JP5160149B2 - 柿ポリフェノールオリゴマー - Google Patents
柿ポリフェノールオリゴマー Download PDFInfo
- Publication number
- JP5160149B2 JP5160149B2 JP2007165247A JP2007165247A JP5160149B2 JP 5160149 B2 JP5160149 B2 JP 5160149B2 JP 2007165247 A JP2007165247 A JP 2007165247A JP 2007165247 A JP2007165247 A JP 2007165247A JP 5160149 B2 JP5160149 B2 JP 5160149B2
- Authority
- JP
- Japan
- Prior art keywords
- polyphenol
- epigallocatechin
- egcg
- gallate
- catechin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- WMBWREPUVVBILR-UHFFFAOYSA-N GCG Natural products C=1C(O)=C(O)C(O)=CC=1C1OC2=CC(O)=CC(O)=C2CC1OC(=O)C1=CC(O)=C(O)C(O)=C1 WMBWREPUVVBILR-UHFFFAOYSA-N 0.000 claims description 80
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- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 claims description 60
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Images
Description
B環のピロガロール率が70〜90%、ガロイル化率が40〜70%であってエピガロカテキン−3−O−ガレート三量体を含有し、
B環のピロガロール率は、
エピガロカテキン(EGC)、エピガロカテキン−3−O−ガレート(EGCg)のカテキン単量体と、
エピガロカテキン(EGC)、エピガロカテキン−3−O−ガレート(EGCg)からのカテキン−メルカプトエタノール誘導体(EGC−ME、EGCg−ME)と、
全カテキン単量体量 及び、全カテキン-メルカプトエタノール(ME)誘導体量とを用い、
B環ピロガロール率=100×{(EGC)+(EGCg)+(EGC−ME)+(EGCg−ME)}/{(全カテキン単量体量)+(全カテキン-メルカプトエタノール(ME)誘導体量)}の計算式から算出され、
ガロイル化率は、
エピカテキン−3−O−ガレート(ECg)、エピガロカテキン−3−O−ガレート(EGCg)のカテキン単量体と、
エピカテキン−3−O−ガレート(ECg)、エピガロカテキン−3−O−ガレート(EGCg)からのカテキン−メルカプトエタノール誘導体(ECg−ME、EGCg−ME)と、
全カテキン単量体量 及び、全カテキン-メルカプトエタノール(ME)誘導体量とを用い、
ガロイル化率=100×{(ECg)+(EGCg)+(ECg−ME)+(EGCg−ME)}/{(全カテキン単量体量)+(全カテキン-メルカプトエタノール(ME)誘導体量)}の計算式から算出されることを特徴とする柿ポリフェノールオリゴマーに係るものである。
サンフェノンBG-3の代わりにサンフェノンEGCg20gを用いて同様に低分子化反応、吸着樹脂精製、セファデックス精製を行って、粗製粉末(P−2と略す)26.6g、精製粉末(P−2Fと略す)5.7gを得た。
サンフェノンBG-3の代わりにアセンヤク30g用いて同様に低分子化反応、吸着樹脂精製、セファデックス精製を行って、粗製粉末(P−3と略す)25.4g、精製粉末(P−3Fと略す)5.3gを得た。
サンフェノンBG-3の代わりにサンフェノンEGCg20gを用いて同様に低分子化反応、吸着樹脂精製、セファデックス精製を行って、粗製粉末(G−2と略す)31.2g、精製粉末(G−2Fと略す)4.3gを得た。
サンフェノンBG-3の代わりにアセンヤク30g用いて同様に低分子化反応、吸着樹脂精製、セファデックス精製を行って、粗製粉末(G−3と略す)30.4g、精製粉末(G−3Fと略す)5.0gを得た。
試料濃度25mg/mlに調製した検体300μlをチオール試薬(2−メルカプトエタノール(5%)と塩酸(0.1%)を含む60%エタノール)1.2mlと混合し,70℃で7時間加熱後、室温5時間放置した。反応液をそのまま高速液体クロマトグラフィー(HPLC)で分析した。条件は以下の通りである。カラム:Cosmosil 5C18-AR II (ナカライテスク(株)) (250 × 4.6 mm i.d.)、 溶媒:4→30%(39分)−30→75%(15分) アセトニトリル−50mMリン酸、 流速:0.8ml/min、検出:JASCOフォトダイオードアレイMD−910検出器。試料中のカテキン構成ユニットの量はカテキン単量体(C、EC、EGC、ECg、EGCg)及びカテキン−メルカプトエタノール(ME)誘導体(C−ME、EC−ME、EGC−ME、ECg−ME、EGCg−ME)の274nmにおけるピーク面積から定量した。検量線は茶カテキン標準品を用いて作成した。平均重合度は下記の計算式より算出した。
平均重合度=(全カテキン-ME誘導体量/全カテキン単量体量)+1
上記式において、全カテキン-ME誘導体量及び全カテキン単量体量はnmol/gを表す。
ピロガロール率は、(1)で得られたカテキン単量体(C、EC、EGC、ECg、EGCg)及びカテキン−ME誘導体(C−ME、EC−ME、EGC−ME、ECg−ME、EGCg−ME)量を用いて下記の計算式より算出した。
B環ピロガロール率=100×{(EGC)+(EGCg)+(EGC−ME)+(EGCg−ME)}/{(全カテキン単量体量)+(全カテキン-ME誘導体量)}
上記式において、全カテキン-ME誘導体量及び全カテキン単量体量はnmol/gを表す。
ガロイル化率は、(1)で得られたカテキン単量体(C、EC、EGC、ECg、EGCg)及びカテキン−ME誘導体(C−ME、EC−ME、EGC−ME、ECg−ME、EGCg−ME)量を用いて下記の計算式より算出した。
ガロイル化率=100×{(ECg)+(EGCg)+(ECg−ME)+(EGCg−ME)}/{(全カテキン単量体量)+(全カテキン-ME誘導体量)}
上記式において、全カテキン-ME誘導体量及び全カテキン単量体量はnmol/gを表す。
であることは、渋柿由来ポリフェノールが主としてエピガロカテキンやエピガロカテキン−3−O−ガレートから構成されていることを示している。
上記物質のα−グルコシダーゼ阻害活性を以下の方法で測定した。
乾燥した各試料50mgに水20mlを加え、超音波処理と振盪を行い、一定量を分取し、0.1Mリン酸緩衝液(pH7.0)で希釈し、180μg/mlの試料溶液とした。
2)α−グルコシダーゼ阻害活性の測定法
50mMスクロース溶液(pH7.0の0.1Mリン酸緩衝液)400μl、0.1Mリン酸緩衝液(pH7.4)で希釈した試料溶液100μlを混合し、3分間37℃でプレインキュベートを行った。これに緩衝液で希釈したα−グルコシダーゼ溶液(東洋紡製α−グルコシダーゼ(II)100μl を加え、37℃で30分間反応後、氷冷下1Mトリス緩衝液600μlを添加し、反応を停止した。反応液40μlを分取し、生成したグルコース量はグルコースCII-テストワコー(和光純薬製)を用いて505nmの吸光度を測定した(検体)。対照として、試料溶液に換えて、0.1Mリン酸緩衝液を同量加えた場合の吸光度(対照A)、及び酵素溶液に換えて、0.1Mリン酸緩衝液を同量加えた場合の吸光度(対照B)を同時に測定し、酵素阻害率を下記の計算式から算出した。
酵素阻害率(%)=100−100×(検体−対照2)/(対照1−対照2)
(1)と同様各試料物質のα−アミラーゼ阻害活性を以下の方法で測定した。
乾燥した各試料50mgに水20mlを加え、超音波処理と振盪を行い、一定量を分取し、50mM酢酸緩衝液(pH6.5)で希釈し、50μg/ml及び15μg/mlの試料溶液とした。
2)α−アミラーゼ阻害活性の測定法
0.5重量%可溶性デンプン200μl、20mMCaCl2、100mMNaClを含む50mM酢酸緩衝液(pH6.5)で希釈した試料溶液100μl及び緩衝液100μlを混合し、3分間37℃でプレインキュベートを行った。これに緩衝液で希釈したα−アミラーゼ溶液(ブタ膵臓由来のα−アミラーゼ(Sigma社製のSigma A6255))100μl(約0.6U/ml)を加え、37℃で15分間反応後、氷冷下0.1M塩酸500μlを添加し、反応を停止した。反応液250μlを分取し、0.2mMヨウ素液3mlを加え、660nm波長での吸光度を測定した。対照として、酵素を入れないもの(対照1)、及び酵素を入れたもの(対照2)を同時に測定し、酵素阻害率は下記の計算式から算出した。
酵素阻害率(%)=(検体−対照2)÷(対照1−対照2)×100
調べた。その結果、図5から明らかなように、α−アミラーゼ活性は柿ポリフェノールオリゴマーの重合度が大きいほど強く抑制され、阻害率と平均重合度との相関係数は0.86であった。α−グルコシダーゼ活性は図6及び図7のように柿ポリフェノールオリゴマーのガロイル化率、ピロガロール率が高い程強く抑制され、阻害率とピロガロール率との相関係数は0.85、ガロイル化率との相関係数は0.94であり、非常に高い相関性を有していた。
Wistar系ラット(雄)に対し、ストレプトゾトシン(STZ)を体重kg当たり50mgとなるように腹腔内投与して作製された。実験開始時に血糖値をもとに群分けし、糖尿病ラットの各群には、以下に示す試料物質を投与した。
2.糖尿病対照群(以下、Control群)(n=7):通常飼料、水を与えた。
3.柿ポリフェノールポリマー群(以下、Polymer群)(n=7):柿ポリフェノールポリマーを10mg/kg/dayで連日経口投与
4.柿ポリフェノールオリゴマー群(以下、Oligomer群)(n=7):柿ポリフェノールオリゴマーを10mg/kg/dayで連日経口投与
2.糖尿病対照群(以下、Control群)(n=13):通常飼料、水を与えた。
3.柿ポリフェノールポリマー群(以下、Polymer群)(n=13):柿ポリフェノールポリマーを10mg/kg/dayで連日経口投与
4.柿ポリフェノールオリゴマー群(以下、Polymer群)(n=13):柿ポリフェノールオリゴマーを10mg/kg/dayで連日経口投与
肝組織中のトリグリセリド、総コレステロール、脂質過酸化はdb/dbマウスで著しく上昇していたが、Oligomer群でいずれの脂質も有意に低下し、脂質過酸化はほぼ正常群レベルにまで低下した。肝臓核内転写因子の発現量を解析した結果、糖尿病状態で発現量が増加したSREBP-1、SREBP-2、NF-κBはPolymer群で低下傾向にあるが、Oligomer群では有意に低下し、特にNF-κBについては正常群レベルにまで低下した。糖尿病状態で発現量が減少したPPARαはOligomer群で増加傾向を示した。
Claims (5)
- 柿タンニンから得られ、エピガロカテキン(EGC)、エピカテキン−3−O−ガレート(ECg)、エピガロカテキン−3−O−ガレート(EGCg)を含み得る柿ポリフェノールオリゴマーであって、
B環のピロガロール率が70〜90%、ガロイル化率が40〜70%であってエピガロカテキン−3−O−ガレート三量体を含有し、
B環のピロガロール率は、
エピガロカテキン(EGC)、エピガロカテキン−3−O−ガレート(EGCg)のカテキン単量体と、
エピガロカテキン(EGC)、エピガロカテキン−3−O−ガレート(EGCg)からのカテキン−メルカプトエタノール誘導体(EGC−ME、EGCg−ME)と、
全カテキン単量体量 及び、全カテキン-メルカプトエタノール(ME)誘導体量とを用い、
B環ピロガロール率=100×{(EGC)+(EGCg)+(EGC−ME)+(EGCg−ME)}/{(全カテキン単量体量)+(全カテキン-メルカプトエタノール(ME)誘導体量)}の計算式から算出され、
ガロイル化率は、
エピカテキン−3−O−ガレート(ECg)、エピガロカテキン−3−O−ガレート(EGCg)のカテキン単量体と、
エピカテキン−3−O−ガレート(ECg)、エピガロカテキン−3−O−ガレート(EGCg)からのカテキン−メルカプトエタノール誘導体(ECg−ME、EGCg−ME)と、
全カテキン単量体量 及び、全カテキン-メルカプトエタノール(ME)誘導体量とを用い、
ガロイル化率=100×{(ECg)+(EGCg)+(ECg−ME)+(EGCg−ME)}/{(全カテキン単量体量)+(全カテキン-メルカプトエタノール(ME)誘導体量)}の計算式から算出され、
エピガロカテキン−3−O−ガレート三量体は、
の化学構造を持つことを特徴とする柿ポリフェノールオリゴマー。 - 抗酸化活性と、転写因子NF−κBの活性化阻害活性とが高められることを特徴とする請求項1記載の柿ポリフェノールオリゴマー。
- α―グルコシダーゼ及び/又はα―アミラーゼに対してエピガロカテキン−3−O−ガレートよりも強い阻害活性を有することを特徴とする請求項1記載の柿ポリフェノールオリゴマー。
- 疾患を改善し得る作用は、抗がん作用、抗炎症作用、動脈硬化抑制作用、抗歯周病作用、抗う蝕作用であることを特徴とする請求項1、2のいずれかに記載の柿ポリフェノールオリゴマー。
- 疾患を改善し得る作用は、抗糖尿病作用、抗肥満作用であることを特徴とする請求項1、3のいずれかに記載の柿ポリフェノールオリゴマー。
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