JP2012510270A - 共役リノール酸含有水性ナノエマルジョン組成物 - Google Patents
共役リノール酸含有水性ナノエマルジョン組成物 Download PDFInfo
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- JP2012510270A JP2012510270A JP2011538572A JP2011538572A JP2012510270A JP 2012510270 A JP2012510270 A JP 2012510270A JP 2011538572 A JP2011538572 A JP 2011538572A JP 2011538572 A JP2011538572 A JP 2011538572A JP 2012510270 A JP2012510270 A JP 2012510270A
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- weight
- linoleic acid
- group
- conjugated linoleic
- 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
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- JBYXPOFIGCOSSB-GOJKSUSPSA-N 9-cis,11-trans-octadecadienoic acid Chemical compound CCCCCC\C=C\C=C/CCCCCCCC(O)=O JBYXPOFIGCOSSB-GOJKSUSPSA-N 0.000 title claims abstract description 84
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 title claims abstract description 77
- 229940108924 conjugated linoleic acid Drugs 0.000 title claims abstract description 74
- 239000000203 mixture Substances 0.000 title claims abstract description 66
- 239000007908 nanoemulsion Substances 0.000 title claims abstract description 57
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 95
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 59
- 235000011187 glycerol Nutrition 0.000 claims abstract description 24
- 239000003995 emulsifying agent Substances 0.000 claims abstract description 16
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 claims abstract description 13
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- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 42
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- 150000002148 esters Chemical class 0.000 claims description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 claims description 2
- PXEDJBXQKAGXNJ-QTNFYWBSSA-L disodium L-glutamate Chemical compound [Na+].[Na+].[O-]C(=O)[C@@H](N)CCC([O-])=O PXEDJBXQKAGXNJ-QTNFYWBSSA-L 0.000 claims description 2
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- LPUQAYUQRXPFSQ-DFWYDOINSA-M monosodium L-glutamate Chemical compound [Na+].[O-]C(=O)[C@@H](N)CCC(O)=O LPUQAYUQRXPFSQ-DFWYDOINSA-M 0.000 claims description 2
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- 229940079781 sodium cocoyl glutamate Drugs 0.000 claims description 2
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- IWIUXJGIDSGWDN-UQKRIMTDSA-M sodium;(2s)-2-(dodecanoylamino)pentanedioate;hydron Chemical compound [Na+].CCCCCCCCCCCC(=O)N[C@H](C([O-])=O)CCC(O)=O IWIUXJGIDSGWDN-UQKRIMTDSA-M 0.000 claims description 2
- KNYAZNABVSEZDS-UHFFFAOYSA-M sodium;2-octadecanoyloxypropanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC(=O)OC(C)C([O-])=O KNYAZNABVSEZDS-UHFFFAOYSA-M 0.000 claims description 2
- TUBPSFQENHCYBW-HVDRVSQOSA-N (2s)-2-aminopentanedioic acid;2-[bis(2-hydroxyethyl)amino]ethanol Chemical compound OC(=O)[C@@H](N)CCC(O)=O.OCCN(CCO)CCO TUBPSFQENHCYBW-HVDRVSQOSA-N 0.000 claims 1
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- AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical compound CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 description 13
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- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 7
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- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 6
- 229940039781 leptin Drugs 0.000 description 6
- NRYBAZVQPHGZNS-ZSOCWYAHSA-N leptin Chemical compound O=C([C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](N)CC(C)C)CCSC)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](CS)C(O)=O NRYBAZVQPHGZNS-ZSOCWYAHSA-N 0.000 description 6
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- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 5
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- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 5
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- RLFWWDJHLFCNIJ-UHFFFAOYSA-N 4-aminoantipyrine Chemical compound CN1C(C)=C(N)C(=O)N1C1=CC=CC=C1 RLFWWDJHLFCNIJ-UHFFFAOYSA-N 0.000 description 4
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Abstract
【選択図】図7
Description
本発明の水性ナノエマルジョン組成物は有効成分として共役リノール酸を含む。共役リノール酸の種類には限定がなく、何れの市販共役リノール酸を用いてもよい。このような共役リノール酸は、例えば、Tonalin(登録商標)CLA(Cognis, Germany)、Clarinol(登録商標)CLA(Lipid Nutrition B.V., Netherlands)、CLA(HK Biotech, Korea)などを含む。本発明の水性ナノエマルジョン組成物は、5〜50重量%、好ましくは10〜45重量%、そしてさらに好ましくは15〜40重量%の共役リノール酸を含んでいる。本発明では、共役リノール酸の量が5重量%未満のとき、共役リノール酸の生理活性効果が劣り、共役リノール酸の量が50重量%を超えると、共役リノール酸がよく溶解しないか、又は長時間空気に露出すると、析出する恐れがある。
下記表1の組成で下記方法によって、水性ナノエマルジョン組成物を製造した。共役リノール酸とレシチンを糖エステルとエタノールに溶解した。次いで、水及びグリセリンを加え、十分に撹拌した。得られた混合物を高圧マイクロフルイダイザー(Microfluidizer)に1,000barで連続5回通過させた後、混合物を減菌ろ過して、ナノエマルジョン組成物を得た。この組成物を小分けし、包装した。
下記表2の構成組成を用いたことを除いては、上記実施例1と同様の方法で水性ナノエマルジョン組成物を製造した。
下記表3の構成組成を用いたことを除いては、上記実施例1と同様の方法で水性ナノエマルジョン組成物を製造した。
下記表4の構成組成を用いたことを除いては、上記実施例1と同様の方法で水性ナノエマルジョン組成物を製造した。
下記表5の構成組成を用いたことを除いては、上記実施例1と同様の方法で水性ナノエマルジョン組成物を製造した。
下記表6の構成組成を用いたことを除いては、上記実施例1と同様の方法で水性ナノエマルジョン組成物を製造した。
下記表7の構成組成を用いたことを除いては、上記実施例1と同様の方法で水性ナノエマルジョン組成物を製造した。
下記表8の構成組成を用いたことを除いては、上記実施例1と同様の方法で水性ナノエマルジョン組成物を製造した。
下記表9の構成組成を用いたことを除いては、上記実施例1と同様の方法で水性ナノエマルジョン組成物を製造した。
下記表10の構成組成を用いたことを除いては、上記実施例1と同様の方法で水性ナノエマルジョン組成物を製造した。
実施例1〜10で調製された組成物の外観を層分離及び析出に関して肉眼で観察した。25℃及び45℃の恒温槽に保管した後に共役リノール酸の含量変化によって安定性を測定した。
試料20〜25mgを2mLの0.5N NaOHメタノール溶液に加えて振盪し、次いで80℃の熱浴で10分間加熱した後、冷水で冷却した。そこに、2mLのBH3を加え、次いで80℃の熱浴中で8〜10分間加熱した後、冷水で冷却した。そこに、3mLの内部標準溶液(500mgのウンデカン酸を100mLのn−ヘキサンに溶解した溶液)を加え、次いで80℃の熱浴中で3分間加熱した後、冷水で冷却した。そこに5mLの飽和NaCl溶液を加え、層分離した後、上層を取り、そこに0.5gの無水硫酸ナトリウムを加えて水分を除去した。調製した試験液1μLをガスクロマトグラフィー(カラム:DB−Wax、インジェクター温度:270℃、検出器温度:290℃、カラム温度:190℃〜240℃、温度を1分当り2℃ずつ上げた)で分析した。
1)層分離、析出及び安定性
室温(25℃)におけるpH2、5、7及び10でのpH安定性を層分離及び析出に関して肉眼で観察した。その結果を下記表12に示している。
エタノールを溶解補助剤として含むナノエマルジョンとエタノールを含まないナノエマルジョンを比較するために、下記表13に示されるようなナノエマルジョン組成物を調製した。その粒子径、透明度、粘度及び45℃での貯蔵安定性を測定し、その結果を下記表14に示している。その粒子分布はPhotal ELS−Zを用いて測定した。さらに、エタノールを含むナノエマルジョンとエタノールを含まないナノエマルジョンを走査型電子顕微鏡(JEOL, Japan)で撮影し、その結果を図2に示している。
本発明の共役リノール酸含有水性ナノエマルジョン組成物の抗−肥満効果を調べるために、インビトロ及びインビボ実験を行った。DMSO(ジメチルスルホキシド、対照)、オルリスタット(Orlistat、抗−肥満薬、陽性対照)、CLA及び本発明の共役リノール酸含有水性ナノエマルジョン(以下、「N−CLA」という)を試料として用いた。N−CLAは実施例1に記載の方法によって製造した。
(1)細胞培養及び試料処理
3T3−L1前駆脂肪細胞を、10%ウシ胎仔血清、100unit/mLペニシリン及び100μg/mLストレプトマイシンを含有するダルベッコ改変イーグル培地(DMEM)中、37℃、5%CO2インキュベータで培養した。細胞の70〜80%がコンフルエントになったとき、分化誘導物質であるデキサメタゾン、ピオグリタゾン(pioglitazone)、IBMX(3−イソブチル−1−メチルキサンチン)インスリン及びFBSを含有するDMEMで細胞を前分化させた後、インスリン、ピオグリタゾン、FBSを含有するDMEMで分化させた。分化後、10%FBSとインスリンを含有する成長培地で脂質を成熟させた。試料をDMSOに溶かしたて、最終濃度10μg/mLで処理した。
96ウェルプレートの各ウェルに1×104個の前駆脂肪細胞を分注して、各サンプルを処理した。次いで、37℃、5%CO2インキュベータで細胞を24時間培養した。24時間経過後、MTT(リン酸緩衝生理食塩水中、最終濃度:0.4μg/mL)を処理し、次いで細胞を4時間培養した。形成されたホルマザン(Formazan)結晶をDMSO:エタノール(1:1)で溶解し、マイクロプレートリーダ(SUNRISE, TECAN, Austria)により540nmで吸光度を測定した。細胞生存率は、対照群の吸光度値に対する試料処理群の吸光度値の割合で決定し、その結果を図3に示している。図3から明らかなように、オルリスタット群、CLA群及びN−CLA群の細胞生存率は、それぞれ103%、100%、103%である。従って、対照群のそれと、統計的に有意な差はない。
6ウェルプレートの各ウェルに1×105個の細胞を分注し、分化させた。 分化後8日目に培地を除去し、氷冷したPBSで2回洗浄した。細胞を室温で1時間、10%ホルマリンで固定し、0.2%Oil red O(イソプロパノール中)で30分間染色後、蒸留水で洗浄した。そこに、イソプロパノールを加えて、油滴を溶かした後、490nmでの吸光度として中性脂肪の含量を測定した。その結果を図4及び5に示している。オルリスタット群、CLA及群びN−CLA群は、対照群に比べて、中性脂肪が減少する傾向を示した。
6ウェルプレートの各ウェルに1×105個の細胞を分注した。細胞の70%がコンフルエントになったとき、細胞をMDI培地(分化培地)と各試料で同時に処理した後、48時間培養した。分化後8日目に、Oil red O染色で中性脂肪の含量を測定した。その結果を図6に示している。図6から明らかなように、CLA群は対照群と類似な中性脂肪含量を示したのに対して、オルリスタット群及びN−CLA群では、対照群に比べて中性脂肪の含量がそれぞれ12.5%及び16.3%と統計的有意に減少した。
グリセロールを遊離グリセリン試薬(Sigma, USA)を用いる酵素反応法で定量した。37℃に予め温めた遊離グリセリン試薬0.8mLに、細胞を試料で24時間処理した後採取した培地10μLを加えた後、混合物の反応を37℃の水浴で5分間実施した。グリセロールの定量のために、標準グリセロール(25μg/10μL)を上記と同様にして反応させて、540nmにおける吸光度を測定した。グリセロールの含量は下記の計算式を用いて算出した。
グリセロール含量={(A試料−Aブランク))/(A標準品−Aブランク)}×標準品の濃度
食欲に関連するホルモンとして知らされているレプチンの分泌量が調節されているか否かを確認するために、実験を行った。脂肪細胞から分泌されたレプチンの量を、試料で脂肪細胞を処理した後に合わせた培地上で酵素免疫測定法(ELISA)により測定した。100μlのウサギ抗マウスレプチンIgGをELISAプレートに分注した。ELISAプレートを4℃で一晩培養し、TPBS(PBS+0.05%Tween20)で3回洗浄し、そこに合わせた培地100μLを加えた後、1時間室温で培養した。ELISAプレートを再びTPBSで3回洗浄し、そこに二次抗体を加え、1時間室温で培養した後、TPBSで3回洗浄した。アルカリホスファターゼ結合性基質キットを用いて発色を促進させた後、ELISAリーダ(SUNRISE, TECAN, Austria)によって490nmでの吸光度を測定した。その結果を図8に示している。図8から明らかなように、オルリスタット群、CLA群及びN−CLA群のレプチン分泌量は、対照群と比べて、それぞれ11.6%、8.3%及び7.8%まで減少した。
上記結果は、SPSSパッケージプログラム(SPSS 12.0 for Windows(登録商標), USA)を利用して算出した。対照群と試験群と間の平均差に対する有意性はスチューデントt−検定を実施して検定した。有意水準はp<0.05とし、全ての測定値は平均値±標準誤差で表示している。
(1)実験動物及び実験デザイン
実験動物として28匹の雄性Sprague−Dawleyラット(5週齢、145±5g)を Orient Company (Korea) から購入した。ラットを1週間ペレット形態のLab−chow食に適応をさせた。正常群(NC)を除いた残りの肥満誘発群に高脂肪食を5週間不断給餌して肥満を誘発した後、正常群を含む4群(1群当たり7匹)に分け、5週間飼育した(図13に示されるように)。
飼育後、ラットを12時間絶食させた後、最初にエーテルで麻酔した。下大静脈から空腹時血液を採取した。採取した血液を3000×g、4℃で15分間遠心分離して、血清を分離した後、得られた血清を試料分析時まで−70℃で保管した。実験動物の臓器組織(肝臓、心臓、腎臓、精巣上体白色脂肪組織及び腎周囲白色脂肪組織)をPBS(リン酸緩衝生理食塩水)で数回洗浄した後、表面の水分を除去して秤量した。肝臓を、単離して収集し、液体窒素中で急冷した後、酵素活性の測定及び脂質定量のための試料分析時まで−70℃で保管した。肝臓、心臓及び腎臓の重量を測定した結果を下記表17に示している。精巣上体白色脂肪組織及び腎周囲白色脂肪組織の単位体重当たりの重さを測定した結果を図10に示している。
1)総コレステロール
血清総コレステロールの定量は、Allain らの文献(1974)の酵素法を適用して試験溶液(Asanpharm Co., Korea)を用いて実施した。血清コレステロールはCE(コレステロールエステル)及び遊離コレステロールの2形態で存在する。従って、CEと遊離コレステロールの両方を定量するために、CEをコレステロールエステラーゼにより脂肪酸と遊離コレステロールに変換した。このように変換した遊離コレステロールをコレステロールエステラーゼにより順にH2O2と△4−コレステノン(cholestenon)に変換した。H2O2をペルオキシダーゼ、フェノール及び4−アミノ−アンチピリンと混合して、赤色を発色させた後、500nmにおける吸光度を測定した。測定値をコレステロール標準溶液(300mg/dL)と比較して定量した。
血清中性脂質は、McGowan らの文献(1983)の酵素法に従って中性脂質測定用試薬(Asanpharm Co.,Korea)を用いて測定した。血清中の中性脂質をリポタンパク質リパーゼ(LPL)によりグリセロールと脂肪酸に分解した。グリセロールは、ATPとグリセロールキナーゼ(GK)の作用によりL−α−グリセロリン酸を形成した。L−α−グリセロリン酸のO2及びグリセロリン酸オキシダーゼ(GPO)との反応はH2O2を発生させた。そこに、ペルオキシダーゼと4−アミノ−アンチピリンを加えて赤色を発色させ、550nmにおける吸光度を測定した。測定値をグリセロール標準曲線と比較して定量した。
HDL−コレステロール含量はキットの試薬(AsanpharmCo., Korea)で測定した。LDL−コレステロールの含量は、下記のように Friedewald らの文献(1993)の方法に従って下記の通り計算した:
LDL−コレステロール=総コレステロール−HDL−コレステロール−(中性脂質/5)。
肝臓組織中の脂質含量の測定は、Folchらの文献の方法に従って行った。肝臓組織1gにCM溶液(クロロホルム:メタノール=2:1)を加えて、ホモジナイズした。溶液を12時間毎に振盪しながら、4℃で3日間保管した。3日後、水層から分離したCM溶液層をピペットで単離した後、80℃の水浴でCM溶液を完全に蒸発させて、乾燥脂質を得た。得られた乾燥脂質を無水エタノールに溶かし、ホモジナイズした後、中性脂質、総コレステロール及びHDL−コレステロールの含量をキットの試薬(AM157S−K、AM202−K、AM203−K、Asanpharm Co., Korea)で測定した。その結果を図12に示している。
上記の結果は、SPSSパッケージプログラムを用いて算出した。各群間の平均差に対する有意性は一元配置ANOVA(分散分析)で検定した。多群間の差については、p<0.05レベルでDuncan の多重範囲検定による事後検定を行った。その結果を平均値±S.E.で示している。
Claims (4)
- 共役リノール酸5〜50重量%、レシチン0.01〜5重量%、溶解補助剤としてエタノール0.01〜5重量%、補助乳化剤1〜15重量%、グリセリン10〜40重量%及び残量の水を含有してなる、水性ナノエマルジョン組成物。
- 粘度が1〜100センチポアズ(cP)である、請求項1に記載の組成物。
- 当該補助乳化剤が、ポリソルベート20、ポリソルベート80、アニオン性アミノ酸系乳化剤、糖エステル、コレステロール、ラウリル硫酸ナトリウム、ステアロイル乳酸ナトリウム及びグリセリンエステルよりなる群から選択される一つ又はそれ以上である、請求項1に記載の組成物。
- 当該アニオン性アミノ酸系乳化剤が、TEA−ココイルグルタミン酸塩、グルタミン酸ナトリウム、ココイルグルタミン酸ナトリウム、ココイルグルタミン酸マグネシウム及びラウロイルグルタミン酸ナトリウムよりなる群から選択される一つ又はそれ以上である、請求項3に記載の組成物。
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US8686039B2 (en) | 2014-04-01 |
EP2398450A4 (en) | 2012-08-08 |
EP2398450B1 (en) | 2015-04-01 |
KR100913689B1 (ko) | 2009-08-24 |
CN102271652A (zh) | 2011-12-07 |
WO2010095877A2 (en) | 2010-08-26 |
JP5259832B2 (ja) | 2013-08-07 |
US20120053241A1 (en) | 2012-03-01 |
WO2010095877A3 (en) | 2010-11-25 |
EP2398450A2 (en) | 2011-12-28 |
CN102271652B (zh) | 2013-09-18 |
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