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FISHERIES RESEARCH BOARD OF CANADA. Translation Séries No. 2818 .... considerd that these, fatty acids. are mostly of iso-series and partly anteiso-series .
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Translation Séries No. 2818

Studies on the little toothed whales in the West Sea area of.Kyushu-XVIII About higher branched chain fatty acids in head oil of little toothed whale - 2

by Ryoichi Kanazu, H. Morii and T. Fukub a- ra-,

Original title: • Kyushu chiho kaiki san kogata-keiruï no kenkyu-XVII •

Iruka rioyu chu no kokyu Sokusa 'shibosan-2

Fr°111 : Nagasaki Daigaku Suisan gakubu kenkyu hokoku (Bulletin .of the, Faculty of Fisheries), (28) : 1677171, 1969

Translated by the Translation' Bureau( 'fi() Division . MultingaServcs' Department of the Secretary of State of Canada

Department Of the Environment Fisheries Research Board of ' Canada Halifax Laboratory . Halifax, N.S.

1973

pages typescript

DiPARTMENT OF THE SECRETARY OF STATE



SECRÉTARIAT D'ÉTAT

BUREAU DES TRADUCTIONS

TRANSLATION BUREAU

DIVISION DES SERVICES

• MULTILINGUAL SERVICES DIVISION

MULTILINGUES

TRANSLATED FROM - TRADUCTION DE

INTO - EN

Japanese AUTHOR - AUTEUR

JT-1 Kanazu, H. •Iorii and T. Fukuhara TITLE IN ENGLISH

T,LTRE ANGLAIS

• Dtuclies of the little - toothed whale in the west sea area of Kyushu-X -wTT About higher brarched chain fatty acids in head oil of little toothed whale-1

TITLE IN FOREIGN LANGUAGE (TRANSLITERATE FOREIGN CHARACTERS) TITRE EN LANGUE ÉTRANGÉRE (TRANSCRIRE EN CARACTÉRES ROMAINS)

Kyushu chiho kaiki san kogatakeirui no kenkyu-XVII T

1-1

ka noun o 3-Yu no

REFERENCE IN FOREIGN LANGUAGE (NAME OF BOOK OR PUBLICATION) IN FULL. TRANSLITERATE FOREIGN CHARACTERS. RÉFÉRENCE EN LANGUE ÉTRANGRE (NOM DU LIVRE OU PUBLICATION). AU COMPLET, TRANSCRIRE EN CARACTÉRES'ROMAINS.

Bulletin of the FAculty of Fisheries Nagasaki Dalgaku Suisan gakubu kenkyu hokoku REFERENCE IN ENGLISH - RÉFÉRENCE EN ANGLAIS

Bulletin of the Faculty of Fisheries PUBLISHER- ÉDITEUR DATE OF PUBLICATION DATE DE PUBLICATION

YEAR ANNÉE

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YOUR NUMBER VOTRE DOSSIER N 0

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ISSUE NO. riumito

167-171 NUMBER OF TYPED PAGES NOMBRE DE PAGES DACTYLOGRAPHIÉES

19 69

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28

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MK

1 65 5f)),

,::JC

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DEPARTMENT OF THE SECRE

6.t -r,cr

TRANSLATION BUREAU



1

BUREAU OES TRADUCTIONS

MULTILINGUAL SERVICES

• DIVISION DES SEàVICES

DIVISION

MULTILINGUES

CLIENT'S NO. N° DU CLIENT

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Fi che



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165564

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MK

Studies on the Little Toothed Whales in the West Sea Area of Kyushu-XVII About higher branched chain.fatty acids in head oil of little toothed whale-1 Ryoichi

K.A.AZU,

Hideaki

MORII

and Tadanobu FUKUHARA

By means of gaS-liguid chromatography, a study vas carried out on the composition of fatty acids in oils of a porpoise (Neorneris phoccenoides), and it was discovered that the content of higher branched chain fatty acids is so much as has never been observed in oils of higher animals. Most of these higher branched chain fatty acids exist as sa.turated. Calculating the equivalent chain lengths on gas-liquid chromatograms, it is considerd that these, fatty acids. are mostly of iso-series and partly anteiso-series of odd carbon number. •

Reprinted from Bulletin of tue Faculty of Fisheries, Nagasaki University, No28; December. 196.9

scrf.- .,7C+0-I0-31

VILLE

Ut rI

ttiiS ,

Lint

.5 1973

. ,.

2

Highly branched acid.s such as phytanic acid1 and iso and anteiso acids which are single branched acids are known as higher branched chair_ fatt.y acids in the lipid of marine anii?ials.

It is already ?nnown, that all

of these acids are widely distributed. as saturated fatty acids although the amount is very small. This information .is distinctly shown by Ackman et al 's report.2 We have observed a large amount of higher branched chain fatty a.cid in the head oil of little toothed Tvhale. A high amount which was never seen in any other higher This report is the resv7t of our findings.

animals.

We liUe to extend our than':zs to professor Mizue Furthermore, part of the

for his valuable assistance.

research fund was provided. by the Piinistry of Education. Lx:aerimental methods and results SamDle oil

.

110- of oily composition.was obtained from the head. of Neorneris phocaenôides which was obtained from the Nagasaki City Aquarium on December, 1968. This oily composition was extracted with methanol-chloroform solution according to Bligh et al method.3 and about .50g of head oil was obta.ined. At the same time, Vhs of body oil was orta.inefd. from 190r^ of the s1kin for comparison. The properties of the oil are shown in Table 1.

3

Table 1.

Characteristics of oils of a porpoise

(Neonieris phocaenoides) . Head oil

Body oil

Refractive index N.2r;

1.4564

1.4663

Acid value

9.61

1.08

Saponification value

296,1

235.1

Iodine value (Wijs)

43.5

87.2

Unsaponifiables (%)

2.5

Reichelt-Meissl value

134.3

-

1.9

48.9

tee 14C1

15:Car

14:09r

15:Car

j 15;0

tà.

1

170

ro

1.5

20

25

Retention time (rnk; )

• Fig. 1.

Gas-liguid chrornato3rams of methyl esters of higni:i f a t - acids and its hydrov„enated product (doit.•.! line) in head oil of a porpoise (.,Viwincris pitoccenoi des) . Peaks beyond 17 : I are cut. corp.cr spiral tulomi, -, : 5 nun:. Column 1G.\ on sillan treated fire brick, 1 1.).', - t• : Hydr ,gen flame ioni.!attou Deteotor 111niUmin. Carrier ga. : 1 e,

are-paration of rii-her fatty acid meth,ylesters. 0,5,t; of the sample oil was separated and saponified a standard. ^method.,.

The unsaponifiable matte.r, was

removed fraatn the reaction mixture and the fatty acids. lOn?l of 10r^^ boron triflLlol'ide methanol

were collected.

solution was added to the acids collected and the acids The esters obtained from the above

were esterif ied .

reaction were distilled under reduced pressure and the volatile a.ci d. esters were removed.

The amount of esters

obtained from the head oil was 65% and the amount for the -^ skin oil was 8S i0 . O.lg of the ester was dissolved in l0rrzl of hexane and platinum black was added. The h.ydrogenated compound was obtained by passing hydrogen gas through the solution for. 3 hours under normal pressure.

GL,ry analysi s of the higher fatty ac i_s . The apparatus used for this experiment was Yanagimoto GGG--500 model,

f')% ethylenet lycola.dipate ( ^C^A ) was used as

a stationary phase, 'Fu.rther,

The length of the column was It. meters.

2 meter column packed with 5% ApieLori-L,

celite 545 as a stationary phase was used to analyse the hydrogenated fatty acid. esters.

The conditions for this

analjTsis were 2250G, hydrogen flapie H2 30ml,/min. , oarrier gas He lOml/niin,

Gas-liquid chromatogram of methyl esters of higher fatty acids and their hydrogenated products using EGA as a stationary phase is shown in Figure 1. The peaks 10:0Br-17:0Br seen on the hydrogenated products represent the compounds other than the straight chain compounds. There is no peak corresponding to these after 17:1. As can be seen in Figure 1, there is no noticeable change on the size of the peaks for 1003r-17:0Br before and after the hydrogenation. This suggests that the most of the acids are present in saturated form. Amount of higher fatty acids in the fat

of Meomeris phocaeneides

The composition of the fatty acids calculated from the gas chromatograms of the hydrogenated higher fatty acids is shown in Table 2. Since the amount of esters obtained from the head oil was 65% and 85% for the skin oil, the amount of higher branched fatty acids in the head oil is l7.6% and 7.4% for the skin oil. Equivalent chain length of 10:0 13r-17:0Br ingredients

ECL for higher branched fatty acids in the head oil was calculated from the res'ults obtained using EGA and 4 The results Apiezon-L according to Miwa et al's method. are shown in Table 3 with the ECL values -

Kaneda 5 for iso12:0-iso17:0.

obtained by

6

The composition of hydrogenated higher fa.tty acids in oils of a porpoise (Neomeris phoccenoides) •

Table 2.

_



10 : 0 Br 10 : 0 11 : 0 Br

,

12 : 0 13 : 0 Br 13 : 0 14: 0 Br 14: 0

15 : 0 Br

:1-. 0.5 2.4

1.6 3.8 9,3 0.4 4.3 13.6 . 9.0

i 1 . ,, 1

. .

. ' .

0.6 0.3 1.5 14.3 '3.6 1.3

2.1 6.1 26.7 1.8

: • i

17 : 0 18 : 0 20 : 0

1.0 16.7 2.1

. ; ;

22 : 0

3.1

4.2

27.1

8.7

15 : 0 16 : 0 Br 16 : 0 17 : 0 Br

Branched chain FA totals

Il

-

:

0.2 0.6 0.9 0.1

. ' '

11 : 0 12 : 0 Br

1 1

Body oil

Head oil

Fatty acids

.

'

;

.

1.7 33.4 0.8 1.7 28.4 3.3

see Fig. 1

1

. Table 3.

_

Equivalent chain lengths of peaks in Fig. I and in chromatogram on Apiezon-L as stationary phase, with c ■Dmparison data after KAZiEDA" .

Peaks

EGA 4m column

190'C

Apiezon-L 2m column 225C

Fatty- - acids

170'C

KANEDAS

10 : 0 Br 11 : 0 Br

9.65 10.57

10.68

: 12 : 0 Br 13 0 Br 14 : 0 Br

11.52 12.55 13.56 14.56 15.57 16.57

11.63

iso 12 : 0

12.63 13.64 14.63 15.61 16.61

iso 13 : ise 14 : iso 15 : iso 16: iso 17:

: 0 Br

16 : 0 Br 17 : 0 Br See Fig. 1

EGA On: column

i

0 0 0 0 0

KASEDA 5)

11.62 12.58 13.57 11.60 15.57 16.58

SE-30 1.5m coluMn KANE0A 3)

11.6 12.6 13.6 14.6 15.6 16.6

7 As can be seen from this table, the ECL values obtained from the result using EGA for 12:ODr-17:03r agreed. with the values obtained. by Kaneda for iso 12:0-

iso 17:0 ingredients.

Furthermore, the ECL values obtained

from the results •using Apiezon-L were quite similar to the values obtained by ;iaT,vl-ce et al6 for iso 13:0-iso 17:0 using Apiezon-M as a stationary phase. The uositions of peaks X1, X2 and X3 shown in Figure 1 were esti.mated. and ECL values were calculated.

The calculated results were 12.71, l4.75 and 16.72 respectively.

These values are almost the same as the values

obtained by Kaneda5 for anteiso 13:0, 15:0 and 17:0. The Values nbt_a,i ned. by TÇanPda ^TPr.e 1.2, ,71-^; i4-?4 and. 1-6.?'! respectively.

Discussion As already mentioned above, the lipid of TTeomer; s phocaeuioid.es

contained large amount of higher branched

fatty acids and the major part of the acids is made up of iso type.

Furthermore,

:ver,y slight amount of

odd number anteiso type acids too were found. in the lipid. 1/3 of the total acid is made up of415 carbon atoms.

The amount decreases as the number of carbon

atoms increases or decreases from 15. It is reported by Wolfe et al7 and. Sano8 , that unsa.tùrated hic;her branched fatty acids are present in the lipid ol marine animals. °te lilce to investip;cate this point in the future.

The amount of the skin oil was much higher than the amount of the head oil therefor e it is necessary ta•think that the amount of oil in a opoise is closer,to the amount of the oil in the5kin. Since the material used for this experiment was dead when we obtained it from the aquarium, there may - be a need for revising the amount of oil in the live sample. Ackman et al 9 have published many data on the isa and anteiso acids contained in 'marine animals.

The amount

according bo Ackman is usually below 0. 5 and the amount very seldom reaches 1%. According to the data available, there is an exceptionally large amont of hgigher branched fatty acid present in the head oil of popoise caught in this district. Therefore it is believed that this is a common property of a popoise's lipid. Summary An exceptionally large amount of higher branched fatty acids was detected in the head oil of Meomeris phocaenoide,s using GLC method. Furthermore it was dis-

covered that these acids are mostly saturated acids. According to the equivalent chain length obtained from the gas chromatograms, the majority of the acids •

belong to iso type. • There is also small amount of add number anteiso type acids- present in the lipid.

1) 2)

15, 456-.,460 (1966) : R. G:1CKuati. J. C. SIYOS and C. S. ToCttsR : J. Fis. Res. Bd. Canada, 24. 635650 (1957)

3)

E. G. BLIGH and W. J. DrER : Car:adian J. Biochem. Pllysiol., 37, 911 -917 (1959)

4)

T. K. \Int'a, K. L. -\IISOLAJCZAtc, E. R. EaRLr and 1. A. WOLFF : Anal. Ci,em., 32, 1739-..1742 (1960)

5)

T. KANErUA : J. Baci., 95. 2210-2216 (1968)

6)

J. C.

HaWf;E,

R. P.

HA\SEv and F. 1P. SHORLAND : J. Chromatog., 2, 547-551

(10i9)

7)

D. A. WOS.FE, H. V. R.ao and D. G. COFStcELL : J. _1tn. Oil Cia'f1aStS' SOC., 42. 633-..637 (1955) ;- : ü I f ^_'_, 11. 606 ^-610 (1967)

-$)

' `-^r

9)

R. G. ?,C[cxAN and J. C. Strus : Conap. Biocher:. Plasiol.. tg, 4.15...,:1,6 11965)

l.b1 10^;ra .bln .y l) Y. S^.pin

Oil

C.ham i c^r^r ( Yitlra oalrii )

8} Y. Sanoe Oil chemistr.y(Yu'•^asgaku)