JP2016003223A - Flavonoid-containing powder composition - Google Patents
Flavonoid-containing powder composition Download PDFInfo
- Publication number
- JP2016003223A JP2016003223A JP2014126232A JP2014126232A JP2016003223A JP 2016003223 A JP2016003223 A JP 2016003223A JP 2014126232 A JP2014126232 A JP 2014126232A JP 2014126232 A JP2014126232 A JP 2014126232A JP 2016003223 A JP2016003223 A JP 2016003223A
- Authority
- JP
- Japan
- Prior art keywords
- flavonoids
- water
- solubility
- powder composition
- flavonoid
- 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
Links
- 229930003935 flavonoid Natural products 0.000 title claims abstract description 90
- 235000017173 flavonoids Nutrition 0.000 title claims abstract description 90
- 150000002215 flavonoids Chemical class 0.000 title claims abstract description 88
- 239000000843 powder Substances 0.000 title claims abstract description 32
- 239000000203 mixture Substances 0.000 title claims abstract description 29
- 235000013325 dietary fiber Nutrition 0.000 claims abstract description 30
- 239000004375 Dextrin Substances 0.000 claims description 36
- 229920001353 Dextrin Polymers 0.000 claims description 36
- 235000019425 dextrin Nutrition 0.000 claims description 36
- 239000007864 aqueous solution Substances 0.000 claims description 18
- DLRVVLDZNNYCBX-UHFFFAOYSA-N Polydextrose Polymers OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(O)O1 DLRVVLDZNNYCBX-UHFFFAOYSA-N 0.000 claims description 16
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- 235000008696 isoflavones Nutrition 0.000 claims description 15
- REFJWTPEDVJJIY-UHFFFAOYSA-N Quercetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 13
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- SATHPVQTSSUFFW-UHFFFAOYSA-N 4-[6-[(3,5-dihydroxy-4-methoxyoxan-2-yl)oxymethyl]-3,5-dihydroxy-4-methoxyoxan-2-yl]oxy-2-(hydroxymethyl)-6-methyloxane-3,5-diol Chemical compound OC1C(OC)C(O)COC1OCC1C(O)C(OC)C(O)C(OC2C(C(CO)OC(C)C2O)O)O1 SATHPVQTSSUFFW-UHFFFAOYSA-N 0.000 claims description 7
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- ZVOLCUVKHLEPEV-UHFFFAOYSA-N Quercetagetin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=C(O)C(O)=C(O)C=C2O1 ZVOLCUVKHLEPEV-UHFFFAOYSA-N 0.000 claims description 7
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- 238000012360 testing method Methods 0.000 description 19
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Abstract
Description
本発明は、フラボノイド類の水溶性が高い粉末組成物に関する。 The present invention relates to a powder composition having high water solubility of flavonoids.
フラボノイド (flavonoid) は天然に存在する有機化合物群で、クマル酸CoAとマロニルCoAが重合してできるカルコンから派生する植物二次代謝物の総称である。いわゆるポリフェノールとも呼ばれる化合物群であり（代表例であり）、アントシアニン、カテキンやフラバンを含む広い概念で、付着する糖のバリエーションを考慮すると7,000以上の構造が知られている。
フラボノイドは次の化学式１で表される基本骨格を有している。
Flavonoids are a group of naturally occurring organic compounds, and are a collective term for plant secondary metabolites derived from chalcone that is formed by polymerization of coumarate CoA and malonyl CoA. It is a group of compounds called so-called polyphenols (representative examples), and is a broad concept including anthocyanins, catechins and flavans, and more than 7,000 structures are known in consideration of the variation of attached sugars.
Flavonoids have a basic skeleton represented by the following chemical formula 1.
フラボノイド化合物は、その基本骨格からフラボン類、イソフラボン類、フラボノール類、フラバノン類、フラバノール類、フラバノノール類、アントシアニジン類に分類される。フラボン類としてはアピゲニン、ルテオリン、タンゲリチン、ジオスミン、フラボキサートなどが知られている。イソフラボン類としては、ダイゼイン、ダイジン、ゲニステインなどが知られている。フラボノール類としては、ケンフェロール、ミリセチン、ケルセチンが知られている。フラバノン類としては、エリオジクチオール、ヘスペレチン、ヘスペリジン、ホモエリオジクチオール、ナリンゲニンが知られている。フラバノール類としては、カテキン、エピカテキン、エピガロカテキンが知られている。フラバノノール類としてはジヒドロケルセチンが知られている。アントシアニジン類としては、シアニジン、デルフィニジン、マルビジン、ペラルゴニジン、ペオニジンが知られている。
これらのフラボノイド化合物は、抗酸化作用や抗菌作用など多様な生理活性を有しているため、健康管理の面から積極的に摂取するように推奨されている。しかしフラボノイド化合物はいずれも水溶性が低く、単なるフラボノイドとして経口摂取してもその大部分が吸収されずに排泄されてしまう。このためフラボノイドの吸収性を高め、生体内での有効性をあげる目的で水溶性を高める技術が提案されている。
フラボノイド類の水溶性を高めるためにもっとも利用される技術は、フラボノイドを配糖体化することである。たとえば、特許文献１にはα−グリコシル化することで難水溶性のフラバノン類に属するヘスペリジンの溶解度を改善する技術が記載されている。特許文献２にはフラバノール類に属するカテキンを配糖体化することで水溶性を改善する技術が開示されている。
またフラボノイド類の溶液中で、フラボノイド類が沈殿しないようにする分散溶液の調製技術が提案されている。特許文献３にはイソフラボンの粒子サイズを10μｍ以下に微粉砕し、これをアラビアガムの水溶液に分散させる技術が提案されている。特許文献４にはケルセチンの分散性を向上するため、ケルセチンの分散水溶液に水溶性・高粘性の食物繊維を添加する技術が記載されている。
Flavonoid compounds are classified according to their basic skeleton into flavones, isoflavones, flavonols, flavanones, flavanols, flavonols, and anthocyanidins. As flavones, apigenin, luteolin, tangerine, diosmin, flavoxate and the like are known. As isoflavones, daidzein, daidzin, genistein and the like are known. Kaempferol, myricetin and quercetin are known as flavonols. As flavanones, eliodictyol, hesperetin, hesperidin, homoeriodictythiol and naringenin are known. As the flavanols, catechin, epicatechin, and epigallocatechin are known. Dihydroquercetin is known as a flavonol. As anthocyanidins, cyanidin, delphinidin, malvidin, pelargonidin, and peonidin are known.
Since these flavonoid compounds have various physiological activities such as an antioxidant action and an antibacterial action, they are recommended to be taken actively from the viewpoint of health care. However, all flavonoid compounds have low water solubility, and even if taken orally as simple flavonoids, most of them are excreted without being absorbed. For this reason, a technique for improving water solubility has been proposed for the purpose of increasing the absorbability of flavonoids and increasing the effectiveness in vivo.
The most utilized technique for increasing the water solubility of flavonoids is to glycosideize flavonoids. For example, Patent Document 1 describes a technique for improving the solubility of hesperidin belonging to poorly water-soluble flavanones by α-glycosylation. Patent Document 2 discloses a technique for improving water solubility by converting catechins belonging to flavanols into glycosides.
In addition, a technique for preparing a dispersion solution that prevents flavonoids from precipitating in a solution of flavonoids has been proposed. Patent Document 3 proposes a technique in which the particle size of isoflavone is finely pulverized to 10 μm or less and dispersed in an aqueous gum arabic solution. Patent Document 4 describes a technique of adding a water-soluble and highly viscous dietary fiber to a quercetin-dispersed aqueous solution in order to improve the dispersibility of quercetin.
本発明は、フラボノイドの水溶性が改善されたフラボノイド含有粉末組成物を提供することを課題とする。 An object of the present invention is to provide a flavonoid-containing powder composition having improved water solubility of flavonoids.
本発明者は、フラボノイドの溶解性について研究を進めたところ、水に難溶性のフラボノイドであるジヒドロケルセチンの溶解性を難消化性デキストリンが改善することを見いだした。さらにこのような作用は各種水溶性食物繊維特有であることを見いだし、本発明を完成させた。 As a result of researches on the solubility of flavonoids, the present inventor has found that indigestible dextrin improves the solubility of dihydroquercetin, which is a poorly soluble flavonoid in water. Furthermore, the present inventors have found that such an action is peculiar to various water-soluble dietary fibers and completed the present invention.
本発明の主な構成は、次のとおりである。
（１）フラボノイド類と水溶性食物繊維を含有する粉末組成物。
（２）フラボノイド類１質量部あたり水溶性食物繊維を０．１〜１０質量部含む（１）に記載の粉末組成物。
（３）水溶性食物繊維が難消化性デキストリン、クラスターデキストリン、α−シクロデキストリン、アラビノガラクタン、ポリデキストロースから選択される１以上の物質である（１）又は（２）に記載の粉末組成物。
（４）フラボノイド類がフラボン類、イソフラボン類、フラボノール類、フラバノン類、フラバノール類、フラバノノール類、アントシアニジン類のいずれかに分類される化合物である（１）〜（３）のいずれかに記載の粉末組成物。
（５）フラボノイド類がケルセチン、ヘスペリジン、イソフラボン類から選択される１以上の物質である（１）〜（４）のいずれかに記載の粉末組成物。
（６）フラボノイド類１質量部あたり水溶性食物繊維を０．１〜１０質量部含む水溶液。
（７）飲料の形態である（６）に記載の水溶液。
（８）（１）〜（５）のいずれかに記載の粉末組成物を配合した飲食品。
（９）フラボノイド含有組成物に難消化性デキストリン、クラスターデキストリン、α−シクロデキストリン、アラビノガラクタン、ポリデキストロースから選択される１以上の物質を添加することを特徴とするフラボノイドの溶解性を改善する方法。
The main configuration of the present invention is as follows.
(1) A powder composition containing flavonoids and water-soluble dietary fiber.
(2) The powder composition as described in (1) containing 0.1 to 10 parts by mass of water-soluble dietary fiber per 1 part by mass of flavonoids.
(3) The powder composition according to (1) or (2), wherein the water-soluble dietary fiber is one or more substances selected from indigestible dextrin, cluster dextrin, α-cyclodextrin, arabinogalactan, and polydextrose .
(4) The powder according to any one of (1) to (3), wherein the flavonoid is a compound classified into any of flavones, isoflavones, flavonols, flavanones, flavanols, flavonols, and anthocyanidins Composition.
(5) The powder composition according to any one of (1) to (4), wherein the flavonoid is one or more substances selected from quercetin, hesperidin, and isoflavones.
(6) An aqueous solution containing 0.1 to 10 parts by mass of water-soluble dietary fiber per 1 part by mass of flavonoids.
(7) The aqueous solution according to (6), which is in the form of a beverage.
(8) Food / beverage products which mix | blended the powder composition in any one of (1)-(5).
(9) To improve the solubility of flavonoids characterized by adding one or more substances selected from indigestible dextrin, cluster dextrin, α-cyclodextrin, arabinogalactan, and polydextrose to a flavonoid-containing composition Method.
フラボノイド類の溶解性が改善した粉末組成物が提供される。また従来困難であった２５℃のフラボノイド類の溶解量が１ｍｇ／ｍｌ以上である水溶液が提供される。さらにまた、本発明によりフラボノイド類の水溶性の改善方法及びフラボノイド類を含む水溶液におけるフラボノイド類の沈殿防止方法が提供される。
またフラボノイド類を高濃度に溶解した飲食品が提供される。
A powder composition having improved flavonoid solubility is provided. Further, an aqueous solution in which the amount of flavonoids dissolved at 25 ° C., which has been difficult in the past, is 1 mg / ml or more is provided. Furthermore, the present invention provides a method for improving water solubility of flavonoids and a method for preventing precipitation of flavonoids in an aqueous solution containing flavonoids.
Moreover, the food / beverage products which melt | dissolved flavonoids in high concentration are provided.
本発明は、フラボノイド類と水溶性食物繊維を含有するフラボノイド類の溶解性が高められた粉末組成物に係る発明である。
本発明に用いるフラボノイド類は、下記化学式（１）（平面構造式）で表される基本骨格を有する化合物でああって、フラボン類としてはアピゲニン、ルテオリン、タンゲリチン、ジオスミン、フラボキサート、イソフラボン類としては、ダイゼイン、ダイジン、ゲニステイン、フラボノール類としては、ケンフェロール、ミリセチン、ケルセチン、フラバノン類としては、エリオジクチオール、ヘスペレチン、ヘスペリジン、ホモエリオジクチオール、ナリンゲニン、フラバノール類としては、カテキン、エピカテキン、エピガロカテキン、フラバノノール類としてはジヒドロケルセチン、アントシアニジン類としては、シアニジン、デルフィニジン、マルビジン、ペラルゴニジン、ペオニジンが例示できる。特に好ましくは、ケルセチン２水和物、ヘスペリジン、イソフラボン類である。なおイソフラボン類は下記の化学式１のピロン環に結合するフェノール基が３位に結合した基本骨格を有する。
The present invention relates to a powder composition in which the solubility of flavonoids containing flavonoids and water-soluble dietary fibers is enhanced.
The flavonoids used in the present invention are compounds having a basic skeleton represented by the following chemical formula (1) (planar structural formula), and examples of flavones include apigenin, luteolin, tangelitin, diosmine, flavoxate, and isoflavones. As daidzein, daidzin, genistein, flavonols, kaempferol, myricetin, quercetin, flavanones as eriodictyol, hesperetin, hesperidin, homoeliodictyol, naringenin, flavanols as catechin, epicatechin, epigallo Examples of catechins and flavonols include dihydroquercetin, and examples of anthocyanidins include cyanidin, delphinidin, malvidin, pelargonidin, and peonidin. Particularly preferred are quercetin dihydrate, hesperidin, and isoflavones. The isoflavones have a basic skeleton in which a phenol group bonded to the pyrone ring of the following chemical formula 1 is bonded to the 3-position.
フラボノイド類は、植物から抽出された粗精製物であっても良いし、高度に精製された精製物であっても良い。一般的には粗精製物のほうが溶解性に劣るといわれている。
フラボノイド類は油溶性の化合物であり、水にはわずかしか溶解しない。例えばフラバノノール類に分類されるジヒドロケルセチンの場合、その溶解度は温度依存性があるが、２５℃における溶解度は１ｍｇ／ｍｌ以下、９０℃における溶解度は５２ｍｇ／ｍｌである。
The flavonoids may be a crude product extracted from a plant or a highly purified product. Generally, it is said that the crudely purified product is inferior in solubility.
Flavonoids are oil-soluble compounds and are only slightly soluble in water. For example, in the case of dihydroquercetin classified into flavonols, the solubility is temperature-dependent, but the solubility at 25 ° C. is 1 mg / ml or less, and the solubility at 90 ° C. is 52 mg / ml.
フラボノイド類を水溶液とするためには、加熱して溶解することで、９０℃の溶解度を５２ｍｇ／ｍｌ以上とすることができる。しかし、この水溶液は温度が低下するとフラボノイド類が析出してしまう。
例えば、市販されているシベリア又は、ダフリアカラマツから抽出したフラボノイド類含有組成物は約８０％のフラボノイドであるジヒドロケルセチンとその他フラボノイド類を含有している粉末（商品名：ジクベルチン 株式会社ＤＨＱ）であるが、この粉末の水への溶解性はきわめて低く、精製されたフラボノイドであるジヒドロケルセチン（タキシフォリン）の２５℃の溶解度である１ｍｇ／ｍｌよりもさらに低い。
フラボノイド類１質量部あたり水溶性食物繊維の粉末を０．１〜１０質量部を均質に混合することで、当該粉末を溶解すると粉末中のフラボノイド類の２５℃における溶解度をフラボノイド類のみを溶解させる場合に比して１．３〜４倍の濃度に改善することができる。
なお、水溶性食物繊維の配合量が０．１質量部以下の場合、溶解性改善効果がなく１０質量％を超えるとフラボノイド類の溶解度が頭打ちとなってしまう。
In order to make flavonoids into an aqueous solution, the solubility at 90 ° C. can be made 52 mg / ml or more by heating and dissolving. However, the flavonoids are precipitated when the temperature of the aqueous solution decreases.
For example, a commercially available flavonoid-containing composition extracted from Siberia or Daphnia larch is a powder containing about 80% flavonoid dihydroquercetin and other flavonoids (trade name: Diqbertin DHQ). However, the solubility of this powder in water is very low, even lower than the 1 mg / ml solubility of the purified flavonoid dihydroquercetin (taxifolin) at 25 ° C.
By mixing 0.1 to 10 parts by mass of water-soluble dietary fiber powder per 1 part by mass of flavonoids, when the powder is dissolved, the solubility of the flavonoids in the powder at 25 ° C. is dissolved only in the flavonoids. The concentration can be improved to 1.3 to 4 times the case.
In addition, when the compounding quantity of water-soluble dietary fiber is 0.1 mass part or less, when there is no solubility improvement effect and it exceeds 10 mass%, the solubility of flavonoids will reach a peak.
本発明で言う水溶性食物繊維としては、グアー豆酵素分解物、グルコマンナン、βグルカン、難消化性デキストリン、難消化性グルカン、ポリデキストロース、イヌリン、アガロース、アルギン酸ナトリウム 、カラギーナン、フコイダン、ポルフィラン、ラミナラン、アラビノガラクタンを例示できる。好ましくは難消化性デキストリン、ポリデキストロース、特に好ましく、難消化性デキストリンが特に好ましい。また広義の水溶性食物繊維である環状構造を持つ高分子デキストリン（商品名：クラスターデキストリン）やシクロデキストリンも本発明に用いることができる。 Examples of the water-soluble dietary fiber in the present invention include guar bean enzyme degradation product, glucomannan, β-glucan, indigestible dextrin, indigestible glucan, polydextrose, inulin, agarose, sodium alginate, carrageenan, fucoidan, porphyran, laminaran And arabinogalactan. Indigestible dextrin and polydextrose are particularly preferred, and indigestible dextrin is particularly preferred. Polymer dextrin having a cyclic structure (trade name: cluster dextrin) and cyclodextrin, which are water-soluble dietary fibers in a broad sense, can also be used in the present invention.
本発明のフラボノイド類及び水溶性食物繊維を含む組成物は、水溶液又は飲料などの水媒体に溶解したとき、水溶液中に溶解するフラボノイド類の２５℃の濃度を１ｍｇ／ｍｌ以上にすることができる。またフラボノイドの濃度を最高で同じく２５℃で４ｍｇ／ｍｌとすることができる。 When the composition containing the flavonoids and water-soluble dietary fiber of the present invention is dissolved in an aqueous medium such as an aqueous solution or a beverage, the concentration of the flavonoids dissolved in the aqueous solution at 25 ° C. can be 1 mg / ml or more. . The flavonoid concentration can also be 4 mg / ml at the same maximum at 25 ° C.
さらにまた、フラボノイド類を高濃度に加温溶解した水溶液又は飲料中に水溶性食物繊維を溶解したフラボノイドの１質量部あたり０．１〜１０質量部添加して、撹拌し溶解させることにより、室温（２５℃）に液温が低下しても、水溶液又は飲料中にフラボノイドが析出することを抑制することができる。 Furthermore, 0.1 to 10 parts by mass per 1 part by mass of flavonoids in which water-soluble dietary fiber is dissolved is added to an aqueous solution or beverage in which flavonoids are heated and dissolved at a high concentration, and the mixture is stirred and dissolved. Even when the liquid temperature is lowered to (25 ° C.), precipitation of flavonoids in the aqueous solution or beverage can be suppressed.
以下に本発明の効果を確認した試験例を示し、本発明をさらに具体的に説明する。 Test examples confirming the effects of the present invention will be shown below, and the present invention will be described more specifically.
試験例
＜試験例１：フラボノイド類の溶解度の指標としての吸光度測定（予備試験）＞
フラボノイド類の溶解度の指標として吸光度を使用可能か否か評価した。
１．試験方法
フラボノイドの水溶液は、その基本骨格の２重結合構造に由来する黄色〜赤〜青の可視部及び紫外部に極大吸収を持つ透明な水溶液となる。主なフラボノイド類の吸収波長を表１に示す。
Test example <Test example 1: Absorbance measurement as an index of solubility of flavonoids (preliminary test)>
It was evaluated whether or not absorbance can be used as an indicator of the solubility of flavonoids.
1. Test Method An aqueous solution of flavonoid is a transparent aqueous solution having maximum absorption in the visible part and the ultraviolet part of yellow to red to blue derived from the double bond structure of the basic skeleton. Table 1 shows the absorption wavelengths of main flavonoids.
15mL遠沈管にフラボノイド類の一種であるシベリア又は、ダフリアカラマツから抽出したジヒドロケルセチン粉末（ラビトール：株式会社アメティス）及び難消化性デキストリン（ファイバーソル２：松谷化学工業株式会社製）を秤量し、蒸留水を5gとなるように加えた。転倒混和したのち、卓上超音波洗浄機(SHARP社製 UT-205)で10分間ソニケーションした後、25℃で1時間保温した。
HITACHI社製Himac CT6Dを使用し、3000rpmで10分間遠心分離した後、上清を2mLマイクロチューブ（エッペンドルフ社製）に移し、16200Gで10分間超遠心分離した(HITACHI社製CF15RX II)。上清を新しいマイクロチューブに移し、SHIMADZU社製UV-2450で波長400nmから200nmの紫外部波長域の吸光度を測定し、スペクトログラフィーを得た。
Weigh Siberia, a kind of flavonoids, or dihydroquercetin powder (Rabitol: Ametis Co., Ltd.) and indigestible dextrin (Fibersol 2: made by Matsutani Chemical Co., Ltd.) Distilled water was added to 5 g. After mixing by inversion, sonication was performed for 10 minutes with a tabletop ultrasonic cleaner (UT-205 manufactured by SHARP), and the mixture was kept at 25 ° C. for 1 hour.
After HITACHI Himac CT6D was centrifuged at 3000 rpm for 10 minutes, the supernatant was transferred to a 2 mL microtube (Eppendorf) and ultracentrifuged at 16200 G for 10 minutes (HITACHI CF15RX II). The supernatant was transferred to a new microtube, and the absorbance in the ultraviolet wavelength region from 400 nm to 200 nm was measured with UV-2450 manufactured by SHIMADZU to obtain a spectrograph.
２．結果
図１にジヒドロケルセチンを定量とし、難消化性デキストリンを増加させた際に得られるスペクトロメトリーを示す。
難消化性デキストリンによってジヒドロケルセチンの溶解性が上昇し、吸光度が上昇することが確認できた。
2. Results FIG. 1 shows the spectrometry obtained when dihydroquercetin is used as a quantitative amount and the indigestible dextrin is increased.
It was confirmed that the indigestible dextrin increased the solubility of dihydroquercetin and increased the absorbance.
＜試験例２：フラボノイド類の溶解度改善試験＞
１．試験方法
フラボノイド類としてジヒドロケルセチン（ジクベルチン：株式会社ＤＨＱ）を用い、これに難消化性デキストリン（ファイバーソル２：松谷化学工業株式会社製）を用いてフラボノイド類の溶解度に及ぼす難消化性デキストリンの効果を評価した。
下記表２の比率でフラボノイド類と難消化性デキストリンの粉末を混合し、予備試験と同様にして試験溶液を調整し、400から200nmの波長域の吸光度を測定した。
<Test Example 2: Solubility improvement test of flavonoids>
1. Test method The effect of indigestible dextrin on the solubility of flavonoids using dihydroquercetin (dicubertin: DHQ) as flavonoids and using indigestible dextrin (Fibersol 2: manufactured by Matsutani Chemical Industry Co., Ltd.) Evaluated.
Flavonoids and indigestible dextrin powder were mixed in the ratios shown in Table 2 below, and the test solution was prepared in the same manner as in the preliminary test, and the absorbance in the wavelength range of 400 to 200 nm was measured.
難消化性デキストリンを含まない場合の溶液の極大波長における吸光度比を１とし、難消化性デキストリンを添加した際の相対吸光度（吸光度比）を求めた。 The relative absorbance (absorbance ratio) when the indigestible dextrin was added was determined with the absorbance ratio at the maximum wavelength of the solution in the case of containing no indigestible dextrin being 1.
２．結果
表２に示すとおり難消化性デキストリンを含まない溶液の吸光度比を１とすると難消化性デキストリンの添加量が増大するにつれ、溶解度が上昇した。２５℃の温度での水へのフラボノイドの溶解度は１ｍｇ／ｍｌとされている。難消化性デキストリンを添加することで、無添加の４倍量、４ｍｇ／ｍｌの濃度のフラボノイド水溶液を得ることができた。
2. Results As shown in Table 2, when the absorbance ratio of the solution containing no indigestible dextrin was 1, the solubility increased as the amount of the indigestible dextrin increased. The solubility of flavonoids in water at a temperature of 25 ° C. is 1 mg / ml. By adding the non-digestible dextrin, an flavonoid aqueous solution having a concentration of 4 times the amount of additive-free dextrin and 4 mg / ml could be obtained.
＜試験例３：各種多糖類のフラボノイドの溶解度に及ぼす効果＞
１．試験方法
水溶性食物繊維として試験例１、２で用いた難消化性デキストリンとは平均分子量の異なる難消化性デキストリン（パインファイバーＣ：松谷化学工業株式会社製）、ポリデキストロース（スターライトIII：Ｔａｔｅ＆Ｌｙｌｅ製）、アラビノガラクタン（レジストエイド：ロンザジャパン製）、環状構造を持つ高分子デキストリン（クラスターデキストリン：グリコ栄養食品株式会社製）、非水溶性食物繊維としてセルロース（セオラスFD-301：旭化成ケミカルズ株式会社製）、トウモロコシ澱粉（コーンスターチ：松谷化学工業株式会社製）、α−シクロデキストリン（ＣＡＶＡＭＡＸ（登録商標）ｗ６：株式会社シクロケム製）それぞれ１２５ｍｇをフラボノイド粉末（ジクベルチン）１２５ｍｇに粉混合した。それぞれの粉末を15mL遠沈管採取し、蒸留水を5gとなるように加えた。転倒混和したのち、卓上超音波洗浄機(SHARP社製 UT-205)で10分間ソニケーションした後、25℃で1時間保温した。次いで、HITACHI社製Himac CT6Dを使用し、3000rpmで10分間遠心分離した後、上清を2mLマイクロチューブ（エッペンドルフ社製）に移し、16200Gで10分間超遠心分離した(HITACHI社製CF15RX II)。上清を新しいマイクロチューブに移し、SHIMADZU社製UV-2450で波長400から200nmの波長域の吸光度を測定し、試験例１と同様にフラボノイド類の溶解性を試験した。
<Test Example 3: Effects of various polysaccharides on the solubility of flavonoids>
1. Test Method As a water-soluble dietary fiber, an indigestible dextrin having different average molecular weight from that of the indigestible dextrin used in Test Examples 1 and 2 (Pine Fiber C: manufactured by Matsutani Chemical Co., Ltd.), polydextrose (Starlite III: Tate & Lyle) ), Arabinogalactan (resist aid: manufactured by Lonza Japan), polymer dextrin having a cyclic structure (cluster dextrin: manufactured by Glico Nutrition Foods Co., Ltd.), cellulose as water-insoluble dietary fiber (Ceolus FD-301: Asahi Kasei Chemicals Corporation) 125 mg each of corn starch (Corn Starch: made by Matsutani Chemical Industry Co., Ltd.) and α-cyclodextrin (CVAMAX (registered trademark) w6: made by Cyclochem) were mixed with 125 mg of flavonoid powder (Dicvertine). Each powder was collected from a 15 mL centrifuge tube, and distilled water was added to 5 g. After mixing by inversion, sonication was performed for 10 minutes with a tabletop ultrasonic cleaner (UT-205 manufactured by SHARP), and the mixture was kept at 25 ° C. for 1 hour. Next, after HITACHI Himac CT6D was used and centrifuged at 3000 rpm for 10 minutes, the supernatant was transferred to a 2 mL microtube (Eppendorf) and ultracentrifuged at 16200 G for 10 minutes (HITACHI CF15RX II). The supernatant was transferred to a new microtube, and the absorbance in the wavelength region of 400 to 200 nm was measured with UV-2450 manufactured by SHIMADZU, and the solubility of flavonoids was tested in the same manner as in Test Example 1.
２．試験結果
試験結果を表３に示す。
2. Test results The test results are shown in Table 3.
水溶性食物繊維である難消化性デキストリン（パインファイバー）、環状高分子デキストリン（クラスターデキストリン）、α−シクロデキストリン、アラビノガラクタン、ポリデキストロースはフラボノイド類の溶解性を改善した。しかし非水溶性食物繊維であるセルロース及び非食物繊維であるトウモロコシ澱粉はフラボノイド類の溶解性を悪化させた。
以上の試験例１〜３により、水溶性食物繊維はフラボノイド類の水への溶解性を改善することが明らかとなった。またフラボノイド類の溶解度は、水溶性食物繊維の混合量に応じて改善することが判明した。
Indigestible dextrin (pine fiber), cyclic polymer dextrin (cluster dextrin), α-cyclodextrin, arabinogalactan, and polydextrose, which are water-soluble dietary fibers, improved the solubility of flavonoids. However, cellulose, which is a water-insoluble dietary fiber, and corn starch, which is a non-dietary fiber, worsened the solubility of flavonoids.
From the above Test Examples 1 to 3, it became clear that the water-soluble dietary fiber improves the solubility of flavonoids in water. Moreover, it became clear that the solubility of flavonoids improved according to the mixing amount of water-soluble dietary fiber.
＜試験例４：各種のフラボノイド類の溶解度改善試験＞
フラボノイド類としてケルセチン（フラボノール類）、ヘスペリジン（フラバノン類）、イソフラボン（イソフラボン類）を用い、水溶性食物繊維として難消化性デキストリンを用いて、フラボノイド類の溶解性改善作用を確認した。
１．試験方法
フラボノイド類として以下のものを用いた。
ケルセチン２水和物（マメ科エンジュ由来：メディエンス株式会社製）、ヘスペリジン（柑橘類皮果実由来；株式会社中原製）、イソフラボン（大豆由来イソフラボン類混合物；株式会社中原製）
また水溶性食物繊維として難消化性デキストリン（ファイバーソル２：松谷化学工業株式会社製）を用いた。
それぞれ１２５ｍｇのフラボノイド類粉末と水溶性食物繊維１２５ｍｇを粉混合した。それぞれの粉末を15mL遠沈管採取し、蒸留水を5gとなるように加えた。転倒混和したのち、卓上超音波洗浄機(SHARP社製 UT-205)で10分間ソニケーションした後、25℃で1時間保温した。次いで、HITACHI社製Himac CT6Dを使用し、3000rpmで10分間遠心分離した後、上清を2mLマイクロチューブ（エッペンドルフ社製）に移し、16200Gで10分間超遠心分離した(HITACHI社製CF15RX II)。上清を新しいマイクロチューブに移し、SHIMADZU社製UV-2450で400から200nmの波長域の吸光度を測定し、フラボノイドのみを溶解させた溶液を対照として、試験例１と同様にフラボノイド類の溶解性を試験した。
<Test Example 4: Solubility improvement test of various flavonoids>
Using quercetin (flavonols), hesperidin (flavanones), and isoflavones (isoflavones) as flavonoids, and an indigestible dextrin as a water-soluble dietary fiber, the effect of improving the solubility of flavonoids was confirmed.
1. Test Method The following were used as flavonoids.
Quercetin dihydrate (from legume Enju: manufactured by Medience Corporation), hesperidin (derived from citrus peel fruit; manufactured by Nakahara Co., Ltd.), isoflavone (mixed soybean-derived isoflavones; manufactured by Nakahara Co., Ltd.)
Indigestible dextrin (Fiber Sol 2: manufactured by Matsutani Chemical Industry Co., Ltd.) was used as a water-soluble dietary fiber.
Each 125 mg of flavonoid powder and 125 mg of water-soluble dietary fiber were mixed. Each powder was collected from a 15 mL centrifuge tube, and distilled water was added to 5 g. After mixing by inversion, sonication was performed for 10 minutes with a tabletop ultrasonic cleaner (UT-205 manufactured by SHARP), and the mixture was kept at 25 ° C. for 1 hour. Next, after HITACHI Himac CT6D was used and centrifuged at 3000 rpm for 10 minutes, the supernatant was transferred to a 2 mL microtube (Eppendorf) and ultracentrifuged at 16200 G for 10 minutes (HITACHI CF15RX II). Transfer the supernatant to a new microtube, measure the absorbance in the wavelength range from 400 to 200 nm with UV-2450 manufactured by SHIMADZU, and use the solution in which only the flavonoids are dissolved as a control. Solubility of flavonoids as in Test Example 1 Was tested.
２．試験結果
試験結果を表４に示す。
2. Test results The test results are shown in Table 4.
ケルセチン、ヘスペリジン、イソフラボンの各フラボノイドの溶解性は、難消化性デキストリンと粉混合することでいずれも１７％〜１２４０％以上改善した。特にヘスペリジンはその効果が顕著であった。 The solubility of each flavonoid of quercetin, hesperidin, and isoflavone was improved by 17% to 1240% or more by powder mixing with indigestible dextrin. In particular, the effect of hesperidin was remarkable.
以上の試験例１〜４からフラボノイド類は、水溶性食物繊維と粉混合するだけでその溶解性が改善することが明らかとなった。水溶性食物繊維とフラボノイド類を溶解させた水溶液は超遠心によっても溶解度が低下しないので、分散状態ではなく溶解状態であることが明らかとなった。 From the above Test Examples 1 to 4, it has been clarified that the flavonoids are improved in solubility only by mixing powder with water-soluble dietary fiber. An aqueous solution in which water-soluble dietary fiber and flavonoids are dissolved does not decrease in solubility even by ultracentrifugation, so that it is clear that the solution is not in a dispersed state but in a dissolved state.
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