INTRODUCTION Banana is an important tropical fruit crop used mainly for dessert and culinary purposes. Ripe fruits are ideal for beverage preparation owing to high Total Soluble Solids (T.S.S.) content (21-24°B), medium acidity (0.4-0.6%) and pleasant flavour (Pe´rez et al, 1997). Fermented banana beverages with 5-7% alcohol are popular conventional products in the African countries and, further, quality enhancement of the beverage is reported in scientific literature (Iwuoha and Eke 1996; Akubor et al, 2003; Aurore et al, 2009; Carvalho et al, 2009). Fermented fruit beverages are distinct from unfermented fruit juices as these possess a unique flavour due to synthesis and molecular rearrangement of esters, carbonyl compounds, alcohols and fatty acids during fermentation, clarification and subsequent storage (Rapp and Mandery, 1986). Extensive research has been done on flavour profile of the banana fruit, and scientists have documented banana flavour as a varietal character. Major flavour principles in the banana are: esters, carbonyl compounds, free alcohols and short-chain organic acids (Mattei, 1973; Marriott, 1980; Macku and Jennings, 1987). However, there is no information published to date on aroma profile of the banana wine. This study describes J. Hortl. Sci. Vol. 8(2):217-223, 2013 1Division of Plant Physiology and Biochemistry, IIHR, Bangalore Aroma profile of fruit juice and wine prepared from Cavendish banana (Musa sp., Group AAA) cv. Robusta K. Ranjitha, C.K. Narayana and T.K. Roy1 Division of Post Harvest Technology Indian Institute of Horticultural Research Hessaraghatta Lake Post, Bangalore - 560089, India E-mail: ranjitha@iihr.ernet.in ABSTRACT A comparative study of the aroma profile of an alcoholic beverage (wine) and natural juice from banana cv. Robusta was performed. The study showed disappearance and synthesis of many aroma compounds during the fermentation process. Relative abundance of carbonyl compounds was high in the juice, and carboxylic acid content was higher in the wine. Aroma signature compounds of banana juice, isoamyl acetate, butyl isovalerate, isopentyl isovalerate, trans- 2- hexenal and butanoates were present only in a low proportion in the wine, while decanoic, dodecanoic and hexa decanoic acids (as well as their esters) were abundant in the banana wine. Synthesis compounds like methyl nonyl ketone, isoeuginol and 2-methoxy 4-vinyl phenol was greater during fermentation. Elemicin was present in high quantity in both the juice and the wine. Key words: Banana wine, head-space volatiles, esters, fermentation-derived aroma, SPME method aroma profile of a high-quality fermented beverage compared with unfermented juice of the banana in a commercially important Cavendish cultivar, Robusta. MATERIAL AND METHODS Preparation of the substrate for fermentation Pulp obtained from the ripe banana of cv. Robusta was mixed with 0.5% Pectinase CCM plus (a cocktail of enzymes obtained from Biocon Ltd., Bangalore), incubated for 90 min. at 50oC and the juice extracted by straining through a muslin cloth. The juice was then diluted with water in the ratio 2:1, TSS and acidity were adjusted to 22oBrix and 0.6%, respectively, followed by addition of 200ppm potassium metabisulphite and 0.03% diammonium phosphate. Fermentation Log phase culture of Saccharomyces cerevisiae UCD522 was inoculated @ 2% v/v to the above-mentioned substrate material, and fermentation was carried out at 18oC in 3 litre conical flasks fitted with loose cotton plugs. Progress in the fermentation process was measured using a Brix hydrometer, and, completely fermented juice was racked and clarified using Bentonite and stored at 10oC for two months. 218 Biochemical and sensory analysis of banana wine Banana wine was analyzed for pH, acidity, phenolics, residual sugar and alcohol (Amerine and Ough, 1982). Sensory properties of the wine were evaluated using a nine- point hedonic scale. Head-space volatile analysis of banana juice and wine using GC-FID and GC-MS Headspace aroma of banana juice and wine was extracted by solid phase micro-extraction (SPME) technique and analyzed using GC-FID and GC-MS/MS. Highly crossed-linked 50/30μm Divenylbenzene/Carboxen/ Polydimethylsiloxane (DVB/CAR/PDMS) SPME fibre (Supelco Inc. Bellefonte, PA, USA) was used for extraction of volatile compounds from banana juice and wine. Sodium chloride was added to the sample prior to head-space sampling to improve extraction efficiency, thus increasing the amount of analytes adsorbed onto the fibre (Pawliszyn, 1997). Extraction process followed for estimating head- space volatiles in banana fruit juice and wine was as described earlier by (Vermeir et al, 2009). Ten ml of the fruit juice diluted with an equal quantity of water, and, 20ml wine samples plus 1g NaCl were transferred to two 50 ml vials with screw-caps silicon rubber septum and a small magnetic bar. Vials were sealed with the rubber septum immediately after transfer of the sample, and were kept at 37±1oC for 15 min. with continuous stirring to facilitate transfer of analytes and equilibration to the head-space. Sampling was done by inserting the pre-conditioned fibre in the head-space for 90 min. at 37±1oC with continuous stirring. Subsequently, the SPME device was introduced into the injector port for gas chromatographic analysis, and was kept in the inlet for 10 min. for desorption. GC-FID analysis was performed on a Varian-3800 gas chromatograph (VarianBV, Harculesweg B,4338 Pl Middelburg, The Netherlands) system equipped with 30m X 0.25mm ID with 0.25μm film-thickness VF-5 fused silica capillary column (Varian Inc., 25200 Commercentre Drive, Lake Forest, CA 92630-8810, USA). The detector and injector were net at temperatures 270 and 250oC, respectively, and the column oven temperature program was: 50oC for 2 min. followed by increment of 3oC/min up to 200oC held for 3 min., and then, with increment rate of 10oC/min. up to 220oC and held for 8 min. at the same temperature. The carrier gas was helium, with a flow rate of 1.0ml/min. with 1:5 split ratio. For qualitative identification of volatile substances and for comparative variation of retention time and index, standards such as ethyl acetate, propanol, butanol, amyl alcohol, isoamyl acetate, pentanol, hexanol, 1-octene-3-ol, eugenol were co-chromatographed. Varian-3800 Gas Chromatograph coupled to a Varian- 4000, Ion-trap mass spectra detector (VarianBV, Harculesweg B,4338 Pl Middelburg, The Netherlands) equipped with a fused-silica capillary column VF-5MS with 30m x 0.25mm id, 0.25μm film-thickness from Varian (Varian Inc., 25200 Commercentre Drive, Lake Forest, CA 92630- 8810, USA) was used for GC-MS analysis of volatile constituents. Helium, with a flow rate of 1ml/min, was used as the carrier gas. The mass spectrometer was operated in the external electron ionization mode at 70eV, with full mass scan-range 45–450 amu. The ion trap, transfer line and ion source temperatures were maintained at 200oC, 240oC and 210oC, respectively. Temperature was programmed as described earlier. Head-space volatiles were quantified as relative per-cent area in GC-FID chromatogram, and were identified by comparing retention index as determined using homologous series of n-alkanes (C5 to C32) as the standard (Kovats, 1965) and comparing the spectra available with two spectral libraries, Wiley-2005 and NIST-2007. RESULTS AND DISCUSSION In the present experiment, an alcoholic beverage was prepared from ripe fruits of the popular banana cultivar, Robusta. The beverage possessed biochemical characteristics typical of dry table wines (Table 1). It possessed a pleasant aroma, distinct from unfermented juice, and was scored as “like very much” by a panel of trained judges (scoring 8±0.6 in the nine-point hedonic scale). Analysis of the head-space volatiles revealed a clear difference between aroma principles of the fresh juice and the wine. The principal groups of aroma compounds found in the head-space volatiles of juice and wine were esters, Table 1. Biochemical composition of alcoholic beverage prepared from banana cv. Robusta (AAA Group) Parameter Value p H 4.00 ± 0.15 Total acidity (% Citric acid) 0.50 ± 0.012 Alcohol (%v/v) 10.98 ± 0.56 Volatile acidity (% Acetic acid) 0.03 ± 0.00 Phenolics (mg/l) 606 ± 32 Residual sugars (mg/l) 700 ± 25 *Total antioxidant potential (mg AEAC/l) 326 ± 1.20 **Sensory score (in 9 point Hedonic scale) 8 ± 0.6 Values given are a mean of three replicates ± std deviation * AEAC= Ascorbic acid equivalent antioxidant capacity ** Mean of 10 replications J. Hortl. Sci. Vol. 8(2):217-223, 2013 Ranjitha et al 219 alcohols, phenols, carboxylic acids, carbonyl compounds, hydrocarbons, and a few others like phenyl-methoxy compounds (Fig. 1). Esters were the most prominent aromatic principles in juice (50%) and wine (62.9%). Levels of carbonyl compounds and hydrocarbons were high in fruit juice (13.1% and 11.86%, respectively), and the proportion of alcohols in head-space was similar in both the products. Carboxylic acid fraction was very negligible (1.4%) in banana juice, but its proportion increased significantly in wine (14.1%). The above observation points to disappearance or modification of a few aroma compounds, and simultaneous production of another set of flavor principles during wine- making. Research on production of flavor compounds in grape wine is rather advanced, and studies have shown that during alcoholic fermentation of the fruit, yeast produces ethanol, carbon dioxide and a number of by-products, including esters (Mateo et al, 1992). Aromatic profile pattern of a wine is a function of the fermentative strain, vinification temperature and glycosylated aroma precursors present in the fruit (Lilly et al, 2000). Occurrence of glycosylated compounds like fatty acids and shikimic acid derivatives have been reported earlier in banana fruit (Perez et al, 1997). Relative abundance of individual aroma compounds is presented in Table 1. A total of 19 alcoholic compounds were present in the banana juice, while the fermented beverage possessed only 15 compounds belonging to the same functional group. It was found that amyl alcohol, (E,E)- dodeca-8,10-dien-1-ol, 11-tridecyne-1-ol were the major hydroxyl compounds in banana juice, while, amyl alcohol, α-methylphenethyl alcohol, (Z,Z)- dodeca -3, 6-dien-1-ol, etc. were prominent in banana wine. Phenols such as methyl euginol, euginol, isoeuginol and methoxy euginol were present in both banana juice and wine, while, 2-methoxy-4 vinylphenol was detected only in the banana juice. These are low aroma-threshold compounds and have been earlier reported to contribute the floral note to banana aroma (Shiota, 1991). The compound, 2-phenyl ethyl alcohol, was identified as one of the major aglycon moieties in the ripe banana fruit (Perez et al, 1997). The glycosidases present in the banana juice would have helped release this bound flavour from its precursor molecule. Phenyl ethyl alcohol imparts a sweet, floral, rosy note to the product (Ribereau- Gayon et al, 2006). The flavour profile of banana juice was characterized by approximately 21 types of carbonyl compounds, of which (Z,Z)-oxacyclo trideca-4-7-dien-2-one, trans-2- hexenal, β-ionone, isoamyl aldehyde, etc. were present in higher quantities. But, wine possessed very low levels of carbonyl compounds, which were predominated by isoamyl aldehyde, methyl nonyl ketone and cycloisolongifolene. This observation leads to the inference that even though most carbonyl compounds are incapable of surviving vinification, some carbonyls like isoamyl aldehyde and methyl nonyl ketone are synthesized during banana wine making. The carbonyl fraction, along with the alcohols, contributes to the woody or musty flavor, among which, trans-2-hexenal and pentan-2-one contribute to the herbal note in banana juice (Shiota, 1991). Decrease in levels of hexanal and trans-2- hexenal are reported earlier in grape fermentation (Kotseridis and Baumes, 2000). The above observation suggests that radical differences in the levels of highly odorous carbonyl compounds also contribute to the distinctness of banana wine aroma. There were 11 kinds of acid in the head-space of banana juice, and this number were 12 in the banana wine. The banana juice had higher quantity of short-chain carboxylic acids, while, the wine was predominated by long- chain acids, of which n-decanoic acid was the most predominant. Fatty acids in wines result from auto-oxidation of saturated lipids in the fruit and the cell membrane component of yeast. The most abundant fatty acid in the banana wine, n-decanoic acid (capric acid), is an important component of yeast cell membrane, and autolysis of the yeast cell gives way to its release in the wine (Rapp, 1998; Torija et al, 2003). Esters were, by far, the predominant compounds in banana juice and wine. Banana juice contained 38 esteric compounds, of which, short-chain organic acid esters such as that of acetic, propanoic, butyric, isovaleric acid, etc., were the most abundant. Banana wine had 37 ester compounds in the head space, with large amounts of longer- chain acid esters like that of decanoic, dodecanoic, octanoic, octadecanoic acids etc. In the present study, the most Table 2. Head-space volatile compounds identified in juice and wine from banana cv. Robusta (AAA Group) J. Hortl. Sci. Vol. 8(2):217-223, 2013 Aroma analysis in banana fruit juice and wine 220 Table 2. Contd. Name of the compound Kovat’s Relative area percentage index Juice Wine Tridecan-2-one 1498 0.30 — Tridecanal 1522 0.09 — Tetradecanal 1584 — 0.13 2-Methylhexadecanal 1835 0.32 — (Z)-9,17-Octadecadienal 1988 0.33 — Acids 2-Hydroxy-2- 966 — 0.06 methylbutanoic acid 4-Hexenoic acid 984 0.35 — 2,3,3-Trimethyl-4- 1019 0.01 — pentenoic acid Heptanoic acid 1083 0.09 0.07 Benzoic acid 1178 — 0.61 4-Butoxybutanoic acid 1249 0.39 — 8-Nonenoic acid 1274 0.21 — 3-Ethyl-3-methylpentanedioic 1451 0.23 — acid Tridecanoic acid 1324 — 0.03 3-Ethyl-3-methylpentanedioic 1454 — 0.16 acid Undecanoic acid 1458 — 0.43 n-Decanoic acid 1573 — 11.88 Dodecanoic acid 1592 — 0.15 Pentadecanoic acid 1843 — 0.06 Hexadecanoic acid 1961 0.21 0.63 cis-9-Octadecenoic Acid 2095 — 0.04 Esters Methyl 2-propenoate 578 — 0.82 Ethyl 2-butynoate 794 0.02 — trans-2-Hexenyl formate 803 0.24 — Ethyl butanoate 806 0.15 — Butyl acetate 812 0.12 0.03 Ethyl isovalerate 858 — 0.01 Isoamyl acetate 872 6.60 2.92 Propyl butanoate 912 0.54 — Propyl isovalerate 956 0.48 — Propyl-2-methyl butanoate 978 0.15 — Ethyl 3-hexenoate 992 — 0.16 Butyl butanoate 994 2.35 — Ethyl hexanoate 996 — 0.41 Isoamyl butanoate 1008 2.11 — Hexyl acetate 1010 0.07 — Isopentyl 2-methyl propanoate 1013 1.17 — Butyl isovalerate 1072 10.02 — 6-Heptenyl acetate 1073 — 0.03 Ethyl sorbate 1089 — 0.20 Ethyl heptanoate 1099 — 0.06 Isopentyl isovalerate 1105 19.45 0.38 Ethyl benzoate 1172 — 2.43 Isoamyl iso valerate 1183 0.02 — Butyl hexanoate 1186 0.05 — Hexyl butanoate 1190 1.48 0.38 trans-2-Hexenyl Butyrate 1191 1.21 0.04 1-Methylhexyl butyrate 1198 0.01 0.04 1-Methylheptyl butyrate 1217 0.06 — Butyl sorbate 1222 0.29 — β-Phenylethyl acetate 1226 — 0.62 Table 2. Head-space volatile compounds identified in juice and wine from banana cv. Robusta (AAA Group) Name of the compound Kovat’s Relative area percentage index Juice Wine Alcohols Amyl alcohol 765 1.33 1.61 1-Hexyne-3-ol 779 0.06 — 2,3-Butanedithiol 898 0.02 0.02 4,4-Dimethyl-2-pentanol 801 0.32 — Butanediol 910 — 0.03 1-Methyl-2-cyclohexen-1-ol 918 0.14 — 1,2-Pentanediol 923 — 0.17 (3E)-2-Ethyl-3-hexen-1-ol 1010 0.05 — α-Methylphenethyl alcohol 1155 — 0.82 2-(4-Methylcyclohexyl)- 1159 0.33 0.18 2-propanol (E,Z)-3,6-Nonadien-1-ol 1175 0.20 0.45 2-(1,1-dimethylethyl)- 1191 0.19 — Cyclohexanol Citronellol 1234 0.09 — 1-Cyclohexyl-1-butanol 1245 0.04 — (Z,Z)-Dodeca-3,6-dien-1-ol 1418 0.39 — (E,E)-Dodeca-8,10-dien-1-ol 1482 1.07 7-Tridecanol 1492 0.09 0.33 1,10-Decanediol 1514 0.09 — Nerolidol 1564 — 0.10 11-Tridecyn-1-ol 1582 1.45 — (Z,Z)-6,9-Pentadecadien-1-ol 1783 0.03 0.21 Phytol 2122 — 0.06 Phenols 2-Methoxy-4-vinylphenol 1191 — 1.26 Methyleugenol 1338 0.55 0.10 Eugenol 1384 0.95 0.16 Isoeugenol 1428 0.08 1.72 Methoxyeugenol 1609 1.16 1.52 Aldehydes and Ketones Isoamylaldehyde 653 0.42 1.89 trans-2-Hexenal 859 3.63 — 2,4-Hexadienal 911 0.22 — 1-(1-Methyl-2- 962 0.44 — cyclopenten-1-yl) ethanone 2-Octanone 994 0.42 0.01 2,2-Dimethylocta-3,4-dienal 1109 0.04 — Pulegone 1175 0.31 — Citronellal hydrate 1248 0.10 0.02 5,6-Decanedione 1288 0.07 — Methyl nonyl ketone 1292 0.50 1.44 (2 Undecan2-one) (E,E)-2,4-Decanedienal 1294 0.03 — 2,4-Decadienal 1312 0.02 — 1-(2,6,6-Trimethyl-2- 1326 0.04 — cyclohexen-1-yl) acetone Dodecanal 1371 0.28 — 2-Butyl-2-octenal 1385 0.03 — (Z,Z)-Oxacyclotrideca- 1445 4.75 — 4,7-dien-2-one 8,9-dehydro-9-formyl- 1469 — 0.44 Cycloisolongifolene β-Ionone 1493 0.77 — J. Hortl. Sci. Vol. 8(2):217-223, 2013 Ranjitha et al 221 Table 2. Contd. Name of the compound Kovat’s Relative area percentage index Juice Wine Hexyl iso-valerate 1240 1.32 — Butyl (E)-2-hexenoate 1257 0.05 — n-Hexyl iso-valerate 1259 0.04 — Propyl octanoate 1277 — 0.05 Isomenthyl acetate 1298 0.16 — Isobutyl benzoate 1302 — 0.02 1-Octen-3-ol butyrate 1322 0.36 — Butyl octanoate 1387 — 0.39 1-Ethylpropyl octanoate 1417 — 0.28 Amyl octanoate 1478 — 1.36 Propyl decanoate 1493 — 20.51 Eugenyl acetate 1526 0.03 — Methyl dodecanoate 1528 — 0.06 Isobutyl decanoate 1545 — 0.20 Ethyl dodecanoate 1562 — 11.77 Phenylethyl valerate 1565 0.58 — E-2-Hexenyl benzoate 1583 — 0.11 Iso-amyl decanoate 1647 0.06 2.88 Ethyl trans-4-decenoate 1760 — 1.46 Ethyl tetradecanoate 1793 — 1.84 3-Methylbutyl dodecanoate 1858 0.10 — Methyl -9-hexadecenoate 1877 0.02 0.93 Methyl hexadecanoate 1889 — 0.48 (E)-4-Tridecenyl acetate 1892 0.24 — Methyl (E)-7-hexadecenoate 1898 0.06 4.69 Butyl hexadecanoate 1978 0.01 — Ethyl hexa decanoate 1991 0.22 5.12 Isopropyl hexadecanoate 2021 0.03 — Ethyl heptadecanoate 2098 — 0.12 Methyl octadecanoate 2128 — 0.22 Ethyl -cis,cis-9,12- 2185 0.37 octadecadienoate Ethyl cis-9-octadecenoate 2189 0.05 0.78 Ethyl octadecanoate 2209 0.02 0.38 Hydrocarbons Naphthalene 1175 0.33 — (4E,8Z)-1,4,8-Dodecatriene 1225 0.67 — (E,Z)-5,7-Dodecadiene 1239 0.36 — (E,Z)-5,7-Dodecadiene 1246 3.53 — 3-Dodecyne 1252 1.57 — Azulene 1311 — 0.51 Caryophyllene 1435 0.27 — (Z)-5-Pentadecen-7-yne 1552 0.61 — (E)-7-Pentadecen-5-yne 1556 0.19 — (Z)-4-Hexadecen-6-yne 1641 4.33 — 1,E-8,Z-10-Pentadecatriene 1518 — 0.17 Others — — 2-Ethylfuran 705 0.12 — 1-Nitro-2,2-dimethylpropane 794 0.12 — 2,3-Butanedithiol 901 0.35 — 2-Propyloctahydro-1- 1394 0.09 — benzothiophene 3,4,5-Trimethoxyallylbenzene 1560 6.64 5.58 (Z)-5-Propenyl-1,2,4- 1621 0.14 — trimethoxybenzene predominant ester in banana juice was found to be butyl isovalerate (10.6%). Butyl isovalerate (3-methyl butyl butanoate) was identified as the major constituent of head- space volatiles in all the banana cultivars from Madeira Island (Nogueira et al, 2003). Acetate esters alone contributed 10.6% of the total head-space volatiles in banana juice, while, their share in the wine dropped to 4.63%. Isoamyl acetate was the major acetic acid ester present in banana juice (6.6%). Butanoates alone contributed 10.38% to the total head-space volatiles in banana juice, while, their share in the wine aroma profile was reduced to 0.79%. Butyl and isopentyl alcohol esters of isovaleric acid constituted 29.47% of the total juice head-space volatiles. A rise in production of isopentyl isovaleric acid during the ripening of banana was observed by Macku and Jennings (1987). Banana owes its fruity aroma to acetates and butanoates of butanol, isoamyl alcohol, pentan-2-ol and hexyl acetate (Shiota, 1991). Abundance of decanoic acid and dodecanoic esters in the wine was 23.59% and 23.39%, respectively, while their share in the juice was almost negligible. In order of abundance, esters found in the juice were: isoamyl acetate> butyl acetate> butyl butanoate >hexyl isovalerate. The wine contained propyl decanoate, methyl-(E)-7-hexadecenoate, ethyl benzoate, isoamyl decanoate, amyl octanoate, etc., in high quantities. Decanoic acid and dodecanoic acids are components of the yeast cell membrane, and are abundant at low-temperature growth of the yeast (Torija et al, 2003). Ethyl dodecanoate is reported to have a typical wine-yeast background aroma and propyl decanoate has a waxy, sweet aroma with low odour-strength. These two compounds are reported in fermented and distilled beverages like wine, brandy and whisky (Comuzzo et al, 2006). The esters are synthesized by alcohol acetyl transferases, using higher alcohols and acetyl co-A as substrates. Esterases present in the yeast can significantly synthesize or hydrolyze the esters, based on physico-chemical conditions of the wine, a fact which supports discovery of new esters in wine, as compared to the juice (Lilly et al, 2006). A few hydrocarbons were also identified in the present study. (Z)-4-hexadecen-6-yne, (E,Z)-5,7-dodecadiene and 3-dodecyne were the important hydrocarbons present in banana juice, but were absent in the banana wine. Instead, new compounds such as azulene and 1, E-8, Z-10- pentadecatriene were present, though in very small levels, in banana wine. A variety of hydrocarbons have already been detected in banana volatiles (Shiota, 1991). Nevertheless, their contribution to banana juice aroma may J. Hortl. Sci. Vol. 8(2):217-223, 2013 Aroma analysis in banana fruit juice and wine 222 be negligible, as, the alkanes, alkenes, alkynes, naphthalenes, etc. have high aroma-thresholds. Among other flavouring compounds, 3,4,5-trimethoxy allyl benzene (elemicin), a natural phenyl propene, and a constituent of the essential oil in nutmeg, was also present in a high proportion in both banana juice and the wine. Euginol and elemicin give a pleasant, mellow aroma to the ripe banana fruit (Wang et al, 2007). Another significant volatile was 2-methoxy 4- vinyl phenol, present in the wine but not in the juice. This compound is a major odour compound in many white wines, and aroma of the pure compound is described as wine-like (Comuzzo et al, 2006). This suggests that origin of this compound in banana wine lies in the fermentation process. CONCLUSION There is a clear difference in head-space volatile profiles of banana juice and wine. Aroma signature compounds of banana juice, viz., isoamyl acetate, butyl isovalerate, isopentyl isovalerate, trans-2-hexenal, butanoates, etc. were present only in a low proportion in banana wine. 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