JPH03100093A - Antioxidant - Google Patents
AntioxidantInfo
- Publication number
- JPH03100093A JPH03100093A JP23752889A JP23752889A JPH03100093A JP H03100093 A JPH03100093 A JP H03100093A JP 23752889 A JP23752889 A JP 23752889A JP 23752889 A JP23752889 A JP 23752889A JP H03100093 A JPH03100093 A JP H03100093A
- Authority
- JP
- Japan
- Prior art keywords
- antioxidant
- callus
- anise
- polar solvent
- extracted
- 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
- 239000003963 antioxidant agent Substances 0.000 title claims abstract description 27
- 230000003078 antioxidant effect Effects 0.000 title claims abstract description 22
- 206010020649 Hyperkeratosis Diseases 0.000 claims abstract description 25
- 235000007265 Myrrhis odorata Nutrition 0.000 claims abstract description 16
- 235000012550 Pimpinella anisum Nutrition 0.000 claims abstract description 16
- 239000002798 polar solvent Substances 0.000 claims abstract description 8
- 239000000126 substance Substances 0.000 claims abstract 6
- 240000009023 Myrrhis odorata Species 0.000 claims abstract 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 34
- 235000013305 food Nutrition 0.000 abstract description 8
- 235000013599 spices Nutrition 0.000 abstract description 8
- 241000196324 Embryophyta Species 0.000 abstract description 5
- 239000000796 flavoring agent Substances 0.000 abstract description 4
- 235000019634 flavors Nutrition 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 3
- 230000003647 oxidation Effects 0.000 abstract description 3
- 238000007254 oxidation reaction Methods 0.000 abstract description 3
- 239000000470 constituent Substances 0.000 abstract 2
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 abstract 1
- 235000006708 antioxidants Nutrition 0.000 description 18
- 240000004760 Pimpinella anisum Species 0.000 description 14
- 239000000284 extract Substances 0.000 description 12
- 235000019441 ethanol Nutrition 0.000 description 11
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 3
- NJYFRQQXXXRJHK-UHFFFAOYSA-N (4-aminophenyl) thiocyanate Chemical compound NC1=CC=C(SC#N)C=C1 NJYFRQQXXXRJHK-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229920002148 Gellan gum Polymers 0.000 description 2
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 2
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000216 gellan gum Substances 0.000 description 2
- 235000010492 gellan gum Nutrition 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 2
- 235000020778 linoleic acid Nutrition 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- PRPINYUDVPFIRX-UHFFFAOYSA-N 1-naphthaleneacetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CC=CC2=C1 PRPINYUDVPFIRX-UHFFFAOYSA-N 0.000 description 1
- SPSPIUSUWPLVKD-UHFFFAOYSA-N 2,3-dibutyl-6-methylphenol Chemical compound CCCCC1=CC=C(C)C(O)=C1CCCC SPSPIUSUWPLVKD-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- FAIXYKHYOGVFKA-UHFFFAOYSA-N Kinetin Natural products N=1C=NC=2N=CNC=2C=1N(C)C1=CC=CO1 FAIXYKHYOGVFKA-UHFFFAOYSA-N 0.000 description 1
- 235000013628 Lantana involucrata Nutrition 0.000 description 1
- 235000006677 Monarda citriodora ssp. austromontana Nutrition 0.000 description 1
- 235000009421 Myristica fragrans Nutrition 0.000 description 1
- 235000010676 Ocimum basilicum Nutrition 0.000 description 1
- 240000007926 Ocimum gratissimum Species 0.000 description 1
- 240000007673 Origanum vulgare Species 0.000 description 1
- 244000178231 Rosmarinus officinalis Species 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 240000002657 Thymus vulgaris Species 0.000 description 1
- 235000007303 Thymus vulgaris Nutrition 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 238000006701 autoxidation reaction Methods 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 229930002875 chlorophyll Natural products 0.000 description 1
- 235000019804 chlorophyll Nutrition 0.000 description 1
- ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 description 1
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000122 growth hormone Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- QANMHLXAZMSUEX-UHFFFAOYSA-N kinetin Chemical compound N=1C=NC=2N=CNC=2C=1NCC1=CC=CO1 QANMHLXAZMSUEX-UHFFFAOYSA-N 0.000 description 1
- 229960001669 kinetin Drugs 0.000 description 1
- 239000001115 mace Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 235000019629 palatability Nutrition 0.000 description 1
- 238000004161 plant tissue culture Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000002020 sage Nutrition 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000001585 thymus vulgaris Substances 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Landscapes
- Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
Abstract
Description
【発明の詳細な説明】
(産業上の利用分野)
本発明は、植物組織培養を利用した香辛料植物のアニス
のカルス、不定芽から極性溶媒で抽出した抗゛酸化剤に
関する。DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention relates to an antioxidant extracted with a polar solvent from the callus and adventitious buds of anise, a spice plant, using plant tissue culture.
(従来の技術)
従来、油脂を含む食品の抗酸化剤としてジブチルヒドロ
キシトルエン(BIT)、7’チルヒドロキシアニソー
ル(BHA)、アスコルビン酸、トコフェロール等が使
用されている。これらの抗酸剤は、それぞれの特徴をい
かして食品に使い分けられているが、BHA、BHT等
の合成抗酸化剤には一定の使用基準があり、添加量、添
力η食品の種類などが、厳しく制限されている。このた
め、安全性、嗜好性の面から天然抗酸化剤が要望されて
いる。セージ、ローズマリー、タイム、オレガノ、バジ
ル、メース等の香辛料植物の抽出物を天然抗酸化剤とし
ている製品はある。しかし、本発明者らが知り得る限り
では、香辛料植物のアニスのカルスまたは、不定芽に抗
酸化能があるという報告がなされているものは見いだし
得なかった。(Prior Art) Dibutylhydroxytoluene (BIT), 7'-hydroxyanisole (BHA), ascorbic acid, tocopherol, and the like have been used as antioxidants for foods containing fats and oils. These antioxidants are used in foods depending on their characteristics, but synthetic antioxidants such as BHA and BHT have certain usage standards, such as the amount added, the type of food, etc. , is severely restricted. Therefore, natural antioxidants are desired in terms of safety and palatability. Some products use extracts from spice plants such as sage, rosemary, thyme, oregano, basil, and mace as natural antioxidants. However, to the best of our knowledge, we have not found any report that the callus or adventitious buds of the spice plant anise have antioxidant ability.
本発明が解決しようとする問題点
香辛料は、季節、場所、気候、などにより生産性が異な
るので必ずしも安定した供給ができないまた、栽培する
ための広大な土地と労働力を必要とする。また、香辛料
から抽出した抗酸化剤は、香辛料の独特の香味を有する
ものが多い9本発明は、広範囲の食品に簡便に使用でき
る抗酸化剤として、天然物由来の′もので、かつ合成抗
酸化剤と同等以上の効力を持つもので食品に利用し安い
ように、特異的な香味の少ない抗酸化剤を得ることを目
的とする。Problems to be Solved by the Invention Spices have different productivity depending on the season, location, climate, etc., so they cannot always be supplied stably, and they require a large amount of land and labor for cultivation. In addition, many antioxidants extracted from spices have the unique flavor of spices. The purpose of this invention is to obtain an antioxidant with less specific flavor so that it can be used cheaply in foods and has an effect equal to or higher than that of an oxidizing agent.
問題を解決するための手段
本発明者らは、アニスの植物M mからカルスまたは不
定芽を誘導し、その抽出物が高い抗酸化性を有すること
を見いだした。本発明は、この知見をもとにアニスのカ
ルスまたは、不定芽より抽出した抽出液を有効成分とす
る抗酸化剤である。Means to Solve the Problem The inventors have induced callus or adventitious buds from the anise plant M m and found that the extract has high antioxidant properties. Based on this knowledge, the present invention provides an antioxidant containing an extract extracted from anise callus or adventitious buds as an active ingredient.
作用
本発明により、植物由来の抗酸化剤を安定して供給がで
きる。また、香辛料から抽出した抗酸化剤より香味が少
なくBHAと同等以上の抗酸化力を持ち食品の使用に適
している。Effect: According to the present invention, plant-derived antioxidants can be stably supplied. In addition, it has less flavor than antioxidants extracted from spices, and has antioxidant power equal to or higher than BHA, making it suitable for use in foods.
実施例
アニスのカルスまたは、不定芽を得るために次の操作を
行った。市販のアニスの種子を1%次亜塩素酸ナトリウ
ムと70%エタノールにより滅菌し、そのアニスの種子
を滅菌した0、8%の寒天上に置き無凹的に2〜3週間
育てる。成長した幼植物を無菌的に切断し、その切片か
らMurashige−3koog培地でカルス、不定
芽を誘導した。この培地には、成長ホルモンとしてカイ
ネチンを0〜5mg/l、ナフチル酢酸を0〜10m
g / 1、サッカロースを10〜40g/l、ジェラ
ンガムを1.5g/βを添加した。培養は25度の恒温
室で連続照明下(約2001ux〜200001ux)
で行った。3〜4週間でカルスを形成した。継代培養は
、3〜4週間毎に行った。Example The following operation was performed to obtain anise callus or adventitious buds. Commercially available anise seeds are sterilized with 1% sodium hypochlorite and 70% ethanol, and the anise seeds are placed on sterilized 0.8% agar and grown without cavities for 2 to 3 weeks. The grown seedlings were cut aseptically, and callus and adventitious buds were induced from the cut sections using Murashige-3koog medium. This medium contains 0 to 5 mg/l of kinetin and 0 to 10 m of naphthylacetic acid as growth hormones.
g/1, 10-40 g/l of sucrose and 1.5 g/β of gellan gum were added. Cultivation is carried out in a constant temperature room at 25 degrees under continuous lighting (approximately 2001 ux to 200001 ux)
I went there. A callus was formed in 3 to 4 weeks. Subculturing was performed every 3-4 weeks.
培養している間にカルスのみ増殖するもの、不定芽を形
成するものに分かれた。そのため、カルスは上記の固体
培養またはジェランガムを除いた液体培地で継代した。During culture, the plants were divided into those that only grew callus and those that formed adventitious buds. Therefore, the callus was subcultured in the solid culture described above or in a liquid medium without gellan gum.
不定芽は、液体培地で継代した。得られたカルス、不定
芽をホモジナイズし極性溶媒で抽出する。そして、その
iIt液を取り溶媒を除去し抗酸化成分を抽出する。使
用する溶媒がエチルアルコールまたは、水などのように
人体に影響のないものであれば、濾過しそのまま、ある
いは適宜濃縮して抗酸化剤として使用してもよいまた、
活性炭等でクロロフィル等を除去して使用することもで
きる。Adventitious buds were subcultured in liquid medium. The obtained callus and adventitious buds are homogenized and extracted with a polar solvent. Then, the iIt solution is taken, the solvent is removed, and the antioxidant components are extracted. If the solvent used is one that does not affect the human body, such as ethyl alcohol or water, it may be used as an antioxidant after filtration or after being concentrated as appropriate.
It is also possible to use activated carbon or the like to remove chlorophyll and the like.
以下に本発明について具体的に説明する。The present invention will be specifically explained below.
アニスのカルスまたはカルスからできた不定芽を湿重量
で200g〜300g取り、それぞれの試料量の2〜5
倍のエタノールと混合し冷暗所(4〜5℃)で1晩抽出
する。それぞれを濾紙で濾過し、その残さにエタノール
を加えてホモジナイズする。再度、濾紙で濾過する。そ
の残さにエタノールを加え混合し濾紙で濾過をする。そ
れぞれの全ての抽出濾液を集めて約30〜40℃で加温
しながら減圧下にてエタノールを留去し乾固残さを約5
g〜8g得る。それぞれの乾固残さにエタノールと水を
比が6対4になるように加えて10Qm6に定容する。Take 200 to 300 g of wet weight of anise callus or adventitious buds formed from callus, and take 2 to 5 of each sample amount.
Mix with twice as much ethanol and extract overnight in a cool, dark place (4-5°C). Filter each sample using filter paper, add ethanol to the residue, and homogenize. Filter again through filter paper. Add ethanol to the residue, mix, and filter through filter paper. All the extraction filtrates were collected and ethanol was distilled off under reduced pressure while heating at about 30 to 40°C, and the dry residue was reduced to about 50%
g to 8 g obtained. Ethanol and water were added to each dry residue in a ratio of 6:4 to make a volume of 10Qm6.
こうして得た抽出物を抗酸化剤とした。The extract thus obtained was used as an antioxidant.
実施例1
リノール酸の自動酸化に対する抗酸化効果の実験を行っ
た。0.1 Mホウ酸緩衝液(pI−+9.0 )
50 rn 1に0.2MIJノール酸エタノール溶液
を5ml添加した。さらに最V!−濃度が0.02%(
〜′/■)となるようにアニスのカルス及び不定芽から
の抽出物(抗酸化剤)をそれぞれ加え上記緩衝液で10
0mffに定容する。なお定容の際には、エタノールと
水の量がそれぞれの検体において同じようになるように
予め調整した後定容した。又、対照として抗酸化剤を含
まない試料と、0.02%B i(AとなるようにtJ
J整した試料を用いた。以上の試料を密栓、遮光した1
00mff容三角フラスコに入れ37℃の恒温槽にて
リノール酸の酸化を経口的にロダン鉄性で調べた。ロダ
ン鉄性は、食品工学実験書(上)京都大学農学部食品工
学教室)I P634−365 養賢堂(1979
)に従った。Example 1 An experiment was conducted on the antioxidant effect on autoxidation of linoleic acid. 0.1 M borate buffer (pI-+9.0)
5 ml of 0.2 MIJ nolic acid ethanol solution was added to 50 rn 1. Even more V! - concentration of 0.02% (
Extracts (antioxidants) from anise callus and adventitious buds were added to the buffer solution so that
Adjust the volume to 0mff. In addition, when determining the volume, the amounts of ethanol and water were adjusted in advance so that they were the same for each sample, and then the volume was determined. In addition, as a control, a sample containing no antioxidant and 0.02% B i (tJ
A J-adjusted sample was used. The above samples were sealed and shielded from light.
The oxidation of linoleic acid was examined orally using rhodan iron in a 00 mff Erlenmeyer flask in a constant temperature bath at 37°C. Rodan iron properties are Food Engineering Experiment Book (Part 1) Department of Food Engineering, Faculty of Agriculture, Kyoto University) I P634-365 Yokendo (1979
) was followed.
表1より、アニスのカルス及び不定芽の極性)容媒抽出
物の抗酸化力がB HAよりも強いことがわかる。Table 1 shows that the antioxidative power of the polar vehicle extract of anise callus and adventitious buds is stronger than that of BHA.
吸光度(500nm)
口数 カルス抽出物 不定芽抽出物
0 0.076 0.105
2 0.07G 0.115
5 0.0B6 0.12B
10 0.080 0.132
150.081 0.136
日数 B HA
0 0.073
20、+04
50.106
10 0.573
15 0.920
control
O,120
1,155
1,722
1,921
実施例2
アニスのカルス抽出物のラードの酸化に対する抗酸化効
果の試験を行った0本試験では、アニスのカルスをエタ
ノール抽出した後、乾固し水で回収後エタノール含有量
が90%になるように加え沈澱物と上′清に分けそれぞ
れの抗袖化試験を行った。市販されている抗酸化剤無添
加のラード100gに対して上記のアニスのカルス抽出
物を乾燥重量で0.02%になるように添加し60℃で
保存した。この過酸化物価の変化を経口的に調べた。対
照としてBHAを0.02%添加したラードと無添加の
ラードも60℃で保存し過酸化物価を経口的に測定した
0表2にその結果を示す、アニスのカルス抽出物の方が
B HAよりも強いことがわかる。Absorbance (500 nm) Number of mouths Callus extract Adventitious bud extract 0 0.076 0.105 2 0.07G 0.115 5 0.0B6 0.12B 10 0.080 0.132 150.081 0.136 Number of days B HA 0 0.073 20, +04 50.106 10 0.573 15 0.920 control O,120 1,155 1,722 1,921 Example 2 A test was conducted on the antioxidant effect of anise callus extract on lard oxidation. In this test, anise callus was extracted with ethanol, dried to dryness, collected with water, and then added to the mixture so that the ethanol content was 90%.The precipitate and supernatant were separated and an anti-sleeving test was conducted on each. . The above-mentioned anise callus extract was added to 100 g of commercially available antioxidant-free lard at a dry weight of 0.02% and stored at 60°C. Changes in peroxide value were examined orally. As a control, lard with 0.02% BHA added and lard without BHA were also stored at 60°C and the peroxide value was measured orally.Table 2 shows the results. Anise callus extract has higher BHA. It turns out that it is stronger than.
表2 POV (meq/kg)日数 抽出沈澱
物 抽出上清 BHAo 0゜13 0.13
0.132 0.39 0.25 0.209
7.77 6.08 8.4617 13.15
13.77 19.2822 25.03 23.5
0 28.10日数
7
2
contr。Table 2 POV (meq/kg) Days Extracted precipitate Extracted supernatant BHAo 0°13 0.13
0.132 0.39 0.25 0.209
7.77 6.08 8.4617 13.15
13.77 19.2822 25.03 23.5
0 28.10 days 7 2 contr.
O、13 0、38 18,51 25,27 35,30O, 13 0, 38 18,51 25, 27 35,30
Claims (1)
成分とする抗酸化剤 2、アニスのカルスからできた不定芽から極性溶媒で抽
出した物質を有効成分とする抗酸化剤[Claims] 1. An antioxidant containing as an active ingredient a substance extracted from anise callus with a polar solvent. 2. An antioxidant containing a substance extracted with a polar solvent from adventitious buds made from anise callus as an active ingredient. agent
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP23752889A JPH03100093A (en) | 1989-09-12 | 1989-09-12 | Antioxidant |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP23752889A JPH03100093A (en) | 1989-09-12 | 1989-09-12 | Antioxidant |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH03100093A true JPH03100093A (en) | 1991-04-25 |
Family
ID=17016669
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP23752889A Pending JPH03100093A (en) | 1989-09-12 | 1989-09-12 | Antioxidant |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH03100093A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP3581178A1 (en) | 2005-02-14 | 2019-12-18 | Suntory Holdings Limited | Composition containing dihomo-(gamma)-linolenic acid (dgla) as active ingredient |
-
1989
- 1989-09-12 JP JP23752889A patent/JPH03100093A/en active Pending
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP3581178A1 (en) | 2005-02-14 | 2019-12-18 | Suntory Holdings Limited | Composition containing dihomo-(gamma)-linolenic acid (dgla) as active ingredient |
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