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Procedia Engineering 37 (2012) 240 - 249
The Second SREE Conference on Engineering Modelling and Simulation (CEMS 2012)
Analysis of Volatile Components from Dictyophora rubrovolota Zang, ji et liou
Ming-Quan Hang a,ba*, Qing-Qing Zou a, Hong-Yu Tian a,b, Bao-Guo Sun a,b, Hai-Tao Chen a,b
aSchool of Food and Chemical Engineering, Beijing Technology and Businesss University,
No. 11, Fucheng Road, Haidian district, Beijing 100048, China bBeijing Key laboratory of Flavor Chemistry, Beijing Technology and Businesss University, _No. 11, Fucheng Road, Haidian district, Beijing 100048, China_
Abstract
Volatile compounds extracted by simultaneous distillation and extraction (SDE) from Dictyophora rubrovolota Zang, ji et liou were analyzed by gas chromatography-mass spectrometry (GC-MS), and the aroma-active volatiles were identified by aroma extract dilution analysis (AEDA) method with gas chromatography-olfactometry (GC-O). 82 volatile components were identified by GC-MS, including 11 aldehydes, 10 ketones, 6 alcohols, 2 hydroxybenzenes, 9 esters, 19 acids, 14 hydrocarbons, and 11 other compounds. By GC-O analysis, 22 aroma-active compounds were identified, among which seven key flavor volatiles with high flavour dilution factor (FD) ranging from 27 to 3 included 2,3-pentanedione (FD 27, 0.074 mg/kg , yogurt flavor), acetic acid (FD 27, 12.72 mg/kg, sharp acidity), 2-methylbutanoic acid (FD 27, 1.039 mg/kg, smelly socks smell, aldehyde taste), (E)-2-octenal (FD 9, 0.066 mg/kg, pine oil odour), 2-phenyl-2-butenal (FD 9, 0.12 mg/kg, astringent taste, aldehyde flavor, fragrant beans), benzaldehyde (FD 3, 0.136mg/kg, formaldehyde smell, resin taste), 3,5-diethyl-2-methyl-pyrazine (FD 3, 0.082 mg/kg, musty, bark corrupt taste, smelly).
© 2012 Published by Elsevier Ltd. Selection
Keywords: Dictyophora rubrovolota Zang, ji et liou; volatile components; GC-MS; GC-O; AEDA
* Corresponding author. Tel.: +86-010-68985219; fax: +86-010-68985219. E-mail address: hmqsir@163.com; huangmq@th.btbu.edu.cn.
1877-7058 © 2012 Published by Elsevier Ltd. doi:10.1016/j.proeng.2012.04.234
1. Introduction
Dictyophora rubrovolota Zang, ji et liou is a genus of dictyophora indusiata [1,2], which in China are also named as "Zhu sun". The wild Dictyophora rubrovolota Zang, ji et liou mainly grows in humus of bitter bamboo forest in Guizhou province, Yunnan province and Sichuan province [1]. There are eleven kinds of dictyophora indusiata reported in the world, and seven are growing in China. Meanwhile, in china there are only four dictyophora indusiatas in market which are often used as a food for its delicious taste, rich nutrition and unique flavor[3,4], for they has been cultivated successfully and made cheaper and more available. They are Dictyophora indusiata Fisch, Dictyophora duplicata (Bosc) E. Fish, Dictyophora Echinovolvata Zang, Zheng et Hu, Dictyophora rubrovolota Zang, ji et liou. Before, we have researched Dictyophora Echinovolvata Zang, Zheng et Hu, now the flavor of Zheng et Hu, Dictyophora rubrovolota Zang, ji et liou would be researched.
At present, the researches about Dictyophora rubrovolota are mainly involved in the aspects of cultivation [5-7], nutrient components and its efficacy [8, 9], culture preservation & distribution characteristics [1, 2], polysaccharides extraction & the antitumor effect of poilsaccharides [10,11]. However, the aroma-active compounds of extracts of Dictyophora rubrovolota have not been reported. It interests us to investigate the aroma-active components of Dictyophora rubrovolota since those dishes made of them usually present a very specific and delicate flavor. Herein, the volatile components of Dictyophora rubrovolota were extracted by SDE and analyzed by GC-MS, the aroma-active compounds among which were identified by AEDA and GC-O.
2. Materials and Methods
2.1. Materials and Chemicals
Dried embryo of Dictyophora rubrovolota Zang, ji et liou were purchased from the local market of Guiyang city, Guizhou province, and was identified by Kunming Institute of Botany, Chinese Academy of Science, Kunming. The voucher specimen number was Huang Mingquan 2011-02.
Dichloromethane (anhydrous, 99.5%), diethyl ether (99.8%) and sodium carbonate (anhydrous) were purchased from Sinopharm Chemical Reagent Co. Ltd (Beijing, China). n-alkanes (C7-C30) and the reference compounds listed in Table 1 were purchased from Sigma and Aldrich (Steinheim, germany).
2.2. Isolation of Volatiles by SDE
The Likens-Nickerson apparatus was used to extract the dried embryo of Dictyophora rubrovolota Zang, ji et liou. 35 g of dried Dictyophora rubrovolota Zang, ji et liou were placed in 2000mL round bottom flask mixed with 1L distilled water. The distillation was performed for two times using the same solvent, each time for 3h (an experience value) after refluxing with fresh solvent of 90mL. Dichloromethane and diethyl ether were used respectively in this experiment as extraction solvent. Then the two extracts were combined, dried over by anhydrous sodium sulfate (25g) for 12h, then filtrated by common glass filler and concentrated to approximately 0.5 mL by a revolving evaporator (not heated), then the sample was preserved for analysis in refrigerator with the temperature of -20 °C.
2.3. Analysis by GC-MS
Mass spectra data were obtained with an Agilent 6890N-5973i and Thermo Trace GC Ultra-DSQII. The corresponding analysis conditions were as the followings.
Agilent 6890N-5973i: electron ionization source, 70eV, ion source temperature 230°C; electric quadrupole 150°C; transfer line temperature 250°C; full scan, mass range 29-450; capillary column DB-Wax (30m*0.25mm*0.25^m); oven temperature 35°C for 1min, with 18°C/min to 53°C, retaining 12min, then 5°C/min to 57°C, retaining 3min, then 4°C/min to 100 °C, retaining 6min, and then 5°C/min to 150°C, retaining 6min, 7°C/min to 220 °C, retaining 13.5°C, final 6°C/min to 240 °C, retaining 15min; carrier gas, helium (99.999%); constant flow rate 1.0mL/min; injector temperature, 250°C; splitless; injector volumn,1^L; solvent delay,5.6min.
Thermo Trace GC Ultra-DSQII: ion source temperature 250°C; capillary column RTX-5 (30m*0.25mm*0.25^m); oven temperature 35°C for 1min, with 18°C/min to 53°C, retaining 5min, then 2°C/min to 100°C, then 6°C/min to 186°C, retaining 6min, final 8°C/min to 280°C, retaining 5min; injector temperature, 260 °C; solvent delay, 3.3min; the others as the same above.
Compounds were identified by first comparing their mass spectra with NIST 2008 mass spectra database and then comparing the RI (retention index) values relative to C7-C30 n-alkanes with the published. When accessible, identifications were further confirmed with authentic chemicals.
The amounts of some compounds which had gained authentic chemicals were calculated by external standard methods in GC, the others were getted in GC by relating peak areas to that of pentadecane (2.32 mg/mL, diethyl ether as solvent) internal standard using a response factor of 1. Every amount was the average obtained by three analyses.
2.4. Odor Analysis by GC-O
GC-O analysis was carried out on an Agilent 6890N GC coupled with a capillary column DB-Wax (30m*0.25mm*0.25^m).The SDE concentrates (1^L) were injected at 250°C in splitless mode; Oven temperature and carrier gas were identical to those of GC-MS analysis. The column effluent was divided (1:1) between the flame ionization detector (FID) and the olfactometer (Sniffer 9000, Brechbuhler Scientific Analytical Solutions INC, Switzerland ) by one 'Y'shape glass splitter. The effluent to the odor port was enclosed with a stream of humidified air of 10mL/min and transferred to the glass detection cone by one length of capillary at the temperature of 220 °C.
Five trained assessors, including two flavourists, were selected to smell and record the odor descriptions for the GC-O experiment following the way of Guillard, et al [12]. Retention times of the odor responses were converted into retention index values using the retention time of a series of n-alkanes (C7-C30).
3. Results and Discussion
3.1. SDE/GC-MSAnalysis
Simultaneous distillation and extraction apparatus was used to extract the volatiles from Dictyophora rubrovolota Zang, ji et liou for the reason that the method of simultaneous distillation and extraction (SDE) is an exhaustive extraction method, and a 'total volatile analysis' result can be obtained[13,14]. Moreover, the method of SDE can simulate the cooking process of delicacies in which dictyophora indusiata is an indispensible ingredient, and ensures that the volatiles generated and extracted are the natural flavors from delicacies made of dictyophora indusiata. With GC-MS, identification and quantitative analysis of volatile compounds extracted by SDE from Dictyophora rubrovolota Zang, ji et liou were present in table 1.
Eighty two volatile components were identified in total, including 11 aldehydes, 10 ketones, 6 alcohols, 2 hydroxybenzenes, 9 esters, 19 acids, 14 hydrocarbons, and 11 other compounds. Among these
identifided volatiles, the prominent components were (Z,Z)-9,12- octadecadienoicacid (132.3 mg/kg), n-hexadecanoic acid (42.10 mg/kg), pentadecanoic acid (36.20 mg/kg), acetic acid (12.72 mg/kg), and so on.
19 acids were found in this experiment and the total content of the acids was 241.5 mg/kg, representing 88.10% of 82 volatiles and ranking the predominant. Among the volatile acids, (Z, Z)-9, 12-octadecadienoic acid (132.3 mg/kg) was the largest followed by n-hexadecanoic acid (42.1 mg/kg), pentadecanoic acid (36.2 mg/kg), et al. These short carbon-chain acids and long carbon-chain acids were in possible respectively derived from the oxidation of corresponding aldehydes and hydrolysis of corresponding lipids during the extraction.
Ten ketones were identified and the total amount was 16.034mg/kg, accounting 5.85% of the all identified compounds. Acetion was the largest (12.20 mg/kg) followed by natural musk ambrette (2.337 mg/kg), 4-hydroxy-2-butanone (0.823 mg/kg), and coffee furanone (0.235 mg/kg), et al. Albaflavenone, a sesquiterpene antibiotic, is secondary found in dictyophora indusiata after we have firstly seperated and identified it from Dictyophora indusiata (Vent:Pers.) Fischer, which will be reported in the other journal. The other ketones may be formed by the oxidative degradation of unsaturated fatty acid, for instance, the oxidative decomposition of linoleic acid[15]. Acetion may be come from the degradation of glycogen [16]. Natural musk ambrette (oxacycloheptadec-8-en- 2-one) was a marcolactone , it may be produced by the lactonization of ambrettolic acid or derived from the acid of 6, 16-dihydroxyhexadecanoic acid which could dehydrate into the isoambrettolic aic[17]. Coffee furanone was probably generated by Maillard reaction during the SDE [18].
Eleven aldehyde compounds whose total content was 4.267 mg/kg were identified from the SDE extract, representing 1.56% of the identified volatiles. The furfural (1.815 mg/kg) was the largest followed benzeneacetaldehyde (0.925 mg/kg), hexanal (0.479 mg/kg) , heptanal (0.365 mg/kg), et al. Aroma aldehydes (benzeneacetaldehyde, benzaldehyde and 2-phenyl-2-butenal) are possibly connect to amino acid degradation [19], e.g benzeneacetaldehyde that was a Strecker aldehyde from 2-phenylalanine degradation and had also been detected in many SDE extract[4] and was produced by heating [20]. The aliphalic aldehydes including saturated and unsaturated aldehydes may be arise from the oxidation degradation of unsaturated fatty acids. For example, hexanal may come from the oxidative decomposition of linoleic acid [15, 21].
Six alcohols were found, representing 0.77% of the identified volatiles with the total content of 2.111 mg/kg. n-Bisabolol (0.829 mg/kg) was the largest followed by 2,3-butanediol (0.396 mg/kg), phenylethyl alcohol (0.378 mg/kg), nerolidol (0.203 mg/kg), et al. n-Bisabolol and nerolidol might be characteristic products of the metabolism of Dictyophora rubrovolota Zang, ji et liou during growing-up, and n-
bisabolol did not be found in Dictyophora indusiata Fisch [4] and Dictyophora echinovolvata Zang, Zheng et Hu [22-24].
Nine esters were identified from the SDE extract in total, the content of esters was 2.156 mg/kg and the proportion was 0.79%, with 1-methoxy-2-propyl acetate (0.431 mg/kg) as the largest followed 9,12-hexadecadienoicacid methyl ester (0.361 mg/kg), 9,12-octadecadienoicacid ethyl ester (0.319 mg/kg), ethyl 9-hexadecenoate (0.282 mg/kg), et al. These esters can be come from the interaction of alcohols and free carboxylic acids which can be derived from decomposition of lipids.
Six nitrogen compounds including 5 pyrazines and 1 pyrrole were found from the SDE extract, they were tetramethyl pyrazine (1.893 mg/kg), trimethyl pyrazine (0.501 mg/kg), 2-acetylpyrrole (0.472 mg/kg), 2,3,5-trimethyl-6-ethylpyrazine (0.085 mg/kg), 3,5-diethyl-2-methylpyrazine (0.082 mg/kg) and 2,3-dimethylpyrazine (0.075 mg/kg), and these six nitrogen compounds accounts for 1.13% of 82 volatiles. Nitrogen compounds such as 2-acetylpyrrole might result from Maillard reaction [18] and it have been reported that Dictyophora rubrovolota riches in amino acid, protein, polysaccharide, vitamine [9] which are the critical ingredients for Maillard reaction.
Above all, One sulfur compound (dibenzothiophene. 0.766 mg/kg) was found and this sulfur compound may be derived from sulfur-containing amino acid, such as cysteine [25]. 11 aliphalic hydrocarbons and 3 aromatic hydrocarbons, fourteen hydrocarbons were found in total by SDE/GC-MS, accounting for 0.80% of the identified compounds with the content of 2.197mg/kg. Four oxygen compounds were found, among these, 1,1-diethoxy ethane (1.211 mg/kg) was the largest. Two hydroxybenzenes were found, including phenol (0.111 mg/kg) and 2, 4-bis (1, 1-dimethyl)-phenol (0.027 mg/kg), representing 0.05% of the 82 volatiles.
Table 1 Volatile components identified in Dictyophora rubrovolota Zang, ji et liou extracted by SDE and analyzed by GC-MS
Retention Index
DB-Wax RI/aRI
RI/RT(Refer.)
Compounds
Amount (mg/kg)
Identification method
Aldehydes Subtotal 4.267
1049/1064 hexanal 0.479 MS,RI,S
1149/1182 908/901 [26] heptanal 0.365 MS,RI
1381/1377 1062/1063[27] (E)-2-octenal 0.066 MS,RI,S
1406/1447 848/848[28] furfural 1.815 MS,RI,S
1453/1496 benzaldehyde 0.136 MS,RI,S
1511 971.3/972[29] 5 -methyl-furfural 0.144 MS,RI
1580/1623 1052/1051 [30] benzeneacetaldehyde 0.925 MS,RI,S
1711/1710 1327/1325 [31] (E,E)-2,4-decadienal 0.113 MS,RI,S
1871 1281/1281[28] 2-phenyl-2-butenal 0.120 MS, RI
1106/1108[32] nonanal 0.046 MS,RI,S
1299 2,4-nonadienal 0.058 MS
Ketones Subtotal 16.03
1028/1056 2,3-pentanedione 0.074 MS,RI,S
1230 coffee furanone 0.235 MS,S
1253/1286 749 acetoin 12.20 MS,RI,S
1440/1497 2-acetyl furan 0.046 MS,RI
1531 4-hydroxy-2-butanone 0.823 MS
1560 butyrolactone 0.100 MS
1980 dihydro-5-pentyl-2(3H)-furanone 0.111 MS
1465 2,3-dimethylchromone 0.057 MS
2173 1713 albaflavenone 0.051 MS, S
2982 2060 natural musk ambrette 2.337 MS
Alcohols Subtotal 2.111
1262 acetone alcohol 0.122 MS
1457 2,3-butanediol 0.396 MS
1607/1573 2-furanmethanol 0.183 MS,RI,S
1852 1123/1120[33] phenylethyl alcohol 0.378 MS,RI,S
2014/2050 nerolidol 0.203 MS,RI,S
2192 1700 nbisabolol 0.829 MS
Esters Subtotal 2.156
1342 900 2,3-butanediol diacetate 0.092 MS
1516 940 1-methoxy-2-propyl acetate 0.431 MS
1565 1057 2-methyl-propanoic acid, ethyl ester 0.100 MS
2203 1900/1901[34] hexadecanoic acid, methyl ester 0.053 MS,RI
2277 ethyl 9-hexadecenoate 0.282 MS
2477 2113 (E,E)-9,12-octadecadienoic acid, methyl ester 0.274 MS
946 3-hydroxy-butanoic acid ethyl ester 0.244 MS
2094 9,12-hexadecadienoic acid, methyl ester 0.361 MS
2178 9,12-octadecadienoic acid, ethyl ester 0.319 MS
Acids Subtotal 241.5
1385/1435 711/660[35] acetic acid 12.72 MS,RI,S
1513 2-methyl-propanoic acid 0.288 MS
1576 butanoic acid 0.114 MS
1617 2-methyl-butanoic acid 1.039 MS,S
1784 hexanoic acid 0.217 MS,S
2027/2075 1208/1201[28] octanoic acid 0.357 MS,RI,S
2139/2177 1297/1297[32] nonanoic acid 0.118 MS,RI
2232 3-nonenoic acid 0.040 MS
2240 n-decanoic acid 0.081 MS
2401 undecylenic acid 0.138 MS
2450 1580/1580[27] dodecanoic acid 0.385 MS,RI
2498 cis-5-dodecenoic acid 0.277 MS
2556 1674/1678[27] tridecanoic acid 0.278 MS,RI
2672 1778/1777[36] tetradecanoic acid 9.144 MS,RI
2795 1900 pentadecanoic acid 36.20 MS
2838 14-pentadecenoic acid 4.803 MS
2909 2054 n-hexadecanoic acid 42.10 MS,S
3000 oleic acid 0.864 MS,S
2228/2236[37] (Z,Z)-9,12-octadecadienoic acid 132.3 MS,RI
Hydrocarbons Subtotal 2.197
1091/1122 860 ethylbenzene 0.150 MS,RI
1105 871 p-xylene 0.161 MS
2685 1821 phenanthrene 1.021 MS
894.6[38] nonane 0.117 MS,RI,S
992 [38] decane 0.100 MS,RI,S
1192[38] dodecane 0.166 MS,RI,S
1203/1213[39] 2,6-dimethy undecane 0.022 MS,RI
1292 tridecane 0.047 MS,RI,S
1415 6-dodecene 0.018 MS
1428/1422[40] (+)-|3-cedrene 0.007 MS,RI
1448 calarene 0.097 MS
1540 cis-a-bisabolene 0.092 MS
1655 1,E-11,Z-13-octadecatriene 0.137 MS
1690 heptadecane 0.062 MS,RI,S
Nitrogen compounds Subtotal 3.108
1302/1335 2,3-dimethyl-pyrazine 0.075 MS,RI,S
1362/1391 1006/1005[41] trimethyl-pyrazine 0.501 MS,RI
1422/1457 1087/1089[42] tetramethyl-pyrazine 1.893 MS,RI,S
1460 1175 3,5-diethyl-2-methyl-pyrazine 0.082 MS
1157/1163[42] 2,3,5-trimethyl-6-ethylpyrazine 0.085 MS,RI
1920/1952 2-acetylpyrrole 0.472 MS,RI
Others Subtotal 2.757
730/725[44] 1,1-diethoxy ethane 1.211 MS,RI
839 2-ethyl-1,3-dioxolane 0.110 MS
1398 996 1,3-dioxolane,2-methoxymethyl-2,4,5-trimethyl- 0.205 MS
1515 2,4-bis( 1, 1 -dimethyl)-phenol 0.027 MS
1962/1996 phenol 0.111 MS,RI,S
2116 1666 a-bisabololoxide B 0.327 MS
2628 1794/1780[43] dibenzothiophene 0.766 MS,RI
aDB-Wax RI: Reference RI, which were all attained from the the web site of http://www.odour.org.uk
'Identification method: MS, compared with Nist08 Mass Spectral Database; RI, agree with retention index of literatures; S, compared with retention indexes and mass spectra of the authentic chemicals.
3.2. Gas Chromatography-Olfactometry Analysis
GC-O analysis was done to find out the aroma-active compounds which played the key role on the distinctive flavor of Dictyophora rubrovolota Zang, ji et liou. The results was presented in Table 2.
With FD ranging from 1-27, 22 aroma-active compounds were identified, which may make the particular flavor of this fungi. Among these identified compounds, seven key flavor volatiles with high FD ranging from 27 to 3 included 2,3-pentanedione (FD 27, yogurt flavor), acetic acid (FD 27, sharp acidity), 2-methylbutanoic acid (FD 27, smelly socks smell, aldehyde taste), (E)-2-octenal (FD 9, pine oil odour), 2-phenyl-2-butenal (FD 9, aldehyde flavor, fragrant beans), benzaldehyde (FD 3, formaldehyde smell, resin taste), 3,5-diethyl-2-methyl-pyrazine (FD 3, musty, bark corrupt taste, smelly).There were seven unknown compounds which had odours, such as fragrant flavor, peanut candy, sweet (FD 3) and sour, fruit sweet, rice wine fragrant (FD 9), which mainly came out from the GC-O at the period of solvent delay in GC-MS, and so could not be identified. Odors such as mushroom flavor (FD 3) were not
identified by GC-MS for its too weak singal. Compounds with Log3FD factor of <1 were considered to make only minor contributions to the overall aroma.
Comparing the results gained by SDE/GC-MS, thought the amount of (Z, Z)-9, 12- octadecadienoic acid (132.3 mg/kg) was the highest in the volatile, it had little contribution to peculiar flavor of
Dictyophora rubrovolota Zang, ji et liou. The same were other long-chain fatty acid.
Table 2 Aroma-active compounds in the flavor of dried mushroom of Dictyophora rubrovolota Zang, ji et liou by AEDA
No. Rentation index Compound Odour description Log3FD factor
1 921 unknown fragrant flavor, peanut candy, sweet and sour 1
2 953 unknown fruit sweet, rice wine fragrant 2
3 963-970 2,3-pentanedione yogurt flavor 3
4 998 hexanal green tea flavor, fresh leave flavor <1
5 1048 heptanal leafy <1
6 1136 unknown smells like the gas of heated gas in oven <1
7 1263 unknown smelly with sharp acidity odour 1
8 1273 unknown mushroom 1
9 1328-1338 2,3-dimethylpyrazine roasted rice flavor <1
10 1372 (E)-2-octenal pine oil odour 2
11 1382 acetic acid sharp acidity odour 3
12 1398 unknown pine oil odour, sour odour 1
13 1404 furfural roasted potato or tomato <1
14 1420 tetramethylpyrazine dictyophora flavor <1
15 1473 2-acetyl furan greasy <1
16 1480 benzaldehyde formaldehyde smell, resin taste 1
17 1518 3,5-diethyl-2-methyl-pyrazine musty, bark corrupt taste, smelly 1
18 1529 5-methyl-furfural flower sweet <1
19 1550 2-methyl-propanoic acid baked sweet <1
20 1609-1625 2-furanmethanol sauce fragrant, flower <1
21 1663-1684 2-methyl-butanoic acid smelly socks smell, aldehyde taste 3
22 1715 unknown earthy, wood scent <1
23 1759 (E,E)-2,4-decadienal licorice flavor, fatty <1
24 1785 hexanoic acid aldehyde, oil flavor <1
25 1868-1891 2-phenyl-2-butenal astringent taste, aldehyde flavor, fragrant beans 2
26 1981 2-acetylpyrrole mugwort leafy 1
27 2020 2(3H)-furanone,dihydro-5-pentyl- fatty <1
28 2163 nonanoic acid faint acidity flavor <1
29 2179 isolongifolen-5-one pleasant wood flavor <1
FD: Flavour dilution factor. The concentrated sample was diluted by ethyl ether. The ratios were 1:3, 1:9, 1:27, 1:81,
corresponding to FD factors of 3, 9, 27, 81, respectively.
Acknowledgement
Financial support from Beijing Natural Science Foundation Program and Scientific Research Key Program of Beijing Municipal Commission of Education (KZ201110011015), the National Natural Science Foundation of P. R. China (No. 31071610 and No. 31101350) and PHR (IHLB) (PHR20090504) is gratefully acknowledged.
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