JP5937596B2 - 活性型フラボノイド化合物の含量が増加されたウルシ抽出物及びその製造方法 - Google Patents
活性型フラボノイド化合物の含量が増加されたウルシ抽出物及びその製造方法 Download PDFInfo
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- JP5937596B2 JP5937596B2 JP2013524022A JP2013524022A JP5937596B2 JP 5937596 B2 JP5937596 B2 JP 5937596B2 JP 2013524022 A JP2013524022 A JP 2013524022A JP 2013524022 A JP2013524022 A JP 2013524022A JP 5937596 B2 JP5937596 B2 JP 5937596B2
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- urushi
- fisetin
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Images
Classifications
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- C07—ORGANIC CHEMISTRY
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- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
- A61K31/353—3,4-Dihydrobenzopyrans, e.g. chroman, catechin
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- 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)
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- A61K36/22—Anacardiaceae (Sumac family), e.g. smoketree, sumac or poison oak
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
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Landscapes
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- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Pyrane Compounds (AREA)
Description
ウルシ抽出物に含まれたフスティンとフィセチンの含量はHPLCを用いて分析し、標準品はシグマアルドリッチ社から購入した。HPLC分析条件はDetectorで254nmのUVを使用し、移動相は、酢酸:メタノール:アセトニトリル=70:20:10の5%混合溶液を使用した。流量は1ml/minで総10μlを注ぎ込んだ。カラムはC18(250mmx4.6mm, YMC Pack)を使用した。ポリフェノールの分析はFolin−ciocalteu’sフェノール試薬を用いてタンニン酸を標準物質にして分析した。発色後725nmで吸光度を測定して標準物質を用いた外部検量線法で計算した。
漆樹10kgに水100lを加えて、95℃で6時間抽出した。抽出する間4時間が経過して抽出液にフラボノイド成分がかなり多く含まれたとき、空気(酸素の割合20%(v/v))を1.5l/分の速度で抽出機の下部でバブリングさせた。バブリング時間は総12時間とし、1時間ごとに試料を採取して成分の分析を行った。
上記実施例<1−1>と同様に漆樹10kgに水100lを加えて、95℃でウルシ抽出物を抽出した。4時間の上記抽出過程を通じて抽出液にフラボノイド成分がかなり多く含まれたとき、高純度の酸素(純度95%(v/v)以上)を酸素ボンベを用いて1.2 l/分の速度で抽出機の下部でバブリングさせた。バブリング時間は総12時間とし、1時間ごとに試料を採取して成分の分析を行った。
漆樹10kgに水100lを加えて、95℃で6時間加熱しながら抽出した。抽出した抽出物は、濾過し、真空濃縮した後に粉末化して茶色の乾燥粉末で0.57kgを得た。上記最終抽出物粉末中のフスティンの濃度は17.3%(w/w)であり、フィセチンの濃度は1.63%(w/w)であった。かかる一般的なウルシ抽出物の製造過程を経たウルシ抽出物に含まれたフィセチン:フスティンの含量比は1:10.6であり、ポリフェノールの含量は53.1%であった。すなわち、バブリング処理をしない普通の抽出方法によって抽出したウルシ抽出物の場合は、フスティンがフィセチンの含量の10倍以上に多く含有されていた。
様々な抽出溶媒を使用して本発明によるウルシ抽出物を製造した。これのために、抽出溶媒には精製水、50%酒精、80%酒精、80%メタノール、100%酒精を使用し、それぞれの抽出溶媒を使用した抽出過程中、時間によるフスティンのフィセチンへの転化率を調査して90%の転化が行われる時間を相互比べた。ウルシ抽出物は、上記実施例と同様に漆樹10kgに10倍数の抽出溶媒を加えて、95℃で抽出し、0.3VVM(volume/volume/min)で高純度の酸素を抽出機の下部でバブリングしながら1時間ごとに抽出物をサンプリングしてフィセチンへの転化率を調査した。その結果を下記の表2に示した。
本発明によるウルシ抽出物の抗がん活性を分析するために、まず上記比較例1で製造した一般的なウルシ抽出方法によるウルシ抽出物と、実施例 <1−1>で製造した本発明のウルシ抽出物及び実施例6の「A」試料の抗がん活性を相互比べた。
V(腫瘍の大きさ、mean tumor volume、mm2)=AB2/2
本発明によるウルシ抽出物の抗酸化活性を分析するために、まず上記比較例1で製造した一般的なウルシ抽出方法によるウルシ抽出物と、実施例 <1−1>で製造した本発明のウルシ抽出物の抗酸化活性を相互比べた。
上記実施例 <1−1>と同様に、10kgのウルシに10倍数の水を添加して2回抽出し、濃縮して濃縮液で20lを作った。次いで酸素気体を0.4VVMで12時間バブリングした後、製造されたウルシ抽出物を濃縮してフスティンの含量が1.2%(w/w)、フィセチンの含量が15.8%(w/w)であるウルシ抽出物粉末 470gを得た。このとき、フィセチン:フスティンの含量比は1:0.076であった。
上記実施例 <1−1> 及び比較例1で得られた各抽出物100gを、水5,000mlに溶解し、次いでエチルアセテートを7,500mlを加えてミキサーを用いて 10分間激しく混合し、常温で放置して層隔離させた。上層のエチルアセテート層を収去し、溶媒を除いて成分の分析を行った結果、実施例 <1−1>の試料の場合(「A」という)はフィセチンの含量が42.5%(w/w)であり、比較例1の試料の場合(「B」という)はフィセチンの含量が7.5%(w/w)であった。
上記実施例6から得られた固形分10gをエタノール50mlに溶解させた後、これを500mlの冷たい水(冷蔵)に一度に注ぐ。このとき、フィセチンの黄色結晶が微細に一時に生成された。これを3,000rpmで20分間遠心分離して回収した。得られた結晶を乾燥させた後にHPLCで純度を分析した結果、水分含量 2.8%(w/w)、フィセチンの純度96.5%(w/w)であった。
Claims (6)
- ウルシを、抽出溶媒を用いて抽出して抽出物を製造する段階;及び
前記抽出物に酸素を含む気体バブリング処理を遂行する段階を含み、
前記酸素を含む気体バブリング処理により、前記抽出物中のフスティンがフィセチンに転化して、フィセチン:フスティンの含量比が1:0〜2:1の範囲であるウルシ抽出物の製造方法。 - 前記気体バブリング処理は、ウルシの抽出と同時に遂行、ウルシの抽出が完了した後に遂行、及びウルシ抽出物を濃縮した濃縮液で遂行からなる群から選ばれた少なくとも1つによって遂行されることを特徴とする請求項1に記載のウルシ抽出物の製造方法。
- 前記気体は空気であり、気体バブリング処理時間は6〜24時間であることを特徴とする請求項1に記載のウルシ抽出物の製造方法。
- 前記気体は95%(v/v)以上の高純度の酸素であり、気体バブリング処理時間は5〜12時間であることを特徴とする請求項1に記載のウルシ抽出物の製造方法。
- 前記気体バブリング処理は、抽出槽の内部で気体を抽出液に直接バブリングする方法、抽出槽の外部で抽出液を気体と混合しながら接触させる方法、及び気体で満たされた容器に抽出液を通過させながら接触させる方法からなる群から選ばれた少なくとも1つの方法によって遂行されることを特徴とする請求項1に記載のウルシ抽出物の製造方法。
- フスティンを含有する溶液に酸素を含む気体バブリング処理を施して、フィセチン:フスティンの含量比が1:0〜2:1の範囲になるようにする、前記フスティンをフィセチンに転化させる方法。
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