Nutrition Research, Vol. 19, No. 10, pp.

1541-1549, 1999
Copyright 0 1999 Elsevier Science Inc.
Printed in the USA. All rights reserved
027 1-53 17/99/$+x front matter

ELSEVIER PI1SO271-5317(99)00110-4

THE POTENTIAL ANTICARCINOGENIC CONJUGATED LINOLEIC ACID, cis-9,tmns-11

Cl82 IN MILK OF DIFFERENT SPECIES: COW, GOAT, EWE, SOW, MARE, WOMAN

G. Jahreis, PhD’, J. Fritsche, PhD’, P. Mockel, MSc’, F. Schbne, PhD3, U. Moller, IV@,
H. Steinhart, PhD’
’Institute of Nutrition, Friedrich Schiller University, Jena; 2 Institute of Biochemistry and Food
Chemistry, University Hamburg; ‘Agricultural Institution of Thuringia, Jena; ’ Department of
Obstetrics, Friedrich Schiller University, Jena

ABSTRACT

The distribution of the potential anticarcinogenic fatty acid cis-9,tmw1 I-octadecadienoic

acid (rumenic acid) and other ~IVII.Sand cis fatty acids in milk fat of different ruminants and
non-ruminants including human milk was determined by gas-liquid chromatography. The
CLA isomer ci.s-9,11.01~.s- 1 1 was the predominant found Its variation in milk fat of the bulk
and individual samples was substantial (0.07 - 1.35 % of FAME). Because feed composi-
tion
_.“.. .and
. . . n,m,=n
.U.II.... mirmflnra
.L.._IUI.V.U infl,,~nrp
..II.UI.LII ;rnm&c&n\n
IIVLII”.I.,III.“LI nf
“I I;nnl&r
LILI”.b,b ~r;rl
UC,” in
L1, thn 1ULUbLL,
LLIC nam~n I(lrL”I J
fQrtr\rr

such as farm management and season were taken into consideration. CLA in milk of all
ruminants was season-dependent and there exists a close positive correlation to tram
vaccenic acid. Ewe milk is rich in CLA (1.1 %)_ Among non-ruminants mare milk was
nearly CLA-free (0.09 %). Human milk contained significantly more CLA (0.42 %, P <
0.01) in comparison wih the analyzed milk of the other monogastrides. There are differen-
ces between milk- and non-milk drinkers. The arrangement of the species according to the
increasing CLA concentration in milk is: mare, sow, woman, goat, cow, ewe. The higher
CLA content of ruminant milk compared with non-ruminant species is inversely correlated
to the content of PUFA and partly to MUFA
Q ,999Elsevia SClCDce Inc.
Key words: CLA, Rumenic acid, Milk fat, Cow, Goat, Ewe, Mare, Sow, Human milk

INTRODUCTION

Milk fat is an important source of potential anticarcinogens from the naturally occurring
conjugated linoleic acid (CLA) group. (‘i.s-Y.trmrs-I I-octadecadienoic acid is the major isomer.
Kramer et al. (1) therefore recommend naming this isomer from bovine milk fat as “rumenic acid”.
In ruminants dietary polyunsaturated fatty acids are affected by enzymatic activity of microorga-
nisms in the rumen. The isomerization of linoleic acid by the anaerobe Blr~r-ildh~io,fih~i.soh,erl.sis a
reaction in which the cis- 12 bond is converted to a trarrs- 11 bond (2)

Address for correspondence: Dr. Gerhard Jahreis, Friedrich Schiller University Jena, Institute of
Nutrition, Dornburger Str. 24,D-07743Jena, Telephone: +49 (0)3641 949610, Fax: +49 (0)3641
949612, E-mail: b6jage@zuni-jena.de

1541
1542 G. JAHREIS et al.

Theoretically, linoleic acid may be transformed into at least 24 isomers containing conjugated
double bonds at positions 7,9; &IO; 9,ll; 10.12; 11,13 and 12,14. Each of these isomers may exist
in the ciu’trar~s, tram cis, cis cis or tram trams configuration. Most of these isomers are contained
in commercially available preparations produced from linoleic acid-rich sunflower oil. The isomeric
distribution of an alkali isomerized CLA reference (Sigma) was reported to be: CO.05 % 18:2 t13t15;
0,37 % 18:2 t12t14; 0.79 % 18:2 tllt13; 1.46 % 18:2 tlOt12; 1.20 % 18:2 t9tll; 0.41 % 18:2
t8tlO; 0.14 % 18:2 t7t9; 0.15 % 18:2 12,14 c/t; 22.75 % 18:2 11,13 c/t; 29.60% 18:2 lo,12 c/t;
28.36 % 18:2 9,11 c/t; 12.46 % 18:2 8,lO c/t; 0.92 % 18:2 12c,14c; 0.59 % 18:2 11~13~; 0.69%
18:2 ~10~12; and 0.12 % 18.2 c9cll (3).

The isomer(s) responsible for the wide variety of beneficial effects attributed to CLA (e. g.
antiatherosclerotic effects, antidiabetic effects, alteration of body composition, modulation of
immune function; 4, 5, 6, 7) have not been identified. The predominantly occur&g isomer in milk
fat, i. e., cis-9,nmws-l I-octadecadienoic acid appears to be an anticarcinogen (8, 9, 10). This isomer
has been ingested by humans since the domestication of ruminants. Monogastric animals can also
produce CLA. Brown and Moore (11) have isolated strains of B. ,jhri.sohwrr.s from human faeces.
CLA is also produced in conventional, but not in germ-free rats after linoleic acid intake (12). The
contribution of colon-derived CLA to the total CLA in monogastrides is negligible.

The CLA in monogastric tissue lipids and milk fat is derived primarily from ruminant products
in the diet. However, Pollard et al. (13) and Salminen et al. (14) showed that some CLA may be
formed by conversion of dietary tra~rs fatty acids, possibly by A 9-desaturation of trans-vaccenic
acid. Numerous studies have addressed the various factors that affect the CLA content of cow milk
ranging from 0.2 to 2.4 % of total fatty acids (1.5, 16, 17, 18, 19, 20, 2 1). CLA content in human
milk has been reported to vary from 0.2 to 1.1 % of total fatty acids (15, 17, 22).

The objective of the present study was to analyze CLA and other fatty acids in commercially
offered milk of ruminants in comparison to CLA in milk from non-ruminants to evaluate their
relative importance as sources of the potential anticarcinogen cis-9,trmw1 I-octadecadienoic acid
for human nutrition.

MATERIAL AND METHODS

Milk sample collection

1. Ruminant milk: Bulk-milk samples were taken four times a year (2 samples each). An ecologi-
cal farm housing 12 cows, 45 milk sheep and 62 goats was chosen. Similar roughage or pasture
were fed to all three species of ruminants. Not all animals were lactating at the four collection
times (esp. ewes). Bulk-milk samples were collected at the same time from a second goat farm
with about 750 indoor fed animals.

2. Mare milk: The samples (n = 12) were collected from a mare-milk farm, from bulk milk of 120
mares (Haflinger breed). The mares were only milked during pasture time from May to Septem-
ber.

3. Sow milk: The samples were taken from 12 individual animals after stimulation of milk flux by
oxytocin injection at different points during the 30 day lactation.
 CIA IN MILK OF DIFFERENT SPECIES 1543

4. Human milk: Breast milk was collected from 29 volunteers during their stay at the University
Department of Obstetrics. A questionnaire addressing nutritional habits was also completed by
the women.

Fatty acid analysis: The milk was frozen immediately after collection (-18°C) and was later
freeze-dried. The milk powder was used for fat extraction. The freeze-dried milk was thawed at
room temperature (25°C). Using methods described elsewhere (3), fat from 2 g dried milk was
extracted with 15 ml of chloroform : methanol = 2 : 1 (v/v). Fatty acid methyl esters (FAME) were
prepared by transesterification with potassium methylate. Analysis of FAME was carried out on a
HP 5890 Series II plus gas chromatograph fitted with an automatic sampler (HP 7673) for a multi-
type injection (split ratio 1:20) and a flame ionization detector (FID). A tised silica capillary column
coated with lOO’?/ocyanopropyl polysiloxane (CP Sil 88), 50m, 0.25 mm ID, 0.25 pm film thickness
was used to analyze the FAME content. Helium was selected as carrier gas (flow ca. 1.3 ml/min).
The oven temperature was 175°C until the 18: 1 trans isomers eluted and was then increased at a rate
of S”C/min to the final temperature of 225”C, which was held for 15 min. The injector port tempera-
ture was 220°C and the detector temperature was 260°C. Fatty acids were identified by comparison
with the retention times to standard FAME. The standards and the CLA mixture were purchased
from Sigma (Deisenhofen, Germany), the individual CLA references (trms-9,trcvw 11; cis-9,cis- 11;
t~r~lO,ci.s-12) were obtained from Matreya (Pleasent Gap, PA, USA).

Statistics: All data were analyzed with the SAS software package (SAS Institute Heidelberg,
Germany). The results are given as arithmetic mean ??standard deviation.

RESULTS

Different CLA could be detected in all milk samples. The predominant isomer cis-9,?ra~s-11
was determined as well as small amounts of Watrs-9,harls-1 1 (0.00 - 0.04 % of FAME) and trans-
lO,cis-12 (0.00 - 0.08 %) were found. Consequently, this study focuses on the primary isomer cis-
9,tl-nlzs-11. The other two minor CLA components are negligible.

Ruminants: The concentration of milk CLA in different ruminant species varied with the seasons
(Fig. 1). There was a distinct decrease at the end of the winter season (March) in all ruminant
species with exception of the indoor goats. The latter have the lowest content of CLA in their milk
throughout the whole year The greatest seasonal differences were measured in ewe milk: 1.28 % in
summer (July) and 0.54 % at the end of the winter period (March). Ewe milk was collected in
October, because most animals were not lactating in December (Fig. 1 and 2). This milk fat contains
not only the highest concentration of CLA, but also the highest content of total tram fatty acids as
well as tars vaccenic acid. A season-dependent shape is obvious for the three fatty acid groups
(Fig. 2).

Monogastrides: The CLA content ranged from 0.29 to 0.7 1 % in human milk fat, 0.19 to 0.27
in sow milk and 0.05 to 0.12 % in mare milk with the following mean values: human milk 0.4 %,
sow 0.2 % and mare milk 0.1 %. Mare and sow milk contain negligible amounts of CLA and truns-
1 I-octadecenoic acid (Fig. 3). The analyses of human, sow and mare milk showed no seasonal
dependency of CLA content (data are not shown).

The arrangement of the species according to the increasing CLA concentration in milk is shown
in Table 1. The higher CLA content of ruminant milk compared with non-ruminant species is
inversely correlated to the content ofPUFA (C18:2 06, C18:3 03, C18:3 06, C20:2 06, C20:3
1544 G. JAHREIS et al.

06, C20:4 06, C2O:S ~3, C22:4, C22:S 03, C22:6 03) and partly to MUFA (C14:l c9, C16:l c9,
C 18:l c9, C18:l cll, C2O:l cll, C22:1, C24:l).

0.0 I I I I 1

OctlDec

Figure 1: CLA content of ruminant milk fat in different seasons (% of total FAME)

-+Cl8:1 tll
-11 Cl 8:2 c9tll

July Oct/Dec March May

Figure 2: Trms fatty acids, WCIIISvaccenic acid and CLA content of ewe-milk fat in
different seasons (% of total FAME)
 CLA IN MILK OF DIFFERENT SPECIES 1545

4
0 Cl8:l tll
3 ---- I C18:2 c9tll

0
Mare sow Woman Goat cow Ewe

Figure 3 : Tram vaccenic acid and CLA content in milk fat of different species

TABLE 1

Percentage of monounsaturated and polyunsaturated fatty acids as well as CLA in the milk fat of
non-ruminants and ruminants (% of total FAME, mean values)

MUFA PUFA CLA

20.7 f 1.2 36.8 f 3.2 0.09 f 0.04

51.8 f 5.8 12.4 f 1.7 0.23 f 0.02
33.2 f 2.9 12.5 f 2.9 0.39 f 0.08

Ruminants
4. Goat, pasture 26.9 f 5.4 2.58 f 0.21 0.65 f 0.25
5. Goat, indoor 21.8 ??0.9 4.05 f 0.25 0.64 + 0.15
6. Cow 23.2 f 1.7 2.42 f 0.60 1.01 f 0.25
7. Ewe 23.0 f 3.2 3.85 f 1.35 1.08 f 0.32

DISCUSSION

Much of the variation in CLA content in milk of ruminants is attributed to seasonal influences.
From previous studies it is known that milk from cows grazing pasture had higher CLA content.
Dhiman et al. (24) found CLA values between 8.4 and 22.7 mg/g milk fat of cows which consumed
either l/3,2/3, or all of their daily feed from the pasture. During one year we analyzed monthly milk
of cows fed diets containing only conserved forages in comparison with cows on an ecological farm
grazing during the summer season ( 19). The mean CLA content of the indoor group amounted to
0.34 % of total FAME and the percentage of ecological group to 0.80 % with the highest values in
summer time (1.14 Oh). The results of this study show a similar tendency with the highest value of
1546 G. JAHREIS et al.

1.23 % in July and a mean value over the year of 1.Ol % (Fig. 1, Tab. 1). A significant influence of
grass intake on milk CLA content in ruminants is obvious according to Dhiman et al. (18). Unlike
our results with cows (19) there are no differences between the indoor-fed goats (small variation
during the year) and the pasture-fed goats. The different capacity of milk-fat synthesis between cows
and goats may play a role.

Ewe milk has the highest CLA, but also the highest content of vaccenic acid (Fig. 2). The
reason seems not to be the feed-derived PUFA, because the three ruminant species were fed similar
forages. Lawless et al. (25) reported an enormous variation in milk CLA between individual animals.
Consequently, species differences may offer varying living conditions for B. fibtGdvens. Ewe milk
fat is the richest source of CLA, which was also shown for lamb meat and body fat (15).
Using all results of different species the following equation is calculated (% FAME):
y = 0.318x + 0.141
(y = cis-9,tm1.s- 1 1 CLA x = twrns vaccenic acid; multiple correlation coefftcient = 0.905).
The close correlation underlines the probability that in addition to direct synthesis of CLA by
microbes in rumen, the endogenous production of CLA contributes to milk fat CLA by A9-
desaturation of Irtnrs- 11-octadecenoic acid in body tissues (13, 14, 26).

Mare’s milk had the lowest CLA content of the milks analyzed in this study (Fig. 3). Plant tissue
does not contain either CLA or /IZVI.Svaccenic acid. Our results confirm that the caecum microbes
of horses do not contribute to CLA enrichment of milk. Mare milk has the highest concentration of
PUFA (no biohydrogenation of the grass polyunsaturated fatty acids) and sow milk the highest
concentration of MUFA (effect of A9-desaturase and influence of feeding). Sow milk contains
slightly more CLA than mare milk which is probably food-derived. To our knowledge, this is the
first study in which sow and mare milk CLA were analyzed.

TABLE 2
CLA content in human milk fat

CLA (% FAME)
Reference
mean range

Australian women 0.58 0.31-0.85 Fogerty et al. (1.5)

Hare Krishna 1.12 0.97-1.25 Fogerty et al. (15)
US-women 0.18 0.14-0.28 Jensen et al. (22)
German women 0.27-0.53 this investigation
US-women 3!6;, 2.23-5.43” McGuire et al. (17)
1) mg/g fat

In comparison with these non-ruminants, human milk is relatively rich in CLA. Fogerty et al.
(15) analyzed 0.58 % FAME in human milk from Australian women. They observed on the other
hand that milk of women who belonged to the Hare Krishna religious sect, whose diet excludes
meat, but includes butter and milk contained twice the amount of CLA (Tab. 2). Jenson et al. (22)
measured the lowest CLA concentrations in human milk determined by GLC and confirmed by
GLC-MS (Tab. 2). The authors reanalyzed milk samples from an earlier fish oil supplementation
study.

Both the mean CLA content and the range of our results are comparable with the values of
McGuire et al. (17). The subgroup of non-milk drinkers (n = 6) among women has lower CLA
 CIA IN MILK OF DIFFERENT SPECIES 1547

concentrations in their milk (2 = 0.33, range: 0.27 - 0.40 % of FAME). McGuire et al. (17)
measured the tram- 1O,cis- 12 and found that 83 - 100 % of total CLA were present as cis-9,trans
11, and that only 57 % of samples contained both isomers. The mean proportion of the
anticarcinogen cis-9,trarw 11 C 18:2 in our samples amounted to 93 %. Consequently, a breastfed
infant drinking 750 ml milk consumes daily about 120 mg CLA in 30 g fat.

The daily CLA intake of adults was estimated according to data of the German Nutritional
Survey to be about 400 mg (23, 27). Nearly 60 % of the total CLA in the average German diet is
derived from milk, dairy products and beef. The potential benefits of the anticarcinogen cis-9,trans-
11 C18:2 could be better utilized by well-directed selection of foods and should also be conveyed to
the breastfed infant. According to the findings of this study ewe milk and cow milk of the summer
season are the richest CLA sources.

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 CLA IN MILK OF DIFFERENT SPECIES 1549

24. Dhiman TR, Anand GR, Satter LD, Pariza M. Conjugated linoleic acid content of milk from
cows fed different diets. J. Dairy Sci. 1996; 79: S 1, P35.

25. Lawless F, Murphy JJ, Harrington D, Devery R, Stanton C. Elevation of conjugated cW-9,
W~~r.s-1
I-octadecadienoic acid in bovine milk because of dietary supplementation. J. Dairy Sci.
1998; 81: 3259 - 3267.

26. Griinari JM, Dwyer DA, McGuire MA, Bauman DE, Palmquist DL, Nurmela KVV. Trms-
Octadecenoic acids and milk fat depression in lactating dairy cows. J. Dairy Sci. 1998; 81:
1251 - 1261.

27. Jahreis G. Funktionelle Inhaltsstoffe aus tierischen Nahrungsmitteln. Akt. Ernahrungsmed. 1999
(in press)
Accepted for publication February 26, 1999.