JP6368270B2 - モニエロサイドa及びその誘導体、又はそれを有効成分として含有する医薬用組成物、健康食品又は化粧品 - Google Patents
モニエロサイドa及びその誘導体、又はそれを有効成分として含有する医薬用組成物、健康食品又は化粧品 Download PDFInfo
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- JP6368270B2 JP6368270B2 JP2015075881A JP2015075881A JP6368270B2 JP 6368270 B2 JP6368270 B2 JP 6368270B2 JP 2015075881 A JP2015075881 A JP 2015075881A JP 2015075881 A JP2015075881 A JP 2015075881A JP 6368270 B2 JP6368270 B2 JP 6368270B2
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- monieroside
- derivatives
- food
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- monielloside
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- 159000000003 magnesium salts Chemical class 0.000 description 1
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
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- 239000003264 margarine Substances 0.000 description 1
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- 229910052751 metal Inorganic materials 0.000 description 1
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- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
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- 229940037525 nasal preparations Drugs 0.000 description 1
- 230000000324 neuroprotective effect Effects 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 230000000050 nutritive effect Effects 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
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- 229940021222 peritoneal dialysis isotonic solution Drugs 0.000 description 1
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- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
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- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
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- 102000004169 proteins and genes Human genes 0.000 description 1
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- 229940088594 vitamin Drugs 0.000 description 1
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Landscapes
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Saccharide Compounds (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
[1] 下記構造式(1)
[2] エステル化物が構造式(1)における1または2以上の水酸基がアシル化されていることを特徴とする[1]に記載の化合物。
[3] エーテル化物が構造式(1)における1または2以上の水酸基がエーテル化されていることを特徴とする[1]に記載の化合物。
[4] [1]乃至[3]のいずれかに記載の化合物を含有することを特徴とする疾病の予防又は治療用の医薬組成物。
[5] アセチルコリンエステラーゼ阻害剤であることを特徴とする[4]に記載の医薬組成物。
[6] 疾病がアルツハイマー病であることを特徴とする請求項4記載の医薬組成物。
[7] [1]乃至[3]のいずれかに記載の化合物を含有することを特徴とする食品添加物、サプリメント又は健康食品。
[8] 食欲調整剤である[7]に記載の食品添加物、サプリメント又は健康食品。
[9] [1]乃至[3]のいずれかに記載の化合物を含有することを特徴とする化粧品。
[10] AGEs(advanced glycation end products:以下、「終末糖化産物」ともいう。)生成抑制剤であることを特徴とする[9]に記載の化粧品。
このようにして、モニエロサイドAを取得することができるが、取得の確認は、例えば、旋光度、又は、MSスペクトルによって行なうことができる。
上記反応及び反応混合物からの上記エステル類又はエーテル類の取得は、自体公知の手段によって行なわれて良く、例えば、モニエロサイドAと上記ハロゲン化物とを反応させ、分配抽出、濃縮、クロマトグラフィ、結晶化、再結晶等から適宜に選択又は組み合わせて目的物質を取得することができる。
本発明は、モニエロサイドA及びその誘導体を含有する医薬を提供する。モニエロサイドAは、アセチルコリンエステラーゼ阻害活性を有するため、食欲調節用の医薬、或いは、アルツハイマー型痴呆症用の医薬として使用することができる。また、モニエロサイドAは、AGEs生成抑制作用を有するため、老化肌防御、改善用の内服剤又は外用剤等の医薬として使用することができる。
本発明は、モニエロサイドA及びその誘導体を含有する飲食品を提供する。本発明の飲食品はモニエロサイドAが、アセチルコリンエステラーゼ阻害活性を有するため食欲調節用飲食品として好適であり、またモニエロサイドAが、AGEs生成抑制作用を有するため、老化肌防御、改善用飲食品として好適であり、飲食品には、健康食品、機能性食品、特定保健用食品、病者用食品が含まれる。飲食品の形態は特に限定されない。例えば茶飲料、清涼飲料、炭酸飲料、栄養飲料、果実飲料、乳酸飲料等の飲料、そば、うどん、中華麺、即席麺等の麺類、飴、キャンディー、ガム、チョコレート、スナック菓子、ビスケット、ゼリー、ジャム、クリーム、焼き菓子、パン等の菓子およびパン類、かまぼこ、ハム、ソーセージ等の水産・畜産加工食品、加工乳、発酵乳等の乳製品、サラダ油、てんぷら油、マーガリン、マヨネーズ、ショートニング、ホイップクリーム、ドレッシング等の油脂および油脂加工食品、ソース、たれ等の調味料、カレー、シチュー、丼、お粥、雑炊等のレトルトパウチ食品、アイスクリーム、シャーベット、かき氷等の冷菓などを挙げることができる。
インド産オトメアゼナ (Bacopa monniera) の乾燥した全草(2.0kg)をメタノールで熱時(80℃)抽出した。抽出液を濾過し、残渣にメタノールを加え、同様の抽出操作を3回行った。メタノール抽出液を合わせて減圧下溶媒留去し、メタノール抽出エキス(608.82g、収率30.4%)を得た。
そこで、酢酸エチル画分を順相シリカゲル、逆相ODSカラムクロマトグラフィー及び逆相HPLCで繰り返し分離精製し、その結果、新規化合物モニエロサイドA(Monieroside A)を得た.
なお、これらの化合物は,1H−NMR及び13C−NMRスペクトルデータ、旋光度及びMSスペクトルにより同定した。
モニエロサイドAは負の旋光性([α]D 27 ‐3.9°、メタノール)を示す非結晶性粉末として得られた。IRスペクトルから水酸基(3415cm−1)、エステル(1705cm−1)及び芳香族(1609cm−1)の存在が示唆された。さらにpositive-ion FAB−MSにおいて擬似分子イオンピークがm/z 473 (M + Na)+ に観測され、高分解能FAB−MSから分子式C21H22O11を有する化合物であることが判明した。
以上の結果から、モニエロサイドAの上記化学構造[構造式(1)]を決定した。
アセチルコリンエステラーゼ阻害剤は、一般的にアルツハイマー症状に対する対症薬として用いられているが、中枢におけるコリンエステラーゼ阻害薬の主な副作用として、食欲不振、吐き気、嘔吐など消化器系の症状が共通しており、食欲の抑制傾向に働くことが一般的に知られている、一方、消化管付近では、分泌の少なくなったアセチルコリンの分泌を促進させ、消化管運動を亢進させることにより、食欲不振を改善する薬剤も知られており、アセチルコリン量を調節することにより、患者の容態によって食欲を調節できると考えられる。
近年、「抗老化」を目的とした新たな化粧品原料の開発が行われており、特に、タンパク質の糖化反応の反応生成物であるAGEsが老化に関与する物質として注目されており、この生成反応を抑える物質の探索が広くおこなわれている。今回、オトメアゼナのエキスおよび新規成分モニエロサイドAのAGEs生成抑制作用について検討を試みた。具体的な実験手順は、以下の通りである。
Claims (1)
- 下記構造式(1)
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DE19654635C1 (de) * | 1996-12-28 | 1998-01-08 | Singh Verma Shyam B | Kosmetische Zubereitungen enthaltend Extrakte von Phyllanthus emblica und Centella asiatica |
CN1249051C (zh) * | 2000-04-28 | 2006-04-05 | 阿卡蒂亚药品公司 | 毒蕈碱性激动剂 |
US7585523B2 (en) * | 2002-08-27 | 2009-09-08 | Targeted Medical Pharma | Composition and method to augment and sustain neurotransmitter production |
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