JP2008247768A - Active oxygen scavenger and use method thereof - Google Patents
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Abstract
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本発明は、アルキルグリコシドを含有することを特徴とする活性酸素消去剤とその利用法に関する。詳しくは、米穀や菜種から抽出した、もしくは合成した、安全性に優れ、風味も良好な活性酸素消去剤、並びに本剤を含有する食品、医薬品に関するものである。 The present invention relates to an active oxygen scavenger characterized by containing an alkyl glycoside and a method for using the same. More specifically, the present invention relates to an active oxygen scavenger that is extracted from rice cereal or rapeseed or synthesized, is excellent in safety and has a good flavor, and foods and medicines containing this agent.
生体内活性酸素 は本来生体を守るために、殺菌および殺腫瘍物質として生成される。しかし選択毒性がないため、正常な細胞にも作用してしまうことがあり、活性酸素
の過剰は、生体に対して様々の障害を引き起こすことが知られている。一例として、活性酸素 は金属イオンの触媒の存在下にヒドロキシルラジカルを生成するが、ヒドロキシルラジカルは血中ＬＤＬの過酸化を引き起こし、更に酸化されたＬＤＬが血管内皮細胞に作用して血栓を形成する。その結果、生活習慣病と言われる高血圧症や、動脈硬化や、糖尿病のような病気になりやすくなる(非特許文献１参照)。
In vivo active oxygen is originally produced as a bactericidal and tumoricidal substance to protect the living body. However, since there is no selective toxicity, it may act on normal cells, and excess of active oxygen is known to cause various damages to the living body. As an example, active oxygen generates hydroxyl radicals in the presence of a metal ion catalyst, but hydroxyl radicals cause peroxidation of blood LDL, and the oxidized LDL acts on vascular endothelial cells to form a thrombus. . As a result, it becomes easy to develop a disease such as hypertension, arteriosclerosis, and diabetes, which are called lifestyle-related diseases (see Non-Patent Document 1).
スーパーオキシドジスムターゼ（以下、ＳＯＤ という）は、生体内に広くかつ多量に存在し、生体内における活性酸素 除去成分として重要な抗酸化系酵素である。ＳＯＤ
は活性酸素 の一種であるスーパーオキシドアニオンの不均化反応を触媒し、この反応によって細胞内のスーパーオキシドは１０万分の1に低下する（非特許文献２参照）。
体内でＳＯＤ 様作用を補強できる因子として、ＳＯＤ
そのもの又はＳＯＤ 様物質がある。ＳＯＤ は大量に、安易に入手できないため、ＳＯＤ 様作用を補強する手段のほとんどがＳＯＤ
様活性物質の摂取である。例えば、ビタミンＣ、ビタミンＥや、カテキン類の摂取が挙げられる。
Superoxide dismutase (hereinafter referred to as SOD) is an antioxidant enzyme that exists widely and in large amounts in the living body and is important as a component for removing active oxygen in the living body. SOD
Catalyzes the disproportionation reaction of superoxide anion, which is a kind of active oxygen, and this reaction reduces intracellular superoxide to 1 / 100,000 (see Non-Patent Document 2).
SOD as a factor that can reinforce SOD like action in the body
As such or SOD-like material. Since SOD is not readily available in large quantities, most of the means to reinforce SOD-like effects are SOD.
Ingestion of active substances. For example, intake of vitamin C, vitamin E and catechins can be mentioned.
しかしこれらの物質は、安定性や吸収性等の問題で、生体内での活性酸素 を除去する作用が充分でないため、より優れたＳＯＤ 様物質すなわち活性酸素消去物質の開発が望まれていた。これまでに活性酸素消去活性を示すペプチド及びペプチド混合物として、小麦グルテンの分解により得られたヘキサペプチド（特許文献５参照）、植物蛋白を酵素分解して得られるペプチド混合物（特許文献６参照）、オウゴン中のバイカレイン、バラ科植物・刺梨の果汁等に含まれている活性酸素消去物質（特開昭６４−５０８７７号，特開平３−８３５４８号等）等が報告されている。 However, these substances are not stable enough to remove active oxygen in the living body due to problems such as stability and absorbability. Therefore, development of a better SOD-like substance, that is, an active oxygen scavenging substance has been desired. Peptides and peptide mixtures that exhibit active oxygen scavenging activity so far include hexapeptides obtained by the decomposition of wheat gluten (see Patent Document 5), peptide mixtures obtained by enzymatic degradation of plant proteins (see Patent Document 6), Active oxygen-eliminating substances (JP-A-64-50877, JP-A-3-83548, etc.) contained in baicalein, rosaceae and prickly pear juice in Ogon have been reported.
こうして、活性酸素消去物質は病気の予防因子や美容因子として特定保健用食品や健康食品等に利用されてきた。しかし、従来の活性酸素消去物質は、効果が十分でなかったり毒性を有すため利用範囲が限られていた。 Thus, active oxygen scavengers have been used in specific health foods and health foods as disease prevention factors and beauty factors. However, conventional active oxygen scavenging substances have a limited range of use because they are not sufficiently effective or toxic.
一方、アルキルグリコシド (alkylglycoside) は糖と高級アルコールがグリコシド結合した物質であり、非イオン性界面活性剤 (Non-ion
surfactant) として利用されてきた（特許文献９）。また、糖が結合したフラボノイドの活性酸素消去作用が知られていた（特許文献１０）。しかし、アルキルグリコシドの活性酸素消去作用に関しては知られていなかった。
On the other hand, alkylglycoside is a substance in which sugar and higher alcohol are glycosidically bonded, and is a non-ionic surfactant (Non-ion
(Patent Document 9). In addition, the active oxygen scavenging action of flavonoids to which sugar is bound has been known (Patent Document 10). However, the active oxygen scavenging action of alkyl glycosides has not been known.
本発明は上記課題を解決するものであり、安全性の極めて高く、風味良好で無色無臭な活性酸素消去剤並びに本剤を含有する活性酸素消去用食品、ならびに医薬品を提供することを目的とする。 The present invention has been made to solve the above-mentioned problems, and an object thereof is to provide an active oxygen scavenger that is extremely safe, has a good flavor and is colorless and odorless, a food for active oxygen scavenger containing the agent, and a pharmaceutical product. .
本発明者らは上記の現状に鑑み、鋭意検討の結果、米穀や菜種から酵素処理、抽出等または、化学合成により得られるアルキルグリコシドが活性酸素消去作用を有することを見出し、本発明を完成するに至った。 As a result of intensive studies, the present inventors have found that alkyl glycosides obtained by enzyme treatment, extraction, etc. from rice cereal and rapeseed or chemical synthesis have an active oxygen scavenging action, and complete the present invention. It came to.
即ち、本発明は、次の［１］〜［４］である。
［１］アルキルグリコシドを含有することを特徴とする活性酸素消去剤。
［２］アルキルグリコシドがメチルグリコシド、エチルグリコシド、プロピルグリコシド、ブチルグリコシドのうちの１種または２種以上の混合物である請求項１記載の活性酸素消去剤。
［３］［１］、［２］記載の活性酸素消去剤を有効成分とする活性酸素消去用医薬組成物
［４］［１］、［２］記載の活性酸素消去剤を有効成分とする活性酸素消去用医薬組成物
That is, the present invention includes the following [1] to [4].
[1] An active oxygen scavenger containing an alkyl glycoside.
[2] The active oxygen scavenger according to claim 1, wherein the alkyl glycoside is one or a mixture of two or more of methyl glycoside, ethyl glycoside, propyl glycoside, and butyl glycoside.
[3] A pharmaceutical composition for scavenging active oxygen containing the active oxygen scavenger described in [1] or [2] as an active ingredient [4] An active comprising the active oxygen scavenger described in [1] or [2] as an active ingredient Oxygen scavenging pharmaceutical composition
すなわち、本発明は、米穀や菜種から酵素処理、抽出等または合成により得られるアルキルグリコシドを含む抽出物を含有することを特徴とする活性酸素消去剤とその利用法に関する。 That is, the present invention relates to an active oxygen scavenger characterized by containing an extract containing an alkyl glycoside obtained from rice grains or rapeseed by enzyme treatment, extraction or the like or synthesis, and a method for using the same.
本発明は、活性酸素消去作用を有すると共に、安全性の極めて高く、吸収性に優れ、風味良好で無臭であり、呈味性良好で且つ安価に得られる、アルキルグリコシドを含む活性酸素消去剤およびその利用法を提供することができる。 The present invention provides an active oxygen scavenger containing an alkylglycoside, which has an active oxygen scavenging action, is extremely safe, excellent in absorbability, good in flavor, odorless, good in taste and inexpensive. How to use it can be provided.
本発明で用いるアルキルグリコシド (alkylglycoside) とは糖とアルコールがグリコシド結合した物質であり、グリコシダーゼにより分解されないという特徴を持つ。本発明に用いるアルキルグリコシドのアルコール基としてはメチルアルコール、エチルアルコール、プロピルアルコール、ブチルアルコール等が選択できるが、安全性と効果の面で、エチルアルコールが最も適している。 The alkylglycoside used in the present invention is a substance in which sugar and alcohol are glycoside-bonded and has a characteristic that it is not decomposed by glycosidase. As the alcohol group of the alkyl glycoside used in the present invention, methyl alcohol, ethyl alcohol, propyl alcohol, butyl alcohol and the like can be selected, but ethyl alcohol is most suitable in terms of safety and effect.
本発明の用いるアルキルグリコシドを構成する糖としては、グルコース、アラビノース、キシロース、フラクトース、ガラクトース、マンノース、リボースのＤまたはＬ体を選択できるが、これら以外の、希少糖と呼ばれる糖類も選択することができる。また、複数のアルキルグリコシドの１種または２種以上の混合物を用途に合わせ利用することができる。 As the sugar constituting the alkyl glycoside used in the present invention, D or L form of glucose, arabinose, xylose, fructose, galactose, mannose, ribose can be selected, but other sugars called rare sugars can also be selected. it can. Moreover, the 1 type, or 2 or more types of mixture of the some alkyl glycoside can be utilized according to a use.
本発明に使用するアルキルグリコシドは、製造法により規定されないが、天然、特に植物や食品産業の余剰物から抽出したり、合成により得ることができる。例えば、米に含まれるエチルグリコシドを水、エタノール等の溶剤を使用して抽出し、場合によっては、イオン交換樹脂やシリカゲル等を用いた処理により、純度を高めて使用することができる。 The alkyl glycoside used in the present invention is not defined by the production method, but can be extracted from natural, particularly from the surplus of plants and food industries, or can be obtained by synthesis. For example, ethyl glycoside contained in rice can be extracted with a solvent such as water or ethanol, and in some cases, it can be used with increased purity by treatment with ion exchange resin or silica gel.
アルキルグリコシドを合成する方法の例として、位置および立体の高い選択性を達成するため、アノマー位を活性化した糖供与体と糖受容体とを無水溶媒中で反応させる化学的グリコシル化反応（非特許文献３）、または水溶液中で糖転移酵素または糖加水分解酵素を利用するグリコシル化反応（非特許文献４、５）が用いられている。また、界面活性剤を生産する単糖と長鎖脂肪族アルコールとのグリコシル化では、工業的に大量に製造する必要がある一方で高度な選択性を必ずしも必要としないことから、トシル酸などの触媒存在下、無溶媒で加熱する手法がしばしば用いられている（特許文献１１、１２）。さらに、すでに市場で販売されているアルキルグリコシドを利用することも可能である。 As an example of a method for synthesizing alkyl glycosides, a chemical glycosylation reaction (non-reaction) in which an anomer-activated sugar donor and a sugar acceptor are reacted in an anhydrous solvent to achieve high positional and steric selectivity. Patent Document 3) or a glycosylation reaction using a glycosyltransferase or a sugar hydrolase in an aqueous solution (Non-Patent Documents 4 and 5) is used. In addition, glycosylation of monosaccharides that produce surfactants and long-chain aliphatic alcohols requires industrial production in large quantities, but does not necessarily require a high degree of selectivity. A technique of heating without a solvent in the presence of a catalyst is often used (Patent Documents 11 and 12). Furthermore, it is also possible to use alkyl glycosides already marketed.
本発明の活性酸素消去剤は、上記のアルキルグリコシドを０．０１から９０％、好ましくは０．１から５０％、より好ましくは１から３０％含有する。アルキルグリコシドルの含有量が０．０１％未満では活性酸素消去効果が認められない。また、アルキルグリコシド含有量を９０％より多くしても、効果の顕著な増加は認められない。 The active oxygen scavenger of the present invention contains 0.01 to 90%, preferably 0.1 to 50%, more preferably 1 to 30% of the above alkyl glycoside. When the content of the alkylglycosidol is less than 0.01%, the active oxygen scavenging effect is not recognized. Further, even if the alkylglycoside content is more than 90%, no significant increase in the effect is observed.
次に、本発明の活性酸素消去剤を配合してなる医薬用組成物および食用組成物について説明する。本発明の活性酸素消去剤を配合してなる製剤は、これをそのまま、あるいは慣用の医薬製剤担体とともに医薬用組成物となし、動物およびヒトに投与することができる。医薬用組成物の剤形としては特に制限されるものではなく、必要に応じて適宜に選択すればよいが、例えば、錠剤、カプセル剤、顆粒剤、細粒剤、散剤等の経口剤、注射剤、坐剤等の非経口剤があげられる。 Next, a pharmaceutical composition and an edible composition comprising the active oxygen scavenger of the present invention will be described. A preparation comprising the active oxygen scavenger of the present invention can be administered to animals and humans as it is or as a pharmaceutical composition together with a conventional pharmaceutical preparation carrier. The dosage form of the pharmaceutical composition is not particularly limited, and may be appropriately selected according to need. For example, tablets, capsules, granules, fine granules, powders and other oral preparations, injections And parenterals such as suppositories and suppositories.
本発明において錠剤、カプセル剤、顆粒剤、細粒剤、散剤としての経口剤は、例えば、デンプン、乳糖、白糖、マンニット、カルボキシメチルセルロース、コーンスターチ、無機塩類等を用いて常法に従って製造される。これらの製剤中の本発明の活性酸素消去剤の配合量は０．０１から５０％、好ましくは０．１から３０％、より好ましくは１から１０％含有する。活性酸素消去剤の含有量が０．０１％未満では活性酸素消去効果が認められない。また。活性酸素消去剤の含有量が５０％より多くしても、効果の顕著な増加は認められない。この種の製剤には本発明の活性酸素消去剤の他に、結合剤、崩壊剤、界面活性剤、滑沢剤、流動性促進剤、矯味剤、着色剤、香料等を適宜に使用することができる。 In the present invention, oral preparations such as tablets, capsules, granules, fine granules, and powders are produced according to conventional methods using, for example, starch, lactose, sucrose, mannitol, carboxymethylcellulose, corn starch, inorganic salts, and the like. . The compounding amount of the active oxygen scavenger of the present invention in these preparations is 0.01 to 50%, preferably 0.1 to 30%, more preferably 1 to 10%. When the content of the active oxygen scavenger is less than 0.01%, the active oxygen scavenging effect is not recognized. Also. Even if the content of the active oxygen scavenger is more than 50%, no significant increase in the effect is observed. In addition to the active oxygen scavenger of the present invention, a binder, a disintegrant, a surfactant, a lubricant, a fluidity promoter, a corrigent, a colorant, a fragrance and the like are appropriately used for this type of preparation. Can do.
上記の活性酸素消去剤を含有する医薬用組成物は懸濁液、エマルション剤、シロップ剤、エリキシル剤としても投与することができ、これらの各種剤形には、矯味矯臭剤、着色剤を含有させてもよい。 The pharmaceutical composition containing the above active oxygen scavenger can be administered as a suspension, emulsion, syrup, or elixir, and these various dosage forms contain a flavoring agent and a coloring agent. You may let them.
本発明の活性酸素消去剤は食用組成物としても利用可能である。すなわち、前述のようにして得られるアルキルグリコシドを有効成分としてなる活性酸素消去食品は、これをそのまま液状、ゲル状あるいは固形状の食品、例えばジュース、清涼飲料、茶、スープ、豆乳、サラダ油、ドレッシング、ヨーグルト、ゼリー、プリン、ふりかけ、育児用粉乳、ケーキミックス、粉末状または液状の乳製品、パン、クッキー等に添加したり、必要に応じてデキストリン、乳糖、澱粉等の賦形剤や香料、色素等とともにペレット、錠剤、顆粒等に加工したり、またゼラチン等で被覆してカプセルに成形加工して健康食品や栄養補助食品等として利用できる。 The active oxygen scavenger of the present invention can also be used as an edible composition. That is, the active oxygen-eliminating food comprising the alkyl glycoside obtained as described above as an active ingredient is used as it is in a liquid, gel or solid food such as juice, soft drink, tea, soup, soy milk, salad oil, dressing. , Yogurt, jelly, pudding, sprinkles, infant formula, cake mix, powdered or liquid dairy products, bread, cookies, etc., and if necessary excipients and flavorings such as dextrin, lactose, starch, It can be processed into pellets, tablets, granules, etc. together with pigments, etc., or coated with gelatin and formed into capsules for use as health foods, nutritional supplements, etc.
これらの食品類あるいは食用組成物における本発明の活性酸素消去剤の配合量は、当該食品や組成物の種類や状態等により一律に規定しがたいが、約０．０１〜５０重量％、より好ましくは０．１〜３０重量％である。配合量が０．０１重量％未満では経口摂取による所望の効果が小さく、５０重量％を超えると食品の種類によっては風味を損なったり、当該食品を調製できなくなる場合がある。なお、本発明の活性酸素消去剤は、原料が食品であり、これをそのまま食用に供してもさしつかえない。 The compounding amount of the active oxygen scavenger of the present invention in these foods or edible compositions is difficult to define uniformly depending on the type and state of the food or composition, but is about 0.01 to 50% by weight, more Preferably it is 0.1 to 30 weight%. If the blending amount is less than 0.01% by weight, the desired effect by oral ingestion is small, and if it exceeds 50% by weight, depending on the type of food, the flavor may be impaired or the food may not be prepared. In addition, the active oxygen scavenger of this invention is a foodstuff, and can use this as it is for food.
本発明の医薬用組成物および食用組成物は、活性酸素の消去をねらいとして利用するものであれば、それを使用する上で何ら制限を受けることなく適用される。 If the pharmaceutical composition and edible composition of the present invention are used for the purpose of eliminating active oxygen, they are applied without any limitation on the use thereof.
次に、本発明を実験例、実施例、比較例にてさらに詳しく説明する。 Next, the present invention will be described in more detail with reference to experimental examples, examples and comparative examples.
＜実験例１＞活性酸素消去能の測定：木村らのヒポキサンチン−キサンチンオキシダ−ゼによるス−パ−オキシド発生系とウミホタルルシフェリン誘導体(ＭＣＬＡ)を用いた化学発光法で行った（Kimura, H., Nakano, M., 1988. Highly
sensitive and reliable chemiluminescence method for the assay of superoxide
dismutase in human erythrocytes. Febs Letters, 239 2 347-350.）。ス−パ−オキシド消去能(superoxide scavenging activity 以下「ＳＯＳＡ」と略す)は次の式で算出し、ＳＯＳＡ(％)と表示した。SOSA(％)＝発光阻害率(％)＝(I0-Ii)/I0×100。ここで I0 は対照発光量、 Ii はサンプル発光量である。
<Experimental Example 1> Measurement of active oxygen scavenging ability: It was carried out by a chemiluminescence method using Kimura et al.'S hypoxanthine-xanthine oxidase superoxide generation system and Cypridina luciferin derivative (MCLA). ., Nakano, M., 1988. Highly
sensitive and reliable chemiluminescence method for the assay of superoxide
dismutase in human erythrocytes. Febs Letters, 239 2 347-350.). The superoxide scavenging activity (hereinafter abbreviated as “SOSA”) was calculated by the following formula and expressed as SOSA (%). SOSA (%) = luminescence inhibition rate (%) = (I 0 -I i ) / I 0 × 100. Here, I 0 is the control light emission amount, and I i is the sample light emission amount.
＜実験例２＞酒粕からのアルキルグリコシドの調製：麹米として山田錦(精白歩合60％)、掛米として美山錦(精白歩合60％)を用いた本醸造酒製造時に生成された酒粕を試料とした。酒粕１０００ｇを真空凍結乾燥後、エタノール５０００ｍｌを加え、室温で２４時間抽出を行った。抽出後不溶物を濾別し、上清をロータリーエバポレーターで乾燥し、粗抽出物２８．９ｇを得た。粗抽出物１０ｇをシリカゲル（ワコーゲルＣ１００：和光純薬）を充填したオープンカラム（内径５０ｍｍ、長さ５００ｍｍ）にチャージした。ヘキサン：酢酸エチルの割合が１００：０、９０：１０、８０：２０、７０：３０、６０：４０、５０：５０の溶離液をそれぞれ３００ｍｌ流し、それぞれの溶離液中の不揮発分をロータリーエバポレーターを用いて回収した。それぞれの溶離液中の不揮発分中のアルキルグリコシドを高速液体クロマトグラフィー（カラム：GL Science製ODS-3V(4.6φ×250mm)、移動相：メタノ−ル：酢酸(99:1)、流 量:1.0ml/min、検出器:（株）島津製作所製蒸発光散乱検出器）で分析した結果、ヘキサン：酢酸エチルの割合が６０：４０の溶離液中の不揮発分中に最も多くのアルキルグリコシドが検出された。ヘキサン：酢酸エチルの割合が６０：４０の溶離液中の不揮発分を精製アルキルグリコシドとした。 <Experimental example 2> Preparation of alkylglycoside from sake lees: Sake lees produced during the production of this brewed sake using Yamada Nishiki (60% pure white) as rice and Miyama Nishiki (60% pure white) as the rice It was. After 1000 g of sake lees were lyophilized under vacuum, 5000 ml of ethanol was added and extraction was performed at room temperature for 24 hours. After extraction, insoluble matters were filtered off, and the supernatant was dried on a rotary evaporator to obtain 28.9 g of a crude extract. 10 g of the crude extract was charged into an open column (inner diameter: 50 mm, length: 500 mm) packed with silica gel (Wakogel C100: Wako Pure Chemical Industries). Flow 300 ml each of eluents with hexane: ethyl acetate ratio of 100: 0, 90:10, 80:20, 70:30, 60:40, 50:50, and remove the non-volatile content in each eluent using a rotary evaporator. Used to recover. The alkyl glycoside in the non-volatile content in each eluent was subjected to high performance liquid chromatography (column: ODS-3V (4.6φ × 250 mm) manufactured by GL Science, mobile phase: methanol: acetic acid (99: 1), flow rate: 1.0 ml / min, detector: evaporative light scattering detector manufactured by Shimadzu Corporation). As a result, the largest amount of alkylglycoside was found in the non-volatile matter in the eluent having a hexane: ethyl acetate ratio of 60:40. was detected. The non-volatile content in the eluent having a hexane: ethyl acetate ratio of 60:40 was defined as a purified alkyl glycoside.
エチルグルコシド（和光純薬工業製）、実験例２の精製アルキルグリコシドの活性酸素消去能を実験例１の方法で測定した結果を表１に示した。 The results of measuring the active oxygen scavenging ability of ethyl glucoside (manufactured by Wako Pure Chemical Industries, Ltd.) and the purified alkyl glycoside of Experimental Example 2 by the method of Experimental Example 1 are shown in Table 1.
ビタミンＣ（和光純薬）、αトコフェロール（エーザイ）や、（−）エピガロカテキン緑茶由来（和光純薬）の活性酸素消去能を実験例１の方法で測定した結果を表１に併せて示した。 Table 1 also shows the results of measuring the active oxygen scavenging ability of vitamin C (Wako Pure Chemical Industries), α-tocopherol (Eisai) and (-) epigallocatechin green tea (Wako Pure Chemical Industries) by the method of Experimental Example 1. It was.
表１に示した結果から、本発明の活性酸素消去剤が先行技術と比較して優れた活性酸素消去作用を有していることがわかる。 From the results shown in Table 1, it can be seen that the active oxygen scavenger of the present invention has an excellent active oxygen scavenging action as compared with the prior art.
本発明は人以外に、家畜、ペットなどの動物用として使用できる。 In addition to humans, the present invention can be used for animals such as livestock and pets.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO1986006417A1 (en) * | 1985-04-26 | 1986-11-06 | A. E. Staley Manufacturing Company | Method for inhibiting oxidation or acid attack of ferrous metals utilizing glycosides and cleaning compositions for ferrous metals |
| JP2002119248A (en) * | 2000-10-12 | 2002-04-23 | Ozeki Corp | Obesity inhibitory composition |
| JP2005130710A (en) * | 2003-10-28 | 2005-05-26 | Kanebo Cosmetics Inc | Skin-beautifying food-and-drink composition |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO1986006417A1 (en) * | 1985-04-26 | 1986-11-06 | A. E. Staley Manufacturing Company | Method for inhibiting oxidation or acid attack of ferrous metals utilizing glycosides and cleaning compositions for ferrous metals |
| JP2002119248A (en) * | 2000-10-12 | 2002-04-23 | Ozeki Corp | Obesity inhibitory composition |
| JP2005130710A (en) * | 2003-10-28 | 2005-05-26 | Kanebo Cosmetics Inc | Skin-beautifying food-and-drink composition |
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