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. 2021 Jun 19;59(4):1529–1537. doi: 10.1007/s13197-021-05163-9

Characterization of odor-active volatile compounds of jambolan [Syzgium cumini (L.) Skeels] wine

Jorge A Pino 1,2,✉, Sixsy Espinosa 2, Cira Duarte 1,2
PMCID: PMC8882539  PMID: 35250076

Abstract

Volatile constituents in jambolan [Syzgium cumini (L.) Skeels] wine were isolated by headspace–solid phase microextraction (HS–SPME) and analyzed by gas chromatography-flame ionization detector (GC–FID), gas chromatography-mass spectrometry (GC–MS), and gas chromatography–olfactometry (GC–O). The composition of the jambolan wine included 52 esters, 20 terpenes, 13 alcohols, 12 acids, 11 aldehydes, 4 ketones, 4 oxides, and 5 miscellaneous compounds. Aroma extract dilution analysis and odor activity units were used for the determination of odor-active compounds. A total of 19 odor-active compounds were found as odor-active volatiles, from which (E)-β-ionone, phenylacetaldehyde, ethyl acetate, ethyl hexanoate, and ethyl benzoate were the most important. The similar results of the GC–O and OAV approaches suggests that HS–SPME–GC–O could be used as a fast and simple tool to quality control of the jambolan wine aroma.

Keywords: Syzgium cumini, Jambolan, Wine volatiles, HS–SPME, GC–O, Odor activity value

Introduction

Syzygium cumini (L.) Skeels (Syn. Eugenia jambolana Lam.), a large evergreen tree, is native to Indian sub-continent, but the plant has also been introduced to many tropical and subtropical regions (Dagadkhair et al. 2017). The fruit is known by its medicinal properties, e.g. stomachic, antidiabetic, diuretic, digestive, antiscorbutic, and antioxidant (Baliga et al. 2011; Ramya et al. 2012; Ayyanar and Subash-Babu 2012; Sehwa 2014). The fruit is commonly named as Java plum, Malabar plum, Portuguese plum, black plum, Indian blackberry, jaman, jambul, jambu, jambool, duhat and jambolana (Baliga et al. 2011). The ripen fruit is dark-purple or nearly black and it has a balance of sweet, slightly sour and astringent flavor, which justify its use into beverages, jam, jelly, wines and vinegar (Sehwag 2014). While, grapes are the crop most widely grown for winemaking, other underutilized tropical fruits could be used to produce wines. These wines have distinctive flavor and aroma typical of the original fruit and a good acceptance by the consumers. There are some reports about the production of wine from jambolan fruit in India (Chowdhury and Ray 2007; Joshi et al. 2012; Dahal and Das 2015; Holegar et al. 2017; VenuGopal and Anu-Appaiah 2017; VenuGopal et al. 2018), but in Cuba is only locally produced in some regions. Although volatile components of jambolan fruit have been studied (Vijayanand et al. 2001; Mehta et al. 2017), the volatile constituents of its wine have not been described up till now.

Wine flavor is composed of volatile compounds, which are especially responsible for its aroma. These characteristics are the results of complex interactions among diverse factors including fruit variety, quality of fruits which are fermented, yeast strain and fermentation conditions (Wattanakul et al. 2020). The influence of volatile compounds in wine aroma depends on their concentration and the specific olfactory perception threshold for each compound (Somkuwar et al. 2020).

The aims of this study were to determine the volatile profile by HS–SPME–GC–MS analysis and the odor-active compounds of jambolan wine.

Materials and methods

Materials

The following chemical standards were acquired from the following sources: ethyl acetate, ethyl propanoate, ethyl butanoate, 1,1-diethoxyethane, butan-1-ol, 3-methylbutan-1-ol, 2-methylbutan-1-ol, hexan-1-ol, (Z)-3-hexen-1-ol, 2-ethylhexan-1-ol, octan-1-ol, 1-octen-3-ol, nonan-1-ol, ethyl 2-methylpropanoate, ethyl 2-methylbutanoate, ethyl 3-methylbutanoate, 2-methylpropyl acetate, 3-methylbutyl acetate, ethyl 3-hydroxybutanoate, ethyl pentanoate, ethyl hexanoate, ethyl heptanoate, ethyl 2-furoate, ethyl 2-phenylacetate, hexanal, octanal, nonanal, benzaldehyde, phenylacetaldehyde, 2-furfural, salicylaldehyde, 2-phenylethanol, ethyl benzoate, ethyl octanoate, ethyl nonanoate, ethyl decanoate, ethyl dodecanoate, ethyl tetradecanoate, 2-phenylethyl acetate, (Z)-3-hexenyl acetate, 2-methylpropyl butanoate, hexyl 2-methylbutanoate, hexyl pentanoate, methyl salicylate, ethyl salicylate, diethyl succinate, butane-2,3-diol, γ-butyrolactone, 6-methyl-5-hepten-2-one, (E)-β-ionone, α-pinene, α-phellandrene, myrcene, limonene, 1,8-cineole, γ-terpinene, p-cymene, linalool, borneol, terpinen-4-ol, α-terpineol, 2-methylpropanoic acid, butanoic acid, hexanoic acid, octanoic acid, decanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, methyl nonanoate, n-hexane, n-heptane and a C8–C32 n-alkane series, used to determine Kovats’ retention indices (Sigma–Aldrich, St. Louis, MO), and absolute ethanol, sodium chloride and anhydrous citric acid (Merck, Darmstadt, Germany). Chemical standards 3-methylbutanal, 2-methylbutyl acetate, (Z)-3-hexenyl 3-methylbutanoate, ethyl 2-hydroxypropanoate, ethyl 2-hydroxy-3-methylbutanoate, and hexyl 3-methylbutanoate were a gift from Robertet (Grasse, France).

Winemaking

Ripe jambolans (25 kg) were crushed by hand, deseeded and crushed in a colloid mill. The juice was maintained at 26 °C for 4 h and filtered using a cotton bag filter. Then, it was added at 17% m/m to a must prepared with brown sugar (180 g/L), ammonium phosphate (2 g/L) and dibasic ammonium phosphate (1 g/L). The must was placed in a stainless-steel fermenter and it was inoculated with dried Saccharomyces cerevisiae yeast (1 g/L, Fermipan Lefersa, Havana). After fermentation for 10 days, the wine was racked with 1 g/L sodium bisulfite and stored at 15 °C for 14 days for subsequent evaluation of its quality. Fermentation was performed in triplicate.

Standard chemical analysis

Soluble solids (method 932.12), total acidity (method 942.15), and pH (method 981.12) were measured in the juice, while alcohol (method 969.12), total acidity (method 962.12), and pH (method 960.19) in wine by recommended methods (AOAC 2012). The chemical properties of juice and wine are shown in Table 1.

Table 1.

General composition of jambolan juice and wine

Value
Juice composition
Soluble solids (oBrix) 6.00 ± 0.06
Total acidity (% m/m anhydrous citric acid) 0.36 ± 0.01
pH 3.58 ± 0.01
Wine composition
Alcohol (% v/v) 12.71 ± 0.01
Total acidity (% m/m anhydrous citric acid) 0.36 ± 0.01
pH 3.12 ± 0.02
Residual extract (g/L) 19.5 ± 0.1
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Isolation of volatile compounds

Considering the results of previous works (Kafkas et al. 2006; Canuti et al. 2009; Pino and Queris 2010) the fiber selected was polydimethylsiloxane (PDMS), 100 µm film thickness, 1-cm needle size 24 gauge (Supelco, Bellefonte, PA). The HS-SPME procedure optimization was reported elsewhere (Pino and Queris 2010) and it fulfill the guidelines for SPME of volatile compounds for GC analysis, from the Working Group on Methods of Analysis of the International Organization of the Flavor Industry (IOFI Working Group on Methods of Analysis 2010). Extractions were carried out by placing 8 mL of wine and 1 g of sodium chloride into a 15 mL-vial sealed with a PTFE/silicone septum (Pino and Queris 2010). Internal standard methyl nonanoate (20 μL, 200 mg/L in ethanol) was added to the sample and mixed before analysis. The mixture was left to equilibrate 15 min at 30 °C. Headspace sampling extraction was made for 30 min under stirring mode at 500 min−1.

GC–FID and GC–MS analyses

GC–FID analysis was made on a Konik 4000A instrument (Konik, Barcelona) using a DB-Wax (30 m × 0.25 mm, 0.25 µm thickness; J & W Scientific, Folsom, CA) or DB-5 ms (30 m × 0.25 mm, 0.25 µm thickness; J & W Scientific, Folsom, CA) column. The GC parameters were as follows: oven temperature was 50 °C for 2 min and ramping up to 230 °C at 4 °C/min; hydrogen carrier gas flow 1 mL/min; injector and detector temperatures 230 °C; splitless injection (liner 0.75 mm I.D.) for 2 min. Relative peak areas of the compounds were electronically measured by the Konikrom Plus software (Konik, Barcelona). For some of them [ethyl acetate, 3-methylbutanal, ethyl propanoate, 2-methylbutan-1-ol, 3-methylbutan-1-ol, ethyl 2-methylpropanoate, ethyl 2-methylbutanoate, ethyl 3-methylbutanoate, 3-methylbutyl acetate, ethyl hexanoate, limonene, phenylacetaldehyde, 2-phenylethanol, ethyl benzoate, diethyl succinate, ethyl octanoate, hexyl 3-methylbutanoate, 2-phenylethyl acetate, ethyl decanoate, and (E)-β-ionone], chemical standard mixtures were prepared in a 13% (v/v) hydroalcoholic solution to cover the contents of each compound in the jambolan wine. Standard curves according to the internal standard method were generated for these compounds (Vial and Jardy 2004). All data were made by triplicate analyses.

GC–MS analysis was made on a HP-6890 gas chromatograph (Hewlett-Packard Co., Palo Alto, CA) coupled to a HP-5973 mass-selective detector, equipped with the same columns. Temperature programming of the oven were as previously described for the FID analysis. Injector and transfer line temperatures 250 °C; helium carrier gas flow 1 mL/min; and splitless injection (liner 0.75 mm I.D.) for 2 min. Mass spectra were acquired in scan mode (35–350 at 2 scans/s). Mass spectra were scanned in the m/z range 33–350 da. The MS detector was in scan mode (mass range 35–400) and the temperature source was 230 °C. Identifications were achieved by matching both the linear retention indices and mass spectra of chemical standards. For the compounds with no chemical standard available, tentative identification was made through comparing the mass spectra with those commercial spectral databases (Wiley 275, NIST 02, Palisade 600, Adams 2001 and in house-Flavorlib) and considering a minimum match factor of 90%. Also, linear retention indices were comparing against those found in Adams (2007) and NIST Standard Reference Database (https://webbook.nist.gov/chemistry). Linear retention indices were calculated using an n-alkane series.

Gas chromatography–olfactometry (GC–O) of aroma extract dilution analysis (AEDA)

GC–O analysis was performed on a HP-6890 gas chromatograph (Hewlett-Packard Co., Palo Alto, CA) converted for GC–O use. The end of the DB-5 ms column was coupled to a deactivated Y-shaped glass splitter with two deactivated fused silica capillaries (50 cm × 0.25 mm) which divides the effluent to the FID and the sniffing port (200 °C) by. The sniffing port was a cylindrically shaped aluminum device with a beveled top and a central drill hole attached to the capillary. Analyses were carried out using the analytical parameters described above for the GC–FID analysis.

An AEDA procedure previously reported for GC–O analysis of wine to evaluate the contribution of the odorants was used (Martí et al. 2003). The original wine was diluted stepwise in ratios of 1:4 by the addition of a synthetic wine (mimic matrix) before the SPME analysis. The synthetic wine was made by mixing 3.6 g/L citric acid and 13% v/v ethanol solution, and the pH adjusted to 3.1 by the addition of 0.1 N NaOH. To check the linear recovery of this procedure, a model mixture was prepared by adding some compounds (ethyl propanoate, 3-methylbutan-1-ol, ethyl 3-methylbutanoate, ethyl hexanoate, 2-ethylhexan-1-ol, 2-phenylethanol, and (E)-β-ionone), in a concentration level similar to the jambolan wine, to the synthetic wine solution. This model mixture, and the successively dilutions of it, were analyzed using the SPME procedure. In all cases, correlation coefficients higher than 0.95 were found. Flavor dilution factors (as the last dilution at which the assessor perceived the odor) and odor description were recorded from three assessors.

Odor activity units’ determination

The odor detection thresholds in the mimic matrix described before were determined as previously reported (Pino and Queris 2010). Odor activity value (OAV) was calculated according to the concentration/threshold ratio of the odorant in the mimic matrix.

Sensory analysis

Sensory descriptive aroma analysis was applied for evaluation of the wine, by means of a 10-cm unstructured scale (0 = none, 9 = extremely strong). The sensory evaluations were made by five trained judges aged between 25 and 40 years. In the first session, the panel generated the descriptors of the jambolan wine; in the second and third, different chemical standards were given and debated by judges, eliminating the inappropriate terms. Seven aroma terms (winey, red berries, honey, rose, sweet, floral and tropical fruit) were selected to describe the wine. In the fourth session, the wine was evaluated in duplicate using the 10-point interval scale previously mentioned. Orthonasal evaluations were performed in coded glass vessels (7 cm × 3.5 cm) containing 20 mL of wine.

Results and discussion

In total, 121 volatile constituents were found in the jambolan wine, in which 52 esters represents the larger group (Table 2). Also, 20 terpenes, 13 alcohols, 12 acids, 11 aldehydes, 4 ketones, 4 oxides, and 5 miscellaneous compounds were found in the jambolan wine. Previous studies in jambolan fruit reported profiles rich in monoterpenes and sesquiterpenes (Vijayanand et al. 2001; Mehta et al. 2017). These differences between the amounts of such compounds may be accounted by the proper fermentation process, varietal specificity or the isolation procedure used.

Table 2.

Volatiles identified in jambolan wine

Compound RIa1 RIa2 RIp1 RIp3 Area %
Ethyl acetate 610 612 884 885 1.9
3-Methylbutanal 655 654 655 652 0.1
1,1-Diethoxymethane 657 657 – – t
Butan-1-ol 667 669 1146 1150 t
Pentane-2,3-dione 700 700 1060 1062 t
Ethyl propanoate 714 717 966 966 0.1
1,1-Diethoxyethane 726 726 889 889 0.3
3-Methylbutan-1-ol 739 741 1211 1210 28.8
2-Methylbutan-1-ol 742 742 1209 1208 12.4
Ethyl 2-methylpropanoate 751 751 960 961 0.6
2-Methylpropanoic acid 785 786 1580 1581 t
2-Methylpropyl acetate 788 780 1022 1022 0.1
Butane-2,3-diol 790 789 1539 1542 0.2
Hexanal 802 802 1083 1080 t
Butanoic acid 804 811 1623 1624 0.1
Ethyl butanoate 808 805 1040 1035 0.2
Ethyl 3-oxopropanoate 811 809 1242 – t
Ethyl 2-hydroxypropanoate 815 815 1358 1353 0.4
2-Furfural 834 836 1465 1464 t
Heptane-2,3-dione 843 844 – – t
3-Methylpentan-1-ol 853 853 1334 1334 t
4-Methylpentan-1-ol 855 856 1302 1302 0.1
Ethyl 2-methylbutanoate 857 858 1050 1048 0.2
Ethyl 3-methylbutanoate 859 859 1056 1055 0.2
(Z)-3-Hexen-1-ol 862 859 1391 1389 t
1,1-Diethoxy-2-methylpropane 866 861 969 969 t
Hexan-1-ol 867 871 1360 1359 t
2-Methylbutanoic acid 873 880 1666 1667 t
3-Methylbutyl acetate 881 881 1134 1134 1.6
2-Methylbutyl acetate 885 884 1126 1126 0.3
Ethyl pentanoate 901 901 1131 1131 t
γ-Butyrolactone 920 918 1617 1617 0.1
Ethyl 3-hydroxybutanoate 935 935 1524 1522 t
α-Pinene 937 939 1032 1035 t
2-Methylpropyl butanoate 943 943 1146 1146 t
Ethyl 3-oxobutanoate 946 944 1242 – t
1,1-Diethoxy-3-methylbutane 955 955 1073 1074 t
Benzaldehyde 961 960 1512 1512 0.1
Ethyl 2-hydroxy-3-methylbutanoate 975 975 1427 1430 0.1
1-Octen-3-ol 980 982 1458 1458 0.1
6-Methyl-5-hepten-2-one 985 986 1336 1339 t
Myrcene 990 991 1165 1165 t
Hexanoic acid 993 995 1850 1849 t
Ethyl hexanoate 995 998 1240 1240 3.9
Octanal 999 999 1280 1275 t
α-Phellandrene 1002 1003 1150 1150 t
Ethyl (E)-3-hexenoate 1004 1004 1292 1294 t
(Z)-3-Hexenyl acetate 1007 1005 1323 1323 t
2-Methylbutyl 2-methylpropanoate 1012 1017 1194 1194 t
1,4-Cineole 1015 1015 1169 1169 t
3-Methylbutyl 2-methylpropanoate 1017 1017 1183 1183 t
p-Cymene 1024 1025 1252 1253 0.3
Limonene 1027 1029 1200 1200 2.8
2-Ethylhexan-1-ol 1029 1032 1480 1481 t
1,8-Cineole 1032 1031 1213 1212 t
Phenylacetaldehyde 1041 1042 1625 1623 0.6
Salicylaldehyde 1045 1045 1663 1663 t
Ethyl 2-furoate 1048 1047 1627 1627 t
Ethyl 2-hydroxy-3-methylbutanoate 1058 1058 1425 1426 0.6
γ-Terpinene 1060 1060 1240 1242 t
Octan-1-ol 1069 1068 1553 1546 0.1
Allyl hexanoate 1080 1083 1370 1371 t
Terpinolene 1087 1089 1284 1280 t
Nonan-2-one 1090 1090 1401 1405 t
Linalool 1095 1097 1537 1535 t
Ethyl heptanoate 1098 1098 1337 1336 t
Nonanal 1100 1101 1385 1385 0.1
3-Methylbutyl 3-methylbutanoate 1104 1104 1296 1296 t
2-Phenylethanol 1106 1107 1873 1873 11.9
trans-Pinocarveol 1140 1139 1648 1648 t
Hexyl 2-methylpropanoate 1151 1152 1342 1339 t
2-Methylpropyl hexanoate 1153 1154 1346 1347 t
Pinocarvone 1163 1165 1575 1565 t
Borneol 1168 1169 1700 1700 t
Nonan-1-ol 1170 1169 1668 1668 t
Ethyl benzoate 1173 1173 1644 1644 11.9
Terpinen-4-ol 1175 1177 1600 1601 0.2
Diethyl succinate 1179 1179 1687 1681 2.8
Octanoic acid 1185 1183 2050 2050 0.2
α-Terpineol 1188 1189 1695 1697 0.3
Methyl salicylate 1192 1192 1765 1765 t
Ethyl octanoate 1198 1197 1440 1440 10.3
(Z)-3-Hexenyl 2-methylbutanoate 1230 1232 1472 1472 t
Hexyl 2-methylbutanoate 1237 1236 1433 1431 0.1
Hexyl 3-methylbutanoate 1241 1240 1425 1425 0.6
Carvacrol methyl ether 1243 1245 1614 1604 t
(Z)-3-Hexenyl 3-methylbutanoate 1245 1247 – – 0.3
Hexyl pentanoate 1247 1247 1485 1487 0.5
(E)-2-Hexenyl 3-methylbutanoate 1249 1248 – – 0.1
Ethyl 2-phenylacetate 1251 1248 1782 1785 0.1
3-Methylbutyl hexanoate 1254 1254 1453 1450 t
2-Phenylethyl acetate 1258 1258 1826 1826 0.3
Hexyl 3-hydroxyhexanoate 1264 1262 2066 2066 t
(E)-Cinnamaldehyde 1268 1270 2033 2033 t
Ethyl salicylate 1270 1270 1786 1788 t
Vitispirane 1273 1277 1527 1515 t
Undecanal 1307 1307 1609 1609 t
Ethyl nonanoate 1320 1320 1521 1520 t
Heptyl 3-methylbutanoate 1340 1342 – – 0.1
2-Methylpropyl octanoate 1345 1345 1561 1551 t
Hexyl hexanoate 1382 1384 1599 1598 t
Decanoic acid 1386 1386 2279 2279 0.2
3,3-Dimethylcyclohexanol 1390 1392 – – 0.2
Ethyl decanoate 1396 1396 1643 1643 1.9
Dodecanal 1411 1409 1729 1720 t
3-Methylbutyl octanoate 1450 1451 1670 1670 t
Geranyl acetone 1455 1455 1853 1856 t
(E)-β-ionone 1489 1489 1955 1955 0.1
Dodecanoic acid 1565 1568 2515 2517 0.1
Caryophyllene alcohol 1572 1572 – – t
Hexyl benzoate 1580 1580 2056 2056 t
Ethyl dodecanoate 1593 1595 1838 1837 0.1
γ-Eudesmol 1632 1632 2180 2187 0.1
epi-α-Cadinol 1637 1640 – – t
α-Muurolol 1648 1646 2182 – t
α-Eudesmol 1651 1654 2235 2237 t
Tridecanoic acid 1660 1661 2603 2603 t
Tetradecanoic acid 1775 1779 2696 2695 0.2
Ethyl tetradecanoate 1798 1796 2044 2040 t
Pentadecanoic acid 1868 1868 2819 2819 0.1
Hexadecanoic acid 1960 1960 2914 2913 0.3
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RIao and RIpo: Retention indices from standard or literature on DB-5ms and DB-Wax

RIs from literature were taken from Adams (2007) and https://webbook.nist.gov/chemistry

t: <0.1%

1RIa and RIp: Experimental retention index on capillary columns DB-5ms and DB-Wax

Esters are desirable compounds because most of them contribute to the typical fruity and floral flavor properties of wines (Perestrelo et al. 2006). Among them, ethyl benzoate, ethyl octanoate, ethyl hexanoate, ethyl acetate, ethyl decanoate, and 3-methylbutyl acetate were the main compounds in the jambolan wine. These esters were formed in the fruit or in the fermentation process (Martinez et al. 1998).

The volatile compounds isolated by HS–SPME were examined by AEDA and OAV to find the most potent odorants (Table 3). The AEDA produced 20 odor regions with flavor dilution (FD) ranged from 32 to 512. Odors were mainly characterized as fruity, sweet, floral and winey, but any odorant resembled the jambolan wine aroma. Sniffing of the dilutions revealed the highest FD values for ethyl acetate (ethereal, fruity), phenylacetaldehyde (rosy, floral), and (E)-β-ionone (berry). However, other constituents with relatively high FD values were ethyl hexanoate (sweet, fruity, winey), ethyl benzoate (sweet, fruity), 3-methylbutan-1-ol (fermented, fruity), 2-phenylethanol (floral, sweet), and 2-phenylethyl acetate (honey).

Table 3.

Most odor-active volatile compounds identified in jambolan wine

Compound Content (mg/L) Odor quality1 Odor threshold (µg/L) FD factor OAV2
Ethanol 127,100 Alcohol 24,9003 – 5
Ethyl acetate 0.225 Ethereal, winey 5 512 45
3-Methylbutanal 0.012 Apple-like 5 32 2
Ethyl propanoate 0.009 Rum-like, fruity 10 32  < 1
3-Methylbutan-1-ol 3.371 Fermented, winey 280 128 12
2-Methylbutan-1-ol 1.445 Fermented, winey 300 64 5
Ethyl 2-methylpropanoate 0.073 Fruity, floral 15 64 5
Ethyl 2-methylbutanoate 0.024 Fruity, green 20 32 1
Ethyl 3-methylbutanoate 0.026 Fruity, berry-like 3 64 8
3-Methylbutyl acetate 0.191 Fruity, banana 30 64 6
Ethyl hexanoate 0.459 Sweet, winey 14 256 33
Limonene 0.032 Lemon-like 10 32 3
Phenylacetaldehyde 0.070 Rosy, floral 1 512 70
2-Phenylethanol 1.395 Floral 140 128 10
Ethyl benzoate 1.395 Sweet, fruity 60 256 23
Diethyl succinate 0.330 Winey 1250 64  < 1
Ethyl octanoate 1.199 Sweet 580 32 2
Hexyl 3-methylbutanoate 0.075 Green, fruity 22 64 3
2-Phenylethyl acetate 0.341 Honey 250 128 1
Ethyl decanoate 0.218 Sweet, pungent 200 32 1
(E)-β-ionone 0.012 Berry 0.09 512 133
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1Odor quality perceived at the sniffing port

2Odor-activity values were calculated by dividing the concentrations by the respective odor threshold

3The odor activity value for ethanol was calculated by dividing its concentration by its odor threshold in water

OAVs are a good means to evaluate the contributions of a compound to the aromas of the respective matrix (Schieberle 1995). Besides this, it is necessary that the odor threshold of the compound should be determined in a media like the food. Consequently, the odor thresholds for the components with higher FD were determined in a mimic matrix, representing the jambolan wine (Table 3). The odorant with the greatest FD value was (E)-β-ionone, with a peculiar berry note (Burdock 2010). This carotenoid degradation product is a significant contributor to the odor of raspberries (Klesk et al. 2004). Nevertheless, the results suggested that other 18 compounds should additionally contribute to the typical aroma of the jambolan wine considering that their concentrations were higher than their odor thresholds in the synthetic wine. Relatively high OAVs were also found for phenylacetaldehyde, ethyl acetate, ethyl hexanoate, ethyl benzoate, and 2-phenylethanol with OAVs ranged 10–70. Other constituents with OAVs between 1 and 8, ethanol, 3-methylbutanal, 2-methylbutan-1-ol, ethyl 2-methylpropanoate, ethyl 2-methylbutanoate, ethyl 3-metylbutanoate, 3-methylbutyl acetate, limonene, ethyl octanoate, hexyl 2-methylbutanoate, 2-phenylethyl acetate, and ethyl decanoate should also contribute to the aroma of the jambolan wine.

Two esters, ethyl propanoate and diethyl succinate, found as potentially significant by AEDA had OAVs < 1 and consequently, their contribution should not be important to the jambolan wine aroma. The possibly key compound determined with the odor activity approach is an improvement of that given by the AEDA and adjusts some of the limits of the GC–O procedure.

Concerning similarities between GC–O and OAV approaches, GC–O has been effective, since with a very slight effort it was possible to recognize the most significant odorants, according to the OAV method. Only ethanol ranked high by the OAV, but it had a low GC–O score.

Figure 1 shows the mean intensity ratings for the jambolan wine plotted on a spiderweb diagram. Winey, red berries, honey, and rose notes could be found as the great contribution on jambolan wine aroma. The winey note might be caused by ethyl acetate, ethyl hexanoate, 3-methylbutan-1-ol, and 2-methylbutan-1-ol. The red berries note might be associated with the berry-like smelling (E)-β-ionone, while the honey note might be related to 2-phenylethyl acetate. Phenylacetaldehyde might contribute to the rose note of the jambolan wine. Other series with lesser impact were sweet, floral, and tropical fruits. The sweet aroma descriptor might be linked with the odor of ethyl hexanoate, ethyl octanoate, ethyl decanoate, and ethyl benzoate, while the floral note might be given by phenylacetaldehyde, 2-phenylethanol, and ethyl 2-methylpropanoate. The tropical note might be attributed to ethyl 3-methylbutanoate, 3-methylbutyl acetate and hexyl 3-methylbutanoate (Burdick 2010).

Fig. 1.

Fig. 1

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Aroma sensory profiles of jambolan wine

However, sensory studies, including also model and omission tests, are necessary to confirm the contribution of these compounds to the jambolan wine aroma.

Conclusion

This study described potent odorants important to the overall aroma of the jambolan wine. Combination of AEDA and OAV studies showed that odor profile of the jambolan wine was mainly caused by nineteen odorants, from which (E)-β-ionone, phenylacetaldehyde, ethyl acetate, ethyl hexanoate and ethyl benzoate were the most odor-active compounds. They are potential indicators for the objective quality of the jambolan wine. The similar results of the GC–O and OAV approaches suggests that HS–SPME–GC–O could be used as a fast and simple tool to quality control of the jambolan wine aroma.

Authors contribution

JAP was responsible for conceiving the idea, carried out the work and wrote the MS; SE and CD carried out the work and corrected the manuscript.

Funding

The work and it was supported by the proper institute.

Data availability

The datasets used and/or analyzed during the current study are available from the corresponding author on reasonable request.

Declarations

Conflict of interest

On behalf of all authors, the corresponding author states that there is no conflict of interest.

Informed consent

All authors have read and approved the manuscript, and all are aware of its submission to JFST.

Footnotes

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

References

  1. Adams RP. Identification of Essential Oil Components by Gas Chromatography/Quadrupole Mass Spectroscopy. Carol Stream, IL: Allured Publishing Co.; 2007. [Google Scholar]
  2. AOAC (2012) Official Methods of Analysis, 19th ed., Association of Official Analytical Chemist. AOAC International, Washington DC
  3. Ayyanar M, Subash-Babu P (2012) Syzygium cumini (L.) Skeels: A review of its phytochemical constituents and traditional uses. Asian Pacific J Trop Biomed 240−246 [DOI] [PMC free article] [PubMed]
  4. Baliga MS, Bhat HP, Baliga BRV, Wilson R, Palatty PL. Phytochemistry, traditional uses and pharmacology of Eugenia jambolana Lam. (black plum): a review. Food Res Int. 2011;44:1776–1789. doi: 10.1016/j.foodres.2011.02.007. [DOI] [Google Scholar]
  5. Burdock GA. Fenaroli’s handbook of flavor ingredients. 6. Boca Raton: CRC Press Taylor & Francis Group; 2010. [Google Scholar]
  6. Canuti V, Conversano M, Calzi ML, Heymann H, Matthews MA, Ebeler SE. Headspace solid-phase microextraction–gas chromatography–mass spectrometry for profiling free volatile compounds in Cabernet Sauvignon grapes and wines. J Chromatogr A. 2009;1216:3012–3022. doi: 10.1016/j.chroma.2009.01.104. [DOI] [PubMed] [Google Scholar]
  7. Chowdhury P, Ray RC. Fermentation of jamun (Syzgium cumini L.) fruits to form red wine. ASEAN Food J. 2007;14(1):15–23. [Google Scholar]
  8. Dagadkhair AC, Pakhare KN, Todmal AD, Andhale RR. Jamun (Syzygium cumini) Skeels: a traditional therapeutic tree and its processed food products. Int J Pure App Biosci. 2017;5(5):1202–1209. doi: 10.18782/2320-7051.4011. [DOI] [Google Scholar]
  9. Dahal D, Das SKL. Preparation and quality evaluation of jamun (Syzygium cuminii L) wine. Sunsari Tech Coll J. 2015;2(1):17–22. doi: 10.3126/stcj.v2i1.14792. [DOI] [Google Scholar]
  10. Holegar HR, Suresh GJ, Vandana AK, Jagadeesh SL. Influence of cold soaking and thermovinification on quality of jamun (Syzigium cuminii) wine. Res Environ Life Sci. 2017;10(5):393–396. [Google Scholar]
  11. IOFI Working Group on Methods of Analysis Guidelines for solid-phase micro-extraction (SPME) of volatile flavour compounds for gas-chromatographic analysis, from the working group on methods of analysis of the international organization of the flavor industry (IOFI) Flavour Fragr J. 2010;25:404–406. doi: 10.1002/ffj.1991. [DOI] [Google Scholar]
  12. Joshi VK, Sharma R, Girdher A, Abrol GS. Effect of dilution and maturation on physico-chemical and sensory quality of jamun (black plum) wine. Ind J Nat Prod Res. 2012;3(2):222–227. [Google Scholar]
  13. Kafkas E, Cabaroglu T, Selli S, Bozdoğan A, Kürkçüoğlu M, Paydaş S, Başer KHC. Identification of volatile aroma compounds of strawberry wine using solid-phase microextraction techniques coupled with gas chromatography–mass spectrometry. Flav Fragr J. 2006;21:68–71. doi: 10.1002/ffj.1503. [DOI] [Google Scholar]
  14. Klesk K, Qian M, Martin RR. Aroma extract dilution analysis of cv. Meeker (Rubus idaeus L.) red raspberries from Oregon and Washington. J Agric Food Chem. 2004;52:5155–5561. doi: 10.1021/jf0498721. [DOI] [PubMed] [Google Scholar]
  15. Martí MP, Mestres M, Sala C, Busto O, Guasch J. Solid-phase microextraction and gas chromatography olfactometry analysis of successively diluted samples. a new approach of the aroma extract dilution analysis applied to the characterization of wine aroma. J Agric Food Chem. 2003;51:7861–7865. doi: 10.1021/jf0345604. [DOI] [PubMed] [Google Scholar]
  16. Martinez P, Valcarcel MJ, Perez L, Benitez T. Metabolism of Saccharomyces cerevisiae flor yeasts during fermentation and biological aging of Fino Sherry: by-products and aroma compounds. Am J Enol Viticult. 1998;49:240–250. [Google Scholar]
  17. Mehta PK, Galvão MS, Soares AC, Nogueira JP, Narain N. Volatile constituents of jambolan (Syzygium cumini L) fruits at three maturation stages and optimization of HS-SPME GC-MS method using a central composite design. Food Anal Meth. 2017 doi: 10.1007/s12161-017-1038-4. [DOI] [Google Scholar]
  18. Perestrelo R, Fernandes A, Albuquerque F, Marques J, Camara J. Analytical characterization of the aroma of Tinta Negra Mole red wine: identification of the main odorants compounds. Anal Chim Acta. 2006;563(1–2):154–164. doi: 10.1016/j.aca.2005.10.023. [DOI] [Google Scholar]
  19. Pino JA, Queris O. Analysis of volatile compounds of pineapple wine using solid-phase microextraction techniques. Food Chem. 2010;122:1241–1246. doi: 10.1016/j.foodchem.2010.03.033. [DOI] [Google Scholar]
  20. Ramya S, Neethirajan K, Jayakumararaj R. Profile of bioactive compounds in Syzygium cumini – a review. J Pharm Res. 2012;5(8):4548–4553. [Google Scholar]
  21. Schieberle P. In: characterization of food: emerging methods. Amsterdam, The Netherlands: Elsevier; 1995. pp. 403–431. [Google Scholar]
  22. Sehwag S (2014) Nutritive, therapeutic and processing aspects of Jamun, Syzigium cuminii (L.) Skeels – An overview. M. Das, Indian J Nat Prod Resources 5(4):295−307
  23. Somkuwar RG, Sharma AK, Kambale N, Banerjee K, Bhange MA, Oulkar DP. Volatome finger printing of red wines made from grapes grown under tropical conditions of India using thermal-desorption gas chromatography–mass spectrometry (TD–GC/MS) J Food Sci Technol. 2020;57:1119–1130. doi: 10.1007/s13197-019-04147-0. [DOI] [PMC free article] [PubMed] [Google Scholar]
  24. VenuGopal KS, Anu-Appaiah KA. Seed incorporation during vinification and its impact on chemical and organoleptic properties in Syzygium cumini wine. Food Chem. 2017;237:693–700. doi: 10.1016/j.foodchem.2017.05.160. [DOI] [PubMed] [Google Scholar]
  25. VenuGopal KS, Cherita C, Anu-Appaiah KA. Augmentation of chemical and organoleptic properties in Syzygium cumini wine by incorporation of grape seeds during vinification. Food Chem. 2018;242:98–105. doi: 10.1016/j.foodchem.2017.09.029. [DOI] [PubMed] [Google Scholar]
  26. Vial J, Jardy A. In: Encyclopedia of Chromatography. Cazes J, editor. New York: Marcel Dekker Inc.; 2004. pp. 1–2. [Google Scholar]
  27. Vijayanand P, Rao LJM, Narasimham P. Volatile flavour components of jamun fruit (Syzygium cumini L) Flav Fragr J. 2001;16:47–49. doi: 10.1002/1099-1026(200101/02)16:1<47::AID-FFJ944>3.0.CO;2-L. [DOI] [Google Scholar]
  28. Wattanakul N, Morakul S, Lorjaroenphon Y, Jom KN. Integrative metabolomics-flavoromics to monitor dynamic changes of ‘Nam Dok Mai’ mango (Mangifera indica Linn) wine during fermentation and storage. Food Biosci. 2020 doi: 10.1016/j.fbio.2020.100549. [DOI] [Google Scholar]

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Data Availability Statement

The datasets used and/or analyzed during the current study are available from the corresponding author on reasonable request.

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