JPH0761927A - Lipase inhibitor and food and beverage containing the same added thereto - Google Patents
Lipase inhibitor and food and beverage containing the same added theretoInfo
- Publication number
- JPH0761927A JPH0761927A JP21006793A JP21006793A JPH0761927A JP H0761927 A JPH0761927 A JP H0761927A JP 21006793 A JP21006793 A JP 21006793A JP 21006793 A JP21006793 A JP 21006793A JP H0761927 A JPH0761927 A JP H0761927A
- Authority
- JP
- Japan
- Prior art keywords
- lipase
- lipase inhibitor
- flavonoids
- food
- inhibitor
- 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
- 229940086609 Lipase inhibitor Drugs 0.000 title claims abstract description 21
- 235000013305 food Nutrition 0.000 title claims abstract description 17
- 235000013361 beverage Nutrition 0.000 title abstract 3
- 229930003935 flavonoid Natural products 0.000 claims abstract description 19
- 150000002215 flavonoids Chemical class 0.000 claims abstract description 19
- 235000017173 flavonoids Nutrition 0.000 claims abstract description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 abstract description 22
- 108090001060 Lipase Proteins 0.000 abstract description 21
- 102000004882 Lipase Human genes 0.000 abstract description 21
- 239000004367 Lipase Substances 0.000 abstract description 20
- 229940040461 lipase Drugs 0.000 abstract description 20
- 235000019421 lipase Nutrition 0.000 abstract description 20
- 208000008589 Obesity Diseases 0.000 abstract description 10
- 102000019280 Pancreatic lipases Human genes 0.000 abstract description 9
- 108050006759 Pancreatic lipases Proteins 0.000 abstract description 9
- 235000020824 obesity Nutrition 0.000 abstract description 9
- 229940116369 pancreatic lipase Drugs 0.000 abstract description 9
- 238000010521 absorption reaction Methods 0.000 abstract description 7
- 230000029087 digestion Effects 0.000 abstract description 7
- 150000002632 lipids Chemical class 0.000 abstract description 7
- 230000002265 prevention Effects 0.000 abstract description 5
- 239000004480 active ingredient Substances 0.000 abstract description 4
- IKMDFBPHZNJCSN-UHFFFAOYSA-N Myricetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC(O)=C(O)C(O)=C1 IKMDFBPHZNJCSN-UHFFFAOYSA-N 0.000 abstract description 3
- PCOBUQBNVYZTBU-UHFFFAOYSA-N myricetin Natural products OC1=C(O)C(O)=CC(C=2OC3=CC(O)=C(O)C(O)=C3C(=O)C=2)=C1 PCOBUQBNVYZTBU-UHFFFAOYSA-N 0.000 abstract description 3
- 235000007743 myricetin Nutrition 0.000 abstract description 3
- 229940116852 myricetin Drugs 0.000 abstract description 3
- 239000000725 suspension Substances 0.000 abstract description 3
- 239000000654 additive Substances 0.000 abstract description 2
- XADJWCRESPGUTB-UHFFFAOYSA-N apigenin Natural products C1=CC(O)=CC=C1C1=CC(=O)C2=CC(O)=C(O)C=C2O1 XADJWCRESPGUTB-UHFFFAOYSA-N 0.000 abstract description 2
- 235000008714 apigenin Nutrition 0.000 abstract description 2
- KZNIFHPLKGYRTM-UHFFFAOYSA-N apigenin Chemical compound C1=CC(O)=CC=C1C1=CC(=O)C2=C(O)C=C(O)C=C2O1 KZNIFHPLKGYRTM-UHFFFAOYSA-N 0.000 abstract description 2
- 229940117893 apigenin Drugs 0.000 abstract description 2
- 230000002542 deteriorative effect Effects 0.000 abstract description 2
- 238000001035 drying Methods 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract description 2
- 230000001629 suppression Effects 0.000 abstract description 2
- 238000007865 diluting Methods 0.000 abstract 1
- 235000011837 pasties Nutrition 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 244000269722 Thea sinensis Species 0.000 description 7
- WMBWREPUVVBILR-WIYYLYMNSA-N (-)-Epigallocatechin-3-o-gallate Chemical compound O([C@@H]1CC2=C(O)C=C(C=C2O[C@@H]1C=1C=C(O)C(O)=C(O)C=1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 WMBWREPUVVBILR-WIYYLYMNSA-N 0.000 description 6
- WMBWREPUVVBILR-UHFFFAOYSA-N GCG Natural products C=1C(O)=C(O)C(O)=CC=1C1OC2=CC(O)=CC(O)=C2CC1OC(=O)C1=CC(O)=C(O)C(O)=C1 WMBWREPUVVBILR-UHFFFAOYSA-N 0.000 description 6
- REFJWTPEDVJJIY-UHFFFAOYSA-N Quercetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 229940030275 epigallocatechin gallate Drugs 0.000 description 6
- 230000006866 deterioration Effects 0.000 description 5
- 235000009569 green tea Nutrition 0.000 description 5
- MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 description 5
- 235000019626 lipase activity Nutrition 0.000 description 5
- HSHNITRMYYLLCV-UHFFFAOYSA-N 4-methylumbelliferone Chemical compound C1=C(O)C=CC2=C1OC(=O)C=C2C HSHNITRMYYLLCV-UHFFFAOYSA-N 0.000 description 4
- 244000068988 Glycine max Species 0.000 description 4
- 235000010469 Glycine max Nutrition 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- HVQAJTFOCKOKIN-UHFFFAOYSA-N flavonol Natural products O1C2=CC=CC=C2C(=O)C(O)=C1C1=CC=CC=C1 HVQAJTFOCKOKIN-UHFFFAOYSA-N 0.000 description 4
- 235000011957 flavonols Nutrition 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- ZVOLCUVKHLEPEV-UHFFFAOYSA-N Quercetagetin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=C(O)C(O)=C(O)C=C2O1 ZVOLCUVKHLEPEV-UHFFFAOYSA-N 0.000 description 3
- HWTZYBCRDDUBJY-UHFFFAOYSA-N Rhynchosin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=CC(O)=C(O)C=C2O1 HWTZYBCRDDUBJY-UHFFFAOYSA-N 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000003925 fat Substances 0.000 description 3
- 229930003944 flavone Natural products 0.000 description 3
- 150000002213 flavones Chemical class 0.000 description 3
- 235000011949 flavones Nutrition 0.000 description 3
- 150000002216 flavonol derivatives Chemical class 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 235000005875 quercetin Nutrition 0.000 description 3
- 229960001285 quercetin Drugs 0.000 description 3
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 102100024295 Maltase-glucoamylase Human genes 0.000 description 2
- 244000088415 Raphanus sativus Species 0.000 description 2
- 235000006140 Raphanus sativus var sativus Nutrition 0.000 description 2
- 235000006468 Thea sinensis Nutrition 0.000 description 2
- 108010028144 alpha-Glucosidases Proteins 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- XHEFDIBZLJXQHF-UHFFFAOYSA-N fisetin Chemical compound C=1C(O)=CC=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 XHEFDIBZLJXQHF-UHFFFAOYSA-N 0.000 description 2
- 229930182470 glycoside Natural products 0.000 description 2
- 150000002338 glycosides Chemical class 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- CJWQYWQDLBZGPD-UHFFFAOYSA-N isoflavone Natural products C1=C(OC)C(OC)=CC(OC)=C1C1=COC2=C(C=CC(C)(C)O3)C3=C(OC)C=C2C1=O CJWQYWQDLBZGPD-UHFFFAOYSA-N 0.000 description 2
- 235000008696 isoflavones Nutrition 0.000 description 2
- IYRMWMYZSQPJKC-UHFFFAOYSA-N kaempferol Chemical compound C1=CC(O)=CC=C1C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1 IYRMWMYZSQPJKC-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- UXOUKMQIEVGVLY-UHFFFAOYSA-N morin Natural products OC1=CC(O)=CC(C2=C(C(=O)C3=C(O)C=C(O)C=C3O2)O)=C1 UXOUKMQIEVGVLY-UHFFFAOYSA-N 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 102000002260 Alkaline Phosphatase Human genes 0.000 description 1
- 108020004774 Alkaline Phosphatase Proteins 0.000 description 1
- 235000000832 Ayote Nutrition 0.000 description 1
- 240000004160 Capsicum annuum Species 0.000 description 1
- 235000008534 Capsicum annuum var annuum Nutrition 0.000 description 1
- 240000004244 Cucurbita moschata Species 0.000 description 1
- 235000009854 Cucurbita moschata Nutrition 0.000 description 1
- 235000009804 Cucurbita pepo subsp pepo Nutrition 0.000 description 1
- UBSCDKPKWHYZNX-UHFFFAOYSA-N Demethoxycapillarisin Natural products C1=CC(O)=CC=C1OC1=CC(=O)C2=C(O)C=C(O)C=C2O1 UBSCDKPKWHYZNX-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 244000194101 Ginkgo biloba Species 0.000 description 1
- 235000008100 Ginkgo biloba Nutrition 0.000 description 1
- PSJQCAMBOYBQEU-UHFFFAOYSA-N Glyoxalase I Natural products CC=CC(=O)OCC1=CC(O)C(O)C(O)C1=O PSJQCAMBOYBQEU-UHFFFAOYSA-N 0.000 description 1
- 201000005569 Gout Diseases 0.000 description 1
- 240000001080 Grifola frondosa Species 0.000 description 1
- 235000007710 Grifola frondosa Nutrition 0.000 description 1
- 229920002488 Hemicellulose Polymers 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 102000014017 Lactoylglutathione lyase Human genes 0.000 description 1
- 108010050765 Lactoylglutathione lyase Proteins 0.000 description 1
- 229940127470 Lipase Inhibitors Drugs 0.000 description 1
- YXOLAZRVSSWPPT-UHFFFAOYSA-N Morin Chemical compound OC1=CC(O)=CC=C1C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1 YXOLAZRVSSWPPT-UHFFFAOYSA-N 0.000 description 1
- 244000170916 Paeonia officinalis Species 0.000 description 1
- 235000006484 Paeonia officinalis Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 244000134552 Plantago ovata Species 0.000 description 1
- 235000003421 Plantago ovata Nutrition 0.000 description 1
- 240000001462 Pleurotus ostreatus Species 0.000 description 1
- 239000009223 Psyllium Substances 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 108010093894 Xanthine oxidase Proteins 0.000 description 1
- 102100033220 Xanthine oxidase Human genes 0.000 description 1
- 230000003579 anti-obesity Effects 0.000 description 1
- 235000019606 astringent taste Nutrition 0.000 description 1
- 229960000074 biopharmaceutical Drugs 0.000 description 1
- 235000020279 black tea Nutrition 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 208000002925 dental caries Diseases 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 108010042194 dextransucrase Proteins 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 229940088598 enzyme Drugs 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 235000011990 fisetin Nutrition 0.000 description 1
- 150000007946 flavonol Chemical class 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 description 1
- 229960000367 inositol Drugs 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- GOMNOOKGLZYEJT-UHFFFAOYSA-N isoflavone Chemical compound C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC=C1 GOMNOOKGLZYEJT-UHFFFAOYSA-N 0.000 description 1
- 150000002515 isoflavone derivatives Chemical class 0.000 description 1
- 235000008777 kaempferol Nutrition 0.000 description 1
- LRDGATPGVJTWLJ-UHFFFAOYSA-N luteolin Natural products OC1=CC(O)=CC(C=2OC3=CC(O)=CC(O)=C3C(=O)C=2)=C1 LRDGATPGVJTWLJ-UHFFFAOYSA-N 0.000 description 1
- 235000009498 luteolin Nutrition 0.000 description 1
- IQPNAANSBPBGFQ-UHFFFAOYSA-N luteolin Chemical compound C=1C(O)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(O)C(O)=C1 IQPNAANSBPBGFQ-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 235000007708 morin Nutrition 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000020333 oolong tea Nutrition 0.000 description 1
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 1
- 235000015108 pies Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 229940070687 psyllium Drugs 0.000 description 1
- 235000015136 pumpkin Nutrition 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 108010079522 solysime Proteins 0.000 description 1
- 235000018553 tannin Nutrition 0.000 description 1
- 229920001864 tannin Polymers 0.000 description 1
- 239000001648 tannin Substances 0.000 description 1
- 235000019640 taste Nutrition 0.000 description 1
- 235000013616 tea Nutrition 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 235000015099 wheat brans Nutrition 0.000 description 1
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、リパーゼ阻害剤に関
し、更に詳しくは、生体内で脂質の消化吸収に関与する
膵リパーゼを有効に阻害して、肥満の抑制や予防に寄与
し得る安全性の高いリパーゼ阻害剤に関する。また、こ
のリパーゼ阻害剤は、リパーゼに起因する飲食品等の劣
化や悪臭発生の防止に利用することができる。FIELD OF THE INVENTION The present invention relates to a lipase inhibitor, and more specifically, it can effectively inhibit pancreatic lipase involved in digestion and absorption of lipids in vivo and contribute to suppression and prevention of obesity. High lipase inhibitor. Further, this lipase inhibitor can be used for preventing deterioration of foods and drinks and generation of malodor due to lipase.
【０００２】[0002]
【従来の技術】ヒトにおいて、リパーゼ（膵リパーゼ）
は、脂質の消化吸収の最初の酵素であり、膵リパーゼを
阻害して、肥満症を抑制したり予防する薬剤の開発が既
に試みられている。例えば、特開昭５５−９８１１４号
に記載された抗肥満及びトリグリセリド減少剤、特開昭
６１−１５２６６３号に記載されたオキセタノン類およ
び特開平１−１０２０２２号に記載された肥満予防剤等
を例示することができる。2. Description of the Related Art Lipase (pancreatic lipase) in humans
Is the first enzyme for digestion and absorption of lipids, and development of a drug for inhibiting or preventing obesity by inhibiting pancreatic lipase has already been attempted. Examples include anti-obesity and triglyceride reducing agents described in JP-A-55-98114, oxetanones described in JP-A-61-252663, and obesity-preventing agents described in JP-A-1-102022. can do.
【０００３】また、同様の目的で、穀類、豆類から分離
した阻害物質を添加した飲食品（特開昭６４−３４２６
４号）や、脂肪に富んだ種子からの阻害物質の抽出法
（特開昭４９−４１５８０号）等が開示されている。For the same purpose, foods and drinks to which an inhibitor separated from cereals and beans is added (Japanese Patent Laid-Open No. 3426/1988).
No. 4) and a method for extracting an inhibitory substance from seeds rich in fat (JP-A-49-41580).
【０００４】一方、飼い葉（Ｆｏｄｄｅｒ ｐｌａｎ
ｔ）のタンニン類が、リパーゼを阻害することが知られ
ている（Ｂｒｉｔｉｓｈ Ｊ． Ｎｕｔｒｉｔｉｏｎ，
６０，２７５（１９８８））。また、大豆や穀類、大根
種子からの蛋白質が、これを阻害することが報告されて
いる（Ａｇｒｉｃ． Ｂｉｏｌ． Ｃｈｅｍ．，３７，
１２２５，（１９７３）、Ｎｕｒｔ． Ｒｅｐ． Ｉｎ
ｔ．，３２，１１０７（１９８５）、日本食品工業会
誌、３５，４３０（１９８８））。また、ヘミセルロー
スや小麦ふすま等（Ｊ． Ｆｏｏｄ Ｓｃｉ．，４９，
９５６（１９８４）、Ａｍ． Ｊ．Ｃｌｉｎ． Ｎｕｔ
ｒ．，４２，６２９（１９８５））、大根種子のフォス
ファチジルコリン（明治大学農学部研究報告、７３、９
（１９８６））、ミオイノシトール（Ｊ． Ｆｏｏｄ
Ｓｃｉ．，５３，２５０（１９８８））等によるリパー
ゼ阻害に関する報告がある。On the other hand, fodder plan
The tannins of t) are known to inhibit lipase (British J. Nutrition,
60 , 275 (1988)). In addition, proteins from soybeans, cereals, and radish seeds have been reported to inhibit this (Agric. Biol. Chem., 37 , 37) .
1225 (1973), Nurt. Rep. In
t. , 32 , 1107 (1985), Japan Food Manufacturers Association, 35, 430 (1988)). In addition, hemicellulose, wheat bran and the like (J. Food Sci., 49 ,
956 (1984), Am. J. Clin. Nut
r. , 42, 629 (1985)), phosphatidylcholine of radish seeds (Faculty of Agriculture, Meiji University, 73 , 9)
(1986)), myo-inositol (J. Food).
Sci. , 53 , 250 (1988)) and the like, and reports on lipase inhibition.
【０００５】生薬類については、微生物リパーゼに対す
るものとして、シャクヤク、オオレン、オオバク、ボタ
ンビ、ゲンノショウコ、茶等の１４種の生薬の抽出物が
開示されている（特開昭６４−９０１３１号）。また、
各種天然物抽出物に関して、リパーゼ阻害作用を調べた
結果が報告されている（明治大学農学部研究報告、６
９、１５（１９８５））。Regarding crude drugs, as extracts against microbial lipase, extracts of 14 kinds of crude drugs such as peony, oren, psyllium, button pie, ginkgo biloba, and tea have been disclosed (JP-A-64-90131). Also,
The results of investigating the lipase inhibitory action of various natural product extracts have been reported (Meiji University Faculty of Agriculture, Research Report, 6
9 , 15 (1985)).
【０００６】更に、最近では、ピーマン、かぼちゃ、し
めじ、まいたけ、ひじき、緑茶、紅茶、ウーロン茶の水
抽出物からなるリパーゼ阻害剤（特開平３−２１９８７
２号）および緑茶中の主要な成分であるエピガロカテキ
ンガレートを配合することを特徴とする脂質吸収抑制食
品に関する特許（特開平３−２２８６６４号）が公示さ
れている。Further, recently, a lipase inhibitor comprising a water extract of bell pepper, pumpkin, shimeji mushrooms, maitake mushrooms, hijiki, green tea, black tea, and oolong tea (JP-A-3-21987).
No. 2) and epigallocatechin gallate, which is a main component in green tea, are incorporated into the patent (JP-A-3-228664) concerning a lipid absorption-suppressing food.
【０００７】一方、フラボノイド類に関しては、肥満や
糖尿病予防を目的として、ラット小腸α−グルコシダー
ゼに対するフラボン類の影響が調べられており、ミリセ
チンや合成のフラボン類に阻害効果があることが報告さ
れている（Ｃｈｅｍ．Ｐｈａｒｍ．Ｂｕｌｌ．，３４，
８３８（１９８６））。また、虫歯予防を目的として、
フラボノール類であるケルセチンがＳ．Ｍｕｔａｎｓデ
キストランシュクラーゼを阻害することが報告されてい
る（Ａｇｒｉｃ．Ｂｉｏｌ．Ｃｈｅｍ．，４８，２１４
３（１９８４））。また、炎症反応に関与するグリオキ
サラーゼＩの活性をケルセチン、フィセチン、モリン、
ミリセチン等のフラボノール類が阻害すること（農化
誌、５７、７６５（１９８３））、また痛風に関与する
とされるキサンチンオキシダーゼに対し、アピゲニン、
ルテオリンのフラボン類およびその一部の配糖体、並び
にケンフェロールおよびケルセチンなどのフラボノール
類およびその配糖体による阻害が報告されている（生薬
学雑誌、４１、１１６（１９８７））。その他、酵母α
−グルコシダーゼ（Ａｇｒｉｃ．Ｂｉｏｌ．Ｃｈｅ
ｍ．，４８，１５５９（１９８４））、アルカリ性フォ
スファターゼ（農化誌、５４、１７１（１９８０））に
対する作用が報告されている。On the other hand, regarding flavonoids, the effects of flavones on rat small intestinal α-glucosidase have been investigated for the purpose of preventing obesity and diabetes, and it has been reported that myricetin and synthetic flavones have an inhibitory effect. (Chem. Pharm. Bull., 34 ,
838 (1986)). In addition, for the purpose of preventing tooth decay,
Quercetin which is a flavonol is S. It has been reported to inhibit Mutans dextran sucrase (Agric. Biol. Chem., 48 , 214.
3 (1984)). In addition, the activity of glyoxalase I, which is involved in inflammatory reaction, was evaluated by quercetin, fisetin, morin,
Inhibition of flavonols such as myricetin (Agricultural Journal, 57 , 765 (1983)), and xanthine oxidase, which is considered to be involved in gout, against apigenin,
Inhibition of luteolin by flavones and some glycosides thereof and flavonols such as kaempferol and quercetin and their glycosides has been reported (Biopharmaceutical Journal, 41 , 116 (1987)). Others, yeast α
-Glucosidase (Agric. Biol. Che
m. , 48 , 1559 (1984)), and an action against alkaline phosphatase (Agricultural Journal, 54 , 171 (1980)).
【０００８】リパーゼに対するフラボノイド類の効果に
ついては、大豆のイソフラボンに関する研究のみであ
り、この場合大豆イソフラボンが大豆発芽のリパーゼを
阻害するが、膵臓リパーゼに対しては弱い阻害を示すこ
とが報告されているのみである（熊本女大学紀要、３
３、６０（１９８１））。Regarding the effect of flavonoids on lipase, only studies on soybean isoflavones have been reported, in which soybean isoflavone inhibits soybean germination lipase but weakly inhibits pancreatic lipase. Only (Bulletin of Kumamoto Women's University, 3
3 , 60 (1981)).
【０００９】以上のように、フラボノイド類に関する報
告は多数あるが、本発明のフラボノイド類がリパーゼ阻
害効果を有することを記載した文献はない。As described above, although there are many reports on flavonoids, there is no reference that the flavonoids of the present invention have a lipase inhibitory effect.
【００１０】[0010]
【発明が解決しようとする課題】本発明は、生体内で脂
質の消化吸収を司り、肥満症の鍵を握る膵リパーゼに対
して著しく高い阻害作用を示し、これを阻害して肥満の
抑制や予防に寄与し得ると共に、リパーゼに起因する食
品等の劣化や悪臭発生の防止に利用することができる安
全性の高いリパーゼ阻害剤およびこれを添加した飲食品
を提供することを目的とする。The present invention controls digestion and absorption of lipids in vivo and exhibits a remarkably high inhibitory effect on pancreatic lipase, which is a key to obesity. It is an object of the present invention to provide a highly safe lipase inhibitor that can contribute to prevention and can be used for preventing deterioration of foods and the like caused by lipase and generation of malodor, and foods and drinks to which the lipase inhibitor is added.
【００１１】安全性が高い天然成分について、リパーゼ
活性の阻害効果を有する成分を多年にわたり広く探索し
た結果、式（１）で示されるフラボノイド類に高いリパ
ーゼ阻害効果のあることを突き止めるに至った。[0011] As a result of extensively searching for a highly safe natural component for a component having an inhibitory effect on lipase activity for many years, it has been found that the flavonoids represented by the formula (1) have a high lipase inhibitory effect.
【００１２】[0012]
【課題を解決するための手段】本発明によれば、リパー
ゼ阻害剤の有効成分として、式（１）According to the present invention, the formula (1) is used as an active ingredient of a lipase inhibitor.
【００１３】[0013]
【化２】 [Chemical 2]
【００１４】（式中、Ｒ１、Ｒ２およびＲ３は、各々独
立して、水素原子またはヒドロキシル基を示す。）で示
されるフラボノイド類を含有することを特徴とするリパ
ーゼ阻害剤が提供される。There is provided a lipase inhibitor characterized by containing flavonoids represented by the formula: wherein R 1 , R 2 and R 3 each independently represent a hydrogen atom or a hydroxyl group. It
【００１５】これらのフラボノイド類は、単品または数
種を混合して使用することができる。また、これらのフ
ラボノイド類は、そのままで、あるいは適切な溶媒で希
釈した溶液もしくは懸濁液として使用することができ
る。さらに、混合、乾燥等の通常の操作により、他の添
加物と配合して粉末状あるいはペースト状として使用す
ることができる。These flavonoids can be used individually or as a mixture of several kinds. In addition, these flavonoids can be used as they are or as a solution or suspension diluted with an appropriate solvent. Furthermore, it can be used in the form of powder or paste by mixing with other additives by a usual operation such as mixing and drying.
【００１６】これらのフラボノイド類は、適宜製剤化し
て、リパーゼ阻害剤として使用することができる。ま
た、飲食品等に予め添加、混合して使用することができ
る。さらに、これらのフラボノイドは、適宜配糖化して
使用することも可能である。These flavonoids can be used as a lipase inhibitor after being appropriately formulated. In addition, it can be used by adding it to foods and drinks and mixing it in advance. Furthermore, these flavonoids can be appropriately glycosylated before use.
【００１７】[0017]
【作用】これらのフラボノイド類は、従来よりリパーゼ
阻害作用が高いとされる緑茶成分のエピガロカテキンガ
レートよりも阻害効果が高く、かつ天然の植物由来のも
のであるため安全性の高いリパーゼ阻害剤を提供するこ
とができる。[Effect] These flavonoids have a higher inhibitory effect than epigallocatechin gallate, which is a green tea ingredient which is said to have a higher lipase inhibitory effect than before, and is a highly safe lipase inhibitor because it is derived from natural plants. Can be provided.
【００１８】これらのリパーゼ阻害剤は、油脂の消化吸
収の阻害に基く肥満予防に利用することができ、またリ
パーゼに起因する食品等の劣化、悪臭の発生の防止に利
用することができる。These lipase inhibitors can be used for obesity prevention based on the inhibition of digestion and absorption of fats and oils, and can be used for preventing deterioration of foods and the like and generation of malodor due to lipase.
【００１９】[0019]
【実施例】以下、実施例により本発明を更に詳細に説明
するが、本発明は以下の実施例にのみ限定されるもので
はない。The present invention will be described in more detail with reference to the following examples, but the present invention is not limited to the following examples.
【００２０】実施例１（リパーゼ活性測定法） リパーゼ活性の測定は、基質に蛍光性の４−メチルウン
ベリフェロンのオレイン酸エステル（４−ＭＵＯ）を使
用し、反応によって生成した４−メチルウンベリフェロ
ンの蛍光を測定することによって行った。 Example 1 (Method for measuring lipase activity ) Lipase activity was measured by using 4-methylumbelliferone oleate (4-MUO), which is a fluorescent substance, as a substrate. This was done by measuring the fluorescence of beryferon.
【００２１】小試験管に、基質である４−ＭＵＯ懸濁液
１００μｌ、ブタ膵リパーゼ（Ｓｉｇｍａ社製）溶液５
０μｌ、緩衝液５０μｌを採り、最終的に４−ＭＵＯ
０．０５ｍＭ、ブタ膵リパーゼ２．２μｇ、Ｍｃｌｌｖ
ａｉｎｅ緩衝液（ｐＨ７．４）の条件で、３７℃で２０
分間反応させた。０．１Ｎ塩酸１ｍｌを添加して反応を
停止させ、０．１Ｍクエン酸ナトリウムを２ｍｌ添加し
て、溶液のｐＨを４．３付近とした後、反応によって生
成した４−メチルウンベリフェロンの蛍光（励起波長３
２０ｎｍ、蛍光波長４５０ｎｍ）を、蛍光光度計により
測定した。In a small test tube, 100 μl of 4-MUO suspension which is a substrate, and porcine pancreatic lipase (manufactured by Sigma) solution 5
Take 0 μl and 50 μl of buffer, and finally 4-MUO
0.05 mM, porcine pancreatic lipase 2.2 μg, Mclv
20 at 37 ° C under the condition of aine buffer (pH 7.4)
Let react for minutes. The reaction was stopped by adding 1 ml of 0.1 N hydrochloric acid, and 2 ml of 0.1 M sodium citrate was added to adjust the pH of the solution to around 4.3, and then fluorescence of 4-methylumbelliferone produced by the reaction (Excitation wavelength 3
20 nm, fluorescence wavelength 450 nm) was measured with a fluorimeter.
【００２２】実施例２（リパーゼ阻害効果の測定） リパーゼ活性に及ぼす試料の阻害効果の測定は、実施例
１に示したリパーゼ活性の測定系に試料を添加して反応
させ、活性に対する影響を調べることにより行った。 Example 2 (Measurement of lipase inhibitory effect) The inhibitory effect of the sample on the lipase activity was measured by adding the sample to the lipase activity measuring system shown in Example 1 and allowing the reaction to examine the effect on the activity. I went by.
【００２３】各試料は、５０％テトラヒドロフラン（Ｔ
ＨＦ）に溶解し、実施例１に示した反応系のＭｃｌｌｖ
ａｉｎｅ緩衝液５μｌの代りに、試料の５０％ＴＨＦ溶
液の５μｌを添加して反応させた。対照は、５０％ＴＨ
Ｆを５μｌを添加して同様に反応させた。阻害活性は、
試料無添加の対照の活性を半分にする試料添加量（ＩＣ
５０（μｇ））で示した。Each sample contained 50% tetrahydrofuran (T
HF) and dissolved in the reaction system shown in Example 1
Instead of 5 μl of aine buffer, 5 μl of 50% THF solution of the sample was added and reacted. Control is 50% TH
5 μl of F was added and reacted in the same manner. The inhibitory activity is
Amount of added sample (IC
50 (μg)).
【００２４】実施例３（フラボノイド類の阻害効果） 上記の実施例に従って、本発明のフラボノイド類のリパ
ーゼ阻害効果を調べた。その結果を表１に示す。 Example 3 (Inhibitory effect of flavonoids) The inhibitory effect of the flavonoids of the present invention on lipase was examined according to the above-mentioned Example. The results are shown in Table 1.
【００２５】[0025]
【表１】 [Table 1]
【００２６】[0026]
【化３】 [Chemical 3]
【００２７】緑茶の主成分であるエピガロカテキンガレ
ートは、リパーゼ阻害効果が高いことが知られている
が、本発明のフラボノール類には、エピガロカテキンガ
レートよりも明らかに高い阻害効果が認められた。It is known that epigallocatechin gallate, which is the main component of green tea, has a high lipase inhibitory effect, but the flavonols of the present invention have a significantly higher inhibitory effect than epigallocatechin gallate. It was
【００２８】[0028]
【発明の効果】本発明によれば、生体内で脂質の消化吸
収を司り、肥満症の鍵を握る膵リパーゼに対して著しく
高い阻害作用を示し、これを阻害して肥満の抑制や予防
に寄与し得ると共に、リパーゼに起因する食品等の劣化
や悪臭発生の防止に利用することができる安全性の高い
リパーゼ阻害剤が提供される。INDUSTRIAL APPLICABILITY According to the present invention, it exerts a remarkably high inhibitory effect on pancreatic lipase, which controls digestion and absorption of lipids in vivo and plays a key role in obesity, and inhibits this to suppress or prevent obesity. Provided is a highly safe lipase inhibitor which can contribute to the deterioration of foods and the like caused by lipase and the prevention of offensive odor.
【００２９】本発明による、フラボノイド類を有効成分
とするリパーゼ阻害剤は、リパーゼ阻害活性が知られて
いる緑茶成分エピガロカテキンガレートよりもリパーゼ
阻害効果が高く、消化酵素リパーゼの働きを阻害し、脂
質の消化吸収を抑制し、脂肪摂取による肥満を予防する
ことができる。。The lipase inhibitor containing flavonoids as an active ingredient according to the present invention has a higher lipase inhibitory effect than the green tea ingredient epigallocatechin gallate, which has a known lipase inhibitory activity, and inhibits the action of the digestive enzyme lipase, It is possible to suppress digestion and absorption of lipids and prevent obesity due to fat intake. .
【００３０】本発明による、フラボノイド類を有効成分
とするリパーゼ阻害剤は、エピガロカテキンガレートの
ような著しい渋みはなく、食品などの味を劣化させるこ
となく、添加、配合、することができる。また、日常摂
取している野菜類や飲料にも少量含まれており、安全性
が高いリパーゼ阻害物質である。さらに、リパーゼに起
因する食品の劣化、悪臭の発生の防止にも利用すること
ができる。The lipase inhibitor containing flavonoids as an active ingredient according to the present invention does not have a marked astringency like epigallocatechin gallate and can be added or blended without deteriorating the taste of food or the like. In addition, it is a highly safe lipase inhibitor that is contained in a small amount in vegetables and drinks that are ingested daily. Further, it can be used for preventing deterioration of foods and generation of malodor due to lipase.
フロントページの続き (72)発明者 志村 進 埼玉県浦和市沼影１−23−６ (72)発明者 伊東 禧男 東京都清瀬市野塩３−26−11Front Page Continuation (72) Inventor Susumu Shimura 1-23-6 Numakage, Urawa-shi, Saitama (72) Ino Yoshio 3-26-11 Noshio, Kiyose-shi, Tokyo
Claims (2)
（１） 【化１】 （式中、Ｒ１、Ｒ２およびＲ３は、各々独立して、水素
原子またはヒドロキシル基を示す。）で示されるフラボ
ノイド類を含有することを特徴とするリパーゼ阻害剤。1. A compound represented by the formula (1): (In the formula, R 1 , R 2 and R 3 each independently represent a hydrogen atom or a hydroxyl group.) A lipase inhibitor characterized by containing a flavonoid.
混合してなることを特徴とする飲食品。2. A lipase inhibitor according to claim 1 is added,
Food and drink characterized by being mixed.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21006793A JP2598873B2 (en) | 1993-08-25 | 1993-08-25 | Lipase inhibitor and food and drink to which it is added |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21006793A JP2598873B2 (en) | 1993-08-25 | 1993-08-25 | Lipase inhibitor and food and drink to which it is added |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0761927A true JPH0761927A (en) | 1995-03-07 |
| JP2598873B2 JP2598873B2 (en) | 1997-04-09 |
Family
ID=16583277
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP21006793A Expired - Lifetime JP2598873B2 (en) | 1993-08-25 | 1993-08-25 | Lipase inhibitor and food and drink to which it is added |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2598873B2 (en) |
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| US7939559B2 (en) | 2004-07-05 | 2011-05-10 | Suntory Holdings Limited | Lipase inhibitors |
| WO2006004110A1 (en) * | 2004-07-05 | 2006-01-12 | Suntory Limited | Lipase inhibitor |
| JP2006016367A (en) * | 2004-07-05 | 2006-01-19 | Suntory Ltd | Lipase inhibitor |
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| US7754695B2 (en) | 2004-08-23 | 2010-07-13 | Suntory Holdings Limited | Lipase inhibitors |
| WO2006135084A1 (en) * | 2005-06-14 | 2006-12-21 | Kurume University | Prophylactic or therapeutic agent for steatohepatitis or fatty liver |
| WO2006135083A1 (en) * | 2005-06-14 | 2006-12-21 | Kurume University | Prophylactic or therapeutic agent for visceral fat syndrome |
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| KR20150014410A (en) * | 2014-11-18 | 2015-02-06 | 경북대학교 산학협력단 | Anti-thrombotic composition comprising phenol compound |
| CN106261405A (en) * | 2016-08-24 | 2017-01-04 | 开平市水口镇卡摩商行 | A kind of health beverage |
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