JPH0464556B2 - - Google Patents
Info
- Publication number
- JPH0464556B2 JPH0464556B2 JP59252651A JP25265184A JPH0464556B2 JP H0464556 B2 JPH0464556 B2 JP H0464556B2 JP 59252651 A JP59252651 A JP 59252651A JP 25265184 A JP25265184 A JP 25265184A JP H0464556 B2 JPH0464556 B2 JP H0464556B2
- Authority
- JP
- Japan
- Prior art keywords
- lucioside
- oil
- loofah
- saponin
- antioxidant
- 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.)
- Expired - Lifetime
Links
- 239000003963 antioxidant agent Substances 0.000 claims description 17
- 235000009814 Luffa aegyptiaca Nutrition 0.000 claims description 15
- 230000003078 antioxidant effect Effects 0.000 claims description 13
- 239000001397 quillaja saponaria molina bark Substances 0.000 claims description 13
- 229930182490 saponin Natural products 0.000 claims description 13
- 150000007949 saponins Chemical class 0.000 claims description 13
- 239000004480 active ingredient Substances 0.000 claims description 3
- 238000000605 extraction Methods 0.000 claims description 2
- 244000280244 Luffa acutangula Species 0.000 claims 2
- 235000006708 antioxidants Nutrition 0.000 description 15
- 244000302544 Luffa aegyptiaca Species 0.000 description 13
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 12
- 150000008505 β-D-glucopyranosides Chemical class 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- 229930003427 Vitamin E Natural products 0.000 description 6
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019165 vitamin E Nutrition 0.000 description 6
- 229940046009 vitamin E Drugs 0.000 description 6
- 239000011709 vitamin E Substances 0.000 description 6
- 239000004359 castor oil Substances 0.000 description 3
- FMMOOAYVCKXGMF-MURFETPASA-N ethyl linoleate Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(=O)OCC FMMOOAYVCKXGMF-MURFETPASA-N 0.000 description 3
- 229940031016 ethyl linoleate Drugs 0.000 description 3
- FMMOOAYVCKXGMF-UHFFFAOYSA-N linoleic acid ethyl ester Natural products CCCCCC=CCC=CCCCCCCCC(=O)OCC FMMOOAYVCKXGMF-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 235000014593 oils and fats Nutrition 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000010495 camellia oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- PWAOOJDMFUQOKB-WCZZMFLVSA-N ginsenoside Re Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@H]1[C@H](O[C@@H]2[C@H]3C(C)(C)[C@@H](O)CC[C@]3(C)[C@@H]3[C@@]([C@@]4(CC[C@@H]([C@H]4[C@H](O)C3)[C@](C)(CCC=C(C)C)O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)C)(C)C2)O[C@H](CO)[C@@H](O)[C@@H]1O PWAOOJDMFUQOKB-WCZZMFLVSA-N 0.000 description 2
- YURJSTAIMNSZAE-HHNZYBFYSA-N ginsenoside Rg1 Chemical compound O([C@@](C)(CCC=C(C)C)[C@@H]1[C@@H]2[C@@]([C@@]3(C[C@@H]([C@H]4C(C)(C)[C@@H](O)CC[C@]4(C)[C@H]3C[C@H]2O)O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)C)(C)CC1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O YURJSTAIMNSZAE-HHNZYBFYSA-N 0.000 description 2
- AOGZLQUEBLOQCI-UHFFFAOYSA-N ginsenoside-Re Natural products CC1OC(OCC2OC(OC3CC4(C)C(CC(O)C5C(CCC45C)C(C)(CCC=C(C)C)OC6OC(CO)C(O)C(O)C6O)C7(C)CCC(O)C(C)(C)C37)C(O)C(O)C2O)C(O)C(O)C1O AOGZLQUEBLOQCI-UHFFFAOYSA-N 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
- 238000000034 method Methods 0.000 description 2
- 239000004006 olive oil Substances 0.000 description 2
- 235000008390 olive oil Nutrition 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 235000019485 Safflower oil Nutrition 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000008163 avocado oil Substances 0.000 description 1
- 235000021302 avocado oil Nutrition 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 235000013365 dairy product Nutrition 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000008157 edible vegetable oil Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000008524 evening primrose extract Nutrition 0.000 description 1
- 239000010475 evening primrose oil Substances 0.000 description 1
- 229940089020 evening primrose oil Drugs 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 235000013310 margarine Nutrition 0.000 description 1
- 239000003264 margarine Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000013622 meat product Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 235000013324 preserved food Nutrition 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- 235000014102 seafood Nutrition 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 235000014214 soft drink Nutrition 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 150000003712 vitamin E derivatives Chemical class 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 239000010497 wheat germ oil Substances 0.000 description 1
Landscapes
- Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
- Edible Oils And Fats (AREA)
- Saccharide Compounds (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Fats And Perfumes (AREA)
Description
［産業上の利用分野］
本発明は酸化防止剤、とくに油脂類や不飽和結
合を有し酸敗を受けやすい油に適当される酸化防
止剤に関するものである。
［従来の技術］
従来、オリーブ油やヒマシ油などの油脂類ある
いは不飽和結合を有し酸敗を受けやすい油には保
存安定性向上の目的で抗酸化能を供えた酸化防止
剤が配合されているが、BHTやBHAなどの合成
酸化防止剤はとくに安全性の見地からこれらの使
用に対しては再検討が加えられているのが現状で
ある。
このような背景から、天然の酸化防止剤とてビ
タミンＥの需要が高まつてきているが、その供給
源、基剤への溶解性、価格などには問題があり、
新しい天然酸化防止剤の開発が強く要望されてい
る。
［発明が解決しようとする問題点］
本発明者らは上記事情にかんがみ鋭意検討した
結果、ヘチマから抽出して得られるサポニンにビ
タミンＥと比較して優るとも劣らない優れた抗酸
化能があることを見いだし、この知見にもとづい
て本発明を完成するに至つた。
［問題点を解決するための手段］
すなわち、本発明はヘチマから抽出して得られ
るサポニンを有効成分とする酸化防止剤である。
以下、本発明の構成について詳述する。
本発明で用いるヘチマから抽出して得られるサ
ポニン（以下、ヘチマサポニンという）はヘチマ
の地上部もしくは地下部を溶媒、たとえば水、低
級アルコール、含水低級アルコールなどで抽出し
て得られる。上記抽出液は濃縮した後、吸着法や
分配法を用いて精製し、さらに低級アルコールな
どの水溶性溶媒中に溶解してからエーテルやｎ−
ヘキサンなどの脂溶性溶媒中に添加し、析出物と
して回収すれば純度の高いヘチマサポニンとして
得られる。
上記ヘチマサポニンの主有効成分は、下記構造
式で示されるルシオシドＡ、ルシオシドＢ、ルシ
オシドＣ、ルシオシドＤ、ルシオシドＥ、ルシオ
シドＦ、ルシオシドＧ、ルシオシドＨ、ルシオシ
ドＩであり、このほかにギンゼノシドRe、ギン
ゼノシドRg1が含まれることが知られており、
個々のルシオシドについては特願昭58−155552号
にて構造が明らかにされている。また、ギンゼノ
シドRe、ギンゼノシドRg1は既知の物質である。
ルシオシドＡ；R1＝CH2OH、R2＝β−Ｄ−グル
コピラノシド、R3＝OH、R4＝Ｈ
ルシオシドＢ；R1＝CH2OH、R2＝β−Ｄ−グル
コピラノシド、R3＝Ｈ、R4＝OH
ルシオシドＣ；R1＝CH3、R2＝β−Ｄ−グルコ
ピラノシド、R3＝OH、R4＝Ｈ
ルシオシドＤ；R1＝CHO、R2＝β−Ｄ−グルコ
ピラノシド、R3＝Ｈ、R4＝OH
ルシオシドＥ；R1＝CH2OH、R2＝β−Ｄ−グル
コピラノシド、R3＝Ｈ、R4＝Ｈ
ルシオシドＦ；R1＝CHO、R2＝β−Ｄ−グルコ
ピラノシド、R3＝Ｈ、R4＝Ｈ
ルシオシドＧ；R1＝CH3、R2＝β−Ｄ−グルコ
ピラノシド、R3＝Ｈ、R4＝OH
ルシオシドＨ；R1＝CH3、R2＝β−Ｄ−グルコ
ピラノシド、R3＝Ｈ、R4＝Ｈ
ルシオシドＩ；R1＝CH2OH、R2＝Ｈ、R4＝OH
上記した個々のルシオシドはヘチマサポニンを
シリカゲルクロマトグラフイーなどを用いて分画
すれば単離することができる。当然のことながら
本発明においてはこうして得られたルシオシドを
単体で用いてもよい。
ヘチマサポニンも個々のルシオシドも少量の低
級アルコールに溶解することによつて、水中にも
油中にも自由に溶解させることが可能であり、ビ
タミンＥに比較して応用範囲が広い。
ヘチマサポニン、ルシオシドＡ、ルシオシド
Ｂ、ルシオシドＣ、ルシオシドＤ、ルシオシド
Ｅ、ルシオシドＦ、ルシオシドＧ、ルシオシド
Ｈ、ルシオシドＩの一種又は二種以上の配合量は
油脂に対して0.001〜５重量％、好ましくは１〜
２重量％である。
本発明の酸化防止剤は酸敗を受けやすいオリー
ブ油、ヒマシ油、椿油、茶実油、アボガド油、ゴ
マ油、綿実油、小麦胚芽油、ヒマワリ油、大豆
油、サフラワ油、月見草油、メドフオームなどの
油脂類やリノール酸、リノレイン酸、オレイン酸
などの不飽和脂肪酸およびそのエステルあるいは
不飽和アルコールなどの不飽和結合を有する油な
どに対して使用されるが、これら油脂類、油類が
水系または油系を問わず各種の食料品、たとえば
食用油、乳製品、マーガリン、ラード、肉製品、
罐詰類、魚介類、インスタント食品、菓子、清涼
飲料水のほか塗料、絵具、医薬品、化粧品などに
配合される形で用いられても効果を発揮する。
［発明の効果］
本発明の酸化防止剤は、天然起源の酸化防止剤
であり、安全性に関する危惧もなく、従来の天然
酸化防止剤であるビタミンＥより安い価格で入手
することが期待でき、かつ供給もヘチマの栽培に
より解決できる。
さらに、ヘチマサポニンも個々のルシオシドも
少量の低級アルコールに溶解することによつて、
水中にも油中にも自由に溶解させることが可能で
あり、ビタミンＥに比較して応用範囲が広い。
また、抗酸化能もビタミンＥに比較して優ると
も劣らない優れたものである。
［実施例］
つぎに実施例により本発明をさらに詳細に説明
する。
実施例 １
リノール酸エチル（日本油脂製）10ｇ中にエタ
ノール0.2ｇに溶解したヘチマサポニン（0.6mg、
２mgまたは５mg）を添加、溶解する。このものを
50℃恒温槽中で３日または６日保存後、油化学法
に準じて過酸化物価（POV）を測定した。
対照としては、ヘチマサポニン無添加のリノー
ル酸エチルおよびとミツクストコフエロール（ビ
タミンＥ同族体、エーザイ製）２mgを添加したリ
ノール酸エチルを用いた。
結果を表−１に示す。
[Industrial Application Field] The present invention relates to an antioxidant, particularly an antioxidant suitable for oils and fats and oils having unsaturated bonds and susceptible to rancidity. [Prior Art] Conventionally, oils and fats such as olive oil and castor oil, or oils that have unsaturated bonds and are susceptible to rancidity, have been blended with antioxidants that have antioxidant ability for the purpose of improving storage stability. However, the current situation is that the use of synthetic antioxidants such as BHT and BHA is being reconsidered, especially from a safety standpoint. Against this background, demand for vitamin E as a natural antioxidant is increasing, but there are problems with its source, solubility in base materials, price, etc.
There is a strong need for the development of new natural antioxidants. [Problems to be Solved by the Invention] The present inventors have made extensive studies in view of the above circumstances, and have found that saponin extracted from loofah has an excellent antioxidant ability that is comparable to that of vitamin E. Based on this finding, we have completed the present invention. [Means for Solving the Problems] That is, the present invention is an antioxidant containing saponin extracted from loofah as an active ingredient. Hereinafter, the configuration of the present invention will be explained in detail. Saponin obtained by extraction from loofah used in the present invention (hereinafter referred to as loofah saponin) is obtained by extracting the above-ground or underground parts of loofah with a solvent such as water, lower alcohol, hydrous lower alcohol, etc. After the above extract is concentrated, it is purified using an adsorption method or a distribution method, and then dissolved in a water-soluble solvent such as a lower alcohol, and then ether or n-
If it is added to a fat-soluble solvent such as hexane and collected as a precipitate, highly pure loofah saponin can be obtained. The main active ingredients of the loofah saponin are lucioside A, lucioside B, lucioside C, lucioside D, lucioside E, lucioside F, lucioside G, lucioside H, and lucioside I, which are shown by the following structural formula, and in addition, ginsenoside Re, It is known to contain ginsenoside Rg 1 ,
The structures of individual luciosides have been disclosed in Japanese Patent Application No. 155552/1983. Furthermore, ginsenoside Re and ginsenoside Rg 1 are known substances. Lucioside A; R 1 = CH 2 OH, R 2 = β-D-glucopyranoside, R 3 = OH, R 4 = H Lucioside B; R 1 = CH 2 OH, R 2 = β-D-glucopyranoside, R 3 = H, R 4 = OH Lucioside C; R 1 = CH 3 , R 2 = β-D-glucopyranoside, R 3 = OH, R 4 = H Lucioside D; R 1 = CHO, R 2 = β-D-glucopyranoside, R 3 = H, R 4 = OH Lucioside E; R 1 = CH 2 OH, R 2 = β-D-glucopyranoside, R 3 = H, R 4 = H Lucioside F; R 1 = CHO, R 2 = β- D-glucopyranoside, R 3 = H, R 4 = H Lucioside G; R 1 = CH 3 , R 2 = β-D-glucopyranoside, R 3 = H, R 4 = OH Lucioside H; R 1 = CH 3 , R 2 = β-D-glucopyranoside, R 3 = H, R 4 = H Lucioside I; R 1 = CH 2 OH, R 2 = H, R 4 = OH. It can be isolated by fractionation using Naturally, in the present invention, the lucioside thus obtained may be used alone. By dissolving loofah saponin and individual luciosides in a small amount of lower alcohol, they can be freely dissolved in both water and oil, and have a wider range of applications than vitamin E. The blending amount of one or more of Hetimasaponin, Lucioside A, Lucioside B, Lucioside C, Lucioside D, Lucioside E, Lucioside F, Lucioside G, Lucioside H, and Lucioside I is preferably 0.001 to 5% by weight based on the fat and oil. is 1~
It is 2% by weight. The antioxidants of the present invention are oils and fats that are susceptible to rancidity, such as olive oil, castor oil, camellia oil, tea seed oil, avocado oil, sesame oil, cottonseed oil, wheat germ oil, sunflower oil, soybean oil, safflower oil, evening primrose oil, and medfoam. It is used for unsaturated fatty acids such as linoleic acid, linoleic acid, and oleic acid, their esters, and oils with unsaturated bonds such as unsaturated alcohols. All kinds of food products, such as edible oil, dairy products, margarine, lard, meat products,
It is effective when used in canned foods, seafood, instant foods, confectionery, soft drinks, as well as paints, pigments, medicines, cosmetics, etc. [Effects of the Invention] The antioxidant of the present invention is an antioxidant of natural origin, has no safety concerns, and can be expected to be obtained at a lower price than vitamin E, which is a conventional natural antioxidant. Moreover, the problem of supply can be solved by cultivating loofah. Furthermore, by dissolving both loofah saponin and individual luciosides in a small amount of lower alcohol,
It can be freely dissolved in both water and oil, and has a wider range of applications than vitamin E. In addition, its antioxidant ability is as good as that of vitamin E. [Example] Next, the present invention will be explained in more detail with reference to Examples. Example 1 Loofa saponin (0.6 mg,
2mg or 5mg) and dissolve. this thing
After storage for 3 or 6 days in a constant temperature bath at 50°C, the peroxide value (POV) was measured according to the oil chemistry method. As a control, ethyl linoleate without the addition of loofah saponin and ethyl linoleate to which 2 mg of tomicostocopherol (vitamin E analogue, manufactured by Eisai) were added were used. The results are shown in Table-1.
【表】【table】
【表】
表−１から明らかなごとく、ヘチマサポニン
60ppm添加とほぼ同程度の抗酸化能がある。
実施例 ２
実施例１と同様、リノール酸エチル10ｇ中にエ
タノール0.07ｇに溶解したルシオシド２mgを添加
溶解して過酸化物価（POV）を測定した。
結果を表−２に示す。[Table] As is clear from Table 1, loofah saponin
It has almost the same antioxidant ability as 60ppm addition. Example 2 In the same manner as in Example 1, 2 mg of lucioside dissolved in 0.07 g of ethanol was added and dissolved in 10 g of ethyl linoleate, and the peroxide value (POV) was measured. The results are shown in Table-2.
Claims (1)
成分とする酸化防止剤。 ２ ヘチマから抽出して得られるサポニンがルシ
オシドＡ、ルシオシドＢ、ルシオシドＣ、ルシオ
シドＤ、ルシオシドＥ、ルシオシドＦ、ルシオシ
ドＧ、ルシオシドＨ、ルシオシドＩよりなる群か
ら選ばれた一種又は二種以上である特許請求の範
囲第１項記載の酸化防止剤。[Claims] 1. An antioxidant containing saponin extracted from loofah as an active ingredient. 2 The saponin obtained by extraction from loofah is one or more selected from the group consisting of lucioside A, lucioside B, lucioside C, lucioside D, lucioside E, lucioside F, lucioside G, lucioside H, and lucioside I. The antioxidant according to claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59252651A JPS61130390A (en) | 1984-11-29 | 1984-11-29 | Autioxidant |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59252651A JPS61130390A (en) | 1984-11-29 | 1984-11-29 | Autioxidant |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61130390A JPS61130390A (en) | 1986-06-18 |
| JPH0464556B2 true JPH0464556B2 (en) | 1992-10-15 |
Family
ID=17240318
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59252651A Granted JPS61130390A (en) | 1984-11-29 | 1984-11-29 | Autioxidant |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61130390A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011032239A (en) * | 2009-08-04 | 2011-02-17 | Kanei:Kk | Cooler composition containing loofah saponin content fraction and cooler food containing the same |
-
1984
- 1984-11-29 JP JP59252651A patent/JPS61130390A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61130390A (en) | 1986-06-18 |
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