JP2007238468A - リパーゼ阻害活性物質およびそれを有する食品 - Google Patents
リパーゼ阻害活性物質およびそれを有する食品 Download PDFInfo
- Publication number
- JP2007238468A JP2007238468A JP2006059850A JP2006059850A JP2007238468A JP 2007238468 A JP2007238468 A JP 2007238468A JP 2006059850 A JP2006059850 A JP 2006059850A JP 2006059850 A JP2006059850 A JP 2006059850A JP 2007238468 A JP2007238468 A JP 2007238468A
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- JP
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- Prior art keywords
- escin
- saponin
- seeds
- saponins
- tochi
- 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.)
- Granted
Links
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- 235000013399 edible fruits Nutrition 0.000 claims description 58
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 17
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Abstract
【解決手段】あく抜き処理前の栃の実に含まれているエスシン、あく抜き処理後の栃の実に含まれているデアセチルエスシン、デサシルエスシンなどのサポニン類には、これまで知られていないリパーゼ阻害活性があることを見いだした。栃の実由来のリパーゼ阻害活性物質であるサポニンのマウスの体重に及ぼす影響試験から、かかる物質を有する食品等には、肥満抑制効果があることが確認された。
【選択図】図5
Description
松山利夫、「野生堅果類とくにトチノミとドングリ類のアク抜き技術とその分布」、国立民族学博物館研究報告、2、p498-528(1977) 松川泰三、「栃の実サポニンに就て(第1報)」、薬学雑誌、55、p350-357(1935) 吉川雅之、「薬用植物に見る生理機能10マロニエ」、食品と科学、p50-53(2000) Yoshikawa,M.、Murakami,T.、Matsuda,H.、Yamahara,J.、Murakami,N. 、and Kitagawa, I.、「Bioactive saponins and glycosides.III. horse chestnut.(1): The structures, inhibitory effects on ethanol absorption, and hypoglycemic activity of Escins Ia,IIa,Ib,IIb and IIIa from the seeds of Aesculus hippocastanum L.」、Chem. Pharm. Bull., 44, 1454-1464(1996) Yoshikawa, M.、Harada, E.、Murakami, T.、Matsuda, H.、Wariishi, N.、Yamahara, J.、Murakami, N. and Kitagawa,I.、「Escins Ia, IIa, Ib, IIb and IIIa, bioactive triterpene oligoglycosides, from the seeds of Aesculus hippocastanum L.: Their inhibitory effects on ethanol absorption, and hypoglycemic activity on glucose tolerance test.」、Chem. Pharm. Bull., 42, 1357-1359(1994) 山原條二、松田久司、村上敏之、島田ひろみ、吉川雅之、「薬用植物の血糖値上昇抑制作用と作用成分−トリテルペン配糖体の構造と活性」、和漢医薬学雑誌、13、p295-299(1996) 吉川雅之、「薬用植物の糖尿病予防成分 医食同源の観点から」、化学と生物、40、p172-178(2002) Guillaume, M. and Padioleau, F.、「Veintomic effect, vascular protection, anitiinflammatory and free radical scavenging properties of horse chestnut extract.」、Arzneimittelforschung, 44 , 25-35(1994) Sirori, C. R.、「Aescin : Phamacology, phamacokinetics and therapeutic profile.」、Phamacological Research, 44, 183-193(2001) 吉川雅之、村上敏之、大槻恵子、山原條二、松田久司、「生物活性サポニン及び配糖体(第13報).西洋トチノキ種子サポニン(3):高速液体クロマトグラフィーを用いたEscin Ia,IIa, Ib 及びIIbの定量分析」、薬学雑誌、119、p81-87(1999) Facino, R. M.,Carini, M., Moneti, G., Arlandini, E., Pietta, P. and Mauri, P., 「Mass spectrometric characterization of horse chestnut saponins (Escin).」、Org. Mass Spectrometry, 26, 989-990(1991) Zang, Z.、Koike, K.、Jia, Z.、Nikaido, T.、Guo, D. and Zheng, J.、「New saponins from the seeds of Aesculus chinensis」、Chem. Pharm. Bull., 47, 1515-1520(1999)
かかる構成において、前記化学物質は、栃の実由来であることを特徴とする。また、本発明の食品は、前記構成のリパーゼ阻害活性物質を有することを特徴とする。かかる構成において、前記食品は、肥満抑止効果を有する健康食品であることを特徴とする。
実験材料としては、本実験では、兵庫県北部で採取された栃の実を使用した。採取した栃の実は、トチノキ(Aesculus turbinata)の種子を用いた。木灰は牧野木材工業(岡山)から得た。0.05% TMS含有ピリジン-d5は、和光純薬工業(大阪)から購入した。β−エスシン(β-escin)、その他の特級試薬、HPLC分析用のメタノール、そして蒸留水は、ナカライテスク(京都)から入手した。
乾燥した栃の実を、4日間、水に浸漬して皮をやわらかくして剥いだ後、栃の実1kg(水分52.8 %, w/w)を3倍量の水で1時間、煮熟した。煮熟後の栃の実をあく抜きするため、木灰1kgに60℃の温湯(1.4リットル)を加えたペースト状の木灰液を用意した。これに栃の実1kgを浸漬し、さらに48時間放置した。その後、あく抜き状態を食味により確認した後、栃の実を水道水で洗浄した。あく抜き状態の判断は、食味により苦味の程度を熟練作業者が官能評価した。
TLCプレートは、silica gel 60F254 (MERCK製)を使用した。展開溶媒はクロロホルム/メタノール/蒸留水(65:35:10, v/v)の下層を用いた。発色は10 %硫酸溶液を噴霧し、150℃で加熱してスポットを確認した。TLCの標準物質としては、市販のβ−エスシン(Rf値0.24)を非特許文献4に記載のYoshikawaらの方法でアルカリ加水分解して得たデサシルエスシン(desacylescin:Rf値 0.12)を用いた。
栃の実中のサポニンの組成と含有量を分析するため、あく抜き前の皮剥栃の実からサポニンの抽出と精製を非特許文献4に記載のYoshikawaらの方法に準じて行った。すなわち、乾燥栃の実を、4日間、水に浸漬して皮をやわらかくした後、皮を除去した。この栃の実4kg(水分52.2 %, w/w)を1週間、メタノールに浸漬した後、濾過した。得られたメタノール抽出物を濃縮乾固して乾燥物154 gを得た。この抽出物を、Diaion HP-20カラム(長さ500 mm×内径 60 mm、日本錬水製、東京)に供し、蒸留水3000 mlで糖類画分を、メタノール3000 mlでサポニンを含む画分を、そして酢酸エチル3000 mlで脂質画分を溶出した。このカラムでのメタノール溶出画分を濃縮乾固して、粗サポニン画分の56 gを得た。
HPLC分析には、島津製作所製のLC-2010AシステムとクロマトパックCR8Aを用いた。分析用カラムとしてワイエムシィ製のYMC-Pack ODS AM(AM312-3)カラム(長さ150 mm×内径6 mm )を、また、分取用カラムには、ワイエムシィ製のYMC-Pack ODS AM (AM 322)カラム(長さ150 mm×内径10 mm )を利用した。移動相としてメタノール/ 10 mMリン酸緩衝液(pH 2.7)(62:38, v/v)を用い、溶出速度として、分析用カラムでは、0.8 ml/minに、分取用カラムでは3.0 ml/minに合わせた。検出は203 nmの波長で行った。
あく抜き処理前の栃の実成分のエスシンIa、IIa、Ib、IIbのそれぞれの成分をHPLCで分離精製した。そして、木灰浸漬時とほぼ同様のアルカリ度に調製した5 %炭酸カリウム溶液(pH 11.7)中で、個々の成分を48時間、室温で静置した。その後、0.1 M塩酸水溶液で中和した後、C18マキシクリーンカートリッジカラム(オルテック製,東京)にかけて40 %メタノールで洗浄後、70 %メタノールで溶出し、0.45μmのメンブレンフィルターで濾過後、HPLC分析にかけた。
核磁気共鳴スペクトル(1H-NMR、13C-NMR)による分析には、日本電子社製のJEOL JNM-A400 FT-NMR(400Mz)を用いた。試料を0.05 %TMS含有ピリジン-d5に溶解し測定にかけた。質量分析には、サーモクエスト社製のイオントラップ型質量分析装置モデルLCQ Deca XPを用いて、正イオンモードでのエレクトロスプレーイオン化(electrospray ionization、ESI)法により解析した。水分測定は、島津製作所製の赤外水分計EB-340MOCにより分析した。
a)あく抜き処理前後の栃の実中のサポニン含量について
あく抜き後の栃の実中のサポニン残存量を把握する目的で、前記要領で、あく抜き処理前の栃の実と、あく抜き処理後のものから同様の操作でサポニンを抽出し、Diaion HP-20カラムとChromatorex ODS 1024Tカラムにより精製したサポニン画分の重量を比較した。
あく抜き処理により栃の実中のサポニン類の化学変化を調べるため、あく抜き処理前後の栃の実から抽出したサポニン画分をHPLC分析にかけた。図1に示すように、その結果、あく抜き処理前の栃の実のサポニンの溶出位置は、市販の標準品のβ-エスシンに含まれる4つの成分の保持時間と一致した。
TLC分析で、あく抜き処理後の主要なサポニンとして、デサシルエスシンとエスシンとデサシルエスシンの間の位置に未知のサポニンが確認された。なお、微量なエスシンも確認された。そこで、あく抜き処理により生成した図2のi’〜iv’の未知のサポニンの化学構造の確認のため、HPLCでそれぞれを単離し、質量分析、1H-NMR、そして13C-NMRによる構造解析を行った。質量分析の結果では、表1に示すように、エスシン類の22位のアセチル基が脱離することに一致する分子イオンピークが得られた。また1H-NMR分析により、表2に示すように、エスシンIaとIIaの21位のチグロイル基とIbとIIbのアンゲロイル基の存在が確認された。
トリオレインを基質とした場合の膵臓リパーゼ阻害活性の測定には、あく抜き処理前、あるいは、あく抜き処理後の栃の実のメタノール抽出物を、Diaion HP-20カラムとChromatorex ODS 1024Tカラムを用いて精製して得たサポニン画分を用いた。
a)トリオレインを基質とした場合のリパーゼ阻害活性測定
トリオレインを基質とした場合の、ブタ膵臓リパーゼ阻害活性の測定は、リパーゼ反応により遊離したオレイン酸を、平山らのローダミン6G試薬で比色定量する方法で行った。
0.1 %デオキシコール酸ナトリウムを含む0.1 M Mcllvaine緩衝液(pH7.4)0.04 mlに、同様の緩衝液で溶解した0.1 mM 4-methylumbelliferyl oleate (4-MU oleate) 0.1 mlと、被検物である栃の実サポニン類を70 %に溶解した溶液0.01 mlをよく混合した後、ブタ膵臓リパーゼ(TypeII)を同様の緩衝液で溶解した酵素液0.05 mlを加えて、37℃、20分間反応させた。
尚、食餌の配合は表5の通りである。
Claims (4)
- 請求項1記載のリパーゼ阻害活性物質において、
前記化学物質は、栃の実由来であることを特徴とするリパーゼ阻害活性物質。 - 請求項1または2に記載のリパーゼ阻害活性物質を有することを特徴とする食品。
- 請求項3に記載の食品において、
前記食品は、肥満抑止効果を有する健康食品であることを特徴とする食品。
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JP2021530495A (ja) * | 2018-07-09 | 2021-11-11 | エルジー ハウスホールド アンド ヘルスケア リミテッド | 脱毛防止または毛髪成長促進用の組成物 |
KR102074314B1 (ko) * | 2018-10-22 | 2020-03-17 | 주식회사 엘지생활건강 | 탈모방지 또는 모발성장 촉진용 조성물 |
KR20210086456A (ko) * | 2019-12-30 | 2021-07-08 | 주식회사 엘지생활건강 | 에스신을 포함하는 탈모 방지 및 발모 촉진용 조성물 |
KR102537521B1 (ko) | 2019-12-30 | 2023-05-26 | 주식회사 엘지생활건강 | 탈모 방지 및 발모 촉진용 조성물 |
CN114053183A (zh) * | 2021-10-18 | 2022-02-18 | 深圳市兰亭科技股份有限公司 | 一种具有多靶点头皮止痒功效的组合物 |
CN114053183B (zh) * | 2021-10-18 | 2024-02-13 | 深圳市兰亭科技股份有限公司 | 一种具有多靶点头皮止痒功效的组合物 |
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