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JPH0260306B2 - - Google Patents
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JPH0260306B2 - - Google Patents

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Publication number
JPH0260306B2
JPH0260306B2 JP58151351A JP15135183A JPH0260306B2 JP H0260306 B2 JPH0260306 B2 JP H0260306B2 JP 58151351 A JP58151351 A JP 58151351A JP 15135183 A JP15135183 A JP 15135183A JP H0260306 B2 JPH0260306 B2 JP H0260306B2
Authority
JP
Japan
Prior art keywords
monolinolein
blood cholesterol
effect
suppressing
lowering
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.)
Expired - Lifetime
Application number
JP58151351A
Other languages
Japanese (ja)
Other versions
JPS6043368A (en
Inventor
Yoshio Maekawa
Hirohisa Suzuki
Takaaki Kobayashi
Seikichi Sekine
Ichiro Ono
Yoshinari Shimoda
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Ajinomoto Co Inc
Original Assignee
Ajinomoto Co Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Ajinomoto Co Inc filed Critical Ajinomoto Co Inc
Priority to JP58151351A priority Critical patent/JPS6043368A/en
Priority to EP83305367A priority patent/EP0104043A3/en
Publication of JPS6043368A publication Critical patent/JPS6043368A/en
Publication of JPH0260306B2 publication Critical patent/JPH0260306B2/ja
Granted legal-status Critical Current

Links

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  • Dairy Products (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Non-Alcoholic Beverages (AREA)

Description

【発明の詳細な説明】[Detailed description of the invention]

本発明は血中コレステロールの低下または上昇
抑制作用を有した飲料に関するものである。本発
明でいう飲料は、豆乳、牛乳、果汁、清涼飲料、
栄養飲料、炭酸飲料などをいう。ここでいう血中
コレステロールを低下させる作用とは血中コレス
テロール濃度が通常より高いものに対し、これを
低下させる作用をいいまた血中コレステロールの
上昇を抑制する作用とはコレステロールを多量に
含む食品を摂取しても、恒常的に血中コレステロ
ールが上昇することを抑える作用をいう。 従来の数多くの知見を基にすると、植物油中の
多価不飽和脂肪酸(リノール酸など)や植物ステ
ロールなどはヒトや他の動物の血中コレステロー
ルを低下または上昇抑制作用を有することは良く
知られている。近年、この種の物質が食品または
飲料に栄養改善を目的に補足強化された健康食品
として実用化されてきた。 本発明者らは、従来より明らかにされた上記物
質以外の油脂成分の生理効果の有無に注目し、
種々検討した結果、モノグリセリドの一種のモノ
リノレインには従来の物質に比し100分の1の量
で血中コレステロールの低下作用および上昇抑制
作用が同等の効果を示すことを見出し、本発明を
完成した。すなわち、本発明は飲料中にモノリノ
レインを0.1重量%ないし30重量%含有せしめた
飲料である。 ここでいうモノリノレインはα−モノリノレイ
ンおよび/またはβ−モノリノレインをいう。特
にβ−モノリノレインに優れた効果がある。 本発明に用いるモノリノレインの調製法には特
に制限はなく、天然モノグリセリドの濃縮または
分取のほか、アルカリ類やP−トルエンスルホン
酸等の触媒または酵素を用いたグリセリンの直接
エステル化、エステル交換およびトリグリセイ
ド、ジグリセイドの部分加水分解をはじめ公知の
合成法が利用でき、さらにこれらを組み合わせて
用いてもよい。 このようにして得られたモノリノレインは、そ
のままでもまた水や油脂類に溶解あるいは分散さ
せて用いることもでき、広範囲の飲料に添加が可
能であり、しかも少量の添加で血中コレステロー
ルを低下させるまたは上昇を抑制するから食生活
を改善に寄与するところ大である。 本発明によれば水を主成分とした溶得にモノリ
ノレインを0.1%〜30%、好ましくは1%〜5%
溶解あるいは分散させることにより、血中コレス
テロールを低下または上昇を抑制する作用を有す
る健康食料を製造することができる。この際、モ
ノリノレイン以外のグリセリン脂肪酸エステル、
シヨ糖脂肪酸エステル、ソルビタン脂肪酸エステ
ル、レシチンなどの乳化剤を用いることも可能で
ある。 本発明者らの以前の出願(特開昭57−35517号、
特開昭57−36935号、特開昭57−36936号、特開昭
57−39736号および特開昭57−42631号)に記載さ
れた発明の組成物および食用油脂に含まれる有効
生物中にはモノリノレインの他に、植物ステロー
ル及びジグリセライドを多量に含み半固型状であ
るので、これを油脂に含有させても味風味の好ま
しい飲料が得られない。ジグリセライドまたは植
物ステロールの含量はモノリノレインに対して重
量比で好ましくは5倍以下にするのがよい。 以下実施例により本発明を具体的に説明する。 実施例 1 (1) モノリノレインの調製法 −コーン油からの調製− 精製コーン油1Kgに10Kgのメチルエチルケト
ンを加えて撹拌した後、ドライアイス・メタノ
ール冷媒にて−70℃で3時間冷却した。その
後、固結物を吸引濾過により除去したメチルエ
チルケトン溶液からメチルエチルケトンをエバ
ポレータに留去し、赤かつ色の液体を得た。こ
れに10倍重量のメチルエチルケトンを加え、再
度同じ方法にて低温固結性物質を除き、メチル
エチルケトンを留去して赤かつ色の高粘度液体
25gを得た。 さらにこの物質22gを、活性化した「ワコー
ゲルC−200」1500gを充填した内径70mmのガ
ラスカラムにより第1表の溶剤にて順次展開
し、それぞれの区分を回収後、溶剤を留去し、
第2表に示すような4つのカラムの分画物質を
得た。
TECHNICAL FIELD The present invention relates to a beverage that has the effect of lowering or suppressing the increase in blood cholesterol. Beverages referred to in the present invention include soy milk, milk, fruit juice, soft drinks,
Refers to nutritional drinks, carbonated drinks, etc. The effect of lowering blood cholesterol here refers to the effect of lowering blood cholesterol concentration in those whose blood cholesterol concentration is higher than normal, and the effect of suppressing the increase in blood cholesterol refers to the effect of reducing blood cholesterol concentration in those who have higher than normal blood cholesterol concentration. It has the effect of suppressing the constant rise in blood cholesterol even when ingested. Based on a large amount of conventional knowledge, it is well known that polyunsaturated fatty acids (such as linoleic acid) and plant sterols in vegetable oils have the effect of lowering or suppressing the increase in blood cholesterol in humans and other animals. ing. In recent years, this type of substance has been put into practical use as a supplemented and fortified health food in foods or drinks for the purpose of improving nutrition. The present inventors focused on the presence or absence of physiological effects of oil and fat components other than the above-mentioned substances that have been clarified in the past,
As a result of various studies, we discovered that monolinolein, a type of monoglyceride, has the same effect on lowering and suppressing blood cholesterol levels as conventional substances at 1/100th the amount, and completed the present invention. did. That is, the present invention is a beverage containing 0.1% to 30% by weight of monolinolein. Monolinolein as used herein refers to α-monolinolein and/or β-monolinolein. In particular, β-monolinolein has excellent effects. There are no particular restrictions on the method for preparing monolinolein used in the present invention, and in addition to concentration or fractionation of natural monoglycerides, direct esterification and transesterification of glycerin using an alkali or a catalyst such as P-toluenesulfonic acid or an enzyme. Known synthetic methods including partial hydrolysis of triglyceride and diglyceride can be used, and combinations of these methods may also be used. The monolinolein obtained in this way can be used as it is or dissolved or dispersed in water or fats and oils, and can be added to a wide range of beverages, and even a small amount of it can lower blood cholesterol. It also greatly contributes to improving your eating habits because it suppresses the increase. According to the present invention, monolinolein is added in an amount of 0.1% to 30%, preferably 1% to 5%, in a water-based solution.
By dissolving or dispersing it, it is possible to produce a health food that has the effect of lowering or suppressing the increase in blood cholesterol. At this time, glycerin fatty acid esters other than monolinolein,
It is also possible to use emulsifiers such as sucrose fatty acid ester, sorbitan fatty acid ester, and lecithin. The inventors' previous application (Japanese Patent Application Laid-Open No. 57-35517,
JP-A-57-36935, JP-A-57-36936, JP-A-Sho
In addition to monolinolein, the effective organisms contained in the compositions and edible fats and oils of the invention described in Japanese Patent Application Laid-Open No. 57-39736 and JP-A No. 57-42631 contain large amounts of plant sterols and diglycerides, which are semi-solid. Therefore, even if it is included in fats and oils, a beverage with a favorable taste and flavor cannot be obtained. The content of diglyceride or plant sterol is preferably 5 times or less by weight relative to monolinolein. The present invention will be specifically explained below using Examples. Example 1 (1) Method for preparing monolinolein - Preparation from corn oil - After adding 10 kg of methyl ethyl ketone to 1 kg of refined corn oil and stirring, the mixture was cooled at -70°C for 3 hours using a dry ice/methanol refrigerant. Thereafter, methyl ethyl ketone was distilled off in an evaporator from the methyl ethyl ketone solution in which the solids were removed by suction filtration to obtain a red colored liquid. Add 10 times the weight of methyl ethyl ketone to this and use the same method again to remove the low-temperature solidifying substances.The methyl ethyl ketone is then distilled off to form a red, highly viscous liquid.
Obtained 25g. Furthermore, 22 g of this substance was sequentially developed with the solvents listed in Table 1 through a glass column with an inner diameter of 70 mm packed with 1500 g of activated "Wako Gel C-200", and after collecting each section, the solvent was distilled off.
Four columns of fractionated material were obtained as shown in Table 2.

【表】【table】

【表】 ここで得られた区分を日立ゲル3053カラム
を装着した高速液体クロマトグラフイを用い、
メタノール:イソオクタン:水=500:10:20
にて溶離させ、モノリノレイン標準品の保持時
間に相当する部分を分取した。分取されたもの
は主としてリノール酸から成るモノグリセリド
であつた。分取を繰返し、7.6gの区分より
約100mgのモノリノレイン(純度95%)を得た。 (2) 動物実験 スプラグ・ドーレ系28日令雄ラツトを2日間
市販飼料で飼育後、区分けを行い、1区10匹、
平均体重98.9±2.3gのものを用い第3表に示
した試験飼料を自由摂取させ5日間飼育した。
給餌給水は蒸溜水100gに対し第2表に示した
第4区分を0.1%、モノリノレイン0.1%または
0.3%(w/w)、乳化剤(「Tween80」)を5mg
添加しワーリングブレンダーを用い5000rpmに
て5分間処理したものを使用当日に調製し自由
摂取させた。 飼育終了後16時間絶食後エーテル麻酔下で採
血し常法により血清を採取した。血清中の総コ
レステロールは和光純薬工業(株)製キツト
「cholesterol B−Test Wako」および血清β
−リポタンパクは同じく同社のキツト「β−
Lipoprotein−Test Wako」を用いそれぞれ測
定した。飼育成績および血清総コレステロール
値と血清β−リポプロテイン値第4表に示し
た。
[Table] The classification obtained here was determined using high performance liquid chromatography equipped with a Hitachi Gel 3053 column.
Methanol:isooctane:water=500:10:20
A portion corresponding to the retention time of the monolinolein standard product was collected. What was collected was monoglyceride mainly consisting of linoleic acid. The fractionation was repeated and about 100 mg of monolinolein (purity 95%) was obtained from the 7.6 g portion. (2) Animal experiment After feeding 28-day-old Sprague-Dohle male rats on commercially available feed for 2 days, they were divided into sections, with 10 rats in each section.
The mice had an average weight of 98.9±2.3 g and were raised for 5 days with free access to the test feed shown in Table 3.
For feeding water, add 0.1% of the 4th category shown in Table 2 to 100g of distilled water, 0.1% of monolinolein, or
0.3% (w/w), 5 mg emulsifier (“Tween80”)
It was prepared on the day of use and allowed to be taken ad libitum by processing it for 5 minutes at 5000 rpm using a Waring blender. After the end of rearing, blood was collected under ether anesthesia after fasting for 16 hours, and serum was collected using a conventional method. Total cholesterol in serum was measured using the kit “cholesterol B-Test Wako” manufactured by Wako Pure Chemical Industries, Ltd. and serum β.
- Lipoprotein is also produced by the company's Kittu ``β-
Each was measured using "Lipoprotein-Test Wako". The breeding results and serum total cholesterol and serum β-lipoprotein values are shown in Table 4.

【表】【table】

【表】 〓
%にする。
チヨコラD滴 0.01%〓
[Table] 〓
Make it %.
Chiyokora D drops 0.01%

【表】 以上の結果から、モノリノレインの添加による
平均増体量、平均食下量および飼料効率には全く
影響を及ぼさず、剖検所見も対照区と差異は認め
なかつた。血清総コレステロール値および血清β
−リポプロテイン値にモノリノレインの有意の効
果が認められた。 実施例 2 市販のリンゴジユース(全農(製))にモノリ
ノレインを0.2%添加して果汁を得た。 このリンゴジユースは実施例1の飲料同様の血
中コレステロールの低下または上昇抑制作用を有
していた。 実施例 3 下記配合の各原料を1000部の無菌水に溶かして
200ml容器に詰け栄養飲料とした。 糖 類 150部 混合アミノ酸 5部 エタノール 15部 モノリノレイン 3部酢酸トコフエロール 1部 この栄養飲料は実施例1の飲料同様の血中コレ
ステロールの低下または上昇抑制作用を有してい
た。 実施例 4 砂糖を溶解して糖液をつくり、これに酸味料、
香料およびその他の原料を加えて調合しシラツプ
を作り、シラツプに対し0.2%モノリノレインを
加えた。これを200mlビンに詰めた後、炭酸ガス
を圧入した水を充たして打栓し炭酸飲料とした。 実施例 5 脱皮大豆2Kgを粉砕後、10倍量の沸とう水を加
え、デイスパーズミルで分散し、さらにパイプラ
イン中で直接水蒸気と接触せしめて急激に120℃
にて30秒間加熱した。これを遠心分離してオカラ
を除去し豆乳を得た。この豆乳にモノリノレイン
0.5%を加えて分散させた。 この豆乳は実施例1の飲料同様の血中コレステ
ロールの低下または上昇抑制作用を有していた。
[Table] From the above results, the addition of monolinolein had no effect on average weight gain, average food consumption, or feed efficiency, and no difference was observed in the autopsy findings from the control group. Serum total cholesterol level and serum β
-A significant effect of monolinolein on lipoprotein levels was observed. Example 2 Fruit juice was obtained by adding 0.2% monolinolein to commercially available apple juice (manufactured by Zennoh Co., Ltd.). This apple juice had the same effect of lowering or suppressing the increase in blood cholesterol as the drink of Example 1. Example 3 Dissolve each ingredient in the following formulation in 1000 parts of sterile water.
It was packed into a 200ml container and used as a nutritional drink. Sugars 150 parts Mixed amino acids 5 parts Ethanol 15 parts Monolinolein 3 parts Tocopherol acetate 1 part This nutritional drink had the same effect of lowering or suppressing the rise of blood cholesterol as the drink of Example 1. Example 4 Dissolve sugar to make a sugar solution, add acidulant,
A syrup was prepared by adding fragrance and other raw materials, and 0.2% monolinolein was added to the syrup. This was packed into 200ml bottles, filled with water injected with carbon dioxide gas, and capped to produce a carbonated drink. Example 5 After pulverizing 2 kg of dehulled soybeans, 10 times the amount of boiling water was added, dispersed in a dispersion mill, and then brought into direct contact with steam in a pipeline to be rapidly heated to 120°C.
and heated for 30 seconds. This was centrifuged to remove okara to obtain soy milk. Monolinolein in this soy milk
0.5% was added and dispersed. This soymilk had the same effect of lowering or suppressing the increase in blood cholesterol as the drink of Example 1.

Claims (1)

【特許請求の範囲】 1 飲料中に、モノリノレインを0.1重量%ない
し30重量%含有せしめた飲料。 2 モノリノレインが、β−モノリノレインであ
る特許請求の範囲第1項記載の飲料。
[Claims] 1. A beverage containing 0.1% to 30% by weight of monolinolein. 2. The beverage according to claim 1, wherein the monolinolein is β-monolinolein.
JP58151351A 1982-09-20 1983-08-19 Drink Granted JPS6043368A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP58151351A JPS6043368A (en) 1983-08-19 1983-08-19 Drink
EP83305367A EP0104043A3 (en) 1982-09-20 1983-09-14 Foodstuffs and pharmaceuticals

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP58151351A JPS6043368A (en) 1983-08-19 1983-08-19 Drink

Publications (2)

Publication Number Publication Date
JPS6043368A JPS6043368A (en) 1985-03-07
JPH0260306B2 true JPH0260306B2 (en) 1990-12-14

Family

ID=15516654

Family Applications (1)

Application Number Title Priority Date Filing Date
JP58151351A Granted JPS6043368A (en) 1982-09-20 1983-08-19 Drink

Country Status (1)

Country Link
JP (1) JPS6043368A (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1303771C (en) * 1986-02-25 1992-06-16 Jerold C. Rosenfeld Preparation of gray to blue aromatic polyesters by incorporation of cobalt into the catalyst system
JP2009155257A (en) * 2007-12-26 2009-07-16 Taiyo Corp Antibacterial agent and oral composition, food and drink containing the same

Also Published As

Publication number Publication date
JPS6043368A (en) 1985-03-07

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