1 “Salt reduction in slow fermented sausages affects the generation of aroma active 1 compounds” 2 Sara Corral, Ana Salvador, Mónica Flores* 3 4 Instituto de Agroquímica y Tecnología de Alimentos (IATA-CSIC) Avda. Agustín Escardino 7, 5 46980 Paterna, Valencia, Spain 6 7 Corresponding author. Tel.: +34 96 3900022; fax: +34 96 3636301 8 E-mail address: [email protected] (M. Flores). 9 10 11
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1
“Salt reduction in slow fermented sausages affects the generation of aroma active 1
compounds” 2
Sara Corral, Ana Salvador, Mónica Flores* 3
4
Instituto de Agroquímica y Tecnología de Alimentos (IATA-CSIC) Avda. Agustín Escardino 7, 5
Kovats, E.S. (1965). Gas chromatographic characterization of organic substances in the 530
retention index system. In J. C. Giddings, & R. A. Keller (Eds.), Advances in 531
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Leroy, F., Verluyten, J., & De Vuyst, L. (2006). Functional meat starter cultures for improved 533
sausage fermentation. International Journal of Food Microbiology, 106, 270-285. 534
Marco, A., Navarro, J. L., & Flores, M. (2004). Volatile compounds of dry-fermented sausages 535
as affected by solid-phase microextraction (SPME). Food Chemistry, 84, 633-641. 536
Marco, A., Navarro, J. L., & Flores, M. (2006). The influence of nitrite and nitrate on microbial, 537
chemical and sensory parameters of slow dry fermented sausage. Meat Science, 73, 538
660-673. 539
Marco, A., Navarro, J. L., & Flores, M. (2007). Quantitation of selected odor-active constituents 540
in dry fermented sausages prepared with different curing salts. Journal of Agricultural 541
and Food Chemistry, 55, 3058-3065. 542
Marco, A., Navarro, J. L., & Flores, M. (2008). The sensory quality of dry fermented sausages 543
as affected by fermentation stage and curing agents. European Food Research and 544
Technology, 226, 449-458. 545
Meynier, A., Novelli, E., Chizzolini, R., Zanardi, E., & Gandemer, G. (1999). Volatile compounds 546
of commercial Milano salami. Meat Science, 51, 175-183. 547
Olesen, P. T., Meyer, A. S., & Stahnke, L. H. (2004). Generation of flavour compounds in 548
fermented sausages - The influence of curing ingredients, Staphylococcus starter 549
culture and ripening time. Meat Science, 66, 675-687. 550
Olivares, A., Navarro, J. L., Salvador, A., & Flores, M. (2010). Sensory acceptability of slow 551
fermented sausages based on fat content and ripening time. Meat Science, 86, 251-552
257. 553
Olivares, A., Navarro, J. L., & Flores, M. (2011). Effect of fat content on aroma generation 554
during processing of dry fermented sausages. Meat Science, 87, 264-273. 555
Ordóñez, J.A., Hierro, E.M., Bruna, J.M., De La Hoz, L. (1999). Changes in the components of 556
dry-fermented sausages during ripening. Critical Reviews in Food Science and Nutrition, 557
39, 329-367. 558
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Hyphenated Headspace-Gas Chromatography-Sniffing Technique: Screening of Impact 560
Odorants and Quantitative Aromagram Comparisons. Journal of Agricultural and Food 561
Chemistry, 45, 2630-2637. 562
Ravyts, F., Steen, L., Goemaere, O., Paelinck, H., De Vuyst, L., & Leroy, F. (2010). The 563
application of staphylococci with flavour-generating potential is affected by acidification 564
in fermented dry sausages. Food Microbiology, 27, 945-954. 565
Ruusunen, M.M & Puolanne, E. (2005). Reducing sodium intake from meat products. Meat 566
Science, 70, 531-541. 567
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Sárraga, C., & García-Regueiro, J. A. (1998). Oxidation of microsomal fraction in the 568
processing conditions of dry-cured ham. The in-vitro effect of brine. Meat Science, 50, 569
295-302. 570
Schmidt, S., & Berger, R. G. (1998a). Aroma Compounds in Fermented Sausages of Different 571
Origins. LWT - Food Science and Technology, 31, 559-567. 572
Schmidt, S., & Berger, R. G. (1998b). Microbially formed aroma compounds during the 573
maturation of dry fermented sausage (salami). Advances in Food Sciences, 20, 144-574
152. 575
Shahidi, F., Rubin, L. J., & Wood, D. F. (1988). Stabilization of meat lipids with nitrite-free 576
curing mixtures. Meat Science, 22, 73-80. 577
Söllner, K., & Schieberle, P. (2009). Decoding the key aroma compounds of a Hungarian-type 578
salami by molecular sensory science approaches. Journal of Agricultural and Food 579
Chemistry, 57, 4319-4327. 580
Stahnke, L. H. (1995a). Dried sausages fermented with Staphylococcus xylosus at different 581
temperatures and with different ingredient levels - Part II. Volatile components. Meat 582
Science, 41, 193-209. 583
Stahnke, L. H. (1995b). Dried sausages fermented with Staphylococcus xylosus at different 584
temperatures and with different ingredient levels - Part III. Sensory evaluation. Meat 585
Science, 41, 211-223. 586
Talon, R., Chastagnac, C., Vergnais, L., Montel, M. C., & Berdagué, J. L. (1998). Production of 587
esters by staphylococci. International Journal of Food Microbiology, 45, 143-150. 588
Tjener, K., Stahnke, L. H., Andersen, L., & Martinussen, J. (2004). The pH-unrelated influence 589
of salt, temperature and manganese on aroma formation by Staphylococcus xylosus 590
and Staphylococcus carnosus in a fermented meat model system. International Journal 591
of Food Microbiology, 97, 31-42. 592
Zanardi, E., Ghidini, S., Conter, M., & Ianieri, A. (2010). Mineral composition of Italian salami 593
and effect of NaCl partial replacement on compositional, physico-chemical and sensory 594
parameters. Meat Science, 86, 742-747. 595
596
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Figure legends 597
598
Figure 1. Changes in pH, Aw (A) and TBARS (B) during the ripening of dry fermented 599
sausages: S (control, ○), RS (16 % reduced salt, ∇) and RSK (16% KCl to replace NaCl, □) 600
601
602
603
604
605
606
607
608
609
610
611
612
613
614
615
616
617
618
Figure 2. Total volatile compounds abundance expressed as AU x 106 in the headspace of dry 619
fermented sausages with different salt content: S (control), RS (16 % reduced salt) and RSK 620
(16% KCl to replace NaCl) at the end of the ripening process. Different letters in the same 621
chemical group indicate significant differences (p<0.05) among treatments. 622
623
624
625
626
627
628
629
630
631
632
633
19
S1
S2
S3
RS1
RS2
RS3
RSK1
RSK2
RSK3
3-methyl butanal
pentanal
Hexanal
2-hexenal
Benzeneacetaldehyde
nonanal2-nonenal
2,3-butanedione
2-ethylfuran
2-octanone 2-nonanone
Methanethiol
3-methyl thiophene3-methyl thiopropanal
Dimethyl trisulfide
Acetic acidButanoic acid
Heptanoic acid
1-pentanol
1-octen-3-ol
4-methylphenolEthyl butanoate
Butyl acetate
D-Limonene
pH
Moisture
Fat
Protein
TBARS
Na+
K+
Cl-
Hardness
SpringinessCohesiveness
Chewiness
-13
-3
7
-20 -10 0 10 20
PC2
(18.
05 %
)
PC1 (39.83 %)
2-hydroxy benzaldehyde
Figure 3. Loadings of the first two principal components (PC1-PC2) of the analyzed parameters 634
(pH, TBARS, ions, texture parameters and aromatic active compounds) of fermented sausages 635
with different salt content: S (control), RS (16 % reduced salt) and RSK (16% KCl to replace 636
NaCl) at the end of the ripening process. 637
638
1
Table 1. Chemical composition and ion contents in dry fermented sausages with different salt content: S (control), RS (16 % reduced salt) and RSK (16% KCl to replace NaCl) at the end of the ripening process (57 days).
S RS
(red16%) RSK
(red16% +KCl) P
Moisture (%) 49.51
48.06
49.23
ns
Fat (%) 10.75
12.73
12.32
ns
Protein (%) 35.32ab
37.00
34.88b
ns
Na+ (g/100 g d.m.) 3435.38 a 3074.55 ab 2748.67 b ***
K+ (g/100 g d.m.) 952.26 b 996.35 b 1458.14 a ***
Cl- (g/100 g d.m.) 3257.52
2946.78
2992.77
ns P: P value of salt content effect. *** P<0.001, ** P<0.01, * P<0.05, ns: P>0.05. Identical letters in each row indicate the absence of differences at p>0.05 (Fisher test).
Table 2. Texture parameters of dry fermented sausages with different salt content: S (control), RS (16 % reduced salt) and RSK (16% KCl to replace NaCl).
S
RS (red16%)
RSK (red16%
+KCl) P
Hardness (N) 257.85
245.43
246.23 ns
(22,60)
(17.22)
(14.64)
Adhesiveness (N·s) -3.34
-3.26
-3.68
ns
(0.54)
(0.47)
(0.58)
Springiness 0.63
0.61
0.61
ns
(0.02)
(0.03)
(0.03)
Cohesiveness 0.64 a 0.62 b 0.62 b *
(0.02)
(0.02)
(0.01)
Chewiness 103.49 a 93.11 b 93.24 b **
(9.21)
(8.96)
(7.94)
PS: P value of salt content effect. *** P<0.001, ** P<0.01, * P<0.05, ns: P>0.05. Identical letters in each row indicate the absence of differences at p>0.05 (Fisher test).The values represent the mean and (standard deviation).
Table 3. Sensory acceptability of dry fermented sausages with different salt content: S (control), RS (16 % reduced salt) and RSK (16% KCl to replace NaCl) at the end of the ripening process.
S
RS (red16%)
RSK (red16%
+KCl) P Appearance 6.14
5.86
5.96
ns
(1.57)
(1.41)
(1.48)
Aroma 6.33 a 5.93 b 5.89 b *
(1.46)
(1.37)
(1.44)
Taste 5.96 a 5.34 b 5.84 a **
(1.89)
(1.80)
(1.94)
Tenderness 6.13
6.00
6.18
ns
(1.64)
(1.69)
(1.61)
Juiciness 6.22 a 5.75 b 5.99 ab *
(1.63)
(1.60)
(1.58)
Overall quality 5.92 a 5.54 b 5.92 a * (1.72) (1.61) (1.78)
PS: P value of salt content effect. *** P<0.001, ** P<0.01, * P<0.05, ns: P>0.05. Identical letters in each row indicate the absence of differences at p>0.05 (Fisher test). The values represent the mean and (standard deviation).
2
Table 4. Volatile compounds (expressed as AU x 106 extracted by HS-SPME) identified in the headspace of dry fermented sausages with different salt content: S (control), RS (16 % reduced salt) and RSK (16% KCl to replace NaCl) at the end of the ripening process.
Sausage Batches
Compound LRI B RIC S RS
(red16%)
RSK (red16%
+KCl) SEM PD
Lipid autooxidation Pentane 500 a 8.25 c 19.98 b 32.45 a 1.66 ***
Propanal 524 a 4.78
11.00
9.78
2.62 ns Isopropyl alcohol 542 a 3.26
6.58
10.41
1.92 ns
Hexane 600 a 12.05 a 5.81 b 5.88 b 1.32 * 1-Propanol (31)A 613 a 0.06 b 0.11 a 0.09 ab 0.01 * 2-Methylfuran (82)A 615 a 1.23
1.21
0.69
0.15 ns
Butanal 622 a 0.56 b 1.41 b 3.04 a 0.27 ** 1-heptene (55)A 693 a 0.03 b 0.25 a 0.31 a 0.03 ** Heptane (71)A 700 a 1.84
5.55
5.31
1.19 ns
2-Ethylfuran (81)A 720 a 1.55 b 1.13 b 3.11 a 0.32 * Pentanal (44)A 737 a 18.82
33.63
33.67
5.19 ns
Octane 800 a 25.95 b 60.93 a 37.00 b 5.21 * 2-octene 810 a 13.15
8.91
6.13
1.66 ns
1-Pentanol 826 a 9.35 b 12.22 b 17.79 a 1.11 ** Hexanal (44)A 840 a 72.90 b 92.41 b 137.28 a 10.45 * Nonane 900 a 3.14
2.56
2.36
0.28 ns
2-Hexenal (Z) 904 a 1.84
1.47
2.56
0.39 ns 2-Butylfuran 908 a 1.71
2.06
1.88
0.25 ns
1-Hexanol 922 a 28.19
45.87
37.14
5.18 ns Heptanal 940 a 19.06
54.79
55.22
9.72 ns
Decane 1000 a 1.81
1.84
1.85
0.20 ns 2-Penthylfuran 1009 a 3.61 b 8.73 ab 11.78 a 1.51 * Octanal 1047 a 19.79
31.80
33.30
3.36 ns
Hexanoic acid 1075 a 37.54
42.70
43.92
2.15 ns 2-Ethyl 1-hexanol 1082 a 6.89
7.54
8.00
0.60 ns
Undecane (57)A 1100 a 0.16
0.15
0.18
0.02 ns 2-Octenal (Z) 1115 a 1.03 b 1.88 b 4.24 a 0.64 * 1-Octanol 1123 a 1.02 b 2.84 a 2.74 a 0.40 * Nonanal 1149 a 28.86
37.94
37.95
3.62 ns
Heptanoic acid 1165 a 2.03 b 3.23 a 2.16 b 0.29 * Dodecane 1200 a 6.32
7.19
5.36
0.62 ns
2-Nonenal (Z) 1221 a 2.12
3.09
2.90
0.39 ns Decanal 1256 a 1.99
2.36
1.73
0.35 ns
Octanoic acid 1266 a 87.82 a 35.80 b 36.79 b 5.78 *** 2,4-Nonadienal (E, E) 1287 a tr.
tr.
tr.
Tridecane 1300 a 2.83 a 2.05 ab 1.39 b 0.24 * Nonanoic acid 1357 a 3.20
2.83
2.85
0.16 ns
Decanoic acid 1449 a 7.98
6.80
6.97
0.90 ns Total
442.70 b 566.66 a 606.23 a 36.77 *
Bacterial metabolism Lipid β oxidation 2,3-Pentanedione (85)A 744 a 0.17
0.14
0.08
0.03 ns
2-Heptanone 933 a 4.64
7.88
7.70
1.10 ns 2-Heptanol 946 a 5.92
4.32
4.01
0.67 ns
1-Octen-3-ol (57)A 1030 a 2.13
2.01
3.80
0.56 ns 2-Octanone 1039 a 0.62
0.61
0.90
0.09 ns
2-Nonanone 1140 a 5.60 a 3.01 b 3.78 b 0.29 ** 2-Undecanone 1306 a 1.27
1.25
1.11
0.16 ns
Total
20.36
19.22
21.38
2.20 ns Carbohydrate fermentation
Acetaldehyde 466 a 9.94
12.44
10.67
0.67 ns Ethanol 508 a 13.11 c 96.86 a 49.08 b 12.11 ** Acetone 530 a 20.48
27.79
24.48
4.18 ns
2,3-Butanedione (43)A 626 a 0.52 a 0.34 b 0.30 b 0.04 * 2-Butanone 631 a 28.96
30.95
28.48
2.41 ns
3
Acetic acid 737 a 1447.65
1295.19
1228.50
59.09 ns 2,3-Butanediol 887 a 1.63 a 0.26 b 0.33 b 0.25 * Butanoic acid 892 a 72.74
80.23
82.45
4.31 ns
Total
1595.03
1544.06
1424.30
75.20 ns Amino acid degradation
2-Methyl propanal 594 a 7.42
7.38
5.59
1.06 Ns Ethyl methyl sulfide (61)A 624 a 0.98 a 0.79 a 0.41 b 0.10 * Benzene 675 a 0.95
1.00
1.20
0.13 Ns
2-Methyl 1-propanol 682 a 0.36
0.20
0.31
0.08 Ns 3-Methyl butanal (44)A 689 a 8.89
9.32
8.36
0.96 Ns
2-Methyl butanal (58)A 700 a 2.50
2.30
2.11
0.21 Ns Dimethyl disulfide 772 a 4.40 a 3.11 ab 2.06 b 0.51 * Toluene 788 a 12.83
14.11
13.63
0.76 Ns
3-Methyl-3-buten-1-ol (41)A 789 a 0.30
0.24
0.29
0.05 Ns 3-Methyl thiophene 794 a 125.16 a 68.25 b 42.68 b 6.88 *** 3-Methyl 2-butenal (55)A 840 a 14.73 b 17.74 b 28.74 a 2.61 * Ethyl benzene 883 a 2.46
2.74
2.90
0.20 Ns
2,5-dimethyl pyrazine 944 a 2.81
2.53
2.42
0.52 Ns 3-Methyl thiopropanal 966 a 6.24 b 9.89 a 11.66 a 0.75 ** Dimethyl trisulfide 1002 a 1.80
1.25
1.01
0.20 Ns
Benzaldehyde 1017 a 16.33 b 21.55 a 22.29 a 1.40 * 2-Hydroxy benzaldehyde (122)A 1100 a 0.27
0.27
0.28
0.01 Ns
Benzeneacetaldehyde 1107 a 3.69 c 6.82 a 5.65 b 0.30 *** Phenol 1111 a 75.55
74.23
73.78
2.99 ns
Benzyl alcohol 1120 b 1.63
1.66
1.53
0.05 ns Phenylethyl alcohol (91)A 1194 a 0.39 b 2.32 a 0.92 b 0.16 *** Total
289.69 a 247.69 b 227.82 ab 16.78 ns
Staphylococci esterasa activity Methyl acetate 551 a 2.70
1.98
1.62
0.27 ns
Ethyl acetate 635 a 6.76 b 26.99 a 13.21 b 2.58 ** Ethyl propanoate (57)A 744 a 0.27
0.62
0.47
0.12 ns
Ethyl butanoate (71)A 831 a 0.28 c 2.90 a 1.29 b 0.30 ** Butyl acetate 847 a 2.05
2.55
4.69
0.64 ns
Ethyl 2-hydroxy-propanoate 869 a 1.78 b 16.45 a 1.97 b 0.44 *** Ethyl hexanoate (88)A 1028 a 0.10 c 1.22 a 0.71 b 0.09 *** Ethyl octanoate 1229 a 2.73
4.42
3.14
0.83 ns
Total
16.68
57.12
27.09
9.78 ns Unknown or contaminants compound
Methanethiol 472 a 7.83
9.17
9.84
0.47 ns Carbon disulfide 537 a 13.78
7.75
8.53
1.59 ns
o-Xylene 916 a 3.24
3.23
3.33
0.23 ns Styrene 918 a 1.61
1.27
1.36
0.15 ns
2-Butoxyetanol 952 a 2.35
2.74
2.87
0.31 ns Butyrolactone 1023 a 5.07
7.15
6.49
0.82 ns
p-Cymene 1050 a 1.81
1.72
2.00
0.13 ns D-Limonene 1045 a 4.48
4.85
5.03
0.20 ns
Dimethyl sulfone 1061 a 1.27 b 1.37 b 1.61 a 0.06 * Methyl 2,4-hexadienoate (67)A 1065 b 0.19 a 0.22 a 0.06 b 0.01 *** Ethyl 2,4-hexadienoate 1144 a 3.13 b 7.72 a 3.57 b 0.75 * Sorbic acid 1179 a 342.07 a 397.89 a 91.74 b 42.89 ** 4-Methyl-phenol (107)A 1195 a 0.46
0.58
0.43
0.04 ns
Total 387.29
445.65
136.87
82.35 ns AU: Abundance units, the result of counting the total ion chromatogram (TIC) for each compound. A Target ion used to quantify the compound when the peak was not completely resolved. B Linear retention indices (LRI) of the compounds eluted from the GC-MS using a DB-624 capillary column (J&W Scientific 30 m x 0.25 mm i.d. x 1.4 µm film thickness). C Reliability of identification: a, identification by mass spectrum and by coincidence with the LRI of an authentic standard; b, tentatively identification by mass spectrum. D p value of salt content effect. ***: p<0.001, **: p<0.01, *: p<0.05, ns: p>0.05. Means followed by different letters in the same compound indicate significant differences (p<0.05) among batches.
4
Table 5. Odor active compounds identified in the HS of dry fermented sausages
A Linear retention indices (LRI) of the compounds or standards eluted from the GC-FID-O using a DB-624 capillary column (J&W Scientific 60 m x 0.32 mm i.d. x 1.8 µm film thickness). BDF Detection frequency value C Previously reported in dry fermented sausages by: 1 Stahnke (1994), 2 Stahnke (1995b), 3 Schmidt and Berger(1998a), 4 Schmidt and Berger (1998b), 5 Meynier et al. (1999), 6 Chevance et al. (2000), 7 Blank et al. (2001), 8 Marco et al. (2007), 9 Söllner et al. (2009), 10 Gianelli et al. (2011), 11 Olivares et al. (2011).