JP2005343865A - Low smelling enzyme-treated hesperidin composition - Google Patents
Low smelling enzyme-treated hesperidin composition Download PDFInfo
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- JP2005343865A JP2005343865A JP2004168631A JP2004168631A JP2005343865A JP 2005343865 A JP2005343865 A JP 2005343865A JP 2004168631 A JP2004168631 A JP 2004168631A JP 2004168631 A JP2004168631 A JP 2004168631A JP 2005343865 A JP2005343865 A JP 2005343865A
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- 239000001100 (2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one Substances 0.000 title claims abstract description 132
- QUQPHWDTPGMPEX-UHFFFAOYSA-N Hesperidine Natural products C1=C(O)C(OC)=CC=C1C1OC2=CC(OC3C(C(O)C(O)C(COC4C(C(O)C(O)C(C)O4)O)O3)O)=CC(O)=C2C(=O)C1 QUQPHWDTPGMPEX-UHFFFAOYSA-N 0.000 title claims abstract description 132
- QUQPHWDTPGMPEX-UTWYECKDSA-N aurantiamarin Natural products COc1ccc(cc1O)[C@H]1CC(=O)c2c(O)cc(O[C@@H]3O[C@H](CO[C@@H]4O[C@@H](C)[C@H](O)[C@@H](O)[C@H]4O)[C@@H](O)[C@H](O)[C@H]3O)cc2O1 QUQPHWDTPGMPEX-UTWYECKDSA-N 0.000 title claims abstract description 132
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- 229940025878 hesperidin Drugs 0.000 title claims abstract description 132
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- QUQPHWDTPGMPEX-QJBIFVCTSA-N hesperidin Chemical compound C1=C(O)C(OC)=CC=C1[C@H]1OC2=CC(O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO[C@H]4[C@@H]([C@H](O)[C@@H](O)[C@H](C)O4)O)O3)O)=CC(O)=C2C(=O)C1 QUQPHWDTPGMPEX-QJBIFVCTSA-N 0.000 title claims abstract description 132
- ARGKVCXINMKCAZ-UHFFFAOYSA-N neohesperidine Natural products C1=C(O)C(OC)=CC=C1C1OC2=CC(OC3C(C(O)C(O)C(CO)O3)OC3C(C(O)C(O)C(C)O3)O)=CC(O)=C2C(=O)C1 ARGKVCXINMKCAZ-UHFFFAOYSA-N 0.000 title claims abstract description 132
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- IMMBLRJLSYJQIZ-UNQGIHKMSA-N (2S)-7-[3,4-dihydroxy-5-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxymethyl]oxan-2-yl]oxy-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydrochromen-4-one Chemical compound COc1ccc(cc1O)[C@@H]1CC(=O)c2c(O)cc(OC3OC(COC4OC(C)C(O)C(O)C4O)C(OC4OC(CO)C(O)C(O)C4O)C(O)C3O)cc2O1 IMMBLRJLSYJQIZ-UNQGIHKMSA-N 0.000 description 2
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- 239000003463 adsorbent Substances 0.000 description 2
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- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 2
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- IKGXIBQEEMLURG-NVPNHPEKSA-N rutin Chemical class O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 IKGXIBQEEMLURG-NVPNHPEKSA-N 0.000 description 2
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 2
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- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 2
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- 229940108690 glucosyl hesperidin Drugs 0.000 description 1
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Landscapes
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Seasonings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
Description
本発明は、酵素処理ヘスペリジン組成物に関し、さらに詳しくは、臭気を低減した低臭気酵素処理ヘスペリジン組成物などのヘスペリジン組成物に関する。 The present invention relates to an enzyme-treated hesperidin composition, and more particularly to a hesperidin composition such as a low-odor enzyme-treated hesperidin composition with reduced odor.
例えば、ヘスペリジン、酵素処理ヘスペリジンは、共に天然色素の退色防止、血行促進、ビタミンＰ様作用を示し、特に酵素処理ヘスペリジンは糖転移ビタミンＰとして飲食物、化粧品等に添加して用いられている（例えば、非特許文献１、２、３）。酵素処理ヘスペリジンは、ヘスペリジンの可溶化、安定化、精製度の向上などを図ったものである。 For example, both hesperidin and enzyme-treated hesperidin exhibit natural pigment fading prevention, blood circulation promotion, and vitamin P-like action. In particular, enzyme-treated hesperidin is used as a glycosylated vitamin P added to foods and drinks, cosmetics and the like ( For example, non-patent documents 1, 2, 3). Enzyme-treated hesperidin is intended to solubilize and stabilize hesperidin and improve the degree of purification.
ヘスペリジンはカンキツ系の果皮等に多く含まれているフラボノイドであり、柑橘類のうちでも特に生産量の多い温州みかんなどを原料とするミカンジュ−スの製造工程で沈殿物として生じる物質である。なお、レモンは、みかんやオレンジに比してその生産量自体も少なく、従ってレモン由来のヘスペリジン含有物は、これまで殆ど上市されていない。 Hesperidin is a flavonoid that is abundantly contained in citrus peels, and is a substance that is produced as a precipitate in the mandarin orange manufacturing process using citrus fruits, such as Unshu mandarin orange, which has a particularly high production amount. In addition, the production amount of lemon itself is smaller than that of oranges or oranges, and therefore, hesperidin-containing products derived from lemon have hardly been marketed so far.
ところで、通常ヘスペリジン含有物（抽出物）は、温州みかん、ダイダイ等の果皮、果汁、または種子より、例えば室温下で、アルカリ性水溶液で抽出される。この温州みかん、ダイダイ由来のヘスペリジン抽出成分に、糖付与体の存在下でシクロデキストリングルカノトランスフェラ−ゼを作用させて得られた酵素処理品は、特有の臭いがあり多孔性合成吸着樹脂、イオン交換樹脂、及びカ−ボン処理を用いても充分に脱臭することは困難である。食品分野では、その強い特有の臭気のために使用量を控えざるを得なく、さらに臭いに敏感な化粧品分野においては使用できないか、または使用量を大きく制限せざるを得なかった。 By the way, a hesperidin-containing substance (extract) is usually extracted with an alkaline aqueous solution at the room temperature, for example, from the skin of persimmons such as Unshu mandarin or Daidai, fruit juice, or seeds. The enzyme-treated product obtained by allowing cyclodextrin glucanotransferase to act on the extract component of Hesperidin derived from Wenzhou mandarin orange and Daidai in the presence of a sugar donor, has a unique odor and is a porous synthetic adsorption resin, It is difficult to sufficiently deodorize using ion exchange resin and carbon treatment. In the food field, due to its strong peculiar odor, it was unavoidable to use it, and in the cosmetics field sensitive to odor, it could not be used, or the amount used had to be greatly restricted.
この酵素処理ヘスペリジンに含まれる特有の臭気は、温州みかん、ダイダイ等の原料に由来する不純物と考えられるが、酵素処理に供される原料のヘスペリジン含有物ではあまり感じられず、酵素処理を行うことによってよりその特異臭が明確になった。このように酵素処理に供される原料のヘスペリジン含有物では、その特異臭があまり感じられない理由は、ヘスペリジン含有物に含まれる多種の香気性成分（臭い成分）の影響で、原料中の特異臭を知覚・確認することは難しいためと考えられる。酵素処理操作で水溶性になった酵素処理ヘスペリジン組成物は、その後水系で分離・精製処理されると原料由来の臭い成分の多くが除去される。しかし、問題となる臭いは酵素処理ヘスペリジン（すなわちα-
グルコシルヘスペリジン）と同様の挙動を示すため、精製処理で完全に分離除去することが難しく、このため酵素処理ヘスペリジン組成物ではより強くその特異臭が感じられるようになると考えられた。
The unique odor contained in this enzyme-treated hesperidin is thought to be an impurity derived from raw materials such as Unshu mandarin orange and Daidai, but it is not felt so much in the hesperidin-containing material used for the enzyme treatment, and the enzyme treatment should be performed. The specific odor became clearer. The reason why the specific odor is not felt so much in the raw material containing hesperidin used for enzyme treatment in this way is the influence of various aromatic components (odorous components) contained in the hesperidin containing material. This is thought to be because it is difficult to perceive and confirm a strange odor. When the enzyme-treated hesperidin composition rendered water-soluble by the enzyme treatment operation is then separated and purified in an aqueous system, most of the odor components derived from the raw materials are removed. However, the problematic odor is enzyme-treated hesperidin (ie α-
Since it exhibits the same behavior as that of glucosyl hesperidin), it is difficult to completely separate and remove it by purification treatment, and it was thought that the specific odor was felt stronger in the enzyme-treated hesperidin composition.
そこで、本発明者らは、上記問題点を解決するべく、ミカン由来のヘスペリジン含有物に代えて、ヘスペリジンを含有するレモンその他の種々の柑橘類についても酵素処理や多孔性合成吸着樹脂などによる処理を行ったところ、同じ柑橘類でもその種類により酵素処理後の特異臭の発現強化の程度は異なること、さらに同じ種類の柑橘類でも収穫時期によって異なることがわかった。さらにヘスペリジン含有物を一定温度で加熱することにより、その後の臭いが著しく低減することを見出した。 Therefore, in order to solve the above-mentioned problems, the present inventors, instead of the mandarin-derived hesperidin-containing material, also processed with lemon or other various citrus fruits containing hesperidin with an enzyme treatment or a porous synthetic adsorption resin. As a result, it was found that the degree of expression enhancement of the specific odor after the enzyme treatment was different depending on the kind of the same citrus fruit, and that the same kind of citrus fruit was different depending on the harvest time. Furthermore, it has been found that the subsequent odor is remarkably reduced by heating the hesperidin-containing material at a constant temperature.
すなわち、温州ミカンより抽出したヘスペリジン含有物には特異臭が多いのに対し、レモンより抽出したヘスペリジン含有物、特に冬場収穫品種、すなわち通常その産地の秋から春に収穫されるレモンの品種から抽出されたヘスペリジン含有物には、特異臭が少ないことがわかった。さらに驚くことに、このヘスペリジン含有物を酵素処理する前に一定温
度で加熱することにより得られた酵素処理ヘスペリジンにはほとんど特異臭のないことなどを見出し、本発明を完成したものである。
In other words, the hesperidin-containing material extracted from Satsuma mandarin has a specific odor, whereas hesperidin-containing material extracted from lemon, especially from winter harvested varieties, that is, lemon varieties usually harvested from autumn to spring The resulting hesperidin-containing product was found to have less specific odor. Surprisingly, the inventors have found that the enzyme-treated hesperidin obtained by heating the hesperidin-containing material at a certain temperature before the enzyme treatment has almost no specific odor, thereby completing the present invention.
これにより、これまでミカン由来のヘスペリジン組成物ではその臭いの影響で使用できなかった商品及び分野、または使用量が制限されていた商品においてもその利用及び使用量を増やすことが可能となった。 As a result, it has become possible to increase the use and use amount of commercial hesperidin compositions derived from mandarin orange even in products and fields that could not be used due to the odor, or in products whose use amount was limited.
なお、特開２００３−１３４９９５号公報（特許文献１）には、柑橘缶詰用エッセンスの製法に関して、柑橘類の果皮由来のコールドプレスオイルを脱テルペン処理することにより該コールドプレスオイル中の香気成分（リモネン、リナロール、ヘキサナールなど）の濃度を調節することが記載され、脱テルペン処理法としては、減圧蒸留、エタノール抽出操作が挙げられている。具体的には、温州ミカン果皮よりコールドプレスオイルをエタノール溶液に添加、混合した後上層のテルペン層と下層の含水エタノール層に分離させ、濾紙によるろ過などにより含水エタノール層を分取することが記載されている。 JP-A-2003-134995 (Patent Document 1) discloses a method for producing an essence for canning citrus fruits by deterpening a cold press oil derived from citrus peel, and aroma component (limonene) in the cold press oil. , Linalool, hexanal, etc.) are described, and deterpene treatment methods include distillation under reduced pressure and ethanol extraction. Specifically, it is described that cold press oil is added to an ethanol solution from Unshu mandarin peel and separated, and then separated into an upper terpene layer and a lower aqueous ethanol layer, and the aqueous ethanol layer is separated by filtration with a filter paper, etc. Has been.
しかしながら、該公報に記載の方法では臭気が充分に除去できないなどの問題点がある。
また、特開２００２−３０９２８５号公報（特許文献２）には、加熱揮散させる芳香消臭剤用の香料組成物であって、天然香気に含有されるセスキテルペン系炭化水素化合物から選ばれる１種以上の香料を調合香料中特定量で含有する加熱揮散型芳香消臭剤用香料組成物が開示され、セスキテルペン系炭化水素化合物として、ライムオイル、レモンオイルなどが挙げられているが、それらの製法については何ら記載も示唆もされていない。
However, the method described in the publication has a problem that odor cannot be sufficiently removed.
JP-A-2002-309285 (Patent Document 2) discloses a fragrance composition for an aromatic deodorant that is volatilized by heating and is selected from sesquiterpene hydrocarbon compounds contained in natural aromas. Disclosed is a fragrance composition for a heat-volatile fragrance deodorant containing the above fragrance in a specific amount in a blended fragrance, and examples of sesquiterpene hydrocarbon compounds include lime oil and lemon oil. There is no description or suggestion about the production method.
さらに、特開２００３−９６４８６号公報（特許文献３）には、レモンフレーバーの主要香気成分であるシトラールが分解し不快臭の原因物質であるｐ−メチルアセトンに至る分解経路について詳述され、レモン、ライム、グレープフルーツ等の柑橘系フレーバーの香味を長期間保持すべく、香味劣化抑制剤として、茶ポリフェノールを添加することが記載されている。 Furthermore, JP-A-2003-96486 (Patent Document 3) details the decomposition pathway of citral, which is a main fragrance component of lemon flavor, to p-methylacetone, which is a causative substance of unpleasant odor, In order to maintain the flavor of citrus flavors such as lime and grapefruit for a long period of time, it is described that tea polyphenol is added as a flavor deterioration inhibitor.
しかしながら、該文献は、強すぎる柑橘系フレーバー自体を調整、低減しようとする技術に関するものではない。
本発明は、上記のような従来技術に伴う問題点を解決しようとするものであって酵素処理ヘスペリジンの特有の臭気を著しく低減したヘスペリジン組成物を提供することを目的としている。 The present invention is intended to solve the problems associated with the prior art as described above, and an object of the present invention is to provide a hesperidin composition in which the characteristic odor of enzyme-treated hesperidin is significantly reduced.
また本発明は、臭気を低減した酵素処理ヘスペリジンなどのヘスペリジン組成物の用途を提供することを目的としている。
また本発明は、臭気が低減された酵素処理ヘスペリジンなどのヘスペリジン組成物を安全かつ安価に効率的に製造する方法を提供することを目的としている。
Another object of the present invention is to provide a use of a hesperidin composition such as enzyme-treated hesperidin with reduced odor.
Another object of the present invention is to provide a method for efficiently and efficiently producing a hesperidin composition such as enzyme-treated hesperidin with reduced odor.
本発明に係る低臭気酵素処理ヘスペリジン組成物は、レモンより抽出されたヘスペリジン含有物に糖付与体の存在下でシクロデキストリングルカノトランスフェラ−ゼを作用させ、さらに、多孔性合成吸着樹脂、イオン交換樹脂、及びカーボン処理のうちの何れか１種以上による処理をして得られたものである。 The low odor enzyme-treated hesperidin composition according to the present invention allows a cyclodextrin glucanotransferase to act on a hesperidin-containing product extracted from lemon in the presence of a sugar donor, and further comprises a porous synthetic adsorption resin, an ion It is obtained by treatment with one or more of exchange resin and carbon treatment.
本発明に係る低臭気酵素処理ヘスペリジン組成物の製造に用いるヘスペリジン含有物は、国内外のレモン産地の冬場、すなわち秋から春にかけて収穫されるレモン種から抽出されることが好ましい。 The hesperidin-containing material used in the production of the low odor enzyme-treated hesperidin composition according to the present invention is preferably extracted from lemon species harvested from winter in domestic and overseas lemon producing regions, that is, from autumn to spring.
本発明に係る上記低臭気酵素処理ヘスペリジン組成物は、上記レモンより抽出されたヘスペリジン含有物がスラリー状であり、該ヘスペリジン含有物を常圧下に、７５〜１００℃の温度で１５〜６０分間加温した後で、上記糖付与体の存在下でシクロデキストリングルカノトランスフェラ−ゼを作用させる工程などを実施して得られたものであることが好ましい。 In the low odor enzyme-treated hesperidin composition according to the present invention, the hesperidin-containing material extracted from the lemon is in the form of a slurry, and the hesperidin-containing material is added at a temperature of 75 to 100 ° C. for 15 to 60 minutes under normal pressure. After warming, it is preferably obtained by carrying out a step of allowing cyclodextrin glucanotransferase to act in the presence of the sugar donor.
本発明に係る上記低臭気酵素処理ヘスペリジン組成物は、食品添加物、化粧品用添加物、医薬用添加物の何れかの用途に好適に使用される。
本発明に係る飲食物、化粧品または医薬品は、上記の酵素処理ヘスペリジンを含むことを特徴としている。
The low-odor enzyme-treated hesperidin composition according to the present invention is suitably used for any of food additives, cosmetic additives, and pharmaceutical additives.
A food, drink, cosmetic or pharmaceutical product according to the present invention is characterized by containing the enzyme-treated hesperidin.
本発明に係る低臭気酵素処理ヘスペリジン組成物の製造方法は、産地の秋から春に収穫するレモンの品種より抽出されたヘスペリジン含有物に糖付与体の存在下でシクロデキストリングルカノトランスフェラ−ゼを作用させ、さらに、多孔性合成吸着樹脂、イオン交換樹脂、及びカーボン処理のうちの何れか１種以上による処理を実施することを特徴としている。 The method for producing a low odor enzyme-treated hesperidin composition according to the present invention comprises cyclodextrin glucanotransferase in the presence of a sugar-donating substance in a hesperidin-containing product extracted from a variety of lemon harvested from autumn to spring in the production area. In addition, the treatment is further performed by one or more of a porous synthetic adsorption resin, an ion exchange resin, and a carbon treatment.
本発明に係る上記低臭気酵素処理ヘスペリジン組成物の製造方法は、上記レモンより抽出されたヘスペリジン含有物がスラリー状であり、該ヘスペリジン含有物を常圧下に、７５〜１００℃の温度で１５〜６０分間加温した後で、上記糖付与体の存在下でシクロデキストリングルカノトランスフェラ−ゼを作用させる工程を実施することが好ましい。 In the method for producing the low-odor enzyme-treated hesperidin composition according to the present invention, the hesperidin-containing material extracted from the lemon is in a slurry state, and the hesperidin-containing material is 15 to 15 at a temperature of 75 to 100 ° C. under normal pressure. After heating for 60 minutes, it is preferable to carry out a step of allowing cyclodextrin glucanotransferase to act in the presence of the sugar donor.
本発明によれば、臭気を低減した酵素処理ヘスペリジンなどのヘスペリジン組成物および該組成物の用途が提供される。
また本発明に係る上記製法によれば、臭気を低減した酵素処理ヘスペリジンなどのヘスペリジン組成物を安全かつ安価に効率的に製造することができる。
According to the present invention, hesperidin compositions such as enzyme-treated hesperidin with reduced odor and uses of the composition are provided.
Moreover, according to the said manufacturing method which concerns on this invention, hesperidin compositions, such as enzyme treatment hesperidin which reduced the odor, can be manufactured safely and cheaply efficiently.
以下、本発明に係る低臭気酵素処理ヘスペリジン組成物について具体的に説明する。
［低臭気酵素処理ヘスペリジン組成物］
本発明に係る酵素処理ヘスペリジンは、（Ａ）「柑橘類のうちのレモン、特に好ましくは冬場、すなわち秋から春に収穫するレモン品種より抽出されたヘスペリジン含有物に糖付与体の存在下でシクロデキストリングルカノトランスフェラ−ゼを作用」させ、さらに、（Ｃ）「多孔性合成吸着樹脂、イオン交換樹脂、及びカーボン処理のうちの何れか１種以上による処理」をして得られたものである。
Hereinafter, the low odor enzyme-treated hesperidin composition according to the present invention will be specifically described.
[Low odor enzyme-treated hesperidin composition]
The enzyme-treated hesperidin according to the present invention comprises (A) “a citrus lemon, particularly preferably a cyclodextrin in the presence of a sugar donor in a hesperidin-containing product extracted from a lemon variety that is harvested in winter, that is, from autumn to spring. Glucanotransferase is allowed to act ", and (C)" treatment with one or more of porous synthetic adsorption resin, ion exchange resin, and carbon treatment "is obtained. .
レモン由来のヘスペリジン含有物は、強いシトラール臭を有するのに対し、温州みかん由来のヘスペリジン抽出物はｄ−リモネンやリナロールを含むと考えられ、レモン由来のヘスペリジン含有物に比べて全体的に強い臭いを発する。また問題となる特異臭も同様にレモン由来のヘスペリジン含有物より、温州みかん由来のヘスペリジン抽出物の方が強い傾向を示す。シトラール、ｄ−リモネン、リナロールを含む強い臭いはその後の多孔性合成吸着樹脂、イオン交換樹脂、及びカーボン処理の何れかの処理工程（Ｃ）で、（そのメカニズムは不明であるが）除去され易いため、最終製品には残らない。しかし、シトラール、ｄ−リモネン、リナロール臭以外の強い臭気である特異臭は上記多孔性合成吸着樹脂、イオン交換樹脂及びカーボン処理では充分除去されにくいため最終製品に残り、不快臭として感じられる。 The hesperidin-containing product derived from lemon has a strong citral odor, whereas the hesperidin extract derived from Wenzhou mandarin orange is considered to contain d-limonene and linalool, and has an overall strong odor compared to the hesperidin-containing product derived from lemon. To emit. In addition, the specific odor which is a problem also shows that the extract of hesperidin derived from Unshu mandarin orange has a stronger tendency than the one containing lemon-derived hesperidin. Strong odors including citral, d-limonene, and linalool are easily removed (although the mechanism is unknown) in any of the subsequent porous synthetic adsorption resin, ion exchange resin, and carbon treatment (C). Therefore, it does not remain in the final product. However, the specific odor, which is a strong odor other than citral, d-limonene, and linalool odor, remains in the final product and is felt as an unpleasant odor because it is not sufficiently removed by the porous synthetic adsorption resin, ion exchange resin and carbon treatment.
また、一般的に冬場（国内外を問わず、レモン産地の季節（四季）のうちで低温時期）に収穫されるレモンの品種から抽出した精油成分は夏場（レモン産地の季節（四季）のうちで高温時期、すなわち夏場）に収穫されたものに比べて匂いの質が優れていると言われているが、レモン由来のヘスペリジン含有物においても秋から春（冬場）に収穫されたレモンの品種より抽出されたものは、春から秋（夏場）に収穫されたレモンの品種より抽出されたものより特異臭が少ないことがわかった。これは精油成分の質の違いに関係するものと思われる。さらに糖転移反応前に一定条件下でレモン由来のヘスペリジン含有物を加熱処理することにより、ヘスペリジン含有物中の特異臭が揮発により低減されるため、最終製品中の特異臭が著しく少ない低臭気酵素処理ヘスペリジン組成物の製造が可能となる。 In addition, the essential oil components extracted from the varieties of lemons that are generally harvested in winter (low temperature seasons in the seasons of lemon production (seasonal), regardless of domestic or overseas) It is said that the odor quality is superior to those harvested in the high temperature period, that is, summer), but the lemon varieties that are harvested from autumn to spring (winter) in the case of lemon-containing hesperidin It was found that the more extracted one had less specific odor than the one extracted from the variety of lemons harvested from spring to autumn (summer). This seems to be related to the difference in the quality of the essential oil components. Furthermore, by heat-treating lemon-derived hesperidin-containing products under certain conditions prior to the transglycosylation reaction, the specific odor in the hesperidin-containing product is reduced by volatilization, so the low-odor enzyme with significantly less specific odor in the final product A treated hesperidin composition can be produced.
以下、上記の酵素処理ヘスペリジンの製法に則して詳説する。
用いられるレモン由来のヘスペリジン含有物は、特に秋から春に収穫するレモンの品種から抽出されたものが好ましく、代表的な品種としてフィノ、ジェノバ、フェミネロオバ−レ、モナチェロなどから抽出されたものであればレモンの栽培地に影響されず、例えばカリフォルニア、ニュージーランド、イタリア、スペイン、ポルトガル、モロッコ、フランスなどで栽培されたどれを利用してもよい。一般的にヘスペリジン含有物は、レモンの果皮・果汁・種子をアルカリ抽出し、ろ過により固形物を除去した後に酸性条件下で析出させるなど、従来より公知の方法で得られる。
Hereinafter, it explains in full detail according to the manufacturing method of said enzyme-treated hesperidin.
The lemon-containing hesperidin-containing material used is preferably one extracted from a variety of lemons harvested from autumn to spring, especially those extracted from fino, genoa, feminero ovale, monacello, etc. For example, any of those cultivated in California, New Zealand, Italy, Spain, Portugal, Morocco, France, etc. may be used without being influenced by the lemon growing place. In general, the hesperidin-containing material is obtained by a conventionally known method such as alkali extraction of lemon peel, fruit juice, and seeds, removal of solid matter by filtration, and precipitation under acidic conditions.
特に本発明では、上記レモンより抽出されたヘスペリジン含有物が、通常ヘスペリジンの他に微量のミネラル、色素、精油成分、臭気成分などを含む粉末であり、この水に不溶なヘスペリジン含有物から効率よく特有の臭い成分を除く方法として、温水に臭い成分を溶解させ揮発させる点からスラリ−状にして臭気揮発・除去に供することが好ましい。さらに詳しくはこのスラリ−を常圧下に、７５〜１００℃、好ましくは８０〜９０℃の温度で、１５〜６０分間、好ましくは２０〜４０分間加温する工程（Ｂ）を実施したのちに、酵素処理工程（Ａ）に移ることで、原料中の特有の臭気成分が効率よく揮発・除去される。 In particular, in the present invention, the hesperidin-containing product extracted from the lemon is usually a powder containing trace amounts of minerals, pigments, essential oil components, odor components, etc. in addition to hesperidin. As a method for removing the characteristic odor component, it is preferable to use it in the form of a slurry to evaporate and remove the odor from the point of dissolving and volatilizing the odor component in warm water. More specifically, after carrying out the step (B) of heating this slurry under normal pressure at a temperature of 75 to 100 ° C., preferably 80 to 90 ° C. for 15 to 60 minutes, preferably 20 to 40 minutes, By moving to the enzyme treatment step (A), the characteristic odor component in the raw material is efficiently volatilized and removed.
なお、この加熱処理工程（Ｂ）は、「酵素処理工程（Ａ）」を実施した後に実施すると、特異臭が揮発・除去されにくく最終製品まで残りやすいため酵素処理（Ａ）の前に行うことが望ましい。 This heat treatment step (B) should be performed before the enzyme treatment (A) because when the “enzyme treatment step (A)” is carried out, the specific odor is difficult to volatilize and be removed and the final product is likely to remain. Is desirable.
本発明では、このレモン由来のヘスペリジン含有物（抽出物）に、デンプン等の糖付与体の存在下でシクロデキストリングルカノトランスフェラーゼ等の糖転移酵素、好ましくはシクロデキストリングルカノトランスフェラーゼを作用させて酵素処理ヘスペリジン（α-グルコシルヘスペリジン）などが含まれたレモン系グルコシル化合物（酵素処理レモ
ンヘスペリジン）含有物を得る。
In the present invention, a glycosyltransferase such as cyclodextrin glucanotransferase, preferably cyclodextrin glucanotransferase is allowed to act on this lemon-derived hesperidin-containing product (extract) in the presence of a sugar-imparting substance such as starch. A lemon-based glucosyl compound (enzyme-treated lemon hesperidin) -containing product containing treated hesperidin (α-glucosyl hesperidin) and the like is obtained.
酵素処理ヘスペリジン（含有物）の製造法自体としては、特開平３−７５９３号公報（特許文献１）の記載に準じて、レモンヘスペリジン抽出物とα−グルコシル糖化合物（デンプン部分分解物）とを含有する水溶液に上記したような糖転移酵素を作用させて酵素処理レモンヘスペリジン（反応混合物）を生成させる方法が挙げられる。 As the method for producing the enzyme-treated hesperidin (containing material) itself, a lemon hesperidin extract and an α-glucosyl sugar compound (starch partially decomposed product) are used according to the description in JP-A-3-7593 (Patent Document 1). Examples thereof include a method of producing an enzyme-treated lemon hesperidin (reaction mixture) by allowing a glycosyltransferase as described above to act on the aqueous solution to be contained.
上記α−グルコシル糖化合物としては、従来より公知のアミロース、デキストリン、シクロデキストリン等が挙げられる。
次いで、このような酵素処理レモンヘスペリジン（α-グルコシルヘスペリジン）が含
まれた反応混合物は、本発明では、多孔性合成吸着樹脂、イオン交換樹脂、及びカーボン処理のうちの何れか１種以上の処理（Ｃ）に供する。このように、得られた反応混合物の多孔性合成樹脂による処理などを行うと、臭気成分、不純物がより一層低減された処理物が得られる。
Examples of the α-glucosyl sugar compound include conventionally known amylose, dextrin, cyclodextrin and the like.
Subsequently, in the present invention, the reaction mixture containing such enzyme-treated lemon hesperidin (α-glucosyl hesperidin) is treated with one or more of a porous synthetic adsorption resin, an ion exchange resin, and a carbon treatment. Use for (C). Thus, when the obtained reaction mixture is treated with a porous synthetic resin, a treated product in which odor components and impurities are further reduced is obtained.
なお上記多孔性合成樹脂に加えて、イオン交換樹脂、活性炭などを用いて臭気成分、色素類などの低減処理をしてもよい。
本発明の好ましい態様では、例えば、多孔性合成樹脂により処理された後、さらにイオン交換樹脂、活性炭の何れか１種または２種、好ましくは両方にて処理されているものが酵素処理ヘスペリジン固有の臭気をより顕著に低減する効果が得られる点で望ましい。
In addition to the porous synthetic resin, ion exchange resin, activated carbon, or the like may be used to reduce odor components and pigments.
In a preferred embodiment of the present invention, for example, after being treated with a porous synthetic resin, further treated with one or two types of ion exchange resin and activated carbon, preferably both, is inherent to the enzyme-treated hesperidin. It is desirable in that the effect of significantly reducing the odor is obtained.
多孔性吸着樹脂材としては、酵素処理レモンヘスペリジン反応混合物中のデンプン分解物および臭い成分を除去できれば無極性樹脂、中間極性樹脂の何れでもよい。
具体的には、例えば無極性樹脂としてＨＰ−１０，ＨＰ−２０，ＨＰ−５０（三菱化成（株）製）、中間極性としてＸＡＤ−７（オルガノ（株）製）が挙げられる。
The porous adsorbent resin material may be either a nonpolar resin or an intermediate polar resin as long as it can remove starch degradation products and odorous components in the enzyme-treated lemon hesperidin reaction mixture.
Specifically, for example, HP-10, HP-20, and HP-50 (manufactured by Mitsubishi Kasei Co., Ltd.) are used as nonpolar resins, and XAD-7 (manufactured by Organo Corporation) is used as an intermediate polarity.
［低臭気酵素処理ヘスペリジン組成物の用途］
このように酵素処理に加えて、樹脂による吸着処理等も行って得られた本発明に係る低臭気酵素処理ヘスペリジン組成物は、毛細血管の強化、出血予防、血圧調整などの生理作用を持つビタミンＰ様物質としての機能を有し、柑橘由来の特異臭が著しく低減、除去されており、食品添加物、化粧品用添加物、医薬用添加物などとして、飲食物、医薬品、化粧品など極めて広い範囲で利用される。
[Use of low-odor enzyme-treated hesperidin composition]
Thus, the low-odor enzyme-treated hesperidin composition according to the present invention obtained by performing adsorption treatment with a resin in addition to enzyme treatment is a vitamin having physiological effects such as strengthening of capillaries, prevention of bleeding, and blood pressure adjustment. It has a function as a P-like substance, and the specific odor derived from citrus has been remarkably reduced and removed. As a food additive, cosmetic additive, pharmaceutical additive, etc., a very wide range of foods, pharmaceuticals, cosmetics, etc. Used in
このように、その安全性が確認されている酵素処理ヘスペリジンなどを含む本発明の低臭気酵素処理ヘスペリジン組成物は、それらの特性を生かして、例えば、食品用添加物、化粧品用添加物、医薬用添加物、ビタミンＰ強化剤、健康補助食品等として好適に用いることができる。 As described above, the low-odor enzyme-treated hesperidin composition of the present invention containing the enzyme-treated hesperidin and the like whose safety has been confirmed makes use of these characteristics, for example, food additives, cosmetic additives, pharmaceuticals, etc. It can be suitably used as an additive, vitamin P fortifier, health supplement, and the like.
この低臭気酵素処理ヘスペリジン組成物は、その用途に応じて、任意の剤型を採ることができる。また、この低臭気酵素処理ヘスペリジン組成物は、飲食物、化粧品、医薬品または飼料などに、任意量で添加して用いることができ、例えば、健康飲料に代表される飲食物などの中に含まれる固形分に対して、酵素処理ヘスペリジンの固形分として０．０１〜９９．９重量％となるような量で、また、例えば、飲料１００ｍｌに対して０．０００１％〜５％ 程度となるような量で添加して用いることもできる。 This low-odor enzyme-treated hesperidin composition can take any dosage form depending on its application. In addition, the low-odor enzyme-treated hesperidin composition can be used by adding it in any amount to foods, cosmetics, pharmaceuticals, feeds, etc., for example, included in foods and drinks represented by health drinks, etc. The amount of the enzyme-treated hesperidin is 0.01 to 99.9% by weight with respect to the solid content, for example, about 0.0001% to 5% with respect to 100 ml of beverage. It can also be used by adding in an amount.
飲食物としては、例えば、酸性飲料、例えば、酢飲料、乳酸飲料、柑橘飲料、酸性野菜飲料、（酸性の）生薬含有飲料などが挙げられる。
［実施例］
以下、本発明に係る低臭気酵素処理ヘスペリジン組成物、その製法及びその用途について実施例によりさらに具体的に説明するが、本発明は係る実施例により何ら限定されるものではない。
Examples of the food and drink include acidic beverages such as vinegar beverages, lactic acid beverages, citrus beverages, acidic vegetable beverages, and (acidic) herbal medicine-containing beverages.
[Example]
Hereinafter, the low odor enzyme-treated hesperidin composition according to the present invention, its production method and its use will be described more specifically with reference to examples, but the present invention is not limited to these examples.
なお、以下の試験例等の記載において、柑橘類としてレモンを用いた試験例は、本発明の実施例に相当し、温州みかんを用いた試験例は、参考例あるいは比較例に相当する。
［試験例１］
フィノ種のレモン果皮1重量部当たりに水１０重量部の量で加え、さらにアルカリ（苛
性ソ−ダ）を加えてｐＨ１２のアルカリ液に調整した後、５０℃で２時間攪拌しながら抽出を行った。ろ過により残渣を除去した後、塩酸でｐＨ３．０に下げヘスペリジンを析出させた後、固液分離、乾燥してヘスペリジン含有物を得た。
In the description of the following test examples, the test examples using lemon as citrus fruits correspond to the examples of the present invention, and the test examples using Unshu mandarin oranges correspond to reference examples or comparative examples.
[Test Example 1]
Add 10 parts by weight of water per 1 part by weight of Fino lemon peel, add alkali (caustic soda) to adjust to an alkaline solution of pH 12, and then extract with stirring at 50 ° C for 2 hours. It was. After removing the residue by filtration, the pH was lowered to 3.0 with hydrochloric acid to precipitate hesperidin, followed by solid-liquid separation and drying to obtain a hesperidin-containing product.
このヘスペリジン含有物（イ）１重量部に水５，０００（5千）重量部を加え、常圧下
、温度８０℃で３０分間加熱処理を行った。
次に、得られたスラリ−をアルカリ溶解した後、デキストリン（ＤＥ２０）６重量部を加え加熱溶解させ、これにシクロマルトデキストリングルカノトランスフェラ−ゼをデキストリン１ｇ当たり３０単位加え、ｐＨ６．０、７０℃に維持して１８時間反応させ、酵素処理ヘスペリジン反応液を得た。
5,000 (5,000) parts by weight of water was added to 1 part by weight of this hesperidin-containing material (ii), and a heat treatment was performed at 80 ° C. for 30 minutes under normal pressure.
Next, after the obtained slurry was dissolved in an alkali, 6 parts by weight of dextrin (DE20) was added and dissolved by heating, to which 30 units of cyclomaltodextrin glucanotransferase was added per 1 g of dextrin, pH 6.0, The reaction was carried out for 18 hours while maintaining at 70 ° C. to obtain an enzyme-treated hesperidin reaction solution.
この反応液を多孔性合成樹脂吸着剤（商品名「ＨＰ−１０」、三菱化成(株)製）が充填されたカラムにＳＶ２．０で通液し、酵素処理ヘスペリジンを吸着させた。
次いで、このカラムを水で洗浄しデキストリン分解物、臭い物質を洗浄・除去した後、５０ ｖ／ｖ％エタノ−ルを通液し酵素処理ヘスペリジンなどを脱着した。得られた脱着液を濃縮して溶出液中のエタノ−ルを留去し、乾燥粉末を得た。
This reaction solution was passed through a column packed with a porous synthetic resin adsorbent (trade name “HP-10”, manufactured by Mitsubishi Kasei Co., Ltd.) at SV 2.0 to adsorb enzyme-treated hesperidin.
Next, this column was washed with water to wash and remove dextrin degradation products and odorous substances, and then passed 50 v / v% ethanol to desorb enzyme-treated hesperidin and the like. The obtained desorption solution was concentrated to remove ethanol in the eluate to obtain a dry powder.
次いで、この乾燥粉末１重量部にイオン交換水１０重量部を加えて温度６０℃に加熱し、含まれる固形分（すなわち酵素処理ヘスペリジン）を溶解させた後、約３０℃に冷却して強酸性陽イオン交換樹脂（商品名「ダイアイオンＳＫ１Ｂ」、三菱化成(株)製）と強塩基性イオン交換樹脂（商品名「ダイアイオンＳＡ１０Ａ」、三菱化成(株)製）に接触させて脱塩、脱臭、脱色を行った。 Next, 10 parts by weight of ion-exchanged water is added to 1 part by weight of this dry powder and heated to a temperature of 60 ° C. to dissolve the contained solids (ie, enzyme-treated hesperidin), and then cooled to about 30 ° C. to become strongly acidic. Desalting by contacting with a cation exchange resin (trade name “Diaion SK1B”, manufactured by Mitsubishi Kasei Co., Ltd.) and a strongly basic ion exchange resin (trade name “Diaion SA10A”, manufactured by Mitsubishi Kasei Co., Ltd.) Deodorized and decolorized.
得られた流出液に粉末活性炭（商品名「精製白鷺」、武田食品工業（株）製）０．０１重量部を添加し６０℃で１時間攪拌した。次いで、ろ過により粉末活性炭を除去した後、濃縮・乾燥し、酵素処理レモンヘスペリジン粉末（ロ）を得た。この粉末１重量部にイオン交換水１０重量部を加えて温度６０℃に加温・溶解した液を試料Ａとした。 To the obtained effluent, 0.01 part by weight of powdered activated carbon (trade name “Purified Shirakaba”, manufactured by Takeda Food Industry Co., Ltd.) was added and stirred at 60 ° C. for 1 hour. Subsequently, after removing activated carbon powder by filtration, it was concentrated and dried to obtain enzyme-treated lemon hesperidin powder (b). Sample A was prepared by adding 10 parts by weight of ion-exchanged water to 1 part by weight of this powder and heating and dissolving at a temperature of 60 ° C.
同様に、温州みかん抽出ヘスペリジン含有物（ハ）も上記の操作を行い、酵素処理みかんヘスペリジン粉末（ニ）を得た後、この粉末１重量部にイオン交換水１０重量部を加えて温度６０℃に加温・溶解した液を試料Ｂとした。 Similarly, the hesperidin-containing hesperidin-containing material (c) was also subjected to the above operation to obtain enzyme-treated mandarin hesperidin powder (d), and then 10 parts by weight of ion-exchanged water was added to 1 part by weight of the powder, and the temperature was 60 ° C. The solution heated and dissolved in was used as Sample B.
試料Ａ、Ｂおよび対照の各５０ｍｌを、１００ｍｌのスクリューキャップ付三角フラスコに充填し、密栓して４０℃で２日（４８時間）保温した後、液温４０℃、パネラー８人にて官能検査を行った。その平均値を表１に示す。同様に室温（１８〜２３℃）で２日（４８時間）保存した後、室温で行った官能検査の平均値を表２に示す。 50 ml of each of Samples A and B and the control were filled into a 100 ml Erlenmeyer flask with a screw cap, sealed, and kept at 40 ° C. for 2 days (48 hours), followed by a sensory test with 8 panelists at a liquid temperature of 40 ° C. Went. The average value is shown in Table 1. Similarly, after storing at room temperature (18-23 ° C.) for 2 days (48 hours), the average value of the sensory test conducted at room temperature is shown in Table 2.
［試験例２］
酵素処理レモンヘスペリジン粉末（ロ）と酵素処理みかんヘスペリジン粉末（ニ）を次の配合量で使用して清涼飲料水を調製した。なお、酵素処理レモンヘスペリジン粉末（ロ）粉末を用いた清涼飲料水を試料Ｃ、酵素処理みかんヘスペリジン粉末（ニ）を用いた清涼飲料水を試料Ｄとした。
[Test Example 2]
A soft drink was prepared using enzyme-treated lemon hesperidin powder (b) and enzyme-treated mandarin hesperidin powder (d) in the following amounts. The soft drink using the enzyme-treated lemon hesperidin powder (b) powder was sample C, and the soft drink using the enzyme-treated mandarin hesperidin powder (d) was sample D.
上記清涼飲料水について、官能検査を行った。なお、官能検査はパネラー８人で行った。
その８人による官能検査の評価の平均値を表３に示す。
A sensory test was performed on the soft drink. The sensory test was conducted by 8 panelists.
Table 3 shows the average values of sensory test evaluations by the eight persons.
〈清涼飲料水の配合組成〉
〈試料Ｃ〉
（材 料） （含有量：g）
水 １９５．０２
砂糖 ３．０
酵素処理ステビア ０．１
レモンフレ−バ− ０．１
酸味料 １．０
カラギ−ナン ０．０２
ビタミンＣ ０．０６
酵素処理レモンヘスペリジン粉末（ロ） ０．７
合 計 ２００．０
〈試料Ｄ〉
（材 料） （含有量 g）
水 １９５．０２
砂糖 ３．０
酵素処理ステビア ０．１
レモンフレ−バ− ０．１
酸味料 １．０
カラギ−ナン ０．０２
ビタミンＣ ０．０６
酵素処理みかんヘスペリジン粉末（ニ） ０．７
合 計 ２００．０
<Combination composition of soft drinks>
<Sample C>
(Material) (Content: g)
Water 195.02
Sugar 3.0
Enzyme-treated stevia 0.1
Lemon flavor 0.1
Acidulant 1.0
Carrageenan 0.02
Vitamin C 0.06
Enzyme-treated lemon hesperidin powder (b) 0.7
Total 200.0
<Sample D>
(Material) (Content g)
Water 195.02
Sugar 3.0
Enzyme-treated stevia 0.1
Lemon flavor 0.1
Acidulant 1.0
Carrageenan 0.02
Vitamin C 0.06
Enzyme-treated mandarin hesperidin powder (d) 0.7
Total 200.0
［試験例３］
酵素処理レモンヘスペリジン粉末（ロ）と酵素処理みかんヘスペリジン粉末（ニ）を次の配合量で使用してゼリーを調製した。なお、酵素処理レモンヘスペリジン粉末（ロ）を用いたゼリーを試料Ｅ、酵素処理みかんヘスペリジン粉末（ニ）を用いたゼリーを試料Ｆとした。
[Test Example 3]
A jelly was prepared using enzyme-treated lemon hesperidin powder (b) and enzyme-treated tangerine hesperidin powder (d) in the following amounts. The jelly using the enzyme-treated lemon hesperidin powder (b) was designated as sample E, and the jelly using the enzyme-treated mandarin orange hesperidin powder (d) was designated as sample F.
上記ゼリーについて、官能検査を行った。なお、官能検査はパネラー８人で行った。
その８人による官能検査の評価の平均値を表４に示す。
〈ゼリ−の配合組成〉
〈試料Ｅ〉
（材 料） （含有量 g）
水 １８４．６３９
砂糖 １０．０
酵素処理ステビア ０．１
アップルフレ−バ− ０．１
ベニバナ色素 ０．００１
酸味料 ０．４
ゲル化剤 ４．０
ビタミンＣ ０．０６
酵素処理レモンヘスペリジン粉末（ロ） ０．７
合 計 ２００．０
〈試料Ｆ〉
（材 料） （含有量 g）
水 １８４．６３９
砂糖 １０．０
酵素処理ステビア ０．１
アップルフレ−バ− ０．１
ベニバナ色素 ０．００１
酸味料 ０．４
ゲル化剤 ４．０
ビタミンＣ ０．０６
酵素処理みかんヘスペリジン粉末（ニ） ０．７
合 計 ２００．０
A sensory test was performed on the jelly. The sensory test was conducted by 8 panelists.
Table 4 shows the average values of sensory test evaluations by the eight persons.
<Combination composition of jelly>
<Sample E>
(Material) (Content g)
Water 184.639
Sugar 10.0
Enzyme-treated stevia 0.1
Apple flavor 0.1
Safflower pigment 0.001
Acidulant 0.4
Gelling agent 4.0
Vitamin C 0.06
Enzyme-treated lemon hesperidin powder (b) 0.7
Total 200.0
<Sample F>
(Material) (Content g)
Water 184.639
Sugar 10.0
Enzyme-treated stevia 0.1
Apple flavor 0.1
Safflower pigment 0.001
Acidulant 0.4
Gelling agent 4.0
Vitamin C 0.06
Enzyme-treated mandarin hesperidin powder (d) 0.7
Total 200.0
Claims (7)
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007143413A (en) * | 2005-11-24 | 2007-06-14 | Maruzen Pharmaceut Co Ltd | Method for eliminating unfavorable smell-causing component and bitter taste component, method for producing quillai extract, and quillai extract |
| KR101119311B1 (en) * | 2009-12-02 | 2012-03-16 | 한국식품연구원 | Purification method of hesperidin from mandarin peel |
| JP2012077051A (en) * | 2010-10-05 | 2012-04-19 | Kao Corp | Method for producing hesperidin composition |
| CN115024458A (en) * | 2022-06-14 | 2022-09-09 | 上海龙殷生物科技有限公司 | A method for improving taste and bitter taste of extract of plant of Rutaceae and Citrus |
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| JPS54101412A (en) * | 1978-01-25 | 1979-08-10 | Nippon Shinyaku Co Ltd | Preparation of vitamin p |
| JPH037593A (en) * | 1989-06-03 | 1991-01-14 | Hayashibara Biochem Lab Inc | Alpha-glycosyl hesperidin, production and use thereof |
| JP2001521003A (en) * | 1997-10-28 | 2001-11-06 | コリア インスティテュート オブ サイエンス アンド テクノロジー | Acyl COA-cholesterol-O-acyl transferase inhibitor, inhibitor of macrophage-lipid complex accumulation on arterial wall, and citrus peel extract as agent for preventing or treating liver disease |
| JP2003169631A (en) * | 2001-12-07 | 2003-06-17 | Snow Brand Milk Prod Co Ltd | Anti-allergic drink or food |
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2004
- 2004-06-07 JP JP2004168631A patent/JP4731835B2/en not_active Expired - Lifetime
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54101412A (en) * | 1978-01-25 | 1979-08-10 | Nippon Shinyaku Co Ltd | Preparation of vitamin p |
| JPH037593A (en) * | 1989-06-03 | 1991-01-14 | Hayashibara Biochem Lab Inc | Alpha-glycosyl hesperidin, production and use thereof |
| JP2001521003A (en) * | 1997-10-28 | 2001-11-06 | コリア インスティテュート オブ サイエンス アンド テクノロジー | Acyl COA-cholesterol-O-acyl transferase inhibitor, inhibitor of macrophage-lipid complex accumulation on arterial wall, and citrus peel extract as agent for preventing or treating liver disease |
| JP2003169631A (en) * | 2001-12-07 | 2003-06-17 | Snow Brand Milk Prod Co Ltd | Anti-allergic drink or food |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007143413A (en) * | 2005-11-24 | 2007-06-14 | Maruzen Pharmaceut Co Ltd | Method for eliminating unfavorable smell-causing component and bitter taste component, method for producing quillai extract, and quillai extract |
| KR101119311B1 (en) * | 2009-12-02 | 2012-03-16 | 한국식품연구원 | Purification method of hesperidin from mandarin peel |
| JP2012077051A (en) * | 2010-10-05 | 2012-04-19 | Kao Corp | Method for producing hesperidin composition |
| CN115024458A (en) * | 2022-06-14 | 2022-09-09 | 上海龙殷生物科技有限公司 | A method for improving taste and bitter taste of extract of plant of Rutaceae and Citrus |
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| Publication number | Publication date |
|---|---|
| JP4731835B2 (en) | 2011-07-27 |
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