reactions occurred during drying process and aldehydes was deoxidized to transform into corresponding alcohols, which promoted the esterication of alcohols with acetic acid produced by the thermal decomposition during drying. Therefore, the formation of 2,6-octadien-1-ol, 3,7dimethyl-,acetate,(Z)- could well explain the decrease of the relative content of 2,6-octadienal,3,7-dimethyl-,(Z) and 2,6octadienal,3,7-dimethyl-. AD, MD, VD and FD also resulted in the loss of cyclocompounds, alcohols (2-heptanol, eucalyptol, isoborneol, and borneol), aldehydes (octanal, 6-octenal,3,7-dimethyl-,(R)-, 6octen-1-ol, and 3,7-dimethyl-,(R)), and ketones (2-undecanone) which was more pronounced when temperature increased from 50 to 70 C in the case AD. These cyclocompounds includes tricyof [2.2.1.0(2,6)] heptane,1,7,7-trimethyl-, bicycle cle

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Table 1 Fraction (%) of volatiles of fresh and dried ginger slices. RTc (min) Compounds Fractiona (%) Freshb
2.67 3.53 3.61 5.51 7.85 7.98 8.71 8.82 8.83 8.91 9.04 9.50 9.60 10.01 10.22 10.30 10.43 10.29 10.34 10.56 10.68 11.03 11.15 11.33 11.39 11.40 11.40 11.52 11.58 11.76 11.82 11.82 11.93 11.98 12.00 12.80 12.90 13.73 13.78 13.79 14.50 14.56 14.83 15.54 15.65 15.96 15.93 15.96 16.23 16.83 16.85 17.07 17.33 17.33 17.47 18.38 19.07 19.66 19.93 20.63 21.35 21.36 21.55 Acetic acid Butanal,3-methylPentanal Hexanal 2-Heptanone 2-Heptanol Tricyclo[2.2.1.0(2,6)]heptane,1,7,7-trimethyl1R--pinene Bicyclo[4.1.0]hept-3-ene, 3,7,7-trimethyl-,(1S)Bicyclo[3.1.0]hexane,4-methyl-1-(1-methylethyl),didehydroderiv. 1S--pinene Camphene Bicyclo[2.2.1]heptane,2,2-dimethyl-3-methylene-,(1S)2,6-Dimethyl-1,3,5,7-octatetraene,E,EBicyclo[3.1.0]hexane, 4-methylene-1-(1-methylethyl)Bicyclo[3.1.0]hex-2-ene, 4-methyl-1-(1-methylethyl)Bicyclo[3.1.1]heptane, 6,6-dimethyl-2-methylene-,(1S)-Phellandrene -Pinene 5-Hepten-2-one,6-methyl-Myrcene Octanal -Phellandrene 1,4-Cyclohexadiene,1-methyl-4-(1-methylethyl)Bicyclo[4.1.0]hept-3-ene,3,7,7-trimethyl-,(1S)3-Carene 1,3,6-Octatriene,3,7-dimethyl1,3-Cyclohexadiene, 1-methyl-4-(1-methylethyl)Cyclohexene, 1-methyl-4-(1-methylethylidene)Benzene,1-methyl-3-(1-methylethyl)Benzene,1-methyl-2-(1-methylethyl)Benzene,1-methyl-4-(1-methylethyl)-Phellandrene Bicyclo[3.1.0]hex-2-ene,4-methyl-1-(1-methylethyl)Eucalyptol 2-Octenal,(E)Ethanone,1-(1H-pyrrol-2-yl)Cyclohexene,1-methyl-4-(1-methylethylidene)(+)-4-Carene 2-Nonanone 4,7-Methano-1H-indene,octahydroSantolina triene 1,3,6-Octatriene,3,7-dimethyl-,(Z)Bicyclo[2.2.1]heptan-2-one,1,7,7-trimethyl-,(1R)6-Octenal, 3,7-dimethyl-,(R)Bicyclo[2.2.1]heptan-2-ol,1,7,7-trimethyl-,formate,endoIsoborneol Borneol,heptauorobutyrate Borneol Benzene,1-methyl-4-(1-methylethenyl)Bicyclo[4.2.0]octa-1,3,5-triene,2,4-dimethyl3-Cyclohexene-1-methanol,,4-trimethyl(1R)-()-Myrtenal Bicyclo[3.1.1]hept-2-ene-2-carboxaldehyde, 6,6-dimethylDecanal 6-Octen-1-ol,3,7-dimethyl-,(R) 2,6-Octadienal,3,7-dimethyl-,(Z) 1,4-Cyclohexadiene, 3-ethenyl-1,2-dimethyl2-Decenal,(E)2,6-Octadienal,3,7-dimethylBornyl acetate Bicyclo[2.2.1]heptan-2-ol,1,7,7-trimethyl-, acetate,(1S-endo)2-Undecanone 0.033 0.185 0.116 1.835 0.011 6.675 0.012 0.073 0.194 0.785 0.102 0.381 0.061 0.025 0.310 0.057 7.532 5.658 0.310 0.166 0.458 0.170 1.678 0.033 0.973 0.138 0.185 5.561 0.165 15.713 0.230 0.286

AD50
0.058 0.039 t 0.145 0.559 t 0.031 0.011 0.212 0.084 0.059 t t 0.016 1.135 1.275 0.085 0.071 0.264 0.029 1.223 0.027 0.877 0.076 0.143 2.884 12.776 0.285 0.174

AD60
0.063 t 0.027 t 0.085 0.275 t 0.014 0.014 0.160 0.055 0.068 t t 0.019 1.477 0.571 0.071 0.150 0.039 0.254 0.020 0.713 0.225 0.490 0.173 3.121 0.118 13.390 0.188 0.373

AD70
0.081 0.025 t 0.107 0.372 t 0.019 t 0.158 0.064 0.043 t t 0.011 0.840 0.748 t 0.132 0.049 0.175 0.019 0.801 0.019 0.594 0.049 0.105 2.205 0.157 10.995 0.222 0.182

MD
0.011 0.018 t 0.111 0.345 t 0.016 0.013 0.123 0.065 0.045 t t t 0.012 0.713 0.419 0.039 0.014 0.030 0.187 0.015 0.680 0.019 0.538 0.130 2.918 10.27 0.179 0.271

VD
0.281 0.027 0.021 t 0.109 0.391 t 0.017 0.125 0.047 0.046 t 0.016 0.652 t 0.042 0.119 0.061 0.068 0.199 1.162 0.030 0.753 0.073 0.039 0.105 3.709 0.207 7.772 0.264 0.188

FD
0.065 0.181 0.083 0.013 0.100 0.039 t 0.020 0.201 0.404 0.037 0.064 0.039 0.029 0.040 0.271 0.834 0.029 0.029 0.149 2.724 15.118 0.208 0.158

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519

Table 1 (Continued) RTc (min) Compounds Fractiona (%) Freshb

22.80 24.35 24.48 24.50 24.53 25.37 26.68 26.71 26.82 1-Cyclobutanone,2-(2-methyl-1-propenyl) 1,3-Cyclohexadiene,1-methyl-4-(1-methylethyl)Cyclohexene,4-ethenyl-4-methyl-3-(1-methylethenyl)-1(1-methylethyl)-,(3R-trans)Bicyclo[4.1.0]hept-2-ene, 3,7,7-trimethyl(+)-4-Carene 2,6-Octadiene,2,6-dimethyl(+)-Cycloisosativene Cyclohexene,6-ethenyl-6-methyl-1-(1-methylethyl)-3-(1methylethylidene)-,(S)1,2,4-Metheno-1H-indene,octahydro-1,7a-dimethyl-5-(1methylethyl)-, [1S-(1,2,3a,4,5,7a,8S*)]-Cubebene Propanoic acid,2-methyl-,3,7-dimethyl-2,6-octadienyl ester,(E)()-Lavandulol, acetate 2,6-Octadien-1-ol, 3,7-dimethyl-,acetate,(Z)Bicyclo[4.1.0]hept-3-ene,3,7,7-trimethyl-,(1S)Cyclohexane,1-ethenyl-1-methyl-2,4-bis(1methylethenyl)-, [1S-(1,2,4)]1H-cyclopenta[1,3]cyclopropa[1,2]benzene, octahydro-7-methyl-3-methylene-4-(1-methylethyl)-, [3aS-(3a,3b,4,7, 7aS*)]Cyclohexane,1-ethenyl-1-methyl-2,4-bis(1methylethenyl)-, [1S-(1,2,4)]Copaene Bicyclo[3.1.1]heptane, 6-methyl-2-methylene-6-(4-methyl-3-pentenyl)-, [1R-(1, 5, 6)]Caryophyllene-(I1) 1H-cyclopropa[a]naphthalene,1a,2,3,5,6,7,7a,7boctahydro-1,1,7,7a-tetramethyl-, [1aR-(1a,7,7a,7b)]Aromadendrene 4,7-Methanoazulene,1,2,3,4,5,6,7,8-octahydro-1,4,9,9tetramethyl-,1S-(1,4,7.)]1H-cyclopenta[1,3]cyclopropa[1,2]benzene, octahydro-7-methyl-3-methylene-4-(1-methylethyl)-, [3aS-(3a,3b,4,7,7aS*)]1,6-Cyclodecadiene,1-methyl-5-methylene-8-(1methylethyl)-, [s-(E,E)]1H-cyclopenta[1,3]cyclopropa[1,2]benzene, octahydro-7-methyl-3-methylene-4-(1-methylethyl)-, [3aS-(3a,3b,4,7,7aS*)]-Elemene Bicyclo[3.1.1]hept-2-ene,2,6-dimethyl-6-(4-methyl-3pentenyl)1,3,6,10-Dodecatetraene, 3,7,11-trimethyl-,(Z,E)Ylangene 2H-2,4a-Methanonaphthalene,1,3,4,5,6,7-hexahydro1,1,5,5-tetramethyl-,(2S)Cyclohexene,6-ethenyl-6-methyl-1-(1-methylethyl)-3-(1methylethylidene)-,(S)1H-3a,7-Methanoazulene,2,3,4,7,8,8a-hexahydro-3,6,8,8tetramethyl-, [3R-(3,3a,7,8a)]1H-cycloprop[e]azulene,1a,2,3,4,4a,5,6,7b-octahydro1,1,4,7-tetramethyl-, [1aR-(1a,4,4a,7b)]1,4,7,-Cycloundecatriene, 1,5,9,9-tetramethyl-,Z,Z,Z-Caryophyllene cis--Bisabolene 0.026 0.118 0.089 0.122

AD50
t 0.123 0.133 0.364 0.126

AD60
t 0.135 0.160 0.160 0.125

AD70
0.019 t 0.121 0.103 0.105 0.302

MD
0.124 0.030 0.133 0.338

VD
t 0.273 0.150 0.469

FD
0.106 0.179 0.268

27.50 27.89 27.90 27.91 27.91 28.20

0.122 0.136 0.574

0.986 0.210 0.056

0.867 0.269

0.829 0.155

0.272 0.056

0.931 0.219 0.056

0.583 0.392 0.766

28.66

0.031

0.118

0.107

0.104

0.086

0.089

28.86

0.785

0.721

0.776

0.766

1.348

29.19 30.04

0.443

0.401

0.402

0.705 0.353

0.017 0.467

0.323

31.48 31.50

0.172

0.169

0.147

0.177

31.50 31.51 31.52

0.079

0.157

0.141 0.068

32.49

0.087

0.079

32.52

0.076

0.91

32.94 33.17 33.20 34.04 34.06 34.08 34.46

0.347 0.054

0.315 0.192 0.073

0.335 0.175 0.067

0.323 0.185 0.070

0.345 0.162 0.064

0.420 0.191 0.012 0.072 0.029

0.383 0.135

34.71

0.132

0.136

0.036

35.24 35.27 35.29

0.018

0.046

0.041

0.041

0.040

0.049

0.027

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Table 1 (Continued) RTc (min) Compounds Fractiona (%) Freshb

35.75 36.16 1,6,10-Dodecatriene, 7,11-dimethyl-3-methylene-,(E)1H-cycloprop[e]azulene,decahydro-1,1,7-trimethyl-4methylene-, [1aR-(1a,4a,7,7a,7b)](+)-Epi-bicyclosesquiphellandrene 1H-cyclopropa[a]naphthalene,1a,2,3,3a,4,5,6,7boctahydro-1,1,3a,7-tetramethyl-, [1aR-(1a,3a,7b)]Naphthalene, decahydro-4a-methyl-1-methylene-7-(1methylethylidene)-,(4aR-trans)Naphthalene,1,2,3,4,4a,5,6,8a-octahydro-7-methyl-4methylene-1-(1-methylethyl)-, (1,4a,8a)Tricyclo[5.4.0.0(2,8)]undec-9-ene, 2,6,6,9-tetramethylCopaene 1,6-Cyclodecadiene,1-methyl-5-methylene-8-(1methylethyl)-, [s-(E,E)]Benzene,1-(1,5-dimethyl-4-hexenyl)-4-methylNaphthalene,decahydro-4a-methyl-1-methylene-7-(1methylethenyl)-, [4aR-(4a,7,8a)] Naphthalene,2,3,4,4a,5,6-hexahydro-1,4a-dimethyl-7-(1methylethyl)1,3-Cyclohexadiene,5-(1,5-dimethyl-4-hexenyl)-2-methyl, [S-(R*,S*)]-Farnesene Naphthalene,1,2,3,4,4a,7-hexahydro-1,6-dimethyl-4-(1methylethyl)()--Panasinsen Cyclohexene,3-(1,5-dimethyl-4-hexenyl)-6-methylene-, [S-(R*,S*)]Naphthalene,1,2,4a,5,6,8a-hexahydro-4,7-dimethyl-1-(1methylethyl)-,(1,4a,8a)-Muurolene Cyclohexane,1-ethenyl-1-methyl-2-(1-methylethenyl)-4(1-methylethylidene)1H-3a,7-methanoazulene,2,3,4,7,8,8a-hexahydro-3,6,8,8tetramethyl-, [3R-(3,3a,7,8a)]1,6,10-Dodecatriene,7,11-dimethyl-3-methylene-, (Z,E)1H-benzocycloheptene,2,4a,5,6,7,8,9,9a-octahydro-3,5,5trimethyl-9-methylene-,(4aS-cis)0.251 0.072

AD50
0.773 0.343

AD60
0.583 0.285

AD70
0.770 0.318

MD
0.661 0.330

VD
0.679 0.344

FD
0.536 0.357

36.50 38.05

0.321

0.110

0.112

0.029 0.135

0.032

38.09 38.33

0.178 0.103

0.196

0.401 0.180

0.318 0.184

0.341 0.184

0.376 0.254

0.301 0.252

38.91 38.96 38.96

1.309

2.032

2.109

2.037

2.031

1.906

1.802

39.51 40.67

2.847 0.763

4.092 1.076

5.546 1.331

4.272 1.072

5.311 1.136

5.123 -

5.396 0.988

40.70 42.28

28.124

43.241

41.960

45.972

45.158

1.209 45.018

41.461

44.02 44.16 44.67 46.56 48.21 48.22 51.55 62.00

6.905 0.081

10.029 0.305 10.635 0.024

10.954 0.361 9.774 0.028

11.107 0.328 11.545

11.724 0.348 11.348 0.026

11.496 0.344 11.321 0.071 0.077

12.022 0.238

7.645

11.542 0.054

62.00 62.00

0.022

0.035

t, trace, the percentage of peak area of a component was less than 0.01%; , not detected.
a b

Fractions of components in fresh and dried ginger (%) = peak area of a component in ginger/total peak area of identied components in ginger. Fresh represents the fresh sample of ginger; AD50, AD60 and AD70 represent air drying at 50, 60 and 70 C; VD is vacuum drying at 60 C in 13.3 kPa; FD represents freezing drying in 0.203 kPa at chamber and condenser temperature of 22 and 55 C with pre-frozen at 80 C for 4 h; MD is microwave drying at 60 W. RT is retention time.

[3.1.0]hexane,4-methy-lene-1-(1-methyl-ethyl)-, cyclohexene, 1-methyl-4-(1-methylethyli-dene)-, cyclohexene,1methyl-4-(1-methylethyli-dene)-, bicycle[2.2.1]heptan-23-cyclohexene-1-methanol,, one,1,7,7-trimethyl-,(1R)-, 4-trimethyl-, cyclohexane,1-ethenyl-1-methyl-2,4bis(1-methylethenyl)-,[1S-(1,2,4 )]-. Indeed, most of cyclocompounds as mentioned above contain double bond, and therefore when ginger was exposed to heat in a circumstance where oxygen existed in abundance, oxidation reaction, degradation reaction and rearrangements occurred, which could lead to disappearance of some volatile constituents and to appearance of some novel molecules.

Seventy novel compounds in total were produced when ginger was dehydrated by different drying methods and 19, 28, 20, 19, 31, 20 new compounds were detected when ginger was dehydrated with AD at 50 C, AD at 60 C, AD at 70 C, MD at 60 W, VD in 13.3 kPa at 60 C and FD in 0.203 kPa at chamber temperature of 22 C, respectively. It indicated that AD at 60 C and VD in 13.3 kPa at 60 C resulted in more compounds. Higher temperatures could cause decomposition of compounds while lower temperatures pose adverse effects on formation of new compounds. Therefore, mild temperature (AD at 60 C, or VD at 60 C) could be recommended.

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3.3.

Results of principal components analysis

Average distance between clusters

1.6 1.4 1.2 1.0 0.8 0.6 0.4 0.2 FD AD60 VD MD AD70 AD50 Fresh

Six characteristic components of the ginger volatiles occurring in high quantities were used for the principal component analysis (Table 2 ). Their GCMS chromatograms were shown in Fig. 1. Table 3 showed that the cumulative contribution of the rst and the second principal components (prin1 and prin2) attained 90.61%, basically reecting the original of all variables. Therefore, the rst and the second principal components were selected to be the effective components during data analysis. The rst principal component (prin1) occupied 77.80% of total variation (Table 3) and was negatively correlated with 2,6-octadienal,3,7-dimethyl-,(Z) and 2,6-octadienal, 3,7-dimethyl- whereas positively correlated with benzene,1(1,5-dimethyl-4-hexenyl) -4-methyl-, 1,3-cyclohexadiene,5-(1, 5-dimethyl-4-hexenyl)-2-methyl-,[S-(R*,S*)]-, -farnesene, and cyclohexene,3-(1,5-dimethyl-4-hexenyl)-6-methy-lene-,[S(R*,S*)]- (Table 2). It indicated that, both of the relative content of 2,6-octadienal,3,7-dimethyl-,(Z) and 2,6-octadienal,3,7dimethyl- reduced while the relative content of benzene, 1-(1,5-dimethyl-4-hexenyl)-4-methyl-, 1,3-cyclohexadiene,5(1,5-dimethyl-4-hexenyl)- 2-methyl-,[S-(R*,S*)]-, -farnesene and cyclohexene,3-(1,5-dimethyl-4-hexenyl)-6- methylene,[S-(R*,S*)]- increased when the fresh ginger was dehydrated by AD, MD,VD and FD as compared to those in fresh ginger. However, the second principal component (prin2) was negatively correlated with the content of 2,6-octadienal,3,7dimethyl-,(Z), and 1,3-cyclohexadiene,5-(1,5-dimethyl-4hexenyl)-2-methyl-,[S-(R*,S*)]and highly correlated with the content of 2,6positively octadienal,3,7-dimethyland benzene,1-(1,5-dimethyl4-hexenyl)-4-methyl-. This could be explained that, as compared to other drying methods(AD, MD and VD), FD resulted in higher relative contents of 2,6-octadienal,3,7-dimethyland benzene,1-(1,5-dimethyl-4-hexenyl)-4-methyl- and lower relative contents of 2,6-octadienal,3,7-di- methyl-,(Z) and 1,3cyclohexadiene,5-(1,5-dimethyl-4-hexenyl)-2-methyl-,[S-(R*, S*)]-.

Name of observation or cluster

Fig. 2 Cluster analysis of six main compounds of ginger. Fresh is the volatiles of fresh fruit, and AD50, AD60 and AD70 represent volatiles of products by hot air drying at 50, 60 and 70 C, respectively; MD, VD and FD represent the volatiles of products by microwave drying at 60 W, vacuum drying at 60 C in 13.3 kPa and freezing drying in 0.203 kPa at chamber and condenser temperature of 22 and 55 C with pre-frozen at 80 C for 4 h.

the volatiles of fresh sample were greatly different from those of products produced by different drying methods. According to the similarity of volatile proles and the energy-saving, AD60 is preferable to FD in CL4 because FD consumed more energy than AD, and MD is preferable to VD in CL3 because MD has faster drying rate and higher content of volatiles (see Table 2), and in CL2, formed by CL3 and CL4, MD is preferable to AD60 still because of faster drying rate and higher content of volatiles in MD. Therefore, MD is a most favorable way to dry ginger, followed by AD at 60 C, VD at 60 C, FD, and AD at 70 and 50 C.

4.
3.4. Results of cluster analysis

Conclusions

In order to diagnose and characterize the correlation among the volatiles of fresh fruit and dried products produced by different drying methods, the resulting dendrogram (Fig. 2) was used for showing the similarity of volatile prole. The average distance method was used for cluster analysis. The higher the average distance the lower was the similarity of the samples. The dendrogram indicated that the data set could be regrouped into six clusters in total. The sixth cluster (CL6) included MD and VD (microwave drying at 60 W and vacuum drying at 60 C) with the lowest average distance of 0.3378, indicating both MD and VD have the highest similarity in volatile proles. The fth cluster (CL5) was formed by AD50 and AD70 (air drying at 50 and 70 C) with average distance of 0.3866, indicating higher (70 C) and lower (50 C) temperature resulted in the similar volatile proles, mild temperature (60 C) will result in different volatile prole. The fourth cluster (CL4) included AD60 and FD (air drying at 60 C and freezing drying) with average distance of 0.4511. CL5 and CL6 formed the third cluster (CL3) with average distance of 0.5662. And CL3 and CL4 formed the second cluster (CL2) with average distance of 0.6254. The rst cluster included fresh sample and CL2 with the highest average distance of 1.638, indicating that

Drying effect resulted not only in the disappearance of some volatile components but also in the appearance of others which were absent in fresh ginger pulp. Seventy novel compounds in total and 19, 28, 21, 20, 31, 20 new compounds were produced by AD at 50 C, AD at 60 C, AD at 70 C, MD at 60 W, VD in 13.3 kPa at 60 C and FD in 0.203 kPa at chamber temperature of 22 C, respectively. Aldehydes and alkenes play the most important role in ginger aroma. The volatiles produced by AD at 50 C, AD at 60 C, AD at 70 C, MD, VD and FD were dominated by 1,3cyclohexadiene,5-(1,5-dimethyl-4-hexenyl)-2-methyl-,[S-(R*, S*)]-, -farnesene, cyclohexene,3-(1,5-dimethyl-4-hexenyl)6-methylene-,[S-(R*,S*)]-, 2,6-octadienal,3,7-dimethyl-, and benzene,1-(1,5-dimethyl-4-hexenyl)-4-methyl-, respectively. The effect of AD, MD, VD and FD also resulted in the loss of cyclocompounds, alcohols (2-heptanol, eucalyptol, isoborneol, and borneol), aldehydes (octanal, 6octenal,3,7-dimethyl-,(R)-, 6-octen-1-ol, and 3,7-dimethyl,(R)), and ketones (2-undecanone). Both the rst and the second principal components almost reected the prole of all variations (90.61%). The rst principal component indicated that when the fresh ginger was dehydrated by AD, MD, VD and FD the relative contents of benzene,

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Table 2 Principal component analysis of six main volatile compounds. Compounds Fractiona (%) Freshb
2,6-Octadienal, 3,7-dimethyl-,(Z) 2,6-Octadienal, 3,7-dimethylBenzene,1-(1,5-dimethyl-4-hexenyl)-4methyl1,3-Cyclohexadiene,5-(1,5-dimethyl-4hexenyl)-2-methyl-[S-(R*,S*)] -Farnesene Cyclohexene,3-(1,5-dimethyl-4-hexenyl)6-methylene-, [S-(R*,S*)] Total fraction
a b

Eigenvectors AD60
3.12 13.39 5.55 41.96 10.95 9.77

AD50
2.88 12.78 4.09 43.24 10.03 10.64

AD70
2.20 11.00 4.27 45.97 11.11 11.54

MD
2.92 10.27 5.31 45.16 11.72 11.35

VD
3.71 7.77 5.12 45.02 11.50 11.32

FD
2.72 15.11 5.40 41.46 12.02 11.54

Prin1c

Prin2

5.56 15.71 2.85 28.12 6.90 7.64

0.407052 0.327373 0.298284 0.870313 0.381838 0.297115 0.450060 0.134859 0.449877 0.169929 0.441126 0.006482

66.78

83.66

84.74

86.09

86.73

84.44

88.25

Fractions of components in fresh and dried ginger (%) = peak area of a component in ginger/total peak area of identied components in ginger. AD50, AD60 and AD70 represent air drying at 50, 60 and 70 C; VD is vacuum drying at 60 C in 13.3 kPa; FD represents freezing drying in 0.203 kPa at chamber and condenser temperature of 22 and 55 C with pre-frozen at 80 C for 4 h; MD is microwave drying at 60 W. Prin1 and prin2 represent the rst and the second principal components.

Fig. 1 GCMS chromatograms of ginger products. Letters in the upper left corner of each picture (ag) stand for the chromatogram of fresh ginger pulp and different dried ginger powders obtained by hot air drying at 50, 60 and 70 C, microwave drying, vacuum drying and freezing drying, respectively. The digitals (16) on the six bigger peaks stand for 2,6-octadienal,3,7-dimethyl-,(Z), 2,6-octadienal,3,7-dimethyl-, benzene,1-(1,5-dimethyl-4-hexenyl)-4-methyl-, 1,3-cyclohexadiene,5-(1,5-dimethyl-4-hexenyl)-2-methyl-[S-(R*,S*)]-, -farnesene and cyclohexene,3-(1,5-dimethyl-4-hexenyl)-6-methylene-, [S-(R*,S*)]-, respectively.

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523

Fig. 1 (Continued )

Table 3 Eigenvalues of the principal components and their contribution and cumulative contribution. Eigenvalue
Prin1a Prin2 Prin3 Prin4 Prin5 Prin6
a

Difference
3.92055876 0.31112094 0.33663694 0.10452675 0.00552842

Proportion
0.7798 0.1263 0.0745 0.0184 0.0010 0.0000

Cumulative
0.77798 0.9061 0.9806 0.9990 1.0000 1.0000

4.67862838 0.75806962 0.44694868 0.11031174 0.00578500 0.00025657

Prin represents the principal component, the order is from the rst to the sixth.

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1-(1,5-dimethyl-4-hexenyl)-4-methyl-, 1,3-cyclohexadiene,5(1,5-dimethyl-4-hexenyl)- 2-methyl-,[S-(R*,S*)]-, -farnesene and cyclohexene,3-(1,5-dimethyl-4-hexenyl)-6- methylene,[S-(R*,S*)]- increased and that of 2,6-octadienal,3,7-dimethyl,(Z) and 2,6-octadienal,3,7-dimethyl- decreased as compared to those in fresh ginger. And the second principal component meant that, as compared to other drying methods, FD resulted in higher relative contents of 2,6-octadienal,3,7-dimethyl- and benzene,1-(1,5dimethyl-4-hexenyl)-4-methyl- and lower relative contents of 2,6-octadienal,3,7-dimethyl-,(Z) and 1,3-cyclohexadiene,5(1,5-dimethyl-4-hexenyl)-2- methyl-,[S-(R*, S*)]-. Cluster analysis indicated that MD was the most favorite drying way, followed by AD at 60 C, VD at 60 C, FD, and AD at 70 and 50 C.

Acknowledgements
The study was supported by State High-tech R&D Program of China (863 Program) (2011AA100802). It was also supported by National Basic Research Program of China (973 Program) (2012CB720805).

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