JP5637865B2 - 1,5−ag含有組成物 - Google Patents
1,5−ag含有組成物 Download PDFInfo
- Publication number
- JP5637865B2 JP5637865B2 JP2010546673A JP2010546673A JP5637865B2 JP 5637865 B2 JP5637865 B2 JP 5637865B2 JP 2010546673 A JP2010546673 A JP 2010546673A JP 2010546673 A JP2010546673 A JP 2010546673A JP 5637865 B2 JP5637865 B2 JP 5637865B2
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- JP
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- Prior art keywords
- blood
- postprandial
- anhydroglucitol
- group
- hydrogen atoms
- Prior art date
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- 150000003214 pyranose derivatives Chemical class 0.000 description 1
- RADKZDMFGJYCBB-UHFFFAOYSA-N pyridoxal hydrochloride Natural products CC1=NC=C(CO)C(C=O)=C1O RADKZDMFGJYCBB-UHFFFAOYSA-N 0.000 description 1
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- HEBKCHPVOIAQTA-ZXFHETKHSA-N ribitol Chemical compound OC[C@H](O)[C@H](O)[C@H](O)CO HEBKCHPVOIAQTA-ZXFHETKHSA-N 0.000 description 1
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- 238000012360 testing method Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 235000019157 thiamine Nutrition 0.000 description 1
- KYMBYSLLVAOCFI-UHFFFAOYSA-N thiamine Chemical compound CC1=C(CCO)SCN1CC1=CN=C(C)N=C1N KYMBYSLLVAOCFI-UHFFFAOYSA-N 0.000 description 1
- 239000011721 thiamine Substances 0.000 description 1
- DPJRMOMPQZCRJU-UHFFFAOYSA-M thiamine hydrochloride Chemical compound Cl.[Cl-].CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N DPJRMOMPQZCRJU-UHFFFAOYSA-M 0.000 description 1
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- 239000004474 valine Substances 0.000 description 1
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- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
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- 235000019160 vitamin B3 Nutrition 0.000 description 1
- 239000011708 vitamin B3 Substances 0.000 description 1
- 235000021470 vitamin B5 (pantothenic acid) Nutrition 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/30—Artificial sweetening agents
- A23L27/33—Artificial sweetening agents containing sugars or derivatives
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/30—Artificial sweetening agents
- A23L27/33—Artificial sweetening agents containing sugars or derivatives
- A23L27/34—Sugar alcohols
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Description
〔1〕 1,5-D-アンヒドログルシトール、1,5-D-アンヒドロフルクトース及び式(I)で表される化合物からなる群より選ばれる少なくとも1つを含有してなる食後高脂血症改善用組成物であって、食事による血中中性脂肪の上昇を摂取後、少なくとも4時間にわたって抑制する食後高脂血症改善用の組成物(但し、食品を除く)、
〔2〕 食事による血中中性脂肪の上昇を摂取後、少なくとも4時間にわたって抑制する食後高脂血症の予防剤及び/又は改善剤(但し、食品を除く)の製造のための、1,5-D-アンヒドログルシトール、1,5-D-アンヒドロフルクトース及び式(I)で表される化合物からなる群より選ばれる少なくとも1つの使用、
〔3〕 1,5-D-アンヒドログルシトール、1,5-D-アンヒドロフルクトース及び式(I)で表される化合物からなる群より選ばれる少なくとも1つからなる、食事による血中中性脂肪の上昇を摂取後、少なくとも4時間にわたって抑制する食後血中中性脂肪上昇抑制剤(但し、食品を除く)、ならびに
〔4〕 1,5-D-アンヒドログルシトール、1,5-D-アンヒドロフルクトース及び式(I)で表される化合物からなる群より選ばれる少なくとも1つからなる、食事による脂肪吸収を摂取後、少なくとも4時間にわたって抑制する脂肪吸収抑制剤(但し、食品を除く)
に関する。
で表わされる1,5-AGの誘導体が好適例として挙げられる。
1,5-D-アンヒドログルシトールとオクタン酸ビニルを基質として有機溶媒中リパーゼ(NOVOZYM435)を作用させることで、1,5−アンヒドログルシトール-6-O-オクタン酸エステル(1,5-AG-Octanoate)を収率90%で合成した。
1,5-D-アンヒドログルシトールとパルミチン酸ビニルを基質として有機溶媒中リパーゼ(NOVOZYM435)を作用させることで、1,5−アンヒドログルシトール-6-O-パルミチン酸エステル(1,5-AG-Palmitate)を収率92%で合成した。
D-グルコースを原料として、J. Chem. Soc., 214 (1956)に記載の方法に従って、1,5−アンヒドログルシトール-2,3,4,6-O-テトラアセテートを収率90%で合成した。
D-グルコースを原料として、J. Chem. Soc., 214 (1956)に記載の方法に従って、1,5−アンヒドログルシトール-2,3,4,6-O-テトララウレートを収率70%で合成した。以下に、NMR(1H、13C)、IR、旋光度、MS、融点測定による構造確認の結果を示す。
1H-NMR(DMSO-d6, 300MHz)δ:0.83-0.88(m,12H), 1.18-1.31(m,66H), 1.46-1.54(m,8H), 2.18(t,8H,J=7.3Hz), 2.49-2.52(m,8H)
13C-NMR(DMSO-d6, 300MHz)δ:174.4, 33.6, 31.3, 29.0, 28.9, 28.7, 28.6, 28.5, 24.5, 22.1, 13.9
IR(KBr): 3749, 3672, 3614, 1701, 1469, 1431, 1350, 1305, 1246cm-1
〔α〕D: +3.4°(CHCl3,C=1.0)
FAB-MS(m/z):measured mass 893.74225(M+1)+, calculated mass 893.74453(M+1)+
m.p: 44℃
イソマルトトリオースを原料として、J. Chem. Soc., 214 (1956)に記載の方法に従って、1-デオキシイソマルトトリオース-デカアセテートを収率91%で合成した。以下に、NMR(1H)、IR、旋光度、MS、融点測定による構造確認の結果を示す。
1H-NMR(CDCl3, 300MHz)δ:1.97-2.17(m,60H), 3.46-3.82(m,5H), 3.93-4.22(m,4H), 4.72-5.26(m,10H), 5.39-5.48(m,3H)
IR(KBr): 3024, 2951, 1755, 1435, 1373, 1223, 1165, 1038cm-1
〔α〕D: +142.9°(CHCl3,C=1.0)
FAB-MS(m/z):measured mass 909.28205(M+1)+, calculated mass 909.28763(M+1)+
m.p: 96℃
1,5-AG誘導体の合成例5と同様にして、1-デオキシイソマルトトリオース-デカアセテートを合成し、さらに、これをCan. J. Chem., 49, 493 (1971)に記載の方法に準じて脱アセチル化することで、1-デオキシ-イソマルトトリオースを収率53%で得た。以下に、NMR(1H、13C)、IR測定による構造確認の結果を示す。
1H-NMR(DMSO-d6, 300MHz)δ:2.89-4.85(m,19H), 4.24(br-s,1H), 4.63(br-s,2H)
13C-NMR(DMSO-d6, 300MHz)δ:102.4×2, 102.1, 98.7, 98.2, 97.0, 94.1, 76.8, 74.9, 73.3, 72.5, 72.1, 71.4, 70.6, 70.4, 70.2, 62.9, 60.9
IR(KBr): 3750-3300(br-s), 2920, 2850, 1597, 1458, 1419, 1362, 1153, 1022cm-1
リパーゼはブタすい臓由来(ナカライテスク社製)を用いた。200mMリン酸緩衝液(pH7.5)に酵素タンパク質を溶解して酵素溶液を調製した。次に、1,5−アンヒドログルシトール-6-O-オクタン酸エステル(合成例1)、及び1,5-アンヒドログルシトール-6-O-パルミチン酸エステル(合成例2)の各脂肪酸エステル水溶液(50mM)500μLに、前記酵素溶液200μLを加え、37℃でインキュベーションした。反応停止は沸騰水浴中で3分間加熱することで行い、生成した1,5-アンヒドログルシトール量(1,5-AG量)をHPLCにて定量した。結果を図1に示す。なお、脂肪酸エステルが全て分解された場合の1,5-AG量を100%とした。
リパーゼはブタすい臓由来(ナカライテスク社製)を用いた。200mMリン酸緩衝液(pH7.5)に酵素タンパク質を溶解して酵素溶液を調製した。次に、1,5−アンヒドログルシトール-2,3,4,6-O-テトラアセテート(合成例3)、及び1,5−アンヒドログルシトール-2,3,4,6-O-テトララウレート(合成例4)に、前記酵素溶液200μLを加え、37℃で180分インキュベーションした。反応停止は沸騰水浴中で3分間加熱することで行い、生成した1,5-アンヒドログルシトール量(1,5-AG量)をHPLCにて定量した。結果を表1に示す。なお、脂肪酸エステルが全て分解された場合の1,5-AG量を100%とした。
ラット小腸由来グリコシダーゼは、Kesslerらの方法でWistar系雄性ラット(10週齢、体重約290〜310g)の空腸から小腸刷子縁膜を調製し粗酵素とした(Kessler, M., Acuto, O., Storelli, C., Murer, H., Muller, M. and Semenza, G. (1978) A modifild procedure for the rapid preparation of efeiciently transporting vesicles From Small Intestinal Brush Border Membranes, Bio.Bio.Acta, 506, 136-154.)。
実施例2−1と同様にして得られたラット小腸由来グリコシダーゼ20μLに200mMリン酸緩衝液(pH6.8)50μLを加えて37℃で30分間プレインキュベーションした後、100mMの1-デオキシ-イソマルトトリオース(合成例6)50μLを加え37℃でインキュベーションした。反応は沸騰水浴中で3分間加熱することにより停止した。反応液中の遊離した1,5-AGをHPLC(カラム;HITACHI GL-C611)にて分析することにより定量した。結果を表3に示す。
実施例1−1と同様にして得られたブタすい臓由来リパーゼ(ナカライテスク社製)の酵素溶液100μL、及び実施例2−1と同様にして得られたラット小腸由来グリコシダーゼ100μLを100mMリン酸緩衝液(pH6.8)100μLに溶解させた。この酵素混合溶液200μLに1-デオキシ-イソマルトトリオース-デカアセテート(合成例5)を加えて37℃で180分間インキュベーションした。反応は沸騰水浴中で3分間加熱することにより停止した。反応液中の遊離した1,5-AGをHPLC(カラム;HITACHI GL-C611)にて分析することにより定量し、1,5-AGへの変換理論量を100%とした際の1,5-AGへの変換率(%)を算出した。結果を表4に示す。
一晩絶食させた7週齢のddy系雄性マウス(Japan SLC, Inc.より購入、平均体重30g)に、D-グルコース又は1,5-AGを含有する注射用水(大塚製薬社製)を、それぞれ2.5g/kg体重となるように胃ゾンテにて経口投与した(各群5匹)。投与後15、30、60及び120分に尾静脈から採血し、血糖値を測定した。血糖値の測定はアントセンスIII(バイエルメディカル社製)にて測定した。結果を図2に示す。
一晩絶食させた7週齢のddy系雄性マウス(Japan SLC, Inc.より購入、平均体重30g)に、D-グルコース又はD-グルコースと1,5-AGを含有する注射用水(大塚製薬社製)を、D-グルコース単独投与群には2.5g/kg体重、D-グルコースと1,5-AGの併用群1にはD-グルコース2.5g/kg体重、1,5-AG250mg/kg体重、併用群2にはD-グルコース2.5g/kg体重、1,5-AG500mg/kg体重となるように胃ゾンテにて経口投与した(各群5匹)。投与後15、30、60及び120分に尾静脈から採血し、血糖値を測定した。血糖値の測定は実施例1と同様にして行った。結果を図3に示す。なお、図中の「**」は、有意差(p<0.01)があることを示す。
一晩絶食させた12週齢のWistar系雄性ラット(Japan SLC, Inc.より購入、平均体重310g)に、脂肪乳剤〔イントラリピッド(登録商標)、大塚製薬社製〕のみを2.0g/kg体重となるように単独で、又は前記脂肪乳剤と1,5-AGを、脂肪乳剤2.0g/kg体重、1,5-AG500mg/kg体重となるように同時に、それぞれ胃ゾンテにて経口投与した(各群5匹)。投与後120、180、240及び300分に尾静脈から採血し、血中中性脂肪として、血中中性脂肪(血中トリグリセリド)濃度を測定した。血中トリグリセリド濃度の測定はトリグリセライドE-テストワコー(和光純薬工業社製)にて定量した。結果を図4に示す。なお、図中の「*」は、有意差(p<0.05)があることを示す。
1,5-AGを一回に投与しうる最大量と考えられる10g/kg体重をマウス(6週齢のddy系雄性マウス、Japan SLC, Inc.より購入)3匹に経口投与した。その結果、3匹すべて生存し、臓器、行動等に変化は認められなかった。
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