JP2021127338A - Composition containing lignan compound dissolved in essential oil - Google Patents
Composition containing lignan compound dissolved in essential oil Download PDFInfo
- Publication number
- JP2021127338A JP2021127338A JP2021019192A JP2021019192A JP2021127338A JP 2021127338 A JP2021127338 A JP 2021127338A JP 2021019192 A JP2021019192 A JP 2021019192A JP 2021019192 A JP2021019192 A JP 2021019192A JP 2021127338 A JP2021127338 A JP 2021127338A
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- JP
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- Prior art keywords
- oil
- sesamin
- composition
- sesamolin
- essential
- 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.)
- Pending
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Abstract
Description
セサミン等のリグナン類化合物は、コレステロール低下作用（非特許文献１）、抗高血圧作用（非特許文献２，３）、抗酸化作用（非特許文献４）、肝臓保護作用（非特許文献５）、肝臓がん予防作用（非特許文献６）、乳がん発生抑制作用（非特許文献７）、免疫賦活作用（非特許文献８）などが報告されている。
Lignan compounds such as sesamine have a cholesterol lowering effect (Non-Patent Document 1), an antihypertensive effect (Non-Patent
セサミンは脂溶性であり、油脂類に溶解するといわれているが、実際には一般的な食用油には１％程度しか溶解しない。従って販売されているセサミン製剤は、セサミン含有量を減らすことで食用油脂に溶解させるか、セサミンを分散もしくは懸濁させている。前者ではカプセル１粒あたりの成分含有量が低含量となり、後者ではカプセル内溶液が不透明になるため外見が美しくなくなるため消費者への訴求力が下がる。前者の例として、サントリー株式会社の「セサミンＥＸ」は透明な内容液のソフトカプセルが挙げられる。当該ソフトカプセルは、米胚芽油を用いて１粒３７０ｍｇあたりセサミン３．３ｍｇを溶解させ、カプセル内溶液中におけるセサミンの配合割合は０．８９％である。また、かどや製油株式会社の「ごまセサミン」も透明な内容液のソフトカプセルであり、ゴマ油を用いて１粒の内容液２０ｍｇあたりセサミン５ｍｇを溶解させ、カプセル内容液には２．５％のセサミンが溶解している。後者の例としては、ニチエー株式会社の「黒ごま セサミン サプリメント９０粒」が挙げられる。これは白色皮膜のソフトカプセルであり、ゴマ油に植物レシチンを用いて１粒２００ｍｇあたりセサミン１５ｍｇが懸濁している。また、株式会社オーガランドの「セサミンカプセル」は黄色皮膜のソフトカプセルであり、ゴマ油に乳化剤とミツロウを配合することで１粒２００ｍｇあたりセサミン１０ｍｇが懸濁している。 Sesamin is fat-soluble and is said to dissolve in fats and oils, but in reality, it dissolves only about 1% in general cooking oil. Therefore, the sesamin preparations on the market are dissolved in edible fats and oils by reducing the sesamin content, or sesamin is dispersed or suspended. In the former case, the content of ingredients per capsule is low, and in the latter case, the solution in the capsule becomes opaque and the appearance becomes unattractive, which reduces the appeal to consumers. As an example of the former, Suntory Limited's "Sesamin EX" is a soft capsule with a transparent content liquid. In the soft capsule, 3.3 mg of sesamin is dissolved per 370 mg of each grain using rice germ oil, and the mixing ratio of sesamin in the solution in the capsule is 0.89%. In addition, Kadoya Sesame Co., Ltd.'s "sesame sesamin" is also a soft capsule with a transparent content solution. Using sesame oil, 5 mg of sesamin is dissolved per 20 mg of the content solution, and 2.5% sesamin is contained in the capsule content solution. It is dissolved. An example of the latter is "90 black sesame sesamin supplements" from Nichie Co., Ltd. This is a soft capsule with a white film, and 15 mg of sesamin is suspended per 200 mg of each grain using vegetable lecithin in sesame oil. In addition, "Sesamin Capsule" of Organland Co., Ltd. is a soft capsule with a yellow film, and by blending an emulsifier and beeswax with sesame oil, 10 mg of sesamin is suspended per 200 mg of each grain.
セサミンを溶解することができる食用油脂は中鎖脂肪酸（ＭＣＴ：Ｍｅｄｉｕｍ Ｃｈａｉｎ Ｔｒｉｇｌｙｃｅｒｉｄｅ）が広く知られている（特許文献１）。それに加え、セサミンと組み合わせることで生物学的利用率を上昇することを目的としてγ−オリザノールと米胚芽油（特許文献２）、エピガロカテキンガレート（特許文献３）、ケルセチン（特許文献４）を配合した例も存在する。しかしながら、これらの配合を用いてもカプセル内容液の透明性を保ったままでセサミン濃度を上げることは難しく、セサミンを含有するカプセル内溶液を透明に保てる濃度はカプセル内溶液中１〜２．５％程度であった。 Medium-chain fatty acids (MCT: Medium Chain Triglyceride) are widely known as edible fats and oils capable of dissolving sesamin (Patent Document 1). In addition, γ-oryzanol and rice germ oil (Patent Document 2), epigallocatechin gallate (Patent Document 3), and quercetin (Patent Document 4) were added for the purpose of increasing the biological utilization rate by combining with sesamin. There are also examples of compounding. However, even with these formulations, it is difficult to increase the sesamin concentration while maintaining the transparency of the capsule content, and the concentration that can keep the sesamin-containing in-capsule solution transparent is 1 to 2.5% in the capsule solution. It was about.
そのため、カプセル１粒あたりの成分含有量が低含量となり、その結果経口摂取するカプセル数が増加してコスト高の要因となると同時に、摂取カプセル数が多くなりすぎるため利用者に負担を強いるものであった。 Therefore, the content of ingredients per capsule becomes low, and as a result, the number of capsules to be ingested increases, which causes a high cost. At the same time, the number of capsules ingested becomes too large, which imposes a burden on the user. there were.
先に述べた通り、カプセル内容液の透明性を保ったままセサミンを高濃度に溶解させることができないため、セサミン粉末を分散もしくは懸濁させてセサミンを多量に含有させた外観不透明な組成物とするか、或いは１粒当たりのセサミン含有量を減らしてセサミンを溶解させた透明な組成物とするかのいずれかの方法を取らざるを得なかった。すなわち、透明性を維持しつつ１粒当たりのセサミンを高濃度に溶解させた組成物、好ましくはカプセル剤が求められている。 As described above, since sesamin cannot be dissolved at a high concentration while maintaining the transparency of the capsule content, the composition is opaque in appearance and contains a large amount of sesamin by dispersing or suspending sesamin powder. Either this was done, or the sesamin content per grain was reduced to a transparent composition in which sesamin was dissolved. That is, there is a demand for a composition in which sesamin per grain is dissolved at a high concentration while maintaining transparency, preferably a capsule.
様々な溶媒のスクリーニングを実施し、セサミンを含むリグナン類化合物を精油に溶解させることで、組成物、例えばカプセル内容液の透明性を維持しつつ、セサミンを高濃度に溶解させることを見出すことが出来、本発明を完成させた。 By conducting screening of various solvents and dissolving lignan compounds containing sesamin in essential oils, it is possible to find that sesamin can be dissolved in a high concentration while maintaining the transparency of the composition, for example, the capsule content. The present invention was completed.
すなわち、本発明は、下記の通りである。
（１）セサミンを含むリグナン類化合物を、精油に溶解して含有する組成物。
（２）さらに、セサモリンを含む（１）に記載の組成物
（３）前記精油が、フェニルプロパノイド、ビサボラン型セスキテルペンケトン及びメンタン型ケトンからなる群から選択される１種以上である、（１）または（２）に記載の組成物。
（４）前記精油がクローブオイル、カッシャオイル、クミンシードオイル、ターメリックオイル、スペアミントオイル、ディルシードオイル、ダバナオイル、タラゴンオイル、タイムオイル、バジルオイル、フェンネルオイル、スターアニスオイル、及びセージオイルからなる群から選択される１種以上である、（１）〜（３）のいずれかに記載の組成物。
（５）前記組成物中に溶解したセサミンの濃度が２〜３５質量％である、（１）〜（４）のいずれかに記載の組成物。
（６）紫外・可視分光光度計の７５０ ｎｍの透過度で評価した透明性が８０％以上である、（１）〜（５）のいずれかに記載の組成物。
（７）カプセル剤の形態である、（１）〜（６）のいずれかに記載の組成物。
（８）（１）〜（７）のいずれかに記載の組成物を含有する飲食品。
（９）セサミンを含むリグナン類化合物を精油に溶解させる方法であって、セサモリンを精油にさらに含有する方法。
（１０）前記精油が、クローブオイル、カッシャオイル、クミンシードオイル、ターメリックオイル、スペアミントオイル、ディルシードオイル、ダバナオイル、タラゴンオイル、タイムオイル、バジルオイル、フェンネルオイル、スターアニスオイル及びセージオイルからなる群から選択される１種以上である、（９）に記載の方法。
（１１）セサミン：セサモリンの質量比が１：０．５〜１．５である、（９）または（１０）に記載の方法。
（１２）ＭＣＴ中におけるセサミンを含むリグナン類化合物の溶解性を高める方法であって、セサミンとセサモリンの質量比が１：０．５〜１．５となる量のセサモリンを含有する方法。
（１３）セサミンの血中濃度又は脳内濃度を増加させる方法であって、（１）〜（７）のいずれかに記載の組成物を用いる方法。
（１４）精油を有効成分として含有する、リグナン類化合物の溶解促進剤。
（１５）前記精油が、フェニルプロパノイド、ビサボラン型セスキテルペンケトン及びメンタン型ケトンからなる群から選択される１種以上である、（１４）に記載の溶解促進剤。
（１６）前記精油がクローブオイル、カッシャオイル、クミンシードオイル、ターメリックオイル、スペアミントオイル、ディルシードオイル、ダバナオイル、タラゴンオイル、タイムオイル、バジルオイル、フェンネルオイル、スターアニスオイル、及びセージオイルからなる群から選択される１種以上である、（１４）又は（１５）の記載の溶解促進剤。
That is, the present invention is as follows.
(1) A composition containing a lignan compound containing sesamin dissolved in an essential oil.
(2) The composition according to (1) containing sesamolin (3) The essential oil is at least one selected from the group consisting of phenylpropanoids, bisabolan-type sesquiterpene ketones and menthan-type ketones. The composition according to 1) or (2).
(4) The essential oil consists of clove oil, cashier oil, cumin seed oil, turmeric oil, spare mint oil, dill seed oil, davana oil, taragon oil, thyme oil, basil oil, fennel oil, star anis oil, and sage oil. The composition according to any one of (1) to (3), which is one or more selected.
(5) The composition according to any one of (1) to (4), wherein the concentration of sesamin dissolved in the composition is 2 to 35% by mass.
(6) The composition according to any one of (1) to (5), wherein the transparency evaluated by the ultraviolet / visible spectrophotometer at 750 nm transmittance is 80% or more.
(7) The composition according to any one of (1) to (6), which is in the form of a capsule.
(8) A food or drink containing the composition according to any one of (1) to (7).
(9) A method for dissolving a lignan compound containing sesamin in an essential oil, in which sesamin is further contained in the essential oil.
(10) The essential oil consists of clove oil, cashier oil, cumin seed oil, turmeric oil, spare mint oil, dill seed oil, davana oil, taragon oil, thyme oil, basil oil, fennel oil, star anis oil and sage oil. The method according to (9), which is one or more selected.
(11) The method according to (9) or (10), wherein the mass ratio of sesamin: sesamolin is 1: 0.5 to 1.5.
(12) A method for increasing the solubility of a lignan compound containing sesamin in MCT, which contains an amount of sesamin in which the mass ratio of sesamin and sesamolin is 1: 0.5 to 1.5.
(13) A method for increasing the blood concentration or the brain concentration of sesamin, wherein the composition according to any one of (1) to (7) is used.
(14) A dissolution accelerator for a lignan compound containing an essential oil as an active ingredient.
(15) The dissolution accelerator according to (14), wherein the essential oil is at least one selected from the group consisting of phenylpropanoids, bisabolan-type sesquiterpene ketones, and menthan-type ketones.
(16) The essential oil consists of clove oil, cashier oil, cumin seed oil, turmeric oil, spare mint oil, dill seed oil, davana oil, taragon oil, thyme oil, basil oil, fennel oil, star anis oil, and sage oil. The dissolution accelerator according to (14) or (15), which is one or more selected.
本発明は、従来の分散及び懸濁して製剤化したセサミンを含有する製剤や、食用油に溶解させて製剤化したセサミンを含有する製剤と比較して、組成物の透明度を維持したまま粒あたりの成分摂取量を増加させて、経口摂取する量を減らすことができる。これにより、コストを削減することができる。本発明の組成物を摂取することで、生物学的利用率が向上させることができる。また、セサモリンを含むリグナン類化合物を精油に溶解させることで、精油中におけるセサミンの溶解性を高めることができる。 The present invention is compared with the conventional preparation containing sesamin which is dispersed and suspended and formulated, and the preparation containing sesamin which is dissolved and formulated in edible oil, while maintaining the transparency of the composition per grain. Ingredient intake can be increased to reduce oral intake. As a result, the cost can be reduced. By ingesting the composition of the present invention, the bioavailability can be improved. Further, by dissolving a lignan compound containing sesamolin in an essential oil, the solubility of sesamin in the essential oil can be enhanced.
＜リグナン類化合物＞
本発明においては、リグナン類化合物とはフェニルプロパノイドの一種であり、植物由来ジベンジルブタン骨格に由来するポリフェノール化合物である。リグナン類化合物はアカゴマ（亜麻仁）やゴマ、アブラナ属野菜から抽出され、場合によっては精製されたものを用いることができる。例としてセサミノール、ピノレジノール、シリンガレシノール、セサミン、セサモリン、ラリシレシノール、セコイソラリシレシノール、マタイレシノール、ヒドロキシマタイレシノールが挙げられる。
<Lignan compounds>
In the present invention, the lignan compound is a kind of phenylpropanoid and is a polyphenol compound derived from a plant-derived dibenzylbutane skeleton. Lignan compounds can be extracted from red sesame (flaxseed), sesame, and Brassica vegetables, and in some cases purified. Examples include sesaminol, pinoresinol, siringalesinol, sesamin, sesamolin, lariciresinol, secoisolariciresinol, matairesinol, hydroxymatairesinol.
上述のように、リグナン類化合物は、コレステロール低下作用、抗高血圧作用、抗酸化作用、肝臓保護作用、肝臓がん予防作用、乳がん発生抑制作用、免疫賦活作用などが報告されている。現在販売されている多くのセサミン含有ソフトカプセルは、１日のセサミン摂取量を１０〜１５ｍｇと設定している。実際、セサミンを１０ｍｇとビタミンＥを配合するソフトカプセルを、疲労を強く感じる人に８週間継続摂取したところ、疲労、美容、睡眠に関して有意な改善が認められ、ＬＤＬ ｏｘｉｄａｔｉｏｎ ｌａｇ ｔｉｍｅが高まり血中の抗酸化性が高まるとの報告がある。（Ｇｌｏｂ． Ｊ． Ｈｅａｌｔｈ Ｓｃｉ．，２０１５；７：１−１０）。 As described above, lignan compounds have been reported to have a cholesterol-lowering effect, an antihypertensive effect, an antioxidant effect, a liver protective effect, a liver cancer preventive effect, a breast cancer development inhibitory effect, an immunostimulatory effect and the like. Many sesamin-containing soft capsules currently on the market set the daily intake of sesamin to 10 to 15 mg. In fact, when a soft capsule containing 10 mg of sesamin and vitamin E was continuously ingested for 8 weeks in a person who strongly felt fatigue, significant improvement was observed in fatigue, beauty, and sleep, and the LDL oxidation lag time increased and blood resistance was increased. There are reports that oxidative properties increase. (Glob. J. Health Sci., 2015; 7: 1-10).
＜セサミン＞
セサミンはゴマ油やサンショウに多く含有するリグナン類化合物であり、次に示す構造式を持つ。
セサミンの構造式
<Sesamin>
Sesamin is a lignan compound that is abundant in sesame oil and Japanese pepper, and has the following structural formula.
Structural formula of sesamin
＜セサモリン＞
セサモリンはセサミンと同様にゴマ油やサンショウに多く含有することができるリグナン類化合物であり、次に示す構造式を持つ。
セサモリンの構造式
<Sesamolin>
Like sesamin, sesamolin is a lignan compound that can be contained in a large amount in sesame oil and Japanese pepper, and has the following structural formula.
Structural formula of sesamolin
＜ゴマ抽出物＞
本発明の組成物（以下、「リグナン類化合物を精油に溶解して含有する組成物」、「カプセル内溶液組成物」、「上清組成物」も、「本発明の組成物」に含まれる。）に用いるリグナン類化合物は、セサミンを含有し、ゴマ油等の食品由来の素材から抽出及び／又は精製により得られるセサミン類濃縮物、例えばゴマ抽出物を用いるのが好ましい。本発明の組成物は、セサモリンを含有することが好ましい。セサモリンは、ゴマ油等の食品由来の素材に含まれるものの他、更に追加して添加することができる。
ゴマ種子におけるセサミン、セサモリン濃度は既報（Ｂｕｌｌ． Ｎａｔｌ． Ｉｎｓｔ． Ｃｒｏｐ Ｓｃｉ．， ２００８；９：２７−６１）に記載されている。当該文献より引用すると、ゴマ種子に含まれるセサミン：セサモリン濃度比は品種によって異なる。例えば、ゴマ抽出物ＡＫＹ−２８８３（稲畑香料株式会社）におけるセサミン・セサモリン濃度は、セサミン８２．３％、セサモリン１．６％、ＡＫＹ−２８８４（稲畑香料株式会社）はセサミン６７．５％、セサモリン１８．４％、ＡＫＹ−２８８５（稲畑香料株式会社）は、セサミン３９．７％、セサモリン４６．５％、ＡＫＹ−２８８６（稲畑香料株式会社）は、セサミン４９．０％、セサモリン４５．０％である。
<Sesame extract>
The composition of the present invention (hereinafter, "composition containing a lignan compound dissolved in essential oil", "in-capsule solution composition", and "supernatant composition" is also included in the "composition of the present invention". The lignan compound used in ()) contains sesamine, and it is preferable to use a sesamine concentrate obtained by extraction and / or purification from a food-derived material such as sesame oil, for example, a sesame extract. The composition of the present invention preferably contains sesamolin. Sesamolin can be added in addition to those contained in food-derived materials such as sesame oil.
The concentrations of sesamin and sesamolin in sesame seeds are described in a previous report (Bull. Natl. Inst. Crop Sci., 2008; 9: 27-61). Citing from this document, the sesamin: sesamolin concentration ratio contained in sesame seeds varies depending on the variety. For example, the concentrations of sesamin and sesamolin in the sesame extract AKY-2883 (Inahata Fragrance Co., Ltd.) are 82.3% sesamin and 1.6% sesamolin, and AKY-2884 (Inahata Fragrance Co., Ltd.) is 67.5% sesamin and sesamolin. 18.4%, AKY-2885 (Inahata Fragrance Co., Ltd.) is sesamin 39.7%, sesamolin 46.5%, AKY-2886 (Inahata Fragrance Co., Ltd.) is sesamin 49.0%, sesamolin 45.0% Is.
＜精油＞
本発明において、リグナン類化合物は精油に溶解して使用する。
精油は、フェニルプロパノイド、ビサボラン型セスキテルペンケトンおよびメンタン型ケトンの内の少なくともいずれか１種以上であることが好ましい。
フェニルプロパノイドは、フェニルアラニンを起源とする１−フェニルプロパンが複数縮合した化合物やそれらの誘導体である。例としてクマル酸、ケイ皮酸、コーヒー酸、オイゲノール、アネトール、エストラゴール、チモール、アピオール、シナピルアルコール、フェルラ酸、セサミン等リグナン類化合物が挙げられる。それらを豊富に含有する精油としてカッシャオイル、クローブリーフオイル、クローブバッドオイル、アニスオイル、フェンネルオイル、タラゴンオイル、タイムオイル、パセリシードオイル、バジルオイル、トウシキミ（スターアニス）オイル、ゴマオイルが挙げられる。
ビサボラン型セスキテルペンケトンはイソプレン三分子が縮合した単環式セスキテルペンの一部である。単環式セスキテルペンは環の形状と官能基の位置によってビサボラン型、ゲルマクラン型、エレマン型、フムラン型に分類されるが、ビサボラン型骨格は六員環を一つ有し、その環より２，６−ジメチルヘキシル基を有する。そのビサボラン型セスキテルペンのうちカルボニル基を有する化合物がビサボラン型セスキテルペンケトンである。例として、α−ビサボレン、β−ビサボレン、γ−ビサボレン、α−クルクメン、β−クルクメン、ジンギベレン、β−セスキフェランドレン、α−ターメロン、β−ターメロン、ＡＲ−ターメロン、β−アトラントン、キサントリゾールが挙げられる。それらを豊富に含有する精油としてターメリックオイル、クミンシードオイル、ショウガオイル、ハルウコンオイル、ガジュツオイル、クスリウコンオイル、ムラサキガジュツオイル、オオウコンオイル、マンゴーガジュツオイル、マンゴージンジャーオイル、ポンツクショウガオイル、オオヤマショウガオイル、ニガショウガオイル、ナンキョウオイル、リョウキョウオイル、バンウコンオイルが挙げられる。
メンタン型ケトンは、イソプレン二分子が縮合した単環式モノテルペンの一部である。メンタンは六員環のパラ位にメチル基とイソプロピル基を有する分子であり、メンタン型ケトンはメンタン骨格を分子構造の一部に持ち、さらにケトン基を少なくとも１個持つ化合物群である。例として、カルボン、ジヒドロカルボン、ツヨノン、α−ツヨン、β−ツヨン、カンファ―、ピペリトン、ピペリテノン、プレゴンが挙げられる。それらを豊富に含有する精油としてペパーミントオイル、スペアミントオイル、ペニーロイヤルミントオイル、ウォーターミントオイル、コーンミントオイル、アジアンミントオイル、オーストラリアミントオイル、ニホンハッカオイル、ベルガモットミントオイル、マルバハッカオイル、ジンジャーミントオイル、セージオイル、ユーカリディベスオイルが挙げられる。
この中でも、カッシャオイル、クローブオイル、ターメリックオイル、クミンシードオイル、スペアミントオイル、ディルシードオイル、ダバナオイル、タラゴンオイル、タイムオイル、バジルオイル、フェンネルオイル、スターアニスオイル、セージオイルが好ましく、カッシャオイル、クローブオイル、スペアミントオイル、ディルシードオイル、タイムオイル、バジルオイル、フェンネルオイル、スターアニスオイル、セージオイルが特に好ましい。
<Essential oil>
In the present invention, the lignans compound is used after being dissolved in an essential oil.
The essential oil is preferably at least one of phenylpropanoid, bisabolan-type sesquiterpene ketone, and menthan-type ketone.
Phenylpropanoids are compounds in which a plurality of 1-phenylpropanes originating from phenylalanine are condensed or derivatives thereof. Examples include lignan compounds such as coumaric acid, cinnamic acid, caffeic acid, eugenol, anethole, estragole, timol, apiole, sinapyl alcohol, ferulic acid and sesamine. Examples of essential oils rich in them include cashier oil, clove leaf oil, clove bad oil, anis oil, fennel oil, taragon oil, thyme oil, parsley seed oil, basil oil, toushikimi (star anis) oil, and sesame oil.
The visabolan-type sesquiterpene ketone is a part of a monocyclic sesquiterpene in which three isoprene molecules are condensed. Monocyclic sesquiterpenes are classified into visabolan type, germanium type, eleman type, and humran type according to the shape of the ring and the position of the functional group. , Has a 6-dimethylhexyl group. Among the bisabolan-type sesquiterpenes, the compound having a carbonyl group is the bisabolan-type sesquiterpene ketone. For example, α-bisaborene, β-bisaborene, γ-bisaborene, α-curcumen, β-curcmen, zingiberene, β-sesquipherandrene, α-turmeron, β-termeron, AR-termeron, β-atlanton, xantry Zol can be mentioned. As essential oils rich in them, turmeric oil, cumin seed oil, ginger oil, ginger oil, gajutsu oil, kusuriukon oil, purple gajutsu oil, oyster oil, mango gajutsu oil, mango ginger oil, pontsuku ginger oil, oyama ginger Examples include oil, ginger oil, nankyo oil, ryokyo oil, and bankoukon oil.
Mentan-type ketones are part of monoterpene monoterpenes in which two isoprene molecules are condensed. Mentan is a molecule having a methyl group and an isopropyl group at the para position of a six-membered ring, and a mentan-type ketone is a group of compounds having a mentan skeleton as a part of its molecular structure and further having at least one ketone group. Examples include carvone, dihydrocarboxylic, thujone, α-thujone, β-thujone, camphor, piperitone, piperitonen and pregon. Peppermint oil, spare mint oil, pennyroyal mint oil, water mint oil, corn mint oil, Asian mint oil, Australian mint oil, Japanese mint oil, bergamot mint oil, malva mint oil, ginger mint oil as essential oils rich in them , Sage oil, eucalyptus oil.
Of these, cashier oil, clove oil, turmeric oil, cumin seed oil, spare mint oil, dill seed oil, davana oil, taragon oil, thyme oil, basil oil, fennel oil, staranis oil, and sage oil are preferable, and cashier oil and clove oil are preferable. , Spare mint oil, dill seed oil, thyme oil, basil oil, fennel oil, star anis oil, sage oil are particularly preferable.
本発明の組成物において用いることができるカッシャオイル、クローブオイル、ターメリックオイル、クミンシードオイル、スペアミントオイル、ディルシードオイル、ダバナオイル、タラゴンオイル、タイムオイル、バジルオイル、フェンネルオイル、スターアニスオイル、セージオイルは、その由来や形態、製造方法等によって、何ら制限されるものではない。
例えば、カッシャオイルはＣｉｎｎａｍｏｍｕｍ ｃａｓｓｉａの樹皮や葉を水蒸気蒸留して得られるが、同種の植物の異なる部位やニッケイ属の近種の植物から得られるオイルも含まれる。
クローブオイルはＳｙｚｙｇｉｕｍ ａｒｏｍａｔｉｃｕｍの葉や蕾を水蒸気蒸留して得られるが、同種の植物の異なる部位やフトモモ属の近種の植物から得られるオイルも含まれる。
ターメリックオイルはＣｕｒｃｕｍａ ｌｏｎｇａの地下茎を水蒸気蒸留して得られるが、同種の植物の異なる部位やショウガ科やウコン属の近種の植物から得られるオイルも含まれる。
クミンシードオイルはＣｕｍｉｎｕｍ ｃｙｍｉｎｕｍの種を水蒸気蒸留して得られるが、同種の植物の異なる部位やクミン属の近種の植物から得られるオイルも含まれる。
スペアミントオイルはＭｅｎｔｈａ ｓｐｉｃａｔａの葉を水蒸気蒸留して得られるが、同種の植物の異なる部位から得られるオイルも含まれる。
ディルシードオイルはＡｎｅｔｈｕｍ ｇｒａｖｅｏｌｅｎｓの種子を水蒸気蒸留して得られるが、同種の植物の異なる部位から得られるオイルも含まれる。
ダバナオイルはＡｒｔｅｍｉｓｉａ ｐａｌｌｅｎｓの植物全体を水蒸気蒸留して得られるが、同種の植物の異なる部位から得られるオイルも含まれる。
タラゴンオイルはＡｒｔｅｍｉｓｉａ ｄｒａｃｕｎｃｕｌｕｓの葉を水蒸気蒸留して得られるが、同種の植物の異なる部位から得られるオイルも含まれる。
タイムオイルは、Ｔｈｙｍｕｓの植物全体を水蒸気蒸留して得られるが、同種の植物の異なる部位から得られるオイルも含まれる。
バジルオイルは、Ｏｃｉｍｕｍ ｂａｓｉｌｉｃｕｍの植物全体を水蒸気蒸留して得られるが、同種の植物の異なる部位から得られるオイルも含まれる。
フェンネルオイルはＦｏｅｎｉｃｕｌｕｍ ｖｕｌｇａｒｅの種子を水蒸気蒸留して得られるが、同種の植物の異なる部位から得られるオイルも含まれる。
スターアニスオイルはＩｌｌｉｃｉｕｍ ｖｅｒｕｍの果実を水蒸気蒸留して得られるが、同種の植物の異なる部位から得られるオイルも含まれる。
セージオイルはＳａｌｖｉａ ｏｆｆｉｃｉｎａｌｉｓ Ｌｉｎｎａｅｕｓの植物全体を水蒸気蒸留して得られるが、同種の植物の異なる部位から得られるオイルも含まれる。
精油は一般的に植物の葉や茎、根、果実、種子、花を水蒸気蒸留して得られる親油性の組成物だが、本発明の組成物において用いるオイルは圧搾や抽出法を用いて得てもよい。 また、抽出物を乾燥精製してアブソリュートにし、それを再び油に溶解してもよい。精油の産地は例としてインド産、インドネシア産、中華人民共和国産、フランス産、スペイン産が挙げられるが、他の国が産地であるものを用いてもよい。さらに、上記精油に含まれているフェニルプロパノイド、ビサボラン型セスキテルペンケトンおよびはメンタン型ケトンの内の少なくともいずれかを抽出精製したもの、又は合成した化合物を配合する合成精油を用いてもよい。
The cashier oil, clove oil, turmeric oil, cumin seed oil, spare mint oil, dill seed oil, davana oil, taragon oil, thyme oil, basil oil, fennel oil, star anis oil, and sage oil that can be used in the compositions of the present invention are: , The origin, form, manufacturing method, etc. are not limited.
For example, cassia oil is obtained by steam distillation of the bark and leaves of Cinnamomum cassia, but also includes oils obtained from different parts of the same species of plants and nearby plants of the genus Cinnamomum.
Clove oil is obtained by steam distillation of the leaves and buds of Syzygium aromaticum, but also includes oils obtained from different parts of the same plant and similar plants of the genus Syzygium.
Turmeric oil is obtained by steam distillation of the underground stems of Curcuma longa, but also includes oils obtained from different parts of the same species of plants and from nearby plants of the family Zingiberaceae and the genus Turmeric.
Cumin seed oil is obtained by steam distillation of Cumin cyminum seeds, but also includes oils obtained from different parts of plants of the same species and plants of close species of the genus Cumin.
Spearmint oil is obtained by steam distillation of Mentha spicata leaves, but also includes oils obtained from different parts of the same plant.
Dill seed oil is obtained by steam distilling the seeds of Anethum grapeolens, but also includes oils obtained from different parts of the same plant.
Davana oil is obtained by steam distillation of the entire Artemisia pallens plant, but also includes oils obtained from different parts of the same plant.
Tarragon oil is obtained by steam distillation of the leaves of Artemisia dracunculus, but also includes oils obtained from different parts of the same plant.
Thymus oils are obtained by steam distillation of the entire Thymus plant, but also include oils obtained from different parts of the same plant.
Basil oil is obtained by steam distillation of the entire Basil plant, but also includes oils obtained from different parts of the same plant.
Fennels oil is obtained by steam distillation of Fennels vulgare seeds, but also includes oils obtained from different parts of the same plant.
Star anise oil is obtained by steam-distilling the fruits of Illicium verum, but also includes oils obtained from different parts of the same plant.
Sage oil is obtained by steam distillation of the entire Salvia officinalis Linnaeus plant, but also includes oils obtained from different parts of the same plant.
Essential oils are generally lipophilic compositions obtained by steam distillation of plant leaves, stems, roots, fruits, seeds and flowers, but the oils used in the compositions of the present invention are obtained by squeezing or extracting. May be good. Alternatively, the extract may be dried and purified to absolute and then dissolved in oil again. Examples of essential oil producing areas include India, Indonesia, People's Republic of China, France, and Spain, but those produced in other countries may be used. Further, a phenylpropanoid, a bisabolan-type sesquiterpene ketone and at least one of the menthan-type ketones contained in the essential oil may be extracted and purified, or a synthetic essential oil containing a synthesized compound may be used.
本発明の組成物はリグナン類化合物を精油に溶解して含有する組成物であり、リグナン類化合物は、セサミンを含有し、好ましくはセサモリンを含有する。
本発明の組成物は、組成物中に、セサミンを２〜３５質量％、好ましくは２〜２５質量％、より好ましくは３〜２０質量％含有する。従来は、セサミンを溶解して含有する組成物を透明に保てるセサミン濃度は当該組成物中１〜２．５質量％程度であったが、リグナン類化合物を溶解させる溶媒として精油を選択することで、組成物中のセサミン濃度を高めることができる。溶媒としての精油は、好ましくはカッシャオイル、クローブオイル、ターメリックオイル、クミンシードオイル、スペアミントオイル、ディルシードオイル、ダバナオイル、タラゴンオイル、タイムオイル、バジルオイル、フェンネルオイル、スターアニスオイル、セージオイルであり、特に好ましくはカッシャオイル、クローブオイル、スペアミントオイル、ディルシードオイル、タイムオイル、バジルオイル、フェンネルオイル、スターアニスオイル、セージオイルである。
セサモリンは、精油中におけるセサミンの溶解性を高める働き、すなわち溶解助剤としての機能も有する。
本発明の組成物は、組成物中に、セサモリンを好ましくは０．１〜３０質量％、より好ましくは２〜２５質量％、特に好ましくは３〜２０質量％含有する。
特に、セサミンを溶解する能力が他の精油より低いターメリックオイル、クミンシードオイルを溶媒として選択する場合、またはセサミンを溶解する能力が高いスペアミントオイル、スターアニスオイル、セージオイル、クローブオイル、カッシャオイル、ディルシードオイル、ダバナオイル、タラゴンオイル、タイムオイル、バジルオイル、フェンネルオイルを溶媒として選択する場合においても、本発明の組成物におけるセサミンとセサモリンの質量比を好ましくは１：０．５〜１．５、より好ましくは１：０．５〜１．３とすることで、ターメリックオイル、クミンシードオイル、スペアミントオイル、スターアニスオイル、セージオイル中のセサミンの溶解性を高めることができる。
The composition of the present invention is a composition containing a lignan compound dissolved in an essential oil, and the lignan compound contains sesamin, preferably sesamolin.
The composition of the present invention contains sesamin in an amount of 2 to 35% by mass, preferably 2 to 25% by mass, and more preferably 3 to 20% by mass. Conventionally, the concentration of sesamin that can dissolve and keep the composition containing sesamin transparent is about 1 to 2.5% by mass in the composition, but by selecting an essential oil as a solvent for dissolving lignan compounds, , The concentration of sesamin in the composition can be increased. Essential oils as solvents are preferably cashier oil, clove oil, turmeric oil, cumin seed oil, spare mint oil, dill seed oil, davana oil, taragon oil, thyme oil, basil oil, fennel oil, staranis oil, sage oil. Particularly preferred are cashier oil, clove oil, sparemint oil, dillseed oil, thyme oil, basil oil, fennel oil, staranis oil and sage oil.
Sesamin also has a function of increasing the solubility of sesamin in essential oils, that is, a function as a solubilizing agent.
The composition of the present invention contains sesamolin in the composition, preferably 0.1 to 30% by mass, more preferably 2 to 25% by mass, and particularly preferably 3 to 20% by mass.
Especially when turmeric oil, cumin seed oil, which has a lower ability to dissolve sesamine than other essential oils, is selected as a solvent, or sparemint oil, staranis oil, sage oil, clove oil, cashier oil, and di, which have a high ability to dissolve sesamine. Even when lucido oil, davana oil, taragon oil, thyme oil, basil oil, and fennel oil are selected as the solvent, the mass ratio of sesamine to sesamolin in the composition of the present invention is preferably 1: 0.5 to 1.5. More preferably, it is set to 1: 0.5 to 1.3, so that the solubility of sesamine in turmeric oil, cumin seed oil, spare mint oil, star anis oil, and sage oil can be enhanced.
また、本発明の組成物はセサミン濃度を高めることができるだけでなく、精油を選択することで刺激と苦味が少なく摂取しやすい組成物とすることができる。溶媒としての精油は、好ましくはターメリックオイル、ディルシードオイル、ダバナオイル、タラゴンオイル、バジルオイル、フェンネルオイル、スターアニスオイル、セージオイル及び精油ブレンドであり、特に好ましくは、フェンネルオイル、スターアニスオイル及び精油ブレンドである。 In addition, the composition of the present invention can not only increase the concentration of sesamin, but also can be made into a composition that is easy to ingest with less irritation and bitterness by selecting an essential oil. The essential oil as a solvent is preferably a turmeric oil, dillseed oil, davana oil, taragon oil, basil oil, fennel oil, staranis oil, sage oil and essential oil blend, and particularly preferably fennel oil, staranis oil and essential oil. It is a blend.
また、本発明の組成物は、リグナン類化合物を中鎖脂肪酸（ＭＣＴ）に溶解して含有する。リグナン類化合物、特にセサミンの含有量が高いものは、セサモリンを含有することにより、ＭＣＴの溶解性を高めることができる。
ＭＣＴ中におけるセサミンとセサモリンの質量比を、１：０．５〜１．５、好ましくは１：０．５〜１．２、より好ましくは１：０．７〜１．０することができる。
In addition, the composition of the present invention contains a lignan compound dissolved in a medium chain fatty acid (MCT). Lignan compounds, particularly those having a high content of sesamin, can enhance the solubility of MCT by containing sesamolin.
The mass ratio of sesamin to sesamolin in the MCT can be 1: 0.5 to 1.5, preferably 1: 0.5 to 1.2, more preferably 1: 0.7 to 1.0.
＜組成物の調製方法＞
例えば、ゴマ抽出物を精油に混合し、好ましくは７５〜１００℃、５〜１５分、より好ましくは８５℃、１０分間で加熱しながら溶解させる。その後、溶液を水で室温まで冷却し、一晩静置した後、静置後のサンプルについて１５℃、１００００ｒｐｍで５分間遠心分離し、得られた上清により本発明の組成物を得ることができる。
この組成物に含まれるセサミン、セサモリン濃度（質量％）は、液体クロマトグラフ質量分析法（ＬＣ−ＭＳ）により定量することができる。
<Preparation method of composition>
For example, the sesame extract is mixed with the essential oil and dissolved while heating at preferably 75-100 ° C. for 5-15 minutes, more preferably 85 ° C. for 10 minutes. Then, the solution is cooled to room temperature with water, allowed to stand overnight, and then the sample after standing is centrifuged at 15 ° C. and 10000 rpm for 5 minutes, and the obtained supernatant can be used to obtain the composition of the present invention. can.
The concentration of sesamin and sesamolin (% by mass) contained in this composition can be quantified by liquid chromatography-mass spectrometry (LC-MS).
本発明の組成物は、飲食品（機能性食品、健康補助食品、栄養機能食品、特別用途食品、特定保健用食品、栄養補助食品、食事療法用食品、健康食品、サプリメント等）の他に、医薬品、医薬部外品、化粧品等の形態で提供することが好適である。本発明の組成物を飲食品として提供する場合、その形態は、錠剤、カプセル剤、粉末剤、顆粒剤、ドリンク剤（溶液剤及び懸濁液剤が含まれる）等の健康食品の形態で提供することも、清涼飲料、茶飲料、ヨーグルトや乳酸菌飲料等の乳製品、調味料、加工食品、デザート類、菓子（例えば、ガム、キャンディ、ゼリー）等の形態で提供することも可能であるが、これらに限定されない。 In addition to foods and drinks (functional foods, health supplements, nutritionally functional foods, special purpose foods, specified health foods, dietary supplements, dietary foods, health foods, supplements, etc.), the composition of the present invention can be used in addition to foods and drinks. It is preferable to provide it in the form of pharmaceuticals, non-pharmaceutical products, cosmetics and the like. When the composition of the present invention is provided as a food or drink, it is provided in the form of a health food such as a tablet, a capsule, a powder, a granule, or a drink (including a solution and a suspension). It can also be provided in the form of soft drinks, tea drinks, dairy products such as yogurt and lactic acid bacteria drinks, seasonings, processed foods, desserts, confectionery (for example, gum, candy, jelly), etc. Not limited to these.
本発明の組成物は、その効果を損なわない限り、任意の所望成分を配合してもよい。例えば、ビタミンＤ、ビタミンＥなどのビタミン類、ＤＨＡ、ＥＰＡ等の油脂類、ミネラル類、ホルモン、栄養成分、香料などの生理活性成分のほか、製剤化において配合される防腐剤、安定化剤、抗酸化剤等を適宜配合することができる。 The composition of the present invention may contain any desired component as long as its effect is not impaired. For example, vitamins such as vitamin D and vitamin E, fats and oils such as DHA and EPA, minerals, hormones, nutritional components, physiologically active components such as fragrances, as well as preservatives and stabilizers blended in formulation. Antioxidants and the like can be appropriately added.
＜透明性評価＞
本発明の組成物を用いると、リグナン類化合物（特にゴマ抽出物）を高濃度で溶解し、かつ透明な溶液を作成することができる。透明性の評価は全光線透過法、曇り度（ヘイズ）法、透視時計を用いる透視度法等、または濁度より透過度を評価する手法を用いてもよい。本発明の組成物はセサミン濃度を高く保ったうえで上記の手法で測定した透明性が既存のセサミン濃度が低いカプセル内容液と同程度であるという特徴がある。また、リグナン類化合物を含む組成物を透明被膜のソフトカプセルに充填する場合、内容液が透明であれば外見が美しくなり、消費者への訴求が向上するという利点があるため、本発明において透明性は重要な要素である。
<Transparency evaluation>
By using the composition of the present invention, lignan compounds (particularly sesame extract) can be dissolved at a high concentration to prepare a transparent solution. The transparency may be evaluated by using the total light transmittance method, the haze method, the transparency method using a fluoroscopic clock, or a method of evaluating the transparency based on the turbidity. The composition of the present invention is characterized in that the transparency measured by the above method after maintaining a high sesamin concentration is comparable to that of the existing capsule content liquid having a low sesamin concentration. Further, when a composition containing a lignan compound is filled in a soft capsule having a transparent film, if the content liquid is transparent, there is an advantage that the appearance becomes beautiful and the appeal to consumers is improved. Therefore, the transparency in the present invention is obtained. Is an important factor.
＜生物学的利用率＞
本発明の組成物を用いると、粉末のリグナン類化合物（特にゴマ抽出物）を経口摂取する場合と比較して、リグナン類化合物（特にゴマ抽出物）の生物学的利用率を向上させることができる。結果としてリグナン類化合物の生物学的利用率が向上し、それらの血中濃度及び脳内濃度が向上する。本発明の組成物における溶媒としての精油は、好ましくはカッシャオイル、クローブオイル、ターメリックオイル、クミンシードオイル、スペアミントオイル、ディルシードオイル、タイムオイル、ダバナオイル、タラゴンオイル、バジルオイル、フェンネルオイル、スターアニスオイル、セージオイルであり、特に好ましくはターメリックオイルである。
<Bioavailability>
The composition of the present invention can be used to improve the bioavailability of lignan compounds (particularly sesame extract) as compared to oral ingestion of powdered lignan compounds (particularly sesame extract). can. As a result, the bioavailability of lignan compounds is improved, and their blood and brain concentrations are improved. The essential oil as a solvent in the composition of the present invention is preferably cashier oil, clove oil, turmeric oil, cumin seed oil, spare mint oil, dill seed oil, thyme oil, davana oil, taragon oil, basil oil, fennel oil, star anis oil. , Sage oil, particularly preferably turmeric oil.
以下、実施例に沿ってさらに説明するが、本発明は実施例に限定されるものではない。 Hereinafter, the present invention will be further described with reference to Examples, but the present invention is not limited to the Examples.
（溶解性試験） (Solubility test)
１．実験材料の調製
ゴマ抽出物は稲畑香料株式会社製の原料を使用した。セサミン・セサモリン濃度は表１の通りである。
1. 1. Preparation of experimental materials For the sesame extract, raw materials manufactured by Inahata Fragrance Co., Ltd. were used. Table 1 shows the concentrations of sesamin and sesamolin.
クローブオイルは、稲畑香料株式会社より、Ｅｕｇｅｎｉａ ｃａｒｙｏｐｈｙｌｌａｔａ Ｔｈｕｎｂｅｒｇの葉の水蒸気蒸留品を購入し、実験に用いた。
ターメリックオイルは、稲畑香料株式会社より、Ｃ．ｌｏｎｇａの地下茎の水蒸気蒸留品を購入し、実験に用いた。
カッシャオイルは、稲畑香料株式会社よりＣｉｎｎａｍｏｍｕｍ ｃａｓｓｉａの葉の水蒸気蒸留品を購入し、実験に用いた。
クミンシードオイルは稲畑香料株式会社よりＣｕｍｉｎｕｍ ｃｙｍｉｎｕｍの種子の水蒸気蒸留品を購入し、実験に用いた。
スペアミントオイルは、稲畑香料株式会社よりＭｅｎｔｈａ ｓｐｉｃａｔａの葉の水蒸気蒸留品を購入し、実験に用いた。
ディルシードオイルは、稲畑香料株式会社よりＡｎｅｔｈｕｍ ｇｒａｖｅｏｌｅｎｓの種子の水蒸気蒸留品を購入し、実験に用いた。
ダバナオイルは、稲畑香料株式会社よりＡｒｔｅｍｉｓｉａ ｐａｌｌｅｎｓの植物全体の水蒸気蒸留品を購入し、実験に用いた。
タラゴンオイルは、稲畑香料株式会社よりＡｒｔｅｍｉｓｉａ ｄｒａｃｕｎｃｕｌｕｓの葉の水蒸気蒸留品を購入し、実験に用いた。
タイムオイルは、稲畑香料株式会社よりＴｈｙｍｕｓの植物全体の水蒸気蒸留品を購入し、実験に用いた。
バジルオイルは、稲畑香料株式会社よりＯｃｉｍｕｍ ｂａｓｉｌｉｃｕｍの植物全体の水蒸気蒸留品を購入し、実験に用いた。
フェンネルオイルは、稲畑香料株式会社よりＦｏｅｎｉｃｕｌｕｍ ｖｕｌｇａｒｅの種子の水蒸気蒸留品を購入し、実験に用いた。
スターアニスオイルは、稲畑香料株式会社よりＩｌｌｉｃｉｕｍ ｖｅｒｕｍの果実の水蒸気蒸留品を購入し、実験に用いた。
セージオイルは、稲畑香料株式会社よりＳａｌｖｉａ ｏｆｆｉｃｉｎａｌｉｓ Ｌｉｎｎａｅｕｓの葉の水蒸気蒸留品を購入し、実験に用いた。
ＭＣＴは英和トレーディング社（日本、東京）よりＥｌａｅｉｓ ｇｕｉｎｅｅｎｓｉｓの果実圧搾品を購入し、実験に用いた。
米胚芽油は築野ライフサイエンス株式会社より「米胚芽油」を購入し、使用した。
ゴマ油は竹本油脂株式会社より「太白胡麻油」を購入し、使用した。
For clove oil, a steam-distilled product of Eugenia caryophyllata Thumberg leaves was purchased from Inahata Fragrance Co., Ltd. and used in the experiment.
Turmeric oil is available from Inahata Fragrance Co., Ltd. A steam-distilled product of longa's rhizome was purchased and used in the experiment.
For cashier oil, a steam-distilled product of Cinnamomum cassia leaves was purchased from Inahata Fragrance Co., Ltd. and used in the experiment.
For cumin seed oil, a steam-distilled product of cumin cyminum seeds was purchased from Inahata Fragrance Co., Ltd. and used in the experiment.
For spearmint oil, a steam-distilled product of Mentha spicata leaves was purchased from Inahata Fragrance Co., Ltd. and used in the experiment.
For dill seed oil, a steam-distilled product of Anetum grapeolens seeds was purchased from Inahata Fragrance Co., Ltd. and used in the experiment.
For Davana oil, a steam-distilled product of the whole plant of Artemisia pallens was purchased from Inahata Fragrance Co., Ltd. and used in the experiment.
For tarragon oil, a steam-distilled product of Artemisia dracunculus leaves was purchased from Inahata Fragrance Co., Ltd. and used in the experiment.
For thymus oil, a steam-distilled product of the whole plant of Thymus was purchased from Inahata Fragrance Co., Ltd. and used in the experiment.
For basil oil, a steam-distilled product of the whole plant of Basil Basilium was purchased from Inahata Fragrance Co., Ltd. and used in the experiment.
For fennel oil, a steam-distilled product of Fennels vulgare seeds was purchased from Inahata Fragrance Co., Ltd. and used in the experiment.
Star anise oil purchased a steam-distilled product of Illicium verum fruit from Inahata Fragrance Co., Ltd. and used it in the experiment.
For sage oil, a steam-distilled product of Salvia officinalis Linnaeus leaves was purchased from Inahata Fragrance Co., Ltd. and used in the experiment.
MCT purchased a fruit-squeezed product of Elaeis guineaensis from Eiwa Trading Co., Ltd. (Tokyo, Japan) and used it in the experiment.
For rice germ oil, "rice germ oil" was purchased from Tsukino Life Science Co., Ltd. and used.
For sesame oil, we purchased "Taishaku sesame oil" from Takemoto Oil & Fats Co., Ltd. and used it.
２．溶解性試験の評価方法
遠心後上清のセサミンの溶解性の評価は以下に定める４段階（◎、〇、△、×）で行った。
◎（溶解性が大変高い）： セサミン濃度が１０質量％以上
〇（溶解性が高い）： セサミン濃度が３質量％以上１０質量％未満
△（溶解性は中程度である）： セサミン濃度が１質量％以上３質量％未満
×（溶解性が低い）： セサミン濃度が１質量％未満
2. Evaluation method of solubility test The solubility of sesamin in the supernatant after centrifugation was evaluated in the following four steps (⊚, 〇, Δ, ×).
◎ (Very high solubility): Sesamine concentration is 10% by mass or more 〇 (High solubility): Sesamine concentration is 3% by mass or more and less than 10% by mass △ (Solubility is medium): Sesamine concentration is 1 Mass% or more and less than 3 mass% × (low solubility): Sesamine concentration is less than 1 mass%
（ＬＣ−ＭＳ分析法）
すべてのサンプルはＵＰＬＣ−ＭＳシステム（ＬＣＭＳ−８０５０、株式会社島津製作所）を用いた。セサミン分析は以下の条件で行った。カラムはＳｈｉｍ−ｐａｃｋ ＸＲ−ＯＤＳＩＩ （２．０ｍｍＩ．Ｄ×７５ｍｍ，ｐａｒｔｉｃｌｅ ｓｉｚｅ；２．２μｍ、株式会社島津製作所）を用いた。流速は０．２ｍＬ／分とした。移動相はメタノール：５ｍＭ酢酸アンモニウム水溶液、４：１の混合溶液を用いた。保持時間は２．２５分であった。注入溶液量は１μＬとした。ＥＳＩ−ＭＳ測定は以下の条件で行った。ドリフト電圧は２．５ｋＶとした。イオン化モードはポジティブモードとした。イオン源温度は１００℃とした。脱溶媒ガス流量は１０Ｌ／分、脱溶媒温度は１００℃とした。衝突誘起解離ガスは２７０ｋＰａのアルゴンガスを用い、衝突エネルギーは１１ｅＶとした。化合物の同定には多重反応モニタリングを用い、［Ｍ＋ＮＨ４］＋＝ｍ／ｚ３７２．２０から［Ｍ＋ＮＨ４−Ｃ７Ｈ５Ｏ２−Ｈ２Ｏ］＋＝ｍ／ｚ３７２．２０への遷移を追跡した。セサモリン分析は、以下に記載する箇所以外は上記のセサミン分析法と同じ手法を用いた。移動相はメタノール：５ ｍＭ酢酸アンモニウム水溶液、４：１から１：０まで２．５分で線形的に濃度を変化させ、その後２．５１分で４：１まで戻した。保持時間は２．５５分であった。ＥＳＩの導入はＭＳ／ＭＳを用いた。ドリフト電圧は４．０ｋＶとした。イオン源温度は２２５℃、脱溶媒温度は１５０℃とした。アルゴンガスの衝突エネルギーは２７ｅＶとした。化合物の同定には多重反応モニタリングを用い、［Ｍ＋ＮＨ４］＋＝ｍ／ｚ３８８．２０から［Ｍ−Ｃ１２Ｈ１２Ｏ５＋Ｈ］＋＝ｍ／ｚ１３５．００への遷移を追跡した。
(LC-MS analysis method)
All samples used the UPLC-MS system (LCMS-8050, Shimadzu Corporation). Sesamin analysis was performed under the following conditions. A Sim-pack XR-ODSII (2.0 mm ID × 75 mm, particle size; 2.2 μm, Shimadzu Corporation) was used as the column. The flow velocity was 0.2 mL / min. As the mobile phase, a mixed solution of methanol: 5 mM ammonium acetate aqueous solution and 4: 1 was used. The retention time was 2.25 minutes. The amount of the injection solution was 1 μL. The ESI-MS measurement was performed under the following conditions. The drift voltage was 2.5 kV. The ionization mode was set to positive mode. The ion source temperature was 100 ° C. The desolventized gas flow rate was 10 L / min, and the desolvated temperature was 100 ° C. Argon gas of 270 kPa was used as the collision-induced dissociation gas, and the collision energy was 11 eV. With multiple reaction monitoring in identifying compounds, [M + NH 4] + = from m / z372.20 [M + NH 4 -C 7 H 5 O 2 -H 2 O] + = Track transition to m / z372.20 bottom. For the sesamin analysis, the same method as the above sesamin analysis method was used except for the parts described below. The mobile phase was linearly changed in concentration from 4: 1 to 1: 0 in 2.5 minutes with methanol: 5 mM ammonium acetate aqueous solution, and then returned to 4: 1 in 2.51 minutes. The retention time was 2.55 minutes. MS / MS was used for the introduction of ESI. The drift voltage was 4.0 kV. The ion source temperature was 225 ° C. and the solvent removal temperature was 150 ° C. The collision energy of argon gas was 27 eV. Multiple reaction monitoring was used to identify the compounds, and the transition from [M + NH 4 ] + = m / z 388.20 to [MC 12 H 12 O 5 + H] + = m / z 135.00 was followed.
（例１）
表２に示す組成比で、表１に示すゴマ抽出物Ａ〜Ｃのいずれかを精油（クローブオイル）に混合し、８５℃で１０分間加熱しながら溶解させた。なお、配合時の配合組成物に含まれるセサミン、セサモリンの組成（理論値）を表１に基づき算出し、表２に示した。
その後、溶液を水で室温まで冷却し、一晩静置した。静置中に沈殿が生じたサンプルが存在したため、溶液を１５℃、１００００ｒｐｍで５分間、多目的遠心機ＣＡＸ−３７１（株式会社トミー精工）を用いて遠心分離し、上清に含まれるセサミン、セサモリン濃度（質量％）をＵＰＬＣ−ＭＳシステム（ＬＣＭＳ−８０５０、株式会社島津製作所）により定量した。その結果を表３に示す。
(Example 1)
Any of the sesame extracts A to C shown in Table 1 was mixed with the essential oil (clove oil) at the composition ratio shown in Table 2 and dissolved while heating at 85 ° C. for 10 minutes. The compositions (theoretical values) of sesamin and sesamolin contained in the compounding composition at the time of compounding were calculated based on Table 1 and are shown in Table 2.
The solution was then cooled to room temperature with water and allowed to stand overnight. Since there was a sample in which precipitation occurred during standing, the solution was centrifuged at 15 ° C. and 10000 rpm for 5 minutes using a multipurpose centrifuge CAX-371 (Tomy Seiko Co., Ltd.), and sesamine and sesamolin contained in the supernatant. The concentration (% by mass) was quantified by the UPLC-MS system (LCMS-8050, Shimadzu Corporation). The results are shown in Table 3.
溶媒としてクローブオイルを使用した場合セサミンの溶解度を高めることができ、最大１９．０質量％まで上清組成物にセサミンを溶解させることができた。 When clove oil was used as the solvent, the solubility of sesamin could be increased, and sesamin could be dissolved in the supernatant composition up to 19.0% by mass.
（例２）
表４に示す組成比でゴマ抽出物と精油（カッシャオイル）を混合するほかは、上記例１と同様の処理を行った。配合時の配合組成物に含まれるセサミン、セサモリンの組成（理論値）を表４に、上清組成物に含まれるセサミン、セサモリン濃度（ＬＣ−ＭＳによる測定結果）を表５に示す。
(Example 2)
The same treatment as in Example 1 above was carried out except that the sesame extract and the essential oil (cassia oil) were mixed at the composition ratios shown in Table 4. Table 4 shows the composition (theoretical value) of sesamin and sesamolin contained in the compounding composition at the time of compounding, and Table 5 shows the concentration of sesamin and sesamolin (measurement result by LC-MS) contained in the supernatant composition.
溶媒としてカッシャオイルを使用した場合セサミンの溶解度を高めることができ、最大１９．４質量％まで上清組成物にセサミンを溶解させることができた。 When cashier oil was used as the solvent, the solubility of sesamin could be increased, and sesamin could be dissolved in the supernatant composition up to 19.4% by mass.
（例３）
表６に示す組成比で、ゴマ抽出物Ａ、Ｂ、Ｄを精油（スペアミントオイルＡ）に混合するほかは、上記例１と同様の処理を行った。本実験におけるスペアミントオイルＡは、カルボンが６０％、ｄ−リモネンが２０％含有しているものを用いた。なお、配合時の配合組成物に含まれるセサミン、セサモリンの組成（理論値）を表１に基づき算出した。配合時の配合組成物に含まれるセサミン、セサモリンの組成（理論値）を表６に、上清に含まれるセサミン、セサモリン濃度（ＬＣによる測定結果）を表７に示す。
(Example 3)
The same treatment as in Example 1 above was carried out except that the sesame extracts A, B and D were mixed with the essential oil (spearmint oil A) at the composition ratios shown in Table 6. As the spearmint oil A in this experiment, one containing 60% of carvone and 20% of d-limonene was used. The composition (theoretical value) of sesamin and sesamolin contained in the compounding composition at the time of compounding was calculated based on Table 1. Table 6 shows the composition (theoretical value) of sesamin and sesamolin contained in the compounding composition at the time of compounding, and Table 7 shows the concentration of sesamin and sesamolin contained in the supernatant (measurement result by LC).
溶媒としてスペアミントオイルＡを使用した場合セサミンの溶解度を高めることができ、最大１７．４質量％まで上清組成物にセサミンを溶解させることができた。 When spearmint oil A was used as the solvent, the solubility of sesamin could be increased, and sesamin could be dissolved in the supernatant composition up to 17.4% by mass.
（例４）
表８に示す組成比で、ゴマ抽出物Ｄを精油（スペアミントオイルＢ）に混合するほかは、上記例１と同様の処理を行った。本実験におけるスペアミントオイルＢは、カルボンが８０％、ｄ−リモネンが１０％含有しているものを用いた。なお、配合時の配合組成物に含まれるセサミン、セサモリンの組成（理論値）を表１に基づき算出した。配合時の配合組成物に含まれるセサミン、セサモリンの組成（理論値）を表８に、上清に含まれるセサミン、セサモリン濃度（ＬＣによる測定結果）を表９に示す。
(Example 4)
The same treatment as in Example 1 was carried out except that the sesame extract D was mixed with the essential oil (spearmint oil B) at the composition ratios shown in Table 8. As the spearmint oil B in this experiment, one containing 80% of carvone and 10% of d-limonene was used. The composition (theoretical value) of sesamin and sesamolin contained in the compounding composition at the time of compounding was calculated based on Table 1. Table 8 shows the composition (theoretical value) of sesamin and sesamolin contained in the compounding composition at the time of compounding, and Table 9 shows the concentration of sesamin and sesamolin contained in the supernatant (measurement result by LC).
溶媒としてスペアミントオイルＢを使用した場合セサミンの溶解度を高めることができ、最大１７．４質量％まで上清組成物にセサミンを溶解させることができた。 When spearmint oil B was used as the solvent, the solubility of sesamin could be increased, and sesamin could be dissolved in the supernatant composition up to 17.4% by mass.
（例５）
表１０に示す組成比で、ゴマ抽出物Ｄを精油（ディルシードオイル）に混合するほかは、上記例１と同様の処理を行った。なお、配合時の配合組成物に含まれるセサミン、セサモリンの組成（理論値）を表１に基づき算出した。配合時の配合組成物に含まれるセサミン、セサモリンの組成（理論値）を表１０に、上清に含まれるセサミン、セサモリン濃度（ＬＣによる測定結果）を表１１に示す。
(Example 5)
The same treatment as in Example 1 was carried out except that the sesame extract D was mixed with the essential oil (dirseed oil) at the composition ratio shown in Table 10. The composition (theoretical value) of sesamin and sesamolin contained in the compounding composition at the time of compounding was calculated based on Table 1. Table 10 shows the composition (theoretical value) of sesamin and sesamolin contained in the compounding composition at the time of compounding, and Table 11 shows the concentration of sesamin and sesamolin contained in the supernatant (measurement result by LC).
溶媒としてディルシードオイルを使用した場合セサミンの溶解度を高めることができ、最大１５．３質量％まで上清組成物にセサミンを溶解させることができた。 When dillseed oil was used as the solvent, the solubility of sesamin could be increased, and sesamin could be dissolved in the supernatant composition up to 15.3% by mass.
（例６）
表１２に示す組成比で、ゴマ抽出物Ｄを精油（ダバナオイル）に混合するほかは、上記例１と同様の処理を行った。なお、配合時の配合組成物に含まれるセサミン、セサモリンの組成（理論値）を表１に基づき算出した。配合時の配合組成物に含まれるセサミン、セサモリンの組成（理論値）を表１２に、上清に含まれるセサミン、セサモリン濃度（ＬＣによる測定結果）を表１３に示す。
(Example 6)
The same treatment as in Example 1 was carried out except that the sesame extract D was mixed with the essential oil (davana oil) at the composition ratio shown in Table 12. The composition (theoretical value) of sesamin and sesamolin contained in the compounding composition at the time of compounding was calculated based on Table 1. The composition (theoretical value) of sesamin and sesamolin contained in the compounding composition at the time of compounding is shown in Table 12, and the concentration of sesamin and sesamolin contained in the supernatant (measurement result by LC) is shown in Table 13.
溶媒としてダバナオイルを使用した場合セサミンの溶解度を高めることができ、最大１１．９質量％まで上清組成物にセサミンを溶解させることができた。 When dabana oil was used as the solvent, the solubility of sesamin could be increased, and sesamin could be dissolved in the supernatant composition up to 11.9% by mass.
（例７）
表１４に示す組成比で、ゴマ抽出物Ｄを精油（タラゴンオイル）に混合するほかは、上記例１と同様の処理を行った。なお、配合時の配合組成物に含まれるセサミン、セサモリンの組成（理論値）を表１に基づき算出した。配合時の配合組成物に含まれるセサミン、セサモリンの組成（理論値）を表１４に、上清に含まれるセサミン、セサモリン濃度（ＬＣによる測定結果）を表１５に示す。
(Example 7)
The same treatment as in Example 1 was carried out except that the sesame extract D was mixed with the essential oil (tarragon oil) at the composition ratio shown in Table 14. The composition (theoretical value) of sesamin and sesamolin contained in the compounding composition at the time of compounding was calculated based on Table 1. Table 14 shows the composition (theoretical value) of sesamin and sesamolin contained in the compounding composition at the time of compounding, and Table 15 shows the concentration of sesamin and sesamolin contained in the supernatant (measurement result by LC).
溶媒としてタラゴンオイルを使用した場合セサミンの溶解度を高めることができ、最大１５．１質量％まで上清組成物にセサミンを溶解させることができた。 When tarragon oil was used as the solvent, the solubility of sesamin could be increased, and sesamin could be dissolved in the supernatant composition up to 15.1% by mass.
（例８）
表１６に示す組成比で、ゴマ抽出物Ｄを精油（タイムオイル）に混合するほかは、上記例１と同様の処理を行った。なお、配合時の配合組成物に含まれるセサミン、セサモリンの組成（理論値）を表１に基づき算出した。配合時の配合組成物に含まれるセサミン、セサモリンの組成（理論値）を表１６に、上清に含まれるセサミン、セサモリン濃度（ＬＣによる測定結果）を表１７に示す。
(Example 8)
The same treatment as in Example 1 was carried out except that the sesame extract D was mixed with the essential oil (thyme oil) at the composition ratio shown in Table 16. The composition (theoretical value) of sesamin and sesamolin contained in the compounding composition at the time of compounding was calculated based on Table 1. Table 16 shows the composition (theoretical value) of sesamin and sesamolin contained in the compounding composition at the time of compounding, and Table 17 shows the concentration of sesamin and sesamolin contained in the supernatant (measurement result by LC).
溶媒としてタイムオイルを使用した場合セサミンの溶解度を高めることができ、最大１７．８質量％まで上清組成物にセサミンを溶解させることができた。 When thyme oil was used as the solvent, the solubility of sesamin could be increased, and sesamin could be dissolved in the supernatant composition up to 17.8% by mass.
（例９）
表１８に示す組成比で、ゴマ抽出物Ｄを精油（バジルオイル）に混合するほかは、上記例１と同様の処理を行った。なお、配合時の配合組成物に含まれるセサミン、セサモリンの組成（理論値）を表１に基づき算出した。配合時の配合組成物に含まれるセサミン、セサモリンの組成（理論値）を表１８に、上清に含まれるセサミン、セサモリン濃度（ＬＣによる測定結果）を表１９に示す。
(Example 9)
The same treatment as in Example 1 was carried out except that the sesame extract D was mixed with the essential oil (basil oil) at the composition ratios shown in Table 18. The composition (theoretical value) of sesamin and sesamolin contained in the compounding composition at the time of compounding was calculated based on Table 1. Table 18 shows the composition (theoretical value) of sesamin and sesamolin contained in the compounding composition at the time of compounding, and Table 19 shows the concentration of sesamin and sesamolin contained in the supernatant (measurement result by LC).
溶媒としてバジルオイルを使用した場合セサミンの溶解度を高めることができ、最大１５．１質量％まで上清組成物にセサミンを溶解させることができた。 When basil oil was used as the solvent, the solubility of sesamin could be increased, and sesamin could be dissolved in the supernatant composition up to 15.1% by mass.
（例１０）
表２０に示す組成比で、ゴマ抽出物Ｄを精油（フェンネルオイル）に混合するほかは、上記例１と同様の処理を行った。なお、配合時の配合組成物に含まれるセサミン、セサモリンの組成（理論値）を表１に基づき算出した。配合時の配合組成物に含まれるセサミン、セサモリンの組成（理論値）を表２０に、上清に含まれるセサミン、セサモリン濃度（ＬＣによる測定結果）を表２１に示す。
(Example 10)
The same treatment as in Example 1 was carried out except that the sesame extract D was mixed with the essential oil (fennel oil) at the composition ratio shown in Table 20. The composition (theoretical value) of sesamin and sesamolin contained in the compounding composition at the time of compounding was calculated based on Table 1. Table 20 shows the composition (theoretical value) of sesamin and sesamolin contained in the compounding composition at the time of compounding, and Table 21 shows the concentration of sesamin and sesamolin contained in the supernatant (measurement result by LC).
溶媒としてフェンネルオイルを使用した場合セサミンの溶解度を高めることができ、最大１７．５質量％まで上清組成物にセサミンを溶解させることができた。 When fennel oil was used as the solvent, the solubility of sesamin could be increased, and sesamin could be dissolved in the supernatant composition up to 17.5% by mass.
（例１１）
表２２に示す組成比で、ゴマ抽出物Ａ、Ｂ、Ｄを精油（スターアニスオイル）に混合するほかは、上記例１と同様の処理を行った。なお、配合時の配合組成物に含まれるセサミン、セサモリンの組成（理論値）を表１に基づき算出した。配合時の配合組成物に含まれるセサミン、セサモリンの組成（理論値）を表２２に、上清に含まれるセサミン、セサモリン濃度（ＬＣによる測定結果）を表２３に示す。
(Example 11)
The same treatment as in Example 1 was carried out except that the sesame extracts A, B and D were mixed with the essential oil (star anise oil) at the composition ratios shown in Table 22. The composition (theoretical value) of sesamin and sesamolin contained in the compounding composition at the time of compounding was calculated based on Table 1. Table 22 shows the composition (theoretical value) of sesamin and sesamolin contained in the compounding composition at the time of compounding, and Table 23 shows the concentration of sesamin and sesamolin contained in the supernatant (measurement result by LC).
溶媒としてスターアニスオイルを使用した場合セサミンの溶解度を高めることができ、最大１７．４質量％まで上清組成物にセサミンを溶解させることができた。 When star anise oil was used as the solvent, the solubility of sesamin could be increased, and sesamin could be dissolved in the supernatant composition up to 17.4% by mass.
（例１２）
表２４に示す組成比で、ゴマ抽出物Ａ、Ｂ、Ｄを精油（セージオイル）に混合するほかは、上記例１と同様の処理を行った。なお、配合時の配合組成物に含まれるセサミン、セサモリンの組成（理論値）を表１に基づき算出した。配合時の配合組成物に含まれるセサミン、セサモリンの組成（理論値）を表２４に、上清に含まれるセサミン、セサモリン濃度（ＬＣによる測定結果）を表２５に示す。
(Example 12)
The same treatment as in Example 1 was carried out except that the sesame extracts A, B and D were mixed with the essential oil (sage oil) at the composition ratios shown in Table 24. The composition (theoretical value) of sesamin and sesamolin contained in the compounding composition at the time of compounding was calculated based on Table 1. Table 24 shows the composition (theoretical value) of sesamin and sesamolin contained in the compounding composition at the time of compounding, and Table 25 shows the concentration of sesamin and sesamolin contained in the supernatant (measurement result by LC).
溶媒としてセージオイルを使用した場合セサミンの溶解度を高めることができ、最大１３．０質量％まで上清組成物にセサミンを溶解させることができた。 When sage oil was used as the solvent, the solubility of sesamin could be increased, and sesamin could be dissolved in the supernatant composition up to 13.0% by mass.
精油のブレンド
クローブオイル、ターメリックオイル、カッシャオイル、クミンシードオイルに加えて、スペアミントオイル、ディルシードオイル、ダバナオイル、タラゴンオイル、タイムオイル、バジルオイル、フェンネルオイル、スターアニスオイル、セージオイルを用いることで、新たに嗜好性の高い精油ブレンドを作成し、かつセサミンを高濃度に溶解することでできた。精油ブレンドは以下の２種類を作成した。
By using a blend of essential oils, clove oil, turmeric oil, cashier oil, cumin seed oil, spare mint oil, dill seed oil, davana oil, taragon oil, thyme oil, basil oil, fennel oil, star anis oil, and sage oil. It was made by creating a new highly palatable essential oil blend and dissolving sesamine in a high concentration. The following two types of essential oil blends were prepared.
（例１３）
表２６に示す組成比で、ゴマ抽出物Bを精油ブレンドに混合するほかは、上記例１と同様の処理を行った。なお、配合時の配合組成物に含まれるセサミン、セサモリンの組成（理論値）を表１に基づき算出した。配合時の配合組成物に含まれるセサミン、セサモリンの組成（理論値）を表２６に、上清に含まれるセサミン、セサモリン濃度（ＬＣによる測定結果）を表２７に示す。
(Example 13)
The same treatment as in Example 1 was carried out except that the sesame extract B was mixed with the essential oil blend at the composition ratios shown in Table 26. The composition (theoretical value) of sesamin and sesamolin contained in the compounding composition at the time of compounding was calculated based on Table 1. Table 26 shows the composition (theoretical value) of sesamin and sesamolin contained in the compounding composition at the time of compounding, and Table 27 shows the concentration of sesamin and sesamolin contained in the supernatant (measurement result by LC).
溶媒として精油ブレンドを使用した場合セサミンの溶解度を高めることができ、最大１０．３質量％まで上清組成物にセサミンを溶解させることができた。また、精油をブレンドすることで嗜好性の高い組成物を作成することができた。
When the essential oil blend was used as the solvent, the solubility of sesamin could be increased, and sesamin could be dissolved in the supernatant composition up to 10.3% by mass. In addition, by blending the essential oils, a highly palatable composition could be prepared.
（例１４）
表２８に示す組成比でゴマ抽出物と精油（ターメリックオイル）を混合するほかは、上記例１と同様の処理を行った。配合時の配合組成物に含まれるセサミン、セサモリンの組成（理論値）を表２８に、上清に含まれるセサミン、セサモリン濃度（ＬＣによる測定結果）を表２９に示す。
(Example 14)
The same treatment as in Example 1 above was carried out except that the sesame extract and the essential oil (turmeric oil) were mixed at the composition ratios shown in Table 28. The composition (theoretical value) of sesamin and sesamolin contained in the compounding composition at the time of compounding is shown in Table 28, and the concentration of sesamin and sesamolin contained in the supernatant (measurement result by LC) is shown in Table 29.
溶媒としてターメリックオイルを使用した場合セサミンの溶解度を高めることができ、最大７．５質量％までカプセル内容液組成物にセサミンを溶解させることができた。 When turmeric oil was used as the solvent, the solubility of sesamin could be increased, and sesamin could be dissolved in the capsule content liquid composition up to 7.5% by mass.
（例１５）
表３０に示す組成比でゴマ抽出物と精油（クミンシードオイル）を混合するほかは、上記例１と同様の処理を行った。配合時の配合組成物に含まれるセサミン、セサモリンの組成（理論値）を表３０に、上清に含まれるセサミン、セサモリン濃度（ＬＣによる測定結果）を表３１に示す。
(Example 15)
The same treatment as in Example 1 was carried out except that the sesame extract and the essential oil (cumin seed oil) were mixed at the composition ratios shown in Table 30. Table 30 shows the composition (theoretical value) of sesamin and sesamolin contained in the compounding composition at the time of compounding, and Table 31 shows the concentration of sesamin and sesamolin contained in the supernatant (measurement result by LC).
遠心後上清中のセサミン：セサモリンを濃度比１：０．７〜１で配合することで、セサミンを溶解する能力が低いクミンシードオイルを用いても、セサミンを９．６質量％溶解して含有するカプセル内溶液組成物を調製することができた。
By blending sesamin: sesamolin in the supernatant after centrifugation at a concentration ratio of 1: 0.7 to 1, even if sesamin seed oil, which has a low ability to dissolve sesamin, is used, sesamin is dissolved in 9.6% by mass and contained. It was possible to prepare an in-capsule solution composition to be prepared.
（例１６）
表３２に示す組成比でゴマ抽出物とＭＣＴを混合するほかは上記例１と同様の処理を行った。
配合時の配合組成物に含まれるセサミン、セサモリンの組成（理論値）を表３２に、上清に含まれるセサミン、セサモリン濃度（ＬＣによる測定結果）を表３３に示す。
(Example 16)
The same treatment as in Example 1 was carried out except that the sesame extract and MCT were mixed at the composition ratios shown in Table 32.
The composition (theoretical value) of sesamin and sesamolin contained in the compounding composition at the time of compounding is shown in Table 32, and the concentration of sesamin and sesamolin contained in the supernatant (measurement result by LC) is shown in Table 33.
配合組成物中に、セサミンの含有量が高いゴマ抽出物製品ＡやＢでは、ＭＣＴはセサミンをカプセル内容液組成物中に２質量％以上の濃度で溶解することができなかった。一方、遠心後上清中のセサミン：セサモリンの濃度比を約１：１とすることで、セサミンを溶解する能力が低い油脂のＭＣＴを用いても、セサミンを４．４質量％まで溶解して含有するカプセル内容液組成物を調製することができた。 In the sesame extract products A and B having a high content of sesamin in the compounding composition, MCT could not dissolve sesamin in the capsule content liquid composition at a concentration of 2% by mass or more. On the other hand, by setting the concentration ratio of sesamin: sesamolin in the supernatant after centrifugation to about 1: 1, even if MCT of fats and oils having a low ability to dissolve sesamin is used, sesamin can be dissolved up to 4.4% by mass. The capsule content liquid composition to be contained could be prepared.
（例１７）
表３４に示す組成比で、ゴマ抽出物Ｃと米胚芽油を混合するほかは上記例１と同様の処理を行った。
配合時の配合組成物に含まれるセサミン、セサモリンの組成（理論値）を表３４に、上清に含まれるセサミン、セサモリン濃度を表３５に示す。
(Example 17)
The same treatment as in Example 1 was carried out except that the sesame extract C and the rice germ oil were mixed at the composition ratios shown in Table 34.
The composition (theoretical value) of sesamin and sesamolin contained in the compounding composition at the time of compounding is shown in Table 34, and the concentration of sesamin and sesamolin contained in the supernatant is shown in Table 35.
配合組成物中に、セサモリンの含有量がセサミン含有量を上回るゴマ抽出物製品Ｃを用いても、米胚芽油はセサミンをカプセル内容液組成物中に０．０８質量％以上の濃度で溶解することができなかった。 Even if sesame extract product C having a sesamin content exceeding the sesamin content is used in the compounding composition, the rice germ oil dissolves sesamin in the capsule content liquid composition at a concentration of 0.08% by mass or more. I couldn't.
（例１８）
表３６に示す組成比でゴマ抽出物Ｃとゴマ油を混合するほかは上記例１と同様の処理を行った。
配合時の配合組成物に含まれるセサミン、セサモリンの組成（理論値）を表３６に、上清に含まれるセサミン、セサモリン濃度を表３７に示す。
(Example 18)
The same treatment as in Example 1 was carried out except that the sesame extract C and sesame oil were mixed at the composition ratios shown in Table 36.
The composition (theoretical value) of sesamin and sesamolin contained in the compounding composition at the time of compounding is shown in Table 36, and the concentration of sesamin and sesamolin contained in the supernatant is shown in Table 37.
配合組成物中に、セサモリンの含有量がセサミン含有量を上回るゴマ抽出物製品Ｃを用いても、米胚芽油はセサミンをカプセル内容液組成物中に０．２質量％以上の濃度で溶解することができなかった。
Even if sesame extract product C having a sesamin content exceeding the sesamin content is used in the compounding composition, the rice germ oil dissolves sesamin in the capsule content liquid composition at a concentration of 0.2% by mass or more. I couldn't.
（例１９）
（透明性評価試験）
(Example 19)
(Transparency evaluation test)
１．透明性評価試験の評価方法
溶解性試験で調製したソフトカプセル内容液組成物Ｃ−３、Ｃ−６、Ｃ−９、Ｃ−１２、Ｃ−１５、Ｃ−１８、Ｃ−２１、Ｃ−２３、Ｃ−２８、Ｃ−３１、Ｃ−３３、Ｃ−３５、Ｃ−３６、Ｃ−４１、Ｃ−４３、Ｃ−４６、Ｃ−４８、Ｃ−５１、Ｃ−５３、Ｃ−５６、Ｃ−５８、Ｃ−６１、Ｃ−６３、Ｃ−６６、Ｃ−７１、Ｃ−７２、Ｃ−７６、、Ｃ−８６、Ｃ−８７、Ｃ−８８、Ｃ−８９、Ｃ−９１、Ｃ−９２、Ｃ−９３、Ｃ−９４、Ｃ−９５、Ｃ−９６、Ｃ−９７、Ｃ−９８、Ｃ―９９、Ｃ−１００、Ｃ−１０１、Ｃ−１０２を紫外・可視分光光度計（ＨＩＴＡＣＨＩ Ｕ−３９００ Ｓｐｅｃｔｒｏｐｈｏｔｏｍｅｔｅｒ）を用いた紫外・可視吸光度測定を行い、上記バイアル瓶中の溶液及び溶媒の透明度を定量した。濁度は７５０ｎｍの透過度を用いて評価した。ベースラインは、ガラスセルの透過度とした。
これらのソフトカプセル内容液組成物の透明性評価は以下に定める４段階（◎、〇、△、×）で行った。
◎（透明性が大変高い）： ７５０ｎｍ透過度が９５％以上
〇（透明性が高い）： ７５０ｎｍ透過度が８０％以上
△（透明性が中程度である）： ７５０ｎｍ透過度が６０％以上８０％未満
×（透明性が低い）： ７５０ｎｍ透過度が６０％未満
1. 1. Evaluation method of transparency evaluation test Soft capsule content solution composition prepared in the solubility test C-3, C-6, C-9, C-12, C-15, C-18, C-21, C-23, C-28, C-31, C-33, C-35, C-36, C-41, C-43, C-46, C-48, C-51, C-53, C-56, C- 58, C-61, C-63, C-66, C-71, C-72, C-76 ,, C-86, C-87, C-88, C-89, C-91, C-92 , C-93, C-94, C-95, C-96, C-97, C-98, C-99, C-100, C-101, C-102. Ultraviolet / visible absorbance was measured using a (-3900 Spectrophotometer), and the transparency of the solution and solvent in the vial was quantified. Turbidity was evaluated using a transmittance of 750 nm. The baseline was the transparency of the glass cell.
The transparency evaluation of these soft capsule content liquid compositions was carried out in four stages (⊚, 〇, Δ, ×) specified below.
◎ (Very high transparency): 750 nm transmittance 95% or more 〇 (High transparency): 750
溶解性試験で調製したソフトカプセル内容液組成物Ｃ−３、Ｃ−６、Ｃ−９、Ｃ−１２、Ｃ−１５、Ｃ−１８、Ｃ−２１、Ｃ−２３、Ｃ−２８、Ｃ−３１、Ｃ−３３、Ｃ−３５、Ｃ−３６、Ｃ−４１、Ｃ−４３、Ｃ−４６、Ｃ−４８、Ｃ−５１、Ｃ−５３、Ｃ−５６、Ｃ−５８、Ｃ−６１、Ｃ−６３、Ｃ−６６、Ｃ−７１、Ｃ−７２、Ｃ−７６、Ｃ−８６、Ｃ−８７、Ｃ−８８、Ｃ−８９、Ｃ−９１、Ｃ−９２、Ｃ−９３、Ｃ−９４、Ｃ−９５、Ｃ−９６、Ｃ−９７、Ｃ−９８、Ｃ―９９、Ｃ−１００、Ｃ−１０１、Ｃ−１０２の透明性試験の結果を表３８に示す。 Soft capsule content liquid composition prepared in the solubility test C-3, C-6, C-9, C-12, C-15, C-18, C-21, C-23, C-28, C-31 , C-33, C-35, C-36, C-41, C-43, C-46, C-48, C-51, C-53, C-56, C-58, C-61, C -63, C-66, C-71, C-72, C-76, C-86, C-87, C-88, C-89, C-91, C-92, C-93, C-94 , C-95, C-96, C-97, C-98, C-99, C-100, C-101, C-102, and the results of the transparency test are shown in Table 38.
次に対照品として、セサミンを溶解させているタイプのソフトカプセル（サントリー株式会社、セサミンＥＸ）の内容液（対照例１）とセサミンを溶解させているタイプのソフトカプセル（小林製薬株式会社、小林製薬のセサミン）の内容液（対照例２）を用い、これら内容液の７５０ｎｍの可視光の透過度を測定し、上記と同様の基準で透明性評価を行った。結果を表３９に示す。 Next, as a control product, a content solution (control example 1) of a soft capsule in which sesamin is dissolved (Suntory Co., Ltd., Sesamin EX) and a soft capsule in which sesamin is dissolved (Kobayashi Pharmaceutical Co., Ltd., Kobayashi Pharmaceutical Co., Ltd.) Using the contents of sesamin (Control Example 2), the transmission of visible light at 750 nm of these contents was measured, and the transparency was evaluated according to the same criteria as described above. The results are shown in Table 39.
本発明に係るカプセル内容液組成物Ｃ−３、Ｃ−６、Ｃ−９、Ｃ−１２、Ｃ−１５、Ｃ−１８、Ｃ−２１、Ｃ−２３、Ｃ−２８、Ｃ−３１、Ｃ−３３、Ｃ−３５、Ｃ−３６、Ｃ−４１、Ｃ−４３、Ｃ−４６、Ｃ−４８、Ｃ−５１、Ｃ−５３、Ｃ−５６、Ｃ−５８、Ｃ−６１、Ｃ−６３、Ｃ−６６、Ｃ−７１、Ｃ−７２、Ｃ−７６、Ｃ−８６、Ｃ−８７、Ｃ−８８、Ｃ−８９、Ｃ−９１、Ｃ−９２、Ｃ−９３、Ｃ−９４、Ｃ−９５、Ｃ−９６、Ｃ−９７、Ｃ−９８、Ｃ―９９、Ｃ−１００、Ｃ−１０１、Ｃ−１０２は、サントリーのセサミンＥＸや小林製薬のセサミンよりも高濃度にカプセル内溶液中にセサミンを溶解させ、かつこれら対照品と同程度の透明性を示した。 Capsule content liquid composition according to the present invention C-3, C-6, C-9, C-12, C-15, C-18, C-21, C-23, C-28, C-31, C -33, C-35, C-36, C-41, C-43, C-46, C-48, C-51, C-53, C-56, C-58, C-61, C-63 , C-66, C-71, C-72, C-76, C-86, C-87, C-88, C-89, C-91, C-92, C-93, C-94, C -95, C-96, C-97, C-98, C-99, C-100, C-101, C-102 are contained in the capsule solution at a higher concentration than Suntory's Sesamine EX and Kobayashi Pharmaceutical's Sesamine. Sesamine was dissolved in the mixture, and the transparency was comparable to that of these control products.
セサミンを、乳化剤とミツロウを用いて基材油に乳化懸濁させているタイプのソフトカプセル（株式会社オーガランドの「セサミンカプセル」）の内容液の７５０ｎｍの可視光の透過度は測定不能であった。
The transmittance of visible light at 750 nm of the content of a soft capsule (“Sesamine Capsule” by Organland Co., Ltd.) in which sesamine was emulsified and suspended in base oil using an emulsifier and beeswax was unmeasurable. ..
官能試験
ターメリックオイル、カッシャオイルに加えて、スペアミントオイル、ディルシードオイル、ダバナオイル、タラゴンオイル、タイムオイル、バジルオイル、フェンネルオイル、スターアニスオイル、セージオイル、精油ブレンドにゴマ抽出物を溶解し、官能試験を行った。官能試験はゴマ抽出物配合精油を１滴口に含み、溶液の味を評価した。
評価基準
刺激性なし（２点）・苦味なし（１点）：計３点
刺激性なし（２点）・苦味あり（０点）：計２点
刺激性あり（０点）・苦味なし（１点）：計１点
刺激性あり（０点）・苦味あり（０点）：計０点
官能試験の評価基準は、ゴマ抽出物配合精油として好ましくない味覚である刺激性と苦味を指標とした。刺激性とは、組成物を口に含んだ際に辛み又は痛みを感じ、咽るような感覚を受けることを差す。苦味とは、アルカロイド化合物を口に含んだ際のような不快な味を差す。組成物が刺激性を持つ場合、口に含むと痛みを感じ咽てしまうことから、抵抗性があり可食性が低い。一方、組成物が苦味を持つ場合、口に含むと不快な味がするものの、抵抗性はなく可食性は低くない。以上より、苦味がないことよりも刺激性がないことの方が食品としての価値が高く、その価値の差を反映するために刺激性なしを２点、苦味なしを１点とする傾斜配点とした。
被験者は十分訓練された１２人で行い、上記基準に基づいて評価を行った。１２人の評価の平均点が０．３点未満の場合は×、０．３点以上１点未満の場合は△、１点以上２点未満の場合は〇、２点以上２．５点未満の場合は〇〇、２．５点以上の場合は〇〇〇とした。結果は以下の表４０の通りである。
カッシャオイル、タイムオイルの評価と比較してターメリックオイル、ディルシードオイル、ダバナオイル、タラゴンオイル、バジルオイル、フェンネルオイル、スターアニスオイル、セージオイル及び精油ブレンドは評価が高く、食品として優れた味を持つことが分かった。特に、フェンネルオイル、スターアニスオイル、精油ブレンドが望ましい。
Sensory test In addition to turmeric oil and cashier oil, sesame extract is dissolved in spearmint oil, dillseed oil, davana oil, taragon oil, thyme oil, basil oil, fennel oil, staranis oil, sage oil and essential oil blend, and sensory. The test was performed. In the sensory test, one drop of essential oil containing sesame extract was contained in the mouth, and the taste of the solution was evaluated.
Evaluation Criteria No irritation (2 points) / No bitterness (1 point): 3 points in total No irritation (2 points) / Bitterness (0 points): 2 points in total No irritation (0 points) / No bitterness (1 point) Points): 1 point in total Irritation (0 points), bitterness (0 points): 0 points in total
The evaluation criteria for the sensory test were the irritation and bitterness, which are unfavorable tastes for the essential oil containing sesame extract. Irritation refers to the feeling of pain or pain when the composition is in the mouth and the sensation of throating. Bitter taste refers to an unpleasant taste such as when an alkaloid compound is contained in the mouth. When the composition is irritating, it is resistant and less edible because it causes pain and throat when contained in the mouth. On the other hand, when the composition has a bitter taste, it tastes unpleasant when it is contained in the mouth, but it is not resistant and edible. From the above, the value as a food is higher when it is not irritating than when it is not bitter, and in order to reflect the difference in value, there are 2 points for non-irritant and 1 point for no bitterness. bottom.
Twelve well-trained subjects were used for evaluation based on the above criteria. If the average score of the evaluation of 12 people is less than 0.3 points, it is ×, if it is 0.3 points or more and less than 1 point, it is △, if it is 1 point or more and less than 2 points, it is 〇, and it is 2 points or more and less than 2.5 points. In the case of, it was evaluated as 〇〇, and in the case of 2.5 points or more, it was evaluated as 〇〇〇. The results are shown in Table 40 below.
Turmeric oil, dillseed oil, davana oil, taragon oil, basil oil, fennel oil, staranis oil, sage oil and essential oil blends are highly rated and have excellent food taste compared to cashier oil and thyme oil ratings. It turned out. In particular, fennel oil, star anise oil, and essential oil blends are desirable.
（例２０）
（生物学的利用率評価法）
（概要）
実験は、ゴマ抽出物Ｃとターメリックオイルを１：９の割合で溶解させたセサミ・ターメリックオイル、又はゴマ抽出物Ｃを経口投与し、血清及び脳内のセサミン及びセサモリン濃度を測定することにより行った。
(Example 20)
(Bioavailability evaluation method)
(Overview)
The experiment was carried out by orally administering sesame turmeric oil in which sesame extract C and turmeric oil were dissolved at a ratio of 1: 9, or sesame extract C, and measuring the concentrations of sesamin and sesamolin in serum and brain. rice field.
（マウス血液、脳サンプル調製法）
マウスは４週齢のＳｌｃ：ｄｄＹ種をＳＬＣ社（静岡、日本）より購入した。飼育は２５±１℃の室温で、１２時間の明暗サイクルの元、餌（ＭＦ、オリエンタルイースト社、東京、日本）と水道水は自由に摂取できる環境で行った１週間の飼育で順化させたのち、実験に用いた。
ゴマ抽出物、ターメリックオイル、及びセサミ・ターメリックオイルはカルボキシメチルセルロース２％水溶液に溶解させた。セサミ・ターメリックオイルにおけるゴマ抽出物Ｃとターメリックオイルの割合は１：９とした。ゴマ抽出物が２．５ｍｇ／ｋｇ、ターメリックオイルが２２．５ｍｇ／ｋｇ、又はセサミ・ターメリックオイル２５ｍｇ／ｋｇをマウスに経口投与した。マウスの血液と脳を投与３０分後に回収した。血液サンプルは、麻酔下で下大静脈から得た。その後、脳を採取する前にマウスの左心室から等張性塩化ナトリウム水溶液を灌流した。採取された血液は３０００ｇで１０分間遠心分離し、その上清として血清を得た。
(Mouse blood, brain sample preparation method)
As for the mice, a 4-week-old Slc: ddY species was purchased from SLC (Shizuoka, Japan). Breeding was carried out at room temperature of 25 ± 1 ° C, under a 12-hour light-dark cycle, and food (MF, Oriental East, Tokyo, Japan) and tap water were acclimated by breeding for one week in an environment where they could freely ingest. Later, it was used in the experiment.
Sesame extract, turmeric oil, and sesame turmeric oil were dissolved in a 2% aqueous solution of carboxymethyl cellulose. The ratio of sesame extract C to turmeric oil in sesame turmeric oil was 1: 9. Mice were orally administered 2.5 mg / kg of sesame extract, 22.5 mg / kg of turmeric oil, or 25 mg / kg of sesame turmeric oil. Mouse blood and brain were collected 30 minutes after administration. Blood samples were taken from the inferior vena cava under anesthesia. Then, an isotonic sodium chloride aqueous solution was perfused from the left ventricle of the mouse before collecting the brain. The collected blood was centrifuged at 3000 g for 10 minutes, and serum was obtained as the supernatant.
（分析サンプル調製法）
血清サンプル（１００μＬ）とアセトニトリル（５００μＬ）を混合し、３分間振盪することで抽出した。その後、溶液を１０４０ｇ、３分間遠心分離した。上清の溶媒を真空除去し、残渣を５０μＬのアセトニトリルに溶解させることで、ＬＣ−ＭＳサンプルとした。脳サンプル（３０ｍｇ）を粉砕し、アセトニトリル１５０μＬで抽出した。１０分間振盪と超音波照射を行い、上清を１０４０ｇ、３分間遠心分離した。上清の溶媒を真空除去し、残渣を７５μＬのアセトニトリルに溶解させることで、ＬＣ−ＭＳサンプルとした。
(Analytical sample preparation method)
Serum sample (100 μL) and acetonitrile (500 μL) were mixed and extracted by shaking for 3 minutes. Then, 1040 g of the solution was centrifuged for 3 minutes. The solvent of the supernatant was removed by vacuum, and the residue was dissolved in 50 μL of acetonitrile to prepare an LC-MS sample. A brain sample (30 mg) was ground and extracted with 150 μL of acetonitrile. Shaking and ultrasonic irradiation were performed for 10 minutes, and the supernatant was centrifuged at 1040 g for 3 minutes. The solvent of the supernatant was removed by vacuum, and the residue was dissolved in 75 μL of acetonitrile to prepare an LC-MS sample.
（分析法）
すべてのサンプルはＵＰＬＣ−ＭＳシステム（ＬＣＭＳ−８０５０、株式会社島津製作所）を用いた。詳細な測定条件は上述の溶解性試験の「ＬＣ−ＭＳ分析法」で記載した手法と同様に行った。
(Analysis method)
All samples used the UPLC-MS system (LCMS-8050, Shimadzu Corporation). The detailed measurement conditions were the same as those described in the "LC-MS analysis method" of the solubility test described above.
図１は左から順にマウスに対照飼料、ゴマ抽出物配合飼料、セサミ・ターメリックオイル配合飼料を与えた場合のセサミンの血中濃度である。ゴマ抽出物配合飼料を与えた場合のセサミン血中濃度は１ｎｇ／ｍＬであったのに対し、セサミ・ターメリックオイル配合飼料を与えた場合のセサミン血中濃度は９ｎｇ／ｍＬであり、約９倍に向上した。 FIG. 1 shows the blood concentration of sesamin when the control feed, the sesame extract mixed feed, and the sesame / turmeric oil mixed feed were fed to the mice in order from the left. The blood concentration of sesamin was 1 ng / mL when the sesame extract-containing feed was given, whereas the sesamin blood concentration when the sesame / turmeric oil-containing feed was given was 9 ng / mL, which was about 9 times higher. Improved to.
図２は左から順にマウスに対照飼料、ゴマ抽出物配合飼料、セサミ・ターメリックオイル配合飼料を与えた場合のセサミンの脳内濃度である。ゴマ抽出物配合飼料を与えた場合のセサミン脳内濃度は１ｎｇ／ｇ以下であったのに対し、セサミ・ターメリックオイル配合飼料を与えた場合のセサミン血中濃度は９ｎｇ／ｇであり、９倍以上に向上した。 FIG. 2 shows the intracerebral concentration of sesamin when the control feed, the sesame extract mixed feed, and the sesame / turmeric oil mixed feed were given to the mice in order from the left. The concentration of sesamin in the brain when the sesame extract-containing feed was given was 1 ng / g or less, whereas the sesamin blood concentration when the sesame / turmeric oil-containing feed was given was 9 ng / g, which was 9 times higher. It has improved above.
図３は左から順にマウスに対照飼料、ゴマ抽出物配合飼料、セサミ・ターメリックオイル配合飼料を与えた場合のセサモリンの血中濃度である。ゴマ抽出物配合飼料を与えた場合のセサモリン血中濃度は２ｎｇ／ｍＬであったのに対し、セサミ・ターメリックオイル配合飼料を与えた場合のセサモリン血中濃度は２６ｎｇ／ｍＬであり、約１３倍に向上した。 FIG. 3 shows the blood concentrations of sesamolin when the control feed, the sesame extract mixed feed, and the sesame / turmeric oil mixed feed were fed to the mice in order from the left. The blood concentration of sesamolin was 2 ng / mL when the sesame extract-containing feed was given, whereas the sesamolin blood concentration when the sesame / turmeric oil-containing feed was given was 26 ng / mL, which was about 13 times higher. Improved to.
図４は左から順にマウスに対照飼料、ゴマ抽出物配合飼料、セサミ・ターメリックオイル配合飼料を与えた場合のセサモリンの脳内濃度である。ゴマ抽出物配合飼料を与えた場合のセサモリン脳内濃度は４ｎｇ／ｇ以下であったのに対し、セサミ・ターメリックオイル配合飼料を与えた場合のセサモリン血中濃度は３６ｎｇ／ｇであり、９倍以上に向上した。 FIG. 4 shows the brain concentration of sesamolin when the control feed, the sesame extract mixed feed, and the sesame / turmeric oil mixed feed were fed to the mice in order from the left. The brain concentration of sesamolin when the sesame extract-containing feed was given was 4 ng / g or less, whereas the sesamolin blood concentration when the sesame / turmeric oil-containing feed was given was 36 ng / g, which was 9 times higher. It has improved above.
上記結果から、セサミン、セサモリンの生物学的利用性は溶媒としてターメリックオイルを用いることにより大きく改善することが示された。 From the above results, it was shown that the bioavailability of sesamin and sesamolin was greatly improved by using turmeric oil as a solvent.
本発明を用いることにより、組成物、特にカプセル内溶液の透明度を維持したまま、組成物１粒あたりの成分摂取量を増加させて、経口摂取する組成物数を減らすことができる。またこれにより、組成物の加工費を削減することができ、生産コストを抑えることができる。さらに本発明の組成物により生物学的利用率を向上させることができる。 By using the present invention, it is possible to increase the amount of component intake per capsule while maintaining the transparency of the composition, particularly the solution in the capsule, and reduce the number of compositions to be orally ingested. Further, as a result, the processing cost of the composition can be reduced, and the production cost can be suppressed. Further, the composition of the present invention can improve the bioavailability.
Claims (16)
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| JP2021126050A (en) * | 2020-02-10 | 2021-09-02 | 株式会社えがお | Composition comprising lignan compound as dissolved in clove oil and method for enhancing sesamin dissolubility |
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| JP7504609B2 (en) | 2020-02-10 | 2024-06-24 | 株式会社えがお | Composition containing lignan compounds dissolved in clove oil, and method for increasing solubility of sesamin |
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