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Institut für Biochemie und Technologie der Fette, H. P. Kaufmann-Institut, BAGKF, D-48147 Münster, Germany
1To whom correspondence should be addressed.
 |
ABSTRACT |
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 TOP ABSTRACT INTRODUCTIONMATERIALS AND METHODSRESULTSDISCUSSIONREFERENCES |
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KEY WORDS: • coriander oil • high oleic sunflower oil • oleic acid • petroselinic acid • rats
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INTRODUCTION |
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TOPABSTRACTINTRODUCTIONMATERIALS AND METHODSRESULTSDISCUSSIONREFERENCES |
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, Grundy et al. 1988
, Mattson and Grundy 1985
, Mensink and Katan 1987
and 1989
,
Mensink et al. 1989
, Wahrburg et al. 1992
). A few studies have appeared on the effects of dietary
fats with high levels of naturally occurring positional isomers of
oleic acid, such as cis-vaccenic acid [18:1(n-7)]
(Reichwald-Hacker et al. 1979b
) or petroselinic acid
[18:1(n-12)] (Hoy and Holmer 1981
, Mohrhauer et al. 1967
).
cis-Vaccenic acid, a naturally occurring unusual positional
isomer of oleic acid, is a minor constituent of many fats and oils of
plant origin (Mukherjee and Kiewitt, 1980
), whereas
seeds of Umbelliferae, such as parsley (Petroselinum
rubrum), fennel (Foeniculum vulgare) and coriander
(Coriandrum sativum) contain high levels of petroselinic
acid as part of triacylglycerols (Meier zu Beerentrup and Röbbelen 1987
). Breeding of coriander as a renewable resource for
petroselinic acid is in progress (Eierdanz and Hirsinger 1990
) in view of the potential use of this fatty acid for the
production of specific oleochemicals (Princen and Rothfus 1984
).
Studies in vitro have shown that triacylglycerols containing
petroselinoyl moieties are hydrolyzed by pancreatic lipase at much
lower rates than those containing oleoyl and other C-18 acyl moieties
(Heimermann et al. 1973
, Seher and Fiebig 1983
). Our earlier studies revealed that petroselinic acid from
triacylglycerols of coriander oil is incorporated extensively into the
lipids of heart and liver of rats and, concomitantly, the concentration
of arachidonic acid in these tissues is reduced (Weber et al. 1995
). Moreover, dietary petroselinic acid is metabolized in
the rat liver via ß-oxidation and chain elongation to shorter and
higher homologs, respectively; however, petroselinic acid is a
dead-end metabolite of the desaturation-chain
elongation-reaction-cycle (Weber et al. 1997
). In
continuation of the above studies, we report here the composition and
stereospecific distribution of acyl moieties, particularly isomeric
C-18 monoenoic acyl moieties, in adipose tissue triacylglycerols of
rats fed coriander oil (COR)3
compared with those
fed high oleic sunflower oil (HOS).
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MATERIALS AND METHODS |
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TOPABSTRACTINTRODUCTIONMATERIALS AND METHODSRESULTSDISCUSSIONREFERENCES |
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Triglyceride and fatty acid methyl ester standards as well as ethyl magnesium bromide (1 mol/L solution in methyl tert-butylether) were obtained from Sigma-Aldrich (Deisenhofen, Germany). Analytical grade and HPLC-grade solvents were products of Merck (Darmstadt, Germany).
Diets.
Refined, bleached and deodorized coriander oil was a generous gift of A. Westfechtel, Henkel Cie & KG, Düsseldorf, Germany. Refined, bleached and deodorized high oleic sunflower oil was kindly provided by W. Holtmeier, Noblee & Thörl, Hamburg, Germany. Corn oil was purchased from a local supermarket.
Isocaloric pelleted feed (metabolizable energy 13.1 kJ/g) containing
recommended levels of protein, carbohydrates, vitamins and nutrient
minerals (Drepper and Udes 1968
) as used in the
semipurified Altromin standard diet (Kontrolldiät C 1000) for
rats4
and one of the above experimental oils (120 g/kg
diet) plus corn oil (20 g/kg diet) were prepared by Altromin
International, Lage, Germany.
Animal experiments.
Weaned male Wistar rats (Lippische Versuchstierzucht, Extertal, Germany), weighing 85–90 g, were caged individually and divided into groups of 10. The rats were kept in rooms with adequate ventilation at a temperature of 22°C and a relative humidity of 60%. The rats had free access to feed and water at all times until 12 h before they were killed.
Rats were fed for 10 wk. At the end of the feeding, the rats were killed by ether narcosis followed by section of the aorta. All procedures for the animal experiments were approved by the official commission for animal experimentation [Der Regierungspräsident Münster, permission no. 26.0834 (48/90) of November 29, 1990]. Organs and epididymal, subcutaneous, as well as perirenal adipose tissues were rapidly removed and kept at -60°C until the lipids were extracted.
Lipid analysis.
Lipids were extracted from the adipose tissues and feed according to
Bligh and Dyer (1959)
. Total lipids were fractionated by
chromatography on layers of Silica Gel H (Merck) using hexane/diethyl
ether/acetic acid (80:20:1, v/v/v). The fractions of triacylglycerols
that had been identified by co-chromatography with a standard were
isolated, extracted from silica gel with water-saturated diethyl
ether and concentrated. Aliquots of the triacylglycerol extracts (~1
mg) were treated with 50 µL trimethyl sulfonium
hydroxide and 200 µL 1,2-dichloroethane to prepare
methyl esters of their constituent fatty acids. The mixture was shaken
vigorously for 1 min and kept at room temperature for 15 min before
direct injection onto the gas chromatograph (Schulte 1993
).
Methyl esters were analyzed by gas chromatography in a Hewlett Packard 5890 instrument (Böblingen, Germany) on a 40-m DB-23 (methyl/50%-cyanopropyl silicone, J & W, ASS-Chem, Bad Homburg, Germany) fused silica capillary column (0.18-mm i.d., 0.2-µm film thickness). Hydrogen was used as carrier gas at 20 cm/s linear velocity; the split ratio was 1:10. Temperature was programmed from 170°C (17 min isothermal) at 7°C/min to 225°C (10 min isothermal). Injector and detector temperatures were set at 280°C. Samples from the COR group containing methyl petroselinate were analyzed similarly on a 60-m DB-23 capillary column (0.25-mm i.d., 0.25-µm film thickness) using the following temperature program: from 150°C at 6°C/min to 180°C (18 min isothermal) and then at 20°C/min to 250°C (10 min isothermal). Peaks were integrated using Hewlett-Packard GC ChemStation software.
Aliquots of triacylglycerols from adipose tissues and feed were
subjected to Grignard degradation; the sn-1,3
diacylglycerols were isolated from the degradation products by
chromatography on layers of silica gel impregnated with boric acid (5 g
boric acid/100 g silica gel) (Christie 1982
). The
fraction of sn-1,3 diacylglycerols was converted to
methyl esters and analyzed by gas chromatography as described above.
The composition of acyl moieties at the sn-2 position of
triacylglycerols was calculated from the composition of the
sn-1,3 diacylglycerols and that of the total
triacylglycerols (Christie 1982
).
Triacylglycerols from adipose tissues and feed were analyzed by HPLC as follows. The HPLC system consisted of a Merck-Hitachi pump L-6200 (Merck) equipped with a Kontron (Kontron Instruments, Milan, Italy) UV/visible HPLC 332 detector (Merck) set to a wavelength of 210 nm and an ACS (Applied Chromatography Systems, Macclesfield, UK) mass detector model 750/14 (thermostated to 55°C), which were used in series. UV and mass traces were monitored and evaluated in a KromaSystem 2000 data acquisition unit (Kontron Instruments). Triglyceride species were separated isocratically with acetonitrile/acetone (62:38, v/v) on a Merck LiChrospher RP-18 column (250 mm x 4-mm i.d. and precolumn) at 25°C. The flow rate was set at 1 mL/min. Injections (~0.2 mg triglycerides) were carried out with a Rheodyne 7161 sample injector (Cotati, CA) equipped with a 20-µL sample loop. Synthetic triglyceride standards and those isolated from coriander oil and high oleic sunflower oil by argentation TLC were used for comparison.
Statistical analysis.
Statistical evaluation of the data was conducted using a Statgraphics
one-way ANOVA computer program (STSC, Rockville, MD); a probability
value (P) of <0.01 was considered to be significant in
the multiple range analysis. Cochran’s C test and Bartlett’s test
were used as statistical tests for homogeneity of variance (Box et al. 1987
). ANOVA was performed on the homogenous data.
If ANOVA was significant, Tukey’s honest significant differences test
(Box et al. 1987
) was used for pairwise comparisons
between groups using the above computer program.
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RESULTS |
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TOPABSTRACTINTRODUCTIONMATERIALS AND METHODSRESULTSDISCUSSIONREFERENCES |
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, shows that the major difference between the dietary triacylglycerols
was in the level of isomeric octadecenoic acids, i.e., petroselinic
acid [18:1(n-12)] and oleic acid [18:1(n-9)], and in the level of
linoleic acid [18:2(n-6)]. Thus, the dietary triacylglycerols of the
HOS group had a high proportion of 18:1(n-9), those of the COR group a
high level of 18:1(n-12), whereas the proportion of 18:2(n-6) was
slightly higher in the COR (21.2%) than in the HOS group (16.9%)
(Table 1)
. No effort was made to balance exactly the level of 18:2(n-6)
in the two oils by adding, for example, safflwer oil to HOS because
this would have substantially lowered the level of 18:1(n-9) in HOS. We
decided to focus on dierary oils having high levels of isomeric
octadecenoic acids rather than the same level of 18:2(n-6). Dietary
triacylglycerols of both groups contained similar proportions of
palmitic (16:0) acid (Table 1)
. Stereospecific analysis of the two
dietary triacylglycerols showed that in the triacylglycerols of the
coriander oil group, petroselinic acid was esterified to a
substantially greater extent at the sn-1,3 positions than at
the sn-2 position, whereas oleoyl and, in particular,
linoleoyl moieties occurred predominantly at the sn-2
position (Table 1)
. In the dietary triacylglycerols of the high oleic
sunflower oil group, oleoyl moieties were distributed almost equally
between the sn-1,3 and sn-2 positions at the
glycerol backbone, whereas 18:2(n-6) was esterified predominantly at
the sn-2 position and 16:0 was located to a somewhat greater
extent at the sn-1,3 positions than at the sn-2
position.
|
), food consumption, body weight and
feed efficiency, measured as weight gain to food intake, did not differ
significantly between the two groups.
The fatty acid composition of the triacylglycerols of epididymal,
subcutaneous and perirenal adipose tissues of the experimental rats
(Table 2
) broadly reflected the composition of the dietary oils (Table 1)
. Thus,
adipose tissue triacylglycerols of rats fed the COR diet contained
petroselinic acid as the most abundant octadecenoic acid, whereas the
relative proportion of oleic acid in these lipids was significantly
lower than in rats fed the HOS diet (Table 2)
. Similarly, the adipose
tissue triacylglycerols of rats fed the HOS diet contained oleic acid
as the most abundant octadecenoic acid and some minor proportions of
cis-vaccenic acid, but no petroselinic acid. Interestingly,
the proportion of cis-vaccenic acid was significantly higher
in the adipose tissue triacylglycerols of rats fed the COR diet than in
those fed the HOS diet (Table 2)
. cis-4-Hexadecenoic acid
[16:1(n-12)], formed by ß-oxidation of petroselinic acid, was found
only in the adipose tissue triacylglycerols of rats fed the COR diet
(Table 2)
. Linoleic acid was esterified in the adipose tissue
triacylglycerols at significantly higher levels in rats fed the COR
diet compared with those fed the HOS diet, whereas the proportion of
palmitic acid in the adipose tissue triacylglycerols did not differ
significantly between the two dietary groups; linolenic and arachidonic
acid were present in the adipose tissues in very small proportions only
(Table 2)
.
|
. For example, in the COR group, a small but
significantly higher (P < 0.01) level of 18:2(n-6)
moieties was found in the triacylglycerols of subcutaneous adipose
tissue compared with epididymal adipose tissue. Similarly, for the HOS
group, significantly higher (P < 0.01) proportions of
18:1(n-9) and 18:2(n-6) moieties were observed in subcutaneous adipose
tissue compared with epididymal adipose tissue (Table 2)
.
Table 3
shows the composition of acyl moieties at the sn-1,3 and
sn-2 positions of the triacylglycerols of epididymal,
subcutaneous and perirenal adipose tissues of the experimental rats.
Stereospecific distribution of acyl moieties in the triacylglycerols of
all three adipose tissues (Table 3)
broadly reflected the distribution
of acyl moieties in the corresponding dietary triacylglycerols (Table 1)
. Thus, in the rats fed the COR diet, petroselinic, palmitic and
stearic acids were esterified predominantly at the sn-1,3
positions, oleoyl moieties were fairly evenly distributed between the
sn-1,3 and sn-2 positions, and linoleoyl moieties
occurred to a substantially greater extent at the sn-2
position than at the sn-1,3 positions (Table 3)
. In the
triacylglycerols of all three adipose tissues of rats fed the HOS diet,
oleoyl moieties were evenly distributed between the sn-1,3
and sn-2 positions, whereas palmitoyl and, particularly,
stearoyl moieties predominated at the sn-1,3 positions, and
linoleoyl moieties occurred to a substantially greater extent at the
sn-2 position than at sn-1,3 positions (Table 3)
.
However, the proportions of individual acyl moieties at the
sn-1,3 positions of triacylglycerols of the three adipose
tissues within a particular feeding group (COR or HOS) did not differ
significantly (data not shown).
|
. Tripetroselinoyl-glycerol (PePePe) and
dipetroselinoyl-linoleoyl-glycerol (PeLPe) were the predominant
triacylglycerol species of the COR diet, whereas the HOS diet contained
trioleoyl-glycenol (OOO) as the most abundant triacylglycerol species.
Feeding the COR diet rather than the HOS diet resulted in the
generation of numerous triacylglycerol species in addition to those
mentioned above; thus the formation of considerable proportions of OLPe
(oleoyl-linoleoyl-petroselinoyl-glycerol, 13.1%) and PPePe
(palmitoyl-dipetroselinoyl-glycerol, 12.4%) was observed. These
results were paralleled by a dramatic decrease in proportions of
triacylglycerol species containing oleoyl moieties. For example, OOO,
which is the predominant triacylglycerol species of all three adipose
tissues of the HOS group, was not detected in adipose tissues of the
COR group (Table 4)
. Generally, triacylglycerol species containing
linoleoyl moieties were greater in all three adipose tissues of the COR
group, consistent with the fatty acid composition of the
triacylglycerols shown in Table 2
.
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DISCUSSION |
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TOPABSTRACTINTRODUCTIONMATERIALS AND METHODSRESULTSDISCUSSIONREFERENCES |
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). Fatty acid
composition of the diet affects the composition of acyl moieties of
adipose tissue triacylglycerols in many animal species; however, the
asymmetrical stereospecific distribution of saturated and unsaturated
acyl moieties in adipose tissue triacylglycerols is generally retained,
irrespective of the composition and positional distribution of acyl
moieties in the dietary triacylglycerols (Body 1988
).
Under normal (nonfasting) dietary conditions, a major part of adipose
tissue triacylglycerols is derived from triacylglycerols of intestinal
mucosa, which, in turn, result from dietary triacylglycerols via
lipolysis at the sn-1,3 positions in the intestinal lumen
and reacylation of the resulting sn-2 monoacylglycerols in
the intestinal mucosa (Small 1991
). The acylation of
sn-2 monoacylglycerols in intestinal cells is mediated by
two acyltransferases, i.e., monoacylglycerol acyltransferase and
diacylglycerol acyltransferase (Lehner and Kuksis 1996
).
The triacylglycerols of intestinal mucosa are transported to various
tissues, including adipose tissue, via chylomicrons (Small 1991
). During this transport, the triacylglycerols are
partially hydrolyzed by tissue-specific lipoprotein lipases,
resulting in sn-2 monoacylglycerols that are finally
converted to triacylglycerols in the adipose tissues. Alternatively,
the sn-2 monoacylglycerols may also be hydrolyzed, and the
resulting fatty acids may enter the glycerol-3-phosphate pathway, which
finally results in adipose tissue triacylglycerols with a positional
distribution of fatty acids different from that of the dietary
triacylglycerols (Small 1991
). Therefore, the
composition and stereospecific distribution of acyl moieties of mucosal
triacylglycerols and, consequently, of adipose tissue triacylglycerols
are determined, not only by the positional distribution of acyl
moieties in dietary triacylglycerols, but also by the substrate
specificity and stereospecificities of the 2-monoacylglycerol
acyltransferases and 1,2-diacylglycerol acyltransferases in intestine,
chylomicrons and adipose tissues and substrate specificitiy of
lipoprotein lipases. Substrate specificity and stereoselectivity of the
intestinal acyltransferases toward common long-chain acyl-CoA
derivatives and individual mono- and diacylglycerols containing common
long-chain acyl moieties have been investigated extensively
(Lehner and Kuksis 1996
, Small 1991
).
However, little is known about the substrate specificity and
stereoselectivity of the adipose tissue acyltransferases toward less
common long-chain acyl-CoA derivatives; individual mono- and
diacylglycerols containing unusual long-chain acyl moieties,
although certain long-chain fatty acids of less common structure,
such as isomeric cis- and trans-octadecenoic
acids with unusual position of the double bond, have been found to be
extensively incorporated from the dietary triacylglycerols into adipose
tissue triacylglycerols of rats (Emken 1984
, Hoy and Holmer 1981
, Reichwald-Hacker et al. 1979a
).
In this study, we showed that petroselinic acid [18:1(n-12)] from
coriander oil (Table 1)
, an unusual positional isomer of oleic acid
[18:1(n-9)], is extensively incorporated from the dietary
triacylglycerols into adipose tissue triacylglycerols of rats (Tables 2
and 4)
. Predominance of petroselinoyl moieties at the sn-1,3
positions of the adipose tissue triacylglycerols after feeding a diet
containing petroselinic acid–rich coriander oil (Table 3)
suggests
that monoacylglycerol acyltransferases and diacylglycerol
acyltransferases, both in intestine and/or in adipose tissue,
preferentially insert petroselinoyl moieties at the
sn-1(3)positions of sn-2 monoacylglycerols or
sn-1,2(2,3) diacylglycerols. Alternatively,
sn-1,2(2,3) diacylglycerols containing petroselinoyl
moieties at the sn-1(3) positions are the preferred
substrates for the diacylglycerol acyltransferases. In contrast,
linoleoyl [18:2(n-6)] moieties were esterified predominantly to the
sn-2 position (Table 3)
, leading to the formation of high
proportions of PeLPe, OLPe and
palmitoyl-petroselinoyl-linoeoyl-glycerol (PLPe) triacylglycerol
molecular species (Table 4)
.
Oleoyl moieties of the high oleic sunflower oil triacylglycerols (Table 1)
are extensively incorporated into adipose tissue triacylglycerols of
rats (Table 2)
. It is obvious that in all three adipose tissues, fatty
acids are incorporated at the various glycerol positions as it is known
from the literature, i.e., 18:1(n-9) moities are rather evenly
esterified at sn-1,3 and sn-2 positions with
slight preference for the sn-2 position, whereas 18:2(n-6)
moieties were bound preferentially at the sn-2 position
(Table 3)
. This fatty acid pattern is broadly reflected by the
accumulation of OOO and OLO species in all three adipose tissues of the
rats fed the HOS diet (Table 4)
.
Within the two feeding groups, the proportions of several acyl moieties
of triacylglycerols of the three adipose tissues showed minor, yet
significant differences (Table 2)
, whereas the proportions of most of
the acyl moieties at the sn-1(3) positions were not
significantly different (Table 3)
.
Both isomeric octadecenoic acids (petroselinic and oleic acids) were
extensively incorporated into the triacylglycerols of various adipose
tissues, yet the distribution of these monoenoic fatty acids
between the sn-1(3) and sn-2 positions was
distinctly different for the two isomers. Our data do not show
conclusively whether lipolysis of the dietary high petroselinic and
high oleic triacylglycerols by gastric, pancreatic and lipoprotein
lipases followed by reesterification of sn-2
monoacylglycerols or glycerol-3-phosphate pathway, or both pathways,
are involved in the biosynthesis of adipose tissue triacylglycerols,
although the data seem to be more consistent with the synthesis of
adipose tissue triacylglycerols with sn-2 monoacylglycerols
as intermediates. It appears from our data that the acyltransferases
involved in intestinal cells and/or adipose tissues direct 18:1(n-12)
moieties preferentially to the sn-1,3 positions.
Establishment of the substrate specificity and stereoselectivity of the
above acyltransferases toward petroselinic acid and its glycerides
deserves further research, especially in view of the fact that dietary
petroselinic acid, which can be stored extensively in the adipose
tissues, has been found to decrease the level of arachidonic acid in
liver and heart (Weber et al. 1995
and 1997
). It is
conceivable that dietary petroselinic acid, subsequently stored in
adipose tissue, could be utilized beneficially in specific nutritional
states to counteract the overproduction of arachidonic acid and the
resulting increased biosynthesis of eicosanoids such as thromboxane
A2, with undesirable vasoconstrictory properties
(Fischer 1989
).
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FOOTNOTES |
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3 Abbreviations used: COR, rats fed coriander oil; HOS, rats fed high-oleic sunflower oil; OOO, trioleoyl-glycerol;
OLPe, oleoyllinoleoylpetroselinoyl-glycerol; PPePe, palmitoyl-dipetroselinoyl-glycerol; PePePe, tripetroselinoyl-glycerol;
PeLPe, dipetroselinoyl-linoleoyl-glycerol.
4 The composition of the semipurified rat standard
diet was as follows (per kg diet): crude protein, 170.8 g;
disaccharides, 111.4 g; polysaccarides, 151.3 g; crude fiber, 29.9 g; crude ash, 75.8 g; moisture, 53.8 g;
p-amino-benzoic acid, 100.0 mg; biotin, 0.20 mg; choline
chloride, 1.0 mg; folic acid, 10.0 mg; inositol, 111.0 mg; nicotinic
acid, 50.2 mg; pantothenic acid, 50.1 mg; vitamin A, 15,000
IU; thiamin, 20.0 mg; riboflavin, 20.3 mg; vitamin B-6,
15.0 mg; vitamin B-12, 0.04 mg; vitamin C, 20.0 mg; cholecalciferol,
500 IU; vitamin E, 193.6 mg; vitamin K-3, 10.0 mg;
available phosphorus, 7.16 g; calcium, 9.26 g; chlorine,
3.63 g; cobalt, 0.13 mg; copper, 5.5 mg; fluorine, 4.17 mg;
iodine, 0.45 mg; iron, 0.18 g; magnesium, 0.67 g; manganese,
0.10 g; molybdenum, 0.20 mg; potassium, 7.01 g; selenium,
0.32 mg; sodium, 2.44 g; sulfur, 2.0 g; zinc, 28.8 mg. In
addition, the COR diet contained 120 g coriander oil plus 20 g corn oil/kg diet and the HOS diet 120 g high oleic sunflower oil
plus 20 g corn oil/kg diet.
Manuscript received March 29, 1999. Initial review completed May 19, 1999. Revision accepted July 29, 1999.
|
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