JP2815136B2 - Food and drink containing lignan glycosides - Google Patents
Food and drink containing lignan glycosidesInfo
- Publication number
- JP2815136B2 JP2815136B2 JP7148278A JP14827895A JP2815136B2 JP 2815136 B2 JP2815136 B2 JP 2815136B2 JP 7148278 A JP7148278 A JP 7148278A JP 14827895 A JP14827895 A JP 14827895A JP 2815136 B2 JP2815136 B2 JP 2815136B2
- Authority
- JP
- Japan
- Prior art keywords
- lignan
- water
- glycoside
- food
- soluble
- 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.)
- Expired - Lifetime
Links
- 229930013686 lignan Natural products 0.000 title claims description 87
- 235000009408 lignans Nutrition 0.000 title claims description 87
- -1 lignan glycosides Chemical class 0.000 title claims description 84
- 229930182470 glycoside Natural products 0.000 title claims description 79
- 235000013305 food Nutrition 0.000 title claims description 24
- 241000207961 Sesamum Species 0.000 claims description 45
- 235000003434 Sesamum indicum Nutrition 0.000 claims description 45
- 239000000126 substance Substances 0.000 claims description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 27
- 239000000284 extract Substances 0.000 claims description 17
- 150000005692 lignans Chemical class 0.000 claims description 17
- 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 claims description 15
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims description 12
- KQRXQIPRDKVZPW-UHFFFAOYSA-N sesaminol Natural products C1=C2OCOC2=CC(C2OCC3C2COC3C2=CC=3OCOC=3C=C2O)=C1 KQRXQIPRDKVZPW-UHFFFAOYSA-N 0.000 claims description 12
- KQRXQIPRDKVZPW-ISZNXKAUSA-N sesaminol Chemical group C1=C2OCOC2=CC([C@H]2OC[C@H]3[C@@H]2CO[C@@H]3C2=CC=3OCOC=3C=C2O)=C1 KQRXQIPRDKVZPW-ISZNXKAUSA-N 0.000 claims description 11
- 239000008103 glucose Substances 0.000 claims description 7
- IJZGFTCXUSMUHI-UHFFFAOYSA-N sesaminol triglucoside Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(OC2C(C(O)C(O)C(CO)O2)O)C(OC=2C(=CC=3OCOC=3C=2)C2C3C(C(OC3)C=3C=C4OCOC4=CC=3)CO2)O1 IJZGFTCXUSMUHI-UHFFFAOYSA-N 0.000 claims description 7
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical group OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 claims description 5
- 229930182830 galactose Chemical group 0.000 claims description 5
- 229930091371 Fructose Chemical group 0.000 claims description 4
- 239000005715 Fructose Chemical group 0.000 claims description 4
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical group OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 claims description 4
- 239000012141 concentrate Substances 0.000 claims description 2
- 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 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 239000008280 blood Substances 0.000 description 22
- 210000004369 blood Anatomy 0.000 description 22
- 238000000034 method Methods 0.000 description 22
- 239000000047 product Substances 0.000 description 21
- 239000000203 mixture Substances 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 150000002632 lipids Chemical class 0.000 description 14
- 230000007935 neutral effect Effects 0.000 description 12
- 239000003921 oil Substances 0.000 description 10
- 235000019198 oils Nutrition 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 235000012000 cholesterol Nutrition 0.000 description 8
- 150000002338 glycosides Chemical class 0.000 description 8
- 239000000399 hydroalcoholic extract Substances 0.000 description 8
- 235000000346 sugar Nutrition 0.000 description 7
- 239000000469 ethanolic extract Substances 0.000 description 6
- 230000035784 germination Effects 0.000 description 6
- 239000012535 impurity Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- OJVGWDJIYBTWDS-UHFFFAOYSA-N Sesamolinol Natural products C1=C(O)C(OC)=CC(OC2C3C(C(OC3)C=3C=C4OCOC4=CC=3)CO2)=C1 OJVGWDJIYBTWDS-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000003925 fat Substances 0.000 description 5
- 235000019197 fats Nutrition 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- OHOPKHNWLCMLSW-UHFFFAOYSA-N pinoresinol Natural products C1=C(O)C(OC)=CC(C2C3C(C(OC3)C=3C=C(CO)C(O)=CC=3)CO2)=C1 OHOPKHNWLCMLSW-UHFFFAOYSA-N 0.000 description 5
- 235000007221 pinoresinol Nutrition 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- BURBOJZOZGMMQF-UHFFFAOYSA-N xanthoxylol Natural products C1=C(O)C(OC)=CC=C1C1C(COC2C=3C=C4OCOC4=CC=3)C2CO1 BURBOJZOZGMMQF-UHFFFAOYSA-N 0.000 description 5
- HGXBRUKMWQGOIE-AFHBHXEDSA-N (+)-pinoresinol Chemical compound C1=C(O)C(OC)=CC([C@@H]2[C@@H]3[C@@H]([C@H](OC3)C=3C=C(OC)C(O)=CC=3)CO2)=C1 HGXBRUKMWQGOIE-AFHBHXEDSA-N 0.000 description 4
- TWCMVXMQHSVIOJ-UHFFFAOYSA-N Aglycone of yadanzioside D Natural products COC(=O)C12OCC34C(CC5C(=CC(O)C(O)C5(C)C3C(O)C1O)C)OC(=O)C(OC(=O)C)C24 TWCMVXMQHSVIOJ-UHFFFAOYSA-N 0.000 description 4
- PLMKQQMDOMTZGG-UHFFFAOYSA-N Astrantiagenin E-methylester Natural products CC12CCC(O)C(C)(CO)C1CCC1(C)C2CC=C2C3CC(C)(C)CCC3(C(=O)OC)CCC21C PLMKQQMDOMTZGG-UHFFFAOYSA-N 0.000 description 4
- 235000010469 Glycine max Nutrition 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 102220547770 Inducible T-cell costimulator_A23L_mutation Human genes 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- OJVGWDJIYBTWDS-AFHBHXEDSA-N Sesamolinol Chemical compound C1=C(O)C(OC)=CC(O[C@@H]2[C@@H]3[C@@H]([C@H](OC3)C=3C=C4OCOC4=CC=3)CO2)=C1 OJVGWDJIYBTWDS-AFHBHXEDSA-N 0.000 description 4
- 230000003078 antioxidant effect Effects 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 235000014121 butter Nutrition 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- PFOARMALXZGCHY-UHFFFAOYSA-N homoegonol Natural products C1=C(OC)C(OC)=CC=C1C1=CC2=CC(CCCO)=CC(OC)=C2O1 PFOARMALXZGCHY-UHFFFAOYSA-N 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000012264 purified product Substances 0.000 description 4
- 235000013322 soy milk Nutrition 0.000 description 4
- ACLBTXLOASZGRX-UHFFFAOYSA-N 2-(2,3-dihydro-1,4-benzodioxin-5-yloxy)-n,n-diethylethanamine;hydrochloride Chemical compound Cl.O1CCOC2=C1C=CC=C2OCCN(CC)CC ACLBTXLOASZGRX-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 244000068988 Glycine max Species 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 235000010746 mayonnaise Nutrition 0.000 description 3
- 239000008268 mayonnaise Substances 0.000 description 3
- 235000012054 meals Nutrition 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 208000031226 Hyperlipidaemia Diseases 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 240000008415 Lactuca sativa Species 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 239000006004 Quartz sand Substances 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000012675 alcoholic extract Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 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 2
- 238000009395 breeding Methods 0.000 description 2
- 230000001488 breeding effect Effects 0.000 description 2
- 150000001720 carbohydrates Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 235000015071 dressings Nutrition 0.000 description 2
- 239000003651 drinking water Substances 0.000 description 2
- 235000020188 drinking water Nutrition 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 235000012041 food component Nutrition 0.000 description 2
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000000787 lecithin Substances 0.000 description 2
- 235000010445 lecithin Nutrition 0.000 description 2
- 229940067606 lecithin Drugs 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 235000013310 margarine Nutrition 0.000 description 2
- 239000003264 margarine Substances 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 239000004570 mortar (masonry) Substances 0.000 description 2
- 150000003904 phospholipids Chemical class 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 235000012045 salad Nutrition 0.000 description 2
- 235000014438 salad dressings Nutrition 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 229940033331 soy sterol Drugs 0.000 description 2
- 239000003549 soybean oil Substances 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- 238000006227 trimethylsilylation reaction Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 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 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- 239000004278 EU approved seasoning Substances 0.000 description 1
- 102000002322 Egg Proteins Human genes 0.000 description 1
- 108010000912 Egg Proteins Proteins 0.000 description 1
- 241000220225 Malus Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229930182558 Sterol Natural products 0.000 description 1
- MSCCTZZBYHQMQJ-AZAGJHQNSA-N Tocopheryl nicotinate Chemical compound C([C@@](OC1=C(C)C=2C)(C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)CC1=C(C)C=2OC(=O)C1=CC=CN=C1 MSCCTZZBYHQMQJ-AZAGJHQNSA-N 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- OENHQHLEOONYIE-UKMVMLAPSA-N all-trans beta-carotene Natural products CC=1CCCC(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C OENHQHLEOONYIE-UKMVMLAPSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 235000015197 apple juice Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 208000011775 arteriosclerosis disease Diseases 0.000 description 1
- TUPZEYHYWIEDIH-WAIFQNFQSA-N beta-carotene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C)C=CC=C(/C)C=CC2=CCCCC2(C)C TUPZEYHYWIEDIH-WAIFQNFQSA-N 0.000 description 1
- 235000013734 beta-carotene Nutrition 0.000 description 1
- 239000011648 beta-carotene Substances 0.000 description 1
- 229960002747 betacarotene Drugs 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 235000014171 carbonated beverage Nutrition 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 229960000633 dextran sulfate Drugs 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 235000013345 egg yolk Nutrition 0.000 description 1
- 210000002969 egg yolk Anatomy 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- PEYUIKBAABKQKQ-UHFFFAOYSA-N epiasarinin Natural products C1=C2OCOC2=CC(C2OCC3C2COC3C2=CC=C3OCOC3=C2)=C1 PEYUIKBAABKQKQ-UHFFFAOYSA-N 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000011194 food seasoning agent Nutrition 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 235000015203 fruit juice Nutrition 0.000 description 1
- 235000019674 grape juice Nutrition 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000008309 hydrophilic cream Substances 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N nicotinic acid Natural products OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 235000015205 orange juice Nutrition 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 235000010604 prepared salads Nutrition 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 235000015067 sauces Nutrition 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 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 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000020183 skimmed milk Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000014214 soft drink Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000014347 soups Nutrition 0.000 description 1
- 235000013555 soy sauce Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 230000001502 supplementing effect Effects 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 229950009883 tocopheryl nicotinate Drugs 0.000 description 1
- 235000015193 tomato juice Nutrition 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 235000015192 vegetable juice Nutrition 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 235000013618 yogurt Nutrition 0.000 description 1
- OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 0.000 description 1
Landscapes
- Beans For Foods Or Fodder (AREA)
- Seasonings (AREA)
- Non-Alcoholic Beverages (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Seeds, Soups, And Other Foods (AREA)
- Medicines Containing Plant Substances (AREA)
- Dairy Products (AREA)
Description
【0001】[0001]
【産業上の利用分野】本発明は、血中コレステロールお
よび/または血中中性脂質を低減化せしめる水溶性リグ
ナン配糖体を含有してなる飲食物に関する。The present invention relates to a food or drink comprising a water-soluble lignan glycoside which reduces blood cholesterol and / or blood neutral lipid.
【0002】[0002]
【従来の技術】近年、欧米諸国をはじめわが国において
も血中のコレステロールや中性脂質(トリグリセリド)
の値が高い高脂血症疾患が増加している。高脂血症はや
がて動脈硬化等の症状をひきおこす危険因子と考えられ
ている。血中のコレステロールや中性脂質の量は生体内
で合成される内因性のものと食事成分に由来する外因性
のものとによって調節されるが、その過多を防止するた
めにニコチン酸トコフェロール等のニコチン酸誘導体、
ソイステロール、デキストラン硫酸等の高脂血症剤が開
発され、また食事由来のコレステロールや飽和脂肪酸を
主体とする動物性脂肪の摂取量を抑制することが推奨さ
れている。2. Description of the Related Art In recent years, blood cholesterol and neutral lipids (triglycerides) have been used in Western countries as well as in Japan.
High values of hyperlipidemia are increasing. Hyperlipidemia is considered to be a risk factor that eventually causes symptoms such as arteriosclerosis. The amount of cholesterol and neutral lipids in the blood is regulated by endogenous ones synthesized in the body and exogenous ones derived from dietary components, but in order to prevent the excess, such as tocopherol nicotinate Nicotinic acid derivatives,
Hyperlipidemic agents such as soysterol and dextran sulfate have been developed, and it has been recommended to reduce the intake of animal fats mainly composed of dietary cholesterol and saturated fatty acids.
【0003】日常の食事原材料のうち、とりわけ動物性
原材料中のコレステロールや脂肪を低減する方法とし
て、調理方法を工夫して脂肪およびこれと共存するコレ
ステロールを除くことがあるが、これら脂肪分を除くこ
とにより素材の風味や食感の低下をまねくことになる。
また例えば卵黄を油脂とともに乳化処理してコレステロ
ール含量を減らすことも提案されている(特開平5−3
44868号公報)が、製造コスト高になることは否め
ない。As a method of reducing cholesterol and fat in animal raw materials among daily dietary ingredients, a cooking method is sometimes devised to remove fat and cholesterol coexisting therewith. This leads to a decrease in the flavor and texture of the material.
It has also been proposed to reduce the cholesterol content by, for example, emulsifying egg yolk with fats and oils (Japanese Patent Laid-Open No. 5-3).
No. 44868), it is undeniable that the production cost increases.
【0004】一方、通常の食事に供される原材料の中に
は血中コレステロールや血中中性脂質を低下させる成分
を含むものがある。例えば前記ソイステロールは大豆中
に含まれる不ケン化物のステロールであり、また特開平
3−53866号公報にはゴマ油由来のリグナン類化合
物が開示されており、これを配合したバターやマヨネー
ズ等の飲食物が提案されている。これらの成分は通常の
医薬品として投与し、あるいは食事形態として摂取する
ことにより血中コレステロールや血中中性脂質を低減さ
せるものである。しかしながらこれらはいずれも油溶性
物質であり、生体に適合した形態で摂取させるには、リ
ポソーム製剤化するか、あるいは前記公報(特開平3−
53866号公報)に記載のようにリグナン類化合物を
シクロデキストリンに包接させ水系飲食物に配合するこ
とが必要であった。[0004] On the other hand, some of the raw materials used for ordinary meals contain components that lower blood cholesterol and blood neutral lipids. For example, the soysterol is an unsaponifiable sterol contained in soybean, and JP-A-3-53866 discloses a lignans compound derived from sesame oil, which is mixed with butter and mayonnaise such as butter and mayonnaise. Things have been suggested. These components reduce blood cholesterol and blood neutral lipids when administered as ordinary pharmaceuticals or taken as a dietary form. However, these are all oil-soluble substances, and in order to be taken in a form compatible with a living body, they must be formulated into a liposome or disclosed in the above-mentioned publication (Japanese Unexamined Patent Publication No.
As described in JP-A-53866), it was necessary to include a lignan compound in cyclodextrin and blend it into an aqueous food or drink.
【0005】ところで、ゴマ種子中には抗酸化活性を有
するセサミノール:テトラヒドロ−1−〔6−ヒドロキ
シ−3,4−(メチレンジオキシ)フェニル〕−4−
〔3,4−(メチレンジオキシ)フェニル〕−1H,3
H−フロ〔3,4−C〕フラン、P−1:テトラヒドロ
−1−(3−メトキシ−4−ヒドロキシフェニル)−4
−〔3,4−(メチレンジオキシ)フェニル〕−1H,
3H−フロ〔3,4−C〕フラン、セサモリノール:テ
トラヒドロ−1−〔3−メトキシ−4−ヒドロキシフェ
ノキシ〕−4−〔3,4−(メチレンジオキシ)フェニ
ル〕−1H,3H−フロ〔3,4−C〕フラン、ピノレ
ジノール:テトラヒドロ−1,4−ジ(3メトキシ−4
−ヒドロキシフェニル)−1H,3H−フロ〔3,4−
C〕フラン等のフェノール性リグナン類が含まれている
ことは周知である。これらのリグナン類の多くは糖化合
物(リグナン配糖体)としてゴマ種子またはその脱脂粕
中に存在することも知られている(Biosci.Bi
otech.Biochem.、56巻、2087〜2
088頁、1992年)。In sesame seeds, sesaminol having antioxidant activity: tetrahydro-1- [6-hydroxy-3,4- (methylenedioxy) phenyl] -4-
[3,4- (methylenedioxy) phenyl] -1H, 3
H-Flo [3,4-C] furan, P-1: tetrahydro-1- (3-methoxy-4-hydroxyphenyl) -4
-[3,4- (methylenedioxy) phenyl] -1H,
3H-Flo [3,4-C] furan, sesamolinol: tetrahydro-1- [3-methoxy-4-hydroxyphenoxy] -4- [3,4- (methylenedioxy) phenyl] -1H, 3H-furo 3,4-C] furan, pinoresinol: tetrahydro-1,4-di (3methoxy-4
-Hydroxyphenyl) -1H, 3H-furo [3,4-
C] It is well known that phenolic lignans such as furan are contained. It is also known that many of these lignans are present as sugar compounds (lignan glycosides) in sesame seeds or their defatted meals (Biosci. Bi).
otech. Biochem. , 56 volumes, 2087-2
088, 1992).
【0006】[0006]
【発明が解決しようとする課題】かかる現状に鑑み、本
発明では、食事の原材料として常用される天然物由来の
安全な物質であり、血中コレステロールおよび/または
血中中性脂質を低減させ得る物質であって、かつ水系な
いし乳化系状態で好適に利用できる物質を含有する飲食
物を提供することを目的とする。In view of such circumstances, the present invention is a natural substance-derived safe substance commonly used as a raw material for meals, and can reduce blood cholesterol and / or blood neutral lipid. It is an object of the present invention to provide a food or drink that contains a substance that can be suitably used in an aqueous or emulsified state.
【0007】[0007]
【課題を解決するための手段】本発明者らは、上記目的
を達成するために鋭意検討の結果、ゴマ種子の加湿物な
いし発芽体中に含まれるリグナン配糖体が安全な物質で
あり、血中コレステロールおよび/または血中中性脂質
を低減させる機能を有し、かつとりわけ水系ないし乳化
系の飲食物に都合よく配合できることを見い出し、本発
明を完成するに至ったものである。すなわち本発明の要
旨は、ゴマ種子の加湿物もしくは発芽体から得られる水
溶性リグナン配糖体またはこれを含む含有物を配合して
なる飲食物であり、ここに水溶性リグナン配糖体がより
好ましくはリグナンジグルコシドおよび/またはリグナ
ントリグルコシドを主成分とするものであり、さらに好
ましくはセサミノールジグルコシド、セサミノールトリ
グルコシドおよび下記の化学構造式(I)で示されるリ
グナン配糖体から選ばれる少なくとも1種以上を含むも
のである。Means for Solving the Problems The present inventors have made intensive studies in order to achieve the above object, and as a result, lignan glycosides contained in humidified or germinated bodies of sesame seeds are safe substances, The present inventors have found that they have a function of reducing blood cholesterol and / or neutral lipid in blood, and that they can be conveniently blended especially in aqueous or emulsified foods and drinks, and have completed the present invention. That is, the gist of the present invention is a food or drink comprising a water-soluble lignan glycoside obtained from a humidified substance or a germinated body of sesame seed or a substance containing the same, wherein the water-soluble lignan glycoside is more preferable. It is preferably one containing lignan diglucoside and / or lignan triglucoside as a main component, and more preferably selected from sesaminol diglucoside, sesaminol triglucoside and lignan glycoside represented by the following chemical structural formula (I). At least one or more of these.
【0008】[0008]
【化5】 (式(I)中、Rはグルコース、ガラクトースおよびフ
ルクトースからなる群より選ばれる1種のグルコシル残
基を表し、mは1〜3の整数値のいずれかを表し、nは
0または1の整数値を表す。)Embedded image (In the formula (I), R represents one kind of glucosyl residue selected from the group consisting of glucose, galactose and fructose, m represents any one of integers from 1 to 3, and n represents an integer of 0 or 1) Represents a numerical value.)
【0009】本発明をなすに先立ち、本発明者らは、ゴ
マ種子を原料として水溶性リグナン配糖体を多量に採取
する方法を開発し、特許出願した(特願平5−3160
79号、特願平6−336644号)。本発明で用いる
水溶性リグナン配糖体およびこれを含む含有物はこれら
に記載した方法により得ることができる。すなわち、原
料とするゴマ種子はその種類および産地のいかんを問わ
ず使用でき、これを未焙煎あるいは非加熱の状態で、水
中または水分を含有できる適当な培地、例えば寒天、石
英砂、海砂、脱脂綿、砂、土等の好ましくは滅菌処理し
た培地に均一に撒き、15〜50℃、好ましくは30〜
40℃にて、適時に水分を補いながら、5〜100時
間、好ましくは24〜72時間培養を行う。該培養は照
光下あるいは暗条件下のいずれでも構わない。かくして
水で膨潤した加湿物あるいは発芽したゴマ発芽物(ゴマ
種子の加湿物または発芽体)を得る。Prior to the present invention, the present inventors have developed a method for collecting a large amount of water-soluble lignan glycosides from sesame seeds and applied for a patent (Japanese Patent Application No. 5-3160).
No. 79, Japanese Patent Application No. 6-336644). The water-soluble lignan glycoside used in the present invention and a substance containing the same can be obtained by the methods described therein. That is, the sesame seeds used as a raw material can be used irrespective of the type and production area thereof, and can be used in an unroasted or unheated state in a suitable medium that can contain water or moisture, such as agar, quartz sand, and sea sand. , Absorbent cotton, sand, soil and the like, preferably evenly spread on a sterilized medium, 15 to 50 ° C, preferably 30 to 50 ° C.
Cultivation is performed at 40 ° C. for 5 to 100 hours, preferably for 24 to 72 hours, while supplementing water appropriately. The culture may be carried out under light or dark conditions. Thus, a humidified substance swelled with water or a germinated sesame germ (a humidified or germinated body of sesame seeds) is obtained.
【0010】本発明では、このようにして得たゴマ種子
の加湿物または発芽体を培地から分離し、これに必要に
応じて水洗浄等の適当な清浄処理を施した後、乳鉢、す
り潰し器、ミキサー、ブレンダー、ホモジナイザー等の
粉砕あるいは磨砕手段を用いて破砕して練り状の破砕物
となし、または前記加湿物またはゴマ発芽体を凍結乾燥
して乾燥物となし、さらにはこの乾燥物をミキサーやブ
レンダー等の粉砕機によって処理して粉砕物となし、こ
れらのいずれか1種以上を本発明の水溶性リグナン配糖
体を含む含有物いわば食品素材として飲食物に配合せし
めることができる。In the present invention, the humidified matter or germinated body of the sesame seed thus obtained is separated from the culture medium and, if necessary, subjected to an appropriate cleaning treatment such as washing with water, and then subjected to a mortar and a mortar. , Using a crushing or grinding means such as a mixer, a blender, a homogenizer or the like to form a kneaded crushed product, or freeze-drying the humidified material or the sesame germinated material to form a dried product, and further, a dried product thereof. Is treated with a pulverizer such as a mixer or a blender to form a pulverized product, and any one or more of these can be incorporated into foods and drinks as a so-called food material containing the water-soluble lignan glycoside of the present invention. .
【0011】さらに本発明では、より高濃度の水溶性リ
グナン配糖体含有物を飲食物に配合せしめることができ
る。このためには、前記のようにして得られるゴマ種子
の加湿物または発芽体から以下に述べるように抽出およ
び濃縮処理によって、より高純度の水溶性リグナン配糖
体を含む抽出物を調製し、これを用いることもできる。Further, in the present invention, a higher concentration of a water-soluble lignan glycoside-containing substance can be added to food or drink. To this end, an extract containing a higher purity water-soluble lignan glycoside is prepared from the humidified or germinated sesame seed obtained as described above by extraction and concentration treatment as described below, This can also be used.
【0012】すなわち、まず前記のようにしてゴマ種子
の加湿物または発芽体の破砕物、乾燥物あるいは粉砕物
を得る。ここで粉砕物等はn−ヘキサン等の有機溶媒で
油分を抽出して除去した脱脂粕としてもよい。次に水溶
性リグナン配糖体を抽出できる含水アルコール、具体的
にはメタノール、エタノール、n−プロパノール、イソ
プロパノール、n−ブタノール等の炭素数1〜4の直鎖
状もしくは側鎖状低級アルコールと水とを混合し、アル
コール濃度を30〜100%(容量/容量)、好ましく
は50〜95%(容量/容量)に調節したものを、原料
種子に対して1〜10倍(容量/重量)添加し、必要に
応じて磨砕および抽出操作を繰り返し行ない、濾過やデ
カンテーション等の常法により固形物を除去して水溶性
リグナン配糖体を含む含水アルコール抽出液を得る。ア
ルコールおよび水を除いた含水アルコール抽出物は、水
溶性リグナン配糖体のほか種々の糖鎖化合物を含む混合
物である。含水アルコール抽出物中の水溶性リグナン配
糖体の含有量は約2〜10重量%である。That is, first, a humidified sesame seed or a crushed, dried, or crushed germinated body is obtained as described above. Here, the pulverized material or the like may be defatted lees obtained by extracting and removing an oil component with an organic solvent such as n-hexane. Next, a water-containing alcohol from which a water-soluble lignan glycoside can be extracted, specifically, a linear or side-chain lower alcohol having 1 to 4 carbon atoms such as methanol, ethanol, n-propanol, isopropanol, and n-butanol, and water And the alcohol concentration adjusted to 30 to 100% (volume / volume), preferably 50 to 95% (volume / volume), and added 1 to 10 times (volume / weight) to the seed material. Then, if necessary, grinding and extraction operations are repeated, and solids are removed by a conventional method such as filtration or decantation to obtain a hydroalcoholic extract containing a water-soluble lignan glycoside. The hydroalcoholic extract excluding alcohol and water is a mixture containing various sugar chain compounds in addition to the water-soluble lignan glycoside. The content of the water-soluble lignan glycoside in the aqueous alcohol extract is about 2 to 10% by weight.
【0013】なお前記抽出物中の水溶性リグナン配糖体
以外の不純物を除くために以下の処理を施すこともでき
る。すなわち油溶性不純物を除くために、抽出物に対し
て2〜10倍(容量/重量)の非水溶性の有機溶媒、例
えば酢酸エチルやn−ヘキサンと水とを加えて抽出し、
遠心分離等により二相に分離する。有機溶媒相を除き、
水相を濃縮乾固させる。このとき目的の水溶性リグナン
配糖体には水相側に濃縮される。また水溶性不純物を除
くために、抽出物に対して少量、好ましくは1〜5倍
(容量/重量)の前記と同じアルコールの含水物(アル
コール濃度:30〜100%(容量/容量))に分散さ
せ、これを緩やかに攪拌している比較的多量、好ましく
は10〜200倍(容量/重量)の前記と同じアルコー
ルに滴下する。静置後、遠心分離または分別濾過等によ
り沈殿物を除き、濃縮乾固する。なお必要であればこれ
らの操作を繰り返す。[0013] In order to remove impurities other than the water-soluble lignan glycoside in the extract, the following treatment can be performed. That is, in order to remove oil-soluble impurities, the extract is extracted by adding 2 to 10 times (volume / weight) of a water-insoluble organic solvent, for example, ethyl acetate or n-hexane and water,
Separate into two phases by centrifugation or the like. Excluding the organic solvent phase,
The aqueous phase is concentrated to dryness. At this time, the desired water-soluble lignan glycoside is concentrated on the aqueous phase side. In order to remove water-soluble impurities, a small amount, preferably 1 to 5 times (volume / weight) of the same alcohol hydrate (alcohol concentration: 30 to 100% (volume / volume)) with respect to the extract is used to remove water-soluble impurities. It is dispersed and dropped into a relatively large amount, preferably 10 to 200 times (volume / weight) of the same alcohol, which is gently stirred. After standing, precipitates are removed by centrifugation or fractional filtration, and the mixture is concentrated to dryness. These operations are repeated if necessary.
【0014】かくして得られる含水アルコール抽出物の
精製物に含まれるリグナン配糖体は、公知のリグナン類
をアグリコンとする配糖体と新規なリグナンをアグリコ
ンとする配糖体との混合物である。公知のリグナン類を
アグリコンとする配糖体は、セサミノールを主成分とし
てほかにセサモリノール、P−1、ピノレジノール等の
リグナン類(リグナン類中、セサミノール:80〜90
重量%、セサモリノール、P−1、ピノレジノール:2
0重量%未満)とグルコース、ガラクトース等の糖類
(糖類中、グルコース:50〜100重量%)、特にグ
ルコースが2〜3分子結合したものである。新規なリグ
ナンをアグリコンとする配糖体は、下記の化学構造式
(I)で示されるものであり、より好ましくは下記の化
学構造式(II−a)、(II−b)または(II−
c)で示されるものである(II−a、II−bおよび
II−c三成分中の存在比、II−a:25〜35重量
%、II−b:35〜45重量%、II−c:30〜3
5重量%)。The lignan glycoside contained in the purified product of the hydroalcoholic extract thus obtained is a mixture of a known glycoside using lignans as aglycone and a novel glycoside using lignan as aglycone. Known glycosides containing lignans as aglycone include sesaminol as a main component and lignans such as sesamolinol, P-1, and pinoresinol (in lignans, sesaminol: 80 to 90).
% By weight, sesamolinol, P-1, pinoresinol: 2
0 to less than 0% by weight) and saccharides such as glucose and galactose (glucose in the saccharide: 50 to 100% by weight), particularly two or three molecules of glucose. The glycoside having a novel lignan as an aglycone is represented by the following chemical structural formula (I), more preferably the following chemical structural formula (II-a), (II-b) or (II-b)
(II-a: 25 to 35% by weight, II-b: 35 to 45% by weight, II-c) : 30 to 3
5% by weight).
【0015】[0015]
【化6】 (式(I)中、Rはグルコース、ガラクトースおよびフ
ルクトースからなる群より選ばれる1種のグルコシル残
基を表し、mは1〜3の整数値のいずれかを表し、nは
0または1の整数値を表す。)Embedded image (In the formula (I), R represents one kind of glucosyl residue selected from the group consisting of glucose, galactose and fructose, m represents any one of integers from 1 to 3, and n represents an integer of 0 or 1) Represents a numerical value.)
【0016】[0016]
【化7】 (式(II−a)中、Glcはグルコース残基を表
す。)Embedded image (In the formula (II-a), Glc represents a glucose residue.)
【0017】[0017]
【化8】 (式(II−b)中、Glcはグルコース残基を表
す。)Embedded image (In the formula (II-b), Glc represents a glucose residue.)
【0018】[0018]
【化9】 (式(II−c)中、Glcはグルコース残基を表
す。)Embedded image (In the formula (II-c), Glc represents a glucose residue.)
【0019】公知リグナン配糖体類と新規リグナン配糖
体類の比率は、1:1.5〜3(重量比)である。これ
らはブタノール、エタノール、メタノール、水等に可溶
な水溶性の物質である。なお必要に応じてシリカゲル、
ODS等の吸着剤を用いて、セサミノールジグルコシド
やセサミノールトリグルコシド、前記化学構造式(II
−a)、(II−b)あるいは(II−c)等の個々の
成分にさらに分画、精製することもできる。リグナン配
糖体の各成分の化学構造は、前記方法で高純度に精製し
た成分を、例えば塩酸加水分解してリグナン部と糖部と
に分け、これらをそれぞれトリメチルシリル化してガス
クロマトグラフィーに供し、あるいは核磁気共鳴スペク
トロスコピー、マススペクトロスコピー等により分析し
確認できる。The ratio of known lignan glycosides to novel lignan glycosides is 1: 1.5 to 3 (weight ratio). These are water-soluble substances soluble in butanol, ethanol, methanol, water and the like. If necessary, silica gel,
Using an adsorbent such as ODS, sesaminol diglucoside or sesaminol triglucoside, the chemical structural formula (II)
It can be further fractionated and purified into individual components such as -a), (II-b) or (II-c). Chemical structure of each component of the lignan glycoside, the components purified to high purity by the above method, for example, hydrolyzed with hydrochloric acid to divide the lignan part and the sugar part, these are trimethylsilylated and subjected to gas chromatography, Alternatively, it can be analyzed and confirmed by nuclear magnetic resonance spectroscopy, mass spectroscopy, or the like.
【0020】かかる水溶性リグナン配糖体自体の多く
は、抗酸化性をもたないが、抗酸化性成分の前駆体とし
て存在し、糖結合の加水分解作用を受けるような、例え
ば生体内において特異的にその活性が期待される物質で
ある。また抗酸化性を有するゴマ種子由来の公知のフェ
ノール性リグナン類すなわちセサミノール、P−1、セ
サモリノール、ピノレジノール等に比較して、本発明に
係る水溶性リグナン配糖体は熱に対する安定性も高い
(50℃、24時間加温後の分解率は5%以下)。Many of such water-soluble lignan glycosides themselves do not have antioxidant properties, but exist as precursors of antioxidant components and undergo hydrolysis of sugar bonds, for example, in vivo. It is a substance whose activity is expected specifically. In addition, as compared with known phenolic lignans derived from sesame seeds having antioxidant properties, that is, sesaminol, P-1, sesamolinol, pinoresinol, etc., the water-soluble lignan glycoside according to the present invention also has high heat stability. (The decomposition rate after heating at 50 ° C. for 24 hours is 5% or less).
【0021】これらリグナン配糖体は、ゴマ種子100
g中にわずか約240mgしか含まれないが、ゴマ種子を
前述のように適当な条件下で加湿すると、その膨潤ない
しは発芽とともにリグナン配糖体のゴマ種子中の含有量
が増加し、特にセサミノール配糖体を多量に生産し蓄積
する。加湿しないゴマ種子中のセサミノール配糖体含量
に比べ、例えば加湿48時間後のものからは、少なくと
も3倍(重量)以上のセサミノール配糖体を得ることが
できる。また、化学構造式(II−a)、(II−b)
および(II−c)で示される新規なリグナン配糖体
は、ゴマ種子の加湿および発芽前にはほとんど存在しな
い成分であり、膨潤ないしは発芽とともに新たに生成、
増加し加湿物あるいは発芽体中に蓄積する。これらの結
果、例えばゴマ種子の発芽体中のリグナン配糖体の総量
は、発芽前のゴマ種子に比べ5〜6倍(重量)以上とな
り、ゴマ発芽体の乾燥物当たり約3重量%に達する。These lignan glycosides are obtained from sesame seed 100
Although only about 240 mg is contained in the sesame seed, if the sesame seed is humidified under appropriate conditions as described above, the content of the lignan glycoside in the sesame seed increases with swelling or germination. Produces and accumulates glycosides in large quantities. Compared to the sesameol glycoside content in the humidified sesame seeds, for example, after 48 hours of humidification, the sesameol glycoside can be obtained at least three times (by weight) or more. Further, the chemical structural formulas (II-a) and (II-b)
The novel lignan glycoside represented by and (II-c) is a component that hardly exists before humidification and germination of sesame seeds, and is newly formed together with swelling or germination,
Increases and accumulates in humidified or germinated bodies. As a result, for example, the total amount of lignan glycosides in the germinated body of sesame seeds is 5 to 6 times (weight) or more as compared to the sesame seeds before germination, and reaches about 3% by weight per dry matter of the sesame germinated body. .
【0022】なお本発明に用いる水溶性リグナン配糖体
類は、以上に述べたようにゴマ種子の加湿物または発芽
体の破砕物、乾燥物あるいはその粉砕物としてそのまま
用いるか、これらから水溶性リグナン配糖体を前記のよ
うに抽出する方法が簡便であるが、水溶性リグナン配糖
体が前記の構造および組成をもつものであれば、これに
限定されるものではない。As described above, the water-soluble lignan glycoside used in the present invention may be used as it is as a humidified sesame seed or a crushed or dried germinated body, a dried product or a crushed product thereof, or a water-soluble lignan glycoside may be used. The method for extracting lignan glycosides as described above is simple, but the method is not limited to this as long as the water-soluble lignan glycosides have the above-mentioned structure and composition.
【0023】本発明においては、前記の方法によって得
られる水溶性リグナン配糖体または水溶性リグナン配糖
体を含有する、ゴマ種子の加湿物もしくは発芽体の破砕
物、乾燥物またはこれの粉砕物、あるいはこれらの抽出
物(含水アルコール抽出物またはこの精製物)を必須成
分として配合してなる飲食物が提供される。ここに飲食
物の種類は特に限定されないが、配合せしめるリグナン
配糖体またはこれを含む前記含有物の性状が水溶性ない
し水分散性であるため、これらを均一に溶解ないしは分
散させて含有せしめるには水系あるいは乳化系飲食物が
好適である。具体的には水(飲料水)、果汁、野菜汁、
ジュース、炭酸飲料、清涼飲料、各種栄養成分を配合し
たドリンク類、スープ、醤油、ソース、その他液体調味
料、アイスクリーム、ヨーグルト、豆乳、牛乳、バタ
ー、マーガリン、クリーム、サラダドレッシング、ノン
オイルサラダドレッシング、マヨネーズ、マヨネーズ様
食品、等を例示できる。In the present invention, a humidified or germinated crushed or dried sesame seed, or a crushed product thereof, containing a water-soluble lignan glycoside or a water-soluble lignan glycoside obtained by the above method. Alternatively, there is provided a food or beverage comprising an extract (hydrous alcohol extract or purified product thereof) as an essential component. Here, the type of food or drink is not particularly limited, but since the properties of the lignan glycoside to be compounded or the above-mentioned ingredients containing the same are water-soluble or water-dispersible, they are uniformly dissolved or dispersed to be contained. Is preferably an aqueous or emulsified food or drink. Specifically, water (drinking water), fruit juice, vegetable juice,
Juices, carbonated drinks, soft drinks, drinks containing various nutrients, soups, soy sauce, sauces, other liquid seasonings, ice cream, yogurt, soy milk, milk, butter, margarine, cream, salad dressing, non-oil salad dressing, Mayonnaise, mayonnaise-like food, and the like can be exemplified.
【0024】これら飲食物中の水溶液リグナン配糖体の
含有量は概ね0.002重量%以上、好ましくは0.0
02〜30重量%である。水溶性リグナン配糖体を含
む、ゴマ種子の加湿物または発芽体の破砕物の場合は1
重量%以上、好ましくは1〜70重量%であり、ゴマ種
子の加湿物または発芽体の乾燥物やその粉砕物の場合は
0.02重量%以上、好ましくは0.02〜50重量%
であり、またかかる破砕物、乾燥物あるいは粉砕物から
の抽出物の場合には、前記含水アルコール抽出物のと
き、0.01重量%以上、好ましくは0.01〜40重
量%であり、該含水アルコール抽出物から油溶性不純物
および/または水溶性不純物を除去した水溶性リグナン
配糖体混合物や例えばセサミノールジグルコシド、セサ
ミノールトリグルコシド、前記化学構造式(II−
a)、(II−b)、(II−c)のような個々の精製
リグナン配糖体のとき0.002重量%以上、好ましく
は0.002〜30重量%である。前記下限値未満では
血中コレステロールおよび/または血中中性脂質の低減
効果が小さい。また前記上限値を超えて含有せしめても
よいが、この場合は多量の含有量に見合う血中コレステ
ロールおよび/または血中中性脂質のさらなる低減効果
は期待できない。水溶性リグナン配糖体またはこれを含
む前記抽出物等を飲食物に配合せしめる方法は特に限定
されないが、水相に予め溶解ないしは分散させておき、
ついで常法により飲食物を調製するのがよい。The content of the aqueous lignan glycoside in these foods and drinks is generally at least 0.002% by weight, preferably 0.02% by weight.
02 to 30% by weight. 1 in the case of humidified sesame seeds or crushed germinated material containing water-soluble lignan glycosides
% By weight, preferably 1 to 70% by weight, and 0.02% by weight or more, preferably 0.02 to 50% by weight in the case of humidified sesame seeds or dried germinated material or crushed material thereof.
In the case of an extract from such a crushed product, a dried product or a crushed product, the content is 0.01% by weight or more, preferably 0.01 to 40% by weight, in the case of the aqueous alcohol extract. A water-soluble lignan glycoside mixture obtained by removing oil-soluble impurities and / or water-soluble impurities from a water-containing alcohol extract, such as sesaminol diglucoside, sesaminol triglucoside, and the above-mentioned chemical structural formula (II-
In the case of individual purified lignan glycosides such as a), (II-b) and (II-c), the content is 0.002% by weight or more, preferably 0.002 to 30% by weight. Below the lower limit, the effect of reducing blood cholesterol and / or blood neutral lipid is small. Further, it may be contained in excess of the above upper limit, but in this case, a further effect of reducing blood cholesterol and / or blood neutral lipid corresponding to the large content cannot be expected. The method of incorporating the water-soluble lignan glycoside or the extract containing the same into a food or drink is not particularly limited, but is previously dissolved or dispersed in an aqueous phase,
Then, it is good to prepare food and drink by a conventional method.
【0025】[0025]
参考例1 予め滅菌した石英砂を300cm2 のステンレス製バット
に厚さ5mmで均一に敷き、これに中国産ゴマ種子100
gを撒き、蒸留水を十分に噴霧しながら、40℃の恒温
槽中で48時間培養し、発芽させた。発芽率は80%で
あった。発芽状態が同程度の一定量の発芽体をサンプリ
ングし、ゴマ発芽物とした。ゴマ発芽物を水洗後、粉砕
器で磨砕しゴマ発芽物の破砕物を得た。またゴマ発芽物
を凍結乾燥機で乾燥し、ゴマ発芽物の乾燥物を得た。さ
らにこのゴマ発芽物の乾燥物を粉砕機で粉砕し、ゴマ発
芽物の乾燥粉砕物を得た。ゴマ発芽物の乾燥粉砕物10
gを100mlの含水エタノール(エタノール濃度:80
%(容量/容量))とともにブレンダーで磨砕した。残
渣を濾別し、濾液を濃縮乾固した後、得られた固形物(
含水エタノール抽出物) をn−ヘキサンおよび酢酸エチ
ルで2度ずつ洗浄して含水エタノール抽出物の精製混合
物を得た。含水エタノール抽出物の精製混合物を100
mlの含水エタノールに再溶解し、HPLCに供して組成
を分析した。REFERENCE EXAMPLE 1 Quartz sand previously sterilized was spread evenly over a 300 cm 2 stainless steel vat with a thickness of 5 mm, and 100 g of sesame seeds produced in China.
g, and germinated by culturing in a constant temperature bath at 40 ° C. for 48 hours while sufficiently spraying distilled water. The germination rate was 80%. A fixed amount of germinated bodies having the same germination state were sampled to obtain sesame germinated products. After washing the sesame germ with water, it was ground with a crusher to obtain a crushed sesame germ. The sesame germ was dried with a freeze dryer to obtain a dried sesame germ. Further, the dried sesame germ product was pulverized with a crusher to obtain a dried and crushed sesame germ product. Dried and ground sesame germ 10
g of 100 ml of aqueous ethanol (ethanol concentration: 80).
% (Vol / vol)) in a blender. The residue was filtered off, and the filtrate was concentrated to dryness.
The aqueous ethanol extract) was washed twice with n-hexane and ethyl acetate to obtain a purified mixture of the aqueous ethanol extract. 100 parts of the purified mixture of aqueous ethanol extract
It was redissolved in ml of hydrous ethanol and subjected to HPLC for composition analysis.
【0026】HPLC装置は、ポンプ(CCPM、東ソ
ー社製)にカラム(Soken Pak ODS−W
5μ、10mmφ×250mm)、紫外吸収検出器(UV−
8000、東ソー社製)を接続し、溶出は水:メタノー
ルが90:10から60分後に同10:90となる直線
グラジェントを用い、流速を1ml/min 、検出波長は2
88nmとした。The HPLC apparatus was equipped with a pump (CCPM, manufactured by Tosoh Corporation) and a column (Soken Pak ODS-W).
5μ, 10mmφ × 250mm), UV absorption detector (UV-
8000, manufactured by Tosoh Corporation), elution was performed using a linear gradient of 90:10 water: methanol to 10:90 after 60 minutes, a flow rate of 1 ml / min, and a detection wavelength of 2
It was 88 nm.
【0027】また含水エタノール抽出物を前記条件下で
分取HPLCに繰り返して供し、各成分が単一になるま
で精製した後、各成分を構成するリグナンおよび糖を次
の方法で分析した。すなわち各成分の精製物に1N塩酸
を加え、100℃で30分間加水分解せしめた後、酢酸
エチルで抽出し、酢酸エチル層および水層に分けた。酢
酸エチル層は40℃以下で濃縮乾固後、TMS−PZ
(東京化成工業社製)でトリメチルシリル化処理し、ガ
スクロマトグラフィー(GLC)に供してリグナンを定
量分析した(外標準:セサミン)。Further, the aqueous ethanol extract was repeatedly subjected to preparative HPLC under the above conditions, and purified until each component became single. After that, lignans and sugars constituting each component were analyzed by the following method. That is, 1N hydrochloric acid was added to the purified product of each component, hydrolyzed at 100 ° C. for 30 minutes, extracted with ethyl acetate, and separated into an ethyl acetate layer and an aqueous layer. The ethyl acetate layer is concentrated to dryness at 40 ° C or less, and then TMS-PZ
The product was subjected to trimethylsilylation treatment (manufactured by Tokyo Chemical Industry Co., Ltd.) and subjected to gas chromatography (GLC) to quantitatively analyze lignan (external standard: sesamin).
【0028】GLC条件は次のとおり。GLC装置:ヒ
ューレットパッカード社製5890、カラム:DB−1
7HT(15m×0.319mm、film thickness:0.
15μm、J&W SCIENTIFIC社製)、注入
法:スプリット法(スプリット比1/10)、カラム温
度:270℃、キャリヤーガス:ヘリウム。GLC conditions are as follows. GLC apparatus: 5890 manufactured by Hewlett-Packard Company, column: DB-1
7HT (15m × 0.319mm, film thickness: 0.
15 μm, manufactured by J & W SCIENTIFIC), injection method: split method (split ratio: 1/10), column temperature: 270 ° C., carrier gas: helium.
【0029】また水層をHPLC用前処理フィルター
(孔径:0.2μm、マイショリディスク W−13−
2、東ソー社製)で濾過し、濾液にアセトン5mlを加え
て減圧下で濃縮乾固後、TMS−PZ(前出と同じ)で
トリメチルシリル化処理し、これをGLCに供して糖を
定量分析した(外標準:グルコース、ガラクトース、フ
ルクトース)。Further, the aqueous layer was subjected to a pretreatment filter for HPLC (pore size: 0.2 μm, Meishoridisk W-13).
2, Tosoh Corporation), add 5 ml of acetone to the filtrate, concentrate under reduced pressure to dryness, then perform trimethylsilylation treatment with TMS-PZ (same as above), and subject it to GLC for quantitative analysis of sugar. (External standard: glucose, galactose, fructose).
【0030】GLC条件は、カラム:DB−1701
(15m×0.25mm、film thickness:1.0μm、
J&W SCIENTIFIC社製)、注入法:スプリ
ット法(スプリット比1/50)、カラム温度:180
℃とする以外は前記リグナン分析の場合と同様である。The GLC conditions were as follows: Column: DB-1701
(15m × 0.25mm, film thickness: 1.0μm,
J & W SCIENTIFIC), injection method: split method (split ratio 1/50), column temperature: 180
The procedure is the same as in the case of the lignan analysis except that the temperature is set to ° C.
【0031】この結果、前記含水エタノール抽出物中の
水溶性リグナン配糖体含有量は5.5重量%であり、ま
た前記HPLC分析サンプル(含水エタノール抽出物の
精製混合物)中のリグナン配糖体含有量は、播種したゴ
マ種子100gあたり1460mgであり、水溶性リグナ
ン配糖体の比率として、前記の化学構造式(II−a)
で示されるリグナン配糖体:20.9重量%、同じく
(II−b)で示されるリグナン配糖体:28.1重量
%、同じく(II−c)で示されるリグナン配糖体:2
4.2重量%、セサミノールトリグルコシド:7.8重
量%、セサミノールジグルコシド:14.4重量%、セ
サモリノール配糖体、P−1配糖体およびピノレジノー
ル配糖体の合計4.6重量%のリグナン配糖体を主成分
とする水溶性のものであった。As a result, the water-soluble lignan glycoside content in the aqueous ethanol extract was 5.5% by weight, and the lignan glycoside in the HPLC analysis sample (purified mixture of the aqueous ethanol extract) was obtained. The content is 1460 mg per 100 g of sown sesame seeds, and is defined as the ratio of the water-soluble lignan glycoside by the chemical structural formula (II-a) described above.
Lignan glycoside represented by: 20.9% by weight, lignan glycoside similarly represented by (II-b): 28.1% by weight, lignan glycoside similarly represented by (II-c): 2
4.2% by weight, sesaminol triglucoside: 7.8% by weight, sesaminol diglucoside: 14.4% by weight, a total of 4.6% by weight of sesamolinol glycoside, P-1 glycoside and pinoresinol glycoside % Lignan glycoside as a main component.
【0032】試験例1 4週令のSD系雄性ラット7匹を1試験区とし、A群は
試験物質(参考例1に記載の方法で得たゴマ発芽物の破
砕物、ゴマ発芽物の乾燥粉砕物)を各10重量%配合し
た試験群、B群は試験物質(参考例1に記載の方法で得
た含水アルコール抽出物、該抽出物の精製混合物、各リ
グナン配糖体精製物)を各0.3重量%配合した試験
群、および試験物質を添加しない対照群に分けて飼育試
験を行った。なお試験飼料は表1に示す成分に、後述す
る実施例1に記載のミネラル水100mlに各試験物質
(A群は100g、B群は3g)を溶解ないし分散させ
た水溶液あるいは水懸濁液10重量%を添加し、混練し
たものとした。水と前記各飼料とを自由摂取させて3週
間飼育した後、各群ラットの血中および肝臓中の総コレ
ステロール、中性脂質およびリン脂質各量を測定した。
この結果を表2および表3に示す。Test Example 1 Seven 4-week-old SD male rats were used as one test group, and group A was a test substance (crushed sesame germ products obtained by the method described in Reference Example 1, dried sesame germ products). Each of the test group and the group B containing 10% by weight of each of the pulverized products) contained a test substance (a hydroalcoholic extract obtained by the method described in Reference Example 1, a purified mixture of the extract, and a purified product of each lignan glycoside). The breeding test was performed by dividing into a test group containing 0.3% by weight of each and a control group to which no test substance was added. The test feed was prepared by dissolving or dispersing each test substance (100 g for group A, 3 g for group B) in 100 ml of mineral water described in Example 1 described below in the components shown in Table 1 or an aqueous suspension 10. % By weight and kneaded. After breeding for 3 weeks with water and each of the above-mentioned feeds freely taken, the total amount of cholesterol, neutral lipid and phospholipid in blood and liver of each group of rats was measured.
The results are shown in Tables 2 and 3.
【0033】[0033]
【表1】 [Table 1]
【0034】[0034]
【表2】 [Table 2]
【0035】[0035]
【表3】 [Table 3]
【0036】ゴマ発芽物の破砕物、乾燥粉砕物、含水ア
ルコール抽出物、該抽出物の精製混合物、各リグナン配
糖体精製物の各試験物質を添加した区では、血中の総コ
レステロール、中性脂質およびリン脂質の各濃度は前記
試験物質を添加しない区(対照群)と比べていずれも有
意に低い値を示した(表2)。またこれらの試験物質を
添加すると、肝臓中の総コレステロールおよび中性脂質
の各濃度が対照群に比べて有意に低下した(表3)。こ
れらの結果から、前記の化学構造式(II−)、(II
−b)、(II−c)で示されるリグナン配糖体または
セサミノール配糖体を主成分として含む水溶性リグナン
配糖体、あるいは該配糖体を含有するゴマ種子の発芽物
の破砕物、乾燥物、乾燥粉砕物、含水アルコール抽出
物、該抽出物の精製混合物、各リグナン配糖体精製物を
配合せしめてなる飼料は、これを摂取することにより血
中コレステロール値および血中中性脂質値を低下させる
ことが明らかになった。[0036] In the group to which each test substance of crushed sesame germ, dried and crushed, hydrated alcoholic extract, purified mixture of the extract, and each purified lignan glycoside was added, the total cholesterol in the blood was measured. The concentrations of the sex lipids and phospholipids were significantly lower than those of the group without the test substance (control group) (Table 2). When these test substances were added, the total cholesterol and neutral lipid levels in the liver were significantly reduced as compared to the control group (Table 3). From these results, the above-mentioned chemical structural formulas (II-), (II-
-B) a water-soluble lignan glycoside containing a lignan glycoside or a sesaminol glycoside represented by (II-c) as a main component, or a crushed product of a germinated product of sesame seed containing the glycoside , Dried products, dried and crushed products, aqueous alcoholic extracts, purified mixtures of the extracts, and feeds containing the purified lignan glycosides, can be used to ingest blood cholesterol levels and blood neutrality. It was found to lower lipid levels.
【0037】[0037]
実施例1 市販のミネラルウォーター100mlに、参考例1に記載
の方法で得た含水アルコール抽出物、該抽出物の精製混
合物、セサミノールジグルコシドおよびセサミノールト
リグルコシド各0.3重量%を加え、ゆるやかに攪拌し
て溶解させ、本発明の水溶性リグナン配糖体含有飲料水
を得た。Example 1 To 100 ml of commercially available mineral water, a hydroalcoholic extract obtained by the method described in Reference Example 1, a purified mixture of the extract, 0.3% by weight of each of sesaminol diglucoside and sesaminol triglucoside were added. The mixture was slowly stirred and dissolved to obtain a drinking water containing the water-soluble lignan glycoside of the present invention.
【0038】実施例2 下記の表に示した成分配合比でフレンチドレッシングを
調製した。Example 2 A French dressing was prepared at the compounding ratios shown in the following table.
【表4】 すなわち、キサンタンガムおよびゴマ発芽物の乾燥粉砕
物を水、酢および砂糖の半分量を溶解したものに加え、
激しく撹拌しつつ15分間かけて水和した。大豆サラダ
油を除く残りの成分を全て混ぜてこれに加えた。さらに
大豆サラダ油を少量ずつ加えた後、コロイドミルに通
し、安定性の高い本発明の水溶性リグナン配糖体含有ド
レッシングを得た。[Table 4] That is, dry and crushed xanthan gum and sesame germ are added to water, half of vinegar and sugar dissolved,
Hydrated for 15 minutes with vigorous stirring. All the remaining ingredients except soy salad oil were mixed and added to this. Further, after adding soybean salad oil little by little, the mixture was passed through a colloid mill to obtain a highly stable water-soluble lignan glycoside-containing dressing of the present invention.
【0039】実施例3 蒸煮丸大豆3kgを5倍重量の80℃の熱水中でホモミキ
サーを用いて磨砕した。得られた呉を、さらにホモナイ
ザーで処理した後、これをプレート間接殺菌(130
℃、20秒)し、オカラを遠心分離で除去して豆乳を得
た。この豆乳に参考例1に記載の方法で得た含水アルコ
ール抽出物を1重量%加え、溶解させ、本発明の水溶性
リグナン配糖体含有豆乳を得た。Example 3 3 kg of steamed round soybeans were ground in a 5-fold weight of hot water at 80 ° C. using a homomixer. The obtained go was further treated with a homogenizer, and then this was indirectly sterilized with a plate (130).
℃, 20 seconds), and okara was removed by centrifugation to obtain soymilk. To this soymilk, 1% by weight of the hydroalcoholic extract obtained by the method described in Reference Example 1 was added and dissolved to obtain a water-soluble lignan glycoside-containing soymilk of the present invention.
【0040】実施例4 オレンジ、ぶどう、リンゴおよびトマトの搾汁各100
mlに、参考例1に記載の方法で得た含水アルコール抽出
物各10gを加え、溶解させ、本発明の水溶性リグナン
配糖体含有ジュースを得た。Example 4 Orange, grape, apple and tomato juices, 100 each
To each ml, 10 g of the hydroalcoholic extract obtained by the method described in Reference Example 1 was added and dissolved to obtain a water-soluble lignan glycoside-containing juice of the present invention.
【0041】実施例5 バターオイル20重量部、大豆硬化油10重量部、レシ
チン0.2重量部およびグリセリン脂肪酸エステル(花
王(株)製、「エキセルO−95R」0.2重量部を油
相部とし、一方、脱脂粉乳3重量部、ソルビトール5重
量部、生クリーム10重量部、ポリグリセリン脂肪酸エ
ステル(坂本薬品(株)製、「SYグリスター MS−
310」)0.5重量部および水51.1重量部に参考
例1に記載の方法で得た含水アルコール抽出物の精製混
合物15重量部を加え、溶解させて水相部とした。つい
で、80℃に加温した水相部に同温度に加温した油相部
を加え、70〜75℃で予備乳化後、ホモジナイザーを
用いて圧力50kg/cm2 で処理して均質化した後、室温
まで冷却して本発明の水溶性リグナン配糖体含有水中油
型クリームを得た。Example 5 20 parts by weight of butter oil, 10 parts by weight of hardened soybean oil, 0.2 part by weight of lecithin and 0.2 part by weight of glycerin fatty acid ester ("EXCEL O-95R" manufactured by Kao Corporation) were used in the oil phase. On the other hand, 3 parts by weight of skim milk powder, 5 parts by weight of sorbitol, 10 parts by weight of fresh cream, polyglycerin fatty acid ester (manufactured by Sakamoto Yakuhin Co., Ltd., "SY Glister MS-
310 ") 15 parts by weight of a purified mixture of a hydroalcoholic extract obtained by the method described in Reference Example 1 was added to 0.5 parts by weight and 51.1 parts by weight of water, and dissolved to obtain an aqueous phase. Then, the oil phase portion heated to the same temperature was added to the water phase portion heated to 80 ° C., and after preliminarily emulsified at 70 to 75 ° C., the mixture was homogenized by treatment with a homogenizer at a pressure of 50 kg / cm 2. After cooling to room temperature, an oil-in-water cream containing the water-soluble lignan glycoside of the present invention was obtained.
【0042】実施例6 大豆硬化油/調合サラダ油=2/3(重量比)からなる
油脂83重量部に、グリセリン脂肪酸エステル(理研ビ
タミン(株)製、「エマルジーMU」)0.5重量部、
レシチン0.1重量部およびβ−カロチン微量を加え、
さらに参考例1に記載の方法で得たセサミノールジグル
コシドおよびセサミノールトリグルコシドの等重量混合
物5gを水100mlに溶解させた水溶液15重量部およ
び食塩1.4重量部を加えて乳化させた後、急冷しなが
ら練りあわせて、本発明の水溶性リグナン配糖体含有マ
ーガリンを得た。Example 6 0.5 parts by weight of glycerin fatty acid ester ("Emulgy MU", manufactured by Riken Vitamin Co., Ltd.) was added to 83 parts by weight of a fat and oil composed of hardened soybean oil / prepared salad oil = 2/3 (weight ratio).
0.1 parts by weight of lecithin and a trace amount of β-carotene were added,
Further, 15 parts by weight of an aqueous solution obtained by dissolving 5 g of an equal weight mixture of sesaminol diglucoside and sesaminol triglucoside obtained in the method described in Reference Example 1 in 100 ml of water and 1.4 parts by weight of sodium chloride were added to emulsify. And kneaded while quenching to obtain margarine containing the water-soluble lignan glycoside of the present invention.
【0043】[0043]
【発明の効果】本発明によれば、ゴマ種子とりわけその
加湿物ないし発芽体を原料として容易に得ることがで
き、安全性の点で懸念がなく、かつ摂取することにより
血中コレステロールおよび/または血中中性脂質を低減
させる作用をもつ水溶性リグナン配糖体を含有する飲食
物、とくに水系ないし乳化系各種飲食物を提供できる。According to the present invention, sesame seeds, especially humidified or germinated bodies thereof, can be easily obtained as a raw material, there is no concern about safety, and blood cholesterol and / or Foods and drinks containing a water-soluble lignan glycoside having an action of reducing neutral lipids in blood, particularly various water-based or emulsified foods and drinks can be provided.
フロントページの続き (51)Int.Cl.6 識別記号 FI A23L 1/36 A23L 1/36 2/52 A61K 31/70 ADN A61K 31/70 ADN 35/78 35/78 A23L 2/00 F (58)調査した分野(Int.Cl.6,DB名) A23L 1/30 C07H 17/04 CA(STN)Continued on the front page (51) Int.Cl. 6 Identification code FI A23L 1/36 A23L 1/36 2/52 A61K 31/70 ADN A61K 31/70 ADN 35/78 35/78 A23L 2/00 F (58) Field surveyed (Int.Cl. 6 , DB name) A23L 1/30 C07H 17/04 CA (STN)
Claims (6)
られる水溶性リグナン配糖体またはこれを含む含有物を
配合してなる飲食物。1. A food or drink comprising a water-soluble lignan glycoside obtained from humidified or germinated sesame seeds or a substance containing the same.
マ種子の加湿物もしくは発芽体またはこれらの乾燥物で
ある請求項1に記載の飲食物。2. The food or drink according to claim 1, wherein the substance containing the water-soluble lignan glycoside is a humidified or germinated body of sesame seeds or a dried product thereof.
マ種子の加湿物もしくは発芽体の含水低級アルコール抽
出物または該抽出物の濃縮物である請求項1に記載の飲
食物。3. The food or drink according to claim 1, wherein the content containing the water-soluble lignan glycoside is a humidified sesame seed or a hydrated lower alcohol extract of a germinated body, or a concentrate of the extract.
コシドおよび/またはリグナントリグルコシドを主成分
とするものである請求項1〜3のいずれか1項に記載の
飲食物。4. The food or drink according to claim 1, wherein the water-soluble lignan glycoside comprises lignan diglucoside and / or lignan triglucoside as a main component.
グナントリグルコシドがセサミノールジグルコシド、セ
サミノールトリグルコシド、下記の化学構造式(I) 【化1】 (式(I)中、Rはグルコース、ガラクトースおよびフ
ルクトースからなる群より選ばれる1種のグルコシル残
基を表し、mは1〜3の整数値のいずれかを表し、nは
0または1の整数値を表す。)で示されるリグナン配糖
体から選ばれる少なくとも1種以上である請求項4に記
載の飲食物。5. The lignan diglucoside and / or lignan triglucoside is sesaminol diglucoside, sesaminol triglucoside, having the following chemical structural formula (I): (In the formula (I), R represents one kind of glucosyl residue selected from the group consisting of glucose, galactose and fructose, m represents any one of integers from 1 to 3, and n represents an integer of 0 or 1) The food or drink according to claim 4, which is at least one member selected from lignan glycosides represented by the following numerical values:
されるリグナン配糖体が下記の化学構造式(II−
a)、(II−b)または(II−c) 【化2】 (式(II−a)中、Glcはグルコース残基を表
す。) 【化3】 (式(II−b)中、Glcはグルコース残基を表
す。) 【化4】 (式(II−c)中、Glcはグルコース残基を表
す。)で示されるリグナン配糖体である請求項5に記載
の飲食物。6. The lignan glycoside represented by the chemical structural formula (I) according to claim 5, wherein the lignan glycoside is represented by the following chemical structural formula (II-
a), (II-b) or (II-c) (In the formula (II-a), Glc represents a glucose residue.) (In the formula (II-b), Glc represents a glucose residue.) (In formula (II-c), Glc represents a glucose residue.) The food or drink according to claim 5, which is a lignan glycoside represented by the formula:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7148278A JP2815136B2 (en) | 1995-05-23 | 1995-05-23 | Food and drink containing lignan glycosides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7148278A JP2815136B2 (en) | 1995-05-23 | 1995-05-23 | Food and drink containing lignan glycosides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH08317775A JPH08317775A (en) | 1996-12-03 |
| JP2815136B2 true JP2815136B2 (en) | 1998-10-27 |
Family
ID=15449195
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7148278A Expired - Lifetime JP2815136B2 (en) | 1995-05-23 | 1995-05-23 | Food and drink containing lignan glycosides |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2815136B2 (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH10182331A (en) * | 1996-12-26 | 1998-07-07 | Nisshin Oil Mills Ltd:The | Cosmetic |
| JPH11246427A (en) * | 1998-03-04 | 1999-09-14 | Kadoya Sesami Mills Inc | Agent for activating metabolism of saccharide and lipid |
| JP4986388B2 (en) * | 2004-10-01 | 2012-07-25 | 太陽化学株式会社 | Emulsifier composition |
| ES2375115T3 (en) | 2005-03-31 | 2012-02-24 | Suntory Holdings Limited | EMULSION OF WATER OIL CONTAINING A LIGNANE COMPOSITE AND COMPOSITION THAT INCLUDE THE SAME. |
| JP2009082031A (en) * | 2007-09-28 | 2009-04-23 | Kaiyo Bokujo:Kk | Method for producing sprout extract |
| US20160136214A1 (en) * | 2014-11-10 | 2016-05-19 | University Of Central Florida Research Foundation, Inc. | Sesame seed oil aqueous extracts and methods of making and using thereof |
| JP7079931B2 (en) * | 2018-05-10 | 2022-06-03 | 淳三 亀井 | Encapsulation complex of sesaminol and cyclodextrin and its production method |
-
1995
- 1995-05-23 JP JP7148278A patent/JP2815136B2/en not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| Phytochemistry 35(3)p.773−776(1994) |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH08317775A (en) | 1996-12-03 |
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