Triglyceride and composition comprising the same

Details Triglyceride and composition comprising the same Triglyceride and composition comprising the same

1999-06-18

2001-06-19

Carr, Deborah D. (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Fatty compounds having an acid moiety which contains the...

C514S547000, C426S601000, C426S648000, C426S807000

Reexamination Certificate

active

06248909

ABSTRACT:

This application claims priority under 35 U.S.C. §§119 and/or 365 to 10-173017 filed in Japan on Jun. 19, 1998 ; the entire content of which is hereby incorporated by reference.
BACKGROUND OF THE INVENTION
1. Field of Invention
The present invention relates to a novel triglyceride and a composition comprising the same, and more particularly, to a triglyceride having a saturated fatty acid having 16 to 18 carbon atoms at the position 2 of the triglyceride, and having a &ohgr;6, &ohgr;9 and/or (3 unsaturated fatty acids at the positions 1 and/or 3.
2. Related Art
The majority of the lipids that so far obtained are neutral fats that comprise a mixture of triglycerides in which various fatty acids are randomly ester-bonded to the positions 1, 2 and 3 of the triglyceride. These lipids were shown to demonstrate different absorption properties and physiological activities according to differences in the bonding positions of the fatty acids. Lipids in which specific fatty acids are bonded to predetermined positions of triglyceride (structured lipids) have recently attracted considerable attention.
For example, Japanese Examined Patent Publication No. 4-12920 discloses a triglyceride having satisfactory digestion and absorption property in which a fatty acid having 8 to 14 carbon atoms is bonded to the position 2 of the triglyceride and fatty acids having 18 or more carbon atoms are bonded to the positions 1 and 3. In addition, since it is known that 2-monoglycerides are of a form that is most easily absorbed by the human body, Japanese Examined Patent Publication No. 5-87497 discloses a triglyceride in which a 0)3 or 0)6 highly unsaturated fatty acid having physiological function is bonded to the position 2, while saturated fatty acids easily hydrolyzable by enzymes of the digestive tract are bonded at the positions 1 and 3. However, there is no disclosure or suggestion of the relationship between the physiological properties and the structure of triglycerides in human breast milk having unsaturated fatty acids.
On the other hand, with respect to the physiological function of fatty acids, attention has focused in recent years on arachidonic acid and docosahexaenoic acid. These fatty acids are contained in human breast milk and have been reported to be useful in infant development (Advances in Polyunsaturated Fatty Acid Research, Elsevier Science Publishers, 1993, pp. 261-264) and to be important in infant growth and brain development (Proc. Natl. Acad. Sci. USA, 90, 1073-1077 (1993), Lancet, 344, 1319-1322 (1994)).
Several official agencies have recommended intake values (premature infants: arachidonic acid: 60 mg/kg, docosahexaenoic acid: 40 mg/kg; normal infants: arachidonic acid: 20 mg/kg, docosahexaenoic acid: 20 mg/kg body weight/day (WHO-FAO (1994)). In several countries in Europe, premature infant formulas have been marketed that contain docosahexaenoic acid and arachidonic acid produced by fermentation blended as triglycerides. However, there have been no considerations given to the bonding positions of arachidonic acid and/or docosahexaenoic acid in the triglycerides added to these formulas.
The triglyceride structure in human breast milk is predicted to be such that there is a high proportion of triglycerides in which palmitic acid (16:0) is bonded to position 2 of the triglyceride, and a high proportion of triglycerides in which highly unsaturated fatty acid or medium chain fatty acid is bonded to positions 1 and 3 (Christie, W. W. (1986): The Positional Distribution of Fatty Acids in Triglycerides, Analysis of Oils and Fats, Hamilton, R. J. and Russell, J. B. eds., pp. 313-339, Elsevier Applied Science, London). However, these are merely suppositions based on the results of analysis of fatty acids in triglycerides, while isolation and structural analysis of triglycerides in human breast milk have not yet been attempted.
In addition, although triglycerides containing arachidonic acid produced by fermentation have been added to formula to allow fatty acid composition to more closely approximate the composition of human breast milk as previously described, since the structure of these triglycerides containing arachidonic acid is such that there is a high proportion of triglycerides in which palmitic acid and other saturated fatty acids are bonded at the positions 1 and 3 while unsaturated fatty acids are bonded at position 2 (J. J. Myher, A. Kuksis, K. Geher, P. W. Park and D. A. Diersen-Schade, Lipids, 31, pp. 207-215 (1996)), it is different from the structure of triglycerides hypothesized in human breast milk.
Thus, there is a strong desire to develop lipids surmised to have the glyceride structure of human breast milk, and more specifically, triglycerides reliably confirmed to have a structure in which saturated fatty acid having 16 to 18 carbon atoms is bonded at the position 2 of the triglyceride, while highly unsaturated fatty acids or medium chain fatty acids are bonded at positions 1 and 3.
SUMMARY OF THE INVENTION
Thus, the object of the present invention is to provide a novel triglyceride having at the position 2 a saturated fatty acid of 16 to 18 carbon atoms, and at the positions 1 and 3 unsaturated fatty acids wherein at least one of these unsaturated fatty acids is a &ohgr;6, &ohgr;9 or &ohgr;3 unsaturated fatty acid; or a novel triglyceride having at position 2 a saturated fatty acid of 16 to 18 carbon atoms, having at one of positions 1 and 3 a saturated fatty acid of 4 to 18 carbon atoms, and having at another position of the positions 1 and 3 a &ohgr;6, &ohgr;9 or &ohgr;3 unsaturated fatty acid; and a composition containing this novel triglyceride.
As a result of earnest research to solve the above-mentioned problems, the inventors of the present invention found that triglyceride estimated to be of target human breast milk type can be manufactured starting from a glyceride clearly determined to have a saturated fatty acid of 16 to 18 carbon atoms at the position 2, allowing lipase that specifically acts on ester bonds at the positions 1 and 3 to act on said glyceride in the presence of &ohgr;6, &ohgr;9 or &ohgr;3 unsaturated fatty acid or ester thereof, resulting in transesterification only at the positions 1 and 3, so as to obtain a triglyceride having at the position 1 and/or 3 &ohgr;6, &ohgr;9 or &ohgr;3 unsaturated fatty acids. Moreover, by comparing the resulting triglyceride with triglyceride obtained from human breast milk, the present inventors also determined for the first time that triglyceride having a saturated fatty acid of 16 to 18 carbon atoms at the position 2 of the triglyceride and highly unsaturated fatty acids at the positions 1 and 3 is in fact present in human breast milk, thereby leading to completion of the present invention.
DETAILED DESCRIPTION
The present invention relates to a novel triglyceride, as well as a food composition, animal feed, therapeutic nutritional product and pharmaceutical composition comprising said triglyceride.
According to the present invention, there is provided a triglyceride represented with the following general formula (I):
wherein R
1
and R
2
are acyl groups of unsaturated fatty acids having 18 to 22 carbon atoms, these acyl groups may be oxidized, and n represents an integer of 14 to 16, and at least one of R
1
or R
2
is a &ohgr;6, &ohgr;9 or &ohgr;3 unsaturated fatty acid; or, a triglyceride represented with the following general formula (II):
wherein, R
3
represents an acyl group of an &ohgr;6, &ohgr;9 or &ohgr;3-unsaturated fatty acid having 18 to 22 carbon atoms, this acyl group may be oxidized, n represents an integer of 14 to 16, and m represents an integer of 2 to 16.
The fatty acid that is present at the positions 1 and/or 3 of the triglyceride of the present invention is &ohgr;3, &ohgr;6 and/or &ohgr;9 unsaturated fatty acid. More specifically, examples of the &ohgr;3 unsaturated fatty acids include:
9,12,15-octadecatrienoic acid (&agr;-linolenic acid) [18:3, &ohgr;3];
6,9,12,15-octadecatetraenoic acid (stearidonic acid) [18:4, &ohgr;3];
11,14,17-eicosatrienoic acid

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