Article pp.234-244 du Vol.27 n°3 (2007)

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ARTICLE ORIGINAL ORIGINAL PAPER

Fatty acid and volatile compound composition of Italian and Brazilian Milano salami

R. M.L. de Campos¹, E. Hierro¹, J. A. Ordóñez², L. de la Hoz¹^*

SUMMARY

Twenty Milano salamis, ten manufactured and bought in Italy and another ten in Brazil, were analysed in order to compare the general chemical composition, the fatty acid profile and the volatile compounds. All samples achieved the legal requirements of their respective countries. Only small var- iations were observed, showing Italian salamis higher C18:0, C18:3(n−3) and lower C18:1(n−9) contents and also a lower PUFA n−6/n−3 ratio. The analysis of volatiles showed 95 compounds, being 84 of them identified as aldehydes (15), alcohols (13), hydrocarbons (13), ketones (11), esters (10), terpenes (10), acids (7), sulphur compounds (4) and furans (1). Differences between Italian and Brazilian salamis were found in all groups of volatile compounds classified according to their origin.

Keywords

Italian and Brazilian Milano salamis, fatty acids, volatile compounds.

1 – INTRODUCTION

Milano salami is a dry fermented sausage and, probably, the most repre- sentative of Italian salamis. It is prepared with lard and lean meat (pork or a mix of pork and beef). This meat product is widely manufactured throughout the world although the quality standards are from those manufactured in Italy. Sev- eral papers dealing with different aspects of salamis i.e. lipid and colour stability (ZANARDI et al., 2002), oxidative stability (ZANARDIet al., 2000), incorporation of

1. Departamento de Nutrición – Bromatología y Tecnología de los Alimentos – Facultad de Veterinaria – Uni- versidad Complutense de Madrid – Avda. Puerta de Hierro s/n – 28040 Madrid – Spain.

2. Instituto de Ciencia y Tecnología de la Carne – Universidad Complutense de Madrid – Avda. Puerta de Hierro s/n – 28040 Madrid – Spain.

* Corresponding author. Tel.: +34-91-3943745 – fax: +34-91-3943743 – E-mail address: [email protected]

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polyunsaturated fatty acids (PUFA) and salami quality (WARNANTS et al., 1998), volatile compounds (MEYNIER et al., 1999) have been published.

Brazil is one of the main pork producers with 3,110,000 tons in 2004 (FAOSTAT, 2005). Approximately 84% of the production was used for local con- sumption and 70% of that as processed meat (FAS online, 2005). In order to satisfy market, manufacturers adequate their meat formulation and sensorial characteristic of products to country or local nutritional and/or organoleptic habits although some rules are dictated by the different governments. These products are regulated by the Norma Italiana Salame Italiano (UNI, 1996) and the Regulamento Técnico de Identidade e Qualidade do Salame tipo Milano (MAA, 2000), in Italy and Brazil, respectively.

Taking into account the various origins and methods of production of Milano salami, differences in composition should be expected, which are of interest from a technological, sensorial or nutritional point of view. The purpose of the present work was to study the general chemical composition, the fatty acid composition and the volatile compounds of Milano salami manufactured in Italy and Brazil to check if Brazilian products have similar chemical characteristics to those elaborated in Italy. This fact would give a better comprehension of the Milano salami produced in Brazil.

2 – MATERIALS AND METHODS

2.1 Samples

Ten commercial Milano salamis all of them from different branches manufactured in Italy and, also, another ten produced in Brazil were purchased from retail shops in their respectively countries. All salamis were unsmoked and had diameters between 50 and 70 mm. Their labels indicated pork and lard as unique meat ingredient.

2.2 Chemical analysis

Protein (Kjeldhal nitrogen), moisture (oven air-drying method) and ash (muffle furnace) were analysed following AOAC (1995) procedure. Water activity (a_w) was determined using a Decagon CX1 hygrometer (Decagon Devices Inc., Pull- man, WA) at 25˚C. The pH was measured in a homogenate of the sample with distilled water (1:10) (w/v) using a Crison Digit-501 pH meter (Crison Instru- ments, Barcelona, Spain).

Lipids from adipose tissue samples were obtained using the method of Bligh and Dyer (HANSON and OLLEY, 1963) and 300 mg of lipids were methylated in the presence of 3 ml of sodium metal (0.1 N in methanol) and 3 ml of sulphuric acid (5% in anhydrous methanol) to obtain the fatty acid methyl esters (SANDLER and KARO, 1992). The methyl esters were extracted with 3 ml of petroleum ether. Then, 1 μl was analysed using a Perkin Elmer 8420 (Perkin-Elmer, Beaconsfield, UK) gas chromatograph equipped with a flame ionization detector and a capillary column

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HP-Innowax (30 m × 0.32 mm i.d. and 0.25 μm). Helium at 2.0 ml/min was used as the carrier gas and the split/splitless injector was used with a split/splitless ratio of 10/1. The temperature program was as follows: injector and detector temperature 250˚C, the initial column temperature was 200°C, which was kept for 2 min, 200˚C to 245˚C at 3.5˚C/min, hold for 7 min. Fatty acid methyl esters were identified by comparison with standards run previously. Analyses were done by duplicate.

Lipid oxidation was determined using the 2-thiobarbituric acid method (TBARs) described by SALIH et al. (1987). For that, 5 g of salami were homoge- nised in 15 ml of 0.38 M HClO₄ for 3 min in an ice bath. To avoid further oxidation 0.5 ml of a 0.19 M BHT ethanolic solution was added. The homogenate was centrifuged (3000 g, 5 min, 5ºC) and filtered through Whatman No. 54. An aliquot of 0.7 ml was mixed with 0.7 ml of a 0.02 M TBA solution and heated at 100ºC for 30 min. After cooling, the mixture was centrifuged at 3000 g for 15 min at 5ºC. Finally, the absorbance was measured at 532 nm. Results were expressed as mg malondialdehyde/kg sample.

The extraction of the volatile compounds was performed using solid-phase microextraction (SPME). A SPME device (Supelco, Bellefonte, PA, USA) con- taining a fused-silica fibre (10 mm length) coated with a 75 μm layer of Car- boxen-PDMS (polydimethylsiloxane) was used. Salami was ground with a commercial grinder and 1 g was transferred to a 4 ml vial. The vial was screw- capped with a laminated Teflon-rubber disk. The needle of the SPME holder was inserted into the sample vial through the septum and then the fibre was exposed to the headspace. The fibre was conditioned prior to analysis by heat- ing it in a gas chromatograph injection port at 300ºC for 60 min. Extraction was performed at 35ºC for 30 min. Before extraction, samples were equilibrated for 15 min at the same temperature used for extraction. Once sampling was fin- ished, the fibre was withdrawn into the needle and transferred to the injection port of the gas chromatograph-mass spectrometer (GC-MS) system. Duplicate analyses were conducted.

Analyses were performed on a Hewlett-Packard 5890 Series II gas chromatograph fitted with a HP5972 mass spectrometer and a G1034 Chemstation (Hewlett-Packard, Palo Alto, CA, USA). A split/splitless injection port, held at 250ºC, was used to thermally desorb the volatiles from the SPME fibre onto the front of a CP-Sil 8 CB low bleed/MS fused silica capillary column (60 m ✕

0.25 mm i.d., 0.25 μm film thickness, Chrompack, Middelburg, The Nether- lands). The injection port was in splitless mode, the split valve opening after 3 min. Immediately before the desorption of the fibre, 0.1 μl of an internal standard (131 ng of 1,2-dichlorobenzene in 1 μl of methanol) were injected into the gas chromatograph. During a desorption period of 5 min, volatile compounds were cryofocused by immersing 15 cm of column adjacent to the heater in a solid CO₂ bath while the oven was held at 40°C. After desorption, the bath was then removed and chromatography achieved by holding at 40°C for 2 min fol- lowed by a programmed rise to 280°C at 4°C/min and held for 5 min. A series of n-alkanes (C₆-C₂₂) (Sigma) was analysed under the same conditions to obtain linear retention index (LRI) values for the aroma components.

The mass spectrometer was operated in electron impact mode with an electron energy of 70 eV and an emission current of 50 mA. Compounds were identified by first comparing their mass spectra with those contained in the HP

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Wiley 138 Mass Spectral Database and then comparing the LRI values with either those of authentic standards or with published values. Approximate quantities of the volatiles were estimated by comparing their peak areas with those of the 1,2-dichlorobenzene internal standard, obtained from the total ion chromatograms, using a response factor of 1.

2.3 Statistical analysis

Comparison between batches was performed by the t-test using Statgraph- ics Plus 5.0 for Windows. Significance level was established at P < 0.05.

3 – RESULTS AND DISCUSSION

The pH and chemical composition of both Italian and Brazilian Milano salamis (table 1) did not show significant differences (P > 0.05). Data are within the values recorded for this type of products and are close to those described by NOVELLI et al. (1998), MEYNIER et al. (1999) and ZANARDI et al. (2000). All Milano salamis studied were in the standards of the country where they were manufactured [the Norma Italiana Salame Italiano (UNI, 1996) and the Regulamento Téc- nico de Identidade e Qualidade do Salame tipo Milano (MAA, 2000)]. The Italian Milano salamis showed a mean water content of 35.5% slightly higher than the value allowed (water < 35%) by the Brazilian Regulamento (MAA, 2000).

Table 1

Chemical composition (g/100 g salami), pH, water activity (a_w) and TBARs* number of Milano salamis from Italy and Brazil.

The TBARs values are shown in table 1. The Milano salami from Italy showed a significantly higher (P < 0.05) value than samples from Brazil. How- ever, both values are lower than those described by NOVELLI et al. (1998) in experimental and commercial salami and close to those mentioned by MEYNIER

et al. (1999) and ZANARDI et al. (2000) in Milano salami.

The fatty acid profile (mean and standard deviation) of both Milano salamis is shown in table 2. Values are very similar among country origin products and only significant differences (P < 0.05) were found for the fatty acids C17:0, C18:0, C18:1(n−9) and C18:3(n−3). The difference in C18:3(n−3) content is of interest because implies differences in the total PUFA n−3 and in the PUFA n−6/n−3 ratio.

Salami Water Protein Fat Ash pH a_w TBARs

Italy 35.5 ±1.8 27.8 ±1.2 30.1 ±1.6 5.1 ±0.2 5.5 ±0.2 0.85 ±0.01 0.23 ±0.01a Brazil 33.1 ±2.1 28.7 ±1.4 32.0 ±2.2 4.9 ±0.2 5.3 ±0.3 0.87± 0.01 0.12 ±0.01b

*TBARs number: mg malondialdehyde/kg salami.

a,b: values in a column with different letter are significantly different (P < 0.05).

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Table 2

Fatty acid composition (% total methyl esters) of Milano salami from Italy and Brazil.

The highest PUFA n−6/n−3 ratio (19.5) was found in the Milano salamis from Brazil while samples from Italy showed a ratio of 10.4, this last value is similar to that reported by MORETTI et al. (2004) in commercial Italian salami. The ratio obtained in both Milano salamis is above the levels recommended by different authors and institutions, such as SIMOPOULOS (2002) (PUFA n−6/n−3 < 4), the British Nutrition Foundation (1992) (PUFA n−6/n−3 < 6) and the Sociedad Española de Nutrición Comunitaria (ROS, 2001) (PUFA n−6/n−3 6-10). The differences observed in the content of C18:3(n−3) and also in the PUFA n−6/n−3 ratio should be attributed to the pig diet fatty acid composition which influences the lard and pork (main ingredients of salami) fatty acid composition (GIRARD et al., 1988). Diets enriched in n−3 fatty acids give rise to an increase in the PUFA n−3 content and a decrease in the PUFA n−6/n−3 ratio in both lard and pork (D’ARRIGO et al., 2002 ; HOZ et al., 2003). The Milano salamis from Brazil showed lower levels of C18:3(n−3) probably because in this country a high content of maize is used in pig diet (SOARES et al., 2004). Maize is a component which PUFA n−6/n−3 ratio is higher if compared to other cereals also used in pig production as barley, wheat, etc. (HOSENEY, 1994).

Italy Brazil

Fatty acid Mean

(%) S.D.^a Mean

(%) S.D.^a P <^b

C12:0 0.1 – 0.1 – –

C14:0 1.3 0.19 1.5 0.1 –

C16:0 26.9 0.9 25.1 1.01 –

C16:1(n-7) 2.2 0.14 2.4 0.16 –

C17:0 0.3 0.12 0.4 0.08 0.01

C17:1 0.2 0.05 0.3 0.08 –

C18:0 14.0 0.87 11.9 0.82 0.05

C18:1(n-9)t 0.2 0.08 0.3 0.12 –

C18:1(n-9) 42.8 0.95 45.1 1.15 0.05

C18:2(n-6) 9.7 2.18 10.9 1.72 –

C18:3(n-3) 1.0 0.05 0.6 0.04 0.05

C20:0 0.2 0.01 0.3 0.04 –

C20:1(n-9) 0.4 0.34 0.5 0.29 –

C20:3(n-6) 0.5 0.08 0.5 0.07 –

C20:4(n-6) 0.2 0.1 0.3 0.13 –

Total SFA 42.8 1.71 39.3 1.8 –

Total MUFA 45.8 1.26 48.6 1.57 –

Total PUFA 11.4 2.26 12.3 1.77 –

Total n-6 10.4 1.62 11.7 1.76 –

Total n-3 1.0 0.19 0.6 0.09 0.05

n-6/n-3 10.4 1.71 19.5 2.05 0.05

a S.D.: standard deviation.

bP <: level of significance.

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About 95 volatile compounds were detected and 84 identified in the headspace of both Brazilian and Italian salamis. Table 1 shows the mean quantities of the identified compounds grouped according to their chemical class. They included 15 aldehydes, 13 alcohols, 13 hydrocarbons, 11 ketones, 10 esters, 10 terpenes, 7 acids, 4 sulphur compounds and 1 furan. The number of volatiles is high when compared with those obtained by other authors in similar products:

62 compounds identified by EDWARDS et al. (1999), 50 by PROCIDA et al. (1999) and 68 by SUNESEN et al. (2001). However, the volatile number was similar to that identified by MEYNIER et al. (1999) and MARCO et al. (2004). The Milano salamis manufactured in Brazil showed significantly higher concentrations (P < 0.05) in total volatile compounds and also in the following chemical groups: alcohols, hydrocarbons, esters, terpenes, ketones and acids. On the contrary, lower concentrations (P < 0.05) of aldehydes were found in the Brazilian Milano salami.

The origin of the volatile compounds of both salami groups was: carbohydrate fermentation (40% Brazil and 30% Italy), lipid oxidation (12% Brazil and 31% Italy), microbial esterification (11% Brazil and 3% Italy), spices and condiments (13% Brazil and 8% Italy), amino acid catabolism (14% Brazil and 20%

Italy) and miscellaneous (10% Brazil and 6% Italy). Figure 1 shows the total volatile compounds grouped by their origin. Only the lipid oxidation group was significantly higher (P < 0.05) in the Italian salami, being the remainder groups higher (P < 0.05) in the Brazilian product. This fact is mainly due to their higher level of lineal saturated and unsaturated aldehydes (C5 to C12) and is in total agreement with the high TBARs value (table 1) found in Italian salami. The lower lipid oxidation of the Brazilian salami could be related to the higher concentration of volatile from spices and condiments. Many of these spices show antioxidant properties (PALIC et al., 1993 ; LINDBERG and BERTELSEN, 1995). The higher level of volatiles from spices (mainly terpenes) detected in Brazilian salamis (fig. 1 and table 3) could be due to a higher amount of these ingredients in the formulation and/or to the use of fresher spices.

Volatile compouds origin

Volatile concentration (ng/100 g)

0 500 1 000 1 500 2 000

F LO ME S AC MI

a a

b a b a

b b

a

b a b

Figure 1

Volatile compound origin and concentration (ng/100 g) of Milano salami manufactured in Brazil (■) and Italy (). F: fermentation; LO: lipid oxidation; ME: microbial esterification;

S: spices and condiments; AC: amino acid catabolism; MI: miscellaneous.

a,b: columns with different letter differ significantly (P<0.05).

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Table 3

Volatile compounds (ng/100g) identified in Milano salami from Brazil and Italy.

LRI¹ Compound Origin² Mean concentration (ng/100g) Method of identification³

Brazil Italy

Alcohols 682a 424b

503 ethanol F 487a 290b ms + lri

524 2-propanol MI 19 6 MS + LRI

560 1-propanol LO 37 39 MS + LRI

653 1-butanol LO 2b 6a MS + LRI

705 2-pentanol LO 6b 40b MS + LRI

740 3-methyl-1-butanol AC 65a 7b MS + LRI

744 2-methyl-1-butanol AC 7 6 MS + LRI

784 2,3-butanediol F 27a 4b ms + lri

862 1-hexanol LO 3 5 MS + LRI

919 2-butoxyethanol LO 6 8 ms + lri

992 phenol MI 3 4 MS + LRI

1075 1-octanol LO 2b 5a MS + LRI

1091 2-methoxyphenol (guaicol) S 18a 4b ms

Aldehydes 312b 434a

654 3-methylbutanal AC 18a 5b MS + LRI

705 pentanal LO 25b 35a MS + LRI

802 hexanal LO 47b 93a MS + LRI

902 heptanal LO 21b 30a MS + LRI

961 (E)-2-heptenal LO 21 23 MS + LRI

972 benzaldehyde AC 90a 37b MS + LRI

1005 octanal LO 9b 28a MS + LRI

1063 (E)-2-octenal LO 20 19 MS + LRI

1065 benzeneacetaldehyde AC 14b 47a MS + LRI

1105 nonanal LO 12b 33a MS + LRI

1165 (E)-2-nonenal LO 5b 27a MS + LRI

1217 decanal LO 3b 8a MS + LRI

1268 (E)-2-decenal LO 12b 34a MS + LRI

1327 (E,E)-2,4-decadienal LO 9 7 MS + LRI

1414 dodecanal LO 6 8 MS + LRI

Hydrocarbons 296a 176b

663 benzene MI 100a 30b MS + LRI

600 hexane LO 6 8 MS + LRI

700 heptane LO 12 13 MS + LRI

769 methylbenzene (toluene) MI 33 27 MS + LRI

800 octane LO 39a 17b MS + LRI

864 ethylbenzene MI 6 7 MS + LRI

865 a dimethylbenzene MI 17a 9b ms

893 vinylbenzene (styrene) MI 2 5 MS + LRI

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900 nonane LO 32 37 MS + LRI

1000 decane LO 7 6 MS + LRI

1100 undecane LO 14a 4b MS + LRI

1200 dodecane LO 15a 5b MS + LRI

1300 tridecane LO 13a 8b MS + LRI

Furans 70b 130a

994 2-pentyl furan LO 70b 130a MS + LRI

Ketones 871a 366b

2-propanone MI 29a 3b ms

666 1-hydroxy-2-propanone F 31a 3b ms + lri

587 2,3-butanedione (diacetyl) F 389a 115b ms + lri

604 2-butanone F 216a 66b MS + LRI

683 2-pentanone LO 62 60 MS + LRI

711 3-hydroxy-2-butanone (acetoin) F 80 57 MS + LRI

915 2-methyl-2-cyclopenten-1-one MI 6 5 ms

898 2-heptanone LO 21 19 MS + LRI

980 2,3-octanedione LO 10 12 ms + lri

990 2-methyl-3-octanone MI 22a 6b ms

1099 2-nonanone LO 5b 20a MS + LRI

Esters 494a 87b

531 methyl acetate ME 45a 5b ms

615 ethyl acetate ME 260a 40b MS + LRI

709 ethyl propanoate ME 12 10 MS + LRI

716 propyl acetate ME 12a 3b MS + LRI

724 methyl butanoate ME 11a 4b ms + lri

805 ethyl butanoate ME 39a 7b MS + LRI

756 ethyl-2-methyl propanoate ME 15a 3b ms + lri

849 3-methylethyl butanoate ME 72a 9b MS + LRI

997 ethyl hexanoate ME 21a 4b MS + LRI

1290 ethyl decanoate ME 7a 2b MS + LRI

Acids 975a 358b

649 acetic acid F 480a 255b MS + LRI

736 propanoic acid MI 12 13 MS + LRI

818 butanoic acid F 173a 25b MS + LRI

857 3-methyl butanoic acid AC 44a 8b ms + lri

868 2-methyl butanoic acid AC 61a 11b ms + lri

906 pentanoic acid MI 98a 13b MS + LRI

1005 hexanoic acid MI 107a 33b MS + LRI

Terpenes 551a 136b

924 α-thujene S 14a 3b ms + lri

934 α-pinene S 2b 7a ms + lri

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Volatiles from carbohydrate fermentation and microbial esterification, both showing higher (P < 0.05) amount in Brazilian salamis, are probably related.

Thus, ethanol and acetic acid are the most abundant compound from fermentation yielding their addition the 51 and 72% of the Brazilian and Italian fermentation volatiles, respectively. Besides the main ester was the ethyl acetate, which reached a 53 and 46% of the total esters in Brazil and Italy products, respectively. This compound is generated from the esterification of ethanol and acetic acid by microbial esterases (STAHNKE, 1995). Brazilian samples showed about 1.7-fold higher concentration of ethanol and acetic acid than the Italian ones.

This ratio was even higher (6.5-fold) for the ethyl acetate originated from them.

The study of volatile compounds of dry fermented sausages manufactured without spices done by MARCO et al. (2004) using SPME with Carboxen/PDMS phase, also showed high quantities of acetic acid (22%), ethanol (17%) and ethyl acetate (8%). However, these high levels differed from the volatile components isolated in Milano salami by MEYNIER et al. (1999) using a Tenax trap, who did not find either of those compounds. These differences are probably due to the method of volatile extraction. Tenax has a low affinity for low-boiling compounds, which break through the Tenax without been retained; on the other hand, Carboxen/PDMS fibre is adapted for the extraction of low molecular weight compounds (PILLONEL et al., 2002). Therefore, and as REINECCIUS (1993) previously stated, none of the available volatile extraction techniques produces a completely accurate representation of the volatile profile of food products.

Thus, it is necessary to carefully select the extraction technique, depending on the objective of the study. Despite SPME is becoming the preferred technique

973 sabinene S 182a 11b ms + lri

979 β-pinene S 76a 17b ms + lri

989 myrcene S 27 34 ms + lri

1006 α-phellandrene S 7 8 ms + lri

1014 δ-3-carene S 15 24 ms + lri

1034 β-phellandrene S 28a 3b ms + lri

1031 limonene S 196a 27b MS + LRI

1100 linalool S 4 2 ms + lri

Sulphur compounds 422 457

538 carbon disulfide AC 366 385 MS + LRI

712 3-methylthio-1-propene S 35b 58a ms + lri

924 methyl-2-propenyl disulfide S 5 3 ms + lri

1087 di-2-propenyl disulfide S 16 11 ms + lri

Total volatiles 4673a 2568b

1. Linear retention index on a CP-Sil 8 CB low bleed/MS column.

2. Origin: F (carbohydrate fermentation); LO (lipid oxidation); AC (amino acid catabolism); ME (microbial esterification); S (spices and condiments); MI (miscellaneous: contaminants, unknown, etc.).

3. MS + LRI, mass spectrum and LRI agree with those of authentic compounds; ms + lri, mass spectrum and LRI in agreement with the literature; ms, mass spectrum agrees with spectrum in the HP Wiley 138 Mass Spectral Database.

a,b: values in the same row with different letters are significantly different (P < 0.05).

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because it offers a great variety of coatings which can also be combined and is rapid, not expensive and easy to use.

4 – CONCLUSIONS

Results clearly indicate that Milano salami manufactured in Brazil and Italy mainly differs in the C18:3(n−3) content, PUFA n−6/n−3 ratio and volatile composition. Salami produced in Brazil showed more compounds from fermentation, microbial esterification, spices and amino acid catabolism.

5 – ACKNOWLEDGEMENTS

R. M. L. de Campos is beneficiary of a predoctoral grant from the Brazilian Government (CAPES).

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