Meat Processing 010-Flavor Fish PDF
Meat Processing 010-Flavor Fish PDF
Meat Processing 010-Flavor Fish PDF
7.1 Introduction
The flavour of fish is composed of taste which is comprised of nonvolatile
taste-active compounds and odour comprised of volatile compounds. The
nonvolatile taste-active compounds are low-molecular-weight extractive
components. These compounds are more abundant in the tissues of molluscs and crustaceans than fish which explains why shellfish are considered
to be more tasty than finfish. The extractive or nonvolatile taste-active compounds may be divided into two broad groups: nitrogenous compounds,
including free amino acids, low-molecular-weight peptides, nucleotides and
related compounds, and organic bases; and non-nitrogenous compounds,
including organic acids, sugars and inorganic constituents.
The aromas associated with very fresh fish are usually mild, delicate
and pleasant (Lindsay, 1990). These aromas are generally described as
green, plant-like or melon-like and are provided by various carbonyls
and alcohols (Josephson and Lindsay, 1986) along with iodine-like odours
in marine fish which are contributed by bromophenols (Boyle et al,
1992). Some species such as salmon have very characteristic fresh odours
(Josephson et al., 199Ib).
However, the aromas of fish are very perishable and the study of offodours is therefore important. In the process of deterioration, the very
fresh fish odours may be destroyed by microbial and autolytic activity or
new compounds produced may mask the very fresh fish aromas. Processing
can also have a dramatic impact on the aroma of fish. Besides deterioration, environmental factors can impart off-flavours to fish.
The aroma of very fresh fish may vary considerably among species but most
fish have a common sweet and plant-like aroma that is easily recognized and
associated with fresh fish. This fresh fish flavour is due to volatile carbonyls
and alcohols which are derived from the polyunsaturated fatty acids of fish
lipids via specific lipoxygenase activity (Josephson and Lindsay, 1986).
Carbonyls
c d
l-Penten-3-ol (Z)-3-Hexen-l-olc
l-Octen-S-ol3^
(E)-Z-OCtCn-I-Ol^
l,5-Octadien-3-ola-d
2,5-Octadien-l-ola-d
(E)-2-Nonen-l-olb
(Z)-6-Nonen-l-olb-c
(Z)-3-Nonen-l-olb
(E,Z)-2,6-Nonadien-l-olb
3,6-Nonadien-l-olbc
a
b
c
(E)-2-Penten-l-ald
Hexan-l-al cd
(E)-2-Hexen-l-alc
(E^-Octen-l-al3-0
(E)-2-Nonen-l-ala-c
(E,Z)-2,6-Nonadien-l-ala-d
l-Octen-3-onec'd
2,3-Octadien-l-onec
1 ,5-Octadien-3-onec-d
COOH
Eicosapentaenoic Acid
15-Lipoxygenase
12-Lipoxygenase
COOH
0OH
COOH
0OH
Lyase
Lyase
OH
CHO
CHO
(Z,Z)3,6-NonadienaJ
(Z)S-Hexenal
Lyase
Lyase
CHO
OH
(Z)1,5-Octadien-3-ol
O
(Z)1,5-Octadien-3-one
(E)2,6-Nonadienal
(Z,Z)3,6-Nonadien-1-ol
CHO
OH
1-Penten-3-ol
(E)2-Hexenal
(Z)3-Hexen-1-ol
Figure 7.1 Proposed mechanism for enzymatic biogeneration of volatile carbonyls and
alcohols important to freshly harvested fish aroma from eicospentaenoic acid (adapted from
Josephson and Lindsay, 1986).
Table 7.2 Some volatile aroma compounds and their associated aroma
quality
Compound
Description
Hexan-1-al
(E)-2-Nonen-l-al
(E,Z)-2,6-Nonadien-l-al
(E,Z)-3,6-Nonadien-l-al
l-Octen-3-ol
(Z)-2-Octen-l-ol
(Z)-l,5-Octadien-3-ol
(E,Z)-2,5-Octadien-l-ol
l-Octen-3-one
(Z)-1, 5-Octadien-3-one
Green, aldehyde3
Cucumber, cardboard3 c
Cucumber peela-c
Cucumber, melon rinda-c
Mushroom3
Fatty, rancid5
Earthy, mushroom3
Earthy, mushroom3
Mushroom3
Geranium leaves3
a mushroom and geranium-like aroma. Table 7.2 lists some of the volatile
aroma compounds of fresh fish and associated description of individual
compounds.
The substrates for the production of the volatile carbonyls and alcohols
are the polyunsaturated fatty acids. The lipoxygenase found in fish exhibits
the same selectivity towards arachidonic, eicosapentaenoic and docosahexaenoic acids but shows negligible response to linoleic and linolenic
acids (Zhang et al, 1992b; Hsieh et al, 1988, 1992c). However, lipoxygenases in plants have specificity for linoleic and linolenic acids (Minamide,
1977; Sessa, 1979; MacLeod and Pikk, 1979).
The specific volatile compounds generated by the lipoxygenase are
dependent on the substrate (Zhang etal, 1992b; Hsieh and Kinsella, 1989).
For example, if eicosapentaenoic acid or docosahexaenoic acid is the
substrate, the compounds l,5-octadien-3-ol, (E,Z)-2,6-nonadienal, 2,5octadien-1-ol and 3,6-nonadien-l-ol are the flavour volatiles generated.
However, from arachidonic acid, (E)-2-octenal, l-octen-3-ol, (E)-2-nonenal, (E)-2-octenol and (Z)-3-nonenol are produced (Zhang et al, 1992b).
7.2.2 Sulphur compounds
Volatile sulphur compounds are usually associated with deteriorated
seafood. However, there is evidence that sulphur compounds can be
produced in fish (Josephson et al, 1986b) and may contribute to aromas
that characterize the odours of some fresh seafoods. Dimethyl sulphide is
one of the volatile sulphur compounds known to provide a pleasant
seashore-like smell in fresh seafoods (Iida, 1988). When dimethyl sulphide
is in low concentration (<100ppb), it gives a pleasant crab-like aroma;
however, at higher concentrations, it is perceived as having an offensive
odour (Iida, 1988). The formation of methyl mercaptan, dimethyl disulphide and dimethyl sulphide in the flathead (Calliurichthys doryssus} at
the time of harvest has been reported (Shiomi et al, 1982).
The proposed pathways provided are different from those given by
Josephson et al (1984a,b,c) but are consistent with the current data. Further evidence for the proposed pathway is provided by the identification of
a 12-lipoxygenase in the skin and gill tissue of trout which can oxidize
polyunsaturated fatty acids into position specific hydroperoxides (Hsieh
and Kinsella, 1989; German et al, 1986; German and Kinsella, 1985).
Lipoxygenase-like activity has also been found in crude extracts from skin
and gill of wild and cultured ayu (Zhang et al, 1992a, b) and smelt (Zhang
etal, 1992c). The hydroperoxides are decomposed to produce various fragmentation products such as the volatile carbonyls and alcohols which
contribute to the aroma of freshly harvested fish (Hsieh et al, 1988).
As shown in Figure 7.1, the 12-lipoxygenase produces hydroperoxides
that fragment into the eight- and nine-carbon volatile carbonyls and alcohols. According to the pathways proposed, a 15-lipoxygenase is required
for the biogenesis of the five- and six-carbon volatile carbonyls and alcohols (Josephson and Lindsay, 1986). The existence of a 15-lipoxygenase
in trout gill was confirmed by German et al (1992)
The 12- and 15-lipoxygenases are not distributed equally amongst fish
species (German et al, 1992). For example, trout exhibit very high 12- and
virtually undetectable 15-lipoxygenase activities, whereas in carp, although
the 12-lipoxygenase is most active, the 15-lipoxygenase is also relatively
abundant. In sturgeon, the 15-lipoxygenase is actually the predominant
enzyme (German et al, 1992). The existing differences in concentration of
different lipoxygenases might account for some of the observed variations
in the flavour spectrum of different species.
7.2.3
Bromophenols
2-BP
Species
Pink salmon
Sockeye salmon
Chinook salmon
Coho salmon
US pickled herring
European brine-cured herring
Icelandic haddock
3-/4-BP
1.4
1.6
2,4-DBP
0.8
1.0
1.6
38.0
2.2
2.7
2,4,6-TBP
32.1
7.4
33.2
5.1
3.7
13.5
4.5
Source: Adapted from Boyle et al (1992); symbols are BP, bromophenol; DBP, dibromophenol; and TBP, tribromophenol.
(Boyle et al, 1992). Several authors have suggested that this loss of flavour
is due to the cessation of feeding and mobilization of muscle lipids and
carotenoid pigments into the gonads and skin (Josephson et al., 1991a,b;
Kitahara, 1984; Hatano et al, 1983; Ota and Yamada, 1974). However,
Boyle et al (1992) found that bromophenols were virtually absent from
sexually mature freshwater salmon lacking brine- or sea-like flavours and
concluded that the bromophenols were depurated from the saltwater
salmon upon cessation of feeding. Bromophenols are virtually absent in
freshwater fish (Boyle et al, 1992).
7.2.4 Hydrocarbons
The hydrocarbons (E9Z)- and (EJE)-1,3,5-octatriene have been found in
spawning condition salmon and other non-salmonid freshwater fish
(Josephson, 1991). The contribution of these unsaturated hydrocarbons to
seafood flavour has not been studied, but may be significant because 1,3octadiene exhibits a mushroom, humus-like aroma (Persson and Juttner,
1983).
7.3 Species-specific characteristic aromas
7.3.7
Canned tuna
Some fish species have distinct characteristic aromas. Canned tuna has an
aroma different from other canned fish and is often described as meaty.
One of the compounds identified in canned tuna that has an intense beef
extract aroma is 2-methyl-3-furanthiol (Withycombe and Mussinan, 1988).
2-Methyl-3-furanthiol along with other similar compounds produces the
rich meaty flavour of canned tuna (Withycombe and Mussinan, 1988).
7.3.2
Salmon
Figure 7.2 Alkyl furanoid-type structure of salmon loaf-like aroma compound (adapted
from Josephson et al., 199Ib).
(Dougan and Howard, 1975). The meaty aroma is complex and varies with
the origin of the sauce (Beddows et al, 1976). Dougan and Howard (1975)
identified acetic, propionic, n-butyric and isobutyric, and isovaleric acids as
specific volatile acids contributing to the aroma of fermented fish sauce
with acetic and n-butyric acids being the two major components. Sanceda
et al (1983) reported that propionic and n-butyric acids were the major
acids and identified additional volatile acids with two to ten carbon atoms,
both n-acids and iso-acids. Sanceda et al. (1983) concluded that the volatile
acids appear to be responsible for the cheesy aroma and rancid odour of
fermented fish sauce. Mclver et al. (1982) reported that the neutral fraction
of a fish sauce extract which possessed a meaty aroma contained three
lactones as the main components along with alcohols, heterocyclic compounds and benzaldehyde.
Fish enzymes, microorganisms and fat oxidation have all been considered as possible contributors to the development of fermented fish sauce
aroma (Beddows et al., 1976). In a study on the use of enzymes on the
hydrolysis of mackerel and the investigation of fermented fish aroma,
Beddows et al. (1976) concluded that bacteria play an important role in
the development of the cheesy aroma of fermented fish sauce obtained
from mackerel.
Anchovies are usually eaten salted and cured (ripened). The maturing or
ripening process is thought to have a significant impact on the final product.
As anchovies ripen, their contents of 2,4-heptadienal and (E,Z)-3,5-octadien-2-one increase (Triqui and Reineccius, 1995a). The anchovy flavour is
due to both the enzymatically generated C8 alcohols and ketones along with
(E,Z)-2,6-nonadienal, which contribute plant- and cucumber-like aromas,
and autoxidatively derived C7-C10 conjugated aldehydes, which impart fatty
and fried fat-like aromas to products (Triqui and Reineccius, 1995b). More
recently, Cha et al. (1997) reported 98 volatile compounds in salt-fermented
anchovy with l-octen-3-one, (Z)-4-heptenal, (E,Z)-2,6-nonadienal, 3methylbutanal, 3-(methylthio)propanal, ethyl 2-methylbutanoate and ethyl
3-methylbutanoate being the most potent odorants.
7.4.6
Cooking
Compounds causing off-flavours in fish and their control have been extensively reviewed (Obata et al., 1950; Wyatt and Day, 1963; Meijboom and
Stroink, 1972; McGiIl et al., 1974; Ke et al., 1975; Kikuchi et al., 1976; Reineccius, 1979; Ross and Love, 1979; Josephson et al., 1983b; Hsieh et al, 1989;
Kasahra et al., 1989, 1990; Kawai, 1990; Haard, 1992). These compounds
may arise from the environment or through deterioration. Environmentally derived odour compounds will be discussed in a later section.
7.5.7
precedes that of TMA (Amano and Yamada, 1964) and in frozen gadoids
that are kept at high subfreezing temperatures, DMA and formaldehyde
are produced enzymatically, but TMA formation is prevented due to inhibition of microbial growth (Castell et al., 1973).
Many studies have positively correlated levels of TMA and sensory
scores of unfrozen marine fish (Dussault, 1957; Spencer, 1962; Farber,
1965; Magno-Orejana et al, 1971; Sen Gupta et al, 1972) and thus TMA
is often used as a spoilage index for unfrozen fish. However, production
of DMA may serve as a better measure of deterioration in frozen gadoids
(Castell et al., 1970).
7.5.2 A utoxidation
Autoxidizing fish lipids have long been linked to the production of fishy
flavours in both chill-stored and frozen fish. Similar compounds are formed
in fish and fish oil as a result of autoxidation of polyunsaturated fatty
acids (Josephson et al., 1984c, 1986b; Karahadian and Lindsay, 1989a,b).
The oxidized aromas in autoxidized fish oils vary from just perceptible
to extremely unpleasant fish oil-like odours. Initially, aromas described as
green or cucumber-like (Karahadian and Lindsay, 1989a) arise, but as
oxidation progresses odours described as fishy, cod liver oil-like, or burnt
are developed (Lindsay, 1990).
The initial aromas are due to the production of short-chain saturated
and unsaturated aldehydes and include hexanal and (E)-2-hexenal. The
most important contributors to the fishy and cod liver oil-like aromas are
(E,Z,Z)-2,4,7-decatrienal and (E,E,Z)-2,4,7-decatrienal (Meijboom and
Stroink, 1972: Karahadian and Lindsay, 1989a). Ke et al. (1975) reported
the presence of 2,4,7-decatrienals in autoxidized mackerel oil.
The 2,4,7-decatrienals are derived from autoxidation of long-chain
polyunsaturated co-3 fatty acids which are abundant in fish lipids. The
compound 2,4,7-decatrienal and other aldehydes are produced via p-scission of alkoxy radicals generated by the homolytic cleavage of each isomer
of the hydroperoxides (Fujimoto, 1989) (Figure 7.3).
It is proposed that the H-donating character of tocopherol-type
compounds causes a preferential formation of cis-trans rather than transtrans monohydroperoxide that provides the direct precursors of the
2,4,7-decatrienals. A stepwise mechanism for the formation of transjranshydroperoxide compared to trans,cis-hydroperoxide is provided in
Figure 7.4.
7.5.3
(Z)-4-Heptenal
Deteriorated aromas that develop in cod and related species have also
been associated with the compound (Z)-4-heptenal (McGiIl et al., 1974,
2,4-Heptadienal
3,6,9,12-Pentadecatetraenal
Propanal
3-Hexenal
3,6,9-Dodecatrienal
2,4,7-Decatrienal
Figure 7.3 Formation of 2,4,7-decatrienal and other aldehydes from autoxidation of docosa
hexaenoic acid.
Eicosapentaenoic acid
Tocopherol
(E,Z)-hydroperoxide
No tocopherol
rotation (step 1)
translocation (step 2)
(E,Z,Z)-2,4,7-decatrienal
(E,E)-hydroperoxide
(E,E,Z)-2,4,7- decatrienal
1977; Hardy et al, 1979). This compound does not contribute distinct fishytype flavours but rather it potentiates the stale, burnt/fishy, cod liver
oil-like flavour contributed by the 2,4,7-decatrienals (Karahadian and
Lindsay, 1989a). At low concentrations in water (Z)-4-heptenal exhibits
a cardboardy character while at higher concentration the aroma is more
putty-, paint- or linseed oil-like (Lindsay, 1990). The aroma of (Z)-4heptenal has also been described as cold boiled potato-like and is believed
to be responsible for much of the aroma of boiling potatoes (Josephson
and Lindsay, 1987a).
(Z)-4-Heptenal is produced by the water-mediated retro-aldol condensation of (E,Z)-2,6-nonadienal and the proposed mechanism is shown in
Figure 7.5 (Josephson and Lindsay, 1987b).
The production of (Z)-4-heptenal is accelerated with increased temperatures and at high pH (Josephson and Lindsay, 1987b) and is therefore
commonly found in cooked, stored seafoods (McGiIl et al, 1974, 1977).
7.5.4
Volatile acids
During the storage of fish, various volatile acids are formed. Kikuchi
et al. (1976) have reported that formic, acetic, propionic, n- and isobutyric,
and n- and isovaleric acids are formed in fish flesh during storage. A study
Transition Reaction
Cascade
Acidic Medium
Reservoir
(E.Z)-nonadienal
Hydration
Reactions
gem-diol
hydroxy-enolate
hydroxy-enol
3-hydroxy-(Z)-6-nonenal
hydroxy gem-diol
Retrol-aldol
Condensation
(Z)-4-heptenal
ethanal
Figure 7.5 Proposed mechanism for the formation of (Z)-4-heptenal from (E,Z)-2,6-nonadienal via alpha/beta double bond hydration and retro-aldol condensation (adapted from
Josephson and Lindsay, 1987b).
on oxidized sardine oil found that propionic acid followed by acetic acid
were dominant (Table 7.4).
Although the concentrations of butyric and valeric acid are much lower,
their lower odour thresholds make them more important than other acids
(Kikuchi et al, 1976). The short-chain volatile acids give very intense and
objectionable sweaty odours and are considered important markers for
flavour quality of fish oil (Hsieh et al., 1989). However, Karahadian and
Lindsay (1989b) concluded that short-chain fatty acids found in oxidizing
fish were of insignificant concentrations to contribute characterizing burnt/
fishy flavours and aromas.
7.5.5
Other compounds
Acetic acid
Propionic acid
n-Butyric acid
Isobutyric acid
n- Valeric acid
Isovaleric acid
n-Caproic acid
Isocaproic acid
a
Content
(ppm)a
Odour threshold
(ppm)b
959
1270
17.4
8.4
13.5
13.3
500
54.5
34.2
32.8
3
9.2
1.1
1.7
7.5
Scheme 7.1
Efforts have also been made to improve sardine odour by adding soy
sauce flavouring or Mirin flavourings (Kasahara et al., 1989, 1990) and the
suppression of the odour of roasted sardine has been achieved using lemon
juice (Kasahara and Nishibori, 1992).
Muddy
off-flavours
Figure 7.6 Chemical structure of geosmin (A) and 2-methylisoborneol (B) (adapted from
Schrader and Blevins, 1993).
(Persson, 1979), trout (Yurkowski and Tabachek, 1974) and shrimp (Lovell
and Broce, 1985) and various wild commercial species such as walleye,
northern pike, cisco and lake whitefish (Yurkowski and Tabachek, 1980)
have also been tainted with these earthy or musty off-flavour compounds.
7.6.2
'Blackberry'
off-flavour
The free amino acid content of fish is relatively low when compared to
shellfish. However, some authors have reported that certain free amino
acids can occur in fish muscle at high enough concentrations to contribute
to fish flavour, independent of other constituents. There are reports that
glycine contributes to the sweetness of fish (Amano and Bito, 1951) and
histidine contributes to the 'meaty' character of some seafoods (Simidu
et al., 1953). Others argue that the individual free amino acids in fish such
as gadoids are at levels below their flavour thresholds and are therefore
unlikely to be important contributors to flavour.
The most notable feature of free amino acid contents in fish is the high
content of histidine in makerel and tuna and a high taurine content in
white-fleshed fish (Konosu and Yamaguchi, 1982). A study of wild and
cultured red sea bream reported that wild fish had a higher content of
many of the free amino acids, except for histidine, than their cultured
counterparts (Morishata et al., 1989). However, other studies on the
extractive components of wild and cultured fish, including red sea bream
(Konosu and Watanabe, 1976), yellowtail (Endo et al., 1974) and ayu
Table 7.5 Distribution (%) of non-protein nitrogen compounds in a
teleost (mackerel) and elasmobranch (shark)
Class of compounds
Mackerel
Shark
25
5
10
35
15
5
5
5
10
20
55
10
(A)
(B)
IMP
Phosphatase
AMP
Deaminase
ATP
ADP
AMP
Inosine
IMP
AMP
Phosphatase
Hypoxanthine
Ribose
Adenosine
Deaminase
Adenosine
Figure 7.8 The postmortem enzymatic degradation of ATP (adapted from Komata, 1990),
where ATP = adenosine triphosphate; ADP = adenosine diphosphate; AMP = adenosine
monophosphate; and IMP = inosine monophosphate.
Urea is present in small quantities in tissues of all fish. Marine elasmobranchs, however, contain relatively high amounts (1-2.5%) of urea for
osmoregulation (Haard et al, 1994). Urea has no flavour, but it is readily
decomposed to ammonia and carbon dioxide. Bacterial urease catalyses
this reaction and the pungent odour of the resulting ammonia may
contribute to unacceptable quality of fish (Finne, 1992).
Trimethylamine oxide, a quateranary ammonium compound, commonly
found in marine teleosts and elasmobranchs, has no odour or taste. However, the breakdown products of TMAO have very potent odours which
contribute to fish spoilage (see section 7.5).
(A)
(B)
Figure 7.9 Structures of creatine (A) and creatinine (B) (adapted from Konosu and
Yamaguchi, 1982).
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