JPH0363561B2 - - Google Patents
Info
- Publication number
- JPH0363561B2 JPH0363561B2 JP57120819A JP12081982A JPH0363561B2 JP H0363561 B2 JPH0363561 B2 JP H0363561B2 JP 57120819 A JP57120819 A JP 57120819A JP 12081982 A JP12081982 A JP 12081982A JP H0363561 B2 JPH0363561 B2 JP H0363561B2
- Authority
- JP
- Japan
- Prior art keywords
- weight
- reaction
- substance
- neutral
- lipid metabolism
- 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
- 239000000126 substance Substances 0.000 claims description 37
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 150000004676 glycans Chemical class 0.000 claims description 19
- 229920001282 polysaccharide Polymers 0.000 claims description 19
- 239000005017 polysaccharide Substances 0.000 claims description 19
- 230000000694 effects Effects 0.000 claims description 18
- 230000037356 lipid metabolism Effects 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 14
- 244000077995 Coix lacryma jobi Species 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- 235000007354 Coix lacryma jobi Nutrition 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 claims description 8
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 claims description 8
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 230000007935 neutral effect Effects 0.000 claims description 8
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 6
- 240000005979 Hordeum vulgare Species 0.000 claims description 5
- 235000007340 Hordeum vulgare Nutrition 0.000 claims description 5
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 claims description 4
- 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 4
- 238000000862 absorption spectrum Methods 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 4
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 claims description 4
- 229930182830 galactose Natural products 0.000 claims description 4
- 239000008103 glucose Substances 0.000 claims description 4
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 claims description 4
- 230000009965 odorless effect Effects 0.000 claims description 4
- 230000001766 physiological effect Effects 0.000 claims description 4
- 229910001961 silver nitrate Inorganic materials 0.000 claims description 4
- 230000009967 tasteless effect Effects 0.000 claims description 4
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 3
- 239000008176 lyophilized powder Substances 0.000 claims description 3
- 241000209205 Coix Species 0.000 claims description 2
- PBUWCVBYMDVPCL-UHFFFAOYSA-N 3-anilinophthalic acid Chemical compound OC(=O)C1=CC=CC(NC=2C=CC=CC=2)=C1C(O)=O PBUWCVBYMDVPCL-UHFFFAOYSA-N 0.000 claims 1
- 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 24
- 235000012000 cholesterol Nutrition 0.000 description 9
- 229930006000 Sucrose Natural products 0.000 description 8
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 8
- 239000005720 sucrose Substances 0.000 description 8
- 229920002488 Hemicellulose Polymers 0.000 description 6
- 241000700159 Rattus Species 0.000 description 5
- 210000004369 blood Anatomy 0.000 description 5
- 239000008280 blood Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000005018 casein Substances 0.000 description 4
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 4
- 235000021240 caseins Nutrition 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 210000002966 serum Anatomy 0.000 description 4
- 206010003210 Arteriosclerosis Diseases 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 240000007594 Oryza sativa Species 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 208000011775 arteriosclerosis disease Diseases 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000002075 main ingredient Substances 0.000 description 3
- 235000009566 rice Nutrition 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 235000019750 Crude protein Nutrition 0.000 description 2
- 208000031226 Hyperlipidaemia Diseases 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- -1 hydroalcohol Chemical compound 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 229920005610 lignin Polymers 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 231100000956 nontoxicity Toxicity 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001814 pectin Substances 0.000 description 2
- 229920001277 pectin Polymers 0.000 description 2
- 235000010987 pectin Nutrition 0.000 description 2
- 235000018102 proteins Nutrition 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 210000003462 vein Anatomy 0.000 description 2
- 239000011782 vitamin Substances 0.000 description 2
- 235000013343 vitamin Nutrition 0.000 description 2
- 229940088594 vitamin Drugs 0.000 description 2
- 229930003231 vitamin Natural products 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- LUEWUZLMQUOBSB-FSKGGBMCSA-N (2s,3s,4s,5s,6r)-2-[(2r,3s,4r,5r,6s)-6-[(2r,3s,4r,5s,6s)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(2r,4r,5s,6r)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@@H](O[C@@H]2[C@H](O[C@@H](OC3[C@H](O[C@@H](O)[C@@H](O)[C@H]3O)CO)[C@@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O LUEWUZLMQUOBSB-FSKGGBMCSA-N 0.000 description 1
- HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 description 1
- 239000001763 2-hydroxyethyl(trimethyl)azanium Substances 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 235000019743 Choline chloride Nutrition 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 229920002581 Glucomannan Polymers 0.000 description 1
- 108010023302 HDL Cholesterol Proteins 0.000 description 1
- 102000007330 LDL Lipoproteins Human genes 0.000 description 1
- 108010007622 LDL Lipoproteins Proteins 0.000 description 1
- 235000009233 Stachytarpheta cayennensis Nutrition 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 210000000941 bile Anatomy 0.000 description 1
- 239000003613 bile acid Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 150000001841 cholesterols Chemical class 0.000 description 1
- SGMZJAMFUVOLNK-UHFFFAOYSA-M choline chloride Chemical compound [Cl-].C[N+](C)(C)CCO SGMZJAMFUVOLNK-UHFFFAOYSA-M 0.000 description 1
- 229960003178 choline chloride Drugs 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000013325 dietary fiber Nutrition 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229940046240 glucomannan Drugs 0.000 description 1
- 229930182478 glucoside Natural products 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000011812 mixed powder Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000003359 percent control normalization Methods 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 235000019166 vitamin D Nutrition 0.000 description 1
- 239000011710 vitamin D Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Description
本発明は新規なハトムギ多糖物質及びこのもの
を含有する新規な脂質代謝改善剤に関する。
従来、ペクチンやグルコマンナン等のいわゆる
「ダイエタリー・フアイバー」は、血清コレステ
ロールの上昇を抑制する作用を有するといわれて
いるが、ペクチン等の作用は、まだ充分に解明さ
れていない。
また、米ぬかを原料として得られるセルロー
ス、ヘミセルロース、リグリンを主成分とする物
質にコレステロール上昇抑制作用があることも知
られている(特開昭55−141415号公報)。
本発明者らは、心臓等循環器疾患の原因と考え
られている高脂血症、動脈硬化症に対し治療効果
のある強力な脂質代謝改善剤を探求した結果、ハ
トムギぬか中より得られたハトムギ多糖物質が高
い脂質代謝改善効果を有することを見出し、そし
て、このハトムギ多糖物質が新規物質であること
を確認し、本発明をなすに至つた。
すなわち、本発明は下記性質を有するハトムギ
多糖物質である。
a 重量平均分子量:約50万
b 糖組成:キシロース36.4重量%、アラビノー
ス34.4重量%、グルコース17.6重量%、ウロン
酸7.4重量%、ガラクトース重量%、マンノー
ス(微量)
c 比旋光度:〔α〕24 D=−97.5゜
d 赤外吸収スペクトル:900cm-1及び1650cm-1
に吸収帯を有する
e 溶解性:水に可溶、アルカリ水溶液に可溶、
アセトン、ベンゼン、アルコール、含水アルコ
ール、クロロホルムにそれぞれ不溶
f 呈色反応:アニリン・フタル酸反応(+)、
アンモニア・硝酸銀反応(+)、ニンヒドリン
反応(+)、塩基第二鉄反応(±)
g 塩基性、酸性、中性の区別:中性
h 性状:白色ないし淡褐色(凍結乾燥粉末)無
味、無臭、
i 生理活性:脂質代謝改善作用
また、本発明は、ハトムギ多糖物質又は(及
び)該物質を含有する組成物を有効成分として含
む脂質代謝改善剤である。
本発明の脂質代謝改善剤は、コレステロール等
の血清指質成分に対する低下作用が極めて高く、
しかも毒性や副作用がないから、高脂血症や動脈
硬化症の治療に有効に使用することができる。
前述のように、米ぬかのヘミセルロース等にコ
レステロール上昇抑制作用があることは公知であ
るが、ハトムギぬかから優れた脂質代謝改善作用
を有する多糖物質が得られたことはこれまで報告
されていない。
本発明のハトムギ多糖物質は次の性質を有す
る。
a 高速液体クロマトグラフイー法による重量平
均分子量は約50万である。
b 糖組成は、キシロース36.4重量%、アラビノ
ース34.4重量%、グルコース17.6重量%、ウロ
ン酸7.4重量%、ガラクトース4.1重量%、マン
ノース(微量)である。
c 比旋光度〔α〕24 Dは−97.5゜(濃度88mg/100ml)
である。
d 赤外吸収スペクトルは、900cm-1にβ−D−
グルコシド結合による吸収、及び、1650cm-1に
ペプチド結合による吸収を示す。
e 溶解性については、本物質は冷水、温水に可
溶であり、このものの水溶液は若干粘性を示
す。
また、各種濃度のアルカリ水溶液に可溶であ
る。アセトン、ベンゼン、アルコール、含水ア
ルコール、クロロホロムに不溶である。
f 呈色反応については、アニリン・フタル酸反
応(+)、アンモニア・硝酸銀反応(+)、ニン
ヒドリン反応(+)、塩化第二鉄反応(±)で
ある。
g,h 本物質は、中性の物質であり、凍結乾燥
粉末化したものの色は白色ないし淡褐色であ
り、また、無味無臭である。
i 生理活性として強力な脂質代謝改善作用を示
す。
本発明の多糖物質は通常ハトムギぬかから得ら
れ、次のような方法で抽出することができる。ハ
トムギぬかを有機溶剤等で処理して脱脂した後、
化学処理又は酸素処理し、得られた処理液を過
して殿粉質等を液として除去した後残渣を得
る。この残渣を0.5Nアルカリ水溶液にとかし、
その可溶分をヘミセルロース区分として分取す
る。このものはハトムギ多糖物質を主体とし他に
粗蛋白質、リグニン、セルロース、灰分を含有す
る組成物である。このものを含むアルカリ水溶液
を中和した後蛋白質を沈殿除去し、上澄液を透折
した後エタノールを加えて本発明の多糖物質が沈
殿として取得する。
本発明はハトムギ多糖物質又は(及び)該物質
を含有する組成物と有効成分として含む脂質代謝
改善剤である。本剤は、後記実験例で示すように
経口投与により血清中の各種コレステロール、遊
離脂肪酸、中性脂肪、リン脂質及びβ−リポ蛋白
質等の値を低下させ、著しい脂質代謝改善作用を
有するものである。また、本剤には毒性や副作用
は認められない。
本発明の脂質代謝改善剤は通常経口投与され、
経口投与量は1日当り50〜100mg/体重Kgであり、
長期連用が可能である。
剤形については、通常の経口剤形が適用され、
例えば水溶剤、殿粉や乳糖とともに打錠した錠
剤、あるいは粉末剤、顆粒剤など、好ましい剤形
を選択することが可能である。
次に、脂質代謝改善作用の実験例を示す。
〔実験例A、脂質代謝改善作用〕
実験動物としてラツトを用いたが、ラツトにお
ける実験結果がヒトに相応することは、よく知ら
れいる。
体重約60gのSD系雄ラツト32匹を下記の高コ
レステロール飼料で8日間予備飼育した後、それ
ぞれ尾静脈より採血して血清コレステロール値が
平均化していることを確かめた。1郡8匹づつ4
群に分け、1群は直ちに断頭、採血し後記第1表
の測定項目について調べ測定平均値を「投与開始
時」の数値とした。多の3群については、それぞ
れ下記の対象照料A、実験飼料、同を与えて
8日間飼育し、その後に断頭、採血し同様に測定
して「投与終了時」の数値とした。
上記の飼料はこの種の実験に通常用いられてい
るもので、その組成は次のとおりである。
高コレステロール飼料:シヨ糖、カゼインを主成
分とし、コレステロール1%、胆汁酸ナトリウ
ム0.25%を含むもの
対照飼料A:シヨ糖、カゼインを主成分とするも
の
実験飼料:前記対照飼料Aのシヨ糖の一部を本
発明の物質0.5%で置換したもの
実験飼料:前記対照飼料Aのシヨ糖の一部を本
発明の物質1%で置換したもの
実験結果は第1表に示すとおりであつた。
The present invention relates to a novel adlay polysaccharide substance and a novel lipid metabolism improving agent containing this substance. Conventionally, so-called "dietary fibers" such as pectin and glucomannan have been said to have the effect of suppressing the rise in serum cholesterol, but the effects of pectin and the like have not yet been fully elucidated. It is also known that substances mainly composed of cellulose, hemicellulose, and ligrin obtained from rice bran have an effect of suppressing the rise in cholesterol (Japanese Patent Application Laid-Open No. 141415/1983). The present inventors searched for a powerful lipid metabolism improving agent that has a therapeutic effect on hyperlipidemia and arteriosclerosis, which are considered to be the causes of cardiovascular diseases such as the heart. The present inventors discovered that a coix seed polysaccharide substance has a high lipid metabolism improving effect, and confirmed that this coix seed polysaccharide substance is a new substance, leading to the present invention. That is, the present invention is a pearl barley polysaccharide substance having the following properties. a Weight average molecular weight: Approximately 500,000 b Sugar composition: xylose 36.4%, arabinose 34.4%, glucose 17.6%, uronic acid 7.4%, galactose, mannose (trace amount) c Specific optical rotation: [α] 24 D = -97.5゜d Infrared absorption spectrum: 900cm -1 and 1650cm -1
Solubility: Soluble in water, soluble in alkaline aqueous solution,
Insoluble in acetone, benzene, alcohol, hydrous alcohol, and chloroform, respectively Color reaction: Aniline/phthalic acid reaction (+),
Ammonia/silver nitrate reaction (+), ninhydrin reaction (+), ferric base reaction (±) g Basic, acidic, neutral: Neutral h Properties: White to light brown (lyophilized powder) Tasteless, odorless , i Physiological Activity: Lipid Metabolism Improving Effect The present invention is also a lipid metabolism improving agent containing a Coix barley polysaccharide substance or (and) a composition containing the substance as an active ingredient. The lipid metabolism improving agent of the present invention has an extremely high lowering effect on serum index components such as cholesterol,
Moreover, since it has no toxicity or side effects, it can be effectively used for the treatment of hyperlipidemia and arteriosclerosis. As mentioned above, it is known that rice bran hemicellulose and the like have an effect of suppressing the increase in cholesterol, but it has not been reported to date that a polysaccharide substance having an excellent lipid metabolism improving effect can be obtained from adlay bran. The adlay polysaccharide material of the present invention has the following properties. a The weight average molecular weight determined by high performance liquid chromatography is approximately 500,000. b Sugar composition is 36.4% by weight of xylose, 34.4% by weight of arabinose, 17.6% by weight of glucose, 7.4% by weight of uronic acid, 4.1% by weight of galactose, and mannose (trace amount). c Specific rotation [α] 24 D is -97.5° (concentration 88mg/100ml)
It is. d Infrared absorption spectrum shows β-D- at 900 cm -1
Absorption due to glucoside bonds and absorption due to peptide bonds at 1650 cm -1 are shown. e Regarding solubility, this substance is soluble in cold water and hot water, and an aqueous solution of this substance shows some viscosity. It is also soluble in alkaline aqueous solutions of various concentrations. Insoluble in acetone, benzene, alcohol, hydroalcohol, and chloroform. f Color reactions include aniline/phthalic acid reaction (+), ammonia/silver nitrate reaction (+), ninhydrin reaction (+), and ferric chloride reaction (±). g, h This substance is a neutral substance, and the color of the freeze-dried powder is white to light brown, and it is tasteless and odorless. i Shows a strong lipid metabolism improving effect as a physiological activity. The polysaccharide substance of the present invention is usually obtained from adlay bran and can be extracted by the following method. After degreasing pearl barley bran by treating it with an organic solvent,
After chemical treatment or oxygen treatment, the resulting treatment liquid is filtered to remove starch and the like as a liquid, and a residue is obtained. Dissolve this residue in a 0.5N alkaline aqueous solution,
The soluble content is separated as a hemicellulose fraction. This composition is mainly composed of adlay polysaccharide substances and also contains crude protein, lignin, cellulose, and ash. After neutralizing the alkaline aqueous solution containing this substance, the protein is precipitated and removed, the supernatant liquid is filtered, and ethanol is added to obtain the polysaccharide substance of the present invention as a precipitate. The present invention is a lipid metabolism improving agent containing a coix seed polysaccharide substance or/and a composition containing the substance as an active ingredient. As shown in the experimental examples below, this drug lowers the levels of various cholesterols, free fatty acids, neutral fats, phospholipids, β-lipoproteins, etc. in serum when administered orally, and has a remarkable effect on improving lipid metabolism. be. Additionally, this drug has no toxicity or side effects. The lipid metabolism improving agent of the present invention is usually orally administered,
Oral dosage is 50-100 mg/Kg body weight per day,
Long-term use is possible. Regarding the dosage form, the usual oral dosage form is applied;
For example, it is possible to select a preferred dosage form such as an aqueous solution, a tablet compressed with starch or lactose, a powder, or a granule. Next, an experimental example of the lipid metabolism improving effect will be shown. [Experimental Example A, Lipid Metabolism Improving Effect] Although rats were used as experimental animals, it is well known that the experimental results in rats are comparable to those in humans. Thirty-two SD male rats weighing approximately 60 g were preliminarily fed with the following high-cholesterol diet for 8 days, and then blood was collected from the tail vein of each rat to confirm that the serum cholesterol levels were averaged. 4, 8 fish per county
The animals were divided into groups, and one group was immediately decapitated, blood was collected, and the measurement items listed in Table 1 below were examined, and the average value of the measurements was taken as the value at "start of administration." The three groups were fed the following target food A, experimental feed, and the same for 8 days, and then decapitated, blood was collected, and measured in the same manner as the value at the end of administration. The above feed is commonly used in this type of experiment, and its composition is as follows. High-cholesterol feed: Contains sucrose and casein as main ingredients, 1% cholesterol and 0.25% sodium bile.Control feed A: Main ingredients contain sucrose and casein.Experimental feed: Contains sucrose and casein as the main ingredients. Experimental feed in which part of the sucrose in Control Feed A was replaced with 0.5% of the substance of the present invention: 1% of the substance of the present invention was substituted for part of the sucrose in Control Feed A. The experimental results were as shown in Table 1.
実験動物として体重約60gのSD系雄ラツト16
匹を用い、これを下記コレステロール無添加飼料
で10日間飼育した後、体重が平均化するように1
群8匹づつ2群に分け、1群に下記のコレステロ
ール添加飼料(対照飼料B)を投与し、投与後5
日目、9日目、18日目にラツトの尾静脈より採血
し血清コレステロール値を測定した。また、他の
1群に下記のコレステロール及び本発明物質添加
飼料(実験飼料)を投与し、同様にして5日目、
9日目、18日目の血清コレステロール値を測定し
た。
コレステロール無添加飼料:カゼイン22%、ラー
ド9%、コーン油(ビタミンA、D、E含有)
1%、塩類混合物4%、ビタミン混合物(ハー
パー配合:水溶液ビタミンをすべて含有)0.85
%、塩化コリン0.15%、シヨ糖63%
対照飼料B:前記コレステロール無添加飼料にお
いてシヨ糖を61.75%とし、コレステロール1
%及び胆汁酸ナトリウム0.25%を追加したもの
実験飼料:前記対照飼料Bにおいてシヨ糖を
61.25%とし、本発明の物質0.5%を追加したも
の
実験結果は第2表に示すとおりであつた。
SD male rat 16 weighing approximately 60g as experimental animal.
After raising them on the following cholesterol-free feed for 10 days,
Divide into 2 groups of 8 animals each, and administer the following cholesterol-added feed (control feed B) to one group.
On days 9, 9, and 18, blood was collected from the rat's tail vein and serum cholesterol levels were measured. In addition, the following cholesterol and the present invention substance-added feed (experimental feed) were administered to another group, and in the same manner, on the 5th day,
Serum cholesterol levels were measured on the 9th and 18th days. Cholesterol-free feed: 22% casein, 9% lard, corn oil (contains vitamins A, D, and E)
1%, salt mixture 4%, vitamin mixture (Harper formulation: contains all aqueous vitamins) 0.85
%, choline chloride 0.15%, sucrose 63% Control feed B: In the above cholesterol-free feed, sucrose was 61.75%, and cholesterol 1
% and 0.25% sodium bile acid.Experimental feed: In the control feed B, sucrose was added to
61.25% and 0.5% of the substance of the present invention was added.The experimental results were as shown in Table 2.
【表】
第2表によれば、9日目、18日目の血清コレス
テロール値は、推計学的処理による有意差の検討
を行なつた結果5%という小さい危険率で有意に
低い値であつた。以上の結果から、本物質は、血
清コレステロールの上昇を抑制すると判断され
る。
さらに、実験終了後、断頭採血し、血清分離
後、総コルステロール及びHDL−コレステロー
ル値の分析を実施し、動脈硬化指数を算出した。
その結果は、以下のとおりである。[Table] According to Table 2, the serum cholesterol levels on the 9th and 18th days were significantly lower values with a small risk rate of 5%, as a result of examining the significant difference using stochastic processing. Ta. From the above results, it is determined that this substance suppresses the increase in serum cholesterol. Furthermore, after the experiment was completed, blood was collected by decapitation, serum was separated, and total cholesterol and HDL-cholesterol levels were analyzed to calculate arteriosclerosis index. The results are as follows.
ハトムギぬか400gにn−ヘキサン4を加え、
一晩放置し脱脂を行つた。次いでn−ヘキサンを
完全に除去して脱脂ぬか200gを得た。
この脱脂ぬか100gに0.1重量%グリコアミラー
ゼ水溶液5及びトルエン数滴を加え、よく撹拌
した後、恒温器内で40℃、24時間酸素反応をさせ
た。得られた反応液をガラスフイルターで過
し、残渣を水洗後、0.5N水酸化ナトリウム溶液
1中に加えた。この液を、窒素ガスを充填した
容器内に入れ密詮した後、室温で18時間振とう
し、アルカリ可溶のヘミセルロース区分を抽出し
た。このものはハトムギ多糖物質含有組成物であ
り、ハトムギ多糖物質67.9重量%、粗蛋白質23.3
重量%(全窒素量×5.83)、リグニン11.1重量%、
セルロース0.4重量%、灰分3.4重量%を含むもの
であつた。
前記ヘミセルロース区分抽出液を遠心分離し沈
殿を除去した後、上澄液を氷酢酸で中和し、次い
でトリクロル酢酸を最終濃度が7重量%となるよ
う添加し蛋白質を沈殿除去した。得られた上澄液
を3日間透析した後、99.5重量%エタノール溶液
を4倍量添加して沈殿を得た。この沈殿を蒸溜水
200mlに溶解した後、液を凍結乾燥したところ淡
褐色の粉末物質5gを得た。
このものはハトムギ多糖物質の前記諸性質を有
していた。
実施例 2
〔剤の製造〕
打錠用配合粉末(バレイシヨ殿粉51%、乳糖30
%、アビセル8%、デキストリン8.5%、ステア
リン酸マグネシウム0.5%、炭酸カルシウム2%
の混合粉末)500gに、実施例1で得られた多糖
物質5g又は該物質含有組成物5gを均一に混合
し、直接打錠機を用いて打錠して、それぞれ錠剤
を得た。
本発明のハトムギ多糖物質を有効成分とする剤
は、下記第4表にみるとおり、血清総コレステロ
ール低下効果において米ぬかヘミセルロースより
も明らかにまさつており、優れた脂質代謝改善効
果を有するものである。
Add n-hexane 4 to 400g of pearl barley bran,
It was left overnight to degrease. Next, n-hexane was completely removed to obtain 200 g of defatted bran. To 100 g of this defatted bran, 0.1% by weight glycoamylase aqueous solution 5 and several drops of toluene were added, stirred thoroughly, and then subjected to an oxygen reaction at 40° C. for 24 hours in a thermostatic chamber. The resulting reaction solution was filtered through a glass filter, and the residue was washed with water and then added to 0.5N sodium hydroxide solution 1. This liquid was placed in a container filled with nitrogen gas, tightly sealed, and then shaken at room temperature for 18 hours to extract the alkali-soluble hemicellulose fraction. This is a composition containing adlay polysaccharide substances, with 67.9% by weight of adlay polysaccharide substances and 23.3% crude protein.
Weight% (total nitrogen amount x 5.83), lignin 11.1% by weight,
It contained 0.4% by weight of cellulose and 3.4% by weight of ash. After centrifuging the hemicellulose fraction extract to remove precipitates, the supernatant was neutralized with glacial acetic acid, and then trichloroacetic acid was added to a final concentration of 7% by weight to precipitate and remove proteins. After the obtained supernatant was dialyzed for 3 days, 4 times the amount of 99.5% by weight ethanol solution was added to obtain a precipitate. Dilute this precipitate with distilled water
After dissolving in 200 ml, the liquid was freeze-dried to obtain 5 g of a light brown powder substance. This substance had the above-mentioned properties of the adlay polysaccharide substance. Example 2 [Manufacture of drug] Compound powder for tableting (51% potato starch, 30% lactose)
%, Avicel 8%, Dextrin 8.5%, Magnesium stearate 0.5%, Calcium carbonate 2%
5 g of the polysaccharide substance obtained in Example 1 or 5 g of the substance-containing composition were uniformly mixed with 500 g of the mixed powder of 100 g of the polysaccharide obtained in Example 1, and the mixture was directly compressed using a tablet machine to obtain tablets. As shown in Table 4 below, the agent of the present invention containing the adlay polysaccharide substance as an active ingredient is clearly superior to rice bran hemicellulose in reducing serum total cholesterol, and has an excellent lipid metabolism improving effect.
【表】
は投与9日目の値である。
[Table] shows the values on the 9th day of administration.
Claims (1)
ス34.4重量%、グルコース17.6重量%、ウロン
酸7.4重量%、ガラクトース4.1重量%、マンノ
ース(微量) c 比旋光度:〔α〕24 D=−97.5゜ d 赤外吸収スペクトル:900cm-1及び1650cm-1
に吸収帯を有する e 溶解性:水、アルカリ水溶液にそれぞれ可
溶、アセトン、ベンゼン、アルコール、含水ア
ルコール、クロロホルムにそれぞれ不溶 f 呈色反応:アニリン・フタル酸反応(+)、
アンモニア・硝酸銀反応(+)、ニンヒドリン
反応(+)、塩化第二鉄反応(±) g 塩基性、酸性、中性の区別:中性 h 性状:白色ないし淡褐色(凍結乾燥粉末)無
味、無臭、 i 生理活性:脂質代謝改善作用 2 下記性質を有するハトムギ多糖物質又は(及
び)該物質を含有する組成物を有効成分として含
む脂質代謝改善剤。 a 重量平均分子量:約50万 b 糖組成:キシロース36.4重量%、アラビノー
ス34.4重量%、グルコース17.6重量%、ウロン
酸7.4重量%、ガラクトース4.1重量%、マンノ
ース(微量) c 比旋光度:〔α〕24 D=−97.5゜ d 赤外吸収スペクトル:900cm-1及び1650cm-1
に吸収帯を有する e 溶解性:水に可溶、アルカリ水溶液に可溶、
アセトン、ベンゼン、アルコール、含水アルコ
ール、クロロホルムにそれぞれ不溶 f 呈色反応:アニリン・フタル酸反応(+)、
アンモニア・硝酸銀反応(+)、ニンヒドリン
反応(+)、塩化第二鉄反応(±) g 塩基性、酸性、中性の区別:中性 h 性状:白色ないし淡褐色(凍結乾燥粉末)無
味、無臭、 i 生理活性:脂質代謝改善作用[Scope of Claims] 1. Coix barley polysaccharide substance having the following properties. a Weight average molecular weight: Approximately 500,000 b Sugar composition: xylose 36.4% by weight, arabinose 34.4% by weight, glucose 17.6% by weight, uronic acid 7.4% by weight, galactose 4.1% by weight, mannose (trace amount) c Specific rotation: [α] 24 D = -97.5゜d Infrared absorption spectrum: 900cm -1 and 1650cm -1
Solubility: Soluble in water and alkaline aqueous solution, insoluble in acetone, benzene, alcohol, hydrous alcohol, and chloroform Color reaction: Aniline-phthalic acid reaction (+),
Ammonia/silver nitrate reaction (+), ninhydrin reaction (+), ferric chloride reaction (±) g Basic, acidic, neutral: Neutral h Properties: White to light brown (lyophilized powder) Tasteless, odorless , i Physiological activity: Lipid metabolism improving effect 2 A lipid metabolism improving agent comprising, as an active ingredient, a adlay polysaccharide substance having the following properties or (and) a composition containing the substance. a Weight average molecular weight: Approximately 500,000 b Sugar composition: xylose 36.4% by weight, arabinose 34.4% by weight, glucose 17.6% by weight, uronic acid 7.4% by weight, galactose 4.1% by weight, mannose (trace amount) c Specific rotation: [α] 24 D = -97.5゜d Infrared absorption spectrum: 900cm -1 and 1650cm -1
Solubility: Soluble in water, soluble in alkaline aqueous solution,
Insoluble in acetone, benzene, alcohol, hydrous alcohol, and chloroform, respectively Color reaction: Aniline/phthalic acid reaction (+),
Ammonia/silver nitrate reaction (+), ninhydrin reaction (+), ferric chloride reaction (±) g Basic, acidic, neutral: Neutral h Properties: White to light brown (lyophilized powder) Tasteless, odorless , i Physiological activity: lipid metabolism improvement effect
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP57120819A JPS5911302A (en) | 1982-07-12 | 1982-07-12 | Adlay polysaccharide substance and lipometabolism improver |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP57120819A JPS5911302A (en) | 1982-07-12 | 1982-07-12 | Adlay polysaccharide substance and lipometabolism improver |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5911302A JPS5911302A (en) | 1984-01-20 |
JPH0363561B2 true JPH0363561B2 (en) | 1991-10-01 |
Family
ID=14795743
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP57120819A Granted JPS5911302A (en) | 1982-07-12 | 1982-07-12 | Adlay polysaccharide substance and lipometabolism improver |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS5911302A (en) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2764433B2 (en) * | 1989-05-12 | 1998-06-11 | 花王株式会社 | Autoimmune disease therapeutic agent |
US6982254B2 (en) * | 2003-02-18 | 2006-01-03 | The Procter & Gamble Company | Compositions comprising a plurality of particles or agglomerates having a defined particle size |
US7879370B2 (en) * | 2006-04-26 | 2011-02-01 | Merican Corporation | Composition of which chief ingredient is polysaccharides having an immunoregulatory function |
CN106337309B (en) * | 2015-07-08 | 2018-03-09 | 中国中医科学院西苑医院 | A kind of high-purity and in high yield Job's tears water-soluble cellulose preparation method |
-
1982
- 1982-07-12 JP JP57120819A patent/JPS5911302A/en active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS5911302A (en) | 1984-01-20 |
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