Changes in volatile compounds of Ayvalik (Edremit) and Uslu olive oils depending on conditions and time of storage
46 different volatile compounds were identified. The inappropriate storage conditions of olives had a negative impact on the aroma profiles of oils. The most abundant compounds were hexanal, a-farnesene, dimethylpalmitamine, and a-Farnesene, 2-hexanal.
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Changes in volatile compounds of Ayvalik (Edremit) and Uslu olive oils depending on conditions and time of storage
Pelin Gьng Ergцnьl1, Alev Yьksel Aydar1,
Tuba Gцldeli1, Annalisa Mentana2 , Maurizio Quinto2
1 - Manisa Celal Bayar University, Manisa, Turkey
2 - Foggia University, Foggia, Italy
Abstract
Introduction. Volatile aromatic compounds present in olive oils extracted from Turkish olive cultivars including Edremit (Ayvalik) and Uslu were determined qualitatively.
Materials and methods. The olives were harvested from Akhisar/Manisa region, which is one of most important Turkish olive-growing locations, at almost the same maturity stage by hand. Harvested olives were put in case and nylon sacks and were stored under the same conditions until they analyzed. Determination of the volatile aroma compounds were done with the aim of Headspace Solid-Phase Microextraction (HS-SPME) and Gas Chromatography-Mass Spectrometry (GC-MS).
Results and discussion. 46 different volatile compounds were identified. The inappropriate storage conditions of olives had a negative impact on the aroma profiles of oils. The most abundant compounds were hexanal, a-farnesene, dimethylpalmitamine, and a-Farnesene, 2-hexanal, hexanal in olive oils extracted from Edremit (Ayvalik) and Uslu varieties, respectively. 1 -Hexanol was mostly increased compound in Edremit olive oils extracted from olives stored at nylon sacks during 14 days. The increase of concentration of 2-hexanal during holding periods could be explained by the activity of the fungal enzymes in Lipoxygenase pathway of olive fruits. While 5-Hepten-2-one 6-methyl and 1- Butanol 3-methyl were not detected in Edremit and Uslu olive oils at initial day, they formed during both sack and box holding due to the microbial activity in olives. Three principal components (PCs) were extracted representing 81.27% of the total variance of olive oil samples extracted from Uslu cultivar and 80.14 % of the total variance of olive oil samples extracted from Edremit cultivar. The first PCs, PC1, PC2 and PC3 represented 45.15 and 41.31%, 21.90 and 21.39%, 14.21 and 17.43%, for Uslu and Edremit varieties, respectively.
Conclusions. It is recommended to store olives at 5 °C in air conditioning boxes for at least 30 days to reduce fungal development and to maintain the desired aroma.
Keywords: GC-MS Holding Olive Oil PCA Volatile Compounds
Introduction
Olive fruit (Olea europaea) is one of most important products in Mediterranean countries and olive cultivation and processing has been carried out since the beginning of human civilization (Ozdemir et al. 2018). Olive and olive oil have superior nutritional properties due to high content of volatile and phenolic compounds, so their regular consumprion could help in prevention of such diseases such as cardiovascular diseases, cancer and osteoporosis. Production of a high quality virgin olive oil requires the storing the olive fruit in proper holding conditions (Inarejos-Garda et al. 2009). In addition to the extraction process and storage, cultivar and cultivar applications, geographical origin, climatic conditions, degree of fruit ripening also affect the content and composition of volatiles compounds in olive oils (Issaoui et al. 2010; Kesen et al. 2013). Several researchers have determined that the olive storage types and times affect the virgin olive oil quality as much as technological operations (Bouaziz et al. 2008; Inarejos-Garda et al. 2009; Pereira et al. 2002; Rizzo et al. 2011).
The presence of volatile and phenolic compounds directly influence and determine the quality of virgin olive oil. Volatile aromatic compounds are one of the most important factors for olive oil's quality and affect sensorial perception (Bayrak & Hu 2013). They are formed by the oxidation of oils with certain enzymes such as lipoxygenase (LOX pathway) (Cavalli et al. 2004). Olive oils possess more than 180 different aromas, and the majority of the volatile substances are presented by esters, aldehydes, hydrocarbons, ketones, and furans (Kesen et al. 2013). Servili et al (2003) studied the time of revealing of olive pastes to air during malaxation and found a positive correlation between air contact and the content of volatile compounds in olive oil including hexanal, 1-butanol, (Z)-3-hexen-1-ol, 1-penten-3- ol, and 2-methyl-1-butanol. Inappropriate olive fruit storage generally induce the activity of microorganisms that are responsible for unpleasant odours and formation of volatile compounds (Koprivnjak & Conte 2002).
Principal component analysis (PCA) is an statistical method that can be used to detemine the content of triglycerides, sterols, phenolic compounds and volatile compounds to distinguish oils from different cultivars (Boskou 2007; de Fernandez et al. 2014; Yang et al. 2017). The aim of this study was to examine the effects of different holding times and types on volatile aroma compounds of oil samples obtained from different olive cultivars named “Edremit and Uslu” collected from Aegean province, Akhisar Region of Turkey by Gas Chromatography- Mass Spectroscopy (GC-MS) headspace technique. There is no detailed information that compares the volatile profiles of oils extracted from olives holded in unsuitable conditions that is already applied by some olive producers. For this reason, this study carried out is of importance.
Materials and methods
Materials
Olive fruits (Olea europaea L.) from the Edremit and Uslu varieties grown in the Akhisar area were harvested in the 2012/2013 crop season. Maturity index of olives, which was calculated according to the method of the International Olive Oil Council (IOOC, 2011), was 3.75±0.35 and 4.50±0.71 for Edremit and Uslu cultivars, respectively. According to this method, 100 fruits were randomly taken to assess their level of maturity by a subjective evaluation of the color of the olive skin and flesh. The olives were distributed into eight groups according to the following characteristics: bright-green skin (group N 0), greenish- yellowish skin (group N 1), green skin with reddish spots (group N 2), reddish-brown skin (group N 3), black skin with white flesh (group N 4), black skin with < 50% purple flesh (group N 5), black skin with > 50% and < 100% purple flesh (group N 6), and black skin with 100% purple flesh (group N 7). Maturation indexes ranged from zero (intense green skin) to seven (black skin and 100% purple flesh). The maturity index was calculated by X (Nini)/100, where N is the group number and n is the olive amount in that group (Aydar et al. 2017). Air temperature and weather conditions during olives holded periods were shown in Table 1 (Turkish State Meteorological Service, 2012-2013). Olives were put into nylon sacks (60x90 cm) and plastic boxes (53x37x31 cm) and were hold inside them for 0, 7, 14 and 21 days. Olive oil samples symbolized as E: Edremit variety, U: Uslu variety, K: Holded in plastic boxes, and C: Holded in nylon sacks.
volatile compounds ayvalik
Table 1 Air temperature and weather conditions during olives holded periods (Turkish State Meteorological Service, 2012-2013)
|
MANISA/AKHISAR |
Air temperature (°C) |
Weather |
|
|
21.12.2012 (harvest-first extraction) |
7 |
Snowy |
|
|
1th day |
8 |
Sunny |
|
|
2th day |
8 |
Sunny |
|
|
3th day |
7 |
Sunny |
|
|
4th day |
12 |
Sunny |
|
|
5th day |
16 |
Sunny |
|
|
6th day |
15 |
Partly cloudy |
|
|
28.12.2012 (7th day-second extraction) |
14 |
Stormy |
|
|
8th day |
13 |
Stormy |
|
|
9th day |
12 |
Stormy |
|
|
10 th day |
13 |
Stormy |
|
|
11th day |
13 |
Some clouds |
|
|
12 th day |
13 |
Some clouds |
|
|
13 th day |
13 |
Some clouds |
|
|
04.01.2013 (14th day-third extraction) |
10 |
Foggy |
|
|
15 th day |
11 |
Some clouds |
|
|
16 th day |
10 |
Some clouds |
|
|
17th day |
6 |
Partly cloudy |
|
|
18th day |
6 |
Partly cloudy |
|
|
19th day |
3 |
Partly cloudy |
|
|
20th day |
5 |
Partly cloudy |
|
|
11.01.2013 (21th day-fourth extraction) |
8 |
Stormy |
Methods
Oil extraction
A laboratory scale Abencor extraction system consisted of a small-quantity mill (MC2 Ingenieria Sistemas, Seville, Spain) equipped with a mixer (Kitchen Aid Mixer 4lt Model 5KSM45 220-240VN 50-60 HZ 250W, USA), a basket centrifuge (Marelli Motore Asinciono Trifase Tipo NR90S2) and a metal crusher was used to extract oil from olive fruits. The malaxation process was performed at 35±1 °C for 60 min for Edremit variety and at 35±1 °C for 90 min for Uslu variety, and the oil separation was carried out by dec anter. Extracted olive oils were filtered and then kept at 4°C in amber glass bottles until analysis.
Volatile compound analysis
Sample Preparation. An 8 mL of oil was put in a 20 mL glass headspace sample vial and to attain a final 3 ppm concentration, 27 pL and 24 pL of internal standard solutions (butyl acetate and 1-nonanol, respectively) were added to each vial. The mixture was shaken carefully and allowed to equilibrate for 1 hour in the dark at ambient temperature before the analysis.
HS-SPME procedures. The SPME coated by polydimethylsiloxane (PDMS) fiber at 100 pm thickness and 23 gauge was used in this study. It was purchased from Supelco and thermal conditions provided according to the manufacturer's recommendations before first use. The samples of oils were heated to 40 °C for 10 min before revealing the SPME fiber to the headspace of the sample. Headspace sampling/extraction took 30 min with continuous stirring (250 rpm). The samples were analyzed in duplicate and as a blank sample (empty glass vial) was used before and after each analysis.
GC-MS analysis. The analytical system was constituted from A Gerstel MPS autosampler (Gerstel, Baltimore, MD, USA) installed to an Agilent 6890 N model Gas Chromatography (Little Falls, DE, USA) paired with an Agilent 5975 mass selective detector. The software was MSD ChemStation (Agilent). SPME injections were carried on a splitless mode using a SPME injection sleeve (0.75 mm I.D) at 250 °C for 350 sec meanwhile thermal desorption of analyses was occurred in DB-Wax column (60m*0.25mmLD., 0.25pm film thickness) (J&W Scientific, Folsom, CA, USA). Gas helium was used as a carrier with a total flow of 1.2 mUmin-1. The initial temperature 40 °C was kept for 1.0 min, followed by an increased to 200 °C at a rate of 6 °C min-1 and kept at this temperature for 5 min, then raised to 250 °C at a rate of 8 °C min-1. Lastly, the the temperature was retained 250 °C for 10 min. The total cycle time was 48.92 min. The MS detector was handled in scan mode (mass range 30-500) and the transfer line to the MS system was retained at 250 °C. The identification of the compounds was carried out by comparing (i) the Kovats indices (KI) based on a homologous series of even numbered n-alkanes (C8-C20), with those of standard compounds and by comparison with the data of literature, and (ii) by MS data received from NIST library (NIST/EPA/NIH Mass Spectral Library with Search Program, data version NIST 05, software version 2.0d).
Statistical analysis
XLSTAT (Addinsoft SARL, NY, USA) for Microsoft Excel (Microsoft, Redwood, WA) was used to perform ANOVA. In order to identify the variations of headspace components and analyze the composition data in different samples of oil, principal component analysis (PCA) was performed by SCAN software (Minitab Inc., State College, PA, USA). The software autoscaled the content values before the statistical analysis, i.e. each variable was subtracted by the mean value and the result was divided by its standard deviation.
Results and discussion
Principal volatile compounds are commonly found in great sensory quality virgin olive oil that are synthetized by biogenic pathways of the olive fruit such as fatty acid or amino acid metabolism and LOX pathway (Morales 2005). In spite of that, especially storing types and conditions, climatic conditions are very effective on producing of disagreeable volatiles compounds (Gomes da Silva et al. 2012). In olive fruits stored in batches, under high humidity conditions, the most abundant deuteromycetes such as several species of genus Aspergillus, together with ascomycetes, Penicillium notatum are occurred. These microorganisms have the capacity to oxidise free fatty acids and produce volatile compounds such as methyl ketones (Morales 2005).
In this study, 46 different volatile compounds were identified during different holding times of olive oils extracted from Edremit and Uslu varieties (Table 2, 3 and 4).
Table 2*
Volatile compounds isolated from Edremit (Ayvalik) and and Uslu oils
|
Codes |
Compounds |
tr (min) |
KIe |
KIr |
Odor |
|
|
A1 |
Hexanal (44) |
9.31 |
1103.5 |
1108 |
Fatty; fruity; green |
|
|
A2 |
1-Propanol 2-methyl (43) |
9.31 |
1103.0 |
1103 |
Sweet; musty odor |
|
|
A3 |
Pyridine (79) |
11.62 |
1205.5 |
1193 |
Sour; fishy |
|
|
A4 |
1-Butanol 2-methyl (57) |
11.99 |
1221.5 |
1220 |
Natural |
|
|
A5 |
1-Butanol 3-methyl (70) |
12.00 |
1222.0 |
1224 |
Fusel; alcohol; sweet; fruity |
|
|
A6 |
Limonene (68) |
12.00 |
1222.0 |
1221.5 |
Herbaceous; minty |
|
|
A7 |
2-Hexenal (E) (41) |
12.50 |
1243.6 |
1238 |
Green type flavor |
|
|
A8 |
Cyclodecane methyl (55) |
12.82 |
1257.4 |
1260 |
||
|
A9 |
2-Butanone 3-hydroxy (45) |
14.10 |
1313.1 |
1314 |
Butter; creamy |
|
|
A10 |
Tridecane (57) |
14.15 |
1315.3 |
1300 |
Floral |
|
|
A11 |
5-Hepten-2-one 6-methyl (43) |
15.20 |
1361.8 |
1361 |
Oily; herbaceous; green |
|
|
A12 |
1-Hexanol (56) |
15.37 |
1369.3 |
1362 |
Herbal |
|
|
Codes |
Compounds |
tr (min) |
KIe |
KIr |
Odor |
|
|
A13 |
3-Hexen-1-ol (Z) (41) |
16.14 |
1403.5 |
1406 |
Green |
|
|
A14 |
Nonanal (57) |
16.50 |
1420.1 |
1422 |
Apple; coconut; grape; grapefruit; lemon |
|
|
A15 |
2-Hexen-1-ol (E) (57) |
16.60 |
1424.8 |
1420 |
Apple; banana; orange; green; wine-like; |
|
|
A16 |
Acetic acid (45) |
17.74 |
1477.4 |
1477 |
Pungent; sour; vinegar-like odor |
|
|
A17 |
Cycloisosativene (147) |
18.43 |
1509.8 |
1522 |
||
|
A18 |
n.i. (119) |
19.61 |
1566.9 |
n.d. |
||
|
A19 |
Dimethyl sulfoxide (63) |
20.38 |
1604.3 |
1603 |
Butter; alliaceous (onion; garlic) |
|
|
A20 |
Alpha-Bergamotene (119) |
20.67 |
1619.1 |
1609 |
Woody |
|
|
A21 |
Decanoic acid methyl ester (74) |
20.74 |
1622.7 |
1624 |
Oily; fruity; winelike |
|
|
A22 |
Cycloheptanone 2-methylene (43) |
20.98 |
1634.9 |
n.d. |
||
|
A23 |
Я-Farnesene (69) |
21.85 |
1679.2 |
1674 |
Apple; lavender; lime; green; woody; |
|
|
A24 |
8-Heptadecene (69) |
23.00 |
1739.6 |
1718 |
||
|
A25 |
Eremophilene (161) |
23.31 |
1756.2 |
1744 |
||
|
A26 |
a-Farnesene (93) |
23.75 |
1779.7 |
1778 |
Woody |
|
|
A27 |
Я-Sesquiphellandrene (69) |
24.30 |
1809.6 |
1782 |
Herbal |
|
|
A28 |
Dodecanoic acid methyl ester (74) |
24.73 |
1833.7 |
1834 |
Coconut; creamy; soapy; waxy |
|
|
A29 |
Hexanoic acid (60) |
25.50 |
1876.9 |
1874 |
Cheese; fatty; sour |
|
|
A30 |
Phenylethyl alcohol (91) |
26.85 |
1955.1 |
1946 |
Honey; floral; rose |
|
|
A31 |
2.6-Bis(1.1-dimethylethyl)-4- (1-oxopropyl)phenol (233) |
26.90 |
1958.0 |
n.d. |
||
|
A32 |
4.6-Heptadienoic acid. 3.3.6- trimethyl methyl ester (109) |
27.12 |
1971.0 |
n.d. |
||
|
A33 |
n.i. (159) |
27.29 |
1981.0 |
n.d. |
||
|
A34 |
3-Buten-2-ol. 2-methyl (71) |
27.49 |
1992.7 |
n.d. |
Herbal |
|
|
A35 |
1-Dodecanol (55) |
27.53 |
1995.1 |
1984 |
Coconut; honey; soapy; waxy; earthy; fatty |
|
|
A36 |
Dimethylpalmitamine (58) |
28.03 |
2017.4 |
n.d. |
||
|
A37 |
Methyl tetradecanoate (74) |
28.37 |
2031.7 |
2032 |
Honey; fatty |
|
|
Codes |
Compounds |
tr (min) |
KIe |
KIr |
Odor |
|
|
A38 |
Phenol (94) |
28.45 |
2035.0 |
2035 |
Sweet; tarry odor |
|
|
A39 |
Nerolidol 2 (69) |
28.86 |
2052.2 |
2052 |
Apple; green; woody; citrus; rose |
|
|
A40 |
2(3H)-Furanone dihydro-5- propyl (y-lactone (85) |
29.10 |
2062.3 |
2068 |
Waxy; creamy; coconut character; |
|
|
A41 |
Benzoic acid 2-methoxy. methyl ester (135) |
29.69 |
2087.0 |
2088 |
||
|
A42 |
2H-Pyran-2-one. 6- hexyltetrahydro (99) |
32.70 |
2213.2 |
2215 |
Fruity; sweet |
|
|
A43 |
Hexadecanoic acid methyl ester (74) |
32.75 |
2215.3 |
2214 |
Waxy |
|
|
A44 |
n.i. (71) |
33.80 |
2259.3 |
n.d. |
||
|
A45 |
9-Octadecenoic acid methyl ester (oleic acid) (55) |
37.51 |
2414.8 |
2424 |
Fatty |
|
|
A46 |
p-Isopropenylphenol (134) |
37.76 |
2425.2 |
n.d. |
*KIe. experiment value of Kovats index (KI);
*KIr. reference value of KI.
*The odor descriptors were obtained from SAFC "Flavors and Fragrances. European Ed. Catalogue 2009".
Table 3*
Normalized peak area of volatile compounds isolated from Edremit (Ayvalik) oils in two different packaging at initial and after 7, 14 and 21 days of ripening
|
Codes |
Normalised peak area (mean±SD. n=2) |
||||||||
|
Compounds (m/z) |
Ec |
Ek |
|||||||
|
E0 |
E7C |
E14C |
E21C |
E7K |
E14K |
E21K |
|||
|
A1 |
Hexanal (44) |
(251±11)a |
(29.74± 0.14)b |
n.d.c |
n.d.c |
(9±2)c |
n.d.c |
n.d.c |
|
|
A2 |
1-Propanol 2-methyl '43) |
n.d.b |
n.d.b |
(9±2)a |
(10.6± 0.3)a |
n.d.b |
n.d.b |
n.d.b |
|
|
A3 |
Pyridine (79) |
n.d.b |
(32.7± 0.4)a |
n.d.b |
n.d.b |
n.d.b |
n.d.b |
n.d.b |
|
|
A4 |
1-Butanol 2-methyl ¦57) |
n.d.c |
(1.7± 0.2)bc |
(4.0± 1.0)a |
(5.0± 0.7)a |
(1.32± 0.10)bc |
(1.43± 0.04)bc |
(1.9± 0.2)b |
|
|
A5 |
1-Butanol 3-methyl ¦70) |
n.d.e |
(1.8± 0.3)cd |
(4.0± 0.2)b |
(5.59 ±0.04 )a |
(1.24 ±0.08)d |
(1.73 ±0.11 )cd |
(2.06 ±0.09)c |
|
|
A6 |
Limonene (68) |
(2.70± 0.06)bc |
(40.2± 0.4)a |
(1.95± 0.12)cd |
(0.80± 0.07)e |
(2.8± 0.2)b |
n.d.f |
(1.9± 0.2)d |
|
|
A7 |
2-Hexenal (E) (41) |
(14.0± 1.3)a |
(0.43± 0.09)b |
(0.82± 0.03)b |
n.d.b |
n.d.b |
n.d.b |
n.d.b |
|
|
A8 |
Cyclodecane methyl -55) |
(12.25+ 0.12)d |
(17.66± 0.07)c |
(22.8± 0.6)a |
(21.6± 1.3)ab |
(19.3± 0.14)bc |
(9.6± 0.5)e |
(17.4± 0.8)d |
|
|
A9 |
2-Butanone 3- rydroxy (45) |
n.d.b |
n.d.b |
(5.22± 0.03)a |
(5.85± 0.13)a |
n.d.b |
(1.7± 0.5)b |
(1.8± 1.1)b |
|
|
A10 |
Tridecane (57) |
(2.20± 0.04)a |
(2.0± 0.2)a |
(1.9± 0.4)a |
(2.9± 0.6)a |
(2.51± 0.11)a |
(1.9± 1.0)a |
(1.7± 0.5)a |
|
|
A11 |
5-Hepten-2-one. 6- methyl (43) |
n.d.b |
(2.0± 0.3)ab |
(1.2± 0.3)ab |
(2.6± 0.4)a |
(0.42± 0.11)b |
(0.48 ±0.02 )b |
(1.19± 0.02)ab |
|
|
A12 |
1-Hexanol (56) |
(33±2)f |
(236±9)d |
(503± 11)a |
(268± 3)c |
(356± 4)b |
(119±13)e |
(144.3± 0.2)e |
|
|
A13 |
3-Hexen-1-ol (Z) (41) |
(13.87± 0.11)e |
(52±2)b |
(60.5± 1.4)a |
(51.9± 0.8)b |
(49.4± 0.9)bc |
(30±3)d |
(44.1± 0.4)c |
|
|
A14 |
Nonanal (57) |
(8.7± 1.5)b |
(3.0± 0.4)bc |
(54.9± 1.4)a |
(3.9± 0.4)bc |
(4.32± 2.03)bc |
(1.6± 0.8)c |
n.d.c |
|
|
A15 |
2-Hexen-1-ol (E) (57) |
n.d.d |
(19.3± 0.5)c |
(53.6± 0.5)a |
n.d.d |
(35±3)b |
n.d.d |
(18.2± 0.7)c |
|
|
A16 |
Acetic acid (45) |
(14.1± 0.2)a |
(10.5± 1.1)a |
(11±2)a |
(12±2)a |
(8±2)a |
(7±6)a |
(7.5± 0.7)a |
|
|
A17 |
Cycloisosativene 447) |
n.d.a |
n.d.a |
n.d.a |
n.d.a |
n.d.a |
n.d.a |
n.d.a |
|
|
A18 |
l.i. (119) |
(3.0± 0.3)a |
(2.0± 0.7)a |
(4.41± 0.12)a |
(4.5± 0.2)a |
(6.2± 1.5)a |
(4.2± 0.2)a |
(5.8± 0.2)a |
|
|
A19 |
Dimethyl sulfoxide І53) |
(3.0± 0.2)a |
(0.8± 0.3)b |
(1.18± 0.01)b |
(3.7± 0.7)a |
(0.5± 0.2)b |
(0.75± 0.14)b |
(0.74± 0.04)b |
|
|
A20 |
a-Bergamotene (119) |
(1.99± 0.01)b |
(2.3± 0.3)b |
(2.32± 0.01)b |
(2.25± 0.12)b |
(4.2± 0.9)a |
(1.63 ±0.05)b |
(3.0± 0.2)ab |
|
|
A21 |
Decanoic acid methyl ester (74) |
n.d.b |
n.d.b |
n.d.b |
(31.5± 0.9)a |
n.d.b |
n.d.b |
n.d.b |
|
|
A22 |
Cycloheptanone 2- methylene (43) |
n.d.c |
n.d.c |
(3.1± 0.4)b |
(5.1± 0.2)a |
n.d.c |
n.d.c |
n.d.c |
|
|
A23 |
(E)-Я-Fanesene (69) |
(9.1± 0.3)b |
(10.2± 0.5)b |
(11.2± 0.3)b |
(12.1± 1.0)ab |
(19±5)a |
(7.4± 0.2)b |
(14.0± 0.4)ab |
|
|
A24 |
8-Heptadecene (69) |
n.d.a |
n.d.a |
n.d.a |
n.d.a |
n.d.a |
n.d.a |
n.d.a |
|
|
A25 |
Eremophilene (161) |
(0.79± 0.03)d |
(2.62± 0.03)bc |
(5.3± 0.4)a |
(5.0± 0.2)a |
(3.7± 1.0)abc |
(2.02± 0.07)cd |
(3.8± 0.2)ab |
|
|
A26 |
a-Famesene (93) |
(150± 20)a |
(88± 2)bcd |
(136± 8)ab |
(120± 4)abc |
(110± 40)abc |
(41± 2)d |
(62.8± 0.2)cd |
|
|
A27 |
Я-Sesquiphellandrene (69) |
(8.7± 1.0)ab |
(8.3± 0.6)ab |
(7.3± 0.6)ab |
(8.20± 0.14)ab |
(14± 5)a |
(4.5± 0.2)b |
(8.3± 0.4)ab |
|
|
A28 |
Dodecanoic acid methyl ester (74) |
n.d. b |
n.d. b |
n.d. b |
(27.0± 0.3)a |
n.d. b |
(0.8± 0.3)b |
(0.43 ±0.2)0b |
|
|
A29 |
Hexanoic acid (60) |
(17± 6)a |
(10± 2)ab |
(16.9± 1.3)a |
(20.9± 0.2)a |
(4± 2)b |
(1.7± 1.0)a |
(3± 2)b |
|
|
A30 |
Phenylethyl alcohol (91) |
(5±3)c |
(12±5)abc |
(18±5)ab |
(19.6± 0.7)a |
(9.4± 0.3)abc |
(4.9± 0.8)c |
(7.1± 0.4)bc |
|
|
A31 |
2.6-Bis(1.1- dimethylethyl)-4-(1 - oxopropyl) phenol (233) |
(15±7)a |
(9.32± 0.08)ab |
(10.4± 0.5)ab |
(10.7± 0.8)ab |
(9.74± 0.05)ab |
(0.9± 0.2)b |
(10.1± 0.5)ab |
|
|
A32 |
4.6- Heptadienoic acid 3.3.6- trimethyl. methyl ester (109) |
n.d.a |
(2.1± 1.1)a |
(20± 15)a |
(1.4± 0.6)a |
(7±5)a |
n.d.a |
(1.6±0.9)a |
|
|
A33 |
n.i. (159) |
n.d.c |
(0.96± 0.05)bc |
(1.2± 0.4)ab |
(1.65± 0.14)a |
n.d.c |
n.d.c |
n.d.c |
|
|
A34 |
3-Buten-2-ol 2-methyl (71) |
n.d.b |
(6±5)ab |
(11± 7)ab |
(3.1± 0.5)ab |
(13.1± 0.9)a |
(1.43 0.07)ab |
(2.8± 0.3)ab |
|
|
A35 |
1-Dodecanol (55) |
(8±5)a |
n.d.a |
(1.5± 0.3)a |
n.d.a |
(10± 4)a |
n.d.a |
(0.8± 0.5)a |
|
|
A36 |
Dimethylpalmitamine (58) |
(80±70)a |
n.d.a |
n.d.a |
n.d.a |
(5±4)a |
n.d.a |
n.d.a |
|
|
A37 |
Methyl tetradecanoate (74) |
n.d.b |
n.d.b |
n.d.b |
(27±2)a |
n.d.b |
n.d.b |
n.d.b |
|
|
A38 |
Phenol (94) |
(2.8± 0.9)a |
(2.3± 0.2)a |
(2.66± 0.10)a |
(3.44± 0.09)a |
(2.4± 0.2)a |
(3.5±0.4)a |
(2.21± 0.02)a |
|
|
A39 |
Nerolidol 2 (69) |
n.d.a |
n.d.a |
n.d.a |
n.d.a |
n.d.a |
n.d.a |
n.d.a |
|
|
A40 |
2(3H)-Furanone. dihydro-5-propyl (85) |
(3.1± 0.8)b |
(4.0± 1.2)b |
(7.0± 0.5)a |
(8.65± 0.05)a |
(4.14± 0.13)b |
(2.8±0.3)b |
(3.2±0.3)b |
|
|
A41 |
Benzoic acid. 2- methoxy. methyl ester Щ5) |
(5±2)a |
(1.9± 0.6)ab |
(2.10± 0.09)ab |
(1.3± 0.4)ab |
(2.5± 0.3)ab |
n.d.b |
(0.96± 0.05)ab |
|
|
A42 |
2H-Pyran-2-one. 6- hexyltetrahydro (99) |
(4±2)a |
(5±3)a |
(3±2)a |
(2.0± 0.2)a |
(2.0± 0.7)a |
n.d.a |
n.d.a |
|
|
A43 |
Hexadecanoic acid methyl ester (74) |
(9±4)b |
(5±4)b |
(12±2)b |
(33±5)a |
(5±4)b |
(5.0± 0.3)b |
(6±2)b |
|
|
A44 |
n.i. (71) |
(1.3±0.4)a |
(12± 10)a |
(30± 20)a |
(14.9 ±1.3)a |
(5±3)a |
n.d.a |
(2.2±0.2)a |
|
|
A45 |
9-Octadecenoic acid methyl ester (55) |
(5.77± 0.08)b |
(4±3)b |
(18.0± 0.3)a |
(15± 5)ab |
(6±7)b |
(4.5± 0.7)b |
(8±2)b |
|
|
A46 |
p-Isopropenylphenol (134) |
(1.7± 0.4)b |
(1.6± 0.8)b |
(2.2± 0.8)b |
(1.8± 0.3)b |
(2.4± 0.3)b |
(11± 3)a |
(2.40± 0.09)b |
* Peak areas are normalised respect to internal standard 'n.d. not detected.
a-f Values in the same row with different superscript letters differ significantly (p < 0.05). Data showed mean of two independent tests (mean ±sd).
Table 4*
Volatile compounds (AU x104) isolated from Uslu oils in two different packaging at initial and after 7, 14 and 21 days of stages of ripening
|
Codes |
Normalised peak area (mean±SD. n=2) |
||||||||
|
Compounds (m/z) |
Uc |
Uk |
|||||||
|
U0 |
U7C |
U14C |
U21C |
U7K |
U14K |
U21K |
|||
|
A1 |
Hexanal (44) |
(140.5± 4.6)a |
(51.4± 0.2)b |
n.d.c |
n.d.c |
(52.5± 0.8)b |
n.d.c |
n.d.c |
|
|
A2 |
1-Propanol 2- methyl (43) |
n.d. c |
n.d. c |
(17.54± 0.02)a |
(18.1± 0.2)a |
n.d.c |
(12.2± 1.4)b |
(13.8± 0.08)b |
|
|
A3 |
Pyridine (79) |
n.d.b |
n.db |
n.d.b |
n.d. |
n.d.b |
n.db. |
(7.1± 0.3)a |
|
|
A4 |
1-Butanol 2- methyl (57) |
(1.9± 0.05)c |
(2.9± 1.2)bc |
(11.69± 0.14)a |
(5.0±0.7)b |
(3.1± 0.2)bc |
(1.23± 0.08)c |
(2.12± 0.07)bc |
|
|
A5 |
1-Butanol 3- methyl (70) |
(2.09± 0.04)d |
(3.5± 0.4)d |
(12.8± 0.6)a |
(5.5± 0.3)c |
(3.2± 0.2)d |
(9.3± 0.6)b |
(2.21± 0.02)d |
|
|
A6 |
Limonene (68) |
(0.82± 0.01)b |
(2.42± 0.06)a |
(1.02± 0.02)b |
(1.14± 0.04)b |
(3.00± 0.02)a |
(1.10± 0.14)b |
(1.83± 0.02)ab |
|
|
A7 |
2-Hexenal (E) (41) |
(146±3)a |
(28.3± 0.9)b |
(2.0 ±1.1)c |
(1.00 ±0.00)c |
(37±6)b |
n.d.c |
n.d.c |
|
|
A8 |
Cyclodecane methyl (55) |
(16.3± 0.3)a |
(15.1± 0.4)a |
(10.34± 0.14)c |
(10.9± 1.1)c |
(11.2± 0.2)bc |
(13.1± 0.3)b |
(11.3± 0.2)bc |
|
|
A9 |
2-Butanone 3- hydroxy (45) |
(4.02± 0.11)d |
(9.6± 0.5)cd |
(12.1± 0.2)bcc |
(17.37 ±0.08)b |
(9.0± 0.7)cd |
(39±4)a |
(8.6± 0.4)cd |
|
|
A10 |
Tridecane (57) |
(3.53 ±0.01)a |
(4±2)a |
(2.44± 0.08)a |
(2.3± 0.3)a |
(2.02± 0.08)a |
(3.5± 0.8)a |
(2.32± 0.04)a |
|
|
A11 |
5-Hepten-2-one. 6-methyl (43) |
(1.64± 0.04)de |
(1.4± 0.5)e |
(3.0± 0.3)c |
(3.32± 0.09)bc |
(2.6± 0.2)cd |
(4.52± 0.12)a |
(4.02± 0.06)ab |
|
|
A12 |
1-Hexanol (56) |
-H ^ 00 /--v Vd t 0 |
(186± 2)a |
(91.9± 1.2)c |
(51.3± 0.2)d |
(114± 2)b |
(18.7± 0.2)f |
(34.3± 0.3)e |
|
|
A13 |
3-Hexen-1-ol (Z) (41) |
(5.00± 0.09)a |
(4.3± 0.3)ab |
(2.5± 0.8)bcd |
(2.0± 0.4)cd |
(3.8± 0.2)abc |
n.d.e |
(1.2± 0.2)de |
|
|
A14 |
Nonanal (57) |
(6.2±0.2)a |
(3±2)b |
(2.8± 0.6)b |
(1.3± 0.5)b |
(1.65± 0.12)b |
(1.9± 0.5)b |
(1.75± 0.09)b |
|
|
A15 |
2-Hexen-1-ol (E) (57) |
(30.8± 0.2)a |
(128± 2)a |
(45.1± 0.8)b |
(23.95± 0.11)c |
(71±3)a |
(1.1± 0.3)a |
(22.6± 0.8)a |
|
|
A16 |
Acetic acid (45) |
(21.8± 0.5)a |
(19± 2)a |
(11.6± 0.8)a |
(16.4± 0.4)a |
(13.3± 0.9)a |
(15.01± 0.08)a |
(13± 8)a |
|
|
A17 |
Cycloisosativene (147) |
(1.27± 0.04)a |
(1.81± 0.04)a |
(2.66± 0.05)a |
(2.82± 0.05)a |
(1.66± 0.14)a |
(3.0± 0.3)a |
(2.8± 0.2)a |
|
|
A18 |
n.i. (119) |
(2.32± 0.07)a |
(2.4± 0.2)a |
(1.49± 0.08)b |
(1.69± 0.05)b |
(1.66± 0.01)b |
(1.9± 0.2)b |
(1.7± 0.1)b |
|
|
A19 |
Dimethyl sulfoxide (63) |
(13.3± 0.3)b |
(2.0± 0.3)d |
(14.7± 0.2)a |
(14.0± 0.4)ab |
(2.1± 0.3)d |
(2.2± 0.5)d |
(4.75± 0.13)c |
|
|
A20 |
a-Bergamotene (119) |
(2.32± 0.01)a |
(2.35± 0.03)a |
(1.62± 0.07)bc |
(1.7± 0.2)bc |
(1.42± 0.13)c |
(1.96± 0.01)ab |
(1.7± 0.2)bc |
|
|
A21 |
Decanoic acid methyl ester (74) |
n.d.a |
n.d.a |
n.d.a |
n.d.a |
n.d.a |
n.d.a |
n.d.a |
|
|
A22 |
Cycloheptanone 2-methylene (43) |
n.d.a |
n.d.a |
n.d.a |
n.d.a |
n.d.a |
n.d.a |
n.d.a |
|
|
A23 |
(E)-Я-Farnesene (69) |
(6.70± 0.18)ab |
(7.1± 0.7)a |
(3.8± 0.3)cd |
(4.8± 0.5)bcd |
(3.27± 0.14)d |
(5.5± 0.2)abc |
(4.7± 0.9)cd |
|
|
A24 |
8-Heptadecene (69) |
(7.64± 0.10)a |
(7±2)a |
(2.7± 0.4)b |
(3.1± 0.5)b |
(2.7± 0.3)b |
(3.6± 0.3)b |
(3.7± 0.6)b |
|
|
A25 |
Eremophilene (161) |
(10.7± 0.4)a |
(13.8± 1.2)b |
(12.3± 0.4)bc |
(11.9± 1.0)bc |
(9.6± 1.0)c |
(17.7± 0.3)a |
(11.0± 1.3)bc |
|
|
A26 |
a-Farnesene (93) |
(614±2)a |
(570± 90)a |
(219.70± 0.05)b |
(230± 30)b |
(200± 20)b |
(259± 6)b |
(210± 20)b |
|
|
A27 |
Я- Sesquiphellandre ne (69) |
n.d.a |
n.d.a |
n.d.a |
n.d.a |
n.d.a |
n.d.a |
n.d.a |
|
|
A28 |
Dodecanoic acid. methyl ester (74) |
(1.5± 0.01)a |
(0.7± 0.2)ab |
n.d.b |
n.d.b |
(0.91± 0.13)ab |
(1.11± 0.13)a |
n.d.b |
|
|
A29 |
Hexanoic acid (60) |
(20.4± 0.4)a |
(15.4± 1.3)b |
(8±2)cd |
(3.4± 0.7)ef |
(9.9± 0.5)c |
(4.1± 0.2)de |
n.d.f |
|
|
A30 |
Phenylethyl alcohol (91) |
(6.20± 0.12)b |
(6.7± 0.3)b |
(80± 30)a |
(28.6± 0.6)b |
(6.9± 0.2)b |
(23.4± 0.8)b |
(18.2± 0.8)b |
|
|
A31 |
2.6-Bis(1.1- dimethylethyl)-4- (1-oxopropyl) phenol (233) |
(9.70± 0.13)ab |
(10.6± 0.7)a |
(10.06± 0.04)ab |
(9.10± 0.11)b |
(9.4± 0.4)ab |
(10.3± 0.5)ab |
(8.95± 0.070b |
|
|
A32 |
4.6-Heptadienoic acid 3.3.6- trimethyl. methyl ester (109) |
n.d.b |
(5±3)ab |
(7.8± 1.4)a |
(1.4± 0.6)b |
n.d.b |
(0.94± 0.08)b |
(1.4± 0.5)b |
|
|
A33 |
n.i. (159) |
(7.72± 0.13)a |
(3±2)b |
(4.54± 0.10)ab |
(2.4± 0.5)ab |
(1.4± 0.6)b |
(2±2)b |
(2.3± 0.2)ab |
|
|
A34 |
3-Buten-2-ol. 2- methyl (71) |
(3.31± 0.10)a |
n.d.b |
n.d.b |
n.d b |
n.d.b |
n.d.b |
n.d.b |
|
|
A35 |
1-Dodecanol (55) |
n.d. a |
n.d. a |
n.d. a |
n.d. a |
n.d. a |
n.d. a |
n.d. a |
|
|
A36 |
Dimethylpalmita mine (58) |
(8.2± 0.2)a |
(8.1± 0.6)a |
(16±5)a |
(12±6)a |
(4.0± 0.4)a |
(6.8± 0.9)a |
(7.3± 0.7)a |
|
|
A37 |
Methyl tetradecanoate (74) |
n.d.a |
n.d.a |
n.d.a |
n.d.a |
n.d.a |
n.d.a |
n.d.a |
|
|
A38 |
Phenol (94) |
(3.43± 0.07)b |
(2.2± 0.4)c |
(9±2)a |
(6.18± 0.09)b |
(2.0± 0.5)c |
(3.43± 0.08)bc |
(3.08± 0.09)bc |
|
|
A39 |
Nerolidol 2 (69) |
(54±2)a |
(21±10)b |
(15±2)bc |
(3.3±0.8)c |
(3.0± 1.4)c |
(7.0± 0.2)bc |
(2.59± 0.04)c |
|
|
A40 |
2(3H)-Furanone dihydro-5-propyl (85) |
(8.07± 0.12)b |
(9±2)b |
(25±9)a |
(5.9± 0.7)b |
(4.6± 0.3)b |
(12.44± 0.04)ab |
(4.21± 0.04)b |
|
|
A41 |
Benzoic acid. 2- methoxy. methyl ester (135) |
(18.0 ±0.5)a |
(7.4± 0.5)b |
(3.7± 1.3)c |
(1.2±0.2)d |
(2.79± 0.04)cd |
(2.73± 0.02)cd |
(1.7± 0.2)cd |
|
|
A42 |
2H-Pyran-2-one. 6- hexyltetrahydro (99) |
(14.83 ±0.50)a |
(11 ±5)ab |
(10.8 ±0.8 )ab |
(1.8 ±0.2)c |
(2.1 ±0.6)c |
(5.5 ±0.3 )bc |
(1.3 ±0.2)c |
|
|
A43 |
Hexadecanoic acid methyl ester (74) |
(5.30 ±0.08)a |
(4.6 ±0.8)a |
(60 ±60)a |
(2.8 ±0.4)a |
(2.7 ±0.3)a |
(3.23 ±0.10)a |
(4.1 ±1.4)a |
|
|
A44 |
n.i. (71) |
n.d.b |
(1.4 ±0.5)ab |
(5.7 ±0.4)a |
n.d.b |
n.d.b |
(7.6 ±1.2)a |
n.d.b |
|
|
A45 |
9-Octadecenoic acid methyl ester (55) |
(4.63± 0.14)a |
(7±4)a |
(15± 6)a |
(3.03± 1.85)a |
(3.8± 1.0)a |
(3.3±1.0)a |
(6±2)a |
|
|
A46 |
P- Isopropenylphen ol (134) |
(2.16± 0.07)a |
(2.5± 0.8)a |
(2.1± 0.3)a |
(1.90± 0.05)a |
(1.6± 0.3)a |
(2.14± 0.10)a |
(1.90± 0.05)a |
'n.d. not detected.
Data showed mean of two independent tests (mean ±sd).
a-c Values in the same row with different superscript letters differ significantly (p < 0.05).
The storage of olives in inappropriate conditions had a negative impact on the aroma profiles of oils. Uslu olive oil was characterized with high concentrations of terpene volatile compound such as a-Farnesene (614±2) and aldehydes as 2-hexenal (146±3) and hexanal (140.5±4.6). In contrast, Edremit olive oil had lower concentrations of a-Farnesene and 2- exenal, which were determined as 150±20 and 14±1.3, respectively. The increase of concentration of 2-hexanal (E) during holding periods could be explained by the activity of the fungal enzymes in LOX pathway of olive fruits (Schnurer et al. 1999). However, the concentration of hexanal (251±11) in Edremit olive oil was immediately increased after extraction. In this study, from alcohol compounds 1-Hexanol and 3-Hexen-1-ol were found as the most potent volatiles of the Edremit oils, which concentration increased over holding time in both holding types. In Uslu olive oils, the concentration of 1 -hexanol also increased significantly (p<0. 05) during the holding time as observed for Edremit oil. The concentrat...
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