JPH03280855A - Gamma-linolenic acid-containing composition - Google Patents
Gamma-linolenic acid-containing compositionInfo
- Publication number
- JPH03280855A JPH03280855A JP2078981A JP7898190A JPH03280855A JP H03280855 A JPH03280855 A JP H03280855A JP 2078981 A JP2078981 A JP 2078981A JP 7898190 A JP7898190 A JP 7898190A JP H03280855 A JPH03280855 A JP H03280855A
- Authority
- JP
- Japan
- Prior art keywords
- group
- linolenic acid
- formula
- composition
- gamma
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 20
- VZCCETWTMQHEPK-QNEBEIHSSA-N gamma-linolenic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/CCCCC(O)=O VZCCETWTMQHEPK-QNEBEIHSSA-N 0.000 title claims abstract description 9
- VZCCETWTMQHEPK-UHFFFAOYSA-N gamma-Linolensaeure Natural products CCCCCC=CCC=CCC=CCCCCC(O)=O VZCCETWTMQHEPK-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 235000020664 gamma-linolenic acid Nutrition 0.000 title claims abstract description 8
- 229960002733 gamolenic acid Drugs 0.000 title claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 239000000126 substance Substances 0.000 claims abstract description 8
- PEYUIKBAABKQKQ-AFHBHXEDSA-N (+)-sesamin Chemical compound C1=C2OCOC2=CC([C@H]2OC[C@H]3[C@@H]2CO[C@@H]3C2=CC=C3OCOC3=C2)=C1 PEYUIKBAABKQKQ-AFHBHXEDSA-N 0.000 claims abstract description 7
- PEYUIKBAABKQKQ-UHFFFAOYSA-N epiasarinin Natural products C1=C2OCOC2=CC(C2OCC3C2COC3C2=CC=C3OCOC3=C2)=C1 PEYUIKBAABKQKQ-UHFFFAOYSA-N 0.000 claims abstract description 7
- 235000013402 health food Nutrition 0.000 claims abstract description 6
- VRMHCMWQHAXTOR-CMOCDZPBSA-N sesamin Natural products C1=C2OCOC2=CC([C@@H]2OC[C@@]3(C)[C@H](C=4C=C5OCOC5=CC=4)OC[C@]32C)=C1 VRMHCMWQHAXTOR-CMOCDZPBSA-N 0.000 claims abstract description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000005429 oxyalkyl group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- VFLDPWHFBUODDF-FCXRPNKRSA-N curcumin Chemical compound C1=C(O)C(OC)=CC(\C=C\C(=O)CC(=O)\C=C\C=2C=C(OC)C(O)=CC=2)=C1 VFLDPWHFBUODDF-FCXRPNKRSA-N 0.000 abstract description 14
- 239000004148 curcumin Substances 0.000 abstract description 7
- 235000012754 curcumin Nutrition 0.000 abstract description 7
- 229940109262 curcumin Drugs 0.000 abstract description 7
- VFLDPWHFBUODDF-UHFFFAOYSA-N diferuloylmethane Natural products C1=C(O)C(OC)=CC(C=CC(=O)CC(=O)C=CC=2C=C(OC)C(O)=CC=2)=C1 VFLDPWHFBUODDF-UHFFFAOYSA-N 0.000 abstract description 7
- 239000008159 sesame oil Substances 0.000 abstract description 6
- 235000011803 sesame oil Nutrition 0.000 abstract description 6
- 150000001875 compounds Chemical class 0.000 abstract description 5
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 1
- 125000005055 alkyl alkoxy group Chemical group 0.000 abstract 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 abstract 1
- 229960004488 linolenic acid Drugs 0.000 description 17
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 10
- 235000012000 cholesterol Nutrition 0.000 description 5
- 235000013305 food Nutrition 0.000 description 5
- 239000000284 extract Substances 0.000 description 4
- 244000163122 Curcuma domestica Species 0.000 description 3
- 235000003392 Curcuma domestica Nutrition 0.000 description 3
- 102000002322 Egg Proteins Human genes 0.000 description 3
- 108010000912 Egg Proteins Proteins 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 241000207961 Sesamum Species 0.000 description 3
- 235000003434 Sesamum indicum Nutrition 0.000 description 3
- 235000003373 curcuma longa Nutrition 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 235000013345 egg yolk Nutrition 0.000 description 3
- 210000002969 egg yolk Anatomy 0.000 description 3
- 244000144972 livestock Species 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 235000013976 turmeric Nutrition 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000271566 Aves Species 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 241000287828 Gallus gallus Species 0.000 description 2
- 108010068370 Glutens Proteins 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 2
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 235000013601 eggs Nutrition 0.000 description 2
- -1 etc. Chemical group 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 2
- 235000021312 gluten Nutrition 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 2
- 235000013372 meat Nutrition 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 235000013336 milk Nutrition 0.000 description 2
- 239000008267 milk Substances 0.000 description 2
- 210000004080 milk Anatomy 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 244000144977 poultry Species 0.000 description 2
- 235000013594 poultry meat Nutrition 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- BVCOHOSEBKQIQD-UHFFFAOYSA-N 2-tert-butyl-6-methoxyphenol Chemical compound COC1=CC=CC(C(C)(C)C)=C1O BVCOHOSEBKQIQD-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 description 1
- 241000235555 Cunninghamella Species 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- 239000005770 Eugenol Substances 0.000 description 1
- 235000019733 Fish meal Nutrition 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 235000019735 Meat-and-bone meal Nutrition 0.000 description 1
- 241000235575 Mortierella Species 0.000 description 1
- 241000235395 Mucor Species 0.000 description 1
- 241000219925 Oenothera Species 0.000 description 1
- 235000004496 Oenothera biennis Nutrition 0.000 description 1
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 description 1
- 235000019779 Rapeseed Meal Nutrition 0.000 description 1
- 235000019764 Soybean Meal Nutrition 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- XDCSXSSWDRGJOX-UHFFFAOYSA-N anisole;1,2-dimethoxybenzene Chemical compound COC1=CC=CC=C1.COC1=CC=CC=C1OC XDCSXSSWDRGJOX-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 208000011775 arteriosclerosis disease Diseases 0.000 description 1
- 235000014590 basal diet Nutrition 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 235000013330 chicken meat Nutrition 0.000 description 1
- 208000019425 cirrhosis of liver Diseases 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 201000006549 dyspepsia Diseases 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 229960002217 eugenol Drugs 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000004467 fishmeal Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 210000003127 knee Anatomy 0.000 description 1
- 229930013686 lignan Natural products 0.000 description 1
- 150000005692 lignans Chemical class 0.000 description 1
- 235000009408 lignans Nutrition 0.000 description 1
- 230000037356 lipid metabolism Effects 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 239000000401 methanolic extract Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000004456 rapeseed meal Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000004455 soybean meal Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 235000021195 test diet Nutrition 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Fodder In General (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Seeds, Soups, And Other Foods (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明はＴ−リノレン酸含有組成物に関し、詳しくはＴ
−リノレン酸またはその誘導体を安定した状態で含有せ
しめた健康食品用、飼料用などとして有用な組成物に関
する。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a composition containing T-linolenic acid.
- It relates to a composition useful as a health food, a feed, etc., containing linolenic acid or a derivative thereof in a stable state.
〔従来の技術１発明が解決しようとする課題〕Ｔ−リノ
レン酸は脂質代謝異常が原因となって起こる動脈硬化症
、肝硬変等の成人病の予防に有効であることが知られて
いる。そのため、γ−リノレン酸を食品に配合するため
の工夫がなされており、例えば飼料中にＴ−リノレン酸
を配合して鶏等の家禽類、牛等の家畜類に与え、Ｔ−リ
ノレン酸を含む卵、肉、牛乳などを得ようとする試みが
なされている（特開昭６１−２１６６５８号公報、同６
３−９８３５５号公報等）。[Prior Art 1] Problems to be Solved by the Invention T-linolenic acid is known to be effective in preventing adult diseases such as arteriosclerosis and liver cirrhosis caused by abnormal lipid metabolism. Therefore, efforts have been made to incorporate γ-linolenic acid into foods. For example, T-linolenic acid is added to feed and given to poultry such as chickens and livestock such as cows, and T-linolenic acid is added to food. Attempts have been made to obtain eggs, meat, milk, etc. containing the
3-98355, etc.).
一般に、産卯鶏が摂取した脂肪酸は卵黄に移行して卵黄
の脂質成分として蓄積されることが知られている。Generally, it is known that fatty acids ingested by laying hens are transferred to the egg yolk and accumulated as a lipid component of the egg yolk.
しかしながら、Ｔ−リノレン酸の場合、卵黄への移行、
蓄積は非常に少ないことが判明した。However, in the case of T-linolenic acid, the transfer to egg yolk,
The accumulation was found to be very low.
そこで、本発明者はヒトや動物の体内においてＴ−リノ
レン酸が蓄積される方法を確立すべく、鋭意研究を重ね
た結果、特定の物質をＴ−リノレン酸と共に配合した組
成物を開発することに成功し、本発明に到達した。Therefore, as a result of intensive research to establish a method for accumulating T-linolenic acid in the bodies of humans and animals, the present inventor has developed a composition containing a specific substance together with T-linolenic acid. We succeeded in this and arrived at the present invention.
本発明は（ａ） ｒ−リノレン酸またはその誘導体およ
び（ロ）一般式
（式中、Ｒ１は低級アルキル基を示し、Ｒ２は水１基、
アルキル基、アルコキシ基、アルケニル基。The present invention provides (a) r-linolenic acid or its derivative and (b) general formula (wherein R1 represents a lower alkyl group, R2 represents one water group,
Alkyl group, alkoxy group, alkenyl group.
またはオキシアルキル基を示す、Ｒ２が複数である場合
には、複数のＲ２は同一であっても異なっていてもよい
。ｎは０〜５の整数を示す、）で表される化合物、セサ
ミンおよび
一般式
（式中、Ｒ３は低級アルキル基を示し、Ｒ４は水酸基、
アルキル基、アルコキシ基、アルケニル基。Alternatively, when there is a plurality of R2's representing an oxyalkyl group, the plurality of R2's may be the same or different. n represents an integer of 0 to 5), sesamin and the compound represented by the general formula (wherein, R3 represents a lower alkyl group, R4 represents a hydroxyl group,
Alkyl group, alkoxy group, alkenyl group.
オキシアルキル基を示す。Ｒ′が複数である場合には、
複数のＲ４は同一であっても異なっていてもよい。ｎは
Ｏ〜５の整数を示す。）で表されるクルクミンまたはそ
の誘導体の中から選ばれた少なくとも１種の物質を含有
する組成物を提供するものである。Indicates an oxyalkyl group. If R′ is plural,
A plurality of R4s may be the same or different. n represents an integer of 0 to 5. ) A composition containing at least one substance selected from curcumin or its derivatives is provided.
γ−リノレン酸の供給源としてはマツヨイグサ属の植物
の種子等のほかモルティエレラ（Ｍｏｒｔｉｅｒｅｌ
Ｉａ）属、ムコール（Ｍｕｃｏｒ）属、カニンガメラ（
Ｃｕｎｎｉｎｇｈａｍｅｌｌａ）属等に属する糸状菌な
どがある（特開昭６１−２４４２１６号公報等）。Sources of γ-linolenic acid include seeds of plants of the evening primrose genus, as well as Mortierella
Ia), genus Mucor, genus Cunningamela (
There are filamentous fungi belonging to the genus Cunninghamella (Japanese Unexamined Patent Publication No. 61-244216, etc.).
また、本発明においてγ−リノレン酸の誘導体としては
、各種アルコールエステル、アミド、チオエステル、塩
、ハロゲン化物等の生体に適合性のあるものであれば任
意に用いることができる。Further, in the present invention, any derivative of γ-linolenic acid can be used as long as it is compatible with living organisms, such as various alcohol esters, amides, thioesters, salts, halides, and the like.
前記３種の物質はＴ−リノレン酸を蓄積させる作用を有
しており、これらは単独で、あるいは組み合わせて使用
する。ここで、前記一般式（１）で表される化合物にお
いてＲ１はメチル基、エチル基、プロピル基等の炭素数
１〜６の低級アルキル基を示し、Ｒ２は水酸基、アルキ
ル基、アルコキシ基、アルケニル基、オキシアルキル基
を示す。The three substances mentioned above have the effect of accumulating T-linolenic acid, and are used alone or in combination. Here, in the compound represented by the general formula (1), R1 represents a lower alkyl group having 1 to 6 carbon atoms such as a methyl group, ethyl group, or propyl group, and R2 represents a hydroxyl group, an alkyl group, an alkoxy group, or an alkenyl group. group, oxyalkyl group.
アルキル基としてはメチル基、エチル基、プロピル基、
ブチル基、ヘプチル基、オクチル基、ノニル基（直鎖状
または枝状のいずれでもよい）などを、アルコキシ基と
してはメトキシ基、エトキシ基などを、アルケニル基と
してはアリル基、３ブテニル基などを、オキシアルキル
基としてはオキシメチル基、２−オキシエチル基、３−
オキシプロピル基、４−オキシブチル基などを挙げるこ
とができる。また、Ｒ２が１分子内に複数ある場合、複
数のＲ２は同一であっても異なっていてもよい。ｎはＯ
〜５の整数を示す。上記一般式（１）で表される化合物
の具体例としてはアニソールジメトキシベンゼン、ジェ
トキシベンゼン、 ｔｅｒｔ−ブチルヒドロキシアニソ
ール（ＢＨＡ）、オイゲノール等が挙げられる。これら
は油脂などの抗酸化剤や香料として工業的に多く生産さ
れているものが多いため、容易に入手することができる
。Alkyl groups include methyl group, ethyl group, propyl group,
Butyl groups, heptyl groups, octyl groups, nonyl groups (which may be linear or branched), etc., alkoxy groups include methoxy groups, ethoxy groups, etc., alkenyl groups include allyl groups, 3-butenyl groups, etc. , oxyalkyl groups include oxymethyl group, 2-oxyethyl group, 3-
Examples include oxypropyl group and 4-oxybutyl group. Furthermore, when there are multiple R2's in one molecule, the multiple R2's may be the same or different. n is O
Indicates an integer between ~5. Specific examples of the compound represented by the above general formula (1) include anisole dimethoxybenzene, jetoxybenzene, tert-butylhydroxyanisole (BHA), and eugenol. Many of these are industrially produced as antioxidants for oils and fats, and as fragrances, so they are easily available.
また、セサミン（光学異性体のエピ−セサミンも含む）
はゴマ油等に含まれるリグナンの１種である０本発明に
おいてはセサミンとしてゴマ油そのものを用いることも
できる６ゴマ油とはゴマの種子から得られる油を指し、
食用、薬用を問わず用いることができ、特に圧搾抽出し
たものが好ましい。さらに、ゴマや擦りゴマなどからジ
クロロメタン−メタノールなどで抽出した抽出物、圧搾
抽出したものを水蒸気蒸留して得られる抽出物、ゴマ油
中のトリグリセライドをシリカゲルカラムクロマトによ
り除いたもの等も使用することができる。また、ゴマ油
の熱メタノール抽出物等も用いることができる。クルク
ミンはウコンおよび他の開成数種の根茎に含まれている
。本発明に使用する場合、ウコンそのものを使用したり
、ウコンからアセトンなどの溶剤により抽出して得られ
た抽出物、さらには純品等を用いることもできる。Sesamin (including the optical isomer epi-sesamin)
is a type of lignan contained in sesame oil etc. In the present invention, sesame oil itself can be used as sesamin.6 Sesame oil refers to oil obtained from sesame seeds.
It can be used for both edible and medicinal purposes, and compressed extraction is particularly preferred. Furthermore, extracts extracted from sesame seeds or crushed sesame seeds with dichloromethane-methanol, etc., extracts obtained by steam distillation of pressed extracts, and sesame oil with triglycerides removed by silica gel column chromatography can also be used. can. Additionally, a hot methanol extract of sesame oil can also be used. Curcumin is found in the rhizomes of turmeric and several other plant species. When used in the present invention, turmeric itself, an extract obtained by extracting turmeric with a solvent such as acetone, or even a pure product can also be used.
次に、本発明の組成物を動物用飼料として用いる場合、
通常の飼料成分に対して（ａ）成分のｒ −’Ｊルン酸
を１／１０００００〜１／１０、好ましくは１／１００
００〜３／１００１．（ｂ）成分である前記物質を１／
１０００００〜１／１０、好ましくは１／１００００〜
３／１００の割合（重量比）で配合する。（ａ）成分よ
び（ｂ）成分の配合量が下限未満であると、Ｔ−リノレ
ン酸が蓄積し難い上にコレステロールが低下しない、一
方、上限を超えて添加すると、家禽、家畜等による消化
吸収率が低下し、かつ消化不良を起こし、軟便を排泄す
る。Next, when using the composition of the present invention as animal feed,
Component (a) r-'J phosphoric acid is 1/100,000 to 1/10, preferably 1/100 of normal feed ingredients.
00-3/1001. (b) 1/
100,000 to 1/10, preferably 1/10,000 to
Blend at a ratio (weight ratio) of 3/100. If the amount of component (a) and component (b) is below the lower limit, T-linolenic acid will not accumulate easily and cholesterol will not decrease. rate decreases, and causes indigestion and excretion of loose stools.
また、本発明の組成物を健康食品として用いる場合、常
用の成分に対して（ａ）成分のＴ−リノレン酸を１／１
０００００〜９９／１００、好ましくは１／１００〜４
／１０、（ｂ）成分である前記物質を１／１０００００
００００〜９９／１００、好ましくはＩ／１０００００
０〜２／１０の割合（重量比）で配合する。（ａ）成分
よび（ｂ）成分の配合量が下限未満であると、十分なコ
レステロール低下が起こらない。In addition, when using the composition of the present invention as a health food, the amount of T-linolenic acid (component (a)) should be 1/1 of the commonly used ingredients.
00000-99/100, preferably 1/100-4
/10, the substance as component (b) is 1/100000
0000-99/100, preferably I/100000
Blend at a ratio (weight ratio) of 0 to 2/10. If the amounts of component (a) and component (b) are below the lower limit, sufficient cholesterol reduction will not occur.
次に、本発明を実施例により詳しく説明する。 Next, the present invention will be explained in detail with reference to examples.
実施例１ 下記の処方により試験用飼料を調製した。Example 1 Test feed was prepared according to the following formulation.
／
飼 料
３
とうもろこし・マイＵ
７０ ７０ ７０大豆粕、なたね
粕 １２ １０．５ １０．５炭酸カル
シウム、リン酸カルシウム １．５
１．５ １．５グルテンミール
３ ３
３脱脂ヌカ、グルテンフィーＦ ４
４ ４魚粉、肉骨粉
６ ６ ６動物性油脂 １．５
３ １．５食塩、 アミノ酸、 ビタミン、ミネラ
ル ０．５ ０．５ ０．５クルク
ミン １．５ １．５Ｔ−リ
ノレン酸 １５ − １．５ブロイラー
用鶏（アーバンエーカ一種）１２羽を１区とする試験区
に飼養期間５６日を３分し、日令４〜２０日の間は上記
試験用飼料からクルクミンとγ−リノレン酸を除いた基
礎飼料を与え、日令２１〜４８日の間は上記試験用飼料
１〜３のいずれかを与え、その後５６日令までは前記基
礎飼料を与えた。この飼養試験を３反復（雄３６羽。/ Feed 3 Corn/My U
70 70 70 Soybean meal, rapeseed meal 12 10.5 10.5 Calcium carbonate, calcium phosphate 1.5
1.5 1.5 gluten meal
3 3
3 Skimmed bran, gluten fee F 4
4 4 Fish meal, meat and bone meal
6 6 6 Animal fats and oils 1.5
3 1.5 Salt, Amino Acids, Vitamins, Minerals 0.5 0.5 0.5 Curcumin 1.5 1.5 T-Linolenic Acid 15 - 1.5 12 broiler chickens (Urban Acre type) are set as one district. The feeding period of 56 days was divided into 3 parts in the test plots, and between days 4 and 20, the above test diet was given the basal diet excluding curcumin and γ-linolenic acid, and between days 21 and 48, the above diet was given. One of the test feeds 1 to 3 was given, and then the basic feed was given until 56 days of age. This feeding test was repeated three times (36 male birds).
＃Ｒ３６羽）行った。飼養期間終了後（５６日令時）に
層殺し、内申のＴ−リノレン酸含有量およびコレステロ
ール含有量を測定し、平均値を採った。#R36 birds) went. At the end of the feeding period (at the age of 56 days), the rats were sacrificed, and the T-linolenic acid content and cholesterol content of the rats were measured, and the average values were taken.
なお、コレステロールの定量は、国立栄養研究所、農畜
産食品中のコレステロール定量法に関する研究、食品中
の特殊成分分析方法の確立に関する総合研究報告書、第
３４３〜３６７頁、１９７９年の記載にしたがって行っ
た。結果を下表に示す。Cholesterol was quantified according to the National Institute of Nutrition, Research on Cholesterol Determination Methods in Agricultural and Livestock Foods, Comprehensive Research Report on Establishment of Methods for Analyzing Special Components in Foods, pp. 343-367, 1979. went. The results are shown in the table below.
０．０５
０．０４
０．０１＞
０．０１＞
０．２５
０．１
０．１
０．０１＞
０．０１＞
１．１
各区 ｎ・３６．平均値
】ニーー又−−−表
１ ♀ ６２ １
２０♂ ５８ １０５２
♀ ６５ １１
７♂ ６０ １０４３
♀ ３０ ７５２
４ ６８
各区 ｎ・３６．平均値
表から明らかなように、Ｔ−リノレン酸とクルクミンを
組み合わせて配合した試験用飼料３を与えた試験区は他
の試験区に比して内申のＴ−リノレン酸含有量が著量で
あり、一方コレスチロール含有量は他の試験区よりも著
しく減少している。0.05 0.04 0.01>0.01> 0.25 0.1 0.1 0.01>0.01> 1.1 Each ward n・36. Average value] Knee Mata---Table 1 ♀ 62 1
20♂ 58 1052
♀ 65 11
7♂ 60 1043
♀ 30 752
4 68 Each ward n・36. As is clear from the average value table, the test plots fed Test Feed 3 containing a combination of T-linolenic acid and curcumin had a significantly higher internal T-linolenic acid content than the other test plots. On the other hand, the cholestylol content was significantly lower than in the other test groups.
本発明の組成物を飼料として家禽類や家畜類に与えた場
合、摂取されたγ−リノレン酸の体内における代謝が有
効に阻害されるため、卵、乳、肉等に移行、蓄積してＴ
−リノレン酸含有量の高い食品素材が得られる。同様に
、本発明の組成物を健康食品あるいは医薬品としてヒト
が摂取した場合も、生体内で消失することなく、しかも
コレステロール低減効果も優れているので、脂質代謝異
常が原因とされる種々の成人病の予防に役立つことが期
待される。When the composition of the present invention is given to poultry or livestock as feed, the ingested γ-linolenic acid is effectively inhibited from being metabolized in the body, so it is transferred and accumulated in eggs, milk, meat, etc.
- Food materials with high linolenic acid content can be obtained. Similarly, when the composition of the present invention is ingested by humans as a health food or medicine, it does not disappear in the body and has an excellent cholesterol-lowering effect. It is expected that it will be useful in preventing diseases.
Claims (3)
ｂ）一般式 ▲数式、化学式、表等があります▼（ I ） （式中、Ｒ＾１は低級アルキル基を示し、Ｒ＾２は水酸
基、アルキル基、アルコキシ基、アルケニル基、または
オキシアルキル基を示す。Ｒ＾２が複数である場合には
、複数のＲ＾２は同一であっても異なっていてもよい。 ｎは０〜５の整数を示す。）で表される化合物、セサミ
ンおよび 一般式 ▲数式、化学式、表等があります▼（II） （式中、Ｒ＾３は低級アルキル基を示し、Ｒ＾４は水酸
基、アルキル基、アルコキシ基、アルケニル基、オキシ
アルキル基を示す。Ｒ＾４が複数である場合には、複数
のＲ＾４は同一であっても異なっていてもよい。ｎは０
〜５の整数を示す。）で表されるグルクミンまたはその
誘導体の中から選ばれた少なくとも１種の物質を含有す
る組成物。(1) (a) γ-linolenic acid or its derivative and (
b) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (I) (In the formula, R^1 represents a lower alkyl group, and R^2 represents a hydroxyl group, an alkyl group, an alkoxy group, an alkenyl group, or an oxyalkyl group. When there is a plurality of R^2, the plurality of R^2 may be the same or different. n represents an integer of 0 to 5.), sesamin and General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (II) (In the formula, R^3 represents a lower alkyl group, and R^4 represents a hydroxyl group, an alkyl group, an alkoxy group, an alkenyl group, or an oxyalkyl group. When there is a plurality of R^4s, the plurality of R^4s may be the same or different.n is 0
Indicates an integer between ~5. ) A composition containing at least one substance selected from glucmin or its derivatives.
組成物。(2) The composition according to claim 1, which is a composition for health food.
物。(3) The composition according to claim 1, wherein the composition is a feed composition.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2078981A JPH03280855A (en) | 1990-03-29 | 1990-03-29 | Gamma-linolenic acid-containing composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2078981A JPH03280855A (en) | 1990-03-29 | 1990-03-29 | Gamma-linolenic acid-containing composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH03280855A true JPH03280855A (en) | 1991-12-11 |
Family
ID=13677071
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2078981A Pending JPH03280855A (en) | 1990-03-29 | 1990-03-29 | Gamma-linolenic acid-containing composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH03280855A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997001968A1 (en) * | 1995-07-04 | 1997-01-23 | Suntory Limited | FOOD COMPOSITION CONTAINING BALANCING AGENT FOR φ-6 AND φ-3 UNSATURATED FATTY ACIDS |
| US7989007B2 (en) | 2007-07-03 | 2011-08-02 | Vincent James Enterprises, Llc | Weight loss composition |
-
1990
- 1990-03-29 JP JP2078981A patent/JPH03280855A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997001968A1 (en) * | 1995-07-04 | 1997-01-23 | Suntory Limited | FOOD COMPOSITION CONTAINING BALANCING AGENT FOR φ-6 AND φ-3 UNSATURATED FATTY ACIDS |
| US5948451A (en) * | 1995-07-04 | 1999-09-07 | Suntory Limited | Method of modifying the balance of omega unsaturated fatty acids using a dioxabicyclo octane derivative |
| US6159507A (en) * | 1995-07-04 | 2000-12-12 | Suntory Limited | Food composition containing an omega-6/omega-3 unsaturated fatty acid balance modifier |
| US7989007B2 (en) | 2007-07-03 | 2011-08-02 | Vincent James Enterprises, Llc | Weight loss composition |
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