JPS5927824A - Antilipemic agent - Google Patents
Antilipemic agentInfo
- Publication number
- JPS5927824A JPS5927824A JP13653582A JP13653582A JPS5927824A JP S5927824 A JPS5927824 A JP S5927824A JP 13653582 A JP13653582 A JP 13653582A JP 13653582 A JP13653582 A JP 13653582A JP S5927824 A JPS5927824 A JP S5927824A
- Authority
- JP
- Japan
- Prior art keywords
- trimethylsteroid
- cycloartenol
- agent
- antilipemic agent
- main component
- 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
- 239000003524 antilipemic agent Substances 0.000 title claims abstract description 6
- XZEUYTKSAYNYPK-UHFFFAOYSA-N 3beta-29-Norcycloart-24-en-3-ol Natural products C1CC2(C)C(C(CCC=C(C)C)C)CCC2(C)C2CCC3C(C)C(O)CCC33C21C3 XZEUYTKSAYNYPK-UHFFFAOYSA-N 0.000 claims abstract description 10
- RRTBTJPVUGMUNR-UHFFFAOYSA-N Cycloartanol Natural products C12CCC(C(C(O)CC3)(C)C)C3C2(CC)CCC2(C)C1(C)CCC2C(C)CCCC(C)C RRTBTJPVUGMUNR-UHFFFAOYSA-N 0.000 claims abstract description 10
- HVXLSFNCWWWDPA-UHFFFAOYSA-N Isocycloartenol Natural products C1CC(O)C(C)(C)C2C31CC13CCC3(C)C(C(CCCC(C)=C)C)CCC3(C)C1CC2 HVXLSFNCWWWDPA-UHFFFAOYSA-N 0.000 claims abstract description 10
- HXQRIQXPGMPSRW-UHZRDUGNSA-N Pollinastanol Natural products O[C@@H]1C[C@H]2[C@@]3([C@]4([C@H]([C@@]5(C)[C@@](C)([C@H]([C@H](CCCC(C)C)C)CC5)CC4)CC2)C3)CC1 HXQRIQXPGMPSRW-UHZRDUGNSA-N 0.000 claims abstract description 10
- ONQRKEUAIJMULO-YBXTVTTCSA-N cycloartenol Chemical compound CC(C)([C@@H](O)CC1)[C@H]2[C@@]31C[C@@]13CC[C@]3(C)[C@@H]([C@@H](CCC=C(C)C)C)CC[C@@]3(C)[C@@H]1CC2 ONQRKEUAIJMULO-YBXTVTTCSA-N 0.000 claims abstract description 10
- YNBJLDSWFGUFRT-UHFFFAOYSA-N cycloartenol Natural products CC(CCC=C(C)C)C1CCC2(C)C1(C)CCC34CC35CCC(O)C(C)(C)C5CCC24C YNBJLDSWFGUFRT-UHFFFAOYSA-N 0.000 claims abstract description 10
- FODTZLFLDFKIQH-UHFFFAOYSA-N cycloartenol trans-ferulate Natural products C1=C(O)C(OC)=CC(C=CC(=O)OC2C(C3CCC4C5(C)CCC(C5(C)CCC54CC53CC2)C(C)CCC=C(C)C)(C)C)=C1 FODTZLFLDFKIQH-UHFFFAOYSA-N 0.000 claims abstract description 10
- BDHQMRXFDYJGII-UEBIAWITSA-N 24-methylenecycloartanol Chemical compound CC(C)([C@@H](O)CC1)[C@H]2[C@@]31C[C@@]13CC[C@]3(C)[C@@H]([C@H](C)CCC(=C)C(C)C)CC[C@@]3(C)[C@@H]1CC2 BDHQMRXFDYJGII-UEBIAWITSA-N 0.000 claims abstract description 7
- KKSCKZFKHNHGEO-UHFFFAOYSA-N 24-methylenecycloartanol Natural products CC(CCC(=C)C(C)(C)O)C1CCC2C3CCC4C(C)(C)C(O)CCC45CC35CCC12C KKSCKZFKHNHGEO-UHFFFAOYSA-N 0.000 claims abstract description 7
- BJZVHTWNCLKZGN-SPQNPFHSSA-N 24-methylidenecycloartanol Natural products CC(C)C(=C)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C(C)(C)[C@@H](O)CC[C@@]45C[C@@]35CC[C@]12C BJZVHTWNCLKZGN-SPQNPFHSSA-N 0.000 claims abstract description 7
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 abstract description 9
- 239000008280 blood Substances 0.000 abstract description 4
- 210000004369 blood Anatomy 0.000 abstract description 4
- 239000002775 capsule Substances 0.000 abstract description 4
- 239000000843 powder Substances 0.000 abstract description 4
- 229940076810 beta sitosterol Drugs 0.000 abstract description 3
- LGJMUZUPVCAVPU-UHFFFAOYSA-N beta-Sitostanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 LGJMUZUPVCAVPU-UHFFFAOYSA-N 0.000 abstract description 3
- NJKOMDUNNDKEAI-UHFFFAOYSA-N beta-sitosterol Natural products CCC(CCC(C)C1CCC2(C)C3CC=C4CC(O)CCC4C3CCC12C)C(C)C NJKOMDUNNDKEAI-UHFFFAOYSA-N 0.000 abstract description 3
- 239000003795 chemical substances by application Substances 0.000 abstract description 3
- KZJWDPNRJALLNS-VJSFXXLFSA-N sitosterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]1(C)CC2 KZJWDPNRJALLNS-VJSFXXLFSA-N 0.000 abstract description 3
- 229950005143 sitosterol Drugs 0.000 abstract description 3
- 239000006188 syrup Substances 0.000 abstract description 2
- 235000020357 syrup Nutrition 0.000 abstract description 2
- 239000003826 tablet Substances 0.000 abstract description 2
- 229930182558 Sterol Natural products 0.000 abstract 1
- 239000002671 adjuvant Substances 0.000 abstract 1
- 235000012000 cholesterol Nutrition 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 230000001603 reducing effect Effects 0.000 abstract 1
- 150000003432 sterols Chemical class 0.000 abstract 1
- 235000003702 sterols Nutrition 0.000 abstract 1
- 235000013311 vegetables Nutrition 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 235000002378 plant sterols Nutrition 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 235000016709 nutrition Nutrition 0.000 description 2
- 230000035764 nutrition Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 229910002016 Aerosil® 200 Inorganic materials 0.000 description 1
- SGNBVLSWZMBQTH-FGAXOLDCSA-N Campesterol Natural products O[C@@H]1CC=2[C@@](C)([C@@H]3[C@H]([C@H]4[C@@](C)([C@H]([C@H](CC[C@H](C(C)C)C)C)CC4)CC3)CC=2)CC1 SGNBVLSWZMBQTH-FGAXOLDCSA-N 0.000 description 1
- BTEISVKTSQLKST-UHFFFAOYSA-N Haliclonasterol Natural products CC(C=CC(C)C(C)(C)C)C1CCC2C3=CC=C4CC(O)CCC4(C)C3CCC12C BTEISVKTSQLKST-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- -1 Polyoxyethylene monostearate Polymers 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- CHRHZFQUDFAQEQ-UHFFFAOYSA-L calcium;2-hydroxyacetate Chemical compound [Ca+2].OCC([O-])=O.OCC([O-])=O CHRHZFQUDFAQEQ-UHFFFAOYSA-L 0.000 description 1
- SGNBVLSWZMBQTH-PODYLUTMSA-N campesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](C)C(C)C)[C@@]1(C)CC2 SGNBVLSWZMBQTH-PODYLUTMSA-N 0.000 description 1
- 235000000431 campesterol Nutrition 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000007902 hard capsule Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 230000004903 negative regulation of intestinal cholesterol absorption Effects 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229950008882 polysorbate Drugs 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は、トリメチルステロイドを主成分とする抗脂血
剤に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to an antilipemic agent containing trimethylsteroid as a main component.
β−シトステロールやカンペステロールナトの植物ステ
ロールは血清コレステ日−ルを低下させることが知られ
ており、その作用機序は一般に、腸管からのコレステロ
ール吸収阻害と考えられている。植物ステロールにその
量の’Ａ。Plant sterols such as β-sitosterol and campesterol are known to lower serum cholesterol levels, and their mechanism of action is generally thought to be inhibition of cholesterol absorption from the intestinal tract. That amount of 'A' in plant sterols.
〜’／１ｏｏのトリメチルステロイド、例えばシクロア
ルテノール、２４−メチレンシクロアルタノールを添加
して投与すると、通常の植物ステロール剤の’Ａｏ以下
の投与量で同等の効果を有していることが知られている
。（％開開５７−１８６１７号公報参照）。It is known that when trimethylsteroids such as cycloartenol and 24-methylenecycloartanol are added and administered at ~'Ao/1oo, the same effect is obtained at doses less than 'Ao' of ordinary plant sterol agents. It is being (See %Kokai No. 57-18617).
しかし、トリメチルステロイドを含む太豆油不ケン化物
中のアルコール類には血中コレステロール低下作用がな
いと報告されている（栄養と食糧、１９巻、４３９頁、
１９６６年）、、本発明者らはトリメチルステロイド
について、その血中コレステロール低下作用を調べたと
ころ、β−シトステロールなどの植物ステロールと同等
の効果を有することが判り、本発明を完成した。However, it has been reported that alcohols in unsaponifiables of fat soybean oil, including trimethylsteroids, have no effect on lowering blood cholesterol (Nutrition and Food, Vol. 19, p. 439).
(1966), the present inventors investigated the blood cholesterol-lowering effect of trimethylsteroids and found that it had an effect equivalent to that of plant sterols such as β-sitosterol, thereby completing the present invention.
本発明で用いられるトリメチルステロイドとしては、シ
クロアルテノール、シクロアルテノール、２４−メチレ
ンシクロアルタノール等を挙げることができるが、シク
ロアルテノールおよび２４−メチレンシクロアルタノー
ルが特に好ましい。Examples of the trimethylsteroid used in the present invention include cycloartenol, cycloartenol, 24-methylenecycloartanol, and the like, with cycloartenol and 24-methylenecycloartanol being particularly preferred.
シクロアルテノールおよび２４−メチレンシクロアルタ
ノールの調製法は特開昭５７−４８６１７号公報に記載
されている。A method for preparing cycloartenol and 24-methylenecycloartanol is described in JP-A-57-48617.
本則は、錠剤、散剤、カプセル、シロップ等の経口投与
剤形として調製される。１日の投与量ハ、成人に対して
活性成分として通常０．２〜１５ｇであるが、好適には
０．５〜５Ｉである。The present invention is prepared in oral dosage forms such as tablets, powders, capsules, and syrups. The daily dose for adults is usually 0.2 to 15 g of the active ingredient, preferably 0.5 to 5 I.
実施例
平均体Ｍ１２５ ｇのウィスター系雄性ラットを用い、
コントロール群およびその他の群とも一群１０匹として
２２日間第１表に示す飼料を自由摂取させた。試験終了
後、ラットｔエーテルで麻酔し採血を行いスベリイーウ
ェブ改良法（栄養と食糧、２８巻、９８負、 １９７５
年）により血漿コレステロール値を測定した。その結果
第１表
（単位：チ）
第２表
ａ：Ｆ２ｆｔ？：＆ζ対しての有意差 Ｐ＜ｏ、ｏ５本
結果によればシクロアルテノールまたは２４−メチレン
シクロアルタノールを飼料中に添加することＫより血漿
コレステロールが減少することは明らかである。Example Using Wistar male rats with an average weight of 125 g,
Each group of 10 animals in both the control group and other groups was allowed to freely consume the feed shown in Table 1 for 22 days. After the test, the rat was anesthetized with t-ether, blood was collected, and the improved smooth web method (Nutrition and Food, Vol. 28, 98 Negative, 1975)
Plasma cholesterol levels were measured according to 2010). As a result, Table 1 (Unit: CH) Table 2 a: F2ft? : Significant difference for &ζ P<o, o5 According to these results, it is clear that adding cycloartenol or 24-methylenecycloartanol to the feed reduces plasma cholesterol more than K.
例えはシクロアルテノールをラットおよびマウスに５Ｊ
ｉｌ ／Ｋｙ経口投与しても、死亡しなかった。For example, cycloartenol was administered to rats and mice by 5J.
Oral administration of il/Ky did not result in death.
〔製剤例１〕
シクロアルテノール２６０Ｊｉ’、ビタミン０１［ｌｌ
１１ク工ン酸５ｇ、繊維素グリコール酸カルシウム２０
、！ｉ’、ラウリル硫酸ナトリウム１０．！ｉ’。[Formulation Example 1] Cycloartenol 260Ji', Vitamin 01 [ll
11 Citric acid 5g, cellulose calcium glycolate 20
,! i', sodium lauryl sulfate 10. ! i'.
ポリオキシエチレンモノステアレートｓｙ、メチレンク
ロライド３００−を取り、よく混合攪拌しケン濁液状と
する。これにアエロジル２００〜４００（部品名） １
８０１１加えて混合攪拌後、５０〜６０℃で乾燥し、得
られた塊状物を砕いて吸着末を得る。この吸着末にポリ
ビニルピロリドン、２−メチル−５−ビニルピリジン−
メタアクリル酸・アクリル酸メチルエチル共重合体のよ
うな有機溶媒可溶性結合剤２０１１？：溶かしたクロロ
セン・エタノール溶液３００１ｎｌを加え、練合後、常
法に従いエツクペレツターで造粒、約５０℃で乾燥する
と粘着性のない固形化良好な顆粒を得る（活性成分約５
１％含有）。本品に少量のステアリン酸マグネシウム等
の滑沢剤を加えることによりカプセル自動充填機で２０
０ｍｆｌ硬カプセルに充填することができる。Polyoxyethylene monostearate sy and methylene chloride 300- are taken, mixed well and stirred to form a cloudy liquid. Add Aerosil 200 to 400 (parts name) 1
8011 is added, mixed and stirred, and dried at 50 to 60°C, and the resulting lumps are crushed to obtain an adsorption powder. This adsorbed powder contains polyvinylpyrrolidone, 2-methyl-5-vinylpyridine-
Organic solvent soluble binder such as methacrylic acid/methyl ethyl acrylate copolymer 2011? : Add 3001 nl of the dissolved chlorocene/ethanol solution, knead, and then granulate using an Eck pelleter according to the usual method. Drying at about 50°C solidifies to obtain good granules without stickiness (active ingredients of about 5
(contains 1%). By adding a small amount of lubricant such as magnesium stearate to this product, an automatic capsule filling machine
Can be filled into 0 mfl hard capsules.
〔製剤例２〕
２４−メｆレンジクロアルタノール２６０ｇ’ａ’ナタ
ネ油１２０ ＃ Ｋ溶かし、常法に従ってソフトカプセ
ルに充填した。１カプセル１００■で活性成分６８．４
％含有。[Formulation Example 2] 260 g of 24-mef dichloroartanol was dissolved in 120 #K of 'a' rapeseed oil and filled into soft capsules according to a conventional method. 68.4 active ingredients in 1 capsule 100cm
Contains %.
〔製剤例３〕
５０％ンルビトール水ｉｆ １００ ＴｎｌにＤＫエス
テルＦ １６０ （商品名）とポリソルベート８０２し
た後、蒸貿水で余情５００−とし、再び攪拌して乳剤を
得る。（活性成分を約１０％含有）特許出願人 三共株
式会社
代理人 弁理士樫出庄治[Formulation Example 3] DK Ester F 160 (trade name) and polysorbate 802 were added to 50% lnrbitol water if 100 Tnl, and the mixture was made to a 500% concentration with distilled water and stirred again to obtain an emulsion. (Contains about 10% active ingredient) Patent applicant: Sankyo Co., Ltd. Agent: Patent attorney Shoji Kashide
Claims (1)
２４−メチレンシクロアルタノールである特許請求の範
囲第１項記載の抗脂血剤。[Claims] 1. An antilipemic agent containing trimethylsteroid as a main component. 2. The antilipemic agent according to claim 1, wherein the trimethylsteroid is cycloartenol or 24-methylenecycloartanol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13653582A JPS5927824A (en) | 1982-08-05 | 1982-08-05 | Antilipemic agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13653582A JPS5927824A (en) | 1982-08-05 | 1982-08-05 | Antilipemic agent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS5927824A true JPS5927824A (en) | 1984-02-14 |
Family
ID=15177453
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13653582A Pending JPS5927824A (en) | 1982-08-05 | 1982-08-05 | Antilipemic agent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5927824A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003021610A (en) * | 2001-07-09 | 2003-01-24 | New Cosmos Electric Corp | Odor control device |
| JP2007139580A (en) * | 2005-11-18 | 2007-06-07 | Figaro Eng Inc | Device of generating zero-gas air for gas detection device |
| US7674784B2 (en) | 2004-09-29 | 2010-03-09 | Morinaga Milk Industry Co., Ltd. | Drug and food or drink for improving hyperglycemia |
| US7947669B2 (en) | 2005-09-30 | 2011-05-24 | Morinaga Milk Industry Co., Ltd. | Agent for improving insulin resistance |
-
1982
- 1982-08-05 JP JP13653582A patent/JPS5927824A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003021610A (en) * | 2001-07-09 | 2003-01-24 | New Cosmos Electric Corp | Odor control device |
| US7674784B2 (en) | 2004-09-29 | 2010-03-09 | Morinaga Milk Industry Co., Ltd. | Drug and food or drink for improving hyperglycemia |
| US7947669B2 (en) | 2005-09-30 | 2011-05-24 | Morinaga Milk Industry Co., Ltd. | Agent for improving insulin resistance |
| JP2007139580A (en) * | 2005-11-18 | 2007-06-07 | Figaro Eng Inc | Device of generating zero-gas air for gas detection device |
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