- ,, ARCHIVES
FISHERIES AND MARINE SERVICE
Translation Series No. 3832
Distribution and metabolism of odd-numbered fatty acids in domestic animals and poultry - A review
by Haruhisa Ikumo and Minoru Yoshida
Original titl.e: Kachiku. Kakin ni okeru Kisu-Shibosan no Bumpu to sono Taisha
From: Nihon Kakin Gakkai-Shi 12(4): 155-166, 1975
Translated by the Translation Bureau( FRF ) Multilingual Services Division Department of the Secretary of State of Canada
Department of the Environment Fisheries and Marine Service Halifax Laboratory Halifax, N.S.
1976
35 pages typescript DEPARTMENT OF THE SECRETARY OF STATE SECRÉTARIAT D'ÉTAT
TRANSLATION BUREAU BUREAU DES TRADUCTIONS
MULTILINGUAL SERVICES DIVISION DES SERVICES CANADA DIVISION MULTILINGUES
TRANSLATED FROM — TRADUCTION DE INTO — EN Japanese English
AUTHOR — AUTEUR Haruhisa IKUMO and Minoru YOSHIDA
TITLE IN ENGLISH — TITRE ANGLAIS Distribution and Metabolism of Odd-Numbered Fatty Acids in Domestic Animals and Poultry - A Review.
TITLE IN FOREIGN LANGUAGE (TRANSLITERATE FOREIGN CHARACTERS) TITRE EN LANGUE ÉTRANGÉRE (TRANSCRIRE EN CARACTLRES ROMAINS) Kachiku.Kakin ni okéru Kisu-Shibosan no Bumpu to sono Taisha
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, TRANSCRIRE EN CARACTàRES ROMAINS. Nihon Kakin Gakkai Shi
REFERENCE IN ENGLISH — RÉFÉRENCE EN ANGLAIS Journal of Japan Poultry Science
PUBLISHER— ÉDITEUR PAGE NUMBERS IN ORIGINAL DATE OF PUBLICATION NUMÉROS DES PAGES DANS DATE DE PUBLICATION L'ORIGINAL 155-166 YEAR ISSUE NO. VOLUME PLACE OF PUBLICATION ANNÉE NUMÉRD NUMBER OF TYPED PAGES LIEU DE PUBLICATION NOMBRE DE PAGES Japan 12 4 DACTYLOGRAPHIÉES 1975 35
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DISTRIBUTION AND METABOLISM OF ODD- 155 NUMBERED FATTY ACIDS IN DOMESTIC ANIMALS AND POULTRY - A REVIEW
by Haruhisa_Ikumo and Minoru Yoshi.da*
1. INTRODUCTION
Odd-numbered fatty acids, which contain an odd number
of carbons, are widely distributed in the bodies of animals
and plants. The odd-numbered fatty acid content is especially
high in microorganisms, sometimes in excess of 50% of the fatty
acids being odd-nùmbered fatty acids (1). Microorganism
protein is being considered for prospective proteinaceous feeds,
but here, too, fnicroorganism protein contains considerable
amounts of odd-numbered fatty acids. For example, it has been
reported that in hydrocarbon yeasts grown on n-paraffins, 1/3 to
of the fatty acids are odd-numbered fatty acids (2). A
portion of this can be considered to be produced from the
* National. Institute of Animal Industry, Chiba City, Japan.
UNCKIM UhW
■ .1••■••■•■•••••■•••••••••••••••■•••.••••■ •••••••••■•••■■••••••••••••■••••••••••••• * Fatty acids containing 3 carbons are designated as C3 (refer to main text). • -3-
of good quality, they cannot be said to contain objectionable factors. Since both the energy of the yeast itself (4) and the energy of the lipids extracted from the yeast (2,6) are alike well utilized, the odd-numbered fatty acids in hydro- carbon yeasts are well utilized as energy, and are confirmed to have no harmful effects towards chickens. Nevertheless, the widespread recognition that odd-numbered fatty acids are unnatural substances is one reason for the fear that the human body might be adversely affected by feeds made from microorganism proteins. Accordingly, it should be instruct- ive to present a summary of the most recent research results concerning the actual state of odd-numbered fatty acids in the bodies of animals, such as, for example, their distribution, content, composition, and decomposition processes in the living body, and to touch upon the development of feeds from micro- organism proteins, as well as investigations of the possibility of utilizing odd-numbered fatty acids as an energy source in feeds. Taking domestic animal and poultry feeds as the point of departure, the object of this review is to focus on fowl and mammals as well as on their products. The paper does not deal with the wealth of knowledge obtained from the results of research on microorganisms and fish. Fatty acids, which contain a carboxyl group at the end of the carbon chain, are generally indicated by the following structural formula, which shows a saturated n-fatty acid: CH3-(CH2) n-COOH sometimes expressed as R-COOH. Additional types of fatty acids include unsaturated acids, in -4-- which two k hydrogens have been removed and the adjoining carbons form a double bond; oxy-acids, in which one of the hydrogens is replaced with the hydroxyl group (-OH); as well as branched side chain acids in which the carbon chain is not linear. In this report, following the example of propionic acid, the number of carbons contained in the fatty acid is used as its abbreviated name. For example, a saturated fatty acid containing 15 carbons is indicated by C15 or 15:0. For an unsaturated fatty acid, the number of double bonds is included along with the number of carbons, e.g. 15:1. A fatty acid containing a side chain is expressed vither simply as br-C 15 , or in a manner showing the number of the branch-point carbon, such as 13-Me-C 14 (signifying a fatty acid which contains a methyl (Me) side chain on the 13th carbon, for a total of 15 carbons).
2. DISTRIBUTION OF ODD-NUMBERED FATTY ACIDS IN 158 THE BODIES OF DOMESTIC ANIMALS AND POULTRY
The presence of straight-chained odd-numbered fatty acids with more than 10 carbons in the body lipids of domestic animals was first confirmed by Hansen et al (17). However, prior to that, Weitkamp and co-workers (15), who methylated the free fatty acids in human hair and then applied fractional distillation, reported the presence of C7-C17 fatty acids. Hansen et al, after isolating C1 5 fatty acids containing a methyl side chain (12-Me-C 14 and 13-Me-C 14 ) from hydrogenated mutton tallow (19), reported the isolation of C 17 fatty acids. The lipid was hydrolyzed, methylated, fractionally distilled under reduced pressure, and crystallized. From melting points, measurement of saponification values, x-ray diffraction, elemental -S- analysis, etc. they established that it was an odd-numbered fatty acid and not an equivalent mixture of two kinds of even- numbered fatty acids.
With the establishment of gas chromatography techniques, research on the distribution of fatty acids in living bodies rapidly progressed. Even in Japan, it was at once applied to the analysis of the fatty acid composition of butter and cheese (20).
The distribution of straight-chained fatty acids in the bodies of domestic animals and poultry, as well as in their products, is summarized in Table 1. This table, which is roughly classified according to body lipids, meat, milk, phospho- lipids, glycolipids, brain lipids, and oxy-acids, also indicates the proportions of odd-numbered fatty acids contained in the total fatty acids, and is intended as an aid in understanding the gist of the distribution of odd-numbered fatty acids.
Odd-numbered fatty acids were first confirmed to be released from the body lipids of ruminating domestic animals, but their existence also has been observed in humans and chickens. Odd-numbered fatty acids also have been observed to be widely distributed in the meat and milk of various animals; they have also been detected in human milk. The distribution of odd-numbered fatty acids in the meats indicated in Table 1 is the distribution in neutral lipids; however, there are many reports investigating the fatty acid composition of the phospholipids extracted at the same time (27, 35-38). The distribution of odd-numbered fatty acids in phospholipids closely resembles that in neutral lipids, but, although not shown in
Table 1, it has been observed that the odd-numbered fatty acid 0 < -6-
content in phospholipids tends to be higher than in neutral
lipids. Table 1 shows Gray's study (41) on phospholipids for
the lecithin fatty acid composition. In addition to this, Gray
studied the fatty acid composition for choline plasmalogen,
kephalin, and kephalin plasmalogen. The fatty acid compositions
for these were similar to that for lecithin, but the content
tended to be less than that in lecithin. These indications
are omitted from Table 1. From these phospholipid fatty acid
compositions, particularly noteworthy is the high C171 acid
content in sheep's semen: lecithin 16.2%. and choline plasmalo-
gen 10.1%. The C17:2 acid content was also fairly high, at 4.3%
and 2.2%, respectively. As Gray points out, as studies are
made with increasing numbers of measurements and different
types of domestic animals, it will be necessary to confirm
whether or not it can be said that these are the usual phospho-
lipid components of semen.
Odd-numbered fatty acids also have been observed in the
phospholipids contained in human red blood cells (42). In
addition, odd-numbered fatty acids have been detected in the
fatty acid make-up of human blood (48), the red blood cells
of children (49), and human liver (50). Since the original
reports were not available, these data are not shown in Table 1.
Odd-numbered fatty acids have also been reported to be in the
blood, liver, and bile of rats (51) as well as in cow's milk (52).
Glycolipids characteristically contrast with phospholipids
in that they contain higher (greater than C21) fatty acids. A
similar tendency, only stronger, has also been observed in the
fatty acid composition of brain lipids, C23 and C25 content in -7- particular being high, with examples known to contain in excess of 10%. Although not tabulated here, characteristic quantities of C27 acids have also been detected (45). Furthermore, these fatty acid compositions are characterized by the presence of oxy-fatty acids, which also appear to be of high C23 and 025 However, it has also been reported that odd-numbered content. fatty acids were not observed in the glycerophospholipid fatty acids of the human brain (53). The long chain odd-numbered fatty acids found in the brain are not derived from the odd- numbered fatty a.cids in plants. In the first place, it is known that these kinds of long chained fatty acids are rarely digested and assimilated; the majority are believed to be produced within the human body. As stated later, it is believed that long chained odd-numbered fatty acids are produced from long chained even-numbered fatty acids undergoing oxylation, then decarboxyl- ation viao(-oxidation. Although not mentioned in Table 1, numerous reports also have been published concerning odd-numbered fatty acids containing side chains. As stated earlier, the odd-numbered fatty acids first isolated from mutton tallow by Hansen and co-workers were not straight chained n-fatty acids, but rather 12-Me-C 14 and 13-Me-C 14 acids (19). Later, the separation of side-chain-contain- ing odd-numbered fatty acids from butter fat was also confirmed (30,31,54). Afterwards, with the development of gas chromatog- raphy, it was shown also that side-chain- containing fatty acids, which have been widely detected in human body lipids (29), beef (36), cow's milk (40), as well as in the phospholipids of • -8- various domestic animals (41), etc., were not unique, but rather could be considered as normally existing components. Finally, we would mention that fatty acids are easily obtained from aldehydes, which, although not fatty acids, are compounds which closely resemble fatty acids. According to Gray (41), the distribution of odd-numbered aldehydes contained in the plasmalogen of cows, pigs, and sheep is as shown in Table 2. Note that 015 aldehydes, particularly 015 aldehydes containing side chains, are abundant, reaching as high as 35%. The physiological significance of this will no doubt be the subject of future research; however, it is noteworthy that in the aldehydes which are substances closely related to fatty acids, those containing an odd number of carbons are present overall in large quantities in excess of 40%. 159
3. BIOSYNTHESIS OF ODD-NUMBERED FATTY ACIDS.
3-1 Mechanism of Fatty Acid Biosynthesis
The mechanism of the biosynthesis of fatty acids was elucidated by Lipmann, Wakil, and Lynen in the first half of the nineteen-sixties. The mechanism of the biosynthesis of fatty acids is briefly indicated in Figure 1. Malonyl Co-A (C unit) is indispensable to the biosynthesis of fatty acids. 3 Acetyl Co-A (C 2 unit), a fundamental substance of energy metabolism in nature, is converted to malonyl Co-A through a Co-A carboxyrase. The CO2 fixation reaction caused by acetyl mechanism of the biosynthesis of fatty acids is one in which a long chained fatty acid is produced with acetyl Co-A (C 2 unit) as primer (reaction initiator), accompanied by the decarboxylation action, a reduction reaction (via NADPH), of malonyl Co-A; through the successive additions of C2 units of the latter
the carbon chain grows. When acetyl Co-A (C2 unit) is the primer,
an even-numbered fatty acid results. This is the usual
mechanism for the biosynthesis of fatty acids.
3-2. The Biosynthesis of Odd-Numbered Fatty Acids
However, since Fatty Acid Synthetase, which mediates the
biosynthesis reaction for fatty acids, is characterized by
a wide range of specificity, the reaction can proceed even
with acyl Co-A (usually R-CO-S-Cô-A) as primer (reaction initiator),
as well as with the C2 acetyl Co-A (55). Thus, when the primer
is propionyl Co-A, a C3 compound, through the decarboxylation
reaction with malonyl Co-A (C3) the carbon chain grows by the
successive addition of C2, finally producing a long chain odd-
numbered fatty acid. Propionyl Co-A (C3) is produced directly from propionic
acid (see Figure 4) as well as from branched amino acids such
as isoleucine and valine (see Figure 2). In addition, it is
known to be produced also from threonine. Actually, it has
been proved by a large number of experiments that odd-numbered
fatty acids are produced in living bodies from propionyl Co-A.
Thus, it has been proved that odd-numbered fatty acids are
produced from propionic acid in the mammary glands and liver 160 (in vivo) of rats (Katz et al (56)), in the fatty tissues of
rats and mice (in vivo, in vitro) (Farvargar et al (S7), Nasoro
et al (58)), and in the liver and fatty tissues (slices) of
rats (Fell.er et al (59)). In addition, it has been reported -10- that when 14C-tagged propionic acid was injected into the udders of cows, 14 C-labelled odd-numbered fatty acids were detected in the butter fats, the uptake by Cl'ï, C13, and C15 in particular being great (60).
Figure 2 shows the decomposition path for amino acids having branched carbon chains; that is, branched amino acids
(valine, isoleucine, leucine). These branched amino acids are transformed into acetyl Co-A, propionyl Co-A, succinyl Co-A, etc. and become energy sources, but in the courst of the decomposition process branched acyl Co-A s such as isobutyric acid Co-A (from'valine),o(-methyl butyric acid Co-A (from isoleucine), and isovaleryl Co-A (from leucine) are produced.
When these kinds of branched acyl acids take the place of acetyl Co-A as reaction initiators in the fatty acid biosynthesis mechanism shown in Figure 1, long chained branched fatty acids are produced through the addition of malonyl Co-A. Branched
fatty acids containing both odd and even numbers of carbon
are produced, depending on the corresponding branched amino
acids (61). In fact, Grigor et al (61) reported that, by
adding valine, isoleucine, and leucine to the feed of rats,
increased amounts of branched fatty acids were detected in the
rats' skins; furthermore, when 14C was used, the 14 C in these
amino acids became incorporated in the branched fatty acids in
the skin. Also, it is known that branched fatty acids,
especially C15"4C17 branched fatty acids, are abundant in the
lipids contained in the fecal matter of mammals (62). -11-
This, according to Grigor et al (62), originates from the utilization of branched amino acids by intestinal bacteria, so that branched fatty acids produced in the intestines are natural, and would probably be absorbed by the body of the animal.
4. DECOn.TOSITION OF FATTY ACIDS
4-1 Oxidation 7echanisms of Fatty Acids
As a rule, three types of mechanism are known for the oxidation of fatty acids; (1) 0C-oxidation, (2) /3-oxidation, and (3)0â -oxidation. Among these, the most important to nutritional science and the most well-known is -oxidation. The acetyl Co-A (02 unit) produced via this mechanism is a fundamental substance in energy metabolism. On the other hand, c -oxidation and o.›-oxidation take place under particular conditions and can be said to be special mechanisms. These mechanisms are briefly shown in Figure 3. In p -oxidation, the /3 -carbon (methylene group) undergoes oxidation, producing a new carboxyl group (-COOH) and at the same time releasing a C 2 unit (acetyl Co-A). That is, 02 portions are successively severed from the carboxyl group side of the fatty acid. The acetyl Co-A is, of course, further decomposed to carbon dioxide and water in the TCA cycle. The • -oxidation mechanism is one in which the c( -position of the fatty acid is oxidized, producing a new carboxyl group and concomitantly releasing 002 . When the d..-position is oxidized, J,.-hydroxy acid (oxy-acid) is produced; subsequently -12- the carbon from the carboxyl group breaks away as C02. According-
ly, if an even-numbered fatty acid ündergoes c{ -oxidation, an
odd-numbered fatty acid is produced. The presence of C21 - C2S
high odd-numbered fatty acids has been reported in the brains
of animals (63,64,65) and in some plants (66,67,68), but these
are produced through 4 -oxidation. In the C,)-oxidation
mechanism, the end group on the side opposite to the carboxyl
group (-COOH) is oxidized. To cite an example, this is said to
occur in the middle of the decomposition path of cholesterol.
4-2 OxidationNechanisms of Odd-Numbered Fatty Acids
4-2-1 Metabolic Path of Propionic Acid, Propionyl Co-A
0 2 units are successively severed from the carboxyl group
side of even-numbered fatty acids through fi -oxidation, and the
C2 units become energy sources by decomposition in the TCA
cycle to water and carbon dioxide. That is, there is complete
conversion to C2 units. On the other hand, C2 units are also
severed from odd-numbered fatty acids by P -oxidation, but
in the end a C3 unit propionyl Co-A is produced. Figure 4 shows the propionic acid/propionyl Co-A metabolic
reaction path. The existence of this path has been.confirmed in animal tissue by Katz and Chaikoff (69) and Flavin and
Ochoa (70). Propionyl Co-A is converted to C4 methyl malonyl Co-A through a carbon dioxide fixation reaction via the biotin
enzyme propionyl Co-A carboxyrase. Using vitamin B12 as a isomerization reaction, co-enzyme, methyl malonyl Co-A, through an is converted to succinyl Co-A, which is an intermediate -13- metabolite in the TCA cycle. Accordingly, both propionic acid as well as propionyl Co-A ultimately are oxidized in the
TCA cycle. Incidentally, as a special characteristic of odd-numbered
fatty acids, it can be mentioned that they are glucogenic
(sugar abiogenic, glucose producing). This is because the
propionic acid produced from an odd-numbered fatty acid is
converted to the TCA cycle intermediate metabolite, succinyl
Co-A, via the metabolism path in Figure 4. This sugar-producing
ability of odd-numbered fatty acids was substantiated by the
experiments of Van Itallie et al (71), who caused odd-numbered
fatty acids to accumulate in the fatty tissues of rats, and
found that even if the rats were put into a state of starvation
that the blood sugar values and the amounts of liver glycogen
and muscle glycogen were not easily lowered. This is in great
contrast to the ketogenic (ketone body producing) property
of even-numbered fatty acids.
4-2-2 The Relation Between Vitamin Bi2 and Odd-Numbered Fatty Acids
It has been reported that when large amounts of propionic
acid or odd-numbered fatty acids are given to non-ruminant
animals, the vitamin B12 demand increases. According to
Dryden et al (72), when C1-C10 fatty acids were given to rats,
if the fatty acid was odd-numbered, depending on the rearing
conditions, vitamin B12 deficiency disease occurred; moreover,
the animals recovered when vitamin B12 was added to their feed.
Furthermore, increased vitamin B 12 demand brought about by -14- supplying propionic acid (C 3 ) has been reported in rats (72,73, 74) and chicks (74). The reason why vitamin B12 deficiency disease results from the administration of quantities of propionic acid or odd-numbered fatty acids is believed to be as follows: namely, that in the metabolism path of propionic acid, shown in Figure 4, 162 vitamin B 12' being required as a co-enzyme in the polymerization reaction from methyl malonyl Co-A to succinyl Co-A, is consumed in this reaction. In rats (76,77) and humans (78) it has been reported that, because of this reaction, when there is a deficiency of vitamin B12 (due to propionic acid), either methyl malonyl Co-A accumulates, becomes methyl malonic acid, and the amount of methyl malonic acid discharged in the urine increases, or, methy malonyl Co-A reverts to propionyl Co-A and the odd-numbered fatty acids in the body tissues increase.
The vitamin B12 deficiency phenomenon occurs from furnishing high protein feeds as well as from adding large amounts of individual amino acids to feeds. For example, according to Dryden (72), who fed rats with 25% proteinaceous feed to which were added large amounts of individual amino acids, the addition the vitamin B12 deficiency phenomenon occurred with of valine, isoleucine, and threonine. As stated in section 3-2 (refer to Figures 2 and 4), these amino acids produce propionyl Co-A in the metabolic process. Consequently, vitamin B12 is consumed in the reaction from methyl malonyl Co-A to succinyl Co-A. Similarly, in experiments in which hydrocarbon yeasts were fed to chickens, low hatching rates due to dead eggs were -1 5- observed in the case of breeding chickens (79,80), while the phenomenon of growth suppression was observed in the case of broilers (8). Since both of these phenomena are due to vitamin B12 deficiency, the precaution is taken of providing vitamin B12 by injection or by addition to the feed. The vitamin B12 deficiency is believed to have resulted on account of the vitamin B12 content of the hydrocarbon yeast at the start of the experiment being less than was assumed (79). However, since hydrocarbon yeasts have a high odd-numbered fatty acid content, the chickens will metabolize the odd-numbered fatty acids, and in order to utilize them effectively, large amounts of vitamin B12 are necessary, so that this too can be considered as promoting vitamin B12 deficiency. As stated in section 1, the fatty acid composition of yeasts is not determined only by the culturing conditions, but also is related to the character- istics of the yeast itself, and it is a fact that hydrocarbon-fed yeasts contain a high odd-numbered fatty acid content (2).
5. METABOLISM OF ODD-NUMBERED FATTY ACIDS IN LIVING BODIES
5-1 Hydrolysis, Absorption, and Transport of Odd-Numbered Fatty Acids in the Intestines
In the small intestine the tri -glycerides (neutral lipids) of fatty acids undergo hydrolyzing action from lipase, hydrolyzing to monoglycerides and free fatty acids, which are absorbed from the intestinal walls. After absorption, there are two transport routes, depending on the number of carbons in the length of the fatty acid. In general, regardless of whether there is an odd or even number of carbons, acids lower than C10 capric acid pass through the portal vein in the form of hydrophilic free acids and are transported to the liver (81). Hashim as well as Campbell
et al carried out a series of researches concerning the mechan-
isms of hydrolysis, absorption, and transport of odd-numbered
fatty acids. According to the experiments of Hashim et al (82)
on dogs and rats, in which triglycerides of C9 straight-chain fatty acids
(n-nonanoic acid or pelargonic acid) were employed, namely
tri-pelargonin (referred to below as Tri-C9 ), after the
Tri-C9 has undergone the hydrolyzing action of lipase in the
small intestine, most of it (more than 95%) is transported in
the free form to the liver via the portal vein. As for the other
route, through the lymphatic vessels, it was found that when
lymphatic vessel lipids were analyzed, C9 acids were hardly
detected. In the matter of transport routes, C9 acids were similar to C8 acids and C10 acids (81,83). On the other hand, the case of straight-chain odd-nLmlbe.red. Cll acids
(n-undecanoic acid) differs from C9 acids. According to Lineres
(84) and Campbell (81), in rats, after the triglycerides of
C11 acids, namely tri-undecanoin, undergo hydrolysis by lipase
in the small intestine, the portion going by way of the portal
vein is separate from that going by way of the lymphatic
vessels. Furthermore, the fraction going each way is said to
be half. When one considers that for C12 lauric acid almost
all is transported to the liver in the form of free fatty acid
via the portal vein (85), the fact that C11 undecanoic acid
which contains one carbon less than lauric acid passes via the
lymphatic vessels can be said to be a peculiarity of odd-numbered
fatty acids. Although no reports have been found concerning -17- odd-numbered fatty acids greater than C13, presumably the major proportion would be transported via the lymphatic vessels, enter the blood, and be distributed in the body.
In general it is said that after absorption in the intestinal tract C 16 and C18 even-numbered fatty acids are re-synthesized as triglycerides, pass chiefly through the lymphatic vessels, transported in the form of chylomicrons
(protein complexes), enter the blood, and are distributed in the body; although it is the case that approximately half of C11 undecanoic acid as well is transported via the lymphatic vessels following absorption in the intestinal tract.
5-2 Accumulation of Odd-Numbered Fatty Acids in Tissue and Their Passage In and Out of Tissue
As stated earlier, regardless of their being even or odd-numbered, since acids lower than C10 capric acid as well as C12 laurie acid pass through the portal vein as hydrophilic free fatty acids and are directly transported to the liver where they are rapidly metabolized, even when these acids are supplied to animals there is almost no accumulation in the
tissues (81,86). Because a portion of Cl4 myristic acid passes
through the lymphatic vessels a small amount accumulates in
the fatty tissues (81). Usually C 16 and C18 acids are the principal ones found in the fatty tissues of animals, but,
as these are largely influenced by the feeding conditions,
the fatty acid constituents in the fatty tissues reflect those
found in the feed (87).
On account of the fact that vdd-numb-ered fatty acids . . -18-
below 0 are directly transported via passage through the 9 portal vein to the liver where they are rapidly metabolized they do not accumulate in the tissues (86); however, if large in the fatty amounts of C 11 are supplied it will accumulate tissues. As stated earlier, for C ll undecanoic acid it has been reported (81,84) that half passes through the portal vein and half through the lymphatic vessels, and that it is the latter portion passing through the lymphatic vessels which accumulates in the fatty tissues. When dogs are supplied with feed containing 10% triglyceride of undecanoic acid, 0 11 rapidly appears in the fatty tissues and reaches a peak after 4 weeks (81). In rats supplied with tri-undecanoin as well, fatty tissues reaches the amount of C 11 acid accumulated in the a peak in about 3 weeks after being supplied (88,89). Thus, for the above, it was reported that the C ll acid content of the fatty acids found in the fatty tissues was 20% for dogs (81) and 35% for rats (88) when the lipid contents of the respective feeds were 50% and 70% tri-undecanoin, respectively. In this way then, large amounts of C ll undecanoic acid accumulate in fatty tissue to be consumed as energy sources, but there is hardly any accumulation at all in tissues other than fatty tissue (81). When tri-undecanoin (81) and tri-valerin (valeric acid C triglyceride) (90) are furnished, odd-numbered 5 fatty acids greater than C 13 are found in tissue other than fatty tissues, namely, in the liver, red blood cells, and blood serum lipids (triglycerides, phospholipids), but are most abundant in the liver. Furthermore, for this case, the odd-numbered fatty acids higher than 013 are mainly C 15 , C17, and C19. In addition, the odd-numbered fatty acids C13:0' C15:0'
C15,1, C17s0, and C17;1 are also found in fatty tissue. These
facts suggest that the acids above C13 are being biosynthesized
from the C5 and C11 acids.
Campbell et al (88) have reported as follows, concerning
the entry and exit of large amounts of accumulated C11
(undecanoic acid) to and from fatty tissues: Even after rats which have had C11 acid accumulated in their fatty tissues get
used to the starved condition, the relative C11 content of the
fatty acids contained in the fatty tissues does not change.
From this fact it is believed that the C11 acid enters and
exits to and from fatty tissue at the same velocity as the
other fatty acids. Accordingly it has been reported that the
form in which entry and exit to and from fatty tissue is made
is not as triglyceride, but principally as free fatty acid, so
that the C11 acid is transported as free fatty acid from the
fatty tissues to the liver, where it is oxidized to C02.
Furthermore, it has been reported by Campbell (81) that the
turnover rate for C11 acid in rats does not differ from that for
linolic acid (C18:2).
Next, Witter et al (91) injected triglycerides synthesized
from C41 C81 C99 C10' C12' C14 , and C16 saturated fatty acids
into the veins of sows and studied the changes in the patterns
of fatty acids in the blood plasma and milk after six hours.
They reported that initially there were almost no C4-C12
acids in the pigs' blood plasma and milk; six hours after
injection C4 and C8 had not appeared in the blood plasma, but
C9 (n-nonanoic acid), C10, and C12 acids had reached 2-4% of the constituent fatty acids. C14 and C16 had reached 32.1%
(2.1%) and 45.6% (26.5%) respectively ( the numbers in the
brackets refer to the usual conditions). They go on to
report that i n the milk, C4 did not appear while C8, C9, and
C10 were 1.0-1.7ô and C12 was 4%; on the other hand, C14
and C16 had increased to 14.4% (3.0%) and 39.5% (26.2I)p respectively ( the numbers in the brackets refer to the usual
conditions). From this report it is seen that acids up to
C4-C12 are metabolized at a fast rate (i n the.:liver they are
rapidly oxidized to C02), hence do not readily appear in the
milk. C9 acids are similar to C8 and C10 acids with respect
to metabolic rate. In addition, Boyer ( 92) has reported that
the metabolic rate i n the liver for C17 hepta-decanoic acid
(also called margaric acid) i s the same as that for C16
palmitic acid ( in vitro).
5-3 Concerning the Influence Exerted on the Bodies of.Animals by Giving Them Odd-Numbered Fatty Acids, and Toxicity
In most of the past experimental work in which odd-
numbered fatty acids were given to animals, the fatty acids
were•given as triglycerides. The instances in which they have been-administered as free acids are few (93,94,95)• the primary reason probably being the poor taste (95). In addition, if the lower fatty acids are given as such, since a portion would evaporate, it is certain that special means for supplying them would be required. Furthermore, there is the difficulty that supplying lower fatty acids to animals by force has been known to cause dea-th (94).
As stated before, in living bodies.odd-numbered fatty -21- acids undergo p -oxidation in the same manner as even- numbered fatty acids, with the severing of 02 units, with a C unit (propionyl Co-A) shown in 3 being finally produced. As 4-2-1, supplying odd-numbered fatty acids to animals results in an increase of the amounts of vitamin B12 required, since vitamin B12 is consumed in the process of metabolizing propionyl Co-A. Accordingly, if the vitamin B12 content of the feed is not adequately taken into account, there exists the danger of incurring vitamin B12 deficiency disease. Even is amply supplied, in cases in which vitamin B12 the influence exerted on the bodies of animals by supplying odd-numbered fatty acids can differ greatly with the odd- numbered fatty acid content in the feed, or the fraction in the feed lipids, etc. For C ll triglycerides, namely tri- undecanoin (abbreviated to Tri-C11)' it has been reported (81) that the growth of dogs over 36 weeks was normal when Tri-C11 comprised 50% of the feed lipids (the remaining 50% being cotton seed oil), with the overall lipid content of the feed being 20%; similarly it has been reported (88) that there were no abnormalities in the growth of rats when Tri-C 11 comprised 70e of the feed lipids (the remaining 30% being corn oil), with a feed fatty acid content of 30%. Furthermore, Van Itallie et al (71) reported that when Tri-C 11 was made to comprise 90% of the lipids in the feed (the remaining 10% being corn oil), the amount of feed ingested by rats was slightly lower than the 100% corn oil control but that growth was normal. In addition, it has also been reported (89) that when rats were given Tri-C 11 and corn oil lipid mixtures • • -22-
(30% of feed content) of varying proportions, the Tri-C 11 was utilized up to a Tri-C li scorn oil ratio of 95:5. However, Mohrhauser et al (90), using feeds in which the total lipids consisted of tri-valerin ( 0 acid) and Tri-C 11 5 (lipid content was 30% of the feed), have reported that when only the required amount of linolic acid was orally administered 164 daily to rats, the growth of the rats was very poor. Further- more, the data of Yoshida et al (94) showed that when C3-C11 odd-numbered fatty acids were fed to chicks as free acids (5% of the feed), the utilizability was poor for 0 (propionic 3 acid) and C (valeric acid), but good for C , C , and C . 5 7 9 11 In rats, however, propionic acid is said to be well utilized (93). In addition, in the experiments of Witter et al (91) in which
04-016 triglycerides synthesized from the fatty acids were injected into the veins of sows, although the sows became feverish with increased respiration rates with 04 butyric acid, normalcy was reported with the other fatty acids, including
9' From reports such as above, it can be said that when odd-numbered fatty acids below C il are given, as long as attent- ion is paid to the vitamin B12 content of the feed and the acids are mixed with natural oils, the energy of the odd- numbered fatty acids is efficiently utilized. However, the poor utilization rate of 0 (propionic acid) and cause of the 3 C (valeric acid) in chicks is not understood. Moreover, 5 since examples were not found in which odd-numbered fatty acids above 016 were given, this would appear to be an area for investigation*.
6. CONCLUSIONS
During the period before the development of techniques for the discrimination, characterization, and determination of fatty acids, naturally-occurring odd-numbered fatty acids were believed not to exist, whereas, in reality, although their amounts relative to even-numbered fatty acids are small, they
are widely distributed and can be considered as normal components
in the bodies of livestock and poultry. Both the linear carbon
chain and branched side chain types can be said to be common.
Although, as set forth in the opening paragraph, the subject
of this review has been limited to poultry (birds) and livestock
(mammals) and has not touched upon other animals, odd-numbered
fatty acids have also been observed to be widely distributed
in fishes, microorganisms, and the plant world. Most of this
knowledge has been obtained within the past 20 years, in
particular within the past 15 years during which the techniques
of gas chromatography have been established.
Until now, it was believed that odd-numbered fatty acids
found in the bodies of fish and domestic animals were derived
from odd-numbered fatty acids which were produced by micro-
organisms in the intestines or microorganisms ingested with
s'6-les of experiments carried out by KO and TASAKI (Nagoya University) in which C17 acid was given to chicks has been described briefly in an outline address given at the 1972-1974 meeting of the Japan Animal Husbandry Society (NihonChikusan Gakkai). -24- the feed. Since these animals have lumens, this was similar to the way in which ruminating livestock characteristically are able to effectively utilize non-protein nitrogen compounds by making practical use of these microorganisms. However, from comparisons of the constituents of the body lipids and milk lipids of various domestic animals, as well as from the existence of higher odd-numbered fatty acids in the brain, etc., it can be said that the odd-numbered fatty acids do not derive merely from the feed or from microorganisms in the intestines, but also must include some odd-numbered fatty acid produced within the body of the animal. This indicates that the odd-numbered fatty acids present in living bodies are by no means unnatural, but that they are produced in the bodies of animals and plants as well as in microorganisms, and are normal components which undergo metabolization. Reports of research carried out from the nutritional standpoint on the rate of digestion and energy utilization etc. of odd-numbered fatty acids are unexpectedly few, but for domestic animals and poultry the energy is well utilized, and in this respect, is probably the same as for even-numbered fatty acids. The metabolism and biosynthesis of both even- numbered and odd-numbered fatty acids in living bodies have been fairly well elucidated. Being the same fatty acids, the mechanism of biosynthesis and the mode of metabolization are eiactly the saine, but, because of the difference owing to whether the number of carbons is even or odd the final products of metabolism, although being close, will differ (namely, acetyl Co-A or propionyl Co-A). On account of this, odd-numbered -25- fatty acids have the peculiarity of requiring vitamin B12.
As described at the outset, the motive for investigating the dynamics of odd-numbered fatty acids in the'-living body was foremost connected with the problem of making feeds from microorganism proteins, and was to make clear any influence which odd-numbered fatty acids contained in the microorganisms might exert on domestic animals, poultry, and livestock products.
The information thus far elucidated still cannot be said to be sufficient; however, from this knowledge it can probably be stated that in the case of utilizing microorganisms as feed, the inclusion of odd-numbered fatty acids in itself presents no particular cause for concern.
From the dietetic standpoint it will be necessary to consider carefully the influence on domestic animals and poultry of supplying them with odd-numbered fatty-acids in
large quantities and over long periods of time. A series of researches (3-16) in which hydrocarbon yeasts were given to
chickens can be cited by way of example. In these animal
experiments odd-numbered fatty acids derived from the yeasts
comprised 0.3 - 0.5% of the feed. Also, in similar successive
breeding experiments with rainbow trout (96) and mice (97) the
odd-numbered fatty acids were believed to comprise from 1-5%
of the feed. From the fact that no particularly bad effects
were observed in using these feeds it can probably be stated
that both odd-numbered and even-numbered fatty acids are
utilized equally well. As mentioned in the first section, in experiments in which only the lipids were extracted from yeasts and given to chickens (6) and rats (2), the energy of the mainly C C 17 odd-numbered fatty acids contained in the lipids was efficiently utilized by the chickens and rats. Without question the fatty acids Contained in yeasts and the like can be assumed to be digested by domestic animals and poultry, absorbed in their bodies, and utilized as energy to the limit of their oxidation, regardless of whether the number of carbons is even or odd. Exclusive of the animal experiments involving hydrocarbon yeasts, no past examples of experiments are to be found in which odd-numbered fatty acids greater than C 13 were supplied. The reason for this may be the difficulty in obtaining large quanti±ies of samples or the lack of necessity, but there is room here_for investigation, concerning the effects of feeding animals large quantities of C13-C17 odd-numbered fatty acids. concerned, there is probably As far as acids greater than C 19 are no need to call this matter into question in the first place since acids greater than C 18 , exclusive of unsaturated acids, are not readily absorbed in the bodies of domestic animals and poultry (94). In addition, if odd-numbered fatty acids in the living body are to play a special role in the future, there will be a need to study just what kind of role they are to play. -27-
REFERENCES CITED
(2) YOKUYAT"A Suiei, KANEDA Naoji, Abura Kagaku (Oil Chemistry), 21, 900, 1972.
(3) NISHIKA19A Tetsusaburo, TANAKA Tsuneo, YAMANE Tetsuo, HONDA Hironobu, Nitchiku Kaiho (Bulletin of the Japan Livestock Association), 41, 569t 1970.
(4) KOSAKI Kiyomi, HOSHII Hiroshi, YOSHIDA Minoru, Kakin Kaishi (J. of the Japan Poultry Assoc.), 9, 159# 1972.
(5) YOSHIDA Minoru, TADA Masao, BANSHO Hiroyuki, MATSUSHIMA Masahiro, OGATA Kuniyuki, INO Masao, UMEDA Isao, ibid, 9, 173, 1972. (6) YOSHIDA Minoru, IKUGUMO Haruhisa, HOSHII Hiroshi, ibid, 9, 231, 1972. (7) YOSHIDA Minoru, TADA Masao, BANSHO Hiroyuki, MATSUSHIMA Masahiro, KINIWA Kenji, INO Masao, UMEDA Isao, ibid, 10, 63, 1973.
(8) TADA Masao, FURUICHI Hideji, IMOO Fumio, BANSHO Hiroyuki, YAMANAKA Kei z o, IWASE Nobuo, YAHATA Sakuro, ibid, 10, 939 1973.
(9) IMOO Fumio, TADA Masao, IWAMOTO Toshio, MURATA Takehisa, KAWASAKI Akira, ibid, 10, 189, 1973.
(13) YOSHIDA iv`inoru, TADA Masao, BANSOH Hiroyuki, MATSUSHIMA Masahiro, UMEDA Isao, Kakin Kaishi , 11, 217, 1974.
(20) KAWASHIRO Takashi, TANABE Hiroya, ISHI Akio, Shokuhin Eiseigaku Zasshi (J. of Food Hygiene), 1, 78, 1960.
(79) TADA Masao, IMOO Fumio, MURATA Takehisa, KAWASAKI Akira, Kakin Kaishi, 9, 17t 1972.
(80) TADA Masao, ibid, 11, 223, 1974.
(96) TAKEUCHI Masaaki, personal communication.
(97) YAMADA Yukio, personal communication. • •p• , " r ", • ;
-28-
Ye.
• 'J.; M : 1Z -rj • Wei 1)• iiii1eili)14re", fk.a 165
.';i5:1; f#11:11-kil2 et, 35, 1434, 1957. 25) HANSEN, R. P., F. B. SHORLAND and N. J. COOKE: iiit 01) 4)"."2 fifJ:11-Dr:1- es 3Mte.c75,-;3 5 . Nature, 176, 882, 1955. t 26) TISCORNIA, E.: Atti Accad. Ligure Sci. Lettere, E0) 5 %:01/J 21, 321, 1961. 27) . KATZ, M. A., L. R. DUGAN, Jr., and L.E. DAwsos: J. Food Sc.. 31, 717, 1966. 28) SCHULER, G.A. and E. O. ESSARY: 'bid, 36, 431, 1971.
1) SCHLENK. H.: Fed. Proc., 31, 1430, 1972. 29) JAcog, J. and G. GRIMNIER: J. Lipid Res., 8, 303, 2) IRO; • :fk- rt-411;C:iimbre, 21, 900, 1972. 1967. 3) iles111 4,f11115 • 111 11 1 1,UP. • 111111,e); • 30) SHORLAND, t. B., T. GeesoN and R. P. HANSEN: iA.M, 41, 569, 1970. Biochem. J., 59, 350, 1955. 4) E • RAI: f • Vi 111 1.ezen-m, 9, 31) SHORLAND, F. B., T. GERSON and R. P. HANSEN: 159, 1972. . Ibid., 61. 702, 1955. 8 ) ïFi• 1, r3 53 • ifiK.'efl • es.taie-iri75- 32) HANSEN, R. P., F. B. SHORLAND and N. J. CooRe: •• 1-5;'2:. HI, 9, 173, 1972. Nature, 179, 98, 1957. d ) • flr.. • 11.11: FLE, 9, 23 1 , 33) HANSEN, R. P., F. B. SHORLAND and N. J. COOKE: 1972. New Zealand J. Sci., 6, 101, 1963. GRUGER, C. LEONG and 7) 1.!i*R1 •emcun • -eive.'4_: 1-Y • egi Ere • lz 34) MILLER, D., E. H. Jr., K. • fgaiiiik9;: • 11,119 F;,11: Fill, 10, 63,1973. G. M. KNOBL, Jr.: J. Food Sci., 32,3-12, 1967. pnJ1 •i 35) ALLEN, BRAY CASSENS: . • 8) l-rili11:7:«RI • v..ff. • eflri:V.Zi-1 • t1/ E., R. W. and R. G. Ibid. rill:•*zE1. • niffifiU • A t'à ife: • 10, 93 1973. 32, 26, 1967. 9) 117.;U*, • ern:71 ; • ed,:ânt. • 11- 111WA. • lei 36) (ti' KEEFE, P. W., G. H. WELLINGTON, L. R. MAT • N.,: VI I:, 10, 189, 1973. TICK and- J. R. STOUFFER: Ibid., 33, 188, 1968. 10) 'YOSHIDA, NI.TADA, H. BANSHO, M. .MATSUSHI - 37) TERRELL, R. N., G. G. Suess, R. G. CASSENS and MA, K. Kon, M. IINO and I. UMEDA: Japan. R. W. BR.AY : Ibid., 33, 562, 1968. Poultry Sc., 11, 163, 1974. 38) HORNSTEIN, I. and P.P. Ceowe: Ibid., 32, 650, 11) YOSHIDA, M., M. TODA, H. BANSHO, M. MATSUSHI - 1967. MA, K. Km, NI.IINo and I. UMEDA: Ibid.. 11, 39) BRECKENRIDGE, W.C. and A. KUESIS: J. Lipid 179, 1974. Res., 8, 473, 1967. 12) YOSHIDA, M.: Ibid., 194, 1974. 40) HERB, S. F., P. MAGIDMAN, F. E. LtDDY and R.W, 13) Ili • '..`.e111 93 • '1'2 fi • • RIEMENSCHNEIDER: J. Am. oil Chem. Soc., 39, 142. 9.: IC; 11, 217, 1974. 1962. 14) YOSHIDA, M., M. TADA, H. BANSHO, M..MATSUSIII - 41) GRAY, G. M.: Biochem. J., 77, 82, 1960. • MA, K. KOBA, M. ItNo and I. UMEDA: Japan.Poul- 42) DODGE, J. T. and G. B. Pinnies: J. Lipid Res., try Sci., 12, 83, 1975. 8, 667, 1967. 15) YOSHIDA, M. and T. HORIUCHI: Ibid., 12, 96, 43) KUSKE, T. T. and A. ROSENBERG: Ibid., 12, 173, 1975. 1971. 16) FUJIW.ARA, W., T. HORIUCHI, T. TANIGUCHI, I. INO 44) Cotes, E. and J. L. Foo-re: Mid., 11, 433, 1970. GE, S. SAKURAI, M. TOKUOKA, K. YAMANAKA and 45) CHERAYIL, G. D.: Ibid., 9, 207, 1968. H. KGRAHARA: ibid.. 12, 127, 1975. 46) SYENNERHOLNI, L. and S. STALLuettG-STENHAGEN: 17) H.ANSEN, R. P., P.11. SHORLAND, and N. J. COOKE: Ibid., 9, 215, 1968. Nature, 174, 39, 1954. 47) SIDDIQUI, B. and R. H. McCune: Ibid., 9, 366, 18) WEITKAMP, A. W., A. M. SNIILJANIC and S. ROTH - 1968. MAN: J. Am. Chem. Soc., 69, 1936, 1947. 48) MARTINELLI, M., E. TuRcile-rTo, A. M. SEC'S!: 19) HANS':.N, R. P., F. B. SHORLAND and N. J. Coot:e: Boll. soc. ital. biol. sper. 36, 1700, 1960; Chem. Bioehem. J., 53, 374, 1933. Abst., 55, 23748 g, 1961. 20) ii • III • TifFiori'i:::f2.71`,■%i:iit.';': 49) MAtnseot, G., F. CORSINI, G. PAOLI:CC!, G. P. SAL- 1, 78, 1960. VIOLI, Jr. and B. BABINI: Ibid., 38, 726, 1962: 21) HANSI N. R. P., P. B. StfoRLANu and N. J. CooKe: Chem. Ahst., 58, 4381 a, 1963. Bioehem. J., 53, 516, 1951. 50) BLOMSTRAND, R. and S. RADNER: Kg. Fysiograf. 22 ) StiotttAND, F. Nature, 174, 603, 195-1. Sallskap. Lund. Forh., 32. 27, 1962; Chem.. 23i /fuses:, R. P., F. B. SHORLAND and N. J. CooKe: Abst., 59, 31.14 f, 1963. Biochent. J., 58, 513, 1931. 51) BLONISTRANU, R. and K. A. LARSS.ON: Ibid., 32, 21) Culs)1,): M. M. J. and C.Y. Ilupi:Iss: Can. J.Chem., . 77, 1962; Chem. Abst. 59, 2017 f, 1963.
..1• z •e, . ,f ; "e ■■ .'• I. • •..• T.". .; f • I`, . • . •
.r — 2 9-
166 12 >4.: 4 -v; (1975)
52) BADDINGS, H. T. Neth. Milk Dairy J., 16, 217,' Wes, R. and J. KORELESKI: Br. J. Nutr., 31, 143, 1962; Chem. Abst., 58, 8287 e, 1963. 1967. 53) SVENNERHOLM, L.: J. Lipid Res., 9, 570, 1968. 76) BARNESS, L. A.: Science., 140, 76, 1963. 54) HANSEN;R. P., F. B. SHORI.lND and N. J. COOKE: 77) BARNESS, L.A., H. Moss'« and P. GviiRgt: J, Biochem. J., 57, 297, 1954. Biol. Chem., 221, 93, 1956. 55) LYNEN, F.: Methods in Enzymology, Vol. 5, 443, 78) KISHIMOTO, Y., M. W1LLiAms, H. W. MOSER and 1962. K. BIEMANN: J. Lipid Res., 14, 69, 1973. 56) KATZ, J. and J. KORNBLATT: J. Biol. Chem.,237, 79) e 111,5 93 • fee,".:4 le: • .11.11111: 9. • 101. 2466, 1962. 9, 17, 1972. 57) FARVARGER, P. and J. GERLACH: Bull. SOC. Chim. 80) .1,119 MI, 11, 223, 1974. Biol.,"62, 327, 1960; Chem. Abst., 54, 25146f, 81) CANussEt.t., R. G. and S. A. HASHIM: Am. J. Phy- 1960. siol., 217, 1614, 1969. 58) 11AsoRo, E. J. and E. PORTER: J. Lipid Res., 2, 82) HASHIM, S. A., K. KNELL, P. MAo and T. B. VAN • 177, 1961. ITALLIE: Nature, 207, 527, 1965. 59) FELLER, D. D. and E. FEIST: J. Biol. Chem., 228, 83) PLAYOUST, M. R. and K.J. ISSELBACHER: J. Clin. 275, 1957. Invest., 43, 878, 1964; Chem. Abst., 61, 2271 a,
60) jANIES, A. T., G. PETER and M. LAURYSSENS: Boi- 1964. ' chem. J., 64, 726, 1956. 84) LINERES, F. and S.A. HASHINI: Fed. Proc., 26, 61) GRIGOR, M. R., G. G. DUNCKLRY and H. D. PURVE 471, 1967. S: Biochim. BiOphyS. Acta, 281, 389, 1970. 85) KutscitNER, S. and R. HARRIS: J. Nutr., 73, 397, 62) GRICOR, M. R., G. G. DUNCKLEY and H. D. PGR- 1961. o VES: Ibid., 218, 400, 1970. 86) ZURIER, R. B., R. G. CANIPBELL, S. A. HASHINI and 63) MEAD, J. F. and G. M. LEvis: J. Biol. Chem., T. B. VAN ITALLIE: Am. J. Physiol., 212, 291, 238. 1634, 1963. 1967. 64) KISHIMOTO, Y. and N.S. RADIN: J. Lipid Res., 87) OSTWALD, R., R. OKEY, A. SHANNON and J. Tixoco: IL 4, 437, 1963. J. Nutt., 76, 341, 1962. 4: 65) Ktsfumoro, Y. and N. S. RADIN: Ibid., 5, 94, . 88) CANIPBELL, R.G. and S.A. HASHINI: Proc. Soc. ■ • 1964. Exptl. Biol. Med., 141, 653, 1972. 66) STUMPF, P. K. : Nature, 194, 1158, 1962. 89) MYUNG SOOK SHIN: Dissertation Absts. Internat.. 67) HITCHCOCK, G. and .A. 'f. J.ANIES: J. Lipid Res., (B), 30, 4675 B, 1969: Nutr. Abst. & Rev., 41, 5, 593, 1964. 512, 1971. 68) WAKABAYASHI, K. and N. SHINIAZONO: Biochim. 90) 1,1oHsHAuss, H. and R. T. HALMAN: J. Nutr., 91, Biophys. Acta, 70, 132,1963. 528, 1967. 69) KATS, J. and 1. L. CHAIKOFF: J. Am. Chem. Soc. 91) Watts, R. C., J. SPINCER, J.A.F, ROOK and R.G. 77. 2659, 1955. Towsss: Br. J. Nutr., 24, 269, 1970. 70) FLAVIN, M. and S. OcyoA: J. Biol. Chem., 229, 92) BOYER, J. L. and R. Scuctc: Lipids, 4. 615, 965, 1957. 1969. 71) VAN ITALLIE, T. B. and A. K. KHACHADURIAN: 93) YOSHIDA, M., H. IKUNIO and O. SuzuKt:Agr. Biol. Science., 165, 812, 1967. Chem., 35, 1208, 1971. n 72) DRYDEN, L. P. and A. M. HARTMANN: J. Nutr., 94) YOSHIDA, M., H. MORIMOTO and R. ODA: Ibid., 34, 101, 589, 1971. 1301,- 1970. 73) ARNISTRONG, B. K.: Br. J. Nutr., 21, 309, 1967. 95) VISSCFIER, F. E.: J. Biol. Chem., 162, 129, 1946. 74) VENKATARANIAN, S., D. K. BISWAS and B. C. JOHN- 96) SON: J. Nutr., 93, 131, 1967. 97)
1 i
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;
Table 1
Distribution of Straight Chain Odd-Numbered Fatty Acids in the Bodies of Animals
11:0 13:0 15:0 15:1 17:0 17:1 17:2 19:0 19:1 21:0 21:1 23:0 23:1 25:0 25:1 Reference BODY LIPIDS
sheer) *1 1 1.2" 17, 21, 22, musk-ox 23 1.7 0.9 24
cow, kidney area 25 0. 2-- 0. 37- 0. 2 0.2-1. 37 chicken 3.10 1.25 0-1.8 26, 27, 28 cow 0-0. 22 0.13-0.44 t-0.29 26 0. 22- 0.31- horse 0. 15-0.24 0.36 0.42 26 human (elderly fem le) 0.6-0.8 0.2-0.4 O. 3-0.4 0. 6-0. 7 29
butter fat 0.03 0.82 0.45 30, 31, 32, 33 0 MEAT 1
chicken 0-1.1 0.1-0.6 0-19 27, 28, 34
chicken, skin 0-0.1 0.2 0.2 0-1.5 26, 27
O-0.05 0 03-0' 14 35 Dig O. 03 cow 0. 36-2. 01 0. 76-1. 93 0.« 45-1. 17 36, 37, 38 YITK
dte, Holstein 1.2 0.7 39
Jersey 1.7 0.8 39
Ayrshire 0.03 0.06 0.79 0. 07 0.70 0.72 0.27 ('.06 0.04 0.02 0.03 0.03 0.01 40
goat 0.7 2.4 39 • sheep 0.9 2.9 39
horse 0.2 0.5 39
guinea pig 0.7 LO • 39 dog 1.4 2.6 39 human 0.6 1.1 39 Table 1 (cont'd)
PHOSPHOLIPIDS Lecithin, cow, spleen t -_ 1.2 1:4 41 liver 0.2 0.7 41 41 heart - 0.5 1.0 •1.5 - pig, heart - - 0.1 0.4 - - 41 41 sheep, semen 0.3 - 1.9 0.9 ' 16.2 4.3 27 chicken, meat 0.7-0.8 0. 4-0. 5 35 pi -g, meat 0'02- 1.6-2.2 1.0-1.3 0.23-0.35 0. 04 0.2- 0.64- meat 0.16- 36, 37, 38 cow, 0. 69 1.7 1.77 human, red blood cells 0.16 0.44 42 GLYCOLIPIDS 43 rat, spleen 0.9-1.5. 1.2-8.8 1.4-3.1 t-3. 0.' t-5.7 2.6-6.6 1.7-8.7 44 pig, blood t-1.8 t-4.6 t-1.8 -t-1.4 t-1.8 t-1.4 t-5.1 t-3.4 t-1.4 BRAIN human t t-0. 5 t-0. 6 t-0. 8 t-0.3 0.1 t-9.1.-t-1.6 t-8.7. t-16. 7 45, 46 OXYACIDS t-5.1 i i9^ t-8. 5 45, 46, 47 human, brain , t-0.4 t-0.7 t- t-0• 3. 0. 5- t-0.7 2179 44 Pig, blood ¢ t-3.2 t-6.7 ' t-6.6 t-2.0 t-1.2 t-15.0 t-1.6
1) has been isolated and confirmed. 2) % of total fatty acids (including even-numbered fatty acids). 3) trace. 11 13 br-13 15 br-15 17 br-17 Ref. 1.1 11.4 41 Cow, spleens choline plasmalogen -- 0.51 0.6 6.7 23.9 41 kephalin plasmalogen ------2ï-1 2.6 4.4 4.1 41 Cow, heart: choline plasmalogen ------3.4 6.8 1.5 5•9 kephalin plasmalogen ------3.2 3.4 3.9 3.9 41 35.6 1.5 3.9 41 Cow, liver: . choline plasmalogen t2 0.6 0.1 . 4.6 kephalin plasmalogen t -- -- 6.7 29.6 1.9 12.4 41 0.7 0.6 2.6 1.1 41 Pig, heart: choline plasmalogen ------41 kephalin plasmalogen 0.8 -- -- 1.9 1.8 2.8 2.2 Sheep, semen: choline plasmalogen 0.5 -- -- 8.2 12.8 0.7 4.0 41 1) ;o of overall aldehydes, incl.- even-numbered aldehydes. 2) trace
Table 2
Distribution of Straight Chain Odd-Numbered Aldehydes in the Phospholipids of Animals. acetyl Co-A carboxyrase CH -00-,SCo-A HOOC-CH -COrSCo-A 3 2 acetyl Co-A malone Co-A Even-Numbered Fatty Acid CO
_el .- + "C 3 " › "c4 " acetyl Co-A malonyl Co-A CO 2 > ,c6 ., + el C 3 IN ----e4 malonyl Co-A general case: nC0 on nC 2 3 C2n+2 acetyl Co-A malonyl Co-A
Odd-Numbered Fatty Acid nC0 tin 2 nC3 C2n+3 propionyl Co-A malonyl Co-A
Figure 1 - Fatty Acid Biosynthesis e • ■■• ••• • )
Figure 2 - Branched Amino Acid Decomposition Paths
- m4 —NH3 —CO, ale.., CH—CO —SCOA HOOC —CH, —CH., —CO —S —Co—A cir."---cil-ett-coox cFrie' . +HS • C o —A CH,'" 4 v-71-9 n•Co—A 4), .,._-_:;t,Co—A vaiMe isobutyrl Co-A succinyl Co-A.
NH, —NH, _,.. CH, —CO —S —Co—A I —CO, CH, —CH ,--, ,*.)PCo—AaC etyl Co-A C H—CH—COOH C H—CO—S•Co—A +HS • Co—A e-- CH,' m -••• CH, —CH, —CO —S —Co—A ' -iVII-fi>> a—, 1-Miareo —A 7'cr )kCo—A isoleucine 0(-methy1 butyric acid Co-A Propionyl Co-A
. - NH, - —NH, • • CH, CO —S —Co—A • CO. ././ -co,. • •CH,--, Cii_cH, —CH —COOH cire-- cH 7 acetyl Co-A • CH,'". +HS • Co —A CH's"- u 4 id:" CH, —CO—CH, —00011 leucine isovaleryl Co-A acetoacetic acid
Figure 3 - Fatty Acid Oxidation Mechanisms
1) o(-Oxidation (C 1 decomposition)
A oc O * 0 f R-CH -CH COOH 2 2 -v RCH2-CHOH-COOH ---> R-CH2-COOH '.002
In /3-Oxidation
A M. (3 R-CH2 unit 4/ .4CH2 -COOH > R-COOH C 2
III)co-Oxidation
CH3 (CH2 ) nCOOH ---* HOOC(CH2)nCOOH 4à 1: -35-
Figure 4 - Metabolism Path of Propionic Acid
propionyl Co-A carboxyrase CH, CH, CH, CO, HS.zr Co — A HC —COOH CH, 7 I CO —SCo —A COOH CO—SCo—A a :zit. Co —A methyl malonyl Co-A -70 ue>13. vitamin B12 propionic acid propionyl Co-A coon1
TCA Cycle ) CH, ■ CH, CO —SCo —A