JPH02219890A - Anti-oxidizing agent - Google Patents
Anti-oxidizing agentInfo
- Publication number
- JPH02219890A JPH02219890A JP4020989A JP4020989A JPH02219890A JP H02219890 A JPH02219890 A JP H02219890A JP 4020989 A JP4020989 A JP 4020989A JP 4020989 A JP4020989 A JP 4020989A JP H02219890 A JPH02219890 A JP H02219890A
- Authority
- JP
- Japan
- Prior art keywords
- plastochromanol
- obtd
- antioxidant
- chromatography
- leaves
- 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
- 230000003064 anti-oxidating effect Effects 0.000 title abstract 3
- 239000007800 oxidant agent Substances 0.000 title abstract 2
- PTMZTTPJFDLIOR-HCCCIJMNSA-N (2r)-2,7,8-trimethyl-2-[(3e,7e,11e,15e,19e,23e,27e)-4,8,12,16,20,24,28,32-octamethyltritriaconta-3,7,11,15,19,23,27,31-octaenyl]-3,4-dihydrochromen-6-ol Chemical compound OC1=C(C)C(C)=C2O[C@@](CC/C=C(C)/CC/C=C(C)/CC/C=C(C)/CC/C=C(C)/CC/C=C(C)/CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)(C)CCC2=C1 PTMZTTPJFDLIOR-HCCCIJMNSA-N 0.000 claims abstract description 12
- PTMZTTPJFDLIOR-UHFFFAOYSA-N Plastochromanol 8 Natural products OC1=C(C)C(C)=C2OC(CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)(C)CCC2=C1 PTMZTTPJFDLIOR-UHFFFAOYSA-N 0.000 claims abstract description 12
- 150000002632 lipids Chemical class 0.000 claims abstract description 3
- 241000233788 Arecaceae Species 0.000 claims abstract 3
- 239000003963 antioxidant agent Substances 0.000 claims description 17
- 230000003078 antioxidant effect Effects 0.000 claims description 14
- 239000004480 active ingredient Substances 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract description 8
- 241000196324 Embryophyta Species 0.000 abstract description 4
- 238000004587 chromatography analysis Methods 0.000 abstract description 3
- 238000004440 column chromatography Methods 0.000 abstract description 2
- 238000007670 refining Methods 0.000 abstract 2
- 241000202746 Hyophorbe Species 0.000 abstract 1
- 238000007605 air drying Methods 0.000 abstract 1
- 230000002688 persistence Effects 0.000 abstract 1
- 235000006708 antioxidants Nutrition 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 7
- 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 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 229960000984 tocofersolan Drugs 0.000 description 4
- 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 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 229940087168 alpha tocopherol Drugs 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000002076 α-tocopherol Substances 0.000 description 3
- 235000004835 α-tocopherol Nutrition 0.000 description 3
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 238000004811 liquid chromatography Methods 0.000 description 2
- NJYFRQQXXXRJHK-UHFFFAOYSA-N (4-aminophenyl) thiocyanate Chemical compound NC1=CC=C(SC#N)C=C1 NJYFRQQXXXRJHK-UHFFFAOYSA-N 0.000 description 1
- GVJHHUAWPYXKBD-QLVXXPONSA-N (S,R,R)-alpha-tocopherol Chemical compound [H][C@@](C)(CCCC(C)C)CCC[C@@]([H])(C)CCC[C@@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C GVJHHUAWPYXKBD-QLVXXPONSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 241001133760 Acoelorraphe Species 0.000 description 1
- 101100098216 Caenorhabditis elegans rars-1 gene Proteins 0.000 description 1
- 235000001815 DL-alpha-tocopherol Nutrition 0.000 description 1
- 239000011627 DL-alpha-tocopherol Substances 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 244000184734 Pyrus japonica Species 0.000 description 1
- 241001092459 Rubus Species 0.000 description 1
- 229930003427 Vitamin E Natural products 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229960002089 ferrous chloride Drugs 0.000 description 1
- 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 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Fats And Perfumes (AREA)
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野］
本発明は油脂や食品の酸化防止に用いられる抗酸化剤に
関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to an antioxidant used for preventing oxidation of fats and oils and foods.
［従来技術］
従来、油脂や食品の酸化防止に用いられる抗酸化剤とし
ては、植物成分から得られるα−トコフェロール（ビタ
ミンＥ）や合成品の２．６−ジーｔ−ブチル−ｐ−クレ
ゾール（ＢＨＴ）等が一辰的によく知られている。[Prior Art] Antioxidants conventionally used to prevent the oxidation of fats and oils and foods include α-tocopherol (vitamin E) obtained from plant components and the synthetic product 2,6-di-t-butyl-p-cresol ( BHT) etc. are all well known.
〔発明が解決しようとする閏題点コ
現在使用されているα−トコフェロールは、効果が弱く
、合成抗酸化剤は安全性の点で問題がある０本発明は、
α−トコフェロールと同等あるいは、それ以上の抗酸化
力を有し、持続力のある化合物を提供するものである。[Currently used alpha-tocopherol has weak effects, and synthetic antioxidants have safety problems.
It provides a compound that has antioxidant power equivalent to or greater than α-tocopherol and has a long-lasting effect.
［問題点を解決するための手段］
本発明者らは、有効且つ安全な天然抗酸化剤を検索する
目的で熱帯植物に着目し、ヤシ科植物葉の抗酸化活性成
分を分画していったところ、本弁明を完成するに至った
もので、その構成は、プラストクロマノール−８、また
はその粗精製物を有効成分とすることを特徴とするもの
である。[Means for Solving the Problems] The present inventors focused on tropical plants for the purpose of searching for effective and safe natural antioxidants, and fractionated the antioxidant active components of palm leaves. As a result, we have completed the present invention, which is characterized in that its composition is plastochromanol-8 or a crudely purified product thereof as an active ingredient.
即ち、大量入手の容易なトラクリヤシモドキ（Ｍａｓｃ
ａｒｅｎａ ｖｅｒｓｃｈａｆｆｅｌｉｉ ）の葉から
脂質成分を抽出し、この成分中の抗酸化力を有するもの
を各種クロマトグラフィーを用いて単離精製し、核磁気
共鳴スペクトル、質量分析スペクトル等を用いて、その
構造を検討していったところ、この活性成分は既にゴム
ツキの葉の１成分として単離、報告されている（Ｂｉｏ
ｃｈｅ＠、 Ｊ 、 、 ９８． １７ｃ１９６５）プ
ラストクロマノール−８であることが判明した。That is, Masc is easily available in large quantities.
The lipid components were extracted from the leaves of (Arena verschaffelii), those with antioxidant properties were isolated and purified using various types of chromatography, and their structures were determined using nuclear magnetic resonance spectroscopy, mass spectrometry, etc. After further investigation, we found that this active ingredient has already been isolated and reported as a component of the leaves of Rubus japonica (Bio
che@, J, , 98. 17c1965) was found to be plastochromanol-8.
プラストクロマノール−８、およびその粗精製物の用途
については何ら報告されていない。There is no report on the use of plastochromanol-8 or its crude product.
［実施例］ 以下実施例を挙げて本発明を説明する。[Example] The present invention will be explained below with reference to Examples.
プラストクロマノール−８、の単離
ヤシ科植物の一種であるトラクリヤシモドキ（Ｍａｓｃ
ａｒｅｎａ ｖｅｒｓｃｈａｆｆｅｌｉｉ ）の生葉を
裁断後−長夜風乾し、ウイレー粉砕機により粉砕した。Isolation of plastochromanol-8 from Masc.
After cutting fresh leaves of Arena verschaffelii), they were air-dried for a long night and ground using a Wiley grinder.
粉砕物２．７Ｋｇ（水分９．８％ｗ、ｎ、）を１０倍五
のｎ−ヘキサンで二回抽出し、遠心分離した後、減圧濃
縮して抽出物６２．３ｇを得な。なお抽出溶媒はｎ−ヘ
キサン以外にクロロホルム、酢酸エチル等でもよい、こ
の抽出物を下記条件でカラムクロマトグラフィーにかけ
、クロロホルム、／アセトン＝ １００１０で溶出され
る活性画分を分取した。2.7 kg of the pulverized material (moisture 9.8% w, n) was extracted twice with 10x5 N-hexane, centrifuged, and concentrated under reduced pressure to obtain 62.3 g of the extract. Note that the extraction solvent may be chloroform, ethyl acetate, etc. other than n-hexane. This extract was subjected to column chromatography under the following conditions, and the active fraction eluted with chloroform/acetone = 10010 was fractionated.
カラム：シリカゲル、 １７０〜１２０ｗ＋ｅｓｈ１０
０ｍｍφ ｘ６００ｍｓ
移動相：、クロロホルム７／アセトン＝１００〜０流Ｒ
：４０ｍ１／ｍｉｎ。Column: silica gel, 170-120w+esh10
0 mmφ x 600 ms Mobile phase: Chloroform 7/acetone = 100 to 0 flow R
:40m1/min.
さらに、下記条件の液体クロマトグラフィーで溶出液５
００ｍ１ずつを分取し、フラクション−３を濃縮して活
性画分（Ｋ−１）１．５２ｇを得た。Furthermore, eluate 5 was subjected to liquid chromatography under the following conditions.
00 ml each was collected and fraction-3 was concentrated to obtain 1.52 g of active fraction (K-1).
カラム：総研科学製、５０＋ｕｉφ ｘ５００ｍｍシリ
カゲル
移動相：ヘキサン／酢酸エチル＝ ９３ ／ ７流量
： ６０ ｍ ｌ ／ ｍ ｉ ｎ 。Column: Souken Kagaku, 50+uiφ x 500mm Silica gel Mobile phase: Hexane/ethyl acetate = 93/7 flow rate
: 60ml/min.
Ｋ−１をさらに液体クロマトグラフィーカラム： ＹＭ
Ｃ製、２０＋＋ｍφ ｘ２５０ａ＋ｍシリカゲル
移動相：ヘキサン／酢酸エチル＝ ９７／３流Ｊｉ
：４ｍｌ／ｍｉｎ。K-1 further liquid chromatography column: YM
Made by C, 20++mφ x 250a+m Silica gel mobile phase: Hexane/ethyl acetate = 97/3 flow Ji
:4ml/min.
で分画し、純度の高いプラストクロマノール−８を６４
ｍｇ得た。プラストクロマノール−８の機器分析結果を
以下に示す。64 to obtain highly pure plastochromanol-8.
I got mg. The results of instrumental analysis of Plastochromanol-8 are shown below.
マススペクトル（ｍ、／ｚ）： ７５０ （Ｍ＋）１８
９．１５１．６９
Ｃ−１３ＮＭＲスペクトルδ（ｐｐｍ）：１４６．３，
１４５．７，１３４．９
１２５．８，１２４．３，１２１．６
１１８．３゜１１２．２，７５．２
３９．８．３９．７，３１．５，２６．７２４．０．２
２．２，１６．０，１１．９１１．８
及びＩＲスｔ−クトルの結果から、この化合物は′フラ
ノクロメン−８であると同定された。Mass spectrum (m, /z): 750 (M+)18
9.151.69 C-13 NMR spectrum δ (ppm): 146.3,
145.7, 134.9 125.8, 124.3, 121.6 118.3° 112.2, 75.2 39.8.39.7, 31.5, 26.724.0.2
From the results of 2.2, 16.0, 11.911.8 and IR spectrum, this compound was identified as 'furanochromene-8.
抗酸化力の測定
プラストクロマノール−８、およびＫ ７１ ｉｉ’ｉ
ｉ分の抗酸化力を知るために以下の試験を行なった。Measurement of antioxidant power Plastochromanol-8 and K 71 ii'i
The following test was conducted to find out the antioxidant power of i-minute.
この試験のうち水−アルコール系で行なったものは、Ｐ
ＯＶ法、ＴＢＡ法であり、油系で行な−）たものは重！
法である。また、各試験に於いては、抗酸化剤を全く加
えないものを対照とし、別に一般的な抗酸化剤であるｄ
ｌ−α−トコフェロールをプラストクロマノール−８と
同量加えたものを比較例とした。Among these tests, those conducted in a water-alcohol system were P
The OV method and TBA method are heavy!
It is the law. In addition, in each test, we used a control that did not contain any antioxidants, and we also used d, which is a common antioxidant, as a control.
A comparative example was prepared by adding l-α-tocopherol in the same amount as plastochromanol-8.
１ ）ＰＯＶ法（ロダン鉄性）
Ｌｏｏｍ！の摺り合わせ三角フラスコに、リノール！１
ｆｆ１０．１４ｇ、９９．５％エタノール１０ｍ１，０
．２Ｍリン酸バッファー１０ｍ１及びエタノールに溶か
した試＄：１２８０μｇを加え、更に水を加えて全量を
２５ｍ１とし、これを密栓して５０℃の恒温相中にいれ
、経時的にサンプリングして酸化度合を測定した。サン
プル溶液の０．１ｍｌに、７５％エタノール溶液４．７
ｒｎｔ、３０％チオシアン酸アンモニウム水溶液０゜ｌ
ｍ １及び２Ｘ１０ Ｍ塩化第一鉄の３４５％塩酸
液０．１ｒｒｔ１を加え、３分後に、５００ｎｍの吸光
度を測定した。結果を図１に示す。1) POV method (Rodan iron) Loom! Linol in a rubbed Erlenmeyer flask! 1
ff10.14g, 99.5% ethanol 10ml1.0
．． Add 10 ml of 2M phosphate buffer and 1,280 μg of the sample dissolved in ethanol, add water to make a total volume of 25 ml, seal it tightly, put it in a constant temperature phase at 50°C, and measure the degree of oxidation by sampling over time. It was measured. Add 4.7 ml of 75% ethanol solution to 0.1 ml of sample solution.
rnt, 30% ammonium thiocyanate aqueous solution 0゜l
m 1 and 2×10 M ferrous chloride in 345% hydrochloric acid solution 0.1 rrt1 were added, and after 3 minutes, the absorbance at 500 nm was measured. The results are shown in Figure 1.
２）ＴＢＡ法
前記１）と同様に調整した試料から２．０ｒｎｌを遠沈
管に取り、２０％トリクロロ酢酸水溶液１．０ｍｌ、０
．６７％チオバルビッール酸水溶液２．０ｍｌを加えて
１０分子ｇ１煮沸し、その後３０００ｒｐｍで１０分間
遠心分離を行い、上澄液の５３２ｎｍに於ける吸光度を
測定した。結果を２２に示す。2) TBA method Take 2.0rnl of the sample prepared in the same manner as in 1) above into a centrifuge tube, add 1.0ml of 20% trichloroacetic acid aqueous solution,
．． 2.0 ml of 67% thiobarbylic acid aqueous solution was added and 10 molecules g1 were boiled, followed by centrifugation at 3000 rpm for 10 minutes, and the absorbance of the supernatant at 532 nm was measured. The results are shown in 22.
３〉重量法
試料２００μｇをエタノールに溶かし、その溶液をビー
カーに介入して、エタノールを窒素雰囲気中で完全に揮
発させてから、リノールＥｌ１ｇを入れ、４０℃の恒温
槽中に放置し、前記のビーカーを経時的に秤呈しな。結
果を図３に示す。3> Dissolve 200 μg of the gravimetric sample in ethanol, put the solution into a beaker, completely volatilize the ethanol in a nitrogen atmosphere, add 1 g of linol El, leave it in a thermostat at 40°C, and add the solution as described above. Weigh the beaker over time. The results are shown in Figure 3.
［発明の効果］
以上の抗酸化試験より、プラストクロマノール−８、ま
たはその粗精製物は水−アルコール系および、油系に於
て従来抗酸化剤として用いられているｄｌ−α−トコフ
ェロールを上回る抗酸化力をしめしている。[Effects of the invention] From the above antioxidant tests, plastochromanol-8 or its crude product contains dl-α-tocopherol, which is conventionally used as an antioxidant in water-alcohol systems and oil systems. It shows superior antioxidant power.
第１図及至第３図は本発明抗酸化剤の抗酸化力試験の結
果を示したグラフであり、それぞれ第１はＰｏｖ法、第
２図はＴＢＡ法、第３図は重量法によって測定したもの
である。Figures 1 to 3 are graphs showing the results of the antioxidant power test of the antioxidant of the present invention, with the first being measured by the POV method, the second being the TBA method, and the third being the gravimetric method. It is something.
Claims (1)
化学式、表等があります▼ を有効成分とする抗酸化剤。 ２）ヤシ科（Ｐａｌｍａｅ）植物の葉から抽出した脂質
を有効成分とする抗酸化剤。[Claims] 1) Plastochromanol-8▲ formula represented by the following formula,
There are chemical formulas, tables, etc. ▼ Antioxidant with active ingredient. 2) An antioxidant whose active ingredient is lipid extracted from the leaves of palmae plants.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4020989A JPH02219890A (en) | 1989-02-22 | 1989-02-22 | Anti-oxidizing agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4020989A JPH02219890A (en) | 1989-02-22 | 1989-02-22 | Anti-oxidizing agent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH02219890A true JPH02219890A (en) | 1990-09-03 |
Family
ID=12574392
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4020989A Pending JPH02219890A (en) | 1989-02-22 | 1989-02-22 | Anti-oxidizing agent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02219890A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009110782A1 (en) * | 2008-03-06 | 2009-09-11 | Nova Laboratories Sdn Bhd | Extract from oil palm leaves comprising phenolic acids |
-
1989
- 1989-02-22 JP JP4020989A patent/JPH02219890A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009110782A1 (en) * | 2008-03-06 | 2009-09-11 | Nova Laboratories Sdn Bhd | Extract from oil palm leaves comprising phenolic acids |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Lang et al. | Simultaneous determination of tocopherols, ubiquinols, and ubiquinones in blood, plasma, tissue homogenates, and subcellular fractions | |
| Lang et al. | Quantitative determination of vitamin E and oxidized and reduced coenzyme Q by high-performance liquid chromatography with in-line ultraviolet and electrochemical detection | |
| Konings et al. | Liquid chromatographic determination of tocopherols and tocotrienols in margarine, infant foods, and vegetables | |
| Matthaus et al. | FA and tocopherol composition of Vietnamese oilseeds | |
| Ikediobi et al. | Gas-liquid chromatography of mycotoxins of the trichothecene group | |
| El‐Ghorab et al. | Antioxidant activity of Egyptian Eucalyptus camaldulensisvar. brevirostrisleaf extracts | |
| CN101355995A (en) | Improved process for analyzing for separating, and for isolating polar protic monomers and/or oligomers | |
| Tepe et al. | Evaluation of the chemical composition and antioxidant activity of the essential oils of Peucedanum longifolium (Waldst. & Kit.) and P. palimbioides (Boiss.) | |
| Pimentel et al. | Extracts from the leaves of Piper piscatorum (Trel. Yunc.) obtained by supercritical extraction of with CO2, employing ethanol and methanol as co-solvents | |
| Yates et al. | Isolation and analysis of carrot constituents: myristicin, falcarinol, and falcarindiol | |
| Durley et al. | Leaf analysis for abscisic, phaseic and 3-indolylacetic acids by high-performance liquid chromatography | |
| Khidyrova et al. | Polyprenols and triterpenoids from leaves of Alcea nudiflora | |
| Cooper et al. | Preparative separation of pyrrolizidine alkaloids by high-speed counter-current chromatography | |
| Hostettmann et al. | Direct obtention of pure compounds from crude plant extracts by preparative liquid chromatography | |
| de Koning | Determination of myo-inositol and phytic acid by gas chromatography using scyllitol as internal standard | |
| JPH02219890A (en) | Anti-oxidizing agent | |
| Robeson et al. | α-Tocopherol, a Natural Antioxidant in a Fish Liver Oil | |
| CN110041166B (en) | Dracaena cochinchinensis extract with antibacterial function and preparation and application thereof | |
| Lekar’ et al. | Extraction of chlorogenic acid from marsh cinquefoil Comarum palustre L. in subcritical water | |
| Champagnat et al. | Essential oil composition of Vetiveria nigritana from Mali | |
| Asri et al. | Combination of High-Performance Liquid Chromatography (HPLC) Methods for Isolation of Ampelopsin C, a Trimeric Oligostilbene. | |
| Milašiene et al. | Evaluation of antioxidactivity of green and black tea (Camellia sinensis) and rooibos (Aspalathus linearis) tea extracts by means of HPLC with reaction detector | |
| Stemmer et al. | Effects of lethal yellowing on the composition of the phloem sap from coconut palms in Jamaica. | |
| JP3444936B2 (en) | Antioxidant | |
| Baca et al. | Separation of the α-tocopherol model compound 2, 2, 5, 7, 8-pentamethyl-6-chromanol from its oxidation products by high performance liquid chromatography |