JP2010527905A - コエンザイムq−10およびジヒドロリポ酸を含有する組成物 - Google Patents
コエンザイムq−10およびジヒドロリポ酸を含有する組成物 Download PDFInfo
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- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 1
- 150000008104 phosphatidylethanolamines Chemical class 0.000 description 1
- 150000003905 phosphatidylinositols Chemical class 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
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- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
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- LCAZOMIGFDQMNC-FORWCCJISA-N rosmanol Chemical compound C1CCC(C)(C)[C@@H]2[C@H]3[C@@H](O)C(C=C(C(=C4O)O)C(C)C)=C4[C@]21C(=O)O3 LCAZOMIGFDQMNC-FORWCCJISA-N 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
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- 235000014102 seafood Nutrition 0.000 description 1
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- 235000013874 shellac Nutrition 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
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- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
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- 239000010677 tea tree oil Substances 0.000 description 1
- 229940111630 tea tree oil Drugs 0.000 description 1
- 238000012360 testing method 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
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- AOBORMOPSGHCAX-DGHZZKTQSA-N tocofersolan Chemical compound OCCOC(=O)CCC(=O)OC1=C(C)C(C)=C2O[C@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C AOBORMOPSGHCAX-DGHZZKTQSA-N 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
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- 239000003860 topical agent Substances 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
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- 239000011701 zinc Substances 0.000 description 1
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- 239000002076 α-tocopherol Substances 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
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 1
Classifications
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
- A61K31/05—Phenols
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/075—Ethers or acetals
- A61K31/085—Ethers or acetals having an ether linkage to aromatic ring nuclear carbon
- A61K31/09—Ethers or acetals having an ether linkage to aromatic ring nuclear carbon having two or more such linkages
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- A61K31/12—Ketones
- A61K31/122—Ketones having the oxygen directly attached to a ring, e.g. quinones, vitamin K1, anthralin
-
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- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
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- A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
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Abstract
Description
組成物が8%の水を含有するエタノール溶液を含まないという条件で、CoQ−10を、95重量%を越えてCoQ−10の還元型に還元するのに十分な量のジヒドロリポ酸(DHLA)を含む還元型コエンザイムQ−10(CoQ−10)組成物を提供する。
還元型コエンザイムQ−10(CoQ−10)組成物を被包するソフトゼラチンカプセルと
を含む還元型コエンザイムQ−10(CoQ−10)組成物を被包するソフトゼラチンカプセル剤。
CoQ−10を、95重量%を越えてCoQ−10の還元型に還元するのに十分な量のジヒドロリポ酸(DHLA)と、
還元型コエンザイムQ−10(CoQ−10)組成物を被包するソフトゼラチンカプセルとからなる、還元型コエンザイムQ−10(CoQ−10)組成物を被包するソフトゼラチンカプセル剤。
7.1g(34.1mmol)のDHLAに、1.1g(1.27mmol)のCoQ−10(酸化型の)を加えた。この混合物を、均一な溶液が達成されるまで撹拌した。この溶液を25℃で1週間維持し、その後、HPLC分析(210nmでのUV検出器)を実施した。混合物中のCoQ10の酸化型(ユビキノン)とCoQ10の還元型(ユビキノールの形)の割合は、1:5〜98.5であった。溶液のpH値は約3.80であった(Metrohm827pH Labによって測定した)。
40mlのTHFに、3g(3.48mmol)のCoQ−10(酸化型)を溶解し、0.32g(8.65mmol)のNaBH4を加えた。この溶液を、30℃で1時間維持した。HPLC分析(210nmでのUV検出器)下では、CoQ−10の酸化型(ユビキノン)は溶液中に検出されなかった。
種々の温度で、DHLAにコエンザイムQ10を溶解した。図1は、種々の温度でのCoQ−10の溶解度を示す。縦座標は、DHLA中の溶解したCoQ−10のパーセンテージを示す。
11.09g(53.3mmol)のDHLAに、0.9g(1.04mmol)のCoQ−10(酸化型)を加えた。この混合物を、均一な溶液が達成されるまで撹拌した。この溶液を25℃で1週間維持し、その後、HPLC分析(210nmでのUV検出器)を実施した。混合物中のCoQ10の酸化型(ユビキノン)とCoQ10の還元型(ユビキノールの形)の割合は、1:5〜98.5であった。溶液のpH値は約3.80〜3.90であった。
分析法
機器および材料:
HPLC:717プラスオートサンプラーおよび2996PDA検出器を備えたWaters600ポンプ
天秤:Sartorius BP 211D
試薬:アセトニトリル(HPLC等級、Fisher)、蒸留水(Nestle)、メタノール(Fisher、HPLC等級)
LAおよびDHLA:
移動相:0.03% H3PO4:アセトニトリル=60:40
カラム:Agilent ellipse XDB−C18(150mm*4.6mm、5μm□
温度:30℃
UV検出:220nm
注入容量:10μl
流速:1.0ml/分
移動相:メタノール:エタノール=75:25
カラム:Waters Symmetry C18(150mm*4.6mm、5μm)
温度:30℃
UV検出:210nm
注入容量:2μl
流速:1.0ml/分
材料および処理:
5匹の雄のスプラーグ−ドーリーラット(体重220〜250g、7〜8週齢)を、各処理群に使用してよい。処理群は、3群を含む。群Aは、DHLAとともにコエンザイムQ10を用いるものであり;群Bは、アスコルビルパルミチン酸塩とともにコエンザイムQ10を用いるものであり;群Cは、コエンザイムQ10のみを用いるものである。ラットには、コエンザイムQ10サンプルを経口投与し、コエンザイムQ10投与量は、20mg/Kgとする。
コエンザイムQ10およびアスコルビルパルミチン酸塩は、コエンザイムQ10/アスコルビルパルミチン酸塩=l/4、w/w、を用いて調製し、適した乳化剤、例えば、Tweenを用いて乳化する;
コエンザイムQ10は、その他の機能性物質を含まない、コエンザイムQ10の還元型である。
血液サンプリング(0.5mL)は、投与(t=0)、および投与の10、20、30、40、50、60、90,120、150、180、240分後に行う。
単回経口投与後の、時間に対するサンプルの平均還元型コエンザイムQ10血漿濃度を比較する。
結果は、群Aの還元型コエンザイムQ10血漿濃度は、群Bのものよりも数倍高く、群CのコエンザイムQ10血漿濃度は極めて低いというものであるはずである。
コエンザイムQ10の経口投与を受けたラットから得られたデータは、DHLAととものコエンザイムQ10は、最高に吸収され、還元型Q10を最高に保護し、ならびにin vivoで還元型コエンザイムQ10を最高に保持したということを明らかにすることができる。
Claims (20)
- 還元型コエンザイムQ−10(CoQ−10)組成物であって、組成物が8%の水を含有するエタノール溶液を含まないという条件で、CoQ−10を、95重量%を越えてCoQ−10の還元型に還元するのに十分な量のジヒドロリポ酸(DHLA)を含む組成物。
- さらに、担体を含む、請求項1に記載の組成物。
- 担体がDHLAである、請求項2に記載の組成物。
- 担体が、植物油、魚油またはそれらの組み合わせである、請求項2に記載の組成物。
- さらに、抗酸化剤または抗酸化酵素を含む、請求項1に記載の組成物。
- 抗酸化剤が、ビタミンE、ビタミンE誘導体、ビタミンC、ビタミンC誘導体、プロブコール、リコピン、ビタミンA、カロテノイド、ビタミンB、ビタミンB1、ビタミンB誘導体、フラボノイド、ポリフェノール、グルタチオン、ピロロキノリンキノン、ピクノジェノール、フラバンジェノール、セレン、リポ酸、リポ酸誘導体、L−カルニチンまたはそれらの混合物である、請求項5に記載の組成物。
- 抗酸化酵素が、スーパーオキシドジムスターゼ、グルタチオンペルオキシダーゼ、グルタチオン−S−トランスフェラーゼ、グルタチオンレダクターゼ、カタラーゼおよびアスコルビン酸ペルオキシダーゼまたはそれらの混合物である、請求項5に記載の組成物。
- ソフトゼラチンカプセル内に被包されている、請求項1に記載の組成物。
- 還元型コエンザイムQ−10(CoQ−10)組成物であって、CoQ−10を、95重量%を越えてCoQ−10の還元型に還元するのに十分な量のジヒドロリポ酸(DHLA)から本質的になる組成物。
- 8%の水を含有するエタノール溶液を含まない、請求項9に記載の組成物。
- さらに、担体を含む、請求項9に記載の組成物。
- 担体がDHLAである、請求項11に記載の組成物。
- 担体が、植物油、魚油またはそれらの組み合わせである、請求項11に記載の組成物。
- さらに、抗酸化剤または抗酸化酵素を含む、請求項9に記載の組成物。
- 抗酸化剤が、ビタミンE、ビタミンE誘導体、ビタミンC、ビタミンC誘導体、プロブコール、リコピン、ビタミンA、カロテノイド、ビタミンB、ビタミンB誘導体、フラボノイド、ポリフェノール、グルタチオン、ピロロキノリンキノン、ピクノジェノール、フラバンジェノール、セレン、リポ酸、リポ酸誘導体またはそれらの混合物である、請求項14に記載の組成物。
- 抗酸化酵素が、スーパーオキシドジムスターゼ、グルタチオンペルオキシダーゼ、グルタチオン−S−トランスフェラーゼ、グルタチオンレダクターゼ、カタラーゼおよびアスコルビン酸ペルオキシダーゼまたはそれらの混合物である、請求項14に記載の組成物。
- ソフトゼラチンカプセル内に被包されている、請求項9に記載の組成物。
- 還元型コエンザイムQ−10溶液を調製する方法であって、
コエンザイムQ−10(CoQ−10)を、十分な量のジヒドロリポ酸(DHLA)と接触させて、CoQ−10を、95重量%を越えてCoQ−10の還元型に還元するステップを含む方法。 - 歯周病、ミトコンドリア関連疾患および障害、パーキンソン病、プラター−ウィリー(Prater−Willey)症候群、片頭痛または頭痛を治療する方法であって、それを必要とする個体に、有効量の請求項1に記載の組成物を投与するステップを含む方法。
- 歯周病、ミトコンドリア関連疾患および障害、パーキンソン病、プラター−ウィリー(Prater−Willey)症候群、片頭痛または頭痛を治療する方法であって、それを必要とする個体に、有効量の請求項9に記載の組成物を投与するステップを含む方法。
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AT14222006A AT504148A1 (de) | 2006-08-25 | 2006-08-25 | Coenzym q10 enthaltende zusammensetzung |
US88639507P | 2007-01-24 | 2007-01-24 | |
US11/843,935 US8642030B2 (en) | 2006-08-25 | 2007-08-23 | Compositions containing coenzyme Q-10 and dihydrolipoic acid |
PCT/IB2007/003623 WO2008023277A2 (en) | 2006-08-25 | 2007-08-24 | Compositions containing coenzyme q-10 and dihydrolipoic acid |
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US (2) | US8642030B2 (ja) |
EP (1) | EP2073793A2 (ja) |
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WO (1) | WO2008023277A2 (ja) |
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WO2014188861A1 (ja) * | 2013-05-20 | 2014-11-27 | ユーハ味覚糖株式会社 | ユビキノール高含有ゲル状組成物 |
JP2014226050A (ja) * | 2013-05-20 | 2014-12-08 | ユーハ味覚糖株式会社 | 還元型コエンザイムq10含有グミキャンディの製造方法および該製造方法を用いて得られるグミキャンディ |
JP2015104342A (ja) * | 2013-11-29 | 2015-06-08 | ユーハ味覚糖株式会社 | ユビキノール高含有ゲル状組成物 |
JP2015105243A (ja) * | 2013-11-29 | 2015-06-08 | ユーハ味覚糖株式会社 | ユビキノール含有液状組成物 |
JP2015209398A (ja) * | 2014-04-25 | 2015-11-24 | ユーハ味覚糖株式会社 | 高吸収型ユビキノール製剤 |
WO2020085155A1 (ja) * | 2018-10-26 | 2020-04-30 | サントリーホールディングス株式会社 | 還元型コエンザイムq10を含む経口用組成物、その製造方法、変色抑制方法及び変色抑制剤 |
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CN103052391B (zh) * | 2010-08-09 | 2015-04-29 | 三菱瓦斯化学株式会社 | 吡咯并喹啉醌的凝胶 |
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US20140147498A1 (en) | 2014-05-29 |
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