FISHERIES AND MARINE SERVICE
Translation Series No. 3530
Odorous components of roasted fish meat
by Kayoko Kasahara, and Kokichi Nishibori
Original title: Gyoniku Shoshu Seibun--I
From: Nippon Suisan Gakkaishi 41: 43-49, 1975
Translated by the Translation Fureau(JG/PS) Multilingual Services Division Department of the Secretary of State of Canada
Department of the Environment Fisheries and Marine Service Halifax Laboratory Halifax, N.S.
1975
15 pages typescript ,71 )72
• (APARTMENT OF THE SECRETARY OF STATE SECRÉTARIAT D'ÉTAT TRANSLATION BUREAU BUREAU DES TRADUCTIONS
MULTILINGUAL SERVICES 'ere DIVISION DES SERVICES CANADA DIVISION MULTILINGUES
TRANSLATED FROM - TRADUCTION DE INTO - EN Japanese English
AUTHOR AUTEUR KASAHARA, Kayoko and NISHIBORI, Kokichi
TITLE IN ENGLISH - TITRE ANGLAIS
Odorous Components of Roasted Fish at
TITLE IN FOREIGN LANGUAGE (TRANSLITERATE FOREIGN CHARACTERS) TITRE EN LANGUE ÉTRANGÉRE (TRANSCRIRE EN CARACTèRES ROMAINS) Gyoniku Shoshu Seibun--I
REFERENCE IN FOREIGN LANGUAGE (NAME OF BOOK OR PUBLICATION) IN FULL. TRANSLITERATE , FOREIGN CHARACTERS. RÉFÉRENCE EN LANGUE ÉTRANGÉRE (NOM DU LIVRE OU PUBLICATION), AU COMPLET, RANSCRIRE EN CARACTèRES ROMAINS.
REFERENCE IN ENGLISH - RÉFÉRENCE EN ANGLAIS Bulletin of the Japanese Society of Scientific Fisheries
PUBLISHER - ÉDITEUR PAGE NUMBERS IN ORIGINAL DATE OF PUBLICATION NUMÉROS DES PAGES DANS DATE DE PUBLICATION L'ORIGINAL 43-49 YEAR ISSUE NO. VOLUME PLACE OF PUBLICATION ANNE NUMÉRO NUMBER OF TYPED PAGES LIEU DE PUBLICATION HOMBRE DE PAGES DACTYLOGRAPHIÉES 1975 41 1 15
REQUESTING DEPARTMENT Environment TRANSLATION BUREAU NO. 753371 MINISTÈRE- CLIENT NOTRE DOSSIER NCI
BRANCH OR DIVISION TRANSLATOR (INITIALS) Fisheries S3rvice- - J GAS DIRECTION OU DIVISION TRADUCTEUR (INITIALES)
PERSON REQUESTING Allan T. Reid • DEMANDE PAR SEP 1 2 1975
YOUR NUMBER VOTRE DOSSIER N 0 UNEDITED TRANSLATION DATE OF REQUEST DATE DE LA DEMANDE 25-06-75 For information only TIUDUCTION NON i'2.EVSE7i Informeition seviernznt
SOS•200.10.6 (REV. 2/08) 7530.21.029.5533 1/41-(21)
• e • DEPARTMENT OF THE SECRETARY OF STATE SECRÉTARIAT D'ÉTAT TRANSLATION BUREAU , BUREAU DES TRADUCTIONS
MULTILINGUAL SERVICES DIVISION DES SERVICES DIVISION CANADA MULTILINGUES
CLIENT'S NO. DEPARTMENT DIVISION/BRANCH CM NO DU CLIENT MINISTERE DIVISION/DIRECTION VILLE
Environment Fisherics Service Ottawa, Ont. BUREAU NO. LANGUAGE TRANSLATOR (INITIALS) NO DU BUREAU LANGUE TRADUCTEUR (INITIALES) .
SEP 121975 753371 Japanese JG/PS Bulletin of the Japanese Society of Scientific Fisheries Vol. 41, No. 1, 1975, pp. 43-49 (43 .0darous ' Components of Roasted Fish Meat -
By ..:.eLSAHARA, KayokOex2, NISHIBORI, Kokicht Received: September 12, 1974
One of the techniques employed in the traditional Japanese way of cooking is called "Teriyaki e3or "Kabayaki."*3 While fish meat broiled without any seasoning lacks flavour to stimulate our appetites, fish broiled with the
tf) so-called "Taré"--the seasoning for "Teriyaki" or
F.` 'e ca: 0 e4 E "Kabayaki"--is enhanced with a very appetizing flavour tfl c -5 zooø and lust.er; and its pleasant taste has been well liked by
0 .4-fn-- *1 Presented at the Spring General Meeting of the Japanese tà..1 L t-- ' Society of Scientific Fisheries (Tokyo) in 1971 & 1972. 1.. ID 11/42 Home 46.■ r Economics Dept., Notre Dame Seishin University, Okayama. E $3 Broiled fish or meat with seasoning sauce (Translator's note).
SOS...200-10 ■ 31 2
many Japanese. It is believed that the fragrance of "Teriyaki" or "Kabayaki" is produced in the following manner: protein, amino acids, amines, saccharoids, etc. of fish meat, fish skin and seasoning produce aldehydes and pyrazines as they turn brown as a result of several chem- ical reactions due to calcination --including the Merâclo* reaction. At the same time, sulfur-containing compounds as well as by-products formed by thermal decomposition based on fish lipids, contribute to the emanation of the flavour. 1) Obata et, al. obtained very realistic "Kabayaki" flavour by calcinating mixtures of sucrose, soy sauce, , palmitic acid and•piperidine in their model experiment. In practice, however, no study has so far been reported on the _isolation and identification of flavouring volatiles originating directly from fish "Teriyaki" or "Kabayaki". As a first step to isolate and identify the flavour.ing volatiles of fish "Teriyaki" or "Kabayaki", a panel test was conducted en the flavour of "Teriyaki" or "Kabayaki" and described in this report. This was followed by a comparison, in as natural a state as possible, with the whole flavour of "Teriyaki" or "Kabayaki" using four kinds of fish; chiefly employing the head space vapor gas chromatograms. Next, a comparison was made with the flavour of eels broiled without seasoning and that of "Kabayaki" eels. The ieD7L0-..tian and identification of "Kabayaki"
Aer.N.: meaning unknown; transliterated as such from the Japanese word Teichnmst be a Japanese rendition of a foreign term. flavour carbonyl components and alcohol components were then conducted.
Experimental method and its results
Samples
Only edible portions of fresh eel, conger eel, yellowtail and horse-mackerel were used. Seasoning for this experiment was a miX-
.ture of cojmrercial dark soy sauce and refined sugar (sucrose concentration 36%). Paneltest on the flavour of eel "KabaVaki"
The whole flavour of eel "Kabayaki", prepared by the mthod described later,.was passed through successive traps of 2% sodium bicarbonate, 2% hydrochloric acid, 0.2% 2,4-dinitro- phenylhydrazine 2N-hydrochloric acid solution, and 2% lead acetate by using the nitrogen gas draft method. As a result , it was (44 found that the carbonyl fraction and h^drogen sulfide were very
inportant in the flavour of eel "Kabayaki". Method of uroducirg and collecting the odorous conrnaonents of broiled fish 1. Method of preparing H.S.V. ( head space vapor) of the whole flavour of "Teriyaki" or "Kabayaki"s A10-g. sample
of fish meat was broiled for four minutes over medium heat
(city gas) using a commercially available fish broiler with
an asbestcs plate on one side (surface temperature of the
broiler 250°C). After that, the following operation was
repeated four timesc the meat was soaked in seasoning
sauce for one minute, and then broiled for one minute. The 4 sample thus broiled was immediately transferred into a
100 ml Erlermleyer flask; the meat was rapidly ground and the mouth of the flask was sealed with a piece of aluminum foil; it was heated for one and a half minutes on a metal mesh plate with asbestos on one side, placed on a preheated electric burner (600W). Its H.S.V., 0.5 to 1 ml, was then taken as sample for gas chromatographic analysis. 2. Preparation method of H.S.V. of the whole flavour of fish broiled without seasonings The sample of fish meat,
10 g, was broiled without seasoning under heating conditions similar to those described above. It was then transferred immediately to a 100 ml Erlenmeyer flask; heated for 1.5 minutes in a similar manner as before and its H.S.V., 0.6 to 1 ml, was taken as sample for gas chromatographic analysis.
3. Preparation method of H.S.V. of the whole flavour of roasted seasoning: Seasoning sauce, 0.025 ml, was placed in a 100 m1 Erienmeyer flask; then sealed with a piece of alumi- num foil. It was heated for one minute on an electric burner as before, and its H.S.V., 2 to 5 ml, was taken as sample for gas chromatographic analysis. Conditions for the gas chromatographic analysis
The apparatus used was a Shimazu GC-4APTF model (Rising temperature, FID). The analysis of the whole flavour compo- nent was done as follows:
Columns Stainless 3^ x 3 m
Retention phases 10% PEG 6000 (TPA, 30 to 60 mesh) and 5% silicon DC 550 (Shimalite W, 60 to 80 mesh) 5
Column temperature: 40 ÷ 160°C, 4 C/min. Sample room temperature: 250°C Detector temperature: 210°C Nitrogen gas pressure: 0.4 to 0.5 kg/cm2 Sensitivity: 103 x 0.4 V Attached gas sampler temperature and volume: About 100°C, 5 ml. An analysis of the whole flavour components, with 5% carbowax 20M as the retention phase, was also conducted at the same time. The analysis of the carbonyl and alcohol components was con- ducted as follows: Retention phase: 5% carbaaax 2014 (Diasolid L, 60 to 80 uesh) Nigrogen pressure: 0.75 kg/cm2 Sensitivity: 103 x 0.1 V Other conditions: Same as for the analysis of the whole flavour components. 4. Comparison of H.S.V., the whole flavour of four kinds of "Kabayaki" (45) fish: The H.S.V. of "Teriyaki" or "Kabayaki" in respect of four different types of fish, and obtained by the method described above, were analyzed by the gas chromatogram with retention phase PEG 6000 (UM) and silicone DC 550. As sham in Fig. 1 and 2, several component peaks appeared in all cases and aside from differences in peak strength, no much difference in gas chromatogram was noticed between the four kinds of fish. Comparison of H.S.V. for both eel kabayaki and plain roasting
Gas chr. omatographic analysis %ms performed and the whole flavor H.S.V. of eel kabayaki and of plain broiling by retention phase PEG 6000 (TPA) and by silicon DC 550. As shaan in Fig. 3 and 4, five peaks including a very sharp one were detected from the whole flavour of eel "Kabayaki", while only minor peaks were detected from the whole flavour obtained fran eel meat broiled without seasoning. 6
. Isolation and identification of carbonyls in both eel "Kabayaki" flavour and roasted seasoning flavour 1. Carbonyl component of eel "Kabayaki" flavours The whole flavour of eel "Kabayaki" obtained from eel meat, 490 g, was passed through a trap of 0.2% 2,4-DNPH-2N-hydro- chloric acid solution by nitrogen gas draft method. About 0.1 mg of the carbonyl component 2,4-DNPH of eel "Kabayaki" flavour that had been iscilated, was placed in a
10 ml Erlenneyer flask, and was decomposed by heating for one minute in a boiling water bath using 0.075 ml of 2N- sulfuric acid. H.S.V. of 5 ml free carbonyl component thus obtained, was analyzed by gas chromatography. Iso- Amylalcohol (H.S.V.) was used for internal standard. The result was that five components, besides the internal standard, were detected from the carbonyl fraction of eel "Kabayaki" flavour as shown in Fig. 5 (1). Three of those five--Acetaldehyde, Propionaldehyde (or Acetone or iso- Butyraldehyde) and iso-Valeraldehyde (or Methylethylketone)-- were identified as shown in Table 1. Also, in order to determine the position that the carbonyl components occupied on the gas chromatogram of the whole flavour of eel "Kabayaki", the whole flavour of eel "Kabayaki" was compared with the (46
carbonyl fraction of the eel "Kabayaki" flavour, that had been analyzed by the gas chromatographyunder similar conditions. It was found that most of the peak of the components of the whole flavour H.S.V., low boiling point zone,was cœstitutedof carbonyl components. (Refer to Fig. 5 (3).) 7
2. Carbonyl component of the flavour of roasted seasoning: From the whole flavour obtained from 17 ml roasted seasoning, carbonyl component of the roasted flavour of the seasoning 2, 4-DNPH was prepared as before and analyzed by the gas chromatography.As shown in Fig. 6 (1) four components, besides the internal standard, were detected of which three-- Acetaldehyde, Propionaldehyde (or Acetone or iso-Butyr- aldehyde) and iso-Valeraldehyde (or Methylethylketone)-- were identified as given in Table 1. From the above, it is shown that the carbonyl component of the eel "Kabayaki" flavour originates mainly from the roasted carbonyl component of the seasoning used. Isolation and identification of alcohol comronents of the eel "Kabayaki" flavour and the roasted seasoning flavour 1. Alcohol component in the eel "Kabayaki" flavour: The whole flavour from 500 g of eel meat, broiled with seasoning, was momentarily collected in a trap of cold hexane (-75 °C) by the nitrogen gas draft method. To this hexane solution (totalling 50 ml) was added 200 ml benzene, and later 0.25 g of 3,5-dinitrobenzoyl chloride and 0.25 g of sodium (47 acetate. It was then allowed to rest for two hours at 500; rinsed with 5% sodium hydroxide, 5% hydrochloric acid and distilled water, in that order; dried with sodium sulfate anhydride; then concentrated and dried completely, ;yielding 3,5-dinitrobenzoate, an alcohol component in the flavour of "Kabayaki" broiled eels. A minute amount of this benzoate 8 was placed in a 10 ml Erlernreyer flask and was decomposed in a boiling bath heated for two minutes using 0.075 ml of 2% potassium hydroxide. Free alcohol component H.S.V. 5 ml that was obtained from it was analyzed by gas chromato r: graphy. The internal standard used was iso-Amylalcohol The gas chromatographic analysis of the sample ethyl alcohol was carried out under similar chromatographic conditions as before, with free ethanol and free sample ethanol that were regenerated as before from the sample ethanol, 3,5-dinitrobenzoate. (Refer to Fig. 7 (2) & (3).) Consequently, one component, besides the internal standard, was detected from the alcohol fraction of the flavourof "Kabayaki" broiled eels as shown in Fig. 7 (1) and ethyl alcohol was identified as in Table 2.
2. Isolation and identification of the alcchol component of the flavour of roasted seasoning: From the whole flavour of the roasted seesoning obtained from 10 ml of the seasoning, dinitrobenzoate--the alcohol component of the roasted seasoning--was prer .Dred in a manner similar to that described above. It was analyzed by gas chroma- togrzey under similar operations and conditions. As a result, one component 'besides the internal standard, and a minor peak, were detected from the alcohol fraction of the roasted seasoning. It was identified as ethyl alcohol as shown in Table 2. It became clear, as stated above, that the component'...;^ that exists only in the flavour of eels broiled with season- ing and not in the flavour of eels broiled without seasoning, and that shows the -highest peak on the gas chromatogram, is ethyl alcohol. This ethyl alcohol is believed to ccene (48
frarn ethyl alcohol in the flavour of roasted seasoning.
Summary
1. The meat of four different kinds of fish--eel, conger eel, yellowtail and horse-mackerel, was broiled with season- ing obtained --having the same composition of ingredients.. A comparison of the H.S.V. gas chromatograms of the whole flavour of the broiled meats showed that besides the differences in the intensity of peaks, there were no other differences on account of different kind of fish.
2. As a result of the panel test,it was judged that in the flavour of eels broiled with seasoning, the carbonyl fraction and hydrogen sulfide were important.
3. Compared to the eels broiled with seasoning, those broiled without any lacked flavour, and their H.S.V. showed very minor peaks. On the other hand, H.S.V. of eels broiled with seasoning showed five peaks--one of which was
extremely strong (ethanol).
4. From the carbonyl fractions of the flavour of eels broiled with seasoning and the flavour of roasted seasoning, five
and four components respectively were detected, and three 10
components--Acetaldehyde, Propionaldehyde (or Acetone or (49 iso-Buthylaldehyde) and iso-Valeraldehyde (or Methylethyl-
ketone) were identified. Also, nbst of the peak
that was recognized in the low boiling point fraction of the whole flavour of eels broiled with seasoning, was confirmed
to consist of carbonyl components. These carbonyl components
were judged to originate from the components of the
roasted flavour of the seasoning used in the preparation of
"Kabayaki".
5. From the alcohol fractions of the flavour of eels broiled
with seasoning, and the flavour of roasted seasoning, one
component each was detected and they were confirmed to be ethyl
alcohol. The highest peak component of H.S.V. of the whole
flavour of eels broiled with seasoning was ethyl alcohol and
it was regarded as resulting from ethyl alcohol in the
flavour of roasted si.asoning.
For the installation of gas chromatogra.ph
used for the experiment, we benefitted in part from the
Ministry of Education Research Equipment Grant Program,
for which we wish to express our gratitude.
We also thank Misses Kondo, Sato, Nasu,
Haya shi and Fu j ishima , students who co-operated with us in this
experiment.
Bibliography
1) Obata, Y.: Shokuhin no Iro Ka Aii (Colour, Flavour and Taste of Food Prôducts), Gi^hodo, Tokyo, p.121. 11
(44
x2 (IV) ("2 x4 xs
,A) (V) x2 at) (V) x (11)
Wi 05 10 min 0 5 10 min (In) (In)
x4
1 LA0 5 10 min 0 5 10 min Fig. 1. GLC(PEG 6000) of whole flavor ob- Fig. 2. GLC(Silicone DC 550) of whole fla- tained from fish meats roasted with vor obtained from fish meats roasted seasoning. with seasoning. (I) Eel, (II) Conger eel, (III) Yellow- (I) Eel, (II) Congei eel, (III) Yellow- tail, (IV) Horse-mackerel, (V) Season- tail, (IV) Horse-mackerel, (V) Season- . ing. ing. 12.
(45
X2 xa
(H)
PAA,
(III) (IH)
DU 5 10min 0 5 10 min Fig. 3. GLC (PEG 6000) of whole flavor ob- Fig. 4. GLC(Silicone DC 550) of whole fla- tained from eel meat roasted with or vor obtained from eel meat roasted without seasoning. with or without sasoning. (i) Roasted with seasoning. (I) Roasted with seasoning. «I) Roasted without. seasoning. (II) Roasted without seasoning. (III) Roasted seasoning. (III) Roasted seasoning. 13
(46
(1)
Carbonyl fraction tŸarbon)i fraction
4 W x2
(5) St (Si
(2) St St N / Authentic carbonyIs Authentic carbonyle M1
CG C6
I U
.,;x2 (3) Whole 8acor ' «hote flavor
x2 St i St j
0 10 20 1 30 rnin 0 10 20 30 min Fig. S. GLC of carbonyls of eel meat roasted Fig. 6. GLC of carbonyls of roasted season- with seasoning. ing. St= internalI standard St=internal standard
(4-7
Table 1. te of carbonyls from eel meat roasted with seasoning and from roasted seasoning, in comparison with te of authentic carbonyls. -...„.., Eel meat roasted Roasted Sources with seasoning seasoning Authentic carbonyls Peak ' -...._, No. ---.., te te Name te 1 0.12 0.13 2 0.15 0.16 Acetaldehyde 0.16 3 0.21 0.22 Propionaldehyde 0.22 Acetone • 0.24 iso-Butyraldehyde 0.24 n-Butyraldehyde 0.32 4 0.35 0.34 iso-Valeraldehyde 0.36 Methylethylketone 0.36 Caproaldehyde 0.72 (5) (1.00) (1.00) (iso-Amylalcohol)* (1.00) 6 1.60
* internal standard
Table 2. te of alcohols from eel meat roasted with seasoning and from roasted seasoning, in comparison with te of authentic alcohols. Eel meat roasted Roasted ...------, . Sources with seasoning seasoning Authentic alcohols Peak _ No. "•-••-, te te Name te 1 0.38 0.38 Ethanol (from benzoate) 0.40 Ethanol (free) 0.40 (2) (1.00) (1.00) (iso-Amylalcohol)* (1.00) * internal standard 15
(48
(I) ill 1(2) Alcohol fraction . 8 St Alc(soeasohol nfmincgt)ion (1) (eel)
(2) St i* ■ —1`—^i \ •-••••/ -•--/
St (2) St (2) Authentic Et011 Authentic Et011 (from benzoate) (from benzoate)
....0.—..—...L.—__, ‘• i.. (3) (3) Authentic Et0H Authentic Et011 tfree) (free) ., St St 1 i — \------J--...... _,—.es ■--."
(4) ,, x 2 (4) — Whole flavor Whole flavor St (eel) (seasoning) 1 I st4
&%, e‘...A._____‘.._ .., l...._Ar• , 0 10 20 30 min 0 10 20 30 min . Fig. 7. GLC of alcohols of eel meat roasted Fig. 8. GLC of alcohols of roastnd season- with seasoning. ing. I St=internal standard St= internal standard 1 . ARCI3lVES FISHERIES AND MARINE SERVICE
Translation Series No. 3529
Changes in the composition of muscle lipids in some fish species frozen during storage
by I.V. Kizevetter, T.A. Pervuninskaja, and G.D. Trofimchuk
Original title: Izmeneniya Sostava Lipidov Myshts Nekotorykh Vidov Morozhenykh Ryb V Protsesse Khraneniya
From; Stud. Fish Food Technol. Vladiv. (4): 3-7, 1973
Translated by the Translation Bureau( IKR)
Multilingual Services Division . Department of the Secretary of State of Canada
Department of the Environment Fisheries and Marine Service Halifax Laboratory Halifax, N.S.
1975
7 pages typescript J -t "jr) 35›2.9.
• e • • •• DEPARTMENTOFTHESECRETARYOFSTATE SECRÉTARIAT D'ÉTAT git-R-i TRANSLATION BUREAU BUREAU DES TRADUCTIONS siettl'fl'54' . MULTILINGUAL SERVICES DIVISION DES SERVICES CANKCA DIVISION MULTILINGUES
TRANSLATED FROM - TRADUCTION DE INTO EN Russian English
AUTHOR AUTEUR I.V. Kizevetter, T.A. Pervuninskaja, G.D. Trofimchuk
TITLE IN ENGLISH - TITRE ANGLAIS CHANGES IN THE COMPOSITION OF MUSCLE LIPIDS IN SOME FISH SPECIES FROZEN DURING STORAGE
TITLE IN FOREIGN LANGUAGE (TRANSLITERATE FOREIGN CHARACTERS) TITRE EN LANGUE ÉTRANGÉRE (TRANSCRIRE EN CARACTÈRES ROMAINS) IZMENENIYA SOSTAVA LIPIDOV MYSHTS NEKOTORYKH VIDOV MOROZHENYKH RYB V PROTSESSE KHRANENIYA
REFERENCE IN FOREIGN LANGUAGE (NAME OF BOOK OR PUBLICATION) IN FULL. TRANSLITERATE FOREIGN CHARACTERS. REFÉRENCE EN LANGUE ÉTRANGÉRE (NOM DU LIVRE OU PUBLICATION), AU COMPLET, TRANSCRIRE EN CARACTÈRES ROMAINS.
Not available
REFERENCE IN ENGLISH RÉFÉRENCE EN ANGLAIS Studies in Fish Food Technology
PUBLISHER - ÉDITEUR PAGE NUMBERS IN ORIGINAL DATE OF PUBLICATION NUMÉROS DES PAGES DANS Not available DATE DE PUBLICATION L'ORIGINAL
YEAR ISSUE NO. VOLUME PLACE OF PUBLICATION ANNÉE NUMÉRO NUMBER OF TYPED PAGES LIEU DE PUBLICATION NOMBRE DE PAGES DACTYLOGRAPHIÉES Vladivostok, USSR 1973 4 7
REQUESTING DEPARTMENT Environment TRANSLATION BUREAU NO. MMSTÉRE-CLIENT NOTRE DOSSIER N° 1101012
BRANCH OR DIVISION Fisheries Service TRANSLATOR (INITIA LS) IKR DIRECTION OU DIVISION TRADUCTEUR (INITIALES)
PERSON REQUESTING Doris Hiltz IDEMANDÉ PAR
YOUR NUMBER VOTRE DOSSIER N°
DATE OF REQUEST June 24, 1975 te) UNEDITED TRANSLATION DATE DE LA DEMANDE For infornatien only TRADUCTION NON REVISEE Informaiion souloment LU (r) 5OS.200.10.5 (REV. 2/05) 7530-21.029-5333 ..11 729 36c9
.. DEPARTMENT OF THE SECRETARY OF STATE SECRÉTARIAT D'ÉTAT TRANSLATION BUREAU BUREAU DES TRADUCTIONS
MULTILINGUAL SERVICES DIVISION DES SERVICES DIVISION CANADA MULTILINGUES
CLIENT'S NO. DEPARTMENT DIVISION/BRANCH CITY NO DU CLIENT MINISTÉRE DIVISION/DIRECTION VILLE Environment Fisheries Service
BUREAU NO. LANGUAGE TRANSLATOR (INITIALS) N° DU BUREAU LANGUE TRADUCTEUR (INITIALES) 1101012 Russian IKR SEP ,- 3 1975
Studies in Fish Food Technology, No. 4, 1973, pp. 3-7, Vladivostok, USSR
CHANGES IN THE COMPOSITION OF MUSCLE LIPIDS IN
SOME FISH SPECIES FRÔZEN DURING STORAGE TRANSLATION • UNEDITED For informaii*n only TRADUCTION NON REVISEE By Informa.ion seulement I.V. Kizevetter, T.A. Pervuninskaya and G.D. Trofimchuk
When frozen fish are stored, lipids contained in their tissues 3*
undergo hydrolysis and oxidation by the action of enzymes and oxygen in
the air. It is customary to study the nature of changes in the properties
of lipids found in the tissues of frozen fish through the dynamics of
accumulation of the products of hydrolysis (free fatty acids) and oxidation
(peroxides, carbonyl compounds and hydroxy acids). It is of great interest
to study the variability of the ratio of lipid classes in the tissues of
frozen fish during storage in order to discover the connection between
peculiarities in the molecular composition of tissue lipids and their
resistance to spoilage brought on by hydrolysis and oxidation. These
changes formed the subject of our research.
* Numbers in the right-hand margin indicate the corresponding pages in the original.
11011.400«.10.41 2
The results of experiments in storing Pacific fish species in a frozen state have demonstrated that the rate of oxidation and hydrolytic decomposition of tissue lipids is not identical for frozen fish of different species alel t nikova, Vakhrusheva and others, 15711. Therefore, the following fish were selected for our investigation:, saBlefish
(Anoplopoma fimbria), a species which withstands storage in a frozen state, as well as Pacific saury CCololabis sairal and Pacific mackerel
(Pneumatophorus japonicus), species whose tissues contains lipids which are not resistent to hydrolysis and oxidation. Freshly caught fishes were frozen at a temperature of minus 28-30 °C. After the freezing process, sablefish was stored for 180 days, Pacific saury for 80, and
Pacific mackerel for 66 days at a temperature of minus 18 °C.
The extraction of muscle lipids from homogenized tissues was carried out according to the Bligh and Dyer method C19591. Lipid classes were determined by the thin-layer chromatography method.
100-200 mg of lipids (0.1-0.2 ml of chloroform solution) were placed on 18x24 cm plates for quantitative determination and 1.0-5.0 mg (0.02-
0.03 ml of chloroform solution) on 13x18 cm plates for qualitative determination.
In the preparation of plates we used brand KSK silica gel
(200 mesh) and the solvent system (hexane: sulphuric ether: glacial acetic acid) in a ratio of 80:20:1. The plates were developed with a 10% solution of phosphomolybdic acid (qualitative analysis) and with iodine vapours (quantitative analysis). After the Iodine had evaporated, the positions of lipid fractions on the silica gel were photographed and, following this, lipids were extracted using a mixture of Chloroform 3
and methanol C2:1Y-. A rotary, sttll was used to remove the solvent..
The amount of lipids of eacli class was determined by. the gravi.^metrîc metYi.od. As control samples, we used znonoglycer^.^des-, cfiolesterol,
diglycerides, free fatty, acids, triglycerîdes, and sterol es-ters- isolated
from the inuscle lipids of cod by- the preparative th±n-layer cfiromator-
graphy method in 3 solvent system described by, T.M. Vorob' eva (19.71y,
Apart from this we also used oleic acid and cholesterol for identification
purposes.
Examining the results of our research into native lipids of
fresh and frozen fish stored for various periods of time, we can ^ o^en establish that tissue lipids ïnablefisli, a species whïcFi withstands
prolonged storage, are composed of more than 70% triglycerides. The
amount of phospholïpids that they contain is 12% (see Tatïlej. After
120 days of storage there was, in the overall lipid composition of
sablefish, a decrease in the relative content of phospholîpids, mono-
glycerides and triglycerides. Over the same period there was a more
pronounced decomposition of phospholipids than of triglycerïdes, since
the initial quantity of phospholipids was reduced by 12.3%, while the
amount of triglycerides was reduced by only 3.1% from the initial content.
The decomposition process in these 2 lipid classes is accompanied by
an increase in the relative free fatty acid content. After 120 days
of storage their content had increased 3.5 times compared to what it
had been originally. During the following 60 days rapid triglyceride
de-composition was observed and, because of this, free fatty acid content
continued to increase. One may also note that after 120 days of storage
there was an increase in the relative cholesterol and sterol ester
content in the lipids of frozen sablefish. 4
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• : irWpasa pucSa Cccyzt6paa : jr, CaApa 5.^r,occu ^ax^" 7:cae:.:cpox xpaeea.^c^.:cpos ^cpasee.c cpox zpa:saa. . . :120 : I80 : :60 . 66 . :60 . su .à 8.^ocipoxaaa,u^+ I2,I I0,6 13,0 6,I 2,6 2,2 26,? 14.8 II,S 9,3"aor"11cpuO 3,I 2,I) 3,0 3,0 3,7 •4,2 2,6 3,9 9,2- I o;=ecnpW 215 2,8 4,0 2,9 1,5 I,3 3,2 3,1 I,I Il^o^o^e zxpsae I sscxo^ 2,1 7,3 8,7 2,2 3,3 3,2 3,3 '4,? 6,5 I2rpYrnunepaAS 76,3 73,9 66,8 81,5 85,? 85,0 60.2 71,8 68,2 j^ 5c^^ crepasox 3,9 3,4 4,5 4,3 3,2 4,0 4,0 ' I,8 3,5
Key to Table: 1. Changes in the ratio of lipid classes in the tissues of frozei'i fish during storage (in days) as a percentage of overall lipid content (average figures). 2. Sablefish. 8. Ï'hospholipids. 3. Pacific mackerel. 9. Monoglycerides. 4. Pacific saury. 10. Cholesterol. 5. Lipid classes. 11. Free fatty acids. 6. Duration of storage. 12. Triglycerides. 7. fresh. 13. Sterol esters.
^ Translator's note. In the Russian metric system commas are used instead of decimal points. In the body of the translation all commas have been changed to decimal points.
composition Triglycerides dominate the tissue lipid ^ of Pacific mackerel 5
(81.5% of the total lipid mass), but phospholipid content is low (6%).
Results of analyses indicate that when storage time is increased the relative phospholipid content of muscle lipids in frozen Pacific mackerel decreases substantially. After as little as 66 days of storage their content had dropped more than 70%. This tendency toward decrease is not evident in the triglyceride content. An increase in the monoglyceride and free fatty acid content and a decrease in the free cholesterol content is noted. 5 • •
The main muscle lipid mass of Pacific saury is also composed of
triglycerides. However, it is necessary to note the high native phospho-
lipid content (26.7). As storage time increases, a sharp drop is also
observed in the relative phospholipid content of frozen Pacific saury.
Thus, after 60 days it had dropped by 4 (sic. - Translator), and after
20 more days by an additional 12% of the original content (an overall
drop of 57%).
When storage time is increased, the relative monoglyceride and
free fatty acid content in the lipids of frozen Pacific saury increases,
with particular intensification of the process during the final 20 days.
This phenomenon can be explained not only by the high lability of lipids
in Pacific saury, but also by the specific nature of composition of
complexes of lipolytic enzymes in its tissues. It can also be noted that 6
the level of cholesterol content in the lipids of Pacific saury fell
noticeably during the final 20 days of storage.
Thus, native muscle lipids in the species studied differ in their
content of individual lipid classes and in their lability when the frozen
fish are stored at a temperature of minus 18 ° C. The phospholipid content
of sablefish, the species which best withstands storage in a frozen state,
hardly changed in the course of 180 days, while the relative content of
this lipid class in Pacific saury and Pacific mackerel, species which do
not withstand storage, decreased very significantly after only 60 days
of storage. The triglyceride content changed in different ways in the
lipids of the fish studied. For example, although the relative triglyceride
content in the lipids of frozen sablefish decreased noticeably, the relative
triglyceride content in the lipids of Pacific saury and Pacific mackerel
even increased somewhat towards the end of the storage period. An increase
in the free fatty acid content with increasing duration of storage is common 6 to the lipids of all three fish species studied. It may be hypothesized that in the lipids of frozen sablefish, the accumulation of free fatty acids occurs mainly due to triglyceride hydrolysis, whereas in frozen
Pacific saury and Pacific mackerel it is due to phospholipid hydrolysis.
It may also be assumed that any peculiarities observed in the ratio changes of lipid classes are connected not only with the nature of their chemical composition, but also with the peculiarities of lipolytic tissue enzyme complexes in different fish species.
CONCLUSIONS
1. Application of the thin-layer chromatography method to the study of natural fish lipids made it possible to discover the specific nature of ratios between various lipid classes which differ in their ability to withstand storage in a frozen state.
2. Triglycerides in Sablefish, a species which withstands storage, hydrolized more readily than tissue triglycerides in fish which do not withstand storage (Pacific mackerel, Pacific saury).
. 3. In the lipids of sablefish, a species which withstands storage, the accumulation of free fatty acids during storage occurs because of tri- glyceride hydrolysis, and in the lipids of Pacific saury and Pacific mackerel, species which do not withstand storage, because of phospholipid hydrolysis.
4. The peculiarities of triglyceride and phospholipid hydrolysis appear not only as a result of the nature of the molecular structure of native lipids, but also because of the specific native compositions of lipolytic tissue enzymes in various fish species. 7
BIBLIOGRAPHY
1. Vorob t eva, T.M. 1971. The effect of prolonged storage on muscle lipids in Baltic cod. "Rybnoe khozyaistvo", No. 8.
2. Mernikova, 0.M., M.N. Vakhrusheva, A.K. Myakisheva, 0.1. Kholosha. 1971. On the duration of storage of frozen fish. In coll.: "Studies in fish product technology", No. 5, TINRO.
IITERLUPÀ
,1' Bopoduaa T.M. 1971. Bamrsume.zziTemAloro spaseinin 3B ZME4- XY mime Oaremacriog Tp-ecuit. - "Punloe loss12z-3o r . B. e. Memliumnae 0. 4 ., M.E..2axpymema,..A..Mnzmze.-64. 0.Z-101=a. • 1971. 0 npoem.nler....aocni xpaaelim mopoaewer laud. B c6.:"Mc- cmanaus no temiczormii puc-aux 2po-ninen,Buz.5. Zn.TZEP0 2. nigh 3.G., W.G.D7e.r. 1555. A re:pid metLod of total eztraction and purification. Canaa., Ste-loll, v.37- '3r7r) 3:YQ9
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