JP2021527433A - Dhaを濃縮した多価不飽和脂肪酸組成物 - Google Patents
Dhaを濃縮した多価不飽和脂肪酸組成物 Download PDFInfo
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Abstract
【選択図】図1
Description
(i)組成物の総脂肪酸含有量の少なくとも約86重量%の量のドコサヘキサエン酸(22:6n−3)と、
(ii)組成物の総脂肪酸含有量の少なくとも約3重量%の量の第2の多価不飽和脂肪酸であって、組成物中で2番目に豊富な多価不飽和脂肪酸である、第2の多価不飽和脂肪酸と、を含み、
ドコサヘキサエン酸および第2の多価不飽和脂肪酸が、各々独立して、脂肪酸、脂肪酸塩、脂肪酸エステル、または脂肪酸エステルの塩の形態で提供される、野菜ベースの脂質組成物が提供される。
(i)組成物の総脂肪酸含有量の少なくとも約86重量%の量のドコサヘキサエン酸(22:6n−3)と、
(ii)組成物の総脂肪酸含有量の少なくとも約3重量%の量の第2の多価不飽和脂肪酸であって、組成物中で2番目に豊富な多価不飽和脂肪酸である、第2の多価不飽和脂肪酸と、
(iii)組成物の総脂肪酸含有量の約0.1重量%〜約4重量%の量のα−リノレン酸(18:3n−3)と、を含み、
ドコサヘキサエン酸、第2の多価不飽和脂肪酸、およびα−リノレン酸が、各々独立して、脂肪酸、脂肪酸塩、脂肪酸エステル、または脂肪酸エステルの塩の形態で提供される。
(i)組成物の総脂肪酸含有量の少なくとも約86重量%の量のドコサヘキサエン酸(22:6n−3)と、
(ii)組成物の総脂肪酸含有量の少なくとも約3重量%の量のエイコサテトラエン酸(20:4n−3)であって、組成物中で2番目に豊富な多価不飽和脂肪酸である、エイコサテトラエン酸と、
(iii)組成物の総脂肪酸含有量の約0.1重量%〜約4重量%の量のα−リノレン酸(18:3n−3)と、を含み、
ドコサヘキサエン酸、エイコサテトラエン酸、およびα−リノレン酸が、各々独立して、脂肪酸、脂肪酸塩、脂肪酸エステル、または脂肪酸エステルの塩の形態で提供される。
当技術分野で日常的に実施されている技術を使用して、植物および種子によって生成された油を抽出、加工、および分析することができる。典型的には、植物の種子は調理され、圧搾され、油が抽出され、原油を生成する。その油は、次に、脱ガム、精製、漂白、および/または脱臭することができる。脱ガム、精製、漂白、および脱臭の組み合わせは、DHAが豊富な脂質混合物を調製するために特に効果的であることが見出されている。したがって、一実施形態では、脂質組成物は、脱ガム、精製、漂白、および/または脱臭された種子油から得られる。しかしながら、このように油を加工する必要はなく、これらの方法を用いずに、適切な純化および濃縮が達成され得る。
本明細書で使用される場合、本発明の脂質または油に関連して使用される場合の「純化された」という用語は、典型的には、抽出された脂質または油が脂質/油成分の純度を高めるために1つ以上の加工ステップに供されたことを意味する。例えば、純化ステップは、抽出された油の脱ガム、脱臭、脱色、または乾燥のうちの1つ以上を含み得る。しかしながら、本明細書で使用される場合、「純化された」という用語は、総脂肪酸含有量のパーセンテージとしてDHA含有量を増加させるために、エステル交換プロセス、または本発明の脂質または油の脂肪酸組成を変更する別のプロセスを含まない。言い換えると、純化された脂質または油の脂肪酸組成は、未純化の脂質または油の脂肪酸組成と本質的に同じである。
原油は通常、トリアシルグリセロール(TAG)の形態で目的の脂肪酸を含有する。エステル交換とは、TAG内およびTAG間で脂肪酸を交換するために、または脂肪酸を別のアルコールに転移しエステル(エチルエステルやメチルエステルなど)を形成するために使用できるプロセスである。本発明の実施形態において、エステル交換は、典型的には触媒として強酸または強塩基を含む化学的手段を使用して達成される。ナトリウムエトキシド(エタノール中)は、エステル交換によって脂肪酸エチルエステルを形成するために使用される強塩基の例である。このプロセスは、周囲温度または高温(例えば、最大約80℃)で実施することができる。
分子蒸留は、飽和脂肪酸などの揮発性の高い成分を原油から大量に除去するための効果的な方法である。蒸留は、典型的には、減圧下、例えば約1mbar未満で実施される。次に、温度および時間は、数時間(例えば、1〜10)の蒸留時間の後に、蒸留物と残留物との間で約50:50の分割を達成するように選択され得る。本発明の脂質組成物の生成に使用される典型的な蒸留温度は、120℃〜180℃の範囲、特に145℃〜160℃である。
クロマトグラフィーは、LC−PUFA混合物の様々な成分を分離するための効果的な方法である。それは、混合物中の1つ以上の好ましいLC−PUFAの濃度を増加させるために使用され得る。クロマトグラフィー分離は、様々な条件下で達成することができるが、典型的には、固定床クロマトグラフィーシステムまたはシミュレートされた移動床システムを使用することを含む。
本発明の脂質組成物は、医薬品有効成分(API)として、またはさらなる濃縮によってそこから得ることができるAPIの前駆体(または「中間体」)として、有用である。このような組成物は、DHAおよび/またはALAなどの有益なPUFAのレベルでさらに濃縮される。
本発明の脂質組成物は、バルク油である。すなわち、脂質組成物は、脂質の一部または全部が得られた原料(例えば、植物の種子)から分離されている。
米国特許公開第US2018/0016590A1号に開示されている品種のキャノーラは夏作物として栽培された。種子を収穫した後、粉砕前は室温で保存した。
純粋な魚油には、低レベルのALA脂肪酸、ならびに有意に高レベルのEPAおよびDHAが含有される。参照油ブレンド(本明細書では「粗トリグリセリド参照ブレンド油」または同様のものと呼ぶ)は、実施例1で得られた濾過されたDHAキャノーラ油と組成が可能な限り類似するように設計された。これは、(a)DHAの総レベルをDHAキャノーラ油のレベルと一致させ、(b)DHA/(ALA+EPA)の比率を一致させることによって行われた。これは、DHA(マグロ)が豊富な魚油、ALA(亜麻仁油)が豊富な油、および標準的なキャノーラ油をブレンドすることによって達成された。得られた参照ブレンド油も、DHAキャノーラ油と同様の総オメガ−3含有量を有する。
ランシマット安定性研究は、それぞれ実施例1および実施例2に記載されている粗DHAキャノーラ油および参照ブレンドを使用して実施された。この方法では、Metrohm743 Rancimatの標準的手順を90℃で使用して、約2.5gの試験材料を試験することを伴った。
機械的攪拌機を備えた乾燥した窒素フラッシュBuchi CR101化学反応器に、無水エタノール(12.5L)および実施例1で得られた粗トリグリセリドキャノーラ油(「DHAキャノーラ油」)(5.00kg)を加え、混合物を撹拌した。
機械的攪拌機を備えた乾燥した窒素フラッシュBuchi CR101化学反応器に、無水エタノール(12.5L)および実施例2に従って得られた粗トリグリセリド参照ブレンド油(5.00kg)を加え、混合物を撹拌した。
エステル交換手順は、5.17kgの参照の粗ブレンド油で実施した。得られた粗反応混合物に、石油スピリット(15L)および水(3.3L)を加え、完全に混合しながら、混合物を10%塩酸(合計910mLが必要)でpH7に慎重に酸性化した。
真空蒸留により脂肪酸エチルエステル(FAEE)混合物のより揮発性の高い成分を除去するための標準的手順
粗キャノーラ−DHA(実施例5で得られた)からの粗脂肪酸エチルエステル(FAEE)を、以下の条件下で蒸留に供した。蒸留による分離は、蒸留物および残留物を収集する2x1000mlの収集フラスコを備え、真空下にあるPope2インチ(50mm)薄膜蒸留器にトランスエステル化原油を通過させることによって達成された。各々の脂肪酸組成を分析した。
参照の粗ブレンド(実施例6で得られた)からの粗脂肪酸エチルエステル(FAEE)を、前の実施例に示したのと同じ条件下で蒸留に供した。
分取HPLC
実施例7で得られた(すなわち、粗キャノーラ−DHAから得られ、エステル交換および蒸留を使用して処理された)脂肪酸エチルエステル(FAEE)を、以下の条件下でクロマトグラフィー分離に供した。Waters Prep4000システム、10mlのループのRheodyneインジェクター、300×40mmのDeltaprep C18カラム、Waters2487デュアル波長検出器、およびチャートレコーダーを備える分取HPLCシステムを、88%のメタノール/水移動相で、70mL/分で平衡化した。検出器は、215nmおよび2.0吸光度単位のフルスケールに設定し、チャートは、6cm/時間で実行した。
試料分析には、Waters600Eポンプコントローラー、717オートサンプラー、2996フォトダイオードアレイ検出器、および2414屈折率検出器を備えるHPLCシステムを使用した。分析は、移動相としてアイソクラティックの90%のメタノール/水または95%のメタノール/水のいずれかを1.0mL/分で使用して、150×4.6mmのAlltimaC18カラム上で実施した。データの収集および処理は、Waters Empower3ソフトウェアで実施した。
参照ブレンド(実施例8で得られた)の蒸留された脂肪酸エチルエステル(FAEE)を、前の実施例に示したのと同じ条件下でクロマトグラフィー分離に供した。
ヘッドスペースGC−MS安定性試験
特定の条件下で放出されるプロパナールの量を評価するために、上記の濃縮製品に対してヘッドスペース分析を実行した。プロパナール放出のレベルの増加は、試験材料の安定性の低下を示している。
65μm PDMS/DVB StableFlexファイバー(Supelcoファイバーキット57284−u)を選択した。
ファイバーは、Triplus RSHコンディショニングステーションで、250℃で使用する前に、10分間コンディショニングした。
抽出前に試料を40℃で1分間インキュベートした。
Headspaceバイアルから1分間抽出した。
広範囲の揮発性成分を捕捉できる優れた一般的な方法であることが期待される。
Thermo Scientific TRACE1310 GC
Thermo Scientific TR−DIOXIN 5MSカラム、内径0.25mm、30mフィルム0.1μm
の分割噴射250℃分割83、1.2mlのHe/分
GCランプ:5℃/分で40℃、1分〜100、次に50℃/分で300℃まで
Thermo Scientific DFS高分解能GC−MS
低分解能(1000)、フルスキャン35−350Da、0.5秒/スキャン
標準:−プロパナールおよびヘキサナールの標準希釈液は、供給されたDHAキャノーラエチルエステルに作製された。次に、これらの標準混合物を540μlの容量で20mlのヘッドスペースバイアルに添加した。
以下の表に、T=0〜2日間で、実施例9で得られたキャノーラ油および実施例10で得られた参照油から得られた結果をまとめる。試験試料は、この期間中、ライトボックス上および蛍光管照明下で、周囲温度で保持された。m/z58分子イオンを分析し、質量クロマトグラムは室温で1.37分にプロパナールの出現を明確に示す。下の表でプロパナールの展開を定量化し、データを図1に示す。DHAキャノーラ油は実質的に少量のプロパナールを放出し、参照と比較してキャノーラ油の安定性が改善されていることを論証する。
実施例1で得られたキャノーラ油の一部は、さらなる濃縮を受ける前に精製された。精製プロセスには、脱ガム、アルカリ精製、漂白、および脱臭が含まれた。
脱ガムとは、油から非水和性および水和性のリン脂質を除去することである。実施例1で得られた乾燥粗油を53±2℃に加熱し、0.2%の50%のクエン酸溶液を加えた。約30分間混合した後、2.0%の加熱(53±2℃)軟水を加え、約30分間混合した。保持中に油を67±3℃に加熱し、次に遠心分離した。
精製とは、腐食剤で鹸化して水溶性にした後の遊離脂肪酸の除去、およびそれに続く遠心分離による除去である。ホスファチドの水和を継続するために、酸前処理ステップが使用された。脱ガム油を65±5℃に加熱し、0.1%の85%のリン酸を添加し、合計30分間混合した。酸の添加および保持時間の後、20 Be’(Baume; 14.4%、w/w)水酸化ナトリウムを添加し、遊離脂肪酸と0.05%(w/w)過剰を中和した。次に、腐食剤および油をさらに15分間混合した。15分間保持しながら油を62±2℃に加熱した後、油を遠心分離した。
石鹸をさらに除去するために、漂白に適合するレベルまでTrisylシリカ処理を実施した。Trisyl前処理は、漂白ステップと組み合わされた。精製油を68±5℃に加熱し、0.3%のTrisyl300で処理した。油/Trisylを約15分間混合した後、漂白を続けた。
精製油は、過酸化物、リン脂質、カラーボディー、および微量の石鹸を除去するために吸着粘土で処理された。ホスファチドの水和を継続するために、酸前処理ステップが使用された。Trisyl前処理油を0.2%(w/w)の50%クエン酸溶液と混合した。15分間混合した後、2%(w/w)のTonsil Supreme126FF漂白粘土を添加した。次に、混合物を真空下で90±2℃に加熱し、約30分間保持した。油を60±2℃に冷却し、窒素で真空破壊し、1.0kgの濾過助剤を加えて濾過した。圧力容器:500LのCherry−Burrell圧力容器、蒸気または冷却水ジャケット、混合用のインペラーおよびバッフルを備えた全て316ステンレス構造、製造シリアル番号E−227−94。フィルタープレス:24´´Polypropylene Sperry Filter Press、容量4.8cuのftフィルター、紙および布の支持材を使用した。
漂白された油は、高温および低圧で蒸気を用いて散布され、臭気成分、フレーバー成分、および追加の遊離脂肪酸が除去された。高温での熱漂白によっても色が落ちる。漂白油の半分を180±2℃で60分間、1%のスパージ蒸気で脱臭し、脂肪酸組成(FAC)を監視した。脱臭容器(OD4):400L Coppersmithing真空定格容器、蒸気または冷却水ジャケット、全て316ステンレス構造。180℃で60分間保持すると、DHAレベルのわずかな低下が観察された。次に、180℃で30分間保持して別の試験を実行した。生成物は、窒素下で20LのプラスチックHDPEペール缶に梱包し、4℃のクーラーに保管した。
実施例2に記載されている参照ブレンドの一部は、さらに濃縮される前に精製された。精製プロセスでは、前の実施例に示したのと同じ条件下で、参照ブレンドを精製した。
機械的攪拌機を備えた乾燥した窒素フラッシュBuchi CR101化学反応器に、無水エタノール(12.5L)および実施例13で得られた精製(「RBD」)トリグリセリドキャノーラ−DHA油(5.00kg)を加え、混合物を撹拌した。
機械的攪拌機を備えた乾燥した窒素フラッシュBuchi CR101化学反応器に、無水エタノール(12.5L)および実施例14に従って得られたRBDトリグリセリド参照ブレンド油(約5kg)を加え、混合物を撹拌した。
エステル交換手順は、約5kgのRBD参照ブレンド油で実施された。得られた粗反応混合物に、石油スピリット(15L)および水(3.3L)を加え、完全に混合しながら、混合物を10%塩酸(合計910mLが必要)でpH7に慎重に酸性化した。
真空蒸留により脂肪酸エチルエステル(FAEE)混合物のより揮発性の高い成分を除去するための標準的手順
RBDキャノーラ−DHA(実施例16で得られた)からの脂肪酸エチルエステル(FAEE)を、以下の条件下で蒸留に供した。蒸留による分離は、蒸留物および残留物を収集する2x1000mlの収集フラスコを備え、真空下にあるPope2インチ(50mm)薄膜蒸留器にトランスエステル化原油を通過させることによって達成された。各々の脂肪酸組成を分析した。
RBD参照ブレンド(実施例17で得られた)からの脂肪酸エチルエステル(FAEE)を、前の実施例に示したのと同じ条件下で蒸留に供した。
実施例18で得られた(すなわち、RBDキャノーラ−DHAから得られ、エステル交換および蒸留を使用して処理された)脂肪酸エチルエステル(FAEE)を、以下の条件下でクロマトグラフィー分離に供した。Waters Prep4000システム、10mlのループのRheodyneインジェクター、300×40mmのDeltaprep C18カラム、Waters2487デュアル波長検出器、およびチャートレコーダーを備える分取HPLCシステムを、88%のメタノール/水移動相で、70mL/分で平衡化した。検出器は、215nmおよび2.0吸光度単位のフルスケールに設定し、チャートは、6cm/時間で実行した。
RBD参照ブレンド(実施例19で得られた)の蒸留された脂肪酸エチルエステル(FAEE)を、前の実施例に示したのと同じ条件下でクロマトグラフィー分離に供した。
ヘッドスペース分析は、実施例12に記載された方法に従って、実施例20および実施例21に記載された濃縮生成物について実行した。
Claims (16)
- 野菜ベースの脂質組成物であって、
(i)前記組成物の総脂肪酸含有量の少なくとも約86重量%の量のドコサヘキサエン酸(22:6n−3)と、
(ii)前記組成物の総脂肪酸含有量の少なくとも約3重量%の量の第2の多価不飽和脂肪酸であって、前記組成物中で2番目に豊富な多価不飽和脂肪酸である、第2の多価不飽和脂肪酸と、を含み、
前記ドコサヘキサエン酸および前記第2の多価不飽和脂肪酸が、各々独立して、脂肪酸、脂肪酸塩、脂肪酸エステル、または脂肪酸エステルの塩の形態で提供される、野菜ベースの脂質組成物。 - ドコサヘキサエン酸(22:6n−3)が、前記組成物の総脂肪酸含有量の少なくとも約87重量%(例えば、最大約96重量%)の量で存在する、請求項1に記載の脂質組成物。
- 前記組成物中のドコサヘキサエン酸対エイコサペンタエン酸の重量比が、少なくとも50:1である、請求項1または請求項2に記載の脂質組成物。
- 前記第2の多価不飽和脂肪酸が、少なくとも4つの不飽和を含むC:20−24のオメガ−3多価不飽和脂肪酸である、請求項1〜3のいずれか一項に記載の脂質組成物。
- 前記第2の多価不飽和脂肪酸が、前記組成物の総脂肪酸含有量の約3重量%〜約12重量%の量で存在する、請求項1〜4のいずれか一項に記載の脂質組成物。
- 前記野菜ベースの脂質組成物が、前記組成物の総脂肪酸含有量の約0.1重量%〜約4重量%(例えば、約0.5量%〜約2重量%)の量のα−リノレン酸(18:3n−3)をさらに含む、請求項1〜5のいずれか一項に記載の脂質組成物。
- 前記ドコサヘキサエン酸、前記第2の多価不飽和脂肪酸、および前記α−リノレン酸(存在する場合)が、各々独立して、脂肪酸エステルもしくは脂肪酸エステルの塩の形態で、例えば、脂肪酸エチルエステルの形態で、またはトリグリセリドの一部として提供される、請求項1〜6のいずれか一項に記載の脂質組成物。
- 前記組成物中のパルミチン酸の量が、前記組成物の総脂肪酸含有量の約0.5重量%未満である、請求項1〜7のいずれか一項に記載の脂質組成物。
- 前記脂質組成物が、単一の供給源に由来する、請求項1〜8のいずれか一項に記載の脂質組成物。
- 前記脂質組成物が、植物に由来する、請求項1〜9のいずれか一項に記載の脂質組成物。
- 前記植物が、油糧種子、特に、Brassica sp.、Gossypium hirsutum、Linum usitatissimum、Helianthus sp.、Carthamus tinctorius、Glycine max、Zea mays、Arabidopsis thaliana、Sorghum bicolor、Sorghum vulgare、Avena sativa、Trifolium sp.、Elaesis guineenis、Nicotiana benthamiana、Hordeum vulgare、Lupinus angustifolius、Oryza sativa、Oryza glaberrima、Camelina sativa、またはCrambe abyssinicaである、請求項10に記載の脂質組成物。
- 前記脂質組成物が、脱ガム、精製、漂白、および/または脱臭された種子油から得られる、請求項10または請求項11に記載の脂質組成物。
- 前記組成物が、錠剤、カプセル、カプセル化ゲル、摂取可能な液体もしくは粉末、乳濁液、または局所軟膏もしくはクリームの形態で提供される、請求項1〜12のいずれか一項に記載の脂質組成物。
- 抗酸化剤、安定剤、および界面活性剤からなる群から選択される1つ以上の追加成分をさらに含む、請求項1〜13のいずれか一項に記載の脂質組成物。
- 心血管疾患の治療もしくは予防、心血管疾患患者の死亡に対する防御、全体的な血清コレステロールレベルの低下、高血圧の低下、HDL:LDL比の増加、トリグリセリドの低下、またはアポリポタンパク質Bレベルの低下に使用するための、請求項1〜14のいずれか一項に記載の脂質組成物。
- 請求項1〜14のいずれか一項に記載の脂質組成物を生成するためのプロセスであって、脂肪酸エチルエステルの混合物を提供することと、前記混合物をクロマトグラフィー分離プロセスに供することと、を含み、任意選択で、前記脂肪酸エチルエステルの混合物が、野菜ベースの脂質油のエステル交換および蒸留によって得られる、プロセス。
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JP7345511B2 (ja) | 2023-09-15 |
BR112020026051A8 (pt) | 2023-02-28 |
US20240130993A1 (en) | 2024-04-25 |
EP3809861A1 (en) | 2021-04-28 |
WO2019242873A1 (en) | 2019-12-26 |
AR113674A1 (es) | 2020-05-27 |
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