JP2003221339A - Anti-inflammatory agent - Google Patents
Anti-inflammatory agentInfo
- Publication number
- JP2003221339A JP2003221339A JP2002019378A JP2002019378A JP2003221339A JP 2003221339 A JP2003221339 A JP 2003221339A JP 2002019378 A JP2002019378 A JP 2002019378A JP 2002019378 A JP2002019378 A JP 2002019378A JP 2003221339 A JP2003221339 A JP 2003221339A
- Authority
- JP
- Japan
- Prior art keywords
- xylooligosaccharide
- acidic
- acid
- inflammatory agent
- polymerization
- 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
Links
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、医薬品、医薬部外
品、化粧品分野に属する新規な抗炎症剤に関する。より
詳細には、優れた薬理活性を有し、しかも安全性の高い
抗炎症剤に関する。TECHNICAL FIELD The present invention relates to a novel anti-inflammatory agent belonging to the fields of medicines, quasi drugs and cosmetics. More specifically, it relates to an anti-inflammatory agent having excellent pharmacological activity and high safety.
【０００２】[0002]
【従来の技術】本来、炎症は生体防御反応の一つである
が、それが過度となると痛み、かゆみ、発熱を伴う為、
古くから抗炎症剤には高い需要があった。ヤナギの樹皮
には抗炎症作用があることが知られていたが、この活性
本体はサリシンという配糖体であり、体内でサリチル酸
に変化して活性を発揮する。現在では合成品であるイン
ドメタシンが代表的な抗炎症剤として使用されている。
サリチル酸やインドメタシンは非ステロイド系抗炎症剤
と呼ばれており、それらのメカニズムはプロスタグラン
ジン類の合成阻害である為、低濃度で高い活性を示す。
しかしながら、プロスタグランジン類には胃酸分泌抑
制、胃粘膜保護作用等もある為、胃潰瘍や長期服用によ
る腎障害等の副作用が懸念されている。2. Description of the Related Art Originally, inflammation is one of the biological defense reactions, but if it becomes excessive, it causes pain, itch, and fever.
There has been a high demand for anti-inflammatory agents since ancient times. It was known that the bark of willow has an anti-inflammatory effect, but the active substance is a glycoside called salicin, which changes its activity to salicylic acid in the body and exerts its activity. Currently, synthetic indomethacin is used as a typical anti-inflammatory agent.
Salicylic acid and indomethacin are called non-steroidal anti-inflammatory agents, and their mechanism is inhibition of the synthesis of prostaglandins, so they show high activity at low concentrations.
However, since prostaglandins also suppress gastric acid secretion, protect gastric mucosa, etc., side effects such as gastric ulcer and renal damage due to long-term administration are feared.
【０００３】ステロイド系抗炎症剤としては、副腎皮質
ホルモンであるヒドロコルチゾン、プレドニゾロン、ト
リアムシノロン等があるが、これらの薬剤もアラキドン
酸カスケードの上流部分を阻害するのみで、非ステロイ
ド剤と同様の副作用を持つばかりか、副腎皮質機能障害
や免疫抑制作用による感染症の恐れもある。The steroidal anti-inflammatory drugs include adrenocortical hormones such as hydrocortisone, prednisolone, and triamcinolone. These drugs only inhibit the upstream part of the arachidonic acid cascade and have the same side effects as nonsteroidal drugs. In addition to having it, there is also a risk of infection due to adrenocortical dysfunction or immunosuppressive action.
【０００４】一方、天然物からの抗炎症作用を有する物
質の探索も行われており、キク科ヨモギ属の多糖類（特
開平6-211679号公報）、キトサンの誘導体（特開平5-17
8876号公報）、2〜6糖のオリゴ糖に脂質が結合したもの
（特開平8-283285号公報）、ヒャクジツセイ等の抽出物
（特開2001-226273号公報）が提案されている。しかし
ながら、効果と経済性に問題があり、現在の薬剤に取っ
て代わるだけの薬剤は見出されていないのが現状であ
る。On the other hand, a search for substances having an anti-inflammatory effect from natural products has also been carried out, and polysaccharides of the genus Artemisia of the Asteraceae family (JP-A-6-211679) and derivatives of chitosan (JP-A-5-17).
8876), oligosaccharides of 2 to 6 sugars to which a lipid is bound (Japanese Patent Laid-Open No. 8-283285), and extracts such as Chinese radish (Japanese Patent Laid-Open No. 2001-226273). However, there is a problem in effectiveness and economical efficiency, and it is the current situation that no drug that can replace the current drug has been found.
【０００５】なお、酸性キシロオリゴ糖の生理効果に関
しては、水耕栽培に於けるスギ挿穂の発根促進効果の記
載（セルラーゼ研究会報第16巻2001年）があるのみで、
抗炎症作用に関する開示はなされていない。Regarding the physiological effects of acidic xylooligosaccharides, there is only a description of the rooting promotion effect of cedar cuttings in hydroponics (Cellulase Research Bulletin Vol. 16 2001).
There is no disclosure regarding anti-inflammatory effects.
【０００６】[0006]
【発明が解決しようとする課題】本発明に於いては、薬
理活性が高く、天然物を原料とし、副作用が無く、安全
性の高い抗炎症剤を得ることを目的とした。DISCLOSURE OF THE INVENTION The object of the present invention is to obtain an anti-inflammatory agent having a high pharmacological activity, a natural product as a raw material, no side effects and a high safety.
【０００７】[0007]
【課題を解決するための手段】前記課題を解決する為、
マウス耳浮腫抑制を指標として抗炎症剤のスクリーニン
グを行った。その結果、ウロン酸残基が付加した酸性キ
シロオリゴ糖組成物が優れた抗炎症効果を有することを
見出し、安全性も優れることより、本発明を完成するに
至った。[Means for Solving the Problems] In order to solve the above problems,
The anti-inflammatory drug was screened using the mouse ear edema inhibition as an index. As a result, they have found that the acidic xylooligosaccharide composition to which a uronic acid residue is added has an excellent anti-inflammatory effect, and have completed the present invention by having excellent safety.
【０００８】本発明は以下の構成を採用する。即ち、本
発明の第１は、「キシロオリゴ糖分子中にウロン酸残基
を有する酸性キシロオリゴ糖を有効成分とする抗炎症
剤」である。The present invention employs the following configurations. That is, the first aspect of the present invention is "an anti-inflammatory agent containing an acidic xylooligosaccharide having an uronic acid residue in a xylooligosaccharide molecule as an active ingredient".
【０００９】本発明の第２は、前記第１発明において、
該酸性キシロオリゴ糖はキシロースの重合度が異なるオ
リゴ糖の混合組成物であり、平均重合度が2.0〜11.0で
あることを特徴とする抗炎症剤である。A second aspect of the present invention is the same as the first aspect.
The acidic xylooligosaccharide is a mixed composition of oligosaccharides having different degrees of polymerization of xylose, and is an anti-inflammatory agent characterized by having an average degree of polymerization of 2.0 to 11.0.
【００１０】本発明の第３は、前記第１または第２の発
明において、前記酸性キシロオリゴ糖が、「リグノセル
ロース材料を酵素的及び／又は物理化学的に処理してキ
シロオリゴ糖成分とリグニン成分の複合体を得、次いで
該複合体を酸加水分解処理してキシロオリゴ糖混合物を
得、得られるキシロオリゴ糖混合物から、１分子中に少
なくとも１つ以上のウロン酸残基を側鎖として有するキ
シロオリゴ糖を分離して得たもの」であることを特徴と
する抗炎症剤である。In a third aspect of the present invention, in the first or second aspect of the present invention, the acidic xylooligosaccharide has a characteristic that "a lignocellulosic material is enzymatically and / or physicochemically treated to form a xylooligosaccharide component and a lignin component. A complex is obtained, and then the complex is subjected to acid hydrolysis treatment to obtain a xylooligosaccharide mixture. From the resulting xylooligosaccharide mixture, a xylooligosaccharide having at least one uronic acid residue as a side chain in one molecule is obtained. It is an anti-inflammatory agent characterized by being "obtained by separation".
【００１１】本発明の第４は、前記第１〜第３の発明に
おいて、ウロン酸がグルクロン酸もしくは4-O-メチル−
グルクロン酸であることを特徴とする抗炎症剤である。A fourth aspect of the present invention is the same as the first to third aspects, wherein the uronic acid is glucuronic acid or 4-O-methyl-
It is an anti-inflammatory agent characterized by being glucuronic acid.
【００１２】[0012]
【発明の実施の形態】以下、本発明の構成について詳述
する。キシロオリゴ糖とは、キシロースの2量体である
キシロビオース、3量体であるキシロトリオース、ある
いは4量体〜20量体程度のキシロースの重合体を言う。
本発明で使用する酸性キシロオリゴ糖とは、キシロオリ
ゴ糖１分子中に少なくとも１つ以上のウロン酸残基を有
するものを言う。また、キシロースの重合度が異なるオ
リゴ糖の混合組成物であっても良い。一般的には、天然
物から製造するために、このような組成物として得られ
ることが多く、以下、主として酸性キシロオリゴ糖組成
物について説明する。該組成物は、平均重合度で示す数
値は正規分布をとる酸性キシロオリゴ糖のキシロース鎖
長の平均値で、2.0〜15.0が好ましく、2.0〜11.0がより
好ましい。キシロース鎖長の上限と下限との差は20以下
が好ましく、10以下がより好ましい。ウロン酸は天然で
は、ペクチン、ペクチン酸、アルギン酸、ヒアルロン
酸、ヘパリン、コンドロイチン硫酸、デルタマン硫酸等
の種々の生理活性を持つ多糖の構成成分として知られて
いる。本発明におけるウロン酸としては特に限定されな
いが、グルクロン酸もしくは4-O-メチル−グルクロン酸
が好ましい。BEST MODE FOR CARRYING OUT THE INVENTION The constitution of the present invention will be described in detail below. The xylooligosaccharide refers to xylobiose, which is a dimer of xylose, xylotriose, which is a trimer, or a polymer of xylose of about a tetramer to a 20mer.
The acidic xylooligosaccharide used in the present invention is one having at least one uronic acid residue in one molecule of xylooligosaccharide. Further, it may be a mixed composition of oligosaccharides having different degrees of polymerization of xylose. In general, since it is produced from a natural product, it is often obtained as such a composition, and the acidic xylooligosaccharide composition will be mainly described below. In the composition, the numerical value represented by the average degree of polymerization is an average value of the xylose chain length of acidic xylooligosaccharides having a normal distribution, preferably 2.0 to 15.0, and more preferably 2.0 to 11.0. The difference between the upper limit and the lower limit of the xylose chain length is preferably 20 or less, more preferably 10 or less. Uronic acid is naturally known as a constituent component of polysaccharides having various physiological activities such as pectin, pectic acid, alginic acid, hyaluronic acid, heparin, chondroitin sulfate, and deltaman sulfate. The uronic acid in the present invention is not particularly limited, but glucuronic acid or 4-O-methyl-glucuronic acid is preferable.
【００１３】上記のような酸性キシロオリゴ糖組成物を
得ることが出来れば、その製法は特に限定されないが、
（１）木材からキシランを抽出し、それを酵素的に分解
する方法（セルラーゼ研究会発行、セルラーゼ研究会報
第16巻、2001年6月14日発行、P17-26）と、（２）リグ
ノセルロース材料を酵素的及び／又は物理化学的に処理
してキシロオリゴ糖成分とリグニン成分の複合体を得、
次いで該複合体を酸加水分解処理してキシロオリゴ糖混
合物を得、得られるキシロオリゴ糖混合物から、１分子
中に少なくとも１つ以上のウロン酸残基を側鎖として有
するキシロオリゴ糖を分離する方法が挙げられる。特
に、（２）の方法が5〜10量体のように比較的高い重合
度のものを大量に安価に製造することが可能である点で
好ましく、以下にその概要を示す。If the acidic xylooligosaccharide composition as described above can be obtained, the production method is not particularly limited,
(1) A method for extracting xylan from wood and enzymatically decomposing it (Cellulase Research Group, Cellulase Research Bulletin Volume 16, June 14, 2001, P17-26), and (2) Lignocellulose. Enzymatically and / or physicochemically treating the material to obtain a complex of xylooligosaccharide component and lignin component,
Then, the complex is subjected to acid hydrolysis treatment to obtain a xylooligosaccharide mixture, and a xylooligosaccharide having at least one or more uronic acid residues in one molecule as a side chain is separated from the resulting xylooligosaccharide mixture. To be Particularly, the method (2) is preferable in that it is possible to inexpensively produce a large amount of a polymer having a relatively high degree of polymerization such as a 5- to 10-mer, and the outline thereof is shown below.
【００１４】酸性オリゴ糖組成物は、化学パルプ由来の
リグノセルロース材料を原料とし、加水分解工程、濃縮
工程、希酸処理工程、精製工程を経て得ることができ
る。加水分解工程では、希酸処理、高温高圧の水蒸気
（蒸煮・爆砕）処理もしくは、ヘミセルラーゼによって
リグノセルロース中のキシランを選択的に加水分解し、
キシロオリゴ糖とリグニンからなる高分子量の複合体を
中間体として得る。濃縮工程では逆浸透膜等により、キ
シロオリゴ糖−リグニン様物質複合体が濃縮され、低重
合度のオリゴ糖や低分子の夾雑物などを除去することが
できる。濃縮工程は逆浸透膜を用いることが好ましい
が、限外濾過膜、塩析、透析などでも可能である。得ら
れた濃縮液の希酸処理工程により、複合体からリグニン
様物質が遊離し、酸性キシロオリゴ糖と中性キシロオリ
ゴ糖を含む希酸処理液を得ることができる。この時、複
合体から切り離されたリグニン様物質は酸性下で縮合し
沈殿するのでセラミックフィルターや濾紙などを用いた
ろ過等により除去することができる。希酸処理工程で
は、酸による加水分解を用いることが好ましいが、リグ
ニン分解酵素などを用いた酵素分解などでも可能であ
る。The acidic oligosaccharide composition can be obtained by using a lignocellulosic material derived from chemical pulp as a raw material, through a hydrolysis step, a concentration step, a dilute acid treatment step, and a purification step. In the hydrolysis process, dilanic acid treatment, high-temperature and high-pressure steam (steaming / explosion) treatment, or xylan in lignocellulose is selectively hydrolyzed by hemicellulase,
A high molecular weight complex of xylooligosaccharide and lignin is obtained as an intermediate. In the concentration step, the xylooligosaccharide-lignin-like substance complex is concentrated by a reverse osmosis membrane or the like, and oligosaccharides having a low degree of polymerization and low molecular contaminants can be removed. It is preferable to use a reverse osmosis membrane in the concentration step, but it is also possible to use an ultrafiltration membrane, salting out, dialysis and the like. A lignin-like substance is released from the complex by a dilute acid treatment step of the obtained concentrated liquid, and a dilute acid treatment liquid containing acidic xylooligosaccharide and neutral xylooligosaccharide can be obtained. At this time, since the lignin-like substance separated from the complex condenses and precipitates under acidic conditions, it can be removed by filtration using a ceramic filter or filter paper. In the dilute acid treatment step, it is preferable to use acid hydrolysis, but enzymatic decomposition using a lignin-degrading enzyme or the like is also possible.
【００１５】精製工程は、限外濾過工程、脱色工程、吸
着工程からなる。一部のリグニン様物質は可溶性高分子
として溶液中に残存するが、限外濾過工程で除去され、
着色物質等の夾雑物は活性炭を用いた脱色工程によって
そのほとんどが取り除かれる。限外濾過工程は限外濾過
膜を用いることが好ましいが、逆浸透膜、塩析、透析な
どでも可能である。こうして得られた糖液中には酸性キ
シロオリゴ糖と中性キシロオリゴ糖が溶解している。イ
オン交換樹脂を用いた吸着工程により、この糖液から酸
性キシロオリゴ糖のみを取り出すことができる。糖液を
まず強陽イオン交換樹脂にて処理し、糖液中の金属イオ
ンを除去する。ついで強陰イオン交換樹脂を用いて糖液
中の硫酸イオンなどを除去する。この工程では、硫酸イ
オンの除去と同時に弱酸である有機酸の一部と着色成分
の除去も同時に行っている。強陰イオン交換樹脂で処理
された糖液はもう一度強陽イオン交換樹脂で処理し更に
金属イオンを除去する。最後に弱陰イオン交換樹脂で処
理し、酸性キシロオリゴ糖を樹脂に吸着させる。The purification step comprises an ultrafiltration step, a decolorization step and an adsorption step. Some lignin-like substances remain in solution as soluble polymers, but are removed by the ultrafiltration step,
Contaminants such as coloring substances are mostly removed by a decolorization process using activated carbon. It is preferable to use an ultrafiltration membrane in the ultrafiltration step, but it is also possible to use a reverse osmosis membrane, salting out, dialysis and the like. Acidic xylooligosaccharides and neutral xylooligosaccharides are dissolved in the sugar solution thus obtained. Only the acidic xylooligosaccharide can be extracted from this sugar solution by the adsorption step using an ion exchange resin. The sugar solution is first treated with a strong cation exchange resin to remove metal ions in the sugar solution. Then, sulfate ions and the like in the sugar solution are removed using a strong anion exchange resin. In this step, a part of the organic acid which is a weak acid and the coloring component are removed at the same time as the removal of sulfate ion. The sugar solution treated with the strong anion exchange resin is treated again with the strong cation exchange resin to further remove metal ions. Finally, it is treated with a weak anion exchange resin to adsorb the acidic xylooligosaccharide onto the resin.
【００１６】樹脂に吸着した酸性オリゴ糖を、低濃度の
塩（NaCl、CaCl2、KCl、MgCl2など）によって溶出させ
ることにより、夾雑物を含まない酸性キシロオリゴ糖溶
液を得ることができる。この溶液を、例えば、スプレー
ドライや凍結乾燥処理により、白色の酸性キシロオリゴ
糖組成物の粉末を得ることができる。By elution of the acidic oligosaccharide adsorbed on the resin with a low-concentration salt (NaCl, CaCl 2 , KCl, MgCl 2, etc.), an acidic xylooligosaccharide solution containing no contaminants can be obtained. This solution can be spray-dried or freeze-dried to obtain a white acidic xylooligosaccharide composition powder.
【００１７】化学パルプ由来のリグノセルロースを原料
とし、キシロオリゴ糖とリグニンからなる高分子量の複
合体を中間体とした酸性キシロオリゴ糖組成物の上記製
造法のメリットは、経済性とキシロースの平均重合度の
高い酸性キシロオリゴ糖組成物が容易に得られる点にあ
る。平均重合度は、例えば、希酸処理条件を調節する
か、再度ヘミセルラーゼで処理することによって変える
ことが可能である。また、弱陰イオン交換樹脂溶出時に
用いる溶出液の塩濃度を変化させることによって、１分
子あたりに結合するウロン酸残基の数が異なる酸性キシ
ロオリゴ糖組成物を得ることもできる。さらに、適当な
キシラナーゼ、ヘミセルラーゼを作用させることによっ
てウロン酸結合部位が末端に限定された酸性キシロオリ
ゴ糖組成物を得ることも可能である。The advantages of the above-mentioned production method of the acidic xylo-oligosaccharide composition, which uses lignocellulose derived from chemical pulp as a raw material and has a high-molecular-weight complex of xylooligosaccharide and lignin as an intermediate, is economical and the average degree of polymerization of xylose. The point is that an acidic xylo-oligosaccharide composition having a high content can be easily obtained. The average degree of polymerization can be changed by, for example, adjusting the dilute acid treatment condition or treating again with hemicellulase. Further, by changing the salt concentration of the eluate used for elution of the weak anion exchange resin, it is possible to obtain an acidic xylooligosaccharide composition in which the number of uronic acid residues bound per molecule is different. Furthermore, it is also possible to obtain an acidic xylo-oligosaccharide composition in which the uronic acid-binding site is limited to the terminal by reacting with an appropriate xylanase or hemicellulase.
【００１８】このようにして得られた酸性キシロオリゴ
糖または、酸性キシロオリゴ糖組成物は、エタノール、
プロパノール及びイソプロパノール等の低級アルコー
ル、プロピレングリコール、ジプロピレングリコール、
1,3-ブチレングリコール及びグリセリン等の多価アルコ
ール、希酸、希アルカリの水溶液等に溶解して抗炎症剤
基剤に含有させる。或いは、アルコール、エステル等を
含有する基材成分に直接添加、溶解して含有させること
もできる。また、マイクロカプセル化やリポソームに内
含させて添加してもよい。抗炎症剤に於ける酸性キシロ
オリゴ糖または、酸性キシロオリゴ糖組成物の含有量と
しては、0.001〜20.0％（以下全て質量％）の範囲で使
用することができるが、0.01〜10.0％がより好ましい。The acidic xylo-oligosaccharide or the acidic xylo-oligosaccharide composition thus obtained is ethanol,
Lower alcohols such as propanol and isopropanol, propylene glycol, dipropylene glycol,
It is dissolved in a polyhydric alcohol such as 1,3-butylene glycol and glycerin, an aqueous solution of dilute acid or dilute alkali, and the like to be contained in the anti-inflammatory agent base. Alternatively, it may be added directly to the base material component containing alcohol, ester or the like, dissolved and contained. Further, it may be added by being encapsulated in a microcapsule or contained in a liposome. The content of the acidic xylo-oligosaccharide or the acidic xylo-oligosaccharide composition in the anti-inflammatory agent can be used in the range of 0.001 to 20.0% (hereinafter, all "mass%"), but 0.01 to 10.0% is more preferable.
【００１９】本発明の抗炎症剤の用途としては、一般的
な炎症による痛みやかゆみの改善を目的とした医薬品、
医薬部外品及び化粧品等の薬用化粧品の他に、アトピー
性皮膚炎の皮膚の炎症に伴うかゆみや炎症及び花粉症に
伴う炎症の軽減を目的とした医薬品、医薬部外品、化粧
品及び機能性食品としても使用することが出来る。ま
た、汎用化粧品成分による炎症予防を目的とした成分と
しても用いることが出来る。更に、紙おむつを構成する
センターシートや吸収体等の吸収性物品、お尻ふきやウ
エットティッシュ等のシート状製品に適当な方法で含浸
させることにより、おむつかぶれの予防・改善等の抗炎
症機能を付加した製品を得ることも出来る。The anti-inflammatory agent of the present invention can be used as a drug for improving pain and itch due to general inflammation,
In addition to cosmeceutical products such as quasi-drugs and cosmetics, drugs, quasi-drugs, cosmetics and functionality for reducing itching and inflammation associated with skin inflammation of atopic dermatitis and inflammation associated with hay fever It can also be used as food. It can also be used as a component for the purpose of preventing inflammation caused by general-purpose cosmetic components. Furthermore, by impregnating absorbent articles such as center sheets and absorbent materials that make up diapers and sheet products such as buttocks and wet tissues by an appropriate method, anti-inflammatory functions such as prevention and improvement of diaper rash are added. You can also get the product.
【００２０】本発明に係わる抗炎症剤には、本発明の効
果を損なわない範囲内で、医薬品、医薬部外品、化粧
品、機能性食品、吸収性物品及びシート状製品等に配合
し得る油脂類、界面活性剤、保湿剤、水溶性高分子類、
顔料、色素、防腐剤、抗酸化剤、紫外線吸収剤等を含有
させることができる。また、例えば、オキシベンゾン、
トラネキサム酸、感光素３０１号、４０１号、塩酸ジフ
ェンヒドラジン、アデノシン酸、カラミン、水溶性アズ
レン、紫根エキス、当帰エキス、ワレモコウエキス、ア
ミノカプロン酸、サリチル酸、ビサボロール等を配合し
て、抗炎症作用を相乗的に強化することも出来る。The anti-inflammatory agent according to the present invention is a fat or oil that can be blended with pharmaceuticals, quasi drugs, cosmetics, functional foods, absorbent articles, sheet-like products, etc. within a range that does not impair the effects of the present invention. , Surfactants, humectants, water-soluble polymers,
A pigment, a dye, a preservative, an antioxidant, an ultraviolet absorber, etc. can be contained. Also, for example, oxybenzone,
Tranexamic acid, Photosensitizer Nos. 301 and 401, diphenhydrazine hydrochloride, adenosine acid, calamine, water-soluble azulene, purple root extract, toki extract, waremoko extract, aminocaproic acid, salicylic acid, bisabolol, etc. are mixed for anti-inflammatory action. Can be synergistically strengthened.
【００２１】本発明の抗炎症剤の剤型は任意であり、水
性液剤、ローション剤、乳剤、ゲル剤、クリーム、軟
膏、エアゾール剤、カプセル剤等の基剤形態で医薬品、
医薬部外品、化粧品、機能性食品等とすることが出来
る。また、本発明の酸性キシロオリゴ糖を抗炎症剤とし
て、紙、フィルム、成形体、吸収性物品等の物品に含有
させることも可能である。この際にも、前記抗炎症剤基
剤への配合と同様に、全物品質量中、0.001〜20.0％の
範囲で使用することができるが、0.01〜10.0％がより好
ましい。The dosage form of the anti-inflammatory agent of the present invention is arbitrary, and the drug is in the form of a base such as an aqueous solution, lotion, emulsion, gel, cream, ointment, aerosol and capsule.
It can be quasi-drugs, cosmetics, functional foods and the like. Further, the acidic xylooligosaccharide of the present invention can be contained as an anti-inflammatory agent in articles such as papers, films, molded articles and absorbent articles. Also in this case, similar to the case of blending with the anti-inflammatory agent base, it can be used in the range of 0.001 to 20.0% in the total mass of the article, but 0.01 to 10.0% is more preferable.
【００２２】[0022]
【実施例】以下、本発明について実施例により詳説す
る。本発明はこれにより限定されるものではない。ま
ず、各測定法の概要、本発明で有効成分として含有させ
た酸性キシロオリゴ糖組成物（UX10、UX5、UX2）の調製
例１〜調製例３を示す。EXAMPLES The present invention will be described in detail below with reference to examples. The present invention is not limited to this. First, an outline of each measuring method and Preparation Examples 1 to 3 of the acidic xylooligosaccharide composition (UX10, UX5, UX2) contained as an active ingredient in the present invention will be shown.
【００２３】＜測定法の概要＞
(1) 全糖量の定量：全糖量は検量線をＤ−キシロース
（和光純薬工業（株）製）を用いて作製し、フェノール
硫酸法（還元糖の定量法、学会出版センター発行）にて
定量した。
(2) 還元糖量の定量：還元糖量は検量線をＤ−キシロー
ス（和光純薬工業（株）製）を用いて作製、ソモジ−ネ
ルソン法（還元糖の定量法、学会出版センター発行）に
て定量した。
(3) ウロン酸量の定量：ウロン酸は検量線をＤ−グルク
ロン酸（和光純薬工業（株）製）を用いて作製、カルバ
ゾール硫酸法（還元糖の定量法、学会出版センター発
行）にて定量した。
(4) 平均重合度の決定法：サンプル糖液を50℃に保ち15
000rpmにて15分遠心分離し不溶物を除去し上清液の全糖
量を還元糖量（共にキシロース換算）で割って平均重合
度を求めた。
(5) 酸性キシロオリゴ糖の分析方法：オリゴ糖鎖の分布
はイオンクロマトグラフ（ダイオネクス社製、分析用カ
ラム：Ｃａｒｂｏ Ｐａｃ ＰＡ−１０）を用いて分析
した。分離溶媒には100mMのNaOH溶液を用い、溶出溶媒
には前述の分離溶媒に酢酸ナトリウムを500mMとなるよ
うに添加し、溶液比で、分離溶媒：溶出溶媒＝４：６と
なるような直線勾配を組み分離した。得られたクロマト
グラムより、キシロース鎖長の上限と下限との差を求め
た。
(6) オリゴ糖１分子あたりのウロン酸残基数の決定法
サンプル糖液を50℃に保ち15000rpmにて15分遠心分離し
不溶物を除去し上清液のウロン酸量（Ｄ−グルクロン酸
換算）を還元糖量（キシロース換算）で割ってオリゴ糖
１分子あたりのウロン酸残基数を求めた。
(7) 酵素力価の定義：酵素として用いたキシラナーゼの
活性測定にはカバキシラン（シグマ社製）を用いた。酵
素力価の定義はキシラナーゼがキシランを分解すること
で得られる還元糖の還元力をＤＮＳ法（還元糖の定量
法、学会出版センター発行）を用いて測定し、１分間に
１マイクロモルのキシロースに相当する還元力を生成さ
せる酵素量を１ユニットとした。<Outline of measurement method> (1) Quantification of total sugar amount: For the total sugar amount, a calibration curve was prepared using D-xylose (manufactured by Wako Pure Chemical Industries, Ltd.), and the phenol-sulfuric acid method (reducing sugar was used. Quantitative method, published by Academic Society Publishing Center). (2) Quantification of reducing sugar amount: The reducing sugar amount was prepared by using a calibration curve using D-xylose (manufactured by Wako Pure Chemical Industries, Ltd.), Somogyi-Nelson method (quantitative method for reducing sugar, published by Academic Publishing Center). Was quantified at. (3) Determination of the amount of uronic acid: For uronic acid, a calibration curve was prepared using D-glucuronic acid (manufactured by Wako Pure Chemical Industries, Ltd.) and subjected to the carbazole sulfuric acid method (quantitative method for reducing sugars, published by Academic Publishing Center). Was quantified. (4) Determination of average degree of polymerization: Keep sample sugar solution at 50 ° C
Insoluble matter was removed by centrifugation at 000 rpm for 15 minutes, and the total sugar amount in the supernatant was divided by the reducing sugar amount (both converted to xylose) to obtain the average degree of polymerization. (5) Method for analyzing acidic xylo-oligosaccharide: The distribution of oligosaccharide chains was analyzed using an ion chromatograph (Dionex, analytical column: Carbo Pac PA-10). A 100 mM NaOH solution was used as the separation solvent, sodium acetate was added to the above-mentioned separation solvent so that the concentration was 500 mM, and the solution ratio was a linear gradient such that the separation solvent: elution solvent = 4: 6. And separated. From the obtained chromatogram, the difference between the upper limit and the lower limit of the xylose chain length was obtained. (6) Method for determining the number of uronic acid residues per molecule of oligosaccharide The sample sugar solution was kept at 50 ° C. and centrifuged at 15000 rpm for 15 minutes to remove insoluble materials, and the amount of uronic acid in the supernatant solution (D-glucuronic acid). The number of uronic acid residues per molecule of oligosaccharide was determined by dividing (converted) by the amount of reducing sugar (converted to xylose). (7) Definition of enzyme titer: Kabaxylan (manufactured by Sigma) was used to measure the activity of xylanase used as an enzyme. The enzyme titer is defined by measuring the reducing power of a reducing sugar obtained by degrading xylan by xylanase, using the DNS method (quantitative method for reducing sugar, published by Academic Publishing Center), and 1 micromol xylose per minute. The amount of the enzyme that produces the reducing power corresponding to was set to 1 unit.
【００２４】＜酸性キシロオリゴ糖組成物の調整例＞
＜調製例１＞混合広葉樹チップ（国内産広葉樹70％、ユ
ーカリ30％）を原料として、クラフト蒸解及び酸素脱リ
グニン工程により、酸素脱リグニンパルプスラリー（カ
ッパー価9.6、パルプ粘度25.1cps）を得た。スラリーか
らパルプをろ別、洗浄した後、パルプ濃度10％、ｐＨ8
に調製したパルプスラリーを用いて以下のキシラナーゼ
による酵素処理を行った。<Preparation Example of Acidic Xylooligosaccharide Composition><Preparation Example 1> Mixed hardwood chips (70% domestic hardwood and 30% eucalyptus domestically) are used as raw materials in a kraft cooking and oxygen delignification process to produce oxygen delignified pulp slurry. (Kappa number 9.6, pulp viscosity 25.1 cps) was obtained. After filtering and washing the pulp from the slurry, pulp concentration 10%, pH 8
Using the pulp slurry prepared in the above, the following enzyme treatment with xylanase was performed.
【００２５】バチルスsp.S-2113株（独立行政法人産業
技術総合研究所特許微生物寄託センター、寄託菌株FERM
BP-5264）の生産するキシラナーゼを１単位／パルプｇ
となるように添加した後、60℃で120分間処理した。そ
の後、ろ過によりパルプ残渣を除去し、酵素処理液1050
Ｌを得た。Bacillus sp. S-2113 strain (Incorporated Administrative Agency National Institute of Advanced Industrial Science and Technology, Patent Microorganism Depository Center, Deposited Strain FERM
1 unit of xylanase produced by BP-5264) / g pulp
Then, it was treated at 60 ° C. for 120 minutes. Then, the pulp residue is removed by filtration, and the enzyme treatment liquid 1050
L was obtained.
【００２６】次に、得られた酵素処理液を濃縮工程、希
酸処理工程、精製工程の順に供した。濃縮工程では、逆
浸透膜（日東電工（株）製、RO NTR-7410）を用いて濃
縮液（４０倍濃縮）を調製した。希酸処理工程では、得
られた濃縮液のｐＨを3.5に調整した後、121℃で60分間
加熱処理し、リグニンなどの高分子夾雑物の沈殿を形成
させた。さらに、この沈殿をセラミックフィルターろ過
で取り除くことにより、希酸処理溶液を得た。Next, the obtained enzyme-treated solution was subjected to a concentration step, a dilute acid treatment step, and a purification step in this order. In the concentration step, a concentrated liquid (40 times concentrated) was prepared using a reverse osmosis membrane (RO NTR-7410 manufactured by Nitto Denko Corporation). In the dilute acid treatment step, the pH of the obtained concentrated liquid was adjusted to 3.5, and then the mixture was heated at 121 ° C. for 60 minutes to form a precipitate of polymer impurities such as lignin. Further, this precipitate was removed by filtration with a ceramic filter to obtain a dilute acid treatment solution.
【００２７】精製工程では、限外濾過・脱色工程、吸着
工程の順に供した。限外濾過・脱色工程では、希酸処理
溶液を限外ろ過膜（オスニクス社製、分画分子量8000）
を通過させた後、活性炭（和光純薬（株）製）770gの添
加及びセラミックフィルター濾過により脱色処理液を得
た。吸着工程では、脱色処理液を強陽イオン交換樹脂
（三菱化学（株）製ＰＫ２１８）、強陰イオン交換樹脂
（三菱化学（株）製ＰＡ４０８）、強陽イオン交換樹脂
（三菱化学（株）製ＰＫ２１８）各100kgを充填したカ
ラムに順次通過させた後、弱陰イオン交換樹脂（三菱化
学（株）製ＷＡ３０）100kgを充填したカラムに供し
た。この弱陰イオン交換樹脂充填カラムから75mMのNaCl
溶液によって溶出した溶液をスプレードライ処理するこ
とによって、酸性キシロオリゴ糖組成物の粉末（全糖量
353g、回収率13.1％）を得た。以下、この酸性キシロオ
リゴ糖組成物をUX10とする。前述の測定方法により、UX
10は平均重合度10.3、キシロース鎖長の上限と下限との
差は10、酸性キシロオリゴ糖１分子あたりウロン酸残基
を１つ含む糖組成化合物であった。In the purification step, an ultrafiltration / decolorization step and an adsorption step were performed in this order. In the ultrafiltration / decolorization process, the dilute acid treatment solution is used as an ultrafiltration membrane (manufactured by Osnix, molecular weight cutoff 8000).
After passing through, a decolorizing treatment liquid was obtained by adding 770 g of activated carbon (manufactured by Wako Pure Chemical Industries, Ltd.) and filtering with a ceramic filter. In the adsorption step, the decolorization treatment liquid was a strong cation exchange resin (PK218 manufactured by Mitsubishi Chemical Co., Ltd.), a strong anion exchange resin (PA408 manufactured by Mitsubishi Chemical Co., Ltd.), and a strong cation exchange resin (manufactured by Mitsubishi Chemical Co., Ltd.). PK218) was sequentially passed through a column packed with 100 kg of each, and then subjected to a column packed with 100 kg of a weak anion exchange resin (WA30 manufactured by Mitsubishi Chemical Corporation). From this weak anion exchange resin packed column 75 mM NaCl
By spray-drying the solution eluted with the solution, the acidic xylooligosaccharide composition powder (total sugar content
353 g, recovery rate 13.1%) was obtained. Hereinafter, this acidic xylooligosaccharide composition is referred to as UX10. With the above measurement method, UX
10 was an average degree of polymerization 10.3, the difference between the upper limit and the lower limit of the xylose chain length was 10, and it was a sugar composition compound containing one uronic acid residue per molecule of acidic xylooligosaccharide.
【００２８】＜調製例２＞調整例１と同様にして得られ
た希酸処理液1160mlに、スミチームＸ28mgを添加し、40
℃で20時間反応させた。活性炭9.8gの添加及び加熱処理
（70℃、１時間）により酵素を失活させた後、セラミッ
クフィルターで活性炭を除去した。スミチームＸ処理液
を調整例１と同様の精製工程を経て、酸性キシロオリゴ
糖組成物の粉末（全糖量21.3ｇ、回収率22.2％）を得
た。以下、この酸性キシロオリゴ糖組成物をUX5とす
る。前述の測定方法により、UX5は平均重合度4.8、キシ
ロース鎖長の上限と下限との差は9、酸性キシロオリゴ
糖１分子あたりウロン酸残基を１つ含む糖組成化合物で
あった。<Preparation Example 2> To 1160 ml of the dilute acid treatment liquid obtained in the same manner as in Preparation Example 1, 28 mg of Sumizyme X was added, and 40
The reaction was carried out at 0 ° C for 20 hours. After deactivating the enzyme by adding 9.8 g of activated carbon and heat treatment (70 ° C., 1 hour), the activated carbon was removed with a ceramic filter. The Sumizyme X-treated solution was subjected to the same purification steps as in Preparation Example 1 to obtain a powder of the acidic xylooligosaccharide composition (total sugar amount: 21.3 g, recovery rate: 22.2%). Hereinafter, this acidic xylooligosaccharide composition is referred to as UX5. According to the above-mentioned measurement method, UX5 was a sugar composition compound having an average degree of polymerization of 4.8, a difference between the upper and lower limits of xylose chain length of 9, and one uronic acid residue per one molecule of acidic xylooligosaccharide.
【００２９】＜調製例３＞調整例１より得られたUX10の
10％水溶液100mlに、スミチームＸ50mgを添加し、60
℃、20時間反応後、弱アニオン交換樹脂（ＷＡ３０）10
gを充填したカラムに供した。カラムを水洗した後、75m
MのNaCl溶液によって溶出した溶液を凍結乾燥すること
によって、酸性キシロオリゴ糖組成物粉末（全糖量2.1
g、回収率21％）を得た。以下、この酸性キシロオリゴ
糖組成物をUX2とする。前述の測定方法により、UX2は平
均重合度2.3、キシロース鎖長の上限と下限との差は2、
酸性キシロオリゴ糖１分子あたりウロン酸残基を１つ含
む糖組成化合物であった。<Preparation Example 3> UX10 obtained from Preparation Example 1
To 100 ml of 10% aqueous solution, add 50 mg of Sumizyme X, and add 60
After reacting at ℃ for 20 hours, weak anion exchange resin (WA30) 10
It was applied to a column filled with g. 75m after washing the column with water
The acidic xylooligosaccharide composition powder (total sugar content 2.1%) was obtained by freeze-drying the solution eluted with M NaCl solution.
g, recovery rate 21%) was obtained. Hereinafter, this acidic xylooligosaccharide composition is referred to as UX2. By the above measurement method, UX2 has an average degree of polymerization of 2.3, the difference between the upper limit and the lower limit of the xylose chain length is 2,
It was a sugar composition compound containing one uronic acid residue per molecule of acidic xylooligosaccharide.
【００３０】次に、得られた酸性キシロオリゴ糖組成物
を用いて行ったマウスの耳浮腫抑制試験の概要及び結果
を実施例１に示す。また、酸性キシロオリゴ糖組成物を
含有する薬用化粧品（クリーム及び乳液）の処方と製造
法を、実施例２及び実施例３に示す。Next, Example 1 shows the outline and results of a mouse ear edema inhibitory test conducted using the obtained acidic xylooligosaccharide composition. In addition, the prescription and manufacturing method of the cosmeceutical products (cream and emulsion) containing the acidic xylooligosaccharide composition are shown in Examples 2 and 3.
【００３１】＜実施例１＞
＜マウス耳浮腫抑制活性試験の概要＞接触皮膚炎のモデ
ルとして、ICR系マウス（雄、４週齢、日本チャールズ
リバー（株）製、購入後１週間予備飼育）を用いた。炎
症性浮腫惹起物質であるＴＰＡ（１２−O−テトラデカ
ノイルホルボール−１３−アセテート）0.05％のエタノ
ール溶液50μｌをマウスの右耳だけに塗布した後、5時
間後に、右耳に形成された浮腫の厚さにより炎症の程度
を測定した。すなわち、Mitutoyo Series 293microcali
perで左右の耳の厚さを測定し、その差を求めた。酸性
キシロオリゴ糖組成物及びインドメタシン（陽性対照）
のエタノール溶液は、ＴＰＡを塗布する３０分前に両耳
に予め塗布後、上記処理を行い、ＴＰＡだけを塗った場
合に対する浮腫抑制率を算出し、抗炎症効果とした。そ
の結果を表１に示す。<Example 1><Summary of mouse ear edema inhibitory activity test> As a model of contact dermatitis, ICR mouse (male, 4 weeks old, manufactured by Japan Charles River Co., Ltd., preliminarily reared for 1 week after purchase) Was used. 50 μl of an ethanol solution containing 0.05% TPA (12-O-tetradecanoylphorbol-13-acetate), which is an inflammatory edema-inducing substance, was applied to the right ear of the mouse, and 5 hours later, it was formed in the right ear. The degree of inflammation was measured by the thickness of the edema. That is, Mitutoyo Series 293microcali
The thickness of the left and right ears was measured with per, and the difference was calculated. Acidic xylooligosaccharide composition and indomethacin (positive control)
The ethanol solution was applied to both ears 30 minutes before the application of TPA, and then the above treatment was performed, and the edema inhibitory rate in the case where only TPA was applied was calculated and used as the anti-inflammatory effect. The results are shown in Table 1.
【００３２】[0032]
【表１】 [Table 1]
【００３３】表１より明らかなように、酸性キシロオリ
ゴ糖組成物には顕著な抗炎症効果が認められた。特に、
UX5、５％はインドメタシン１％以上の効果があった。As is clear from Table 1, the acidic xylooligosaccharide composition had a remarkable anti-inflammatory effect. In particular,
UX5, 5% was more effective than indomethacin 1%.
【００３４】また、酸性キシロオリゴ糖組成物５％（５
０％エタノール溶液）100μｌをＣ３Ｈマウス（雄、６
週齢、日本チャールズリバー（株）製）の背皮に約１ヶ
月間連日塗布した結果、背皮の炎症等の副作用は観察さ
れなかった。このことは酸性キシロオリゴ糖組成物の高
い安全性を示唆している。The acidic xylooligosaccharide composition 5% (5%
100 μl of 0% ethanol solution was added to C3H mouse (male, 6
As a result of daily application to the back skin of a week-old Charles River Japan Co., Ltd. for about 1 month, no side effects such as inflammation of the back skin were observed. This suggests high safety of the acidic xylooligosaccharide composition.
【００３５】＜実施例２＞酸性キシロオリゴ糖組成物UX
10を用いて、抗炎症作用を付与した下記組成のクリーム
を常法にて製造した。
処方：（１）UX10、1.0％ （２）ステアリン酸、2.0％
（３）ステアリルアルコール、7.0％ （４）ラノリ
ン、2.0％ （５）スクワラン、5.0％ （６）グリセリ
ンモノステアリン酸エステル、2.0％ （７）ポリオキ
シエチレンセチルアルコール、3.0％ （８）２−オク
チルドデシルアルコール、6.0％ （９）プロピレング
リコール１５００、3.0％ （１０）トリエタノールア
ミン、1.0％（１１）エチルパラベン、0.3％ （１２）
精製水、残部
製造法：先ず（１）と（１２）を混合し、完全に溶解し
た後、（２）から（１１）を順次加えて完全に均一とな
るまで混合した。<Example 2> Acidic xylooligosaccharide composition UX
10 was used to produce a cream having the following composition with anti-inflammatory effect, by a conventional method. Prescription: (1) UX10, 1.0% (2) Stearic acid, 2.0%
(3) Stearyl alcohol, 7.0% (4) Lanolin, 2.0% (5) Squalane, 5.0% (6) Glycerin monostearate, 2.0% (7) Polyoxyethylene cetyl alcohol, 3.0% (8) 2-octyl Dodecyl alcohol, 6.0% (9) Propylene glycol 1500, 3.0% (10) Triethanolamine, 1.0% (11) Ethylparaben, 0.3% (12)
Purified water, balance production method: First, (1) and (12) were mixed and completely dissolved, and then (2) to (11) were sequentially added and mixed until completely uniform.
【００３６】＜実施例３＞酸性キシロオリゴ糖組成物UX
5を用いて、抗炎症作用を付与した下記組成の乳液を常
法にて製造した。
処方：（１）UX5、3.0％ （２）ステアリン酸、2.0％
（３）セチルアルコール、1.5％ （４）ワセリン、
5.0％ （５）流動パラフィン、10.0％ （６）ポリオ
キシエチレンオレイン酸エステル、2.0％ （７）ポリ
エチレングリコール、3.0％ （８）トリエタノールア
ミン、1.0％ （９）エチルパラベン、0.3％（１０）香
料、適量 （１１）精製水、残部
製造法：先ず（１）と（１１）を混合し、完全に溶解し
た後、（２）から（１０）を順次加えて完全に均一とな
るまで混合した。<Example 3> Acidic xylooligosaccharide composition UX
Using 5, the emulsion having the following composition with anti-inflammatory effect was produced by a conventional method. Prescription: (1) UX5, 3.0% (2) Stearic acid, 2.0%
(3) Cetyl alcohol, 1.5% (4) Vaseline,
5.0% (5) Liquid paraffin, 10.0% (6) Polyoxyethylene oleate, 2.0% (7) Polyethylene glycol, 3.0% (8) Triethanolamine, 1.0% (9) Ethylparaben, 0.3% (10) Fragrance, appropriate amount (11) Purified water, balance production method: First, (1) and (11) were mixed and completely dissolved, and then (2) to (10) were sequentially added and mixed until completely uniform. .
【００３７】[0037]
【発明の効果】本発明で得られる酸性キシロオリゴ糖組
成物を含有した抗炎症剤は、強い炎症阻害作用を有して
おり、医薬品、医薬部外品、化粧品、機能性食品及び雑
貨等の成分として、抗炎症、抗かゆみなどの効果が期待
でき、また、アトピー性皮膚炎によるかぶれやかゆみの
予防・改善にも有用である。The anti-inflammatory agent containing the acidic xylooligosaccharide composition obtained by the present invention has a strong anti-inflammatory effect, and is a component of pharmaceuticals, quasi drugs, cosmetics, functional foods, miscellaneous goods, etc. As such, anti-inflammatory and anti-itch effects can be expected, and it is also useful for the prevention and improvement of rash and itch due to atopic dermatitis.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.7 識別記号 ＦＩ テーマコート゛(参考） Ａ６１Ｐ 17/04 Ａ６１Ｐ 17/04 29/00 29/00 Ｃ０７Ｈ 7/033 Ｃ０７Ｈ 7/033 Ｃ０８Ｂ 37/00 Ｃ０８Ｂ 37/00 Ｇ // Ａ２３Ｌ 1/30 Ａ２３Ｌ 1/30 Ｚ Ｆターム(参考） 4B018 MD31 ME14 MF10 MF12 4C057 AA06 BB04 CC01 DD01 EE03 4C083 AC012 AC022 AC072 AC122 AC182 AC242 AC392 AC402 AC482 AC542 AD042 AD211 AD212 AD512 BB41 CC05 DD31 EE13 4C086 AA01 AA02 AA04 EA01 EA20 MA01 MA13 MA22 MA27 MA28 MA32 MA37 MA63 NA14 ZA69 ZB11 4C090 AA04 BA52 BB10 BB21 BC01 BD35 CA12 CA31 CA43 DA22 DA23 DA26 DA27 ─────────────────────────────────────────────────── ─── Continuation of front page (51) Int.Cl. 7 Identification code FI theme code (reference) A61P 17/04 A61P 17/04 29/00 29/00 C07H 7/033 C07H 7/033 C08B 37/00 C08B 37/00 G // A23L 1/30 A23L 1/30 Z F term (reference) 4B018 MD31 ME14 MF10 MF12 4C057 AA06 BB04 CC01 DD01 EE03 4C083 AC012 AC022 AC072 AC122 AC182 AC242 AC392 AC402 AC482 AC542 AD042 AD211 CC05 AD512 AD512 AD512 AD512 AD512 AD512 4C086 AA01 AA02 AA04 EA01 EA20 MA01 MA13 MA22 MA27 MA28 MA32 MA37 MA63 NA14 ZA69 ZB11 4C090 AA04 BA52 BB10 BB21 BC01 BD35 CA12 CA31 CA43 DA22 DA23 DA26 DA27
Claims (4)
有する酸性キシロオリゴ糖を有効成分とする抗炎症剤。1. An anti-inflammatory agent comprising an acidic xylooligosaccharide having a uronic acid residue in a xylooligosaccharide molecule as an active ingredient.
合度が異なるオリゴ糖の混合組成物であり、平均重合度
が2.0〜11.0であることを特徴とする請求項１に記載の
抗炎症剤。2. The anti-inflammatory agent according to claim 1, wherein the acidic xylooligosaccharide is a mixed composition of oligosaccharides having different degrees of polymerization of xylose, and has an average degree of polymerization of 2.0 to 11.0.
ルロース材料を酵素的及び／又は物理化学的に処理して
キシロオリゴ糖成分とリグニン成分の複合体を得、次い
で該複合体を酸加水分解処理してキシロオリゴ糖混合物
を得、得られるキシロオリゴ糖混合物から、１分子中に
少なくとも１つ以上のウロン酸残基を側鎖として有する
キシロオリゴ糖を分離して得たもの」であることを特徴
とする請求項１または請求項２に記載の抗炎症剤。3. The acidic xylooligosaccharide comprises: “a lignocellulosic material is enzymatically and / or physicochemically treated to obtain a complex of a xylooligosaccharide component and a lignin component, and then the complex is subjected to an acid hydrolysis treatment. Xylooligosaccharide mixture is obtained by separating from the obtained Xylooligosaccharide mixture, and xylooligosaccharides having at least one or more uronic acid residues as side chains in one molecule are obtained. The anti-inflammatory agent according to claim 1 or 2.
チル−グルクロン酸であることを特徴とする請求項１〜
請求項３のいずれかに記載の抗炎症剤。4. The uronic acid is glucuronic acid or 4-O-methyl-glucuronic acid.
The anti-inflammatory agent according to claim 3.
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| JP2002019378A JP2003221339A (en) | 2002-01-29 | 2002-01-29 | Anti-inflammatory agent |
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|---|---|---|---|
| JP2002019378A JP2003221339A (en) | 2002-01-29 | 2002-01-29 | Anti-inflammatory agent |
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|---|---|---|---|
| JP2008261686A Division JP2009057387A (en) | 2008-10-08 | 2008-10-08 | Method for producing anti-inflammatory agent for external use |
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| Publication Number | Publication Date |
|---|---|
| JP2003221339A true JP2003221339A (en) | 2003-08-05 |
Family
ID=27743252
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|---|---|---|---|
| JP2002019378A Pending JP2003221339A (en) | 2002-01-29 | 2002-01-29 | Anti-inflammatory agent |
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005089402A (en) * | 2003-09-19 | 2005-04-07 | Ogawa & Co Ltd | External anti-pruritic agent |
| JP2005089403A (en) * | 2003-09-19 | 2005-04-07 | Ogawa & Co Ltd | External anti-pruritic agent |
| US8557794B2 (en) * | 2003-10-24 | 2013-10-15 | N.V. Nutricia | Immunemodulating oligosaccharides |
| WO2018043666A1 (en) * | 2016-08-31 | 2018-03-08 | 王子ホールディングス株式会社 | Production method for acidic xylooligosaccharide |
| US11274165B2 (en) | 2017-02-28 | 2022-03-15 | Oji Holdings Corporation | Pentosan polysulfate, pharmaceutical composition, and anticoagulant |
| US11278485B2 (en) | 2017-05-31 | 2022-03-22 | Oji Holdings Corporation | Moisturizing topical preparation |
| US11312790B2 (en) | 2016-08-31 | 2022-04-26 | Oji Holdings Corporation | Production method for pentosan polysulfate |
| US11344570B2 (en) | 2017-12-20 | 2022-05-31 | Oji Holdings Corporation | Pentosan polysulfate and medicine containing pentosan polysulfate |
| US11390693B2 (en) | 2017-09-12 | 2022-07-19 | Oji Holdings Corporation | Pentosan polysulfate and method for producing pentosan polysulfate |
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| JP2000333692A (en) * | 1999-03-23 | 2000-12-05 | Oji Paper Co Ltd | Production of xylooligosaccharide |
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| JP2000050840A (en) * | 1998-08-04 | 2000-02-22 | Akihisa Shinjo | Bagasse extract solution and bagasse drink |
| JP2000333692A (en) * | 1999-03-23 | 2000-12-05 | Oji Paper Co Ltd | Production of xylooligosaccharide |
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Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005089402A (en) * | 2003-09-19 | 2005-04-07 | Ogawa & Co Ltd | External anti-pruritic agent |
| JP2005089403A (en) * | 2003-09-19 | 2005-04-07 | Ogawa & Co Ltd | External anti-pruritic agent |
| US8557794B2 (en) * | 2003-10-24 | 2013-10-15 | N.V. Nutricia | Immunemodulating oligosaccharides |
| KR20200040870A (en) | 2016-08-31 | 2020-04-20 | 오지 홀딩스 가부시키가이샤 | Method for producing acidic xyloligosaccharide and acidic xyloligosaccharide |
| WO2018043667A1 (en) | 2016-08-31 | 2018-03-08 | 王子ホールディングス株式会社 | Production method for acidic xylooligosaccharide, and acidic xylooligosaccharide |
| JPWO2018043667A1 (en) * | 2016-08-31 | 2018-08-30 | 王子ホールディングス株式会社 | Method for producing acidic xylooligosaccharide and acidic xylooligosaccharide |
| WO2018043666A1 (en) * | 2016-08-31 | 2018-03-08 | 王子ホールディングス株式会社 | Production method for acidic xylooligosaccharide |
| US11286272B2 (en) | 2016-08-31 | 2022-03-29 | Oji Holdings Corporation | Production method for acidic xylooligosaccharide, and acidic xylooligosaccharide |
| US11312790B2 (en) | 2016-08-31 | 2022-04-26 | Oji Holdings Corporation | Production method for pentosan polysulfate |
| KR102559743B1 (en) * | 2016-08-31 | 2023-07-25 | 오지 홀딩스 가부시키가이샤 | Method for producing acidic xylooligosaccharide and acidic xylooligosaccharide |
| US11274165B2 (en) | 2017-02-28 | 2022-03-15 | Oji Holdings Corporation | Pentosan polysulfate, pharmaceutical composition, and anticoagulant |
| US11278485B2 (en) | 2017-05-31 | 2022-03-22 | Oji Holdings Corporation | Moisturizing topical preparation |
| US11390693B2 (en) | 2017-09-12 | 2022-07-19 | Oji Holdings Corporation | Pentosan polysulfate and method for producing pentosan polysulfate |
| US11344570B2 (en) | 2017-12-20 | 2022-05-31 | Oji Holdings Corporation | Pentosan polysulfate and medicine containing pentosan polysulfate |
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