JPH0940690A - Steroid glycoside and medicine containing the same as active ingredient - Google Patents
Steroid glycoside and medicine containing the same as active ingredientInfo
- Publication number
- JPH0940690A JPH0940690A JP8107254A JP10725496A JPH0940690A JP H0940690 A JPH0940690 A JP H0940690A JP 8107254 A JP8107254 A JP 8107254A JP 10725496 A JP10725496 A JP 10725496A JP H0940690 A JPH0940690 A JP H0940690A
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- steroid glycoside
- glycoside
- solvent
- 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.)
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- Medicines Containing Plant Substances (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、ステロイド配糖体
及びこれを有効成分とする医薬に関する。TECHNICAL FIELD The present invention relates to a steroid glycoside and a medicine containing the same as an active ingredient.
【０００２】[0002]
【従来の技術及び発明が解決しようとする課題】現代に
おいて各種の医薬品の発明は、古来より人類の脅威であ
った種々の感染症を駆逐した。しかしこれに代わって、
循環器疾患や癌が人類の大きな脅威になっている。この
うち癌は、現在に至っても尚完全な治療法は存在せず、
死亡原因でもトップの座を保っており、人類にとって解
決すべき最優先課題となっている。2. Description of the Related Art Inventions of various medicines in recent years have eliminated various infectious diseases which have been a threat to humankind since ancient times. But instead of this,
Cardiovascular disease and cancer pose a great threat to humankind. Of these, there is still no perfect cure for cancer,
It remains the top cause of death and is a top priority issue for humankind to solve.
【０００３】従来、癌の治療は大きく分けて、外科的手
術、抗癌剤による化学療法、放射線による放射線療法の
３つに分けられる。このうち、外科的手術は初期の癌に
は有効であるが、転移を伴った癌に対しては効力が限ら
れたものとなってしまうことが多い。また、放射線療法
は浅部の癌には有効であるが、深部の癌には効力は今一
つである。更に、放射線による正常な部位への障害は無
視できず、放射線によって癌が誘起されることがあり、
無条件に癌治療に用いることは出来ない。一方、抗癌剤
による癌治療は抗癌剤の毒性が強いことが原因で、極め
て限られたものになっている。また、癌の抗癌剤に対す
る耐性も無視の出来ない大きな課題である。この様な状
況から新規の抗癌剤の登場が期待されている。Conventionally, the treatment of cancer is roughly divided into three types, that is, surgical operation, chemotherapy with an anticancer agent, and radiation therapy with radiation. Of these, surgical operation is effective for early stage cancer, but its efficacy is often limited for cancer with metastasis. Radiation therapy is also effective for superficial cancers, but is less effective for deep cancers. Furthermore, radiation damage to normal areas cannot be ignored, and radiation can cause cancer.
It cannot be used unconditionally for cancer treatment. On the other hand, cancer treatment with anti-cancer agents has been extremely limited due to the strong toxicity of anti-cancer agents. In addition, the resistance of cancer to anti-cancer agents is a major issue that cannot be ignored. Under such circumstances, the appearance of new anticancer agents is expected.
【０００４】また、現代において臓器移植は医薬品で治
療できない疾患例えば、肝臓の不全、腎臓の不全、心臓
の不全、白血病等の治療のための切り札的存在である。
特に近年になって臓器移植が盛んに行われるようになっ
てきた要因の一つに免疫抑制剤の使用により、移植直後
の被移植者の生体拒絶反応のコントロールが可能になっ
てきたことが挙げられる。しかしながら、これまでに用
いられているサイクロスポリンやシクロホスファミド等
の免疫抑制剤は、いずれも安全で、かつ十分な効果を発
現するものではなく、その使用には危険が伴い、ただで
さえ体力の落ちた臓器の不全を呈している患者に投与す
るのには困難が伴う。そこで、新規の免疫抑制剤の登場
が期待されている。[0004] In addition, organ transplantation is a trump card for treating diseases that cannot be treated with medicines, such as liver failure, kidney failure, heart failure, and leukemia.
Particularly in recent years, one of the factors that has made active use of organ transplantation is that the use of immunosuppressive agents has made it possible to control the biological rejection of transplant recipients immediately after transplantation. To be However, immunosuppressants such as cyclosporin and cyclophosphamide that have been used so far are not safe and exhibit sufficient effects, and their use is dangerous and free. Even difficult to administer to patients presenting with weakened organ failure. Therefore, the emergence of new immunosuppressants is expected.
【０００５】従って、本発明は、安全性に優れ、強い抗
癌作用及び高い免疫抑制作用を示す新規化合物を提供す
ることを目的とする。Therefore, an object of the present invention is to provide a novel compound which is excellent in safety and has a strong anticancer action and a high immunosuppressive action.
【０００６】[0006]
【課題を解決するための手段】かかる実情において、本
発明者らは鋭意検討を行った結果、ユリ科又はその近縁
の植物体を溶剤抽出及び精製すると新規のステロイド配
糖体が得られ、当該新規化合物は安全で、強い抗癌作用
及び高い免疫抑制作用を示し、医薬として有用であるこ
とを見出し本発明を完成した。In such circumstances, as a result of intensive investigations by the present inventors, a novel steroid glycoside is obtained by solvent extraction and purification of Liliaceae or its related plants. The present inventors have completed the present invention by finding that the novel compound is safe, exhibits a strong anticancer action and a high immunosuppressive action and is useful as a medicine.
【０００７】すなわち、本発明は、次の一般式（１）That is, the present invention provides the following general formula (1)
【０００８】[0008]
【化５】 Embedded image
【０００９】（式中、Ｒ1 はホルミル基又は低鎖長ヒド
ロキシアルキル基を示し、Ｒ2 はアシル基を有していて
もよい糖残基を示す。）で表わされるステロイド配糖体
及びこれを有効成分とする医薬を提供するものである。(In the formula, R 1 represents a formyl group or a low chain length hydroxyalkyl group, and R 2 represents a sugar residue which may have an acyl group.) The present invention provides a medicine containing as an active ingredient.
【００１０】[0010]
【発明の実施の形態】本発明の一般式（１）のステロイ
ド配糖体は新規化合物である。一般式（１）のＲ1 はホ
ルミル基又は低鎖長ヒドロキシアルキル基であれば特に
制限されないが、低鎖長ヒドロキシアルキル基の好まし
いものとしては、炭素数１〜４のヒドロキシアルキル基
が挙げられ、特に好ましいものとしてはヒドロキシメチ
ル基が挙げられる。BEST MODE FOR CARRYING OUT THE INVENTION The steroid glycoside represented by the general formula (1) of the present invention is a novel compound. R 1 in the general formula (1) is not particularly limited as long as it is a formyl group or a low chain length hydroxyalkyl group, but a preferable low chain length hydroxyalkyl group is a hydroxyalkyl group having 1 to 4 carbon atoms. A hydroxymethyl group is particularly preferable.
【００１１】Ｒ2 はアシル基を有していてもよい糖残基
であれば特に制限されないが、アシル基を有していても
よい二糖又は三糖の残基が好ましい。また、当該アシル
基としてはｐ−ヒドロキシベンゾイル基又はｐ−メトキ
シベンゾイル基が好ましい。R 2 is not particularly limited as long as it is a sugar residue which may have an acyl group, but is preferably a disaccharide or trisaccharide residue which may have an acyl group. Further, the acyl group is preferably a p-hydroxybenzoyl group or a p-methoxybenzoyl group.
【００１２】より好ましいＲ2 としては次式（２）又は
（３）で示される糖残基が挙げられる。More preferred R 2 is a sugar residue represented by the following formula (2) or (3).
【００１３】[0013]
【化６】 [Chemical 6]
【００１４】（式中、Ｒ2aは水素原子、ｐ−ヒドロキシ
ベンゾイル基又はｐ−メトキシベンゾイル基を示す。）(In the formula, R 2a represents a hydrogen atom, a p-hydroxybenzoyl group or a p-methoxybenzoyl group.)
【００１５】本発明化合物（１）のより好ましいものと
しては、下記一般式（４）及び（５）で表わされる化合
物が挙げられる。More preferred examples of the compound (1) of the present invention include compounds represented by the following general formulas (4) and (5).
【００１６】[0016]
【化７】 [Chemical 7]
【００１７】（式中、Ｒ1aはホルミル基又はヒドロキシ
メチル基を示し、Ｒ2aは水素原子、ｐ−ヒドロキシベン
ゾイル基又はｐ−メトキシベンゾイル基を示す。）(In the formula, R 1a represents a formyl group or a hydroxymethyl group, and R 2a represents a hydrogen atom, a p-hydroxybenzoyl group or a p-methoxybenzoyl group.)
【００１８】[0018]
【化８】 Embedded image
【００１９】（式中、Ｒ1bはホルミル基又はヒドロキシ
メチル基を示す。）(In the formula, R 1b represents a formyl group or a hydroxymethyl group.)
【００２０】本発明化合物（１）のうち特に好ましい化
合物を下表に示す。Particularly preferable compounds among the compounds (1) of the present invention are shown in the following table.
【００２１】[0021]
【表１】 [Table 1]
【００２２】[0022]
【表２】 [Table 2]
【００２３】本発明の新規ステロイド配糖体（１）は例
えばユリ科又はその近縁植物の植物体から溶媒抽出、精
製工程を経て得ることができる。The novel steroid glycoside (1) of the present invention can be obtained, for example, from a plant of Liliaceae or its closely related plants through solvent extraction and purification steps.
【００２４】ユリ科植物としては、特に制限されない
が、例えば、オルニトガラム・サンデルシアエ（Ｏｎｉ
ｔｙｈｏｇａｌｕｍ ｓａｕｎｄｅｒｓｉａｅ）等が挙
げられる。また、ユリ科の近縁植物としては、例えば、
ドラカエナ属等のリュウゼツラン科、アヤメ科又はカヤ
ツリグサ科等の植物が挙げられる。これらは、市販のも
のを用いることができる。抽出に用いる植物体の部位も
特に制限されないが、ステロイド配糖体が高い濃度で存
在する鱗茎部が好ましい。The Liliaceae plant is not particularly limited, but may be, for example, Ornithogalum sandersiae (Oni).
tyhogalum saundersiae) and the like. Further, as a closely related plant of the lily family, for example,
Examples include plants such as the agave family of the genus Dracaena, the family Iridaceae or the family Cyperaceae. As these, commercially available products can be used. The part of the plant used for extraction is not particularly limited, but a bulb part having a high concentration of steroid glycoside is preferable.
【００２５】ユリ科又はその近縁の植物体から溶媒抽出
する方法も特に制限されないが、植物体をそのまま又は
乾燥あるいは細断、粉砕等抽出に好適な形状に加工した
後極性溶媒で液液抽出等行えばよい。抽出溶媒として
は、極性溶媒が好ましく、例えば、水；メタノールやエ
タノールなどのアルコール類；ジエチルエーテルやテト
ラヒドロフラン等のエーテル類；酢酸エチルや酢酸メチ
ル等のエステル類；クロロホルムや塩化メチレン等のハ
ロゲン化炭化水素類；アセトンやメチルエチルケトン等
のケトン類；アセトニトリル等のニトリル類が挙げら
れ、これらを単独もしくは二種以上を混合して用いれば
よい。このうち好ましい溶媒として、抽出効率、安全
性、経済性の点でアルコール類を挙げることが出来る。
抽出は、室温でも溶媒の沸点付近の温度まで加熱して行
ってもよい。これは、本発明のステロイド配糖体が温度
に対して安定であるためである。抽出は、室温ならば数
日、加熱下であれば数時間溶媒に浸漬して行えばよく、
更に攪拌を加えてもよい。The method of solvent extraction from Liliaceae or closely related plants is not particularly limited, but the plants may be subjected to liquid-liquid extraction with a polar solvent as they are or after being processed into a shape suitable for extraction such as drying, shredding or crushing. You can do so. The extraction solvent is preferably a polar solvent, for example, water; alcohols such as methanol and ethanol; ethers such as diethyl ether and tetrahydrofuran; esters such as ethyl acetate and methyl acetate; halogenated carbonization such as chloroform and methylene chloride. Examples thereof include hydrogens; ketones such as acetone and methyl ethyl ketone; nitrites such as acetonitrile. These may be used alone or in combination of two or more. Among these, alcohols can be mentioned as preferable solvents in terms of extraction efficiency, safety and economy.
The extraction may be performed at room temperature or by heating to a temperature near the boiling point of the solvent. This is because the steroid glycoside of the present invention is stable against temperature. The extraction may be carried out by immersing in a solvent for several days at room temperature or for several hours if heated.
Further stirring may be added.
【００２６】ユリ科又はその近縁の植物体から溶媒抽出
された抽出物は、公知の方法により精製、単離できる。
例えば、水−ブタノールで液液抽出し大まかに夾雑物を
取り除いた後、シリカゲル、ＯＤＳ、イオン交換樹脂等
を担体としたカラムクロマトグラフィーで精製すればよ
い。The extract obtained by solvent extraction from Liliaceae or a plant related thereto can be purified and isolated by a known method.
For example, after liquid-liquid extraction with water-butanol to roughly remove impurities, it may be purified by column chromatography using silica gel, ODS, ion exchange resin or the like as a carrier.
【００２７】本発明のステロイド配糖体は、優れた抗癌
作用を有し、抗癌剤として有用である。本発明抗癌剤の
対象となる癌としては、通常の癌であれば特に制限され
ないが、特に白血病が好ましい。また、本発明のステロ
イド配糖体は、高い免疫抑制作用を有し、免疫抑制剤と
して有用である。斯かる免疫抑制剤は従来の免疫抑制剤
が用いられる場合と同様に用いることが出来る。例え
ば、臓器移植に先立って、本発明の免疫抑制剤を投与
し、拒絶反応を抑制し移植臓器の定着率を上げるために
用いたり、白血病患者に骨髄移植に先立って投与し、病
原細胞を除去するために用いたりする事が出来る。ま
た、本発明医薬には有効成分として前記ステロイド配糖
体（１）が配合されるが、当該ステロイド配糖体（１）
は有効量含まれていればよく、前記ユリ科又はその近縁
の植物体の抽出物を用いてもよい。The steroid glycoside of the present invention has an excellent anticancer activity and is useful as an anticancer agent. The cancer targeted by the anticancer agent of the present invention is not particularly limited as long as it is a normal cancer, but leukemia is particularly preferable. In addition, the steroid glycoside of the present invention has a high immunosuppressive action and is useful as an immunosuppressant. Such immunosuppressive agents can be used in the same manner as in the case where conventional immunosuppressive agents are used. For example, prior to organ transplantation, the immunosuppressive agent of the present invention is administered to suppress rejection and increase colonization of transplanted organs, or to leukemia patients prior to bone marrow transplantation to remove pathogenic cells. It can be used to do. The steroid glycoside (1) is blended as an active ingredient in the medicament of the present invention. The steroid glycoside (1)
Need only be contained in an effective amount, and an extract of the above Liliaceae or plants related thereto may be used.
【００２８】本発明の医薬を患者に投与する場合、好ま
しい投与量は、患者の年齢、体型、体調、癌の種類とス
テージ、性別等により異なるが、通常、成人一人一日当
たり、有効成分として１〜１０００mg、特に２〜１００
mgを１〜数回に分けて投与するのが好ましい。投与経路
としては、特段の限定はなく、例えば、経口投与、経直
腸投与、注射による投与などが挙げられる。このうち、
注射による投与では、例えば、静脈注射、動脈注射、門
脈注射、皮下注射、皮内注射、腹腔内注射、病巣内直接
注射等が例示できる。注射は、通常の注射でも輸液など
に混合して点滴を行ってもよい。When the medicament of the present invention is administered to a patient, the preferred dose varies depending on the patient's age, body type, physical condition, type and stage of cancer, sex, etc. ~ 1000 mg, especially 2-100
It is preferred to administer mg in 1 to several divided doses. The administration route is not particularly limited, and examples thereof include oral administration, rectal administration, and administration by injection. this house,
Examples of administration by injection include intravenous injection, arterial injection, portal vein injection, subcutaneous injection, intradermal injection, intraperitoneal injection, and intralesional direct injection. The injection may be a normal injection or a drip infusion mixed with an infusion solution.
【００２９】本発明の医薬は、上記ステロイド配糖体を
有効成分として含有するが、それ以外に通常の医薬組成
物で用いられている剤形化のための任意成分を任意の配
合量で含有することができる。この様な任意成分として
は、賦形剤、結合剤、崩壊剤、乳化・可溶化・分散剤、
滑沢剤、コーティング剤、徐放性被膜形成剤、矯味矯臭
剤、着色剤、安定剤、等張剤、油脂類、溶媒、リポソー
ム形成剤等が例示できる。本発明の医薬はこれら任意成
分と共に常法に従って製剤化される。The pharmaceutical composition of the present invention contains the above-mentioned steroid glycoside as an active ingredient, but other than the above, it contains optional ingredients for forming a dosage form, which are used in usual pharmaceutical compositions, in arbitrary blending amounts. can do. Such optional components include excipients, binders, disintegrants, emulsifying / solubilizing / dispersing agents,
Lubricants, coating agents, sustained-release film forming agents, flavoring agents, coloring agents, stabilizers, isotonic agents, fats and oils, solvents, liposome forming agents and the like can be exemplified. The medicament of the present invention is formulated together with these optional components according to a conventional method.
【００３０】上記剤形化のための任意成分以外にも、本
発明の抗癌剤の場合は、通常癌治療に用いられる医薬品
類を更に含有させることもできる。この様な医薬品とし
ては、アドリアマイシン、マイトマイシン、ネオカルチ
ノスタチン、ビンクリスチン、タキソール、５ＦＵ等の
抗癌剤、モルヒネ等の痛み止め成分、ステロイド剤、リ
ピオドール等の血管栓塞剤等が挙げられる。また、上記
剤形化の為の任意成分以外にも、本発明の免疫抑制剤の
場合は、通常免疫抑制剤を用いる治療に用いられる医薬
品類を含有させることもできる。このような医薬品とし
ては、メチシリン、テトラサイクリン、セファロスポリ
ン、セファロスポロール等の抗生物質、シクロフォスフ
ァミドやメルカプトプリン等の従来の免疫抑制剤、ステ
ロイド剤等が挙げられる。In addition to the above optional ingredients for formulation, the anticancer agent of the present invention may further contain pharmaceuticals usually used for treating cancer. Examples of such drugs include anticancer agents such as adriamycin, mitomycin, neocarzinostatin, vincristine, taxol, 5FU, pain relievers such as morphine, steroids, and vascular embolizers such as lipiodol. Further, in addition to the above optional components for formulation, the immunosuppressant of the present invention may contain pharmaceuticals that are usually used for treatment using an immunosuppressant. Examples of such a drug include antibiotics such as methicillin, tetracycline, cephalosporin and cephalosporol, conventional immunosuppressive agents such as cyclophosphamide and mercaptopurine, and steroids.
【００３１】[0031]
【発明の効果】本発明のステロイド配糖体は、優れた抗
癌作用及び高い免疫抑制作用を有する。更に、ユリ科の
多くの植物の鱗茎が広く食用に供されていることから安
全性が高い。INDUSTRIAL APPLICABILITY The steroid glycoside of the present invention has an excellent anticancer action and a high immunosuppressive action. Furthermore, since the bulbs of many Liliaceae plants are widely used for food, they are highly safe.
【００３２】[0032]
【実施例】次に本発明を実施例を挙げて更に具体的に説
明するが、これらは、単に例示であって本発明を制限す
るものではない。EXAMPLES Next, the present invention will be described more specifically by way of examples, but these are merely examples and do not limit the present invention.
【００３３】実施例１ 製造例 園芸店より購入したオルニトガラム・サンデルシアエ
（Ｏｎｉｔｙｈｏｇａｌｕｍ ｓａｕｎｄｅｒｓｉａ
ｅ）の新鮮鱗茎１０kgを細かく切り刻んだ後、１０ｌの
メタノールで２回、３時間温浸し、濾過により不溶物を
取り除いた後に溶媒を除去し、３ ｌのブタノールと３
ｌの水で液液抽出を行い、ブタノール層を得た。溶媒除
去し残渣をダイヤイオンＨＰ−２０を用いたイオン交換
カラムクロマトグラフィー（溶出溶媒；水：メタノール
＝１００：０→０：１００、エタノール、酢酸エチ
ル）、シリカゲルカラムクロマトグラフィー（溶出溶
媒；クロロホルム：メタノール：水＝１９：１：０→
７：４：１）、ＯＤＳカラムを装着した高速液体クロマ
トグラフィー（溶出溶媒；水：メタノール＝３０：７０
→５：９５、水：アセトニトリル＝３０：７０）で順次
精製し、精製物１〜７を得た。Example 1 Manufacturing Example Ornitogalum saundersiae purchased from a garden store.
10 kg of fresh bulb of e) was finely chopped, and then digested twice with 10 l of methanol for 3 hours to remove insoluble matter by filtration, and then the solvent was removed, and 3 l of butanol and 3
Liquid-liquid extraction was performed with 1 l of water to obtain a butanol layer. The solvent was removed and the residue was subjected to ion exchange column chromatography using Diaion HP-20 (elution solvent; water: methanol = 100: 0 → 0: 100, ethanol, ethyl acetate), silica gel column chromatography (elution solvent; chloroform: Methanol: water = 19: 1: 0 →
7: 4: 1), high performance liquid chromatography equipped with an ODS column (elution solvent; water: methanol = 30: 70)
→ 5: 95, water: acetonitrile = 30: 70) to successively purify to obtain purified products 1 to 7.
【００３４】（精製物１：収量１５mg）この精製物は、
以下の方法で分析を行ったところ、前記化合物Ａである
ことがわかった。(Purified Product 1: Yield 15 mg)
When analyzed by the following method, it was found to be the above compound A.
【００３５】[0035]
【表３】性状：白色粉末［α］D 26−６０度 ＦＡＢ−ＭＡＳＳ：［Ｍ−Ｈ］-；７３５ ＩＲ（ＫＢｒ錠剤）cm-1：３４００、２９５０、２９２
０1 Ｈ−ＮＭＲ（重ピリジン）ppm:10.15(1H,s), 6.38(1H,
s), 5.31(1H,d),5.14(1H,d), 5.04(1H,d), 4.80(1H,br
s), 4.62(1H,dd), 1.80(3H,s),1.76(3H,s), 1.71(3H,
s), 1.00(3H,d), 0.97(3H,s)13 Ｃ−ＮＭＲ（重ピリジン）ppm:37.5, 30.2, 78.0, 3
9.0, 141.0, 121.2,32.2, 33.5, 50.2, 37.0, 22.6, 3
3.7, 59.3, 52.7, 33.5, 69.9, 59.6,207.3, 19.4, 31.
3, 18.6, 47.6, 98.3, 126.3, 134.3, 26.0, 18.8,100.
5, 79.7, 77.9, 71.9, 78.3, 62.7, 102.1, 72.6, 72.
9, 74.2, 69.5,18.7[Table 3] Properties: White powder [α] D 26 -60 degrees FAB-MASS: [MH] − ; 735 IR (KBr tablet) cm −1 : 3400, 2950, 292
0 1 H-NMR (heavy pyridine) ppm: 10.15 (1H, s), 6.38 (1H,
s), 5.31 (1H, d), 5.14 (1H, d), 5.04 (1H, d), 4.80 (1H, br
s), 4.62 (1H, dd), 1.80 (3H, s), 1.76 (3H, s), 1.71 (3H,
s), 1.00 (3H, d), 0.97 (3H, s) 13 C-NMR (heavy pyridine) ppm: 37.5, 30.2, 78.0, 3
9.0, 141.0, 121.2,32.2, 33.5, 50.2, 37.0, 22.6, 3
3.7, 59.3, 52.7, 33.5, 69.9, 59.6, 207.3, 19.4, 31.
3, 18.6, 47.6, 98.3, 126.3, 134.3, 26.0, 18.8, 100.
5, 79.7, 77.9, 71.9, 78.3, 62.7, 102.1, 72.6, 72.
9, 74.2, 69.5, 18.7
【００３６】（精製物２：収量６５mg）この精製物は、
以下の方法で分析を行ったところ、前記化合物Ｂである
ことがわかった。(Purified Product 2: Yield 65 mg)
When analyzed by the following method, it was found to be the compound B.
【００３７】[0037]
【表４】性状：白色粉末［α］D 26−３２．８度 ＦＡＢ−ＭＡＳＳ：［Ｍ−Ｈ］-；８５５ ＩＲ（ＫＢｒ錠剤）cm-1：３４００、２９２０、１７０
０、１６００1 Ｈ−ＮＭＲ（重ピリジン）ppm:10.13(1H,s), 8.29(2H,
d), 7.16(2H,d),6.46(1H,br s), 6.14(1H,dd), 5.07(1
H,d), 1.81(3H,br s),1.72(3H,br s), 1.57(3H,d), 1.0
0(3H,d), 0.95(3H,s)13 Ｃ−ＮＭＲ（重ピリジン）ppm:37.4, 30.0, 78.4, 3
9.4, 141.0, 121.5,32.3, 33.6, 50.3, 36.9, 22.6, 3
3.6, 59.3, 52.7, 33.5, 69.9, 59.6,207.3, 19.5, 31.
3, 18.1, 47.6, 98.3, 126.3, 134.4, 26.1, 18.9,100.
8, 79.7, 77.3, 71.8, 78.4, 62.7, 101.6, 72.7, 70.
6, 76.4, 67.1,18.7, 122.0, 132.6, 116.1, 163.6, 16
6.7TABLE 4 Properties: white powder [α] D 26 -32.8 ° FAB-MASS: [M-H ] -; 855 IR (KBr tablet) cm -1: 3400,2920,170
0, 1600 1 H-NMR (heavy pyridine) ppm: 10.13 (1H, s), 8.29 (2H,
d), 7.16 (2H, d), 6.46 (1H, br s), 6.14 (1H, dd), 5.07 (1
H, d), 1.81 (3H, br s), 1.72 (3H, br s), 1.57 (3H, d), 1.0
0 (3H, d), 0.95 (3H, s) 13 C-NMR (heavy pyridine) ppm: 37.4, 30.0, 78.4, 3
9.4, 141.0, 121.5,32.3, 33.6, 50.3, 36.9, 22.6, 3
3.6, 59.3, 52.7, 33.5, 69.9, 59.6, 207.3, 19.5, 31.
3, 18.1, 47.6, 98.3, 126.3, 134.4, 26.1, 18.9,100.
8, 79.7, 77.3, 71.8, 78.4, 62.7, 101.6, 72.7, 70.
6, 76.4, 67.1, 18.7, 122.0, 132.6, 116.1, 163.6, 16
6.7
【００３８】（精製物３：収量６５．２mg）この精製物
は、以下の方法で分析を行ったところ、前記化合物Ｃで
あることがわかった。(Purified product 3: Yield 65.2 mg) This purified product was analyzed by the following method, and was found to be the compound C.
【００３９】[0039]
【表５】性状：白色粉末［α］D 26−４．０度 ＦＡＢ−ＭＡＳＳ：［Ｍ］-；８７０ ＩＲ（ＫＢｒ錠剤）cm-1：３４２５、２９５０、１７１
０、１６９５1 Ｈ−ＮＭＲ（重ピリジン）ppm:10.15(1H,s), 8.27(2H,
d), 7.01(2H,d),6.45(1H,br s), 6.13(1H,dd), 5.48(1
H,br s), 5.15(1H,d), 5.08(1H,d),5.02(1H,over lappi
ng to H20peak), 1.81(3H,br s), 1.72(3H,br s),1.56
(3H,d), 1.01(3H,d), 0.97(3H,s)13 Ｃ−ＮＭＲ（重ピリジン）ppm:37.2, 30.3, 78.3, 3
9.3, 141.0, 121.4,32.3, 33.6, 50.1, 37.0, 22.5, 3
3.8, 59.2, 52.5, 33.4, 69.9, 59.5,207.3, 19.6, 31.
2, 18.0, 47.6, 98.3, 126.2, 134.4, 26.0, 18.8,100.
7, 79.6, 77.3, 71.7, 78.1, 62.6, 101.6, 72.6, 70.
5, 76.5, 67.0,18.6, 123.5, 132.2, 114.1, 163.8, 16
6.4, 55.5[Table 5] Properties: White powder [α] D 26 -4.0 degree FAB-MASS: [M] − ; 870 IR (KBr tablet) cm −1 : 3425, 2950, 171
0,169 5 1 H-NMR (heavy pyridine) ppm: 10.15 (1H, s), 8.27 (2H,
d), 7.01 (2H, d), 6.45 (1H, br s), 6.13 (1H, dd), 5.48 (1
H, br s), 5.15 (1H, d), 5.08 (1H, d), 5.02 (1H, over lappi
ng to H 2 0peak), 1.81 (3H, br s), 1.72 (3H, br s), 1.56
(3H, d), 1.01 (3H, d), 0.97 (3H, s) 13 C-NMR (heavy pyridine) ppm: 37.2, 30.3, 78.3, 3
9.3, 141.0, 121.4, 32.3, 33.6, 50.1, 37.0, 22.5, 3
3.8, 59.2, 52.5, 33.4, 69.9, 59.5, 207.3, 19.6, 31.
2, 18.0, 47.6, 98.3, 126.2, 134.4, 26.0, 18.8, 100.
7, 79.6, 77.3, 71.7, 78.1, 62.6, 101.6, 72.6, 70.
5, 76.5, 67.0, 18.6, 123.5, 132.2, 114.1, 163.8, 16
6.4, 55.5
【００４０】（精製物４：収量２０．８mg）この精製物
は、以下の方法で分析を行ったところ、前記化合物Ｄで
あることがわかった。(Purified product 4: Yield 20.8 mg) This purified product was analyzed by the following method and was found to be the compound D.
【００４１】[0041]
【表６】性状：白色粉末［α］D 26−２０．０度 ＦＡＢ−ＭＡＳＳ：［Ｍ］-；８５８ ＩＲ（ＫＢｒ錠剤）cm-1：３４２５、２９５０、２９２
０、２８７０、１６９０1 Ｈ−ＮＭＲ（重ピリジン）ppm:8.31(2H,d), 7.17(2H,
d), 6.46(1H,br s),6.15(1H,dd), 5.49(1H,br s), 5.29
(1H,d), 5.07(1H,d),5.02(1H,over lapping to H2Opea
k), 1.87(3H,br s), 1.73(3H,br s),1.57(3H,d), 1.28
(3H,d), 1.03(3H,s)13 Ｃ−ＮＭＲ（重ピリジン）ppm:37.5, 30.5, 78.5, 3
9.4, 141.0, 122.0,32.8, 31.8, 50.7, 37.1, 21.4, 3
5.2, 46.8, 53.3, 33.8, 70.7, 60.6,60.4, 19.4, 31.
5, 18.1, 48.2, 98.7, 127.3, 133.5, 26.1, 19.5, 10
0.7,79.6, 77.3, 71.8, 78.3, 62.6, 101.6, 72.6, 70.
5, 76.3, 67.0, 18.9,121.9, 132.6, 116.1, 163.5, 16
6.7[Table 6] Properties: White powder [α] D 26 -20.0 degrees FAB-MASS: [M] − ; 858 IR (KBr tablet) cm −1 : 3425, 2950, 292
0, 2870, 1690 1 H-NMR (heavy pyridine) ppm: 8.31 (2H, d), 7.17 (2H,
d), 6.46 (1H, br s), 6.15 (1H, dd), 5.49 (1H, br s), 5.29
(1H, d), 5.07 (1H, d), 5.02 (1H, over lapping to H 2 Opea
k), 1.87 (3H, br s), 1.73 (3H, br s), 1.57 (3H, d), 1.28
(3H, d), 1.03 (3H, s) 13 C-NMR (heavy pyridine) ppm: 37.5, 30.5, 78.5, 3
9.4, 141.0, 122.0, 32.8, 31.8, 50.7, 37.1, 21.4, 3
5.2, 46.8, 53.3, 33.8, 70.7, 60.6, 60.4, 19.4, 31.
5, 18.1, 48.2, 98.7, 127.3, 133.5, 26.1, 19.5, 10
0.7,79.6, 77.3, 71.8, 78.3, 62.6, 101.6, 72.6, 70.
5, 76.3, 67.0, 18.9, 121.9, 132.6, 116.1, 163.5, 16
6.7
【００４２】（精製物５：収量７６．３mg）この精製物
は、以下の方法で分析を行ったところ、前記化合物Ｅで
あることがわかった。(Purified product 5: Yield 76.3 mg) This purified product was analyzed by the following method, and was found to be the compound E.
【００４３】[0043]
【表７】性状：白色粉末［α］D 26−１６．０度 ＦＡＢ−ＭＡＳＳ：［Ｍ］-；８７２ ＩＲ（ＫＢｒ錠剤）cm-1：３４２５、２９２５、２８５
０、１６９５1 Ｈ−ＮＭＲ（重ピリジン）ppm:8.27(2H,s), 6.99(2H,
d), 6.44(1H,br s),6.13(1H,dd), 5.53(1H,br s), 5.20
(1H,d), 5.06(1H,d), 4.88(1H,d),1.87(3H,br s), 1.74
(3H,br s), 1.56(3H,d), 1.28(3H,d), 1.03(3H,s)13 Ｃ−ＮＭＲ（重ピリジン）ppm:30.5, 78.6, 39.6, 14
1.1, 122.0, 32.8,31.9, 50.6, 37.2, 21.4, 35.2, 46.
8, 53.2, 33.9, 70.6, 60.6, 60.4,19.4, 31.5, 18.1,
48.2, 98.7, 127.3, 133.5, 26.1, 19.5, 100.9, 79.6,
77.4, 71.8, 78.3, 62.6, 101.6, 72.5, 70.5, 76.7, 6
6.9, 18.9, 123.5,132.3, 114.1, 163.7, 166.4, 55.4[Table 7] Properties: White powder [α] D 26 -16.0 degrees FAB-MASS: [M] − ; 872 IR (KBr tablet) cm −1 : 3425, 2925, 285
0,169 5 1 H-NMR (heavy pyridine) ppm: 8.27 (2H, s), 6.99 (2H,
d), 6.44 (1H, br s), 6.13 (1H, dd), 5.53 (1H, br s), 5.20
(1H, d), 5.06 (1H, d), 4.88 (1H, d), 1.87 (3H, br s), 1.74
(3H, br s), 1.56 (3H, d), 1.28 (3H, d), 1.03 (3H, s) 13 C-NMR (heavy pyridine) ppm: 30.5, 78.6, 39.6, 14
1.1, 122.0, 32.8, 31.9, 50.6, 37.2, 21.4, 35.2, 46.
8, 53.2, 33.9, 70.6, 60.6, 60.4, 19.4, 31.5, 18.1,
48.2, 98.7, 127.3, 133.5, 26.1, 19.5, 100.9, 79.6,
77.4, 71.8, 78.3, 62.6, 101.6, 72.5, 70.5, 76.7, 6
6.9, 18.9, 123.5, 132.3, 114.1, 163.7, 166.4, 55.4
【００４４】（精製物６：収量１９０mg）この精製物
は、以下の方法で分析を行ったところ、前記化合物Ｆで
あることがわかった。(Purified product 6: Yield 190 mg) This purified product was analyzed by the following method and found to be the compound F.
【００４５】[0045]
【表８】性状：白色粉末［α］D 26−４９．６度 ＦＡＢ−ＭＡＳＳ：［Ｍ−Ｈ］-；８９７ ＩＲ（ＫＢｒ錠剤）cm-1：３４００、２９２０、１７０
０1 Ｈ−ＮＭＲ（重ピリジン）ppm:10.12(1H,s), 6.37(1H,
br s), 5.85(1H,d),5.37(1H,br d), 5.13(2H,d), 4.99
(1H,m), 4.92(1H,br d), 4.76(1H,br s),4.70(1H,dd),
4.50(1H,dd), 4.43(1H,dd), 4.25(1H,dd), 4.16(2H,d
d),3.95(1H,m), 2.85(1H,br d), 2.69(1H,br d), 2.58
(1H,m), 2.11(1H,br d),1.80(3H,br s), 1.71(3H,br
s), 1.65(3H,br d), 1.04(1H,m), 0.99(3H,d),0.82(3H,
s)13 Ｃ−ＮＭＲ（重ピリジン）ppm:37.5, 78.8, 39.4, 14
1.3, 121.0, 32.1,33.5, 50.2, 36.9, 22.6, 33.6, 59.
3, 52.7, 33.5, 69.9, 59.6, 207.3,19.4, 31.3, 18.6,
47.6, 98.3, 126.3, 134.3, 26.0, 19.0, 101.2, 80.
7,79.2, 71.7, 78.1, 62.8, 102.1, 78.7, 79.3, 72.3,
72.6, 74.4, 69.8,18.8Table 8 Properties: White powder [α] D 26 -49.6 degrees FAB-MASS: [MH] − ; 897 IR (KBr tablet) cm −1 : 3400, 2920, 170
0 1 H-NMR (heavy pyridine) ppm: 10.12 (1H, s), 6.37 (1H,
br s), 5.85 (1H, d), 5.37 (1H, br d), 5.13 (2H, d), 4.99
(1H, m), 4.92 (1H, br d), 4.76 (1H, br s), 4.70 (1H, dd),
4.50 (1H, dd), 4.43 (1H, dd), 4.25 (1H, dd), 4.16 (2H, d
d), 3.95 (1H, m), 2.85 (1H, br d), 2.69 (1H, br d), 2.58
(1H, m), 2.11 (1H, br d), 1.80 (3H, br s), 1.71 (3H, br
s), 1.65 (3H, br d), 1.04 (1H, m), 0.99 (3H, d), 0.82 (3H,
s) 13 C-NMR (heavy pyridine) ppm: 37.5, 78.8, 39.4, 14
1.3, 121.0, 32.1, 33.5, 50.2, 36.9, 22.6, 33.6, 59.
3, 52.7, 33.5, 69.9, 59.6, 207.3, 19.4, 31.3, 18.6,
47.6, 98.3, 126.3, 134.3, 26.0, 19.0, 101.2, 80.
7,79.2, 71.7, 78.1, 62.8, 102.1, 78.7, 79.3, 72.3,
72.6, 74.4, 69.8, 18.8
【００４６】（精製物７：収量２０．８mg）この精製物
は、以下の方法で分析を行ったところ、前記化合物Ｇで
あることがわかった。(Purified product 7: Yield 20.8 mg) This purified product was analyzed by the following method and was found to be the compound G.
【００４７】[0047]
【表９】性状：白色粉末［α］D 26−４８．０度 ＦＡＢ−ＭＡＳＳ：［Ｍ］-；９００ ＩＲ（ＫＢｒ錠剤）cm-1：３４００、２９２０1 Ｈ−ＮＭＲ（重ピリジン）ppm:6.39(1H,s), 5.88(1H,
d), 5.41(1H,d),5.29(1H,d), 5.15(1H,d), 5.07(1H,d),
4.76(1H,br s), 4.70(1H,br d),4.00(1H,m), 1.85(3H,
d), 1.82(3H,d), 1.73(3H,s), 1.27(3H,d),0.87(3H,s)13 Ｃ−ＮＭＲ（重ピリジン）ppm:37.6, 30.1, 78.8, 3
9.4, 141.3, 121.5,32.7, 31.7, 50.7, 37.1, 21.4, 3
5.2, 46.8, 53.3, 33.8, 70.7, 60.6,60.5, 19.4, 101.
1, 80.7, 79.1, 71.8, 78.1, 62.8, 102.3, 78.7, 79.
3,72.3, 77.1, 63.0, 102.0, 72.3, 77.1, 63.0, 102.
0, 72.3, 72.6, 74.4,69.8, 18.9[Table 9] Properties: White powder [α] D 26 -48.0 degrees FAB-MASS: [M] - ; 900 IR (KBr tablet) cm -1 : 3400, 2920 1 H-NMR (heavy pyridine) ppm: 6.39 (1H, s), 5.88 (1H,
d), 5.41 (1H, d), 5.29 (1H, d), 5.15 (1H, d), 5.07 (1H, d),
4.76 (1H, br s), 4.70 (1H, br d), 4.00 (1H, m), 1.85 (3H,
d), 1.82 (3H, d), 1.73 (3H, s), 1.27 (3H, d), 0.87 (3H, s) 13 C-NMR (heavy pyridine) ppm: 37.6, 30.1, 78.8, 3
9.4, 141.3, 121.5,32.7, 31.7, 50.7, 37.1, 21.4, 3
5.2, 46.8, 53.3, 33.8, 70.7, 60.6, 60.5, 19.4, 101.
1, 80.7, 79.1, 71.8, 78.1, 62.8, 102.3, 78.7, 79.
3,72.3, 77.1, 63.0, 102.0, 72.3, 77.1, 63.0, 102.
0, 72.3, 72.6, 74.4, 69.8, 18.9
【００４８】実施例２ 急性毒性 化合物Ａ〜Ｇの急性毒性を１群５匹のＩＣＲ雄性マウス
を用いて調べた。即ち、各化合物を２mg／匹腹腔内投与
し、１４日後に生死を判定した。その後動物を屠殺し、
解剖し各臓器の異常の有無を調べた。結果は１４日目に
於ける死亡例はなく、剖検結果も異常を認めなかった。
これより本発明のステロイド配糖体は、安全性に優れる
ことが判る。Example 2 Acute Toxicity The acute toxicity of compounds A to G was examined using 5 ICR male mice per group. That is, each compound was intraperitoneally administered at a dose of 2 mg / mouse, and the life or death was judged 14 days later. Then the animal is slaughtered,
It was dissected and examined for abnormalities in each organ. As a result, there were no deaths on the 14th day, and the autopsy result showed no abnormality.
From this, it is understood that the steroid glycoside of the present invention is excellent in safety.
【００４９】実施例３ 抗癌作用 白血病細胞ＨＬ−６０を用いて抗癌作用を検討した。即
ち、１０％ＦＢＳ含有ＭＥＭで前培養したＨＬ−６０細
胞を１０6 個培養皿に入れ、これに各種濃度で薬物を含
有するように調整した１０％ＦＢＳ含有ＭＥＭを加え、
２時間５％炭酸ガス混合ガス気流下、３７℃で２時間イ
ンキュベートした。その後、１０％ＦＢＳ含有ＭＥＭで
２回洗浄した後７日間この培地で混合ガス気流下培養
し、生きている細胞を染色し、５０％の細胞が死滅する
濃度（ＩＣ50値）を求めた。結果を表１０に示す。尚、
ポジティブコントロールにはエトポシドを用いた。本発
明のステロイド配糖体は優れた抗癌作用を有しているこ
とが判る。Example 3 Anticancer Effect The anticancer effect was examined using leukemia cells HL-60. That is, 10 6 HL-60 cells pre-cultured with 10% FBS-containing MEM were placed in a culture dish, and 10% FBS-containing MEM adjusted to contain a drug at various concentrations was added thereto,
It was incubated for 2 hours at 37 ° C. for 2 hours under a gas flow of 5% carbon dioxide gas. Then, the cells were washed twice with 10% FBS-containing MEM and then cultured in this medium for 7 days under a mixed gas flow to stain living cells, and the concentration at which 50% of cells died (IC 50 value) was determined. The results are shown in Table 10. still,
Etoposide was used as a positive control. It can be seen that the steroid glycoside of the present invention has an excellent anticancer action.
【００５０】[0050]
【表１０】 [Table 10]
【００５１】実施例４ 免疫抑制作用 ＣＤ４レセプターを有するＴ細胞由来の培養細胞ＭＯＬ
Ｔ−４細胞を用いて免疫抑制作用を検討した。即ち、１
０％ＦＢＳ含有ＭＥＭで前培養したＭＯＬＴ−４細胞を
１０6 個培養皿に入れ、これに各種濃度で薬物を含有す
るように調整した１０％ＦＢＳ含有ＭＥＭを加え２時間
５％炭酸ガス混合ガス気流下３７℃で２時間インキュベ
ートした。その後、１０％ＦＢＳ含有ＭＥＭで２回洗浄
した後７日間この培地で混合ガス気流下培養し、生きて
いる細胞を染色し、５０％の細胞が死滅する濃度（ＩＣ
50値）を求めた。結果を表１１に示す。尚、ポジティブ
コントロールにはメトトレキセートを用いた。本発明の
ステロイド配糖体は優れた免疫抑制作用を有しているこ
とが判る。Example 4 Immunosuppressive action T cell-derived cultured cell MOL having CD4 receptor
The immunosuppressive effect was examined using T-4 cells. That is, 1
MOLT-4 cells pre-cultured with 0% FBS-containing MEM were placed in 10 6 culture dishes, and 10% FBS-containing MEM adjusted to contain the drug at various concentrations was added thereto, and the mixture was mixed with 5% carbon dioxide gas for 2 hours. Incubated for 2 hours at 37 ° C. under air flow. Then, the cells were washed twice with 10% FBS-containing MEM and then cultured in this medium for 7 days in a mixed gas stream to stain living cells, and 50% of the cells were killed (IC
50 values). The results are shown in Table 11. Methotrexate was used as a positive control. It can be seen that the steroid glycoside of the present invention has an excellent immunosuppressive action.
【００５２】[0052]
【表１１】 [Table 11]
【００５３】実施例５ 免疫抑制作用 ヒト末梢血リンパ球を用いて免疫抑制作用を検討した。
即ち、ヒトから採血した末梢血にＥＤＴＡを添加した
後、モノポリ分離液に重層させ延伸分離しリンパ球を得
た。このリンパ球を１０％ＦＢＳ含有ＭＥＭで前培養し
た後、１０6 個培養皿に入れ、これに各種濃度で薬物を
含有するように調整した１０％ＦＢＳ含有ＭＥＭを加え
２時間５％炭酸ガス混合ガス気流下３７℃で２時間イン
キュベートした。その後、１０％ＦＢＳ含有ＭＥＭで２
回洗浄した後７日間この培地で混合ガス気流下培養し、
生きている細胞を染色し、５０％の細胞が死滅する濃度
（ＩＣ50値）を求めた。結果を表１２に示す。尚、ポジ
ティブコントロールにはメトトレキセートを用いた。本
発明のステロイド配糖体は優れた免疫抑制作用を有して
いることが判る。Example 5 Immunosuppressive Effect The immunosuppressive effect was examined using human peripheral blood lymphocytes.
That is, EDTA was added to peripheral blood collected from a human, and the monopoly separation solution was overlaid and stretched and separated to obtain lymphocytes. The lymphocytes were pre-cultured with 10% FBS-containing MEM, then placed in 10 6 culture dish, and 10% FBS-containing MEM adjusted to contain the drug at various concentrations was added thereto, and mixed with 5% carbon dioxide gas for 2 hours. Incubated for 2 hours at 37 ° C under a gas stream. Then 2 with MEM containing 10% FBS
After washing twice, culturing in this medium under mixed gas flow for 7 days,
Live cells were stained and the concentration at which 50% of the cells died (IC 50 value) was determined. The results are shown in Table 12. Methotrexate was used as a positive control. It can be seen that the steroid glycoside of the present invention has an excellent immunosuppressive action.
【００５４】[0054]
【表１２】 [Table 12]
───────────────────────────────────────────────────── フロントページの続き (72)発明者 岡 希太郎 東京都大田区東矢口３丁目19番８号 (72)発明者 平野 俊彦 神奈川県津久井郡相模湖町若柳633−７ (72)発明者 三巻 祥浩 東京都八王子市めじろ台２−８−５−205 (72)発明者 黒田 明平 東京都練馬区南田中３−31−６−209 (72)発明者 藤井 昭男 神奈川県横浜市神奈川区高島台27−１ ポ ーラ化成工業株式会社横浜研究所内 (72)発明者 宮田 善之 神奈川県横浜市神奈川区高島台27−１ ポ ーラ化成工業株式会社横浜研究所内 ─────────────────────────────────────────────────── ─── Continuation of front page (72) Inventor Kitaro Oka 3-19-8 Higashiyaguchi, Ota-ku, Tokyo (72) Inventor Toshihiko Hirano 633-7 Wakayanagi, Sagamiko-cho, Tsukui-gun, Kanagawa (72) Inventor Maki Yoshihiro Tokyo 2-8-5-205 Mejirodai, Hachioji City, Tokyo (72) Inventor Meihei Kuroda 3-31-6-209 Minamitanaka, Nerima-ku, Tokyo (72) Inventor Akio Fujii 27 Takashimadai, Kanagawa-ku, Yokohama-shi, Kanagawa -1 Polar Chemical Industry Co., Ltd. Yokohama Laboratory (72) Inventor Yoshiyuki Miyata 27-1 Takashimadai, Kanagawa-ku, Kanagawa Prefecture Kanagawa Pref.
Claims (7)
ル基を示し、Ｒ2 はアシル基を有していてもよい糖残基
を示す。）で表わされるステロイド配糖体。1. The following general formula (1): (In the formula, R 1 represents a formyl group or a low chain length hydroxyalkyl group, and R 2 represents a sugar residue which may have an acyl group.).
ヒドロキシメチル基であり、Ｒ2 がアシル基を有してい
てもよい二糖残基又は三糖残基である請求項１記載のス
テロイド配糖体。2. In the general formula (1), R 1 is a formyl group or a hydroxymethyl group, and R 2 is a disaccharide residue or a trisaccharide residue which may have an acyl group. The steroid glycoside described.
ヒドロキシメチル基であり、Ｒ2 が次式（２）又は
（３） 【化２】 （式中、Ｒ2aは水素原子、ｐ−ヒドロキシベンゾイル基
又はｐ−メトキシベンゾイル基を示す。）である請求項
１記載のステロイド配糖体。3. In the general formula (1), R 1 is a formyl group or a hydroxymethyl group, and R 2 is the following formula (2) or (3): (In the formula, R 2a represents a hydrogen atom, a p-hydroxybenzoyl group or a p-methoxybenzoyl group.) The steroid glycoside according to claim 1.
し、Ｒ2aは水素原子、ｐ−ヒドロキシベンゾイル基又は
ｐ−メトキシベンゾイル基を示す。）又は一般式（５） 【化４】 （式中、Ｒ1bはホルミル基又はヒドロキシメチル基を示
す。）で表わされる化合物である請求項１記載のステロ
イド配糖体。4. The following general formula (4): (In the formula, R 1a represents a formyl group or a hydroxymethyl group, and R 2a represents a hydrogen atom, a p-hydroxybenzoyl group or a p-methoxybenzoyl group.) Or the general formula (5): The steroid glycoside according to claim 1, which is a compound represented by the formula (wherein R 1b represents a formyl group or a hydroxymethyl group).
ロイド配糖体を有効成分とする医薬。5. A medicine comprising the steroid glycoside according to any one of claims 1 to 4 as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8107254A JPH0940690A (en) | 1995-05-23 | 1996-04-26 | Steroid glycoside and medicine containing the same as active ingredient |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12375995 | 1995-05-23 | ||
| JP7-123759 | 1995-05-23 | ||
| JP7-123760 | 1995-05-23 | ||
| JP12376095 | 1995-05-23 | ||
| JP8107254A JPH0940690A (en) | 1995-05-23 | 1996-04-26 | Steroid glycoside and medicine containing the same as active ingredient |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0940690A true JPH0940690A (en) | 1997-02-10 |
Family
ID=27310932
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8107254A Pending JPH0940690A (en) | 1995-05-23 | 1996-04-26 | Steroid glycoside and medicine containing the same as active ingredient |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0940690A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1189611A4 (en) * | 1999-06-14 | 2003-05-02 | Cancer Res Ventures Ltd | Cancer therapy |
| WO2005058934A3 (en) * | 2003-12-18 | 2005-10-06 | Unibioscreen Sa | Glycosylated steroid derivatives with anti-migratory activity |
| US7462642B2 (en) | 2002-03-22 | 2008-12-09 | Cancer Research Technology Limited | Anti-cancer combinations |
| US7510830B2 (en) | 2000-07-28 | 2009-03-31 | Cancer Research Technology Limited | Cancer treatment by combination therapy |
| US7585893B2 (en) | 2002-11-01 | 2009-09-08 | Cancer Research Technology Limited | Anti-cancer composition comprising DMXAA or related compound |
| US7863320B2 (en) | 2001-09-03 | 2011-01-04 | Cancer Research Technology Limited | Anti-cancer combinations |
| JP2011506308A (en) * | 2007-12-07 | 2011-03-03 | ハンコック ファーム．カンパニー インコーポレーティッド | Graft rejection inhibitory composition containing Cordyceps mycelium extract as an active ingredient |
-
1996
- 1996-04-26 JP JP8107254A patent/JPH0940690A/en active Pending
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1189611A4 (en) * | 1999-06-14 | 2003-05-02 | Cancer Res Ventures Ltd | Cancer therapy |
| US7510830B2 (en) | 2000-07-28 | 2009-03-31 | Cancer Research Technology Limited | Cancer treatment by combination therapy |
| US7863320B2 (en) | 2001-09-03 | 2011-01-04 | Cancer Research Technology Limited | Anti-cancer combinations |
| US7863321B2 (en) | 2001-09-03 | 2011-01-04 | Cancer Research Technology Limited | Anti-cancer combinations |
| US7863322B2 (en) | 2001-09-03 | 2011-01-04 | Cancer Research Technology Limited | Anti-cancer combinations |
| US7868040B2 (en) | 2001-09-03 | 2011-01-11 | Cancer Research Technology Limited | Anti-cancer combinations |
| US7868039B2 (en) | 2001-09-03 | 2011-01-11 | Cancer Research Technology Limited | Anti-cancer combinations |
| US7462642B2 (en) | 2002-03-22 | 2008-12-09 | Cancer Research Technology Limited | Anti-cancer combinations |
| US7585893B2 (en) | 2002-11-01 | 2009-09-08 | Cancer Research Technology Limited | Anti-cancer composition comprising DMXAA or related compound |
| WO2005058934A3 (en) * | 2003-12-18 | 2005-10-06 | Unibioscreen Sa | Glycosylated steroid derivatives with anti-migratory activity |
| JP2011506308A (en) * | 2007-12-07 | 2011-03-03 | ハンコック ファーム．カンパニー インコーポレーティッド | Graft rejection inhibitory composition containing Cordyceps mycelium extract as an active ingredient |
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