JPH03145424A - Saccharide absorption inhibitor - Google Patents
Saccharide absorption inhibitorInfo
- Publication number
- JPH03145424A JPH03145424A JP1285759A JP28575989A JPH03145424A JP H03145424 A JPH03145424 A JP H03145424A JP 1285759 A JP1285759 A JP 1285759A JP 28575989 A JP28575989 A JP 28575989A JP H03145424 A JPH03145424 A JP H03145424A
- Authority
- JP
- Japan
- Prior art keywords
- sugar
- phenyl glucoside
- compound
- absorption inhibitor
- glucoside compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000010521 absorption reaction Methods 0.000 title claims abstract description 22
- 150000001720 carbohydrates Chemical class 0.000 title claims abstract description 11
- 239000003112 inhibitor Substances 0.000 title claims abstract description 10
- 235000000346 sugar Nutrition 0.000 claims abstract description 35
- -1 phenyl glucoside compound Chemical class 0.000 claims abstract description 19
- BJRNKVDFDLYUGJ-RMPHRYRLSA-N hydroquinone O-beta-D-glucopyranoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=C(O)C=C1 BJRNKVDFDLYUGJ-RMPHRYRLSA-N 0.000 claims abstract description 9
- 235000013379 molasses Nutrition 0.000 claims abstract description 6
- BJRNKVDFDLYUGJ-UHFFFAOYSA-N p-hydroxyphenyl beta-D-alloside Natural products OC1C(O)C(O)C(CO)OC1OC1=CC=C(O)C=C1 BJRNKVDFDLYUGJ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229960000271 arbutin Drugs 0.000 claims abstract description 3
- 238000000605 extraction Methods 0.000 claims description 5
- 150000008163 sugars Chemical class 0.000 claims description 5
- 150000008505 β-D-glucopyranosides Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 12
- 239000003463 adsorbent Substances 0.000 abstract description 5
- 239000005445 natural material Substances 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 14
- 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 13
- 229930006000 Sucrose Natural products 0.000 description 12
- 230000002401 inhibitory effect Effects 0.000 description 10
- 239000005720 sucrose Substances 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- 239000008103 glucose Substances 0.000 description 8
- 239000012528 membrane Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 239000007983 Tris buffer Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 6
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 5
- NEZJDVYDSZTRFS-RMPHRYRLSA-N Phenyl beta-D-glucopyranoside Chemical class O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=CC=C1 NEZJDVYDSZTRFS-RMPHRYRLSA-N 0.000 description 5
- 229940125782 compound 2 Drugs 0.000 description 5
- 210000002472 endoplasmic reticulum Anatomy 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 210000000110 microvilli Anatomy 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 230000006377 glucose transport Effects 0.000 description 3
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000002285 radioactive effect Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000004809 Teflon Substances 0.000 description 2
- 229920006362 Teflon® Polymers 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 229920001429 chelating resin Polymers 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 230000002950 deficient Effects 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 210000001630 jejunum Anatomy 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000004044 tetrasaccharides Chemical class 0.000 description 2
- ZAYNPHFMMZKFEZ-UJPOAAIJSA-N (2R,3R,4S,5S,6R)-2-(4-hydroxy-3-methoxyphenyl)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol Chemical compound COC=1C=C(C=CC1O)[C@]1(O)[C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO ZAYNPHFMMZKFEZ-UJPOAAIJSA-N 0.000 description 1
- KWVHACHAQJFTLZ-UJPOAAIJSA-N (2s,3r,4s,5s,6r)-2-(4-hydroxy-3-methoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C1=C(O)C(OC)=CC(O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=C1 KWVHACHAQJFTLZ-UJPOAAIJSA-N 0.000 description 1
- LWEHRPZXRYZMDC-UHFFFAOYSA-N (4-hydroxy-2-methoxy-phenyl)-beta-D-glucopyranoside Natural products COC1=CC(O)=CC=C1OC1C(O)C(O)C(O)C(CO)O1 LWEHRPZXRYZMDC-UHFFFAOYSA-N 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 240000003550 Eusideroxylon zwageri Species 0.000 description 1
- 101000851376 Homo sapiens Tumor necrosis factor receptor superfamily member 8 Proteins 0.000 description 1
- 206010060378 Hyperinsulinaemia Diseases 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- 102100036857 Tumor necrosis factor receptor superfamily member 8 Human genes 0.000 description 1
- GVBNSPFBYXGREE-CXWAGAITSA-N Visnadin Chemical compound C1=CC(=O)OC2=C1C=CC1=C2[C@@H](OC(C)=O)[C@@H](OC(=O)[C@H](C)CC)C(C)(C)O1 GVBNSPFBYXGREE-CXWAGAITSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 201000008980 hyperinsulinism Diseases 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 210000003097 mucus Anatomy 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- OQUKIQWCVTZJAF-UHFFFAOYSA-N phenol;sulfuric acid Chemical compound OS(O)(=O)=O.OC1=CC=CC=C1 OQUKIQWCVTZJAF-UHFFFAOYSA-N 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 235000014347 soups Nutrition 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000012089 stop solution Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- KWVHACHAQJFTLZ-QNWJLWSRSA-N tachioside Natural products O(C)c1c(O)ccc(O[C@H]2[C@@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O2)c1 KWVHACHAQJFTLZ-QNWJLWSRSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Abstract
Description
【発明の詳細な説明】
［発明の属する技術分野］
本発明は、糖類の体内での吸収を抑制する糖類吸収抑制
剤に関するものである。DETAILED DESCRIPTION OF THE INVENTION [Field of the Invention] The present invention relates to a saccharide absorption inhibitor that suppresses the absorption of saccharides in the body.
［従来技術］
近年の精製技術の進歩に伴い、純粋な白砂糖が１Ｆ味料
として利用されているが、最近、この精製白砂糖の多晴
摂取によって肥満・抗脂血症等の種々の病態が引き起こ
される事が指摘されている。[Prior art] With the recent advances in refining technology, pure white sugar has been used as a 1F flavoring agent, but recently, the intake of refined white sugar has been associated with various pathological conditions such as obesity and antilipidemia. It has been pointed out that this can be caused.
しかしながら、体内におけるＩＲ類の吸収を抑制する安
全性の高い抑１１１剤は現在のところ得られていない。However, a highly safe 111 inhibitor that suppresses the absorption of IRs in the body has not yet been obtained.
［発明が解決しようとする課題］
本発明は、体内における糖類の吸収を効果的に抑制する
ことのできる安全性の高い糖類吸収抑制剤を提供するこ
とを課題としている。[Problems to be Solved by the Invention] An object of the present invention is to provide a highly safe saccharide absorption inhibitor that can effectively suppress the absorption of saccharides in the body.
［課題を解決するための手段］
本発明にかかる糖類吸収抑制剤は、粗糖、糖蜜等Ｊ目り
製糖から抽出によって得られるフェニルグルコシド化合
物を必須成分とする。古くから汁昧料として用いられて
きた未結製の黒砂糖中には高インスリン血症抑制作用・
糖吸収抑−１作用を有する物質が含まれていることが知
られている。これらの作用物質として３．４−ジメトキ
シフェニル−〇−０−グルコース及び３，４．６−ドリ
メトキシフエニルー０−〇−グルコースが午芝されると
ともに、こわら２つの化合物の他にも上記作用を有する
化合物が黒砂糖中に存在する事が報告されている（Ｙ、
キムラ他、プランタ メゾイカ（ＰＩａｎＬａ Ｍｅ
ｄｉｃａ）、 ５０，４６９−４７：１．１９８４）
。[Means for Solving the Problems] The saccharide absorption inhibitor according to the present invention has as an essential component a phenyl glucoside compound obtained by extraction from J-mesh refined sugar such as raw sugar and molasses. Uncured brown sugar, which has been used as a soup additive since ancient times, has hyperinsulinemia-suppressing effects.
It is known that it contains a substance that has a sugar absorption inhibitory effect. These active substances include 3,4-dimethoxyphenyl-0-0-glucose and 3,4,6-dimethoxyphenyl-0-0-glucose, as well as the two compounds mentioned above. It has been reported that compounds with this effect exist in brown sugar (Y,
Kimura et al., Planta Mezoica (PIanLa Me
dica), 50, 469-47:1.1984)
.
本発明におけるフェニルグルコシド化合物として、発明
者等はタキオサイド（Ｌａｃｈｉｏｓｉｄｅ）［（３−
メトキシ（ＩＩＩｅ ｔｈｏｘｙ） ４ヒドロキシフ
エニル（ｈｙｄｒｏｘｙｐｈｅｎｙｌ） ）−β−Ｄ−
グルコピラノシド（ｇｌｕｃｏｐｙｒａｎｏｓｉｄｅ）
］及びアルブチン（ａｒｂｕＬｉｎ） （４ヒドロ
キシフエニル（ｈｙｄｒｏｘｙｐｈｅｎｙ ｌ）β−Ｄ
−グルコピラノシド（ｇｌｕｃｏｐｙｒａｎｏｓｉｄｅ
））が効果的であることを見出した。以下、具体例を挙
げつつこの発明について３Ｔ’細に説明する。As the phenyl glucoside compound in the present invention, the inventors have selected tachioside [(3-
Methoxy(IIIe thoxy) 4hydroxyphenyl)-β-D-
glucopyranoside
] and arbutin (4 hydroxyphenyl β-D
-glucopyranoside
)) was found to be effective. Hereinafter, this invention will be explained in detail with reference to specific examples.
本発明において使用するフェニルグルコシド化合物は、
例えば次のようにして得られる。The phenyl glucoside compound used in the present invention is
For example, it can be obtained as follows.
まず粗糖、糖蜜等の非精製糖を通常、砂糖黍または甜菜
から準備調整する。この非精製糖を適当量の水に溶解し
、これを吸着剤に吸着させたあと吸着剤を水洗して糖分
を除去する。そのあと２０〜３０本の低級アルコール次
いで９５〜９９％の低級アルコールにより非蔗糖画分を
溶出させる。使用する吸着剤としては、非極性のポリス
チレン系樹脂吸着剤例えばアンバーライトＸへＤ−１，
アンバーライトＸＡＤ−２（ロームアンド ハース社製
）及びセルバＸへＤ−２（セルバ社製）が好適である。First, unrefined sugar such as raw sugar or molasses is prepared, usually from sugar cane or sugar beet. This unrefined sugar is dissolved in an appropriate amount of water, adsorbed onto an adsorbent, and then the adsorbent is washed with water to remove the sugar content. Thereafter, the non-sucrose fraction is eluted with 20 to 30 lower alcohols and then 95 to 99% lower alcohol. The adsorbent used is a non-polar polystyrene resin adsorbent such as Amberlite X to D-1,
Amberlite XAD-2 (manufactured by Rohm and Haas) and Selva X to D-2 (manufactured by Selva) are suitable.
また、非１．？？糖画分は非精製糖を適量の水に溶解し
、これに５倍量のエタノールを加え蔗糖を沈澱させ、そ
のｌｊＱみとして得ることができる。この場合、まだ相
当晴の糖分が非蔗糖画分に含まれるのでさらに活性炭カ
ラムにより糖分を除去する必要がある。すなわち、上記
の方法で得た非虚糖画分を活性炭に吸着させたあと水洗
して糖分を除去し、そのあと低級アルコールにより非ｊ
、４糖両分を溶出させる。Also, non-1. ? ? The sugar fraction can be obtained by dissolving unrefined sugar in an appropriate amount of water and adding 5 times the volume of ethanol to precipitate sucrose. In this case, since a considerable amount of sugar is still contained in the non-sucrose fraction, it is necessary to further remove the sugar using an activated carbon column. That is, the non-deficient sugar fraction obtained by the above method is adsorbed on activated carbon, washed with water to remove the sugar content, and then the non-deficient sugar fraction obtained by the above method is removed using lower alcohol.
, both tetrasaccharides are eluted.
このようにして得られた非し４糖両分をシリカゲルカラ
ムクロマト及び／または逆相１１１１１．Ｇで精製分別
することにより、フェニルグルコシド化合物を得ること
ができるのである。Both non-tetrasaccharide components thus obtained were subjected to silica gel column chromatography and/or reverse phase chromatography. By purifying and fractionating with G, phenyl glucoside compounds can be obtained.
本発明において得られたフェニルグルコシド化合物は、
常法の定性分析によりＬａｃｈｉｏｓｉｄｅ（（３−ｍ
ｅｔｈｏｘｙ−４−ｈｙｄｒｏｘｙｐｈｅｎｙｌ）−β
−Ｄ−ｇｌｕｃｏｐｙｒａｎｏｓ １ｄｅ）及びａｒｂ
ｕＬｉｎ （４−ｈｙｄｒｏｘｙｐｈｅｎｙｌ−β−Ｄ
−ｇｌ ｕｃｏｐｙｒａｎｏｓｉｄｅ）と同定された。The phenyl glucoside compound obtained in the present invention is
Lachioside ((3-m
ethoxy-4-hydroxyphenyl)-β
-D-glucopyranos 1de) and arb
uLin (4-hydroxyphenyl-β-D
-glucopyranoside).
本発明においてこれらのフェニルグルコシド化合物は、
有機合成法によってフェニル基とグルコシル基を化学的
にエーテル結合させたものであってもよく、その合成方
法としては特に限定されるものではない。In the present invention, these phenyl glucoside compounds are
It may be one in which a phenyl group and a glucosyl group are chemically bonded to an ether bond by an organic synthesis method, and the synthesis method is not particularly limited.
［作用］
本発明における必須成分であるフェニルグルコシド化合
物が体内における糖類の吸収を抑制するメカニズムは必
ずしも明確ではないが、これらフェニルグルコシド化合
物は糖であるグルコースと化学的に構造が似ているので
、小腸内で糖とともに吸収される結果その分だけ糖の吸
収を阻害するのであろうと考えられる。[Effect] Although the mechanism by which phenyl glucoside compounds, which are essential components of the present invention, suppress the absorption of sugars in the body is not necessarily clear, these phenyl glucoside compounds have chemical structures similar to the sugar glucose, so It is thought that as a result of being absorbed together with sugar in the small intestine, it inhibits sugar absorption.
［効果］
上記粗糖、糖蜜等非錆製糖から抽出によって得られるフ
ェニルグルコシド化合物は、以下の実施例でも明らかな
ようにすぐれた糖類吸収抑制効果を有するものであり、
しかもこのフェニルグルコシド化合物は、本来天然物か
ら抽出されるものであるから極めて安全性が高く、服用
に適したものである。[Effect] The phenyl glucoside compound obtained by extraction from the above-mentioned raw sugar, molasses, and other non-rusted sugars has an excellent sugar absorption inhibitory effect, as is clear from the following examples.
Moreover, since this phenyl glucoside compound is originally extracted from a natural product, it is extremely safe and suitable for administration.
［実ｊＭ例］ つぎに、本発明の実施例及び試験例について説明する。[Actual jM example] Next, Examples and Test Examples of the present invention will be described.
（１）非蔗糖画分の抽出
黒砂糖１ｋｇを５００ｍｊ２の蒸留水に溶解し、それに
２．５ Ｊ２のエタノールを加え、蔗糖を沈澱させた。(1) Extraction of non-sucrose fraction 1 kg of brown sugar was dissolved in 500 mJ2 of distilled water, and 2.5 J2 of ethanol was added thereto to precipitate sucrose.
Ｌ清を１６，０ＯＯＸＩ（、１０分間遠心し、その−ト
清をロータリーエバポレーターで濃縮したもの（非蔗糖
画分）を３６０ｇ得た。The L supernatant was centrifuged for 10 minutes at 16,0 OOXI, and the supernatant was concentrated using a rotary evaporator to obtain 360 g of a non-sucrose fraction.
（２）非蔗糖画分の活性炭カラムクロマト非１，７に糖
両分３６０ｇを水２００ＩＩＩ１．に溶解し、活性炭１
６０ｇを充填した内径４．２ｃｍのカラムに注入し、吸
着させた。次に水ＩＩｔを流下させたあと、１（２ｆｆ
ｉ）。(2) Activated carbon column chromatography for non-sucrose fraction. Add 360 g of both sugar fractions to 1.7 and 200 g of water. Dissolved in activated carbon 1
It was injected into a column with an inner diameter of 4.2 cm packed with 60 g and adsorbed. Next, after letting water IIt flow down, 1 (2ff
i).
１０！ｋ（ｌ１Ｚ）、２０’Ｊ（１ｆｆｉ）、：１０９
６（ｌｆｆ１）、４０’！（：１Ｊ２）、＋００！ｋ（
６１）エタノールを順次流下させた。溶出液を１００ｒ
ａｌずつ分取し、フェニル基に基づ（２７５ｎｍ吸光度
とフェノール硫酸法による４９０ｎｍの吸光度によって
フェニルグルコシド化合物と蔗糖の検出を行った（第１
図参照）。10! k(l1Z), 20'J(1ffi), :109
6 (lff1), 40'! (:1J2), +00! k(
61) Ethanol was allowed to flow down sequentially. Eluate at 100r
phenyl glucoside compounds and sucrose were detected based on the phenyl group (275 nm absorbance and 490 nm absorbance using the phenol-sulfuric acid method).
(see figure).
蔗糖は５２本０までの両分に溶出され、５３木目以降の
両分を第１図に示す溶出パターンにより５３〜６２、６
：１〜６９．７０〜１００．１０１〜１０５．１０６〜
１５４本日の５つの両分に分画した。この５つの分画を
ＴＬＣ上で比較したところ（第２図参照）、５３〜６２
．６３〜６９本目の両分は原点付近にとどまり展開しな
かったが、７０〜＋００． ｌｏｔ〜１０５．１０６〜
１５４木目の両分はいずれも３．４−ジメトキシフェニ
ル−〇−Ｄ−グルコースを主成分とする混合物であった
。第１表に示すようにいずれの両分にも糖吸収抑制効果
は認められた。より効果の強かワた７０〜１００．１０
１〜１０５．１０６〜１５４本日の３つの両分を１つに
まとめ、この両分から未同定の化合物を単離するためシ
リカゲルカラムクロマト（クロロホルム／メタノール系
の溶出液使用）及び逆相ＨＰ ＬＣ（０，１！ｋＴＦＡ
を含む水／アセトニトリル系の溶出液使用）を行ない、
Ｌａｃｈｉｏｓｉｄｅ （化合物１）及びａｒｂｕｔｉ
ｎ（化合物２）を精製分別した。これら２つの化合物の
同定方法を以下に記す。Sucrose was eluted in both portions up to 52 grains, and both portions from grain 53 onwards were eluted from 53 to 62 and 6 according to the elution pattern shown in Figure 1.
:1~69.70~100.101~105.106~
154 Today's fraction was divided into five fractions. When these five fractions were compared on TLC (see Figure 2), 53-62
．． The 63rd to 69th lines stayed near the origin and did not develop, but 70 to +00. lot～105.106～
Both grains of grain 154 were mixtures containing 3,4-dimethoxyphenyl-〇-D-glucose as a main component. As shown in Table 1, sugar absorption inhibitory effects were observed in both doses. Stronger effect 70-100.10
1-105.106-154 Today's three two parts were combined into one, and in order to isolate unidentified compounds from these two parts, silica gel column chromatography (using chloroform/methanol-based eluent) and reversed phase HP LC ( 0,1!kTFA
(using a water/acetonitrile-based eluent containing
Lachioside (compound 1) and arbuti
n (compound 2) was purified and fractionated. The method for identifying these two compounds is described below.
同定方法
（１）化合物ｌ
化合物ｌは’ＩＩ−ＮＭＲ（２７０ＭＩ＋、、ＣＤ３０
Ｄ）よりβ結合したグルコシル、！、１． （δ３．３
０−３．５０ （４１１，ｍ） 、：１．６７ （ＩＩ
Ｉ、ｄｄ、、Ｉ＝５．１９．１１．９１１．、） 、：
１．８６ （ＩＩＩ、ｄｄ、Ｊ−２，１４，１１，９１
１□）、４゜７３ （１１１，ｄ、Ｊ−７，６３１１□
））、１つのメトキシル基（３，８２（：ｌｌｌ 、Ｓ
） ） 、 ３置換ベンゼン（６，５７（ＩＩＩ、ｄｄ
、Ｊ−２，７５，８，５４１１□）、６．６８（＋１１
．ｄ、Ｊ−８，５４１１□）、６．７９ （ＩＩＩ、ｄ
、Ｊ−２，７５））のシグナルが観測され、ベンゼン環
プロトンのカップリングパターン及びＮ０ＩＥＳＹにお
いてベンゼン環の２位のプロトンとメトキシル基にＮＯ
Ｅが観測されることから（３−ｍｃｌ、ｈｏｘｙ−４−
！＋ｙｄｒｏｘｙｐｈｃｎｙｌ） −β−Ｄ−ｇｌｕｃ
ｏｐｙｒａｎｏｓ ｉｄｅと推定された。この化合物は
既にＬａｃｈ ｉｏｓ ｉｄｅとしてくるうめもどき科
りマヤナギから単離・構造決定されており（Ｐｈｙｔｏ
ｃｈｅｍｉｓｔｒｙ、Ｖｏｌ 、２６．Ｎｏ、ＩＯ，ｐ
ｐ、２８１１−２８１４．１９８７）、そのスペクトル
データーが化合物１と一致したので化合物１をｔａｃｈ
ｉｏｓｉｄｅと同定した。Identification method (1) Compound l Compound l is 'II-NMR (270MI+, CD30
D) more β-linked glucosyl,! , 1. (δ3.3
0-3.50 (411, m) , :1.67 (II
I, dd,, I=5.19.11.911. , ) , :
1.86 (III, dd, J-2, 14, 11, 91
1□), 4゜73 (111, d, J-7, 6311□
)), one methoxyl group (3,82(:llll, S
) ), 3-substituted benzene (6,57(III, dd
, J-2,75,8,5411□), 6.68 (+11
．． d, J-8,5411□), 6.79 (III, d
, J-2, 75)) was observed, and in the coupling pattern of the benzene ring proton and the NOIESY, the proton at the 2-position of the benzene ring and the methoxyl group
Since E is observed (3-mcl, hoxy-4-
! +ydroxyphcnyl) -β-D-gluc
It was presumed to be opyranoside. This compound has already been isolated and its structure determined from the Lach ios ide (Phytophylla sinensis).
Chemistry, Vol. 26. No, IO, p
p, 2811-2814.1987), and the spectral data matched that of compound 1, so compound 1 was touched.
It was identified as ioside.
（２）化合物２
化合物２は１１トＮＭＲ（２７０Ｍｌｌ。、ｃｏ３ｏｏ
）よりβ結合したグルコシル基（δ３．３０−３．５０
（４１１，ＬＤ） 、：１．６Ｂ（ＩＩＩ、ｍ。(2) Compound 2 Compound 2 has 11t NMR (270Mll., co3oo
) to β-bonded glucosyl group (δ3.30-3.50
(411, LD) , :1.6B (III, m.
、３．８７ （ＩＨ，Ｊ−１１，：１ｏＩｌｚ） 、４
．７２（ｄ、Ｊ＝７．６３）） 、ノ＼う２置換ベンゼ
ン（６，６７（２１１，ｄ−１ｉｋｅ 、Ｊ−８，８５
Ｈ２） 、６．９５ （２１量。, 3.87 (IH, J-11,:1oIlz) , 4
．． 72(d, J=7.63)), ＼disubstituted benzene (6,67(211,d-1ike, J-8,85
H2), 6.95 (21 amounts.
ｄ−ｌｉｋｅ、Ｊ−８，８５））のシグナルか観測され
、ベンゼン環プロトンのカップリングツ（ターン力１ら
、４−ｈｙｄｒｏｘｙｐｈｅｎｙｌ−β−Ｄ−ｇｌｕｃ
ｏｐｙｒａｎｏｓ ｉｄｃと推定された。この化合物は
既にａｒｂｕＬｉｎとして知られており東京化成工業社
のａｒｂｕＬｉｎと化合物２のスペクトルデーターを比
較したところ一致したので化合物２をａｒｂｕＬｉｎと
同定した。d-like, J-8, 85)) was observed, and a coupling signal of the benzene ring proton (turn force 1 et al., 4-hydroxyphenyl-β-D-gluc) was observed.
It was presumed to be opyranos idc. This compound is already known as arbuLin, and when the spectrum data of Tokyo Kasei Kogyo Co., Ltd.'s arbuLin and Compound 2 were compared, they matched, so Compound 2 was identified as arbuLin.
これら２つの化合物の糖吸収に対する作用はこてまでに
報告がなく、今回、試験したところ第２表に示すように
グルコース吸収の抑制効果を示した。There have been no reports on the effects of these two compounds on sugar absorption, and when tested this time, they showed an inhibitory effect on glucose absorption as shown in Table 2.
試験例
糖吸収の抑制効果は以下に示すラットの空腸刷７−！ｊ
膜より調整した小胞体におけるグルコース輸送阻害活性
によって調べた。Test Example: The inhibitory effect on sugar absorption was shown below in rat jejunal imprint 7-! j
It was investigated by the glucose transport inhibitory activity in the endoplasmic reticulum, which was prepared from the membrane.
（１）空腸刷ｆ縁１漠の調整
以下の操作はすべて０〜４℃で行なった。２００ｇ＋ｆ
ｒ後のラットから死後直ちに空腸を取り出し、管空内を
生理食塩水で洗浄して残留物を洗し１流した。さらに、
腸管をひつくり返し粘液をペーパータオルで拭き取った
後、粘膜細胞をスライドグラスで擦取した。擦取した粘
膜細胞に１匹当りｌθ〜２０１の５０１１ＩＭマンニト
ールー２ｍＭ トリス／塩酸緩衝液（ｐＨ７，１）を加
え、テフロンホモジナイザーで５ストロークのホモジネ
ーシジンを行なフた。ホモジネートに粉末ＣａＣｌ２を
ｌ０ｍＭになるように加え、ときどき軽くかきまぜた。(1) Adjustment of the jejunum border All operations below were performed at 0 to 4°C. 200g+f
Immediately after death, the jejunum was removed from the rat, and the inside of the tube was washed with physiological saline to remove any residue. moreover,
After turning the intestinal tract over and wiping the mucus with a paper towel, mucosal cells were scraped off with a glass slide. 5011IM mannitol-2mM Tris/hydrochloric acid buffer (pH 7.1) was added to the scraped mucosal cells per mouse, and homogenized for 5 strokes using a Teflon homogenizer. Powdered CaCl2 was added to the homogenate to a concentration of 10 mM, and the mixture was stirred gently from time to time.
１５分後に、３０００Ｘｇ、１５分間遠心し、さらに、
その上清を２７０００Ｘｇ、３０分間遠心した。この沈
澱を５０ｍＭマンニトール−１０ｍＭへバス／トリス緩
衝液（ｐ１１７．５）に懸濁し、テフロンホモジナイザ
ーでホモジナイズした。ホモジネートをさらに、２７０
００Ｘｇ、３０分間遠心した後、沈澱を１００ｍＭマン
ニトール−１０ＩＩＩＭトリス／へベス（ｐＨ７，５）
に懸濁しく２〜３ｍｇ ｐｒｏｔｅｉｎ／ ｍｕ）、刷
子縁膜小胞体を調製した。After 15 minutes, centrifuge at 3000Xg for 15 minutes, and
The supernatant was centrifuged at 27,000×g for 30 minutes. This precipitate was suspended in 50 mM mannitol-10 mM Bath/Tris buffer (p117.5) and homogenized with a Teflon homogenizer. Add the homogenate to 270
After centrifugation at 00Xg for 30 minutes, the precipitate was diluted with 100mM mannitol-10IIIM Tris/Heves (pH 7.5).
Brush border membrane endoplasmic reticulum was prepared by suspending 2 to 3 mg protein/mu).
（２）グルコース輸送阻害活性の測定
刷子縁膜小胞体懸濁液を２０μｍ試験管に取り、１００
ｍＭマンニトール−１０＋ｎＭトリス／へベス（ｐＨ７
゜５）に溶解した各濃度の試料を１０μに加え、２０℃
で３分間ブレインキュベートした。これに２０μにの２
ｍＭ Ｄ−［”Ｃ１−ｇｌｕｃｏｓｅ（１０μ（：ｉ／
ｍｌ）−１００ｍＭＮａｓｃＮ−１００１Ｍマンニトー
ル−１０ｍＭトリス／ヘベス（ｐＨ７，５）を加え、２
０℃で１５秒間インキュベートした後、水冷した反応停
止１−液（１５０ｍＭＮａＣＩ−０，２ｍＭフロリジン
−１ｍＭトリス／塩酸、 ｐＨ７，５）を１ｍｊ！加え
、直ちにメンプレーンフィルター（ポアサイズ；０．２
μｍ）で濾過した。さらに、上記反応停＋Ｌ ＊ ４ｒ
ｎ ｆｌで洗浄した後、メンブレーンフィルター−Ｆに
トラップされた膜小廁体の放射活性をフィルターごと測
定した。(2) Measurement of glucose transport inhibitory activity Take the brush border membrane endoplasmic reticulum suspension in a 20 μm test tube,
mM Mannitol-10 + nM Tris/Heves (pH 7)
Add the sample of each concentration dissolved in ゜5) to 10μ,
The mixture was incubated for 3 minutes. Add to this 2 to 20μ
mM D-[”C1-glucose (10μ(:i/
ml)-100mM NascN-1001M mannitol-10mM Tris/Heves (pH 7,5) was added, 2
After incubating for 15 seconds at 0°C, add 1 mj of water-cooled reaction stop solution (150mM NaCI-0, 2mM phlorizin-1mM Tris/HCl, pH 7,5). Immediately filter the membrane filter (pore size: 0.2
μm). Furthermore, the above reaction stop +L * 4r
After washing with nfl, the radioactivity of the membrane particles trapped in Membrane Filter-F was measured for each filter.
阻害活性は、以下の式により算出した。Inhibitory activity was calculated using the following formula.
バックグラウンド：刷子縁膜小胞体懸濁液を試料を含ま
ないに１衝液とブレインキュベートし、反応停ｒｔ−液
を加えたあと放射性グルコースを加えインキュベートし
たときの放射活性。Background: Radioactivity when the brush border membrane endoplasmic reticulum suspension was incubated with a solution containing no sample, rt-solution was added to stop the reaction, and then radioactive glucose was added and incubated.
対照群放射活性：刷７−縁１模小ＪＵ体懸濁液を試料を
含まないＭｆｔｌ液とブレインキュベートしたあと、放
射性グルコースを加えインキュベートしたときの放射活
性。Control group radioactivity: Radioactivity obtained when a small JU body suspension was incubated with a sample-free Mftl solution and then radioactive glucose was added and incubated.
試験群放射活性；刷子縁膜小胞体懸濁液を試料を含む緩
衝液とブレインキュベートしあと、放射性グルコースを
加えインキュベートしたときの放射活性。Test group radioactivity: Radioactivity obtained when the brush border membrane endoplasmic reticulum suspension was incubated with a buffer solution containing the sample, and then radioactive glucose was added and incubated.
：ｊＳｆ表
一１１活性
活性炭カラム溶出画分のグルコース輸送用第１表および
第２表かられかるように、本発明において必須成分とし
て用いられるフェニルグルコシド化合物の阻害活性は高
く、体内における糖類の吸収を抑制する効果が充分に得
られるものである。:jSf Table 11 Activated carbon column elution fraction for glucose transport As shown in Tables 1 and 2, the phenyl glucoside compound used as an essential component in the present invention has a high inhibitory activity, and has a high inhibitory activity on the absorption of sugars in the body. The effect of suppressing this can be sufficiently obtained.
第１図は非蔗糖画分の活性炭カラムクロマトグラフ、第
２図は活性炭カラム溶出画分のＴＬＣをあられす。
※Ｃ度はすべて５ｓｇ／ −Ｑ 、 ｎ〜ゴ特許出顧人
万［Ｉ発酵株式会社Figure 1 shows the activated carbon column chromatography of the non-sucrose fraction, and Figure 2 shows the TLC of the activated carbon column elution fraction. *All C degrees are 5sg/-Q, n~go Patent Supplier: Man [I Fermentation Co., Ltd.
Claims (2)
フェニルグルコシド化合物を必須成分とする糖類吸収抑
制剤。(1) A sugar absorption inhibitor whose essential component is a phenyl glucoside compound obtained by extraction from unrefined sugars such as raw sugar and molasses.
前記フェニルグルコシド化合物がタキオサイド（（３−
メトキシ−４−ヒドロキシフェニル）−β−Ｄ−グルコ
ピラノシド）及びアルブチン（４ヒドロキシフェニル−
β−Ｄ−グルコピラノシド）であることを特徴とする特
許請求の範囲第１項記載の糖類吸収抑制剤。(2) The phenyl glucoside compound obtained by extraction from unrefined sugars such as raw sugar and molasses is tachyoside ((3-
methoxy-4-hydroxyphenyl)-β-D-glucopyranoside) and arbutin (4-hydroxyphenyl-
The saccharide absorption inhibitor according to claim 1, characterized in that the saccharide absorption inhibitor is β-D-glucopyranoside.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1285759A JP2816725B2 (en) | 1989-10-31 | 1989-10-31 | Sugar absorption inhibitor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1285759A JP2816725B2 (en) | 1989-10-31 | 1989-10-31 | Sugar absorption inhibitor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH03145424A true JPH03145424A (en) | 1991-06-20 |
| JP2816725B2 JP2816725B2 (en) | 1998-10-27 |
Family
ID=17695686
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1285759A Expired - Fee Related JP2816725B2 (en) | 1989-10-31 | 1989-10-31 | Sugar absorption inhibitor |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2816725B2 (en) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4884319A (en) * | 1987-10-12 | 1989-12-05 | Hergeth Hollingsworth, Gmbh | Apparatus for arresting the rotary tower of a bale opening device |
| EP1781116A1 (en) * | 2004-06-04 | 2007-05-09 | Horizon Science Pty. Ltd. | Natural sweetener |
| KR100799655B1 (en) * | 2006-09-04 | 2008-01-30 | 인제대학교 산학협력단 | Composition comprising an extract of phyllostachys bambusoides sieb. et zucc. and a gmhb compound isolated from the extract thereof showing anti-oxidative activity |
| EP2064352A1 (en) | 2006-09-19 | 2009-06-03 | Horizon Science Pty Ltd | Extracts derived from sugar cane and a process for their manufacture |
| WO2011081488A2 (en) * | 2009-12-30 | 2011-07-07 | Lee Hai Soo | Composition for treatment of obesity using wheat bran extract or active ingredient isolated therefrom |
| KR101231583B1 (en) * | 2010-08-11 | 2013-02-08 | 이해수 | Composition for Improving Obesity Using Effective Compounds Isolated from Wheat Bran |
| US8697145B2 (en) | 2005-06-03 | 2014-04-15 | Horizon Science Pty. Ltd. | Substances having body mass redistribution properties |
| US9572852B2 (en) | 2011-02-08 | 2017-02-21 | The Product Makers (Australia) Pty Ltd | Sugar extracts |
| US10350259B2 (en) | 2013-08-16 | 2019-07-16 | The Product Makers (Australia) Pty Ltd | Sugar cane derived extracts and methods of treatment |
| US11730178B2 (en) | 2012-08-28 | 2023-08-22 | Poly Gain Pte Ltd | Extraction method |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2022246313A1 (en) * | 2021-05-21 | 2022-11-24 | The Coca-Cola Company | Sweetness enhancement and taste modulation with digupigan a analogs |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59203452A (en) * | 1983-05-02 | 1984-11-17 | Osaka Chem Lab | Food containing specific oligosaccharide |
| JPS6169727A (en) * | 1984-09-14 | 1986-04-10 | Osaka Chem Lab | Saccharide absorption inhibitor and food containing same |
-
1989
- 1989-10-31 JP JP1285759A patent/JP2816725B2/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59203452A (en) * | 1983-05-02 | 1984-11-17 | Osaka Chem Lab | Food containing specific oligosaccharide |
| JPS6169727A (en) * | 1984-09-14 | 1986-04-10 | Osaka Chem Lab | Saccharide absorption inhibitor and food containing same |
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4884319A (en) * | 1987-10-12 | 1989-12-05 | Hergeth Hollingsworth, Gmbh | Apparatus for arresting the rotary tower of a bale opening device |
| US8138162B2 (en) | 2004-06-04 | 2012-03-20 | Horizon Science Pty Ltd. | Natural sweetener |
| EP1781116A1 (en) * | 2004-06-04 | 2007-05-09 | Horizon Science Pty. Ltd. | Natural sweetener |
| EP1781116A4 (en) * | 2004-06-04 | 2009-07-29 | Horizon Science Pty Ltd | Natural sweetener |
| US9161562B2 (en) | 2004-06-04 | 2015-10-20 | Horizon Science Pty Ltd | Natural sweetener |
| US8697145B2 (en) | 2005-06-03 | 2014-04-15 | Horizon Science Pty. Ltd. | Substances having body mass redistribution properties |
| KR100799655B1 (en) * | 2006-09-04 | 2008-01-30 | 인제대학교 산학협력단 | Composition comprising an extract of phyllostachys bambusoides sieb. et zucc. and a gmhb compound isolated from the extract thereof showing anti-oxidative activity |
| US9364016B2 (en) | 2006-09-19 | 2016-06-14 | The Product Makers (Australia) Pty Ltd | Extracts derived from sugar cane and a process for their manufacture |
| EP2064352A1 (en) | 2006-09-19 | 2009-06-03 | Horizon Science Pty Ltd | Extracts derived from sugar cane and a process for their manufacture |
| CN102686227A (en) * | 2009-12-30 | 2012-09-19 | 李海寿 | Composition for treatment of obesity using wheat bran extract or active ingredient isolated therefrom |
| WO2011081488A3 (en) * | 2009-12-30 | 2011-12-01 | Lee Hai Soo | Composition for treatment of obesity using wheat bran extract or active ingredient isolated therefrom |
| WO2011081488A2 (en) * | 2009-12-30 | 2011-07-07 | Lee Hai Soo | Composition for treatment of obesity using wheat bran extract or active ingredient isolated therefrom |
| KR101231583B1 (en) * | 2010-08-11 | 2013-02-08 | 이해수 | Composition for Improving Obesity Using Effective Compounds Isolated from Wheat Bran |
| US9572852B2 (en) | 2011-02-08 | 2017-02-21 | The Product Makers (Australia) Pty Ltd | Sugar extracts |
| US9717771B2 (en) | 2011-02-08 | 2017-08-01 | The Product Makers (Australia) Pty Ltd | Sugar extract |
| US10226502B2 (en) | 2011-02-08 | 2019-03-12 | The Product Makers (Australia) Pty Ltd | Sugar extract |
| US11730178B2 (en) | 2012-08-28 | 2023-08-22 | Poly Gain Pte Ltd | Extraction method |
| US10350259B2 (en) | 2013-08-16 | 2019-07-16 | The Product Makers (Australia) Pty Ltd | Sugar cane derived extracts and methods of treatment |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2816725B2 (en) | 1998-10-27 |
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