JP2011500028A - 果汁の香味特性および鮮度指標の調節 - Google Patents
果汁の香味特性および鮮度指標の調節 Download PDFInfo
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- JP2011500028A JP2011500028A JP2010529039A JP2010529039A JP2011500028A JP 2011500028 A JP2011500028 A JP 2011500028A JP 2010529039 A JP2010529039 A JP 2010529039A JP 2010529039 A JP2010529039 A JP 2010529039A JP 2011500028 A JP2011500028 A JP 2011500028A
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- limonin
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- fruit juice
- juice
- isolimonin
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Abstract
Description
苦味は、消費者にとっての主な懸案事項である場合が多い。低レベルの苦味は、多くの消費者にジュースの官能特性および特徴への望ましい貢献を提供しうる。これらの消費者は、低レベルの苦味のピリッとした香味を楽しむ。しかしながら、ほとんどの消費者はまた、過剰な苦味が果汁の官能特性および特徴に悪影響を与え、消費するには不快にさせてしまうことも承知している。消費者はまた、苦味を濃縮果汁および/または低品質の果汁に伴う鮮度の欠如と結び付けて考えることが多い。
(1)リモニン、イソリモニン、および、微量のノミリン;
(2)ポリメトキシル化フラボン(PMF);および
(3)リモノイドβ−D−グルコピラノシド
の相互作用によって生じる。
HPLC装置は、2つのポンプ(Sykam S1122)、グラジエントミキサー(動的/静的グラジエントミキサー(Sunchrom社製))レオダイン・インジェクター(250μLループ)、オートサンプラー(Midas 380(Spark社製))、200〜600nmの波長範囲で溶出をモニタリングするダイオードアレイ検出器(SpectraFlow 600 DAD(Sunchrom社製))、分流モジュール(P−470目盛り付マイクロスプリッター(Upchurch社製))、および噴霧器(HPLC nebulizer,200μL/分〜2.5mL/分(S.E.D.E.R.E.社製))を備えた蒸発光散乱検出器(ELSD)(Sedex 85 LT−ELSD、p=2,6bar、T=40℃(S.E.D.E.R.E.社製))で構成された。
負(ESI-)または正のエレクトロスプレーイオン化(ESI+)モードで行うAPI 4000 LC−MS/MS(Applied Biosystems社(ドイツ国ダルムシュタット所在)製)に接続した、Agilent 1100 HPLC系を用いてLC−MS/MS解析を行った。スプレー電圧を−4500Vに設定し、窒素をカーテンガス(137.9Pa(20psi))として供給し、デクラスタリング電位を−65Vに設定した。多チャンネルの選択反応モニタリング(multiple reaction monitoring)(MRM)モードを用い、上述の質量転移を使用して化合物2および3を解析した。
Bruker社(ドイツ国ラインシュテッテン所在)製のDPX 400MHz NMRを使用して1H、COSY、HMQC、およびHMBCの分光実験を行った。内部標準としてのテトラメチルシランと共に、サンプルをDMSO−d6またはMeOD−d4に溶解し、測定前にNMR試料管(Schott Professional 178×5mm)に入れた。NMRソフトウェア Mestre−Cを用いてデータ分析を行った。
オレンジ種子(100g)を水、次いでアセトンで十分に洗浄し、液体窒素中で冷凍し、グラインディングミルで粉砕し、その後、60℃で4時間、メタノール(300mL)で2回抽出した。ろ過後、真空中で抽出液から溶媒を除去し、メタノール抽出物を非晶質の粉末として得た。
UV/VIS(アセトニトリル/水;pH2.5):λmax=220nm;
LC/MS(ESI+):m/z649([M−H]-);
LC/MS(ESI-):m/z668([M+NH4]+),673([M+Na]+),689([M+K]+);
1H NMR(400MHz,MeOD-d4,COSY):δ 0.66 [s, 3H, H-C(24)], 0.98 [s, 3H, H-C(25b)], 1.21 [s, 3H, H-C(25a)], 1.40 [s, 3H, H-C(18)], 1.66 [m, 1H, H-C(12)], 1.78 [m, 2H, H-C(11)], 1.99 [m, 1H, H-C(12)], 2.43 [dd, 1H, J=7.4, 22.1 Hz, H-C(6)], 2.55 [dd, 1H, J=5.6, 19.0 Hz, H-C(6)], 2.68 [d, 1H, J=4.3 Hz, H-C(9)], 2.71 [d, 2H, J=4.1 Hz, H-C(2)], 2.79 [dd, 1H, J=5.6, 14.7 Hz, H-C(5)], 2.94 [s, 1H, H-C(15)], 3.11 [m, 2H, H-C(2'), H-C(5')], 3.20 [m, 1H, H-C(4')], 3.27 [m, 1H, H-C(3')], 3.48 [m, 1H, H-C(6')], 4.20 [s, 1H, H-C(1)], 4.29 [d, 1H, J=7.6 Hz, H-C(1')], 4.40 [d, 2H, J=8.1 Hz, H-C(19)], 5.42 [s, 1H, H-C(17)], 6.53 [d, 1H, J=1.3 Hz, H-C(21)], 7.24 [s, 1H, H-C(23)], 7.63 [s, 1H, H-C(22)];
13C NMR(100MHz,MeOD−d4,HMQC,HMBC):δ 17.1 [C, C(11)], 18.4 [C, C(24)], 20.8 [C, C(25b)], 24.7 [C, C(18)], 26.8 [C, C(12)], 29.2 [C, C(25a)], 35.2 [C, C(2)], 36.4 [C, C(6)], 44.8 [C, C(13)], 45.1 [C, C(9)], 45.2 [C, C(10)], 50.7 [C, C(8)], 54.8 [C, C(5)], 59.8 [C, C(15)], 61.7 [C, C(6')], 63.8 [C, C(19)], 69.1 [C, C(14)], 70.4 [C, C(4')], 75.4 [C, C(2')], 76.0 [C, C(5')], 76.9 [C, C(3')], 78.1 [C, C(17)], 78.4 [C, C(1)], 80.8 [C, C(4)], 104.3 [C, C(1')], 112.3 [C, C(21)], 125.4 [C, C(20)], 140.3 [C, C(22)], 142.3 [C, C(23)], 173.0 [C, C(3), C(16)], 209.6 [C, C(7)]。
オレンジ果汁の貯蔵の間のリモニン−17−β−D−グルコピラノシドからのリモニンの想定される非酵素的放出を詳しく調べるため、搾りたてのオレンジ果汁のpH値(pH3.5)、またはオレンジ果汁濃縮物に見られるpH値の範囲(pH2.0および3.0)に調整したグルコピラノシド水溶液を、最長14週間、20℃の暗所で保持した。一定時間ごとに、モデル溶液から一定分量を取り出し、MRMモードで動作させたHPLC-MS/MSを使用して、グルコピラノシドから遊離されたリモニンの量について分析した。図2に示すように、モデル溶液のpH値とは独立して、保存期間が長くなるに従いリモニンが生成したが、pH値の低下は苦味化合物の生成に有利に働いた。例えば、pH2.0で維持した場合には0.85%molのリモニンがグルコピラノシドから遊離したのに対し、pH3.5ではわずか0.25%の苦味化合物しか生じなかった。
実施例2で同定し、図4に示された化合物4の化学構造を決定するため、pH1.5に調整したリモニン−17−β−D−グルコピラノシドの水溶液を60℃で4時間インキュベートし、分取用HPLCを使用して化合物4を単離および精製し、LC−MS/MSおよび1D/2D−NMRの実験によって、その化学構造を決定した。図5に示す1H NMRスペクトルでは、21のシグナルが観察され、そのうちδ1.44、1.72、2.00、2.25、2.66、2.66、2.73、2.75、2.91、および4.14ppmの化学シフトを示す10のシグナルは、リモニンのアルキルプロトンであるH−C(12a)、H−C(11)、H−C(12b)、H−C(6a)、H−C(2a)、H−C(5)、H−C(2b)、H−C(9)、H−C(6b)、およびH−C(1)の共鳴とかなり良好に調和していた。同種核(COSY)および異核相関実験(HMQC、HMBC)では、これらのシグナルの割り当ては明確には確認できなかった。4.51および4.78ppmにおいて共鳴するジアステレオ選択性のプロトンはメチレンのプロトンH−C(19)とよく一致しており、よってリモニンに存在するA環が原形を保っていることを示唆した。フランのプロトンであるH−C(21)、H−C(22)、およびH−C(23)についての6.62、7.60、および7.70ppmに見られる共鳴シグナルもまた、リモニンに対する構造的類似性を実証した。しかしながら化合物4は、H−C(15)、H−C(17)、およびH−C(18)のプロトンの化学シフトに、リモニンとの目立った差異を示した。H−C(17)のプロトンは、5.48ppm(3)から5.05ppm(4)への高磁場シフトを示したのに対し、H−C(15)とH−C(18)のプロトンは、それぞれ4.21ppmと1.11ppm(3)から4.50ppmと1.48ppm(4)への低磁場シフトを示した。加えて、2D−NMRの実験は、リモニン(3)の77.9/20.0ppm、および化合物4の85.1/27.1ppmで共鳴し、よって、化合物4の構造のC(17)位におけるリモニンのエピマー化を示唆する、C(17)/C(18)の化学シフトの差異を確認した。すべての分光分析データを考慮して、化合物4はリモニンのα−配向ではなく、C(17)位のフラン環のβ−配向を示し、初めてリモニンのC17−エピマーとして明確に同定された。C17−エピリモニンまたはイソリモニンと称される化合物4は、すでにリモニン−17−β−D−グルコピラノシドのヒト血漿代謝産物と推測されていたが、これは分光分析データに基づいた最初のリモニン・エピマーの構造確認であり、グルコピラノシドからの加水分解的単体分離を実証するものである。
UV/VIS(アセトニトリル/水;pH2.5)λmax=220nm;
LC/MS(ESI+)m/z509([M+K]+),493([M+Na]+),488([M+NH4]+);
LC/MS(ESI-):m/z469([M−H]-);
1H NMR(400MHz,DMSO−d6,COSY):δ 1.00 [s, 3H, H-C(24)], 1.02 [s, 3H, H-C(25b)], 1.11 [s, 3H, H-C(18)], 1.19 [s, 3H, H-C(25a)], 1.23 [m, 1H, H-C(12)], 1.73 [m, 2H, H-C(11)], 1.83 [m, 1H, H-C(12)], 2.27 [dd, 1H, J= 3.0, 14.7 Hz, H-C(6)], 2.46 [dd, 1H, J= 3.0, 15.7Hz, H-C(5)], 2.55 [m, 1H, H-C(9)], 2.62 [m, 1H, H-C(2)], 2.77 [d, 1H, J= 16.4 Hz, H-C(2)], 3.10 [t, 1H, J= 15.5 Hz, H-C(6)], 4.11 [m, 1H, H-C(1)], 4.12 [s, 1H, H-C(15)], 4.48 [d, 1H, J= 12.9 Hz, H-C(19)], 4.92 [d, 1H, J= 12.9 Hz, H-C(19)], 5.48 [s, 1H, H-C(17)], 6.51 [s, 1H, H-C(22)], 7.66 [s, 1H, H-C(21)], 7.72 [s, 1H, H-C(23)];
13C NMR(100MHz,MeOD−d4,HMQC,HMBC):δ 17.4 [C, C(24)], 18.1 [C, C(11)], 20.0 [C, C(18)], 20.4 [C, C(12)], 22.3 [C, C(25b)], 30.1 [C, C(25a)], 35.9 [C, C(2)], 36.5 [C, C(6)], 37.5 [C, C(13)], 45.7 [C, C(10)], 46.9 [C, C(9)], 50.5 [C, C(8)], 54.3 [C, C(15)], 58.2 [C, C(5)], 65.3 [C, C(19)], 67.4 [C, C(14)], 77.9 [C, C(17)], 78.9 [C, C(1)], 80.4 [C, C(4)], 110.9 [C, C(22)], 120.6 [C, C(20)], 141.9 [C, C(23)], 143.9 [C, C(21)], 168.7 [C, C(16)], 170.9 [C, C(3)], 208.5 [C, C(7)]。
UV/VIS(アセトニトリル/水;pH2.5)λmax=220nm;
LC/MS(ESI+)m/z509([M+K]+),493([M+Na]+),488([M+NH4]+);
LC/MS(ESI-):m/z469([M−H]-);
1H NMR(400MHz,DMSO−d6,COSY):δ 0.99 [s, 3H, H-C(24)], 0.99 [s, 3H, H-C(25b)], 1.19 [s, 3H, H-C(25a)], 1.44 [m, 1H, H-C(12)], 1.72 [m, 2H, H-C(11)], 2.00 [m, 1H, H-C(12)], 2.25 [dd, 1H, J= 3.7, 16.2 Hz, H-C(6)], 2.66 [m, 1H, H-C(2)], 2.66 [m, 1H, H-C(5)], 2.73 [m, 1H, H-C(2)], 2.75 [m, 1H, H-C(9)], 2.91 [t, 1H, J= 15.8 Hz, H-C(6)], 4.14 [d, 1H, J= 3.68 Hz, H-C(1)], 4.50 [s, 1H, H-C(15)], 4.51 [d, 1H, J= 13.2 Hz, H-C(19)], 4.78 [d, 1H, J= 13.2 Hz, H-C(19)], 5.05 [s, 1H, H-C(17)], 6.62 [s, 1H, H-C(22)], 7.60 [s, 1H, H-C(21)], 7.70 [s, 1H, H-C(23)];
13C NMR(100MHz,MeOD−d4,HMQC,HMBC):δ 18.3 [C, C(11)], 19.3 [C, C(24)], 22.1 [C, C(12)], 22.1 [C, C(25b)], 27.1 [C, C(18)], 30.6 [C, C(25a)], 36.6 [C, C(2)], 36.9 [C, C(6)], 40.3 [C, C(13)], 45.0 [C, C(9)], 45.1 [C, C(10)], 47.6 [C, C(8)], 56.3 [C, C(5)], 56.6 [C, C(15)], 65.4 [C, C(19)], 70.4 [C, C(14)], 79.1 [C, C(1)], 79.9 [C, C(4)], 85.1 [C, C(17)], 112.9 [C, C(22)], 122.4 [C, C(20)], 143.8 [C, C(21)], 144.2 [C, C(23)], 168.8 [C, C(16)], 170.5 [C, C(3)], 208.3 [C, C(7)]。
オレンジ果汁の保存の間のリモニンおよびイソリモニン/C17−エピリモニンの生成を研究するため、搾りたてのオレンジ果汁(pH3.5)を4℃および20℃で最長4週間保存し、その後、MRMモードを用いたHPLC−MS/MSによって、リモニンおよびイソリモニン/C17−エピリモニンを定量的に決定した。図7Aに示すように、オレンジ果汁中のリモニンの濃度は、保存の間に、搾りたての果汁の70.0μg/100gから4℃および20℃で2週間維持した場合の80μg/100gおよび85μg/100gにそれぞれ微増した。オレンジ果汁の貯蔵はC17−エピリモニンの濃度の増大も誘発し、例えば、4℃および20℃で4週間維持したサンプルでは、それぞれ、C17−エピリモニンの量の1.5倍または2倍の増大が見られた(図7B)。貯蔵誘発性のリモニン量の増大をイソリモニンのものと比較すると、オレンジ果汁の貯蔵においては、リモニンの形成がそのC17-エピマーよりも好ましいことが明らかに実証され、よって貯蔵の間に、ジュース中に存在するリモノエートA環ラクトンが酸触媒作用によって徐々にリモニンに転換されるという文献の研究結果を裏付けている。
これらのリモノイドの官能活性におけるC(17)の対掌性の影響を研究するため、リモニンおよびC17−エピリモニンについての苦味の閾値濃度を決定した。これらの官能評価は、C17−エピリモニンの苦味の閾値濃度が、リモニン(4.0μmol/L)について得られる値に近い10.0μg/L(水)であることを示し、よって両方のトリテルペノイド・ラクトン化合物の官能活性が似ていることを実証した。
Claims (17)
- 果汁の香味を調節する方法であって、
リモニン、イソリモニン、ノミリン、およびそれらの混合物からなる群より選択される化合物の前記果汁中の濃度を、それらの味覚閾値未満のレベルに調節する
工程を有してなる方法。 - ポリメトキシル化フラボンの濃度を、それらの味覚閾値未満のレベルに調節する工程をさらに有してなることを特徴とする請求項1記載の方法。
- 前記果汁の糖酸比を調節する工程をさらに有してなることを特徴とする請求項1または2記載の方法。
- 前記果汁のリモノイドβ−D−グルコピラノシドの濃度を調節する工程をさらに有してなることを特徴とする請求項1記載の方法。
- 前記果汁のリモノイドβ−D−グルコピラノシドの濃度を、それらの味覚閾値未満のレベルに調節する工程をさらに有してなることを特徴とする請求項4記載の方法。
- イソリモニン/リモニンの比が約0.25未満であることを特徴とする請求項1または2記載の果汁。
- 前記濃度が、逆浸透、イオン交換、蒸留、またはそれらの組合せからなる群より選択される技術によって調節されることを特徴とする請求項1記載の方法。
- 前記糖酸比が、リンゴ酸、クエン酸、およびそれらの混合物からなる群より選択される酸の濃度を低下させることによって調節されることを特徴とする請求項3記載の方法。
- 未処理果汁よりも少ない苦味を有する果汁であって、
前記果汁に含まれるリモニン、イソリモニン、ノミリン、およびそれらの混合物からなる群より選択される化合物の濃度が、前記化合物の味覚閾値の濃度未満である、果汁。 - ポリメトキシル化フラボンをさらに有してなることを特徴とする請求項9記載の果汁。
- リモノイドβ−D−グルコピラノシドをさらに有してなることを特徴とする請求項9記載の果汁。
- イソリモニン/リモニンの比が約0.25未満であることを特徴とする請求項9記載の果汁。
- 未処理の果汁よりも少ない苦味を有する、処理果汁であって、
前記処理果汁における、リモニン、イソリモニン、ノミリン、およびそれらの混合物からなる群より選択される化合物の濃度が、前記未処理の果汁における前記化合物の濃度よりも低い、果汁。 - 前記イソリモニン/リモニンの比が約0.25未満であることを特徴とする請求項13記載の処理果汁。
- 前記未処理の果汁における酸の濃度よりも低い、リンゴ酸、クエン酸、およびそれらの混合物からなる群より選択される酸の濃度を有することを特徴とする請求項13記載の処理果汁。
- 前記化合物の濃度がそれらの味覚閾値レベル未満であることを特徴とする請求項13または15記載の処理果汁。
- イソリモニンのリモニンに対する比を決定する工程を有してなる、果汁に与えた熱ストレスの量を決定する方法。
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JP2024509300A (ja) * | 2021-03-09 | 2024-02-29 | フイルメニツヒ ソシエテ アノニム | ヒドロキシおよびメトキシ置換フラボンならびにそれらの使用 |
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JP2016189721A (ja) * | 2015-03-31 | 2016-11-10 | ポッカサッポロフード&ビバレッジ株式会社 | レモン果汁含有飲料 |
JP2019216753A (ja) * | 2015-03-31 | 2019-12-26 | ポッカサッポロフード&ビバレッジ株式会社 | レモン果汁含有飲料 |
JP2019037166A (ja) * | 2017-08-24 | 2019-03-14 | アサヒ飲料株式会社 | 果汁含有飲料 |
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CN105029631A (zh) | 2015-11-11 |
CA2700417C (en) | 2014-10-28 |
RU2443128C2 (ru) | 2012-02-27 |
KR101283382B1 (ko) | 2013-07-08 |
EP2494874A1 (en) | 2012-09-05 |
RU2555580C2 (ru) | 2015-07-10 |
EP2494874B1 (en) | 2013-12-11 |
US20090175995A1 (en) | 2009-07-09 |
ES2428574T3 (es) | 2013-11-08 |
RU2011116763A (ru) | 2012-11-10 |
US8980352B2 (en) | 2015-03-17 |
CA2700417A1 (en) | 2009-04-16 |
KR101255530B1 (ko) | 2013-04-23 |
KR20120034232A (ko) | 2012-04-10 |
BRPI0817942A2 (pt) | 2014-10-07 |
ES2385784T3 (es) | 2012-07-31 |
EP2274991A2 (en) | 2011-01-19 |
RU2010118500A (ru) | 2011-11-20 |
CA2779595A1 (en) | 2009-04-16 |
EP2274991B1 (en) | 2012-05-30 |
MX2010003775A (es) | 2010-04-21 |
CA2779595C (en) | 2014-12-02 |
EP2217098A1 (en) | 2010-08-18 |
CN105029631B (zh) | 2018-04-17 |
EP2217098B1 (en) | 2013-08-07 |
JP5213960B2 (ja) | 2013-06-19 |
CN101820778A (zh) | 2010-09-01 |
WO2009049046A1 (en) | 2009-04-16 |
KR20100080549A (ko) | 2010-07-08 |
EP2274991A3 (en) | 2011-02-16 |
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