JP5463526B2 - Dried defatted cereal meal with adsorbed and concentrated health functional ingredients, concentrate of health functional ingredients prepared from the meal, and methods for producing them - Google Patents

Dried defatted cereal meal with adsorbed and concentrated health functional ingredients, concentrate of health functional ingredients prepared from the meal, and methods for producing them Download PDF

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JP5463526B2
JP5463526B2 JP2008073390A JP2008073390A JP5463526B2 JP 5463526 B2 JP5463526 B2 JP 5463526B2 JP 2008073390 A JP2008073390 A JP 2008073390A JP 2008073390 A JP2008073390 A JP 2008073390A JP 5463526 B2 JP5463526 B2 JP 5463526B2
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polar
oryzanol
cereal meal
tocopherol
health functional
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JP2009225702A (en
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秀樹 潮
玲子 長阪
和幸 大原
亜実 寺島
武 福森
繁晴 金本
敬士 若林
裕之 前原
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Satake Corp
Tokyo University of Marine Science and Technology NUC
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Tokyo University of Marine Science and Technology NUC
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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K50/00—Feeding-stuffs specially adapted for particular animals
    • A23K50/80—Feeding-stuffs specially adapted for particular animals for aquatic animals, e.g. fish, crustaceans or molluscs
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/111—Aromatic compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/105—Plant extracts, their artificial duplicates or their derivatives
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/15—Vitamins
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L7/00—Cereal-derived products; Malt products; Preparation or treatment thereof
    • A23L7/10—Cereal-derived products
    • A23L7/101—Addition of antibiotics, vitamins, amino-acids, or minerals
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L7/00—Cereal-derived products; Malt products; Preparation or treatment thereof
    • A23L7/10—Cereal-derived products
    • A23L7/115—Cereal fibre products, e.g. bran, husk
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A40/00—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production
    • Y02A40/80—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production in fisheries management
    • Y02A40/81—Aquaculture, e.g. of fish
    • Y02A40/818—Alternative feeds for fish, e.g. in aquacultures
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P60/00—Technologies relating to agriculture, livestock or agroalimentary industries
    • Y02P60/80—Food processing, e.g. use of renewable energies or variable speed drives in handling, conveying or stacking
    • Y02P60/87—Re-use of by-products of food processing for fodder production

Description

本発明は、γオリザノール、トコフェロール、ポリフェノール類等の極性のある健康機能成分を吸着・濃縮した乾燥脱脂穀類糠、該糠から調製した該健康機能成分の濃縮物；該健康機能成分が吸着・濃縮された乾燥脱脂穀類糠又は健康機能成分の濃縮物からなる極性のある健康機能成分含有飲食品用、医薬用、医薬部外品用、化粧品用、動物飼料用、又は水産飼料用素材；及びそれらの製造方法に関する。   The present invention relates to a dried defatted cereal meal obtained by adsorbing and concentrating a polar health function ingredient such as γ-oryzanol, tocopherol, polyphenols, etc., a concentrate of the health function ingredient prepared from the koji; A material for polar health function ingredient-containing foods, medicines, quasi-drugs, cosmetics, animal feeds, or aquatic feeds composed of a dried defatted cereal meal or a concentrate of health function ingredients; It relates to the manufacturing method.

従来より、米糠等を原料として、米油等の植物油が製造されている。近年の研究により、この米油等植物油の原料となる米糠等には、γオリザノール、トコフェロール、ポリフェノール等の有用な健康機能成分が含まれていることが確認されている。例えば、γオリザノールについては、生長促進作用、性腺刺激作用、ビタミンＥ様作用、抗ストレス作用、脱コレステロール作用、抗高脂血症等の薬理作用や、抗酸化作用、紫外線吸収作用、チロシナーゼ活性抑制作用、皮膚温上昇作用等の生理活性作用が知られている。また、トコフェロールについては、脂質代謝改善作用、膜安定化作用、内分泌賦活作用、性機能向上作用、免疫増強作用、創傷修復作用、放射線障害防御作用、抗老化作用等が、カテキン類等のポリフェノールについては、抗菌活性、抗酸化活性、抗う食活性、抗ウイルス活性、抗アレルギー活性、α−アミラーゼ阻害活性、血圧上昇抑制作用、血中コレステロール低下作用等の生理活性作用が知られている。   Conventionally, vegetable oils such as rice oil have been produced using rice bran as a raw material. Recent research has confirmed that rice bran, which is a raw material for vegetable oils such as rice oil, contains useful health functional ingredients such as γ-oryzanol, tocopherol, and polyphenol. For example, for γ-oryzanol, growth promoting action, gonadal stimulating action, vitamin E-like action, anti-stress action, decholesterol action, anti-hyperlipidemia and other pharmacological actions, antioxidant action, ultraviolet absorption action, tyrosinase activity suppression Physiologically active actions such as action and skin temperature raising action are known. In addition, for tocopherol, lipid metabolism improving effect, membrane stabilizing effect, endocrine stimulating effect, sexual function improving effect, immune enhancing effect, wound repair effect, radiation damage protective effect, anti-aging effect, etc. are related to polyphenols such as catechins Is known to have physiological activities such as antibacterial activity, antioxidant activity, anti-cariogenic activity, antiviral activity, antiallergic activity, α-amylase inhibitory activity, blood pressure increase inhibitory effect, blood cholesterol lowering effect and the like.

γオリザノール等の生理活性物質は、米糠等に多く含まれるものであるが、従来行なわれていた米油等の製造方法においては、これらの生理活性物質を、該食油中に残存させて、精製することが難しく、食油の利用に際してこれらの生理活性物質を有効に利用することができなかった。すなわち、従来、米油等の精製法としては、アルカリ精製法と蒸留脱酸法とが知られているが、アルカリ精製法においては、採油；脱ガム；脱ロウ；アルカリ脱酸；脱色；脱臭の工程において、γオリザノールが、油脂相から油滓に移行してしまい、アルカリ脱酸油には、極微量のγオリザノールしか残存しなかった。一方、蒸留脱酸法においては、アルカリ精製法におけるアルカリ脱酸に代えて、蒸留によって脂肪酸を除去しようとするものであり、高温真空蒸留によって、遊離脂肪酸を留去し、かつ、γオリザノールを油脂相に残存せしめる。しかし、この方法では、その後の脱臭工程においてγオリザノールの消失を防ぐためには、通常よりも低温での脱臭工程を経なければならず、このような脱臭処理では、良好な風味の油脂を得るのが難しく、γオリザノールを含有し、しかも、良好な風味の油脂を製造することは難かしかった。   Physiologically active substances such as γ oryzanol are abundantly contained in rice bran and the like. However, in the conventional methods for producing rice oil and the like, these physiologically active substances are left in the cooking oil and purified. It was difficult to use these physiologically active substances when using edible oil. That is, conventionally, as a method for refining rice oil or the like, an alkali refining method and a distillation deoxidation method are known. In the alkali refining method, oil collection; degumming; dewaxing; alkaline deoxidation; decolorization; deodorization. In this step, γ oryzanol was transferred from the oil phase to the oil cake, and only a very small amount of γ oryzanol remained in the alkaline deoxidized oil. On the other hand, in the distillation deoxidation method, instead of the alkali deoxidation in the alkali refining method, fatty acids are to be removed by distillation, free fatty acids are distilled off by high-temperature vacuum distillation, and γ-oryzanol is removed from oils and fats. Let it remain in the phase. However, in this method, in order to prevent the disappearance of γ-oryzanol in the subsequent deodorization process, a deodorization process at a temperature lower than usual must be performed. In such a deodorization process, fats and oils having a good flavor are obtained. However, it was difficult to produce oils and fats containing γ oryzanol and having a good flavor.

そこで、米糠等に含まれるγオリザノール等の健康機能物質を有効に利用するために、従来より、該成分を含有する食用油等の各種の調製方法が提案されている。例えば、特開平６−３４０８８９号公報には、米糠原油を精製するに際し、真空下で水蒸気蒸留により、含有される脂肪酸除去し、オリザノール類を濃縮させた米油を製造する方法が開示されている。また、特開２０００−１１９６８１号公報には、米糠から油を抽出する際に、米糠を予めアミラーゼ、セルラーゼ、ヘミセルラーゼ、プロテアーゼ等の酵素を用いて処理し、炭化水素系有機溶剤で抽出することにより、オリザノールやステロールを１．８重量％以上含有する生理活性米糠油を製造することについて、特開２００２−２３８４５５号公報には、米糠原料から原油を抽出し、該原油の脱ガム、脱ロウ、脱酸工程を経て、原油を精製する米油の製造方法において、原油を２１０〜２５０℃の蒸留温度で真空状態で蒸留し、更に、アルカリ処理して脱酸し、或いは原油の脱ガム、脱ロウ、脱臭工程を経て、原油を精製する米油の製造方法において、原油を減圧下、２５０℃以下で蒸留することにより脱臭し、γオリザノールやトコフェノール、ステロール等を含有する米油を製造する方法が開示されている。   Therefore, in order to effectively use health functional substances such as γ-oryzanol contained in rice bran, various methods for preparing edible oils and the like containing the components have been proposed. For example, Japanese Patent Application Laid-Open No. 6-340889 discloses a method for producing rice oil obtained by removing fatty acids contained therein and concentrating oryzanols by steam distillation under vacuum when refining rice bran crude oil. . Japanese Patent Laid-Open No. 2000-119681 discloses that when extracting oil from rice bran, the rice bran is previously treated with an enzyme such as amylase, cellulase, hemicellulase, protease and extracted with a hydrocarbon-based organic solvent. JP, 2002-238455, discloses that a crude oil is extracted from a rice bran raw material, and the crude oil is degummed and dewaxed. , In a method for producing rice oil that undergoes a deoxidation step and refines crude oil, the crude oil is distilled in a vacuum state at a distillation temperature of 210 to 250 ° C., and is further deacidified by alkali treatment, or crude oil degumming, In a method for producing rice oil that undergoes a dewaxing and deodorizing process and refines crude oil, the crude oil is deodorized by distillation at 250 ° C. or less under reduced pressure, and γ-Oryzanol and Tokov Nord, a method for producing a rice oil containing sterols and the like are disclosed.

また、特開２００２−２９３７９３号公報、特開２００４−３０００３４号公報には、米糠油ソープストックに水酸化ナトリウムのようなアルカリを加えて鹸化し、脱水した鹸化ソープストックを、酢酸エチル、アセトンのような有機溶媒で抽出してオリザノール富化フラクションを得、更には、カラムクロマトグラフィーにかけて、オリザノール富化画分を得る方法について、特開２００７−１２４９１７号公報には、米糠から製造される米油を原料として、アルカリ抽出、或いは、リパーゼのような酵素で処理して、高濃度のオリザノールを含有する米油を製造する方法について開示されている。これらの従来の方法は、米糠等に含まれるγオリザノール等の健康機能物質を利用するために、該成分を含有する食用油として調製するものであるが、いずれも複雑な処理を必要とするため、実用的な食用油の製造方法としては適用性に欠け、しかも、かかる方法で調製される製品は、いずれも食用油の形であるため、これを食品や医薬、或いは化粧品や飼料等の各種の用途における機能性素材として用いる場合に、その利用対象が制限され、利用上制約があった。   In addition, JP 2002-293793 A and JP 2004-300034 A disclose that a saponified soap stock which has been saponified by adding an alkali such as sodium hydroxide to rice bran oil soap stock and dehydrated with ethyl acetate and acetone. Extraction with such an organic solvent gives an oryzanol-enriched fraction, and further, a method for obtaining an oryzanol-enriched fraction by column chromatography, Japanese Patent Application Laid-Open No. 2007-1224917 discloses rice oil produced from rice bran. Is used to produce rice oil containing a high concentration of oryzanol by alkaline extraction or treatment with an enzyme such as lipase. These conventional methods are prepared as edible oils containing the components in order to use health functional substances such as γ-oryzanol contained in rice bran etc., but both require complicated processing. In addition, as a practical method for producing edible oil, the applicability is lacking, and since the products prepared by such a method are all in the form of edible oil, they are used in various forms such as food, medicine, cosmetics and feed. When it is used as a functional material in the above-mentioned applications, its use target is limited, and there are restrictions on use.

他方で、米糠のような穀類糠を、各種成分の吸着担体として用いることが知られている。例えば、特開平９−１８２５６２号公報には、コレステロールを含む動物性液化脂肪物質に、大豆、菜種、綿実、米糠のような油糧植物の種子又は油脂を抽出した油糧植物残滓を接触させることによって、コレステロールを吸着させ、このコレステロールを吸着させた油糧植物残滓を動物性液化脂肪物質から分離することによりコレステロールを除去する方法が開示されている。また、特開２００４−３２９０１９号公報には、脱脂糠やパーライトのようなグリセリン吸着担体とグリセリンとを混合して、グリセリン吸着担体にグリセリンを吸着させ、グリセリン吸着飼料を調製する方法が開示されている。しかしながら、米糠のような穀類糠を、γオリザノール等の健康機能物質の吸着に用い、該成分の精製・濃縮に用いるようなことについては知られていなかった。   On the other hand, it is known to use cereal meal such as rice bran as an adsorption carrier for various components. For example, in Japanese Patent Application Laid-Open No. 9-182562, an animal liquefied fatty substance containing cholesterol is contacted with oil plant seeds extracted from oil plant seeds such as soybeans, rapeseed, cottonseed, and rice bran, or fats and oils. Thus, there is disclosed a method for removing cholesterol by adsorbing cholesterol and separating the oily plant residue adsorbed with cholesterol from animal liquefied fatty substances. Japanese Patent Application Laid-Open No. 2004-329019 discloses a method of preparing a glycerin-adsorbed feed by mixing a glycerin-adsorbing carrier such as defatted lees and perlite with glycerin and adsorbing the glycerin to the glycerin-adsorbing carrier. Yes. However, it has not been known that cereal meal such as rice bran is used for adsorbing health functional substances such as γ-oryzanol and used for purification and concentration of the components.

特開平６−３４０８８９号公報。JP-A-6-340889. 特開平９−１８２５６２号公報。JP-A-9-182562. 特開２０００−１１９６８１号公報。JP 2000-119681 A. 特開２００２−２３８４５５号公報。JP 2002-238455 A. 特開２００２−２９３７９３号公報。JP 2002-293793 A. 特開２００４−３０００３４号公報。Japanese Patent Application Laid-Open No. 2004-300034. 特開２００４−３２９０１９号公報。Japanese Patent Application Laid-Open No. 2004-329019. 特開２００７−１２４９１７号公報。JP 2007-124917 A.

本発明の課題は、γオリザノール、トコフェロール、ポリフェノール類等からなる極性のある健康機能成分を有効に利用するために、該成分を含有する原料から該健康機能成分を、実用的に適用できる簡便かつ効果的な手段で、精製、取得し、しかも、精製、取得した健康機能成分を含有する素材が、飲食品、医薬品、医薬部外品、化粧品、動物飼料又は水産飼料等の広い利用分野で、有効に利用できる素材を製造する方法、及び該方法によって製造された健康機能成分を含有する素材を提供することにある。   An object of the present invention is to easily use a health function component having a polarity from a raw material containing the component in order to effectively use a polar health function component composed of γ oryzanol, tocopherol, polyphenols and the like. In a wide field of use such as food and drink, pharmaceuticals, quasi-drugs, cosmetics, animal feeds or aquatic feeds, the materials containing the health functional ingredients that have been refined and acquired by effective means An object of the present invention is to provide a method for producing a material that can be effectively used, and a material containing a health functional ingredient produced by the method.

本発明者は、米糠等に含まれるγオリザノール、トコフェロール、ポリフェノール類等からなる極性のある健康機能成分を有効に利用するために、該健康機能成分を精製、濃縮、分離する方法について鋭意検討する中で、乾燥脱脂米糠のような乾燥脱脂穀類糠が、γオリザノール、トコフェロール、ポリフェノール類等の比較的極性の高い健康機能成分を特異的に吸着し、該健康機能成分を穀類糠内に濃縮できる性質を持つことを見い出し、該乾燥脱脂穀類糠の性質を利用して、γオリザノール、トコフェロール、ポリフェノール類等の極性のある健康機能成分を含有する原料から、該健康機能成分を選択的にかつ効果的に吸着し、濃縮することができることを見い出し、本発明を完成するに至った。   The present inventor intensively examines a method for purifying, concentrating, and separating the health functional ingredient in order to effectively use the polar health functional ingredient composed of γ-oryzanol, tocopherol, polyphenols and the like contained in rice bran and the like. Among them, dry defatted cereal meal such as dry defatted rice bran can specifically adsorb relatively high-polarity health functional ingredients such as γ-oryzanol, tocopherol, polyphenols, etc., and concentrate the health functional ingredients in the cereal meal. Using the properties of the dried defatted cereal meal, selectively and effectively the health functional ingredients from raw materials containing polar health functional ingredients such as γ-oryzanol, tocopherol, polyphenols, etc. The present invention was completed.

すなわち、本発明は、γオリザノール、トコフェロール、及びポリフェノール類等の極性のある健康機能成分を含有する原料から、有機溶媒によって抽出された抽出物を、乾燥脱脂穀類糠を吸着担体として吸着処理することにより、γオリザノール、トコフェロール、ポリフェノール等の極性のある健康機能成分が吸着・濃縮された乾燥脱脂穀類糠を製造する方法からなる。本発明において原料として用いられる、有機溶媒によって抽出され、γオリザノール、トコフェロール、及びポリフェノール類等の極性のある健康機能成分を含有する抽出物としては、好ましくは、米糠或いはコンブから抽出された抽出物を挙げることができる。   That is, the present invention performs an adsorption treatment on an extract extracted from an organic solvent from a raw material containing polar health functional ingredients such as γ-oryzanol, tocopherol, and polyphenols, using dried defatted cereal meal as an adsorption carrier. Thus, it comprises a method for producing a dried defatted cereal meal with adsorbed and concentrated polar health function components such as γ-oryzanol, tocopherol and polyphenol. The extract used as a raw material in the present invention, which is extracted with an organic solvent and contains polar health functional components such as γ-oryzanol, tocopherol, and polyphenols, is preferably an extract extracted from rice bran or kombu Can be mentioned.

本発明において、γオリザノール、トコフェロール、ポリフェノール等の極性のある健康機能成分を吸着・濃縮する担体として用いられる乾燥脱脂穀類糠としては、好ましくは、乾燥脱脂米糠又は乾燥脱脂小麦糠（乾燥脱脂小麦フスマ）を挙げることができる。本発明における特に好ましい態様として、乾燥脱脂穀類糠は、穀類糠を低極性有機溶媒及び高極性有機溶媒で洗浄し、極性の高い化学物質を吸着する吸着担体であるように改質した脱脂穀類糠を乾燥したものを用いることができる。本発明において、かかる洗浄処理に用いる、低極性有機溶媒としては、ｎ−ヘキサン又はクロロホルムからなる低極性有機溶媒を挙げることができ、高極性有機溶媒としては、アセトン、メタノール又はエタノールからなる高極性有機溶媒を挙げることができる。本発明において、極性の高い化学物質を吸着する吸着担体であるように改質した脱脂穀類糠を乾燥するには、脱脂穀類糠を５０〜１００℃で、１２〜２４時間乾燥する条件で行なうことができる。   In the present invention, the dried defatted cereal meal used as a carrier for adsorbing and concentrating polar health functional components such as γ-oryzanol, tocopherol, polyphenol, etc. is preferably dried defatted rice bran or dried defatted wheat bran (dried defatted wheat bran). ). As a particularly preferred embodiment of the present invention, the dried defatted cereal meal is obtained by washing the cereal meal with a low-polar organic solvent and a high-polar organic solvent, and modifying the defatted cereal meal to be an adsorption carrier that adsorbs a highly polar chemical substance. A dried product can be used. In the present invention, the low-polar organic solvent used for the washing treatment can include a low-polar organic solvent composed of n-hexane or chloroform, and the high-polar organic solvent includes a high-polarity composed of acetone, methanol or ethanol. Mention may be made of organic solvents. In the present invention, in order to dry a defatted cereal meal that has been modified to be an adsorption carrier that adsorbs a highly polar chemical substance, the defatted cereal meal is dried at 50 to 100 ° C. for 12 to 24 hours. Can do.

本発明において、乾燥脱脂穀類糠を吸着担体として行う、健康機能成分の吸着・濃縮処理は、非極性有機溶媒を用いて行なわれる。かかる場合の特に好ましい非極性有機溶媒としては、ｎ−ヘキサンを挙げることができる。また、かかる乾燥脱脂穀類糠を吸着担体として用いる健康機能成分の吸着処理は、中性乃至酸性条件下で行なうことが好ましい。   In the present invention, the adsorption / concentration treatment of the health functional component, which is performed using dried defatted cereal meal as an adsorption carrier, is performed using a nonpolar organic solvent. A particularly preferable nonpolar organic solvent in such a case may be n-hexane. Moreover, it is preferable to perform the adsorption | suction process of the health functional component which uses this dry defatted cereal meal as an adsorption carrier under neutral thru | or acidic conditions.

本発明においては、本発明の方法によって製造されたγオリザノール、トコフェロール、及びポリフェノール類等の極性のある健康機能成分が吸着・濃縮された乾燥脱脂穀類糠から、極性の溶出・分離溶媒を用いて該健康機能成分を溶出・分離することにより、γオリザノール、トコフェロール、及びポリフェノール類等の極性のある健康機能成分を濃縮した濃縮物を製造することができる。かかる溶出・分離に用いる好ましい極性溶出・分離溶媒としては、ｎ−ヘキサン・エタノール混合溶媒を挙げることができる。   In the present invention, a polar elution / separation solvent is used from dried defatted cereal meals adsorbed and concentrated with polar health function components such as γ-oryzanol, tocopherol, and polyphenols produced by the method of the present invention. By eluting and separating the health function component, a concentrate in which polar health function components such as γ-oryzanol, tocopherol, and polyphenols are concentrated can be produced. As a preferred polar elution / separation solvent used for such elution / separation, an n-hexane / ethanol mixed solvent can be mentioned.

本発明において、健康機能成分が吸着・濃縮された乾燥脱脂穀類糠から、γオリザノール、トコフェロール、及びポリフェノール類等の極性のある健康機能成分を溶出・分離溶媒を用いて溶出・分離する処理は、アルカリ条件下で行なうことが好ましい。   In the present invention, a process for eluting and separating polar health function components such as γ oryzanol, tocopherol, and polyphenols from a dried defatted cereal meal with adsorbed and concentrated health function components using a separation solvent, It is preferable to carry out under alkaline conditions.

本発明の製造方法によって製造されたγオリザノール、トコフェロール、及びポリフェノール類等の極性のある健康機能成分が吸着・濃縮された乾燥脱脂穀類糠、又は、該健康機能成分の濃縮物は、種々の用途に利用することができ、健康機能成分含有飲食品用、医薬品用、医薬部外品用、化粧品用、動物飼料用、又は水産飼料用の素材として、特に、制約なく用いることができる。   The dried defatted cereal meal or adsorbed and concentrated polar health function components such as γ-oryzanol, tocopherol, and polyphenols produced by the production method of the present invention, or concentrates of the health function components are used in various applications. Especially, it can be used without restriction as a material for health functional ingredient-containing foods and drinks, pharmaceuticals, quasi drugs, cosmetics, animal feeds, or marine feeds.

すなわち具体的には本発明は、［１］穀類糠をｎ−ヘキサン又はクロロホルムからなる低極性有機溶媒及びアセトン、メタノール又はエタノールからなる高極性有機溶媒で洗浄し、極性の高い化学物質を吸着する吸着担体として改質した脱脂穀類糠を、乾燥処理することによって調製した乾燥脱脂穀類糠を吸着担体とし、γオリザノール、トコフェロール、及びポリフェノール類から選択される１又は２以上の極性のある健康機能成分を含有する原料から、有機溶媒によって抽出された抽出物を、該乾燥脱脂穀類糠からなる吸着担体によって、中性乃至酸性条件下で非極性有機溶媒を用いて吸着処理することを特徴とするγオリザノール、トコフェロール、及びポリフェノール類から選択される１又は２以上の極性のある健康機能成分が吸着・濃縮された乾燥脱脂穀類糠の製造方法や、［２］γオリザノール、トコフェロール、及びポリフェノール類から選択される１又は２以上の極性のある健康機能成分を含有する原料から、有機溶媒によって抽出された抽出物が、米糠或いはコンブから抽出された抽出物であることを特徴とする上記［１］に記載のγオリザノール、トコフェロール、及びポリフェノール類から選択される１又は２以上の極性のある健康機能成分が吸着・濃縮された乾燥脱脂穀類糠の製造方法や、［３］乾燥脱脂穀類糠が、乾燥脱脂米糠又は乾燥脱脂小麦フスマであることを特徴とする上記［１］又は［２］に記載のγオリザノール、トコフェロール、及びポリフェノール類から選択される１又は２以上の極性のある健康機能成分が吸着・濃縮された乾燥脱脂穀類糠の製造方法からなる。
Specifically, the present invention specifically [1] cereal meal is washed with a low polarity organic solvent composed of n-hexane or chloroform and a high polarity organic solvent composed of acetone, methanol or ethanol , and adsorbs a highly polar chemical substance. One or two or more polar health functional ingredients selected from γ-oryzanol, tocopherol, and polyphenols, using a dried defatted cereal meal prepared by drying a defatted cereal meal modified as an adsorption carrier An extract extracted from an organic solvent with an organic solvent is adsorbed with a nonpolar organic solvent under neutral to acidic conditions with an adsorption carrier made of the dried defatted cereal meal. Adsorbs or absorbs one or more polar health functional ingredients selected from oryzanol, tocopherol, and polyphenols Extracted with an organic solvent from a method for producing a concentrated dried defatted cereal meal and a raw material containing one or more polar health functional ingredients selected from [2] γ-oryzanol, tocopherol, and polyphenols The extract is an extract extracted from rice bran or kombu. One or two or more polar health function ingredients selected from γ-oryzanol, tocopherol, and polyphenols according to [1] above A method for producing a dried defatted cereal meal with adsorbed and concentrated, or [3] The dried defatted cereal meal is dried defatted rice bran or dried defatted wheat bran, according to the above [1] or [2] Dried defatted cereal meal with adsorbed and concentrated one or more polar health functional ingredients selected from gamma oryzanol, tocopherol and polyphenols Consisting of production method.

また本発明は、［４］乾燥脱脂穀類糠が、脱脂穀類糠を５０〜１００℃で、１２〜２４時間乾燥処理したものであることを特徴とする上記［１］〜［３］のいずれかに記載のγオリザノール、トコフェロール、及びポリフェノール類から選択される１又は２以上の極性のある健康機能成分が吸着・濃縮された乾燥脱脂穀類糠の製造方法や、［５］γオリザノール、トコフェロール、及びポリフェノール類から選択される１又は２以上の極性のある健康機能成分を含有する原料から、有機溶媒によって抽出された抽出物を、乾燥脱脂穀類糠からなる吸着担体によって、非極性有機溶媒を用いて行う吸着処理を、ｎ−ヘキサンを用いて行なうことを特徴とする上記［１］〜［４］のいずれかに記載のγオリザノール、トコフェロール、及びポリフェノール類から選択される１又は２以上の極性のある健康機能成分が吸着・濃縮された乾燥脱脂穀類糠の製造方法からなる。
Moreover, this invention is [4 ] any one of said [ 1]-[3], wherein dry defatted cereal meal is obtained by drying defatted cereal meal at 50-100 ° C. for 12-24 hours . gamma oryzanol, tocopherols, and one or more health functional components with a polar and manufacturing method of the adsorbed and concentrated dry defatted cereal bran is selected from polyphenols described, [5] gamma oryzanol, tocopherols, and An extract extracted with an organic solvent from a raw material containing one or more polar health functional ingredients selected from polyphenols is adsorbed using an adsorbent carrier made of dried defatted cereal meal using a nonpolar organic solvent. γ oryzanol according to any one of the adsorption treatment, the above-mentioned [1], wherein the performed with n- hexane - [4] performed, tocopherols, and port One or more polar certain health functional components adsorbed and concentrated dry defatted cereal bran manufacturing how or Ranaru selected from phenols.

さらに本発明は、［６］上記［１］〜［５］のいずれかに記載のγオリザノール、トコフェロール、及びポリフェノール類から選択される１又は２以上の極性のある健康機能成分が吸着・濃縮された乾燥脱脂穀類糠の製造方法を用いて、該乾燥脱脂穀類糠を製造し、該乾燥脱脂穀類糠から、該極性のある健康機能成分を極性の溶出・分離溶媒を用いて中性乃至アルカリ条件下で溶出・分離することを特徴とするγオリザノール、トコフェロール、及びポリフェノール類から選択される１又は２以上の極性のある健康機能成分の濃縮物の製造方法や、［７］極性の溶出・分離溶媒として、ｎ−ヘキサン・エタノール混合溶媒を用いることを特徴とする上記［６］に記載のγオリザノール、トコフェロール、及びポリフェノール類から選択される１又は２以上の極性のある健康機能成分の濃縮物の製造方法や、［８］γオリザノール、トコフェロール、及びポリフェノール類から選択される１又は２以上の極性のある健康機能成分の濃縮物が、健康機能成分含有飲食品用、医薬品用、医薬部外品用、化粧品用、動物飼料用、又は水産飼料用の素材であることを特徴とする上記［６］又は［７］に記載のγオリザノール、トコフェロール、及びポリフェノール類から選択される１又は２以上の極性のある健康機能成分の濃縮物の製造方法からなる。 Furthermore, the present invention provides an adsorbed / concentrated health function component having one or more polarities selected from [ 6 ] gamma oryzanol, tocopherol and polyphenols according to any one of [ 1] to [5 ] above. The dried defatted cereal meal is produced using the method for producing the dried defatted cereal meal, and the polar health function component is neutralized from the dried defatted cereal meal using a polar elution / separation solvent. A method for producing a concentrate of one or more polar health functional ingredients selected from γ-oryzanol, tocopherol, and polyphenols characterized by elution / separation below, and [ 7 ] elution / separation of polarity as the solvent, is selected from γ-oryzanol, tocopherol, and polyphenols according to [6], wherein the use of n- hexane-ethanol mixed solvent That one or more of and manufacturing methods of the concentrate of health functional components with a polar, [8] gamma oryzanol, tocopherols, and concentrates of one or more polar health functional components with a selected from polyphenols The gamma according to the above [ 6] or [7 ], characterized in that it is a material for health function ingredient-containing foods and drinks, pharmaceuticals, quasi drugs, cosmetics, animal feeds, or marine feeds It consists of a method for producing a concentrate of one or more polar health functional ingredients selected from oryzanol, tocopherol and polyphenols.

本発明は、γオリザノール、トコフェロール、ポリフェノール類等の極性のある健康機能成分を有効に利用するために、該成分を含有する原料から該健康機能成分を吸着・濃縮した素材、或いは、該健康機能成分を吸着・濃縮した素材から、該健康機能成分を溶出・分離した該健康機能成分の濃縮物を、実用的に適用できる簡便かつ安価に、更に、効果的な手段で、取得する方法を提供する。本発明で製造される健康機能成分を吸着・濃縮した素材や、該素材から溶出・分離した該健康機能成分の濃縮物は、乾燥脱脂穀類糠を担体としていることから、素材的に安全で、しかも、各種の用途に対して適応性の高い性質を有し、飲食品、医薬品、化粧品、医薬部外品、動物飼料又は水産飼料等の広い利用分野で、健康機能を付与した製品の製造に有効に利用できる素材を提供する。   In order to effectively use polar health function components such as γ oryzanol, tocopherol, and polyphenols, the present invention is a material obtained by adsorbing and concentrating the health function components from raw materials containing the components, or the health function Provides a simple and inexpensive method that can be applied practically and with effective means to obtain a concentrate of the health function component that has been eluted and separated from the material that has adsorbed and concentrated the component. To do. The material obtained by adsorbing and concentrating the health function ingredient produced in the present invention, and the concentrate of the health function ingredient eluted and separated from the material are made from dry defatted cereal meal as a carrier. In addition, it has properties that are highly adaptable to various uses, and is used to manufacture products with health functions in a wide range of applications such as food and drink, pharmaceuticals, cosmetics, quasi-drugs, animal feed, and marine feed. Provide materials that can be used effectively.

本発明は、γオリザノール、トコフェロール、及びポリフェノール類等の極性のある健康機能成分を含有する原料から、有機溶媒によって抽出された抽出物を、乾燥脱脂穀類糠を吸着担体として吸着処理することにより、γオリザノール、トコフェロール、及びポリフェノール類等の極性のある健康機能成分が吸着・濃縮された乾燥脱脂穀類糠を製造する方法からなる。   The present invention, by subjecting an extract extracted from an organic solvent from a raw material containing polar health functional ingredients such as γ-oryzanol, tocopherol, and polyphenols, by adsorption treatment using dried defatted cereal meal as an adsorption carrier, It consists of a method for producing a dried defatted cereal meal with adsorbed and concentrated polar health function components such as γ oryzanol, tocopherol, and polyphenols.

γオリザノール、トコフェロール、及びポリフェノール類等の健康機能成分は、米糠や、コンブに豊富に含まれることから、本発明においては、該植物材料から有機溶媒によって抽出された抽出物を原料として用いる。植物材料から該健康機能成分を含有する抽出物を抽出するために使用される有機溶媒としては、メタノール、エタノール、プロパノール等の低級アルコール、アセトン、酢酸エチル、ジエチルエーテル等のエーテル類、ｎ−ヘキサンのような低分子飽和炭化水素、及びそれらの混合溶媒を適宜用いることができるが、その後の乾燥脱脂穀類糠による吸着・濃縮処理等からすると、ｎ−ヘキサンを用いることが特に好ましい。   Since health functional ingredients such as γ-oryzanol, tocopherol, and polyphenols are abundantly contained in rice bran and kombu, an extract extracted from the plant material with an organic solvent is used as a raw material in the present invention. Examples of the organic solvent used for extracting the extract containing the health functional ingredient from plant materials include lower alcohols such as methanol, ethanol and propanol, ethers such as acetone, ethyl acetate and diethyl ether, and n-hexane. Although low molecular saturated hydrocarbons such as these and mixed solvents thereof can be used as appropriate, n-hexane is particularly preferred from the standpoint of subsequent adsorption / concentration treatment with dried defatted cereal meal.

本発明において、健康機能成分の吸着・濃縮担体として用いられる脱脂穀類糠としては、脱脂された米糠、小麦糠（小麦フスマ）、玉蜀黍糠、大麦糠、ライ麦糠、燕麦糠、高粱糠、鳩麦糠等の脱脂穀類糠を挙げることができるが、好ましい脱脂穀類糠としては、脱脂米糠、脱脂小麦糠（小麦フスマ）を挙げることができる。
本発明において用いられる乾燥脱脂穀類糠は、穀類糠を低極性有機溶媒及び高極性有機溶媒で洗浄し、極性の高い化学物質を吸着する吸着担体であるように改質した脱脂穀類糠を乾燥したものであることが好ましい。該処理は、穀類糠をヘキサン又はクロロホルムからなる低極性有機溶媒及びアセトン、メタノール又はエタノールからなる高極性有機溶媒で洗浄処理することにより行われる。乾燥脱脂穀類糠の調製は、脱脂穀類糠を５０〜１００℃で、１２〜２４時間乾燥処理することにより調製される。 In the present invention, the defatted cereal meal used as a carrier for adsorbing and concentrating health functional ingredients includes defatted rice straw, wheat straw (wheat bran), onion, barley meal, rye meal, buckwheat meal, high meal, pigeon meal Examples of preferred defatted cereal meals include defatted rice meal and defatted wheat meal (wheat bran).
The dry defatted cereal meal used in the present invention was obtained by washing the cereal meal with a low-polar organic solvent and a high-polar organic solvent and drying the defatted cereal meal modified so as to be an adsorption carrier that adsorbs a highly polar chemical substance. It is preferable. This treatment is performed by washing the cereal meal with a low polarity organic solvent composed of hexane or chloroform and a high polarity organic solvent composed of acetone, methanol or ethanol. The dry defatted cereal meal is prepared by drying the defatted cereal meal at 50-100 ° C. for 12-24 hours.

本発明において、乾燥脱脂穀類糠を吸着担体として行う吸着処理は、健康機能成分を溶解した非極性有機溶媒を用いて行なわれる。該非極性有機溶媒としては、担体への非吸着性等の観点から、ｎ−ヘキサンを用いて行なうことが特に好ましい。また、該乾燥脱脂穀類糠を吸着担体として健康機能成分を吸着する処理は、中性乃至酸性条件下で行なうことが好ましい。本発明において、乾燥脱脂穀類糠を用いて健康機能成分を吸着・濃縮するには、乾燥脱脂穀類糠を健康機能成分を溶解した溶媒に浸漬することにより行なうことができるが、好ましくは、乾燥脱脂穀類糠吸着担体を充填したカラムを用いて、健康機能成分を溶解した溶媒を通液することにより実施される。   In the present invention, the adsorption treatment in which dried defatted cereal meal is used as an adsorption carrier is performed using a nonpolar organic solvent in which a health functional component is dissolved. The nonpolar organic solvent is particularly preferably n-hexane from the viewpoint of non-adsorption on the carrier. Moreover, it is preferable to perform the process which adsorb | sucks a health functional component by using this dry defatted cereal meal as an adsorption carrier under neutral thru | or acidic conditions. In the present invention, adsorbing and concentrating the health functional component using the dried defatted cereal meal can be performed by immersing the dried defatted cereal meal in a solvent in which the health functional ingredient is dissolved. It is carried out by passing a solvent in which the health function component is dissolved using a column packed with a cereal bran adsorption carrier.

本発明において、健康機能成分を吸着・濃縮した乾燥脱脂穀類糠は、健康機能成分含有素材として各種の用途に用いることができるが、該健康機能成分を吸着・濃縮した乾燥脱脂穀類糠から、健康機能成分を溶出・分離溶媒を用いて溶出・分離することにより、健康機能成分の濃縮物を製造することができる。該健康機能成分の溶出・分離溶媒としては、極性の溶出・分離溶媒が用いられ、該溶出・分離溶媒としては、ｎ−ヘキサン・エタノール混合溶媒が特に好ましい溶出・分離溶媒として用いられる。かかる健康機能成分の溶出・分離には、溶出・分離の効率を上げるために、該溶出・分離をアルカリ条件下で行なうことが好ましい。   In the present invention, the dried defatted cereal meal obtained by adsorbing and concentrating the health functional ingredient can be used for various applications as a health functional ingredient-containing material. By elution / separation of the functional ingredient using an elution / separation solvent, a health functional ingredient concentrate can be produced. As the elution / separation solvent for the health function component, a polar elution / separation solvent is used. As the elution / separation solvent, an n-hexane / ethanol mixed solvent is used as a particularly preferable elution / separation solvent. In order to increase the elution / separation efficiency, it is preferable to perform the elution / separation under alkaline conditions for elution / separation of such health functional components.

本発明における健康機能成分が吸着・濃縮された乾燥脱脂穀類糠或いは濃縮物は、健康機能成分含有素材として、健康機能を付与した飲食品或いは医薬用食品用、錠剤、塗り薬、ドリンク剤のような医薬用、医薬部外品用、乳液、クリーム、ローションのような化粧品用、家畜やペットのような動物飼料用、又は水産動物のための水産飼料用等の各種の用途に用いられる。   The dried defatted cereal meal or concentrate obtained by adsorbing and concentrating the health function component in the present invention is used as a health function component-containing material, such as for foods and drinks or pharmaceutical foods with a health function, such as tablets, paints, and drinks. It is used for various uses such as pharmaceuticals, quasi-drugs, cosmetics such as emulsions, creams and lotions, animal feeds such as livestock and pets, and marine feeds for marine animals.

以下、実施例により本発明をより具体的に説明するが、本発明の技術的範囲はこれらの例示に限定されるものではない。   EXAMPLES Hereinafter, although an Example demonstrates this invention more concretely, the technical scope of this invention is not limited to these illustrations.

［乾燥脱脂米糠を用いた健康機能成分の吸着］   [Adsorption of health functional ingredients using dry defatted rice bran]

（乾燥脱脂米糠の調製）
米糠を順次ｎ−ヘキサン、ｎ−ヘキサンエタノール混合液、エタノール、水にて十分に洗浄し、極性の低いトリグリセリドや極性の高いフェルラ酸までほぼ全ての脂溶性成分を除去した。得られた完全脱脂米糠を１００℃で２４時間乾燥し、乾燥米糠を得た。 (Preparation of dry defatted rice bran)
The rice bran was sequentially washed thoroughly with n-hexane, a mixed solution of n-hexane ethanol, ethanol and water to remove almost all fat-soluble components from tripolar glycerides with low polarity and ferulic acid with high polarity. The obtained completely defatted rice bran was dried at 100 ° C. for 24 hours to obtain dried rice bran.

（健康機能成分含有抽出液の調製）
γオリザノールを含む市販米糠油を、ヘキサンにて抽出し、ｎ−ヘキサン飽和溶液を作成した。 (Preparation of extract containing health functional ingredients)
Commercial rice bran oil containing γ oryzanol was extracted with hexane to prepare a saturated n-hexane solution.

（吸着処理と結果）
調製された乾燥米糠に対して体積換算で５倍量のγオリザノールｎ−ヘキサン飽和溶液を加え、３０分間振とう攪拌した。これをｎ−ヘキサンで十分に洗浄し、過剰のγオリザノールを除去した。次いで、クロロホルムメタノールにて乾燥米糠に吸着したγオリザノールを完全に採取した。得られたγオリザノール抽出液をロータリーエバポレーター及び真空乾燥機にて完全に乾固し、その重量を測定した。その結果、乾燥米糠１ｇ当たり１．６７±０．１８ｍｇのγオリザノールが吸着していた（図１：γオリザノールを付加した脱脂米糠から再回収したγオリザノール）。乾重量１ｇあたりの脱脂米糠のγオリザノール含量が最大で８０μｇ程度であることから、２０倍もの強化が可能であることが明らかとなった。このように、脱脂米糠はγオリザノール強化担体としての利用が可能であることが確認された。 (Adsorption treatment and results)
To the prepared dried rice bran, 5 times the amount of saturated solution of γ-oryzanol n-hexane in terms of volume was added and stirred with shaking for 30 minutes. This was thoroughly washed with n-hexane to remove excess γ oryzanol. Subsequently, γ oryzanol adsorbed on the dried rice bran with chloroform methanol was completely collected. The obtained γ-oryzanol extract was completely dried using a rotary evaporator and a vacuum dryer, and the weight was measured. As a result, 1.67 ± 0.18 mg of γ oryzanol was adsorbed per 1 g of dried rice bran (FIG. 1: γ oryzanol recovered again from defatted rice bran added with γ oryzanol). Since the maximum γ oryzanol content of defatted rice bran per gram of dry weight is about 80 μg, it was revealed that it can be strengthened 20 times. Thus, it was confirmed that defatted rice bran can be used as a γ-oryzanol-enhanced carrier.

植物性ステロール及びαトコフェロールについても同様の検討を行ったところ、米糠１ｇ当たりそれぞれ０．８１±０．１１及び０．５８±０．０８ｍｇの植物性ステロール及びαトコフェロールが吸着された。更に、油脂１ｇ当たり１４ｍｇのγオリザノールを含む市販米糠油ヘキサン溶液に本担体を用いたところ、γオリザノールを米糠１ｇ当たり２．３０±０．２７ｍｇ吸着し、結果的に油脂１ｇ当たり４８０ｍｇまで濃縮することができた。γオリザノール単独で吸着試験を行った際よりも吸着量が増加したのは、米糠油にトリグリセリドなどの他の成分が存在することでｎ−ヘキサンへのγオリザノール溶解量が増大したため、吸着量も増えたものと予想される。   When the same examination was performed for plant sterol and α-tocopherol, 0.81 ± 0.11 and 0.58 ± 0.08 mg of plant sterol and α-tocopherol were adsorbed per 1 g of rice bran, respectively. Furthermore, when this carrier was used in a commercially available rice bran oil hexane solution containing 14 mg of γ oryzanol per gram of fat and oil, 2.30 ± 0.27 mg of γ oryzanol was adsorbed per gram of rice bran and consequently concentrated to 480 mg per gram of fat and oil. I was able to. The amount of adsorption increased compared to when γ oryzanol alone was used for the adsorption test because the amount of γ oryzanol dissolved in n-hexane increased due to the presence of other components such as triglyceride in rice bran oil. Expected to have increased.

［乾燥脱脂米糠を用いた健康機能成分の吸着と分離・濃縮］
米糠をｎ−ヘキサン、ジエチルエーテル、エタノールにて順次１０回以上洗浄した後、図２（脱脂米糠充填カラム）のようにガラスカラム内に充填した。クロロホルムメタノールによって乾燥利尻昆布から抽出した全脂質を重層し、１０カラム容のジエチルエーテルを流した。その後、ジエチルエーテル・エタノール混液（９８：２）にて溶出される画分をＴＬＣにて検出した。 [Adsorption, separation and concentration of health functional ingredients using dried defatted rice bran]
The rice bran was washed successively with n-hexane, diethyl ether and ethanol 10 times or more and then packed into a glass column as shown in FIG. 2 (defatted rice bran packed column). Total lipids extracted from dried Rishiri kelp with chloroform methanol were overlaid, and 10 column volumes of diethyl ether were flowed. Thereafter, the fraction eluted with diethyl ether / ethanol mixture (98: 2) was detected by TLC.

図３（ジエチルエーテル・エタノールにて溶出された画分の紫外蛍光像（左）及び硫酸検出像（右））に示すように、脱脂米糠に吸着されたγオリザノールがジエチルエーテル・エタノール混液にて溶出されることが明らかとなった。したがって、脱脂米糠は化学修飾を施すことなく、植物性ステロール、γオリザノールやクロロフィルなどの比較的極性の高い成分を特異的に吸着することが明らかとなった。これを利用してこれらの健康機能物質を脱脂米糠に濃縮することが可能である。   As shown in FIG. 3 (ultraviolet fluorescence image (left) and sulfuric acid detection image (right) of the fraction eluted with diethyl ether / ethanol), γ-oryzanol adsorbed on the defatted rice bran was mixed with diethyl ether / ethanol. Elution was revealed. Therefore, it was revealed that defatted rice bran specifically adsorbs relatively polar components such as plant sterols, γ oryzanol and chlorophyll without chemical modification. Using this, it is possible to concentrate these health functional substances into defatted rice bran.

分離・溶出溶媒について検討した。食品への適用を考えると、溶媒として麻酔作用などを有するジエチルエーテルを用いると残留性の問題が残る。一方、ｎ−ヘキサンは残留性が低く、米糠油の抽出にも用いられる。また、エタノールは飲用としても使用されることから、これらの混合溶媒にて同様の効果が得られるか否かについて検討を加えた。図４（ｎ−ヘキサン・エタノール混合溶媒によるγオリザノールの分離。図中白い星印がγオリザノール）に示すように、脱脂米糠カラムに吸着したγオリザノールは、ｎ−ヘキサン・エタノール混合溶媒（１００：１，ｖ／ｖ）によって溶出された。   The separation / elution solvent was examined. Considering application to foods, if diethyl ether having an anesthetic action is used as a solvent, the problem of persistence remains. On the other hand, n-hexane has low persistence and is also used for extraction of rice bran oil. In addition, since ethanol is also used for drinking, studies were made as to whether similar effects could be obtained with these mixed solvents. As shown in FIG. 4 (separation of γ oryzanol with a mixed solvent of n-hexane / ethanol. In the figure, a white star is γ oryzanol), γ oryzanol adsorbed on the defatted rice bran column is mixed with a mixed solvent of n-hexane / ethanol (100: 1, v / v).

そこで、更に詳細な溶出パターンを明らかにした。図５（ヘキサン・エタノール混合溶媒によるγオリザノールの分離。図中白い星印がγオリザノール。）に示すように、γオリザノールは脱脂米糠カラムより、ｎ−ヘキサン・エタノール（１００：０．７）で溶出されることが明らかとなった。   Therefore, a more detailed elution pattern was clarified. As shown in FIG. 5 (separation of γ oryzanol with a mixed solvent of hexane and ethanol. In the figure, a white star is γ oryzanol.) Γ oryzanol was removed from the defatted rice bran column with n-hexane / ethanol (100: 0.7). Elution was revealed.

［乾燥脱脂米糠に吸着した健康機能成分の溶出・分離条件の検討］
脱脂穀類糠によるγオリザノール吸着に及ぼすｐＨの影響について検討した。種々のｐＨ に調整した１００ｍＭ 3,3-dimethylglutaric acid(ＧＴＡ)緩衝液を作製し，γオリザノール吸着済み米糠（１ｇ）を緩衝液中（５０ｍｌ）中に分散して１時間室温で攪拌した．吸引濾過にて米糠を回収し，クロロホルムメタノール混液にて全脂質を抽出した．得られた抽出液を，クロロホルムを展開溶媒としたＳｉ６０シリカゲルにて分離し，３０２ｎｍにおける蛍光強度から定量し，吸着残増量を算出した。 [Examination of elution and separation conditions for health functional ingredients adsorbed on dried defatted rice bran]
The effect of pH on γ-oryzanol adsorption by defatted cereal meal was investigated. 100 mM 3,3-dimethylglutaric acid (GTA) buffer solutions adjusted to various pH were prepared, and rice bran (1 g) adsorbed with γ-oryzanol was dispersed in the buffer solution (50 ml) and stirred at room temperature for 1 hour. The rice bran was collected by suction filtration, and the total lipid was extracted with a chloroform methanol mixture. The obtained extract was separated on Si60 silica gel using chloroform as a developing solvent, and quantified from the fluorescence intensity at 302 nm to calculate the residual adsorption amount.

図６に示すようにγオリザノール吸着米糠はｐＨの上昇とともに吸着したγオリザノールを保持できなくなることが明らかとなった．これは，米糠中に含まれるリグニンのフェノール基がイオン化することによって，γオリザノールの吸着力が著しく低下することが主な原因であると考えられた．したがって，γオリザノール吸着米糠は，酸性である胃ではγオリザノールを吸着しており，中性から弱アルカリ性となる腸でγオリザノールを徐々に放出する徐放性を有することが明らかとなった。   As shown in FIG. 6, it was revealed that the γ-oryzanol-adsorbed rice bran cannot retain the adsorbed γ-oryzanol with increasing pH. The main reason for this was thought to be that the adsorbing power of γ-orizanol was significantly reduced by ionization of the phenolic group of lignin contained in rice bran. Therefore, it was clarified that γ-oryzanol-adsorbed rice bran adsorbs γ-orizanol in the acidic stomach and has a sustained release property that gradually releases γ-oryzanol in the intestines that are neutral to weakly alkaline.

［完全脱脂小麦フスマを用いた健康機能成分の吸着］
上記実施例１の乾燥脱脂米糠と同様の処理によって調製した完全脱脂小麦フスマ及び小麦フスマからデンプン並びにセルロースを糖化処理によって除いたバイオマス残渣について、γオリザノールの結合量を測定した。 [Adsorption of health functional ingredients using fully defatted wheat bran]
The binding amount of γ-oryzanol was measured on the completely defatted wheat bran prepared by the same treatment as the dried defatted rice bran of Example 1 and the biomass residue obtained by removing starch and cellulose from the wheat bran by saccharification treatment.

結果、前者では０．７５±０．１２ｍｇ／ｇ 完全脱脂小麦フスマ、後者では４．２１±０．６５ｍｇ／ｇ バイオマス残渣、の結合が確認できた。   As a result, binding of 0.75 ± 0.12 mg / g completely defatted wheat bran was observed in the former, and 4.21 ± 0.65 mg / g biomass residue was confirmed in the latter.

本発明の実施例における乾燥脱脂米糠を用いた健康機能成分の吸着試験において、脱脂米糠から再回収したγオリザノールについて示す図である。It is a figure shown about (gamma) oryzanol re-recovered from the defatted rice bran in the adsorption test of the health functional component using the dry defatted rice bran in the Example of this invention. 本発明の実施例において用いられた脱脂米糠充填カラムの写真である。It is the photograph of the defatted rice bran packed column used in the Example of this invention. 本発明の実施例における乾燥脱脂米糠を用いた健康機能成分の吸着試験において、ＴＬＣによる各画の検出結果を示す写真である。It is a photograph which shows the detection result of each image by TLC in the adsorption test of the health functional component using the dry defatted rice bran in the Example of this invention. 本発明の実施例における乾燥脱脂米糠を用いた健康機能成分の吸着・分離溶出試験において、ｎ−ヘキサン・エタノール混合溶媒によるγオリザノールの分離結果を示す写真である。It is a photograph which shows the isolation | separation result of (gamma) orzanol by n-hexane and ethanol mixed solvent in the adsorption | suction and isolation | separation elution test of the health functional component using the dry defatted rice bran in the Example of this invention. 本発明の実施例における乾燥脱脂米糠を用いた健康機能成分の吸着・分離溶出試験において、ｎ−ヘキサン・エタノール混合溶媒（１００：１，ｖ／ｖ）によるγオリザノールの分離結果を示す写真である。It is a photograph which shows the isolation | separation result of (gamma) oryzanol by n-hexane ethanol mixed solvent (100: 1, v / v) in the adsorption | suction and isolation | separation elution test of the health functional component using the dry defatted rice bran in the Example of this invention. . 本発明の実施例における乾燥脱脂米糠に吸着した健康機能成分の溶出・分離条件の試験において、ｐＨ条件による溶出・分離の状況を示す図である。In the Example of this invention, it is a figure which shows the condition of the elution and isolation | separation by pH conditions in the test of the elution / isolation | separation conditions of the health functional component adsorbed to the dry defatted rice bran.

Claims (8)

穀類糠をｎ−ヘキサン又はクロロホルムからなる低極性有機溶媒及びアセトン、メタノール又はエタノールからなる高極性有機溶媒で洗浄し、極性の高い化学物質を吸着する吸着担体として改質した脱脂穀類糠を、乾燥処理することによって調製した乾燥脱脂穀類糠を吸着担体とし、γオリザノール、トコフェロール、及びポリフェノール類から選択される１又は２以上の極性のある健康機能成分を含有する原料から、有機溶媒によって抽出された抽出物を、該乾燥脱脂穀類糠からなる吸着担体によって、中性乃至酸性条件下で非極性有機溶媒を用いて吸着処理することを特徴とするγオリザノール、トコフェロール、及びポリフェノール類から選択される１又は２以上の極性のある健康機能成分が吸着・濃縮された乾燥脱脂穀類糠の製造方法。 The cereal meal is washed with a low-polar organic solvent composed of n-hexane or chloroform and a high-polar organic solvent composed of acetone, methanol or ethanol, and the defatted cereal meal modified as an adsorption carrier for adsorbing a highly polar chemical substance is dried. Extracted with an organic solvent from a raw material containing one or more polar health functional ingredients selected from γ-oryzanol, tocopherol, and polyphenols using dry defatted cereal meal prepared by treatment as an adsorption carrier 1 selected from γ-oryzanol, tocopherol, and polyphenols, wherein the extract is adsorbed with an adsorbent carrier comprising the dried defatted cereal meal using a nonpolar organic solvent under neutral to acidic conditions. Or a method for producing a dried defatted cereal meal with adsorbed and concentrated two or more polar health function ingredients . γオリザノール、トコフェロール、及びポリフェノール類から選択される１又は２以上の極性のある健康機能成分を含有する原料から、有機溶媒によって抽出された抽出物が、米糠或いはコンブから抽出された抽出物であることを特徴とする請求項１に記載のγオリザノール、トコフェロール、及びポリフェノール類から選択される１又は２以上の極性のある健康機能成分が吸着・濃縮された乾燥脱脂穀類糠の製造方法。   An extract extracted from an organic solvent from a raw material containing one or more polar health functional ingredients selected from γ-oryzanol, tocopherol, and polyphenols is an extract extracted from rice bran or kombu. A method for producing a dried defatted cereal meal comprising adsorbed and concentrated one or more polar health functional ingredients selected from γ-oryzanol, tocopherol, and polyphenols according to claim 1. 乾燥脱脂穀類糠が、乾燥脱脂米糠又は乾燥脱脂小麦フスマであることを特徴とする請求項１又は２に記載のγオリザノール、トコフェロール、及びポリフェノール類から選択される１又は２以上の極性のある健康機能成分が吸着・濃縮された乾燥脱脂穀類糠の製造方法。   The dry defatted cereal meal is dry defatted rice bran or dry defatted wheat bran, wherein one or more polar health selected from gamma oryzanol, tocopherol and polyphenols according to claim 1 or 2 is used. A method for producing dry defatted cereal meal with functional components adsorbed and concentrated. 乾燥脱脂穀類糠が、脱脂穀類糠を５０〜１００℃で、１２〜２４時間乾燥処理したものであることを特徴とする請求項１〜３のいずれかに記載のγオリザノール、トコフェロール、及びポリフェノール類から選択される１又は２以上の極性のある健康機能成分が吸着・濃縮された乾燥脱脂穀類糠の製造方法。 The dried defatted cereal meal is obtained by drying the defatted cereal meal at 50 to 100 ° C for 12 to 24 hours, gamma oryzanol, tocopherol and polyphenols according to any one of claims 1 to 3 A method for producing a dried defatted cereal meal wherein 1 or 2 or more polar health function components selected from are adsorbed and concentrated. γオリザノール、トコフェロール、及びポリフェノール類から選択される１又は２以上の極性のある健康機能成分を含有する原料から、有機溶媒によって抽出された抽出物を、乾燥脱脂穀類糠からなる吸着担体によって、非極性有機溶媒を用いて行う吸着処理を、ｎ−ヘキサンを用いて行なうことを特徴とする請求項１〜４のいずれかに記載のγオリザノール、トコフェロール、及びポリフェノール類から選択される１又は２以上の極性のある健康機能成分が吸着・濃縮された乾燥脱脂穀類糠の製造方法。 An extract extracted with an organic solvent from a raw material containing one or more polar health functional ingredients selected from γ-oryzanol, tocopherol, and polyphenols is non- coated with an adsorbent carrier made of dried defatted cereal meal. 1 or 2 or more selected from (gamma) oryzanol, tocopherol, and polyphenols in any one of Claims 1-4 which perform the adsorption process performed using a polar organic solvent using n-hexane A method for producing dried defatted cereal meal with adsorbed and concentrated healthy functional ingredients with polarity. 請求項１〜５のいずれかに記載のγオリザノール、トコフェロール、及びポリフェノール類から選択される１又は２以上の極性のある健康機能成分が吸着・濃縮された乾燥脱脂穀類糠の製造方法を用いて、該乾燥脱脂穀類糠を製造し、該乾燥脱脂穀類糠から、該極性のある健康機能成分を極性の溶出・分離溶媒を用いて中性乃至アルカリ条件下で溶出・分離することを特徴とするγオリザノール、トコフェロール、及びポリフェノール類から選択される１又は２以上の極性のある健康機能成分の濃縮物の製造方法。 Using a method for producing a dried defatted cereal meal with adsorbed and concentrated one or more polar health function components selected from γ-oryzanol, tocopherol, and polyphenols according to any one of claims 1 to 5 , Producing the dried defatted cereal meal, and elution / separation of the polar health functional ingredient from the dried defatted cereal meal under a neutral or alkaline condition using a polar elution / separation solvent A method for producing a concentrate of one or more polar health functional ingredients selected from gamma oryzanol, tocopherol, and polyphenols. 極性の溶出・分離溶媒として、ｎ−ヘキサン・エタノール混合溶媒を用いることを特徴とする請求項６に記載のγオリザノール、トコフェロール、及びポリフェノール類から選択される１又は２以上の極性のある健康機能成分の濃縮物の製造方法。 An n-hexane / ethanol mixed solvent is used as a polar elution / separation solvent, and one or more polar health functions selected from γ-oryzanol, tocopherol and polyphenols according to claim 6 A method for producing an ingredient concentrate. γオリザノール、トコフェロール、及びポリフェノール類から選択される１又は２以上の極性のある健康機能成分の濃縮物が、健康機能成分含有飲食品用、医薬品用、医薬部外品用、化粧品用、動物飼料用、又は水産飼料用の素材であることを特徴とする請求項６又は７に記載のγオリザノール、トコフェロール、及びポリフェノール類から選択される１又は２以上の極性のある健康機能成分の濃縮物の製造方法。
A concentrate of one or more polar health functional ingredients selected from γ-oryzanol, tocopherol, and polyphenols is a health functional ingredient-containing food / drink, pharmaceutical, quasi-drug, cosmetic, animal feed A concentrate of one or more polar health functional ingredients selected from γ-oryzanol, tocopherol, and polyphenols according to claim 6 or 7 , wherein Production method.
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