JPH04300826A - Body weight increase inhibitor - Google Patents
Body weight increase inhibitorInfo
- Publication number
- JPH04300826A JPH04300826A JP3064840A JP6484091A JPH04300826A JP H04300826 A JPH04300826 A JP H04300826A JP 3064840 A JP3064840 A JP 3064840A JP 6484091 A JP6484091 A JP 6484091A JP H04300826 A JPH04300826 A JP H04300826A
- Authority
- JP
- Japan
- Prior art keywords
- diglyceride
- fatty acid
- body weight
- lipase
- increase
- 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.)
- Granted
Links
- 239000003112 inhibitor Substances 0.000 title claims abstract description 7
- 230000037396 body weight Effects 0.000 title abstract description 8
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims abstract description 6
- 125000002252 acyl group Chemical group 0.000 claims abstract description 5
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims abstract description 5
- 239000004480 active ingredient Substances 0.000 claims abstract description 4
- 150000004671 saturated fatty acids Chemical class 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract 4
- 230000004584 weight gain Effects 0.000 claims description 10
- 235000019786 weight gain Nutrition 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract description 20
- 108090001060 Lipase Proteins 0.000 abstract description 16
- 239000004367 Lipase Substances 0.000 abstract description 16
- 102000004882 Lipase Human genes 0.000 abstract description 16
- 235000014113 dietary fatty acids Nutrition 0.000 abstract description 16
- 239000000194 fatty acid Substances 0.000 abstract description 16
- 229930195729 fatty acid Natural products 0.000 abstract description 16
- 235000019421 lipase Nutrition 0.000 abstract description 16
- 239000000203 mixture Substances 0.000 abstract description 11
- 150000004665 fatty acids Chemical class 0.000 abstract description 10
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 abstract description 6
- 208000008589 Obesity Diseases 0.000 abstract description 5
- 235000019484 Rapeseed oil Nutrition 0.000 abstract description 5
- 235000020824 obesity Nutrition 0.000 abstract description 5
- 239000003921 oil Substances 0.000 abstract description 4
- 235000019198 oils Nutrition 0.000 abstract description 4
- 238000005809 transesterification reaction Methods 0.000 abstract description 4
- 230000036528 appetite Effects 0.000 abstract description 3
- 235000019789 appetite Nutrition 0.000 abstract description 3
- 150000002632 lipids Chemical class 0.000 abstract description 3
- 239000003814 drug Substances 0.000 abstract description 2
- 150000002148 esters Chemical class 0.000 abstract description 2
- 239000003513 alkali Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003925 fat Substances 0.000 abstract 1
- 230000037406 food intake Effects 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 229940040461 lipase Drugs 0.000 description 12
- 235000011187 glycerol Nutrition 0.000 description 7
- 235000005911 diet Nutrition 0.000 description 6
- -1 fatty acid ester Chemical class 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 230000037213 diet Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000235395 Mucor Species 0.000 description 3
- 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 3
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 229960004488 linolenic acid Drugs 0.000 description 3
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000000199 molecular distillation Methods 0.000 description 3
- 239000007901 soft capsule Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- 241000228212 Aspergillus Species 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 2
- 241000235527 Rhizopus Species 0.000 description 2
- 235000019485 Safflower oil Nutrition 0.000 description 2
- MBMBGCFOFBJSGT-KUBAVDMBSA-N all-cis-docosa-4,7,10,13,16,19-hexaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O MBMBGCFOFBJSGT-KUBAVDMBSA-N 0.000 description 2
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 239000007884 disintegrant Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 230000003834 intracellular effect Effects 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 235000020778 linoleic acid Nutrition 0.000 description 2
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 2
- 239000000944 linseed oil Substances 0.000 description 2
- 235000021388 linseed oil Nutrition 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000003813 safflower oil Substances 0.000 description 2
- 235000005713 safflower oil Nutrition 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 150000003626 triacylglycerols Chemical class 0.000 description 2
- HOBAELRKJCKHQD-UHFFFAOYSA-N (8Z,11Z,14Z)-8,11,14-eicosatrienoic acid Natural products CCCCCC=CCC=CCC=CCCCCCCC(O)=O HOBAELRKJCKHQD-UHFFFAOYSA-N 0.000 description 1
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- 241000228245 Aspergillus niger Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 235000021298 Dihomo-γ-linolenic acid Nutrition 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 108010093096 Immobilized Enzymes Proteins 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 108010048733 Lipozyme Proteins 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 102000019280 Pancreatic lipases Human genes 0.000 description 1
- 108050006759 Pancreatic lipases Proteins 0.000 description 1
- 235000004347 Perilla Nutrition 0.000 description 1
- 244000124853 Perilla frutescens Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 241000303962 Rhizopus delemar Species 0.000 description 1
- 241000235545 Rhizopus niveus Species 0.000 description 1
- 240000005384 Rhizopus oryzae Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 206010049040 Weight fluctuation Diseases 0.000 description 1
- 231100000460 acute oral toxicity Toxicity 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- JAZBEHYOTPTENJ-JLNKQSITSA-N all-cis-5,8,11,14,17-icosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O JAZBEHYOTPTENJ-JLNKQSITSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000000883 anti-obesity agent Substances 0.000 description 1
- 229940125710 antiobesity agent Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000021342 arachidonic acid Nutrition 0.000 description 1
- 229940114079 arachidonic acid Drugs 0.000 description 1
- 208000011775 arteriosclerosis disease Diseases 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 239000011942 biocatalyst Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- HOBAELRKJCKHQD-QNEBEIHSSA-N dihomo-γ-linolenic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(O)=O HOBAELRKJCKHQD-QNEBEIHSSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 235000020669 docosahexaenoic acid Nutrition 0.000 description 1
- 229940090949 docosahexaenoic acid Drugs 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 235000006694 eating habits Nutrition 0.000 description 1
- 235000020673 eicosapentaenoic acid Nutrition 0.000 description 1
- 229960005135 eicosapentaenoic acid Drugs 0.000 description 1
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000004217 heart function Effects 0.000 description 1
- 230000003100 immobilizing effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- FCCDDURTIIUXBY-UHFFFAOYSA-N lipoamide Chemical compound NC(=O)CCCCC1CCSS1 FCCDDURTIIUXBY-UHFFFAOYSA-N 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 235000021180 meal component Nutrition 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 229940116369 pancreatic lipase Drugs 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【０００１】0001
【産業上の利用分野】本発明は体重増加抑制剤に関し、
更に詳細には脂質の過剰摂取による肥満を防止し、体重
の増加を抑制する薬剤に関する。[Industrial Application Field] The present invention relates to a weight gain inhibitor,
More specifically, the present invention relates to a drug that prevents obesity caused by excessive intake of lipids and suppresses weight gain.
【０００２】0002
【従来の技術】近年、食生活の変化に伴ない肥満症が増
加しつつある。肥満症は、心機能の低下、血圧の上昇、
動脈硬化の発生など種々の疾患の危険因子となる。かか
る肥満症の治療の基本は、食餌療法と運動である。しか
し、食餌療法は、カロリー計算が繁雑であり、また管理
の困難さから必ずしも良好な効果を得難い。一方、運動
量の増加は、効果に充分にでないという問題がある。BACKGROUND OF THE INVENTION In recent years, obesity has been increasing due to changes in eating habits. Obesity causes decreased heart function, increased blood pressure,
It is a risk factor for various diseases such as the development of arteriosclerosis. The basics of treatment for obesity are diet and exercise. However, dietary therapy requires complicated calorie counting and is difficult to manage, making it difficult to obtain good effects. On the other hand, there is a problem that increasing the amount of exercise is not sufficiently effective.
【０００３】0003
【発明が解決しようとする課題】従って、食餌量を低下
させることなく体重の増加を抑制できる肥満防止剤の開
発が望まれていた。[Problems to be Solved by the Invention] Therefore, it has been desired to develop an anti-obesity agent that can suppress weight gain without reducing the amount of food consumed.
【０００４】0004
【課題を解決するための手段】そこで、本発明者らは上
記課題を解決すべく種々検討した結果、トリグリセリド
の代わりにジグリセリドを含有する食餌を摂取すれば食
欲を低下させることなく、体重を低下させることができ
ることを見出し、本発明を完成した。[Means for Solving the Problems] Therefore, as a result of various studies to solve the above problems, the present inventors found that if a diet containing diglyceride instead of triglyceride is taken, the body weight can be reduced without reducing appetite. The present invention was completed based on the discovery that this can be done.
【０００５】すなわち、本発明はジグリセリドを有効成
分とする体重増加抑制剤を提供するものである。That is, the present invention provides a weight gain inhibitor containing diglyceride as an active ingredient.
【０００６】本発明の体重増加抑制剤に用いられるジグ
リセリドとしては、例えば次の一般式（１）[0006] As the diglyceride used in the weight gain inhibitor of the present invention, for example, the following general formula (1) is used.
【０００７
】0007
]
【化２】[Case 2]
【０００８】〔式中、Ｒ１ 、Ｒ２ 及びＲ３ のうち
２個は炭素数１２〜２２の飽和脂肪酸又は不飽和脂肪酸
由来のアシル基を示し、残余は水素原子を示す〕
で表わされるジグリセリドから選ばれる１種又は２種以
上が挙げられる。かかる飽和脂肪酸又は不飽和脂肪酸と
しては、ステアリン酸、オレイン酸、リノール酸、リノ
レン酸、ジホモγ−リノレン酸、アラキドン酸、エイコ
サペンタエン酸、ドコサヘキサエン酸等が挙げられる。
より好ましくは、炭素数１６〜２０の不飽和脂肪酸由来
のアシル基を有するジグリセリドである。[In the formula, two of R1, R2 and R3 represent an acyl group derived from a saturated or unsaturated fatty acid having 12 to 22 carbon atoms, and the remainder represents a hydrogen atom.] One or more types may be mentioned. Examples of such saturated or unsaturated fatty acids include stearic acid, oleic acid, linoleic acid, linolenic acid, dihomo-γ-linolenic acid, arachidonic acid, eicosapentaenoic acid, docosahexaenoic acid, and the like. More preferably, it is a diglyceride having an acyl group derived from an unsaturated fatty acid having 16 to 20 carbon atoms.
【０００９】かかるジグリセリドの製造法は、特に制限
されないが、例えば油脂とグリセリンの混合物をアルカ
リ金属及び／又はアルカリ土類金属の水酸化物の存在下
でエステル交換反応させるか、あるいは脂肪酸又は脂肪
酸エステルとグリセリンとの混合物にリパーゼを作用さ
せてエステル化反応を行なうことにより製造される。エ
ステル交換反応の具体例を挙げれば、リノール酸高含有
トリグリセリド １００部とリノレン酸高含有トリグリ
セリド １００部との混合物に精製グリセリン３０〜１
００部（好ましくは約５０部）を配合し、触媒としてＣ
ａ（ＯＨ）２ を ０．２部添加し、窒素気流減圧下で
２３０℃、３０分間攪拌を続けてランダムエステル交
換反応を行う。冷却後脱グリセリンし、薄膜式分子蒸留
にてモノグリセリドを除去する。蒸留残渣物として濃度
８５％のジグリセリドを得る。本製造で用いるリノール
酸高含有トリグリセリドとしてサフラワー油、大豆油、
トウモロコシ油等が挙げられるが、特にサフラワー油が
好ましい。またリノレン酸高含有トリグリセリドとして
アマニ油、シソ油、トウハゼ精油、エノ油等が挙げられ
るが、特にアマニ油が好ましい。The method for producing such diglycerides is not particularly limited, but for example, a mixture of oil and fat and glycerin may be transesterified in the presence of an alkali metal and/or alkaline earth metal hydroxide, or a fatty acid or fatty acid ester may be transesterified. It is produced by applying lipase to a mixture of glycerin and glycerin to perform an esterification reaction. To give a specific example of the transesterification reaction, 30 to 1 part of purified glycerin is added to a mixture of 100 parts of linoleic acid-rich triglyceride and 100 parts of linolenic acid-rich triglyceride.
00 parts (preferably about 50 parts) and C as a catalyst.
0.2 part of a(OH)2 is added, and stirring is continued for 30 minutes at 230° C. under reduced pressure in a nitrogen stream to carry out a random transesterification reaction. After cooling, deglycerol is removed, and monoglycerides are removed by thin film molecular distillation. Diglyceride with a concentration of 85% is obtained as a distillation residue. The linoleic acid-rich triglycerides used in this production include safflower oil, soybean oil,
Examples include corn oil, but safflower oil is particularly preferred. Examples of triglycerides with high linolenic acid content include linseed oil, perilla oil, cane goby essential oil, and eno oil, with linseed oil being particularly preferred.
【００１０】また、リパーゼによるエステル化反応の具
体例を挙げれば、グリセリン１モルに対し脂肪酸又は脂
肪酸エステル １．５モル以上を添加した混合物に、リ
パーゼを脂肪酸又は脂肪酸エステル１ｇに対し ２００
〜１０００ｕｎｉｔｓ 添加し、４０℃で２１時間攪拌
を続けてエステル化反応を行なう。反応終了物よりリパ
ーゼをろ別後、未反応脂肪酸又は脂肪酸エステル及びモ
ノグリセリドを分子蒸留にて除去することにより、ジグ
リセリドを得る。使用する脂肪酸は、目的とするジグリ
セリドに応じて選択すればよい。また、脂肪酸エステル
としては、炭素数１〜３の低級アルコール類とのエステ
ルが好ましい。ここで炭素数１〜３の低級アルコールと
しては、例えばメタノール、エタノール、プロパノール
、イソプロパノールなどが挙げられる。これらの脂肪酸
又は脂肪酸エステルは単独又は２種以上を混合して用い
ることができる。また、リパーゼとしては、固定化又は
菌体内１，３−位選択的リパーゼが挙げられる。固定化
１，３−位選択的リパーゼは１，３−位選択的リパーゼ
を公知の方法で固定化することにより得られる。固定化
のための公知の方法は、例えば「固定化酵素」千畑一郎
編集、講談社刊、９〜８５頁及び「固定化生体触媒」千
畑一郎編、講談社刊、１２〜１０１ 頁に記載されてい
るが、イオン交換樹脂により固定する方法が好ましいも
のとして例示される。固定化に用いられる１，３−位選
択的リパーゼとしては、リゾプス（Ｒｈｉｚｏｐｕｓ）
属、アスペルギルス（Ａｓｐｅｒｇｉｌｌｕｓ）属、ム
コール（Ｍｕｃｏｒ）属等の微生物由来のリパーゼ、膵
臓リパーゼ等がある。例えばリゾプス・デレマー（Ｒｈ
ｉｚｏｐｕｓ ｄｅｌｅｍａｒ）、リゾプス・ジャポニ
カス（Ｒｈｉｚｏｐｕｓ ｊａｐｏｎｉｃｕｓ）、リゾ
プス・ニベウス（Ｒｈｉｚｏｐｕｓ ｎｉｖｅｕｓ）、
アスペルギルス・ニガー（Ａｓｐｅｒｇｉｌｌｕｓ ｎ
ｉｇｅｒ）、ムコール・ジャパニカス（Ｍｕｃｏｒｊａ
ｖａｎｉｃｕｓ）、ムコール・ミーハイ（Ｍｕｃｏｒ
ｍｉｅｈｅｉ）などを起源とするリパーゼを使用するこ
とができる。市販の固定化１，３−位選択的リパーゼと
しては、ノボ・インダストリーＡ．Ｓ．社製の商品名「
Ｌｉｐｏｚｙｍｅ３Ａ」がある。菌体内１，３−位選択
的リパーゼは、微生物菌体に１，３−位選択的リパーゼ
が吸着又は結合したもので、市販品としては、大阪細菌
研究所製の商品名「オリパーゼ」がある。これらのうち
、イオン交換樹脂で固定化したリパーゼを用いるのが特
に好ましい。得られたジグリセリド粗生成物中のジグリ
セリド含量は、蒸留法又はケイ酸カラムクロマトグラフ
法等により増加させることができる。[0010] Also, to give a specific example of the esterification reaction using lipase, in a mixture in which 1.5 moles or more of fatty acid or fatty acid ester is added to 1 mole of glycerin, lipase is added to 1 g of fatty acid or fatty acid ester at 200%
~1000 units were added, and stirring was continued at 40°C for 21 hours to carry out the esterification reaction. After filtering off the lipase from the reaction product, unreacted fatty acids or fatty acid esters and monoglycerides are removed by molecular distillation to obtain diglycerides. The fatty acid to be used may be selected depending on the desired diglyceride. Furthermore, as the fatty acid ester, esters with lower alcohols having 1 to 3 carbon atoms are preferable. Examples of the lower alcohol having 1 to 3 carbon atoms include methanol, ethanol, propanol, and isopropanol. These fatty acids or fatty acid esters can be used alone or in combination of two or more. Furthermore, examples of the lipase include immobilized or intracellular 1,3-position selective lipase. The immobilized 1,3-position selective lipase can be obtained by immobilizing a 1,3-position selective lipase by a known method. Known methods for immobilization are described, for example, in "Immobilized Enzymes" edited by Ichiro Chibata, published by Kodansha, pages 9-85 and "Immobilized Biocatalysts" edited by Ichiro Chibata, published by Kodansha, pages 12-101. However, a method of fixing with an ion exchange resin is exemplified as a preferred method. As the 1,3-position selective lipase used for immobilization, Rhizopus
There are lipases derived from microorganisms such as Aspergillus genus, Aspergillus genus, and Mucor genus, pancreatic lipase, and the like. For example, Rhizopus delemer (Rh
Rhizopus delemar), Rhizopus japonicus, Rhizopus niveus,
Aspergillus niger
iger), Mucorja japanicus (Mucorja
vanicus), Mucor Mihai (Mucor
Lipases originating from A. miehei) can be used. Commercially available immobilized 1,3-position selective lipases include Novo Industries A. S. Company product name “
Lipozyme 3A" is available. Intracellular 1,3-position selective lipase is a 1,3-position selective lipase adsorbed or bound to microbial cells, and a commercially available product is the product name "Olipase" manufactured by Osaka Bacteria Research Institute. . Among these, it is particularly preferable to use lipase immobilized with an ion exchange resin. The diglyceride content in the obtained crude diglyceride product can be increased by a distillation method, a silicic acid column chromatography method, or the like.
【００１１】これらのジグセリドのラットにおける経口
急性毒性は１０ｇ／ｋｇ体重以上であり、安全性の高い
ものである。[0011] The oral acute toxicity of these digcerides in rats is 10 g/kg body weight or more, and they are highly safe.
【００１２】本発明の体重増加抑制剤は、経口、非経口
の何れの方法によっても投与することができ、経口投与
用の剤型としては、例えば錠剤、カプセル剤、散剤、顆
粒剤及びシロップ剤等が挙げられ、非経口投与用の剤型
としては注射剤、経腸用製剤等が挙げられる。これらの
調製には通常の賦形剤、崩壊剤、結合剤、滑沢剤、色素
、希釈剤などが用いられる。The weight gain inhibitor of the present invention can be administered either orally or parenterally, and dosage forms for oral administration include, for example, tablets, capsules, powders, granules, and syrups. Examples of dosage forms for parenteral administration include injections and enteral preparations. Conventional excipients, disintegrants, binders, lubricants, dyes, diluents, etc. are used in their preparation.
【００１３】賦形剤としてはブドウ糖、乳糖などが、崩
壊剤としてはデンプン、アルギン酸ナトリウムなどが、
滑沢剤としてはステアリン酸マグネシウム、硫酸パラフ
ィン、タルクなどが、結合剤としてはジメチルセルロー
ス、ゼラチン、ポリビニルピロリドンなどが用いられる
。投与量は通常成人においてジグリセリドとして１日１
ｇ〜７０ｇであるが、年齢、症状等により増減すること
ができる。なお、好ましい投与形態は通常の食事への添
加であり、食事成分中の脂質の５０重量％以上をジグリ
セリドに置き換えるのが好ましい。Excipients include glucose, lactose, etc.; disintegrants include starch, sodium alginate, etc.
Magnesium stearate, paraffin sulfate, talc, etc. are used as lubricants, and dimethylcellulose, gelatin, polyvinylpyrrolidone, etc. are used as binders. The usual dosage for adults is 1 diglyceride per day.
The amount can be increased or decreased depending on age, symptoms, etc. A preferred form of administration is addition to normal meals, and it is preferred that 50% by weight or more of the lipids in the meal components be replaced with diglycerides.
【００１４】[0014]
【実施例】次に実施例を挙げて本発明を更に説明するが
、本発明はこれに限定されるものではない。EXAMPLES Next, the present invention will be further explained with reference to Examples, but the present invention is not limited thereto.
【００１５】参考例１ ジグリセリドの製造：なたね
油（ヨウ素価 １６８）３７５ｇにグリセリン１２５ｇ
を配合し、全系に対して０．１重量％の水酸化カルシウ
ムを添加して、窒素雰囲気下、 ２３０℃で３０分間攪
拌を続けてランダムエステル交換反応を行なった。冷却
後、反応物を分液ロートに移し分層後、下層を除去した
。更に１０％クエン酸水溶液 ５００ｍｌ加えて攪拌し
、放置分離後、上層部を脱水ろ過し、粗なたね油脂肪酸
組成ジグリセリドを得た。更に粗なたね油脂肪酸組成ジ
グリセリドを １９０℃、０．０１ｍｍＨｇの条件下で
薄膜式分子蒸留器に通して、本発明に適するジグリセリ
ドを含有する反応生成物を１６５ｇ得た。得られた反応
生成物の脂肪酸組成及び含有分子種を表１及び表２にそ
れぞれ示す。なお、これらの表中にはトリグリセリドと
してなたね油についての分析結果も併せて示す。Reference Example 1 Production of diglyceride: 125 g of glycerin in 375 g of rapeseed oil (iodine value 168)
0.1% by weight of calcium hydroxide was added to the total system, and stirring was continued at 230° C. for 30 minutes in a nitrogen atmosphere to perform a random transesterification reaction. After cooling, the reaction product was transferred to a separatory funnel, separated into layers, and the lower layer was removed. Furthermore, 500 ml of 10% citric acid aqueous solution was added and stirred, and after standing to separate, the upper layer was dehydrated and filtered to obtain a crude diglyceride having a fatty acid composition of rapeseed oil. Furthermore, the crude rapeseed oil fatty acid composition diglyceride was passed through a thin film molecular distillation vessel under conditions of 190° C. and 0.01 mmHg to obtain 165 g of a reaction product containing diglyceride suitable for the present invention. The fatty acid composition and molecular species contained in the obtained reaction product are shown in Tables 1 and 2, respectively. These tables also show the analysis results for rapeseed oil as triglyceride.
【００１６】[0016]
【表１】[Table 1]
【００１７】[0017]
【表２】[Table 2]
【００１８】実施例１
（実験方法）表３の組成の食餌を雄性ｄｄＹ マウスに
１００ 日間投与し、体重変動を追跡した。Example 1 (Experimental Method) A diet having the composition shown in Table 3 was administered to male ddY mice for 100 days, and body weight fluctuations were monitored.
【００１９】[0019]
【表３】[Table 3]
【００２０】（実験結果）得られた結果を表４に示す。(Experimental Results) Table 4 shows the results obtained.
【００２１】[0021]
【表４】[Table 4]
【００２２】表４より、ジグリセリド食群は、トリグリ
セリド食群に比べ、飼料は多く摂取しているにもかかわ
らず、体重は低下しており、ジグリセリドに体重増加抑
制作用があることが明らかとなった。[0022] Table 4 shows that the diglyceride diet group had a lower body weight than the triglyceride diet group even though they ingested more feed, demonstrating that diglyceride has a suppressive effect on weight gain. Ta.
【００２３】実施例２
軟カプセル剤皮組成
ゼラチン
７０．０％ グリセリン
２２．９％
パラオキシ安息香酸メチル
０．
１５％ パラオキシ安息香酸プロピル
０．１５％ 水
適量
計
１００％ 上記成分から成る軟カプセル
剤皮の中に参考例１の製造物 ５００ｍｇ（ジグリセリ
ドとして ３９５ｍｇ含有）を常法により充填し、軟カ
プセル剤を製造した。Example 2 Soft capsule shell composition Gelatin
70.0% glycerin
22.9%
Methyl paraoxybenzoate
0.
15% Propyl paraoxybenzoate
0.15% water
Appropriate amount
Total
500 mg of the product of Reference Example 1 (containing 395 mg as diglyceride) was filled into a soft capsule shell consisting of 100% of the above ingredients by a conventional method to produce a soft capsule.
【００２４】[0024]
【発明の効果】本発明によれば、ジグリセリドを投与す
ることにより、食欲を低下させることなく、体重の増加
を抑制することができる。According to the present invention, weight gain can be suppressed without reducing appetite by administering diglyceride.
Claims (2)
加抑制剤。1. A weight gain suppressant containing diglyceride as an active ingredient.
化１】 〔式中、Ｒ１ 、Ｒ２ 及びＲ３ のうち２個は炭素数
１２〜２２の飽和脂肪酸又は不飽和脂肪酸由来のアシル
基を示し、残余は水素原子を示す〕で表わされる化合物
である請求項１記載の体重増加抑制剤。[Claim 2] The diglyceride has the following general formula (1) [
A claim that the compound is a compound represented by the formula [wherein, two of R1, R2 and R3 represent an acyl group derived from a saturated fatty acid or an unsaturated fatty acid having 12 to 22 carbon atoms, and the remainder represents a hydrogen atom] Item 1. The weight gain inhibitor according to item 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP03064840A JP3098560B2 (en) | 1991-03-28 | 1991-03-28 | Weight gain inhibitor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP03064840A JP3098560B2 (en) | 1991-03-28 | 1991-03-28 | Weight gain inhibitor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04300826A true JPH04300826A (en) | 1992-10-23 |
| JP3098560B2 JP3098560B2 (en) | 2000-10-16 |
Family
ID=13269832
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP03064840A Expired - Lifetime JP3098560B2 (en) | 1991-03-28 | 1991-03-28 | Weight gain inhibitor |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3098560B2 (en) |
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