JP5258571B2 - クルクマロンガ抽出物からテトラヒドロキシクルクミン濃縮フラクションおよびテトラヒドロテトラヒドロキシクルクミン濃縮フラクションを製造するプロセス - Google Patents
クルクマロンガ抽出物からテトラヒドロキシクルクミン濃縮フラクションおよびテトラヒドロテトラヒドロキシクルクミン濃縮フラクションを製造するプロセス Download PDFInfo
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- A—HUMAN NECESSITIES
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- A61K31/12—Ketones
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- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
- A01N65/40—Liliopsida [monocotyledons]
- A01N65/48—Zingiberaceae [Ginger family], e.g. ginger or galangal
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/88—Liliopsida (monocotyledons)
- A61K36/906—Zingiberaceae (Ginger family)
- A61K36/9066—Curcuma, e.g. common turmeric, East Indian arrowroot or mango ginger
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/79—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
Description
TC =78.40
DC =4.11
DMDC =11.52
BDC =0.86
合計 =94.89%
TC =75.68
DC =6.32
DMDC =11.24
BDC =1.1
合計 =95.31%
DC[1-(3,4-ジヒドロキシフェニル)-7-(3-メトキシ-4-ヒドロキシフェニル)-1,6-ヘプタジエン-3,5-ジオン]。黄色粉末、mp164-166℃;IR(KBr):3484、1621、1267、1132、1140、964cm-1、1HNMR(DMSO-d6)δ3.82(3H、s、Ar-OCH3)、6.04(1H,s、H-4)、6.53(1H、d、J=16.0Hz、H-2またはH-6)、6.74(1H、d、J=16.0Hz、H-2またはH-6)、6.76(1H、d、J=8.5Hz、H-5’)、6.80(1H、d、J=8.3Hz、H-5”)、7.07(1H、dd、J=8.5、1.8Hz、H-61)、7.00(1H、d、J=1.8Hz、H-2’)、7.12(1H、d、J=1.8Hz、H-2”)、7.29(1H、dd、J=8.3、1.8Hz、H-6”)、7.44(1H、d、J=16.0Hz、H-1またはH-7)、7.51(1H、d、J=16.0Hz、H-1またはH-7);13CNMR(DMSO-d6):183.0、183.2、148.6、147.9、147.7、145.1、140.8、140.7、126.5、122.8、121.9、121.0、120.7、115.9、115.6、114.6、111.0、101.0、55.4;EIMS m/z(%):354(M+、16)、336(20)、328(54)、271(71)、192(53)、191(30)、177(100)、167(47)、163(49)、150(40)、149(24)、145(84)、135(48)、117(42)、89(57)、77(43)。
DMDC[1-(4-ヒドロキシフェニル)-7-(3,4-ジヒドロキシフェニル)-1,6-ヘプタジエン-3,5-ジオン]。黄色粉末、mp218-220℃;IR(KBr):3338、1627、962cm’1;1HNMR(DMSO-d6)δ6.06(1H、s、H-4)、6.59(1H、d、J=15.8Hz、H-2またはH-6)、6.69(1H、d、J=15.8Hz、H-2またはH-6)、6.83(1H、d、J=8.2Hz、H-5”)、6.79(2H、d、J=8.0Hz、H-3’、5’)、7.03(1H、s、H-2”)、7.09(1H、d、J=8.2Hz、H-6”)、7.45(1H、d、J=15.9Hz、H-1またはH-7)、7.47(1H、d、J=15.9Hz、H-1またはH-7)、7.57(2H、d、J=8.0Hz、H-2’、6’)、9.17(1H、brs、Ar-OH)、9.63(1H、brs、Ar-OH)、10.04(1H、brs、Ar-OH);EIMS m/z(%):324(M+、18)、306(8)、299(34)、298(90)、242(30)、241(100)、163(49)、161(26)、162(38)、147(87)、110(43)、119(39)、91(21)、44(34)。
BDC[1,7-ビス(4-ヒドロキシフェニル)-1,6-ヘプタジエン-3,5-ジオン]。黄色粉末、mp222-224℃;IR(KBr):3211、1620、1600、1269、1168、1140、955、831cm−1;1HNMR(DMSO-d6)δ6.03(1H、s、H-4)、6.68(2H、d、J=16.0Hz、H-2、6)、6.80(4H、d、J=8.0Hz、H-3’、5’、3”.5”),7.50(2H、d、J=16.0Hz、H-1、7)、7.55(4H、d、J=8.0Hz、H-2’、6’、2”、6”);EIMS m/z(%):308(M+、20)、290(14)、159(36)、146(100)、147(87)、119(38)、106(42)、90(42)、65(32)。
THTC =72.86%
THDC =15.98%
THDMDC =7.56%
THBDC =0.12%
合計 =96.39%
(a)スーパーオキシドフリーラジカル捕捉活性。NBT(ニトロブルーテトラゾリウム)法によりスーパーオキシドフリーラジカル捕捉活性を求めた。反応混合物は、EDTA(6.6mM)、NaCN(3μg)、リボフラビン(2μM)、NBT(50μM)、様々な濃度の試験薬のエタノール溶液、およびリン酸緩衝液(58mM、pH7.8)を最終体積3mlで含んだ。560nmで光学密度を測定した。試験管を白熱灯で15分間均一に照らし、その後光学密度を560nmで再び測定した。対照の吸光度値と試験化合物の吸光度値を比較することで、阻害割合とスーパーオキシドラジカル生成を測定した。μgでの濃度対阻害割合のプロットからIC5O値を得た。
(b)DPPHフリーラジカル捕捉活性。有色DPPHのメタノール溶液の還元に基づいてDPPH(1,1-ジフェニル-2-ピクリル-ヒドラジル)フリーラジカル捕捉活性を測定した。試験薬のエタノール溶液をDPPHのメタノール溶液に加えた場合のフリーラジカル捕捉活性は、DPPH溶液の516nmでの初期吸収および最終吸収の差に逆比例する。反応混合物は、DPPHおよび様々な濃度の試験薬の1×10-4mMメタノール溶液を含んだ。試験管と対照管の吸光度値を比較することで、阻害割合を求めた。
抗炎症活性(カラギーナン誘導肢浮腫法):
実験前に、動物(180−300gの体重のいずれかの性別のアルビノウィスターラット)を水は絶やさずに全て断食させそして体重を測り、番号を付けて、無作為に3匹からなる群に分けた。最初の足の体積をプレチスモメーターで測定し記録した。全ての群に、対応する試験物質を胃管を用いて経口で与えた。対照群には、10mL/Kgのビヒクル(0.5%、カルボキシメチルセルロースナトリウム塩)を与えた。30分後、全ての動物の左後肢の足裏部分に、1%カラギーナン0.1mLを皮下針を用いて皮下注射した。全ての動物に水20mL/Kg体重を投与して、3時間水のない状態を維持した(均一な水分補給を維持した)。3時間後、全ての動物の足の体積を2回測定し、2回の測定の平均値を記録した。試験物質を与えられた群の足浮腫と対照群の足浮腫を比較することで、足浮腫の阻害%を計算した。
Claims (11)
- 30−80%の範囲のテトラヒドロテトラヒドロキシクルクミン、4−20%の範囲のテトラヒドロデメチルクルクミン、5−25%の範囲のテトラヒドロデメチルモノデメトキシクルクミン、および0.1−10%の範囲のテトラヒドロビスデメトキシクルクミンを含む、テトラヒドロテトラヒドロキシクルクミン混合物の濃縮フラクションの組成物。
- 以下の工程、
(i)クルクマ・ロンガの根から得られる、クルクミン、モノデメトキシクルクミン、ビスデメトキシクルクミン、およびテトラヒドロキシクルクミンを含む天然のクルクミン混合物を、有機溶媒中、ルイス酸、ピリジン、およびヨウ化アルカリ金属の存在下、脱メチル化して、テトラヒドロキシクルクミン、デメチルモノデメトキシクルクミン、デメチルクルクミン、およびビスデメトキシクルクミンを含む粗脱メチル化クルクミン組成物を得ること、
(ii)該粗テトラヒドロキシクルクミン混合物を、有機溶媒中、水素ガスまたは水素供与体の存在下、金属触媒で水素化して、テトラヒドロテトラヒドロキシクルクミン、テトラヒドロデメチルクルクミン、テトラヒドロデメチルモノデメトキシクルクミン、およびテトラヒドロビスデメトキシクルクミンを含むテトラヒドロテトラヒドロキシクルクミン組成物を得ること、を含む、
請求項1に記載のテトラヒドロテトラヒドロキシクルクミン混合物が濃縮されたフラクションを製造する方法。 - 工程(i)で用いられる前記ルイス酸は、塩化アルミニウム、臭化アルミニウム、ヨウ化アルミニウム、および塩化ベリリウムからなる群より選択される、請求項2に記載の方法。
- 前記粗テトラヒドロキシクルクミン混合物をシリカゲルカラムクロマトグラフィーにかけて、約80−100%の範囲で濃縮されたテトラヒドロキシクルクミンを含有するフラクションを得る、請求項2又は3に記載の方法。
- 前記テトラヒドロキシクルクミン濃縮フラクションをシリカゲルカラムクロマトグラフィーにかけ、続いて結晶化により、純粋なテトラヒドロキシクルクミン、デメチルクルクミン、デメチルモノデメトキシクルクミン、およびビスデメトキシクルクミンを得る、請求項4に記載の方法。
- 工程(ii)で用いられる前記金属触媒は、パラジウム、ラネーニッケル、マンガン、または亜鉛から選択され、そして前記水素供与体は、ギ酸、酢酸、プロパン酸、およびギ酸アンモニウムからなる群より選択される、請求項2に記載の方法。
- 工程(ii)で用いられる前記有機溶媒は、アセトン、酢酸エチル、メタノール、エタノール、イソプロパノール、およびそれらの混合物からなる群より選択される、請求項2に記載の方法。
- 1種または複数の適した薬学的に許容可能な賦形剤と配合された、請求項1に記載のテトラヒドロテトラヒドロキシクルクミン混合物の濃縮フラクションを治療上有効量で含む、薬学的組成物または栄養補助食品。
- 前記テトラヒドロテトラヒドロキシクルクミン混合物の濃縮フラクションは、適した薬学的キャリア/賦形剤とともに、30−80%の範囲のテトラヒドロテトラヒドロキシクルクミン、4−20%の範囲のテトラヒドロデメチルクルクミン、5−25%の範囲のテトラヒドロデメチルモノデメトキシクルクミン、および0.1−10%の範囲のテトラヒドロビスデメトキシクルクミンを含む、請求項8に記載の薬学的組成物または栄養補助食品。
- 1種または複数種の薬学的に許容可能な賦形剤と混合して、(i)30−80%の範囲のテトラヒドロテトラヒドロキシクルクミン、4−20%の範囲のテトラヒドロデメチルクルクミン、5−25%の範囲のテトラヒドロデメチルモノデメトキシクルクミン、および0.1−10%の範囲のテトラヒドロビスデメトキシクルクミンを含むテトラヒドロキシクルクミン混合物の濃縮フラクションおよび/または(ii)30−80%の範囲のテトラヒドロキシクルクミン、4−20%の範囲のデメチルクルクミン、5−25%の範囲のデメチルモノデメトキシクルクミン、および0.1−10%の範囲のビスデメトキシクルクミンを含む、テトラヒドロキシクルクミンおよび他の脱メチル化クルクミン混合物の濃縮フラクションを1種以上治療上有効量で含む、炎症性疾患を治療するのに用いるための薬学的組成物。
- (i)30−80%の範囲のテトラヒドロテトラヒドロキシクルクミン、4−20%の範囲のテトラヒドロデメチルクルクミン、5−25%の範囲のテトラヒドロデメチルモノデメトキシクルクミン、および0.1−10%の範囲のテトラヒドロビスデメトキシクルクミンを含むテトラヒドロテトラヒドロキシクルクミン混合物の濃縮フラクション、または(ii)30−80%の範囲のテトラヒドロキシクルクミン、4−20%の範囲のデメチルクルクミン、5−25%の範囲のデメチルモノデメトキシクルクミン、および0.1−10%の範囲のビスデメトキシクルクミンを含む、テトラヒドロキシクルクミンおよび他の脱メチル化クルクミン混合物の濃縮フラクションを含む、5−リポキシゲナーゼ阻害剤。
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PCT/IN2005/000337 WO2007043058A1 (en) | 2005-10-13 | 2005-10-13 | Process for producing enriched fractions of tetrahydroxycurcumin and tetrahydrotetrahydroxy-curcumin from the extracts of curcuma longa |
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JP2009511573A JP2009511573A (ja) | 2009-03-19 |
JP5258571B2 true JP5258571B2 (ja) | 2013-08-07 |
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US (1) | US8568802B2 (ja) |
EP (1) | EP1933625B1 (ja) |
JP (1) | JP5258571B2 (ja) |
KR (1) | KR101281705B1 (ja) |
CN (1) | CN101227823B (ja) |
AU (1) | AU2005337331B2 (ja) |
WO (1) | WO2007043058A1 (ja) |
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US20080193573A1 (en) * | 2006-03-17 | 2008-08-14 | Gow Robert T | Extracts and methods comprising curcuma species |
WO2009066303A2 (en) | 2007-11-22 | 2009-05-28 | Ganga Raju Gokaraju | New synergistic phytochemical composition for the treatment of obesity |
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US6653327B2 (en) * | 1999-04-09 | 2003-11-25 | Sabinsa Corporation | Cross-regulin composition of tumeric-derived tetrahydrocurcuminoids for skin lightening and protection against UVB rays |
US6521668B2 (en) * | 1999-12-14 | 2003-02-18 | Avon Products, Inc. | Cosmetic composition and methods of use |
CN1301535A (zh) * | 1999-12-24 | 2001-07-04 | 天津市医药科学研究所 | 姜黄色素治疗乙型肝炎的应用 |
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US6875426B2 (en) * | 2002-03-28 | 2005-04-05 | L'oreal | Self-tanning composition containing a tetrahydrocurcuminoid and a self-tanning agent |
US20060165812A1 (en) * | 2005-01-21 | 2006-07-27 | Amershire Investment Corporation | Method and topical formulation for treating headaches |
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CN101227823B (zh) | 2012-05-23 |
AU2005337331A1 (en) | 2007-04-19 |
EP1933625A4 (en) | 2010-11-10 |
EP1933625A1 (en) | 2008-06-25 |
CN101227823A (zh) | 2008-07-23 |
US20100168248A1 (en) | 2010-07-01 |
KR20080059167A (ko) | 2008-06-26 |
EP1933625B1 (en) | 2014-07-09 |
US8568802B2 (en) | 2013-10-29 |
WO2007043058A1 (en) | 2007-04-19 |
JP2009511573A (ja) | 2009-03-19 |
KR101281705B1 (ko) | 2013-07-03 |
AU2005337331B2 (en) | 2011-10-20 |
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