JPS6366125A - Anticancer agent - Google Patents
Anticancer agentInfo
- Publication number
- JPS6366125A JPS6366125A JP61209577A JP20957786A JPS6366125A JP S6366125 A JPS6366125 A JP S6366125A JP 61209577 A JP61209577 A JP 61209577A JP 20957786 A JP20957786 A JP 20957786A JP S6366125 A JPS6366125 A JP S6366125A
- Authority
- JP
- Japan
- Prior art keywords
- fatty acid
- lanolin fatty
- melting point
- purified
- lanolin
- 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
- 239000002246 antineoplastic agent Substances 0.000 title claims abstract description 17
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 51
- 239000000194 fatty acid Substances 0.000 claims abstract description 51
- 229930195729 fatty acid Natural products 0.000 claims abstract description 51
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 50
- 239000004166 Lanolin Substances 0.000 claims abstract description 44
- 229940039717 lanolin Drugs 0.000 claims abstract description 44
- 235000019388 lanolin Nutrition 0.000 claims abstract description 44
- 238000002844 melting Methods 0.000 claims abstract description 13
- 230000008018 melting Effects 0.000 claims abstract description 13
- 210000002268 wool Anatomy 0.000 claims abstract description 6
- 239000004480 active ingredient Substances 0.000 claims abstract description 4
- 229940041181 antineoplastic drug Drugs 0.000 claims description 5
- 230000001093 anti-cancer Effects 0.000 abstract description 10
- 230000000694 effects Effects 0.000 abstract description 10
- 238000000034 method Methods 0.000 abstract description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract description 4
- 239000003795 chemical substances by application Substances 0.000 abstract description 3
- 150000002632 lipids Chemical class 0.000 abstract description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003513 alkali Substances 0.000 abstract description 2
- 238000007796 conventional method Methods 0.000 abstract description 2
- 239000000741 silica gel Substances 0.000 abstract description 2
- 229910002027 silica gel Inorganic materials 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract description 2
- 238000001256 steam distillation Methods 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract 2
- 230000001877 deodorizing effect Effects 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 description 6
- 206010028980 Neoplasm Diseases 0.000 description 5
- 241000699666 Mus <mouse, genus> Species 0.000 description 4
- 201000011510 cancer Diseases 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 210000000683 abdominal cavity Anatomy 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 206010039491 Sarcoma Diseases 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000340 anti-metabolite Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 229940100197 antimetabolite Drugs 0.000 description 1
- 239000002256 antimetabolite Substances 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 210000004209 hair Anatomy 0.000 description 1
- -1 hydroxy fatty acids Chemical class 0.000 description 1
- 230000003308 immunostimulating effect Effects 0.000 description 1
- 238000012844 infrared spectroscopy analysis Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 239000008055 phosphate buffer solution Substances 0.000 description 1
- 239000000419 plant extract Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 210000002374 sebum Anatomy 0.000 description 1
- 125000005480 straight-chain fatty acid group Chemical group 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
Landscapes
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は制癌剤に関し、更に詳細にはラノリン脂肪酸を
主成分とする制癌剤に関する。DETAILED DESCRIPTION OF THE INVENTION (Industrial Field of Application) The present invention relates to an anticancer agent, and more particularly to an anticancer agent containing lanolin fatty acid as a main component.
（従来の技術）
従来、癌の化学線Ｖ；剤としては、アルキル化剤代謝拮
抗剤、抗生物質及び植物アルカロイド剤等が製剤されて
いる。また、最近では、ある種の植物エキスに免疫賦活
作用があることがわかり抗癌剤として実用化されている
。(Prior Art) Conventionally, alkylating agents, antimetabolites, antibiotics, plant alkaloids, and the like have been formulated as actinic radiation V agents for cancer. Furthermore, recently, certain plant extracts have been found to have immunostimulatory effects, and have been put to practical use as anticancer agents.
（発明が解決しようとする問題点）
上述のように多くの種類の制癌剤が製剤されてきた６ま
たいろいろと制癌について提案がされて来たが、いずれ
の制癌剤及び制癌についての提案も制癌効果が強いもの
は、副作用が強く、実際の使用面で多大の制約があり、
低毒性で優れた制癌活性を有する制癌剤を開発すること
が強く望まれている。(Problems to be Solved by the Invention) As mentioned above, many types of anti-cancer drugs have been formulated6 and various proposals have been made for anti-cancer drugs, but none of the anti-cancer drugs and proposals for anti-cancer drugs have been developed. Drugs with strong cancer effects have strong side effects, and there are many restrictions on their actual use.
There is a strong desire to develop anticancer agents with low toxicity and excellent anticancer activity.
本発明は強い制癌活性を有し、しかもｎＪＨの低い制癌
剤を提供することにある。The object of the present invention is to provide an anticancer agent that has strong anticancer activity and low nJH.
（問題点を解決するための手段）
本発明は上記目的を遂行すべく研究した結果、ラノリン
脂肪酸は制癌剤として有効で、かつ副作用がきわめて低
いとの知見を得て本発明を完成した。(Means for Solving the Problems) As a result of research to achieve the above-mentioned object, the present invention was completed based on the knowledge that lanolin fatty acids are effective as anticancer agents and have extremely low side effects.
ラノリン脂肪酸はη毛脂質を原着１どしこれを精製した
脂肪酸であって、直鎖脂肪酸の含（ｒにが少なく（全体
の約７重量％）、イソ脂肪酸、アンチイソ脂肪酸などの
分枝脂肪酸が全体の約２／３を 。Lanolin fatty acid is a fatty acid obtained by depositing η hair lipids and refining them, and contains a small amount of straight chain fatty acids (about 7% by weight of the total) and branched fatty acids such as isofatty acids and antiisofatty acids. accounts for about 2/3 of the total.
占め、その他ヒドロキシ脂肪酸を全体の約１／３を含ん
でおり、多量の分枝脂肪酸を含有する点で人間の皮脂に
類似した組成と機能を有することに注目し、まず該ラノ
リン酸脂肪酸の制癌効果を予備試験した結果、かなり強
い制癌効果のあることの知見を得て本発明を完成した。Noting that it has a composition and function similar to human sebum in that it contains a large amount of branched fatty acids, and contains about 1/3 of other hydroxy fatty acids, we first investigated the control of lanolin fatty acids. As a result of preliminary tests on cancer effect, the present invention was completed based on the knowledge that it has a fairly strong anti-cancer effect.
（構成）
本発明の要旨は羊毛脂から得られるラノリン脂肪酸を有
効成分とする制癌剤である。(Structure) The gist of the present invention is an anticancer agent containing lanolin fatty acid obtained from wool fat as an active ingredient.
精製ラノリン脂肪酸は、羊毛脂を常法に従って、アルカ
リでけん化分解してラノリンアルコールとラノリン脂肪
酸に分け、このうちラノリン脂肪酸を通常の脱色および
水蒸気蒸留法により脱臭して精製ラノリン脂肪酸を得る
。Purified lanolin fatty acids are obtained by saponifying and decomposing wool fat with an alkali to separate it into lanolin alcohol and lanolin fatty acids according to a conventional method, and of these, the lanolin fatty acids are deodorized by conventional decolorization and steam distillation methods to obtain purified lanolin fatty acids.
このようにして得た精製う゛ノリン脂肪酸はそのまま用
いてもよいが、また、融点の違いによって、例えば低融
点部（５０℃未満）、中間部（５０〜７０℃）および高
融点部（７０℃を超えるもの）に分画したものを用いて
もよい。このさい、低融点部のものは高融点部に比して
制癌力が強い。The purified vinolinic fatty acid obtained in this way may be used as it is, but due to the difference in melting point, for example, a low melting point part (less than 50°C), an intermediate part (50 to 70°C) and a high melting point part (70°C). (exceeding) may be used. In this case, the low melting point part has stronger anticancer power than the high melting point part.
また、精製ラノリン脂肪酸を例えばシリカゲルカラムに
ヘキサン、クロロホルム、メタノール等の極性の異なる
溶媒を用いて低極性フラクション、中極性フラクション
及び高極性フラクションに分画し、それぞれを一種以上
用いてもよい。Alternatively, purified lanolin fatty acids may be fractionated into a low polarity fraction, a medium polarity fraction, and a high polarity fraction using a silica gel column using solvents of different polarity such as hexane, chloroform, methanol, etc., and one or more of each may be used.
本発明に用いるラノリン脂肪酸は、そのまま乳剤、錠剤
、溶液など任意の形態で投与できる。投与方法は経口及
び非経口投与があるが、患部に直接注射などで投与する
のが好ましい。投与斌は対象となる癌の種類、症状、投
与方法などにより異なるが、５〜４００ｍｇ／ｋｇ／
Ｅｌの範囲で用いるのが望ましい。The lanolin fatty acid used in the present invention can be administered as it is in any form such as an emulsion, tablet, or solution. Administration methods include oral and parenteral administration, but direct injection into the affected area is preferred. The dosage varies depending on the type of cancer, symptoms, administration method, etc., but it is 5 to 400 mg/kg/
It is desirable to use it within the range of El.
（発明の効果）
本発明の制癌剤はマウスの多くの癌に優れた効果を有し
ており、しかも人間を含めた動物体内に存在する分枝脂
肪酸が主成分であるため重大な副作用は示さない。(Effect of the invention) The anticancer agent of the present invention has excellent effects on many cancers in mice, and does not show any serious side effects because its main component is branched fatty acids that exist in the bodies of animals including humans. .
（実施例） ４一 本発明をその実施例につき説明する。(Example) 41 The invention will now be described with reference to its embodiments.
抗癌活性の測定は下記のように行った。Anticancer activity was measured as follows.
（イ）投与ラノリン脂肪酸乳化液の調製方法試験に供す
るラノリン脂肪酸２００■ｇを試験管にとり、下記ａ
ｆｔ ５ ｍ ｍ を加え８０℃湯浴で超音波を３０
秒間かけ、得られた混合液にｂ液５ｍＱ を加えて薬剤
とした。(b) Method for preparing lanolin fatty acid emulsion for administration Place 200 g of lanolin fatty acid to be tested in a test tube, and
ft.
5 mQ of solution B was added to the resulting mixed solution to prepare a drug.
ａ液：水素化ヒマシ油エチレンオキサイド付加物（日興
ケミカル株式会社製：商品名ＨＣＯ−６０）を ０．４
重量％になるようにリン酸緩衝液（２倍濃度）に溶かし
たもの。Liquid a: Hydrogenated castor oil ethylene oxide adduct (manufactured by Nikko Chemical Co., Ltd.: trade name HCO-60) at 0.4
Dissolved in phosphate buffer (double concentration) to % by weight.
ｂ液：水素化ヒマシ油を ０．４重量％になるようにリ
ン酸緩衝溶液（２倍濃度）に溶かしたもの。Solution B: Hydrogenated castor oil was dissolved in a phosphate buffer solution (double concentration) to a concentration of 0.4% by weight.
（ロ）薬剤の投与方法
マウスの腹腔に（イ）の方法で調製したラノリン脂肪酸
乳化液を０．２５履Ａ／日／マウスにて毎日１回ずつ５
日連続投与した。(b) Method of drug administration: Administer the lanolin fatty acid emulsion prepared by method (a) into the abdominal cavity of the mouse at 0.25 lA/day/mouse once daily for 50 minutes.
Administered continuously for days.
（ハ）マウスの選定 マウスの使用数は１群を５〜１０匹とした。(c) Mouse selection The number of mice used was 5 to 10 per group.
実施例１
精製ラノリン脂肪酸を融点の違いによって分画して得た
ラノリン脂肪酸Ｌ、ラノリン脂肪酸Ｍ及びラノリン脂肪
酸Ｈの乳化液を（イ）の投与ラノリン脂肪酸乳化液の調
製方法によって調製し、Ｓ−１８０（肉腫）を腹腔に２
Ｘ １０’個移植したマウス（ＩＣＲ＞に、移植後た
だちに」１記乳化液を（ロ）の方法で腹腔内に直接注入
投与した。その結果を表−１に、またラノリン脂肪酸り
、Ｍ及びＨの分析値及び融点を表−２に示す。また、図
−１には、ラノリン脂肪酸りのガスクロマトグラフを、
さらに図−２には該ラノリン脂肪酸りの赤外分光分析図
を示す。Example 1 An emulsion of lanolin fatty acid L, lanolin fatty acid M, and lanolin fatty acid H obtained by fractionating purified lanolin fatty acids according to their melting points was prepared by the method for preparing a lanolin fatty acid emulsion in (a), and S- 180 (sarcoma) in the abdominal cavity 2
Immediately after the transplantation, the emulsion described in 1 was directly injected into the abdominal cavity of the mouse (ICR) in which 10' x 10' mice had been transplanted.The results are shown in Table 1. The analytical values and melting point of H are shown in Table 2. In addition, Figure 1 shows the gas chromatograph of lanolin fatty acid.
Furthermore, FIG. 2 shows an infrared spectroscopy diagram of the lanolin fatty acid.
ガスクロマトグラフは下記仕様のものを下記条件で行な
った。A gas chromatograph with the following specifications was used under the following conditions.
カラム： Ｃａｒｂｏｗａｘ ２０Ｍ ３０ｍＸ０．２
５ｍｍφカラム温度＝１８０→２２０℃（５℃／５ｕｎ
）スプリット比： １／１００
キャリヤーガス：Ｈｅ １ｍ Ｑ ／＋ｉｎ表−１の結
果から明らかなように、ここで実験したラノリン脂肪酸
はいずれも強い制癌活性を示したが、中でもラノリン脂
肪酸りは、特に強い活性を持つ事が判った。Column: Carbowax 20M 30mX0.2
5mmφ column temperature = 180 → 220℃ (5℃/5un
) Split ratio: 1/100 Carrier gas: He 1m Q /+in As is clear from the results in Table 1, all of the lanolin fatty acids tested here showed strong anticancer activity, but especially lanolin fatty acids, It was found to have particularly strong activity.
実施例２
実施例１で用いたラノリン脂肪酸について、シリカゲル
カラムを用いヘキサン、クロロフォルム、メタノールの
溶媒を順に流し分画して得られた低極性フラクション（
ラノリン脂肪酸Ｆｒ、１という）、中極性フラクション
（ラノリン脂肪酸Ｆｒ、 ２ ） 及び高極性フラク
ション（ラノリン脂肪酸Ｆｒ、３）の３つのフラクショ
ンについて実施例１に準じて試験し制癌作用がどのフラ
クションで強く現れるかをみた。その結果を表−３に示
す。Example 2 Regarding the lanolin fatty acid used in Example 1, a low polar fraction (
Three fractions, lanolin fatty acid Fr, 1), a medium polar fraction (lanolin fatty acid Fr, 2), and a highly polar fraction (lanolin fatty acid Fr, 3) were tested according to Example 1 to determine which fraction had the strongest anticancer effect. I looked to see if he would show up. The results are shown in Table-3.
表−３の結果から明らかなように、ラノリン脂肪酸およ
びそれらを極性の違いにより分画したものはいずれも制
癌活性に優れており、低極性フラクション（ラノリン脂
肪酸Ｆｒ−１）は特に活性が高いことが認められる。As is clear from the results in Table 3, lanolin fatty acids and their fractions based on polarity have excellent anticancer activity, and the low polarity fraction (lanolin fatty acid Fr-1) has particularly high activity. It is recognized that
図−１は実施例１で用いたラノリン脂肪酸りのガスクロ
マトグラフィー分析結果であり１図−２はその赤外分光
分析図である。Figure 1 shows the results of gas chromatography analysis of the lanolin fatty acid used in Example 1, and Figure 1 and 2 show its infrared spectroscopic analysis.
Claims (3)
分とする制癌剤。(1) An anticancer drug whose active ingredient is purified lanolin fatty acid made from wool fat.
が融点によつて分画したラノリン脂肪酸である制癌剤。(2) The anticancer agent according to claim 1, wherein the lanolin fatty acid is a lanolin fatty acid fractionated by melting point.
極性の違いにより分画して得たラノリン脂肪酸である制
癌剤。(3) The anticancer agent set forth in claim 1, which is a lanolin fatty acid obtained by fractionating lanolin fatty acids depending on their polarity.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61209577A JPS6366125A (en) | 1986-09-08 | 1986-09-08 | Anticancer agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61209577A JPS6366125A (en) | 1986-09-08 | 1986-09-08 | Anticancer agent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6366125A true JPS6366125A (en) | 1988-03-24 |
Family
ID=16575136
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61209577A Pending JPS6366125A (en) | 1986-09-08 | 1986-09-08 | Anticancer agent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6366125A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998030532A1 (en) * | 1997-01-14 | 1998-07-16 | Croda International Plc | Woolgrease |
| JP2010514565A (en) * | 2007-01-03 | 2010-05-06 | ホソン インダストリアル ディベロップメント カンパニー リミテッド | Ceramic filter assembly and assembling method thereof |
| US7976830B2 (en) | 2000-03-29 | 2011-07-12 | Croda, Inc. | Fatty quat based on ante-iso compounds |
-
1986
- 1986-09-08 JP JP61209577A patent/JPS6366125A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998030532A1 (en) * | 1997-01-14 | 1998-07-16 | Croda International Plc | Woolgrease |
| GB2336365A (en) * | 1997-01-14 | 1999-10-20 | Croda Int Plc | Woolgrease |
| GB2336365B (en) * | 1997-01-14 | 2000-09-06 | Croda Int Plc | Woolgrease |
| US7976830B2 (en) | 2000-03-29 | 2011-07-12 | Croda, Inc. | Fatty quat based on ante-iso compounds |
| JP2010514565A (en) * | 2007-01-03 | 2010-05-06 | ホソン インダストリアル ディベロップメント カンパニー リミテッド | Ceramic filter assembly and assembling method thereof |
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