JP7008963B2 - 植物または微生物由来カロテノイド-酸素コポリマーの組成物、それを同定、定量および生成する方法ならびにその使用 - Google Patents
植物または微生物由来カロテノイド-酸素コポリマーの組成物、それを同定、定量および生成する方法ならびにその使用 Download PDFInfo
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- JP7008963B2 JP7008963B2 JP2018544057A JP2018544057A JP7008963B2 JP 7008963 B2 JP7008963 B2 JP 7008963B2 JP 2018544057 A JP2018544057 A JP 2018544057A JP 2018544057 A JP2018544057 A JP 2018544057A JP 7008963 B2 JP7008963 B2 JP 7008963B2
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- Prior art keywords
- carotenoid
- oxygen
- powder
- carotene
- ethyl acetate
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Description
様々な健康上の利益は、食餌カロテノイドに起因する1~3。α-およびβ-カロテンとβ-クリプトキサンチンとを含む、いくつかのプロビタミンAカロテノイドは、それらのビタミンA活性に関連した利益を提供する4。しかし、プロビタミンAカロテノイドと、ビタミンAに変換することができないその他のカロテノイドとの両方の、その他の非ビタミンAの利益は、説明することが容易でない5~7。
さらに、β-カロテンを含むカロテノイド、特にβ-カロテンの遍在性と、それらの公知の食品加工中に失われ易い性質により17、18、酸化、特に共重合が食品中で自然に生ずるのか否かおよびどの程度まで生ずるのか、ならびにこの損失の原因となり得るのかが、不明瞭である。
カロテノイド酸化生成物自体が有益な性質を有するのか、例えば非ビタミンAの健康上の利益を有するのか否か、かつ/または、それは、そのような利益を有する親カロテノイドおよびその抗酸化作用であるのか否かを決定することが求められている。さらに、動物の飼料、動物およびヒトの栄養補助食品、ならびに動物およびヒトの健康を増進することができる食品などの、製品を開発することが求められている。さらに、天然源(食品源、植物、または微生物など)から酸化カロテノイド生成物を開発するために、酸化カロテノイド生成物の供給源を同定することが求められている。さらに、そのような酸化カロテノイド生成物の経済的な供給源、およびそれを生成するための方法を、見出すことが求められている。
(a)カロテノイドを含有する供給源を選択することであり、一実施形態では、前記供給源が、食用植物源、または細菌、酵母菌、および藻類を含むがこれらに限定されない微生物源であること。一実施例では、供給源は、カロテノイドのレベルが高まるように遺伝子改変され、例えばゴールデンライスおよびM37W-Ph3コーン、ならびに遺伝子改変された微生物、例えば酵母、または「Plant carotenoids: genomics meets multi-gene engineering」Current Opinion in Plant Biology 2014年、19巻:111~117頁のG. Guilianoにより記載されるものである54;
(b)酸素への曝露、酸素に曝露される表面積の増加、酸素の分圧(ppO2)および/または温度の上昇、あるいは供給源中に存在するカロテノイド-酸素コポリマーのレベルを高める様式など、酸化重合条件下で供給源を加工すること;および
(c)カロテノイド-酸素コポリマーの供給源であるか否かを決定するために、前記加工された供給源からカロテノイド-酸素コポリマーを直接単離するもしくは同定することによって、かつ/または前記加工された供給源からカロテノイド-酸素コポリマーの指示物質を単離するもしくは同定することによって、カロテノイド-酸素コポリマーの量を定量すること。一部の実施形態では、供給源は、酸化によって、1~1000μg/g湿重量または10~10,000μg/g乾燥重量と同量のカロテノイド-酸素コポリマーを提供し得る、出発量のカロテノイドを有する。一部の実施形態では、10~10,000μg/g乾燥重量など、所望のカロテノイド-酸素コポリマーレベルをもたらす供給源が選択される。
(a)カロテノイドを含有する、または一部の実施形態ではカロテノイドに富む天然源、例えば微生物、または食用植物源、酵母、真菌、藻類、もしくは細菌を得ること。一部の実施形態では、天然源は、先に述べた植物および微生物から選択される;および
(b)前記供給源を、酸化重合条件下で加工すること。一部の実施形態では、前記条件は、空気または酸素への曝露、および、乾燥、粉末化、熱、光への曝露の増大、酸素の分圧(ppO2)および/または温度の上昇、あるいは酸化および/または存在するカロテノイド-酸素コポリマーのレベルを高める条件を促進させるその他の因子の1つまたは複数から選択される。
本発明は、例えば以下の項目を提供する。
(項目1)
カロテノイド-酸素コポリマーの供給源を同定する方法であって、
(a) カロテノイドを含有する食用植物源または微生物源を選択すること、
(b) 酸化重合条件下で前記供給源を加工すること、および
(c) カロテノイド-酸素コポリマーの供給源であるか否かを決定するために、前記加工された供給源から前記カロテノイド-酸素コポリマーを直接単離するもしくは同定することによって、かつ/または前記加工された供給源から前記カロテノイド-酸素コポリマーの指示物質を単離するもしくは同定することによって、前記カロテノイド-酸素コポリマーの量を定量すること
を含む方法。
(項目2)
前記供給源が、酸化によって、1~1000μg/g湿重量または10~10,000μg/g乾燥重量と同量のカロテノイド-酸素コポリマーを提供し得る、出発量のカロテノイドを有する、項目1に記載の方法。
(項目3)
前記酸化重合条件が、空気または酸素への曝露、および、乾燥、粉末化、熱、光への曝露の増大、酸素の分圧(ppO 2 )の上昇または酸化を促進させるその他の因子の1つまたは複数から選択される、項目1または2に記載の方法。
(項目4)
前記カロテノイド-酸素コポリマーの単離が、少なくとも1つの極性有機溶媒抽出/無極性溶媒沈殿サイクルを含む、項目1から3のいずれか一項に記載の方法。
(項目5)
前記溶媒が、一般に安全と認められる(GRAS)溶媒から選択される、項目4に記載の方法。
(項目6)
前記極性有機溶媒が酢酸エチルであり、前記無極性溶媒がヘキサンである、項目4または5に記載の方法。
(項目7)
前記同定する方法が、元素分析、GC-MS、GPC、およびFTIRの1つまたは複数から選択される、項目1から6のいずれか一項に記載の方法。
(項目8)
前記食用植物源が、植物もしくはその部分、種子、果実、または野菜である、項目1から7のいずれか一項に記載の方法。
(項目9)
前記食用植物源が、ニンジン、トマト、アルファルファ、スピルリナ、バラの実、甘唐辛子、チリペッパー、パプリカ、サツマイモ、ケール、ホウレンソウ、海藻、ウィートグラス、マリーゴールド、moringa oleifera、および赤ヤシ油からなる群から選択される、項目8に記載の方法。
(項目10)
前記カロテノイドがβ-イオノン環構造を有し、前記指示物質がゲロン酸である、項目1から9のいずれか一項に記載の方法。
(項目11)
前記カロテノイドが、ルテイン、カプサンチン、またはゼアキサンチンであり、前記指示物質が、4-ヒドロキシゲロン酸またはそのラクトンである、項目1から9のいずれか一項に記載の方法。
(項目12)
前記カロテノイドがルテインまたはゼアキサンチンである、項目11に記載の方法。
(項目13)
前記カロテノイドがリコペンまたはγ-カロテンであり、前記指示物質がゲラン酸である、項目1から9のいずれか一項に記載の方法。
(項目14)
前記カロテノイドがカンタキサンチンであり、前記指示物質が、2,2-ジメチルグルタル酸またはその無水物である、項目1から9のいずれか一項に記載の方法。
(項目15)
植物、藻類、真菌、種子、または微生物からなる群から選択される天然源から入手可能なカロテノイド-酸素コポリマーの量を増強する方法であって、
(a) カロテノイド生成を増強するために、前記天然源を遺伝子改変すること、および/または
(b) 前記天然源を、酸化重合条件下で加工すること
を含む方法。
(項目16)
カロテノイド-酸素コポリマーを含む生成物を調製する方法であって、
(a) カロテノイドを含む食用植物源または微生物源を得ること、および
(b) 前記供給源を、酸化重合条件下で加工すること
を含む方法。
(項目17)
前記酸化重合条件が、空気または酸素への曝露、および、乾燥、粉末化、熱、光への曝露の増大、酸素の分圧(ppO 2 )、温度の上昇、または酸化を促進させるその他の因子の1つまたは複数から選択される、項目15または16に記載の方法。
(項目18)
項目15から17のいずれか一項に記載の方法を使用して得られた前記生成物を、1つまたは複数の溶媒抽出/沈殿サイクルに供すること、そしてそこから前記カロテノイド-酸素コポリマー含有画分を回収することによって、前記カロテノイド-酸素コポリマー生成物を単離する方法。
(項目19)
少なくとも1つの極性有機溶媒抽出/無極性溶媒沈殿サイクルにおいて、前記溶媒が、一般に安全と認められる(GRAS)溶媒から選択される、項目18に記載の方法。
(項目20)
前記極性有機溶媒が酢酸エチルであり、前記無極性溶媒が低分子量炭化水素である、項目19に記載の方法。
(項目21)
前記低分子量炭化水素がヘキサンである、項目20に記載の方法。
(項目22)
前記食用植物源が、植物もしくはその部分、種子、果実、または野菜である、項目16から21のいずれか一項に記載の方法。
(項目23)
前記食用植物源が、ニンジン、トマト、アルファルファ、スピルリナ、バラの実、甘唐辛子、チリペッパー、パプリカ、サツマイモ、ケール、ホウレンソウ、海藻、ウィートグラス、マリーゴールド、moringa oleifera、および赤ヤシ油からなる群から選択される、項目22に記載の方法。
(項目24)
項目18から23のいずれか一項に記載の方法を使用して調製される生成物。
(項目25)
抽出/沈殿サイクル後に回収された前記生成物が、カロテノイド分解生成物を含まない、項目24に記載の生成物。
(項目26)
項目15から23のいずれか一項に従い調製されたカロテノイド-酸素ポリマーを含む生成物と、適切な賦形剤とを含む、組成物。
(項目27)
項目15から23のいずれか一項に従い単離された前記カロテノイド-酸素コポリマー生成物と、適切な賦形剤とを含む、組成物。
(項目28)
項目15から23のいずれか一項に記載の方法によって調製された前記カロテノイド-酸素コポリマーを含む生成物を含む、動物飼料または動物飼料用栄養補助食品。
(項目29)
項目15から23のいずれか一項に記載の方法によって調製されたカロテノイド-酸素コポリマーを含む生成物を含む、栄養補給食品または栄養補助食品。
(項目30)
カロテノイドを含む食品または栄養補助食品中の、カロテノイド-酸素コポリマーを増強するための方法であって、前記食品または栄養補助食品に、項目24または25に記載のカロテノイド-酸素コポリマー生成物を添加するステップを含む方法。
(項目31)
動物の免疫性を高めるための、項目24または25に記載のカロテノイド-酸素コポリマー生成物の使用。
(項目32)
動物の健康を増進させるための、項目24または25に記載の生成物を使用する単離されたカロテノイド-酸素コポリマーの有効量の使用。
(項目33)
前記動物の健康の増進が、先天性免疫を高め、抗炎症性を高め、免疫系の機能を高め、疾患に抵抗する動物の能力を高め、疾患から回復しもしくは克服し、または健康状態を維持することの、1つまたは複数から選択される、項目32に記載の使用。
(項目34)
前記動物がヒトである、項目31から33のいずれか一項に記載の使用。
(項目35)
項目15から23のいずれか一項に記載の方法を使用して調製された、項目31から33のいずれか一項に記載の使用のために一貫した所望量のカロテノイド酸素コポリマーを有する生成物。
(項目36)
ノルイソプレノイド副生成物を含まない、自然を供給源とするOxPVA組成物。
(項目37)
ノルイソプレノイド副生成物を含まない、自然を供給源とするOxCar組成物。
(項目38)
酸化重合条件下でカロテノイドを含む天然源を加工すること、それを1つまたは複数の溶媒抽出/沈殿サイクルに供すること、それから前記カロテノイド-酸素コポリマー含有画分を回収することから誘導された、項目36または37に記載の組成物。
(項目39)
前記天然源が、カロテノイド生成が増強されるように遺伝子改変されている、項目38に記載の組成物。
定義/略称
使用される略称:BHT、ブチル化ヒドロキシトルエン(2,6-ジ-tert-ブチル-4-メチルフェノール);GA、ゲロン酸;OxBC、完全酸化β-カロテン;OxLyc、完全酸化リコペン;OxLut、完全酸化ルテイン;OxCan、完全酸化カンタキサンチン;OxPVA、酸化プロビタミンAカロテノイド;PVA、プロビタミンAカロテノイド;SPE、固相抽出。
カロテノイド-酸素コポリマーの存在を評価するための間接的方法。
概説
方法
(a)供給源中に存在することが公知である純粋なカロテノイドを酸化すること、そして得られたカロテノイド-酸素コポリマー(付加生成物)と指示物質(反応の開裂生成物)との比を決定すること、そして時間、温度、圧力、供給源、出発材料の量、および酸素への曝露から選択される1つまたは複数の条件下で開裂生成物に対するカロテノイド-酸素コポリマーの較正曲線を作成すること;
(b)酸化条件下で供給源を加工すること、そして得られる指示物質(反応の開裂生成物)の量を同定および/または定量すること;および
(c)カロテノイド-酸素コポリマーのその存在または欠如を明らかにし、かつ/または源供給源中の、得られるカロテノイド-酸素コポリマーの量を決定するために、(b)の結果と、(a)の下で開発された較正曲線とを使用すること
を含む方法を提供する。
カロテノイド-酸素コポリマー生成物の単離
カロテノイド-酸素コポリマーの使用
材料および方法
材料
GA、GA-d6、および完全に酸化されたβ-カロテン(OxBC)、リコペン(OxLyc)、およびカンタキサンチン(OxCan)の調製について、記述してきた13。この研究では、完全に酸化されたルテイン(OxLut)を含む完全に酸化されたカロテノイドを、以下に述べるように68~70℃で調製した。SPEカートリッジは、Waters(Oasis MAX;500mg収着剤、6mL容量)から得た。シリカゲル(40~63μm)は、Silicycle Inc.(Quebec City、QC Canada)から購入し、シリカゲルTLCプレートは、Sigma-Aldrichから購入した。
設備
食品試料
68~70℃での完全酸化カロテノイドの調製
純粋なカロテノイドから得られた完全酸化カロテノイド化合物からのカロテノイド-酸素コポリマーの単離
(実施例2)
食品試料中のゲロン酸の分析、およびプロビタミンAカロテノイド-酸素コポリマー含量を推定するためのその使用
ゲロン酸分析
I/I6=a(m/m6)+b (1)
結果
食品試料中のGAの分析
プロビタミンAカロテノイド-酸素コポリマー含量の推定。
(実施例3)
カロテノイド-酸素コポリマー化合物の直接単離
カロテノイド-酸素コポリマーを単離するための手順。
結果
ニンジン粉末からのカロテノイド-酸素コポリマー化合物の直接単離。
その他の食品からのカロテノイド-酸素コポリマー化合物の単離
(実施例4)
リコペンおよびγ-カロテンの自動酸化のマーカーとしてのゲラン酸
(実施例5)
食品中のカロテン-酸素コポリマーの増強
実験設計
アッセイ方法
新鮮なニンジンのゲロン酸アッセイ
上部および底部を切り取った、新鮮な、皮を剥いたニンジンを濯ぎ、ペーパータオルで叩くように水気を取り、次いでフードプロセッサを使用して細かく細断した。ニンジン細片230~400gを1Lビーカーに入れ、その後、ゲロン酸-d6溶液0.4mL(メタノール中、0.001604mg/mL)、BHT(ブチル化ヒドロキシトルエン;4~5mg)、およびクロロホルム(CHCl3)(400~500mL)を入れた。混合物を20分間、13,500rpmで均質化し、次いでホモジナイザを止め、液体をビーカーに排出させ、ホモジナイザの内部および外部をCHCl3で濯いだ(合計で4×1.5mL)。全ての材料を2L分液漏斗に移し、橙色のCHCl3層を橙色のパルプから分離し、パルプをビーカーに戻した。CHCl3(300~400mL、2~4mgのBHTを含有)をパルプに添加し、5分間均質化した。CHCl3層を以前のように分離し、CHCl3抽出物を合わせ、溶媒をロータリーエバポレーターで蒸発させた。CHCl3を添加して(15mL)、残留物を溶解し、混合物を乾燥し(MgSO4)、綿に通して濾過し、CHCl3(合計で15mL)で濯いだ。水性KOH(25mL;約90mgのKOHを50mLの水に溶解することによって調製された)をCHCl3溶液に添加し、5分間激しく撹拌した。混合物を分液漏斗に移し、CHCl3のほとんどを除去し、残りの液体を5分間遠心分離した。水性層を分離し、酸性化し(1M HClを約3mL)、CHCl3で抽出した(2×15mL)。合わせた抽出物を乾燥し(Na2SO4)、濾過し、溶媒を蒸発させた。残留物をメタノール(9mL)に溶解し、固体NaHCO3(約0.1g)を添加し、混合物を撹拌した。水性NaHCO3(1mL、1M)を添加し、その後、Me3OBF4(約0.3g)を添加した。15分撹拌した後、9mLの水(H2O)を添加し、撹拌し、混合物をジクロロメタン(CH2Cl2)で抽出した(2×7.5mL)。合わせたCH2Cl2抽出物をNa2SO4で乾燥し、綿に通して濾過し、溶媒を、ロータリーエバポレーターで、室温で慎重に蒸発させた。残留物を0.2mLのアセトニトリルに溶解し、1μLをGC-MSに注入した(スプリットレス注入、SIMモードモニタリングイオン154.1および160.1)。
乾燥したニンジンピューレまたは粉末のゲロン酸アッセイ
乾燥したニンジンピューレまたは粉末のβ-カロテンアッセイ
結果および考察
(実施例6)
ルテイン、ゼアキサンチン、およびカプサンチンの自動酸化の、4-ヒドロキシゲロン酸およびそのラクトンマーカー。
(実施例7)
カンタキサンチンの自動酸化の2,2-ジメチルグルタル酸およびその無水物マーカー
表
** n.d. -決定されず
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Claims (8)
- カロテノイド-酸素コポリマーを含む生成物を調製する方法であって、
(a) カロテノイドを含む供給源であって、
(i)細菌、酵母、真菌、もしくは藻類から選択される微生物源、または
(ii)ニンジン、トマト、アルファルファ、スピルリナ、バラの実、甘唐辛子、チリペッパー、パプリカ、サツマイモ、ケール、ホウレンソウ、海藻、ウィートグラス、マリーゴールド、moringa oleifera、および赤ヤシ油から選択される食用植物源、から選択される供給源を、酸化重合条件下で加工し、前記カロテノイド-酸素コポリマーを含む混合物を形成すること
(b)前記混合物を少なくとも一つの極性有機溶媒と合わせ、前記カロテノイド-酸素コポリマーを含む溶液を形成すること
(c)前記溶液に無極性溶媒を添加し、前記カロテノイド-酸素コポリマーを含む沈殿物を形成すること、および
(d)前記沈殿物を単離し、前記カロテノイド-酸素コポリマーを含む前記生成物を形成すること
を含む方法。 - 前記酸化重合条件が、空気または酸素への曝露、および、乾燥、粉末化、熱、光への曝露の増大、酸素の分圧(ppO2)、温度の上昇、または酸化を促進させるその他の因子の1つまたは複数から選択される、請求項1に記載の方法。
- 前記酸化重合条件が、乾燥および粉末化、ならびに空気または酸素への曝露である、請求項2に記載の方法。
- 前記無極性溶媒が低分子量炭化水素である、請求項1に記載の方法。
- 前記低分子量炭化水素がヘキサン、ペンタン、またはヘプタンである、請求項4に記載の方法。
- カロテノイドを含む前記供給源がニンジンまたはトマトから選択される、請求項1に記載の方法。
- 工程(a)の加工により、前記混合物中に1~1000μg/g湿重量または10~10,000μg/g乾燥重量のカロテノイド-酸素コポリマーが提供される、請求項1に記載の方法。
- 前記極性有機溶媒が、酢酸エチル、酢酸ブチル、またはメタノールである、請求項1に記載の方法。
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CN110596263B (zh) * | 2019-08-23 | 2022-06-14 | 广州泽力医药科技有限公司 | 一种辣木提取物指纹图谱的建立方法及其指纹图谱 |
CN110672769A (zh) * | 2019-10-27 | 2020-01-10 | 贵州省兽药饲料监察所(贵州省兽药残留监测中心) | 一种测定禽蛋中斑蝥黄色素残留量的方法 |
CN111296646A (zh) * | 2020-02-24 | 2020-06-19 | 华南农业大学 | 一种提高母猪乳中抗体的复合预混料及其应用 |
CN112243631B (zh) * | 2020-09-14 | 2022-03-22 | 云南省农业科学院花卉研究所 | 一种快速打破绿花百合籽鳞茎休眠的方法 |
KR102609727B1 (ko) * | 2021-12-14 | 2023-12-05 | 주식회사 바이오메딕 | 감귤류 카로티노이드 함량 예측용 프라이머 세트 및 이의 용도 |
CN114304397B (zh) * | 2022-01-12 | 2023-10-27 | 中国科学院东北地理与农业生态研究所 | 一种干玉米秸秆与全株小麦草混贮饲料的制备方法 |
CN114262471B (zh) * | 2022-01-19 | 2023-03-21 | 深圳大学 | 细菌纤维素复合凝胶及其制备方法与应用 |
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JP2019515247A (ja) | 2019-06-06 |
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EP3420004A1 (en) | 2019-01-02 |
WO2017143460A1 (en) | 2017-08-31 |
KR20180115283A (ko) | 2018-10-22 |
KR102454311B1 (ko) | 2022-10-14 |
US20190054135A1 (en) | 2019-02-21 |
EP3420004A4 (en) | 2019-10-23 |
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