JPH0643323B2 - Garlic processing method - Google Patents
Garlic processing methodInfo
- Publication number
- JPH0643323B2 JPH0643323B2 JP60268177A JP26817785A JPH0643323B2 JP H0643323 B2 JPH0643323 B2 JP H0643323B2 JP 60268177 A JP60268177 A JP 60268177A JP 26817785 A JP26817785 A JP 26817785A JP H0643323 B2 JPH0643323 B2 JP H0643323B2
- Authority
- JP
- Japan
- Prior art keywords
- garlic
- ajoene
- hours
- reaction
- water
- 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.)
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Description
【発明の詳細な説明】 〔発明の背景〕 技術分野 本発明は、血小板凝集抑制作用を有するアホエン（Ajoe
ne）をニンニクから効率よく得るためのニンニクの加工
法に関する。別の観点からすれば、本発明は、アホエン
を生産する方法に関する。Description: BACKGROUND OF THE INVENTION Technical Field The present invention relates to ajoene (Ajoe) having a platelet aggregation inhibitory action.
garlic processing method for efficiently obtaining ne) from garlic. In another aspect, the invention relates to a method of producing ajoene.
先行技術 ニンニクは、中国、朝鮮、日本その他各国で栽培されて
いる多年生草木で、一般に強精強壮薬として知られてお
り、古くから健胃、発汗、利尿、去痰、整腸、殺菌およ
び駆虫薬として用いられている。Prior art Garlic is a perennial herb that is cultivated in China, Korea, Japan and other countries, and is generally known as a tonic tonic, and has been known for a long time as a healthy stomach, sweating, diuretic, expectorant, intestinal, bactericidal and anthelmintic drug. Is used as.
近年、ニンニクの薬効として血小板凝集抑制作用が注目
され、ニンニクの揮発成分（いわゆるガーリックオイ
ル）中に存在するメチルアリルトリスルフィドにその活
性があることが明らかにされた〔ランセット（Lance
t）、１(8212)、150-151(1981)〕。また、ニンニク中の
アリシンにも同様な活性があることが報告されている
〔ファイトケミストリー（Phytochemistry）、24、1593
-1594(1985)〕。Recently, attention has been paid to the inhibitory effect on platelet aggregation as a medicinal effect of garlic, and it was revealed that methylallyl trisulfide present in the volatile component of garlic (so-called garlic oil) has the activity [Lancet (Lance
t), 1 (8212), 150-151 (1981)]. It has also been reported that allicin in garlic has a similar activity [Phytochemistry, 24 , 1593.
-1594 (1985)].
一方、ブロック（Block）らは、ニンニクより下記の構
造式（Ｉ）で示される含硫化合物（アホエン（Ajoen
e））を単離し、これに血小板の凝集を抑制する作用が
あることを報告している〔ジャーナル・オブ・アメリカ
ン・ケミカル・ソサエティー（J.Amer.Chem.Soc.）、10
6、8295〜8296(1984)）。On the other hand, Block et al. Are based on garlic and include a sulfur-containing compound (Ajoen) represented by the following structural formula (I).
e)) and reported that it has an action of suppressing platelet aggregation [J.Amer.Chem.Soc.], 10
6 , 8295-8296 (1984)).
また、上記アホエンの血小板凝集抑制作用機構は、従来
報告されているアリウム（Allium）属から得られた上記
化合物（メチルアリルトリスルフィドおよびアリシン）
の作用機構とは異なることが示され〔スロンボシス・リ
サーチ（Thrombosis Research）、32、155〜169(198
3)〕、アホエンの脳血栓あるいは動脈硬化症等、循環器
領域への応用が期待されている。 In addition, the mechanism of the platelet aggregation inhibitory action of the above-mentioned ajoene is the above-mentioned compounds (methylallyl trisulfide and allicin) obtained from the genus Allium which have been reported so far.
Has been shown to be different from the mechanism of action of [Thrombosis Research, 32 , 155-169 (198
3)], Ajoen is expected to be applied to cardiovascular areas such as cerebral thrombosis and arteriosclerosis.
しかしながら上記アホエンは、天然のニンニク中に微量
にした存在せず、これを多量に得ることは困難であっ
た。However, the above-mentioned ajoene was not present in a small amount in natural garlic, and it was difficult to obtain a large amount of this.
要 旨 本発明は、血小板凝集抑制作用を有するアホエンをニン
ニクから効率よく得るための加工法に関するものであ
る。The present invention relates to a processing method for efficiently obtaining ajoene having a platelet aggregation inhibitory effect from garlic.
すなわち、本発明によるニンニクの加工法は、ニンニク
をｐＨ２〜６の酸性条件下かつ水性条件下に低級脂肪族
アルコールと接触させてこの含水低級脂肪族アルコール
中にアホエンを蓄積させること、を特徴とするものであ
る。That is, the method for processing garlic according to the present invention is characterized in that garlic is contacted with a lower aliphatic alcohol under acidic conditions of pH 2 to 6 and aqueous conditions to accumulate ajoene in the hydrous lower aliphatic alcohol. To do.
効 果 本発明によるニンニクの加工法によれば、後記実験例に
も示すように、極めて簡単にしかも高含量で（ニンニク
重量に対して、アホエン含量を約０．１％程度）血小板
凝集抑制作用を有するアホエンを含有するニンニク組成
物を収得することができる。従って、本発明は、医薬品
原料あるいは食品原料の供給に多大な貢献ゆなすものと
思われる。Effects According to the method for processing garlic according to the present invention, as shown in the experimental examples described later, it is extremely easy and at a high content (aphoene content is about 0.1% based on the weight of garlic) to inhibit platelet aggregation. It is possible to obtain a garlic composition containing ajoene having Therefore, the present invention seems to make a great contribution to the supply of pharmaceutical raw materials or food raw materials.
なお、本発明は単にニンニクを抽出に付してニンニク中
のアホエンを抽出するのではなくて、主としてアホエン
前駆体化合物からアホエンを生産する技術に関するもの
である。The present invention relates to a technique of producing ajoene mainly from an ajoene precursor compound, rather than simply extracting garlic to extract ajoene in the garlic.
ニンニク 本発明でいうニンニクは、ゆり科（Liliaceae）、アリ
ウム（Allium）属に属するアリウム・サティバム・リン
ネ（Allium sativum L.）を指し、例えばオオニンニク
（Allium sativum L.forma pekinese Makino）がこれに
あたる。Garlic The garlic in the present invention refers to Allium sativum L., which belongs to the lily family (Liliaceae) and the genus Allium (Allium sativum L.). .
目的画分を取得すべく材料となる部分はとりわけ鱗茎部
（内部に***してできた通常５〜２０個の割球状形の小
鱗茎が入っている）が好ましく、これを乾燥するか、ま
たはそのままの状態で抽出に供することができる。The part that becomes the material for obtaining the target fraction is preferably a bulb part (which usually contains 5 to 20 split bulb-shaped small bulbs formed by division inside), and this is dried or It can be used for extraction as it is.
アホエン 本発明でいうアホエン（Ajoene）とは、上記ニンニクよ
り得られる無色のオイル状物質で、前記構造式（Ｉ）で
示される化合物を指す。この化合物にはＥ−アホエンお
よびＺ−アホエンの幾何異性体が存在するが、本発明で
はいずれをも含むものである。Ajoene In the present invention, the ajoene is a colorless oily substance obtained from the above garlic and refers to the compound represented by the structural formula (I). This compound has geometrical isomers of E-ajoene and Z-ajoene, but the present invention includes both of them.
ニンニクの加工法 ニンニクを反応しやすいように粉砕、好ましくはホモジ
ネートした後、リン酸、塩酸、酢酸、クエン酸あるいは
酒石酸等薬学上許容できる任意の有機または無機の酸を
用いてｐＨ２〜６（さらに好ましくはｐＨ３〜４）に調
節した含水の炭素数１〜４程度、好ましくは１〜２、の
低級脂肪族アルコール（通常は１価アルコール）に加
え、室温あるいは加温下で反応を行う。Processing method of garlic After crushing garlic so that it is easy to react, preferably homogenizing, phospharic acid, hydrochloric acid, acetic acid, citric acid, tartaric acid or any pharmaceutically acceptable organic or inorganic acid is used to adjust the pH to 2 to 6 (further It is preferably added to a lower aliphatic alcohol (usually a monohydric alcohol) having a carbon number of about 1 to 4, preferably 1 to 2, adjusted to pH 3 to 4), and the reaction is carried out at room temperature or under heating.
本発明による低級脂肪族アルコールによるニンニクの加
工は、含水条件下に行なわれる。ここで含水条件下とい
うときの水は、ニンニク由来の水分をも考慮するものと
する。従って、生ニンニクを使用する場合は、無水アル
コールを使用する場合であっても含水条件下の加工と考
えるものとする。このような意味での「含水条件」は、
アルコール濃度が５〜９５％程度、好ましくは２０〜９
０％程度、であることが適当である。The processing of garlic with a lower aliphatic alcohol according to the present invention is carried out under hydrous conditions. Here, the water under the water-containing condition also takes into consideration the water content derived from garlic. Therefore, when raw garlic is used, it is considered to be processed under hydrous conditions even when anhydrous alcohol is used. In this sense, the "hydration condition" is
Alcohol concentration is about 5 to 95%, preferably 20 to 9
It is suitable to be about 0%.
このような酸性条件下および含水条件下において、室温
下では半日〜２日（好ましくは約１日）と反応時間が長
く、加温下（系の沸点以下が好ましい）では数分〜数十
時間（好ましくは４０〜９０℃で３０分〜１０時間程
度）と反応時間が短いのが通常である。なお必要に応じ
てニンニクの粉砕あるいはホモジネート時にアリナーゼ
の補酵素、例えばリン酸ピリドキシン、塩酸ピリドキシ
ン等をあらかじめ添加しておくのもよい。Under such acidic conditions and water-containing conditions, the reaction time is long at room temperature for half a day to 2 days (preferably about 1 day), and under heating (preferably below the boiling point of the system) several minutes to several tens hours. The reaction time is usually short (preferably at 40 to 90 ° C. for about 30 minutes to 10 hours). If necessary, a coenzyme of allinase, such as pyridoxine phosphate and pyridoxine hydrochloride, may be added in advance when garlic is crushed or homogenized.
この様にして得られた反応液は、過後、液を減圧濃
縮することにより、アホエンを高濃度に含有するニンニ
ク組成物を得ることができる。また、残渣は、任意の有
機溶媒、例えばクロロホルム、酢酸エチル、低級アルコ
ール（炭素数１〜３の１価アルコール）あるいは、アセ
トン等で２〜３回抽出することにより、残渣中に残存し
ているアホエンをさらに回収することができる。After the reaction liquid thus obtained is passed over and concentrated under reduced pressure, a garlic composition containing ajoene at a high concentration can be obtained. In addition, the residue remains in the residue by extracting 2-3 times with any organic solvent such as chloroform, ethyl acetate, lower alcohol (monohydric alcohol having 1 to 3 carbon atoms), or acetone. Ajoene can be further recovered.
アホエン含量の確認 上記処理法により得られたニンニク組成物中のアホエン
含量は、この組成物をメタノールに溶かした後、ＨＰＬ
Ｃで分析することにより容易に測定することができる。Confirmation of Ajoene Content The ajoene content in the garlic composition obtained by the above-mentioned treatment method was measured by dissolving the composition in methanol and then measuring HPL.
It can be easily measured by analyzing C.
実験例 アホエンの生成の条件検討例を示す。Experimental example The following is an example of studying conditions for the production of ajoene.
１． ｐＨの検討 凍結ニンニク６００ｇに塩酸ピリドキシン４mgを加え、
ホモジネートした。水にて全量１０００mlとし、これよ
り各々１００mlをとり、塩酸にてｐＨ１、クエン酸にて
ｐＨ３、４および５、無添加の状態でｐＨ７、および水
酸化ナトリウムにてｐＨ９、の計６種の試料を作製し、
各々１００mlのエタノールを加えた。反応混合物は６５
℃湯浴中にて４時間加熱した。1. Examination of pH Add 4 mg of pyridoxine hydrochloride to 600 g of frozen garlic,
Homogenized. Make up to 1000 ml with water, and take 100 ml of each, and use 6 types of samples, pH 1 with hydrochloric acid, pH 3, 4 and 5 with citric acid, pH 7 without addition, and pH 9 with sodium hydroxide. Is made,
100 ml of ethanol was added to each. The reaction mixture is 65
Heated in a water bath at ℃ for 4 hours.
アホエンの定量は、下記の通りに行なった。反応混合液
３０mlをとり、遠心分離（３０００rpm／１０分）後、
上清液をとり、水で希釈後、酢酸エチルにて抽出し、酢
酸エチル層を減圧濃縮後、得られた残渣をメタノールに
溶して、試料溶液とした。また、アホエン標準品を同様
にメタノールに溶して標準溶液とし、ＨＰＬＣにて分析
した。Ajoene was quantified as follows. After taking 30 ml of the reaction mixture and centrifuging (3000 rpm / 10 minutes),
The supernatant was taken, diluted with water, extracted with ethyl acetate, the ethyl acetate layer was concentrated under reduced pressure, and the obtained residue was dissolved in methanol to give a sample solution. In addition, a standard of ajoene was similarly dissolved in methanol to prepare a standard solution, which was analyzed by HPLC.
測定条件は、下記の通りである。The measurement conditions are as follows.
分離カラム：ＴＳＫゲルＬＳ４１０、３．９mm 内径×３０cm（東洋曹達工業（株）） 溶離液：３７％アセトニトリル 検出波長：２５４ｎｍ 結果は、下表の通りである。Separation column: TSK gel LS410, 3.9 mm inner diameter × 30 cm (Toyo Soda Kogyo Co., Ltd.) Eluent: 37% acetonitrile Detection wavelength: 254 nm The results are shown in the table below.
以上より、ｐＨは、弱酸性、特に２〜６程度、就中ｐＨ
３〜４が望ましいといえる。 From the above, the pH is weakly acidic, especially about 2 to 6, especially pH.
It can be said that 3 to 4 is desirable.
２． 反応温度および反応時間の検討 凍結ニンニク３００ｇに塩酸ピリドキシン２mgを加え、
ホモジネートした。水にて全量５００mlとし、クエン酸
を加えてｐＨ３〜４に調節した。これより１５０mlを３
検体とり、２５０mlのエタノールを加え、室温、６５℃
および８５℃の湯浴中にて加熱した。これらの試料より
経時的（室温：１０分後、１日、４日、７日、６５℃ま
たは８５℃：１０分、１時間、２時間、３時間、４時
間、６時間）に試料を採取し、１と同様に抽出処理して
分析を行った。結果は、添付の図面に示す通りである。2. Examination of reaction temperature and reaction time Add 2 mg of pyridoxine hydrochloride to 300 g of frozen garlic,
Homogenized. The total volume was adjusted to 500 ml with water, and citric acid was added to adjust the pH to 3-4. 150 ml 3 from this
Take a sample, add 250 ml of ethanol, room temperature, 65 ℃
And heated in a water bath at 85 ° C. Samples from these samples over time (room temperature: 10 minutes, 1 day, 4 days, 7 days, 65 ° C or 85 ° C: 10 minutes, 1 hour, 2 hours, 3 hours, 4 hours, 6 hours) Then, as in the case of 1, the sample was extracted and analyzed. The results are as shown in the attached drawings.
以下により、６５℃および８５℃加熱では、４時間後に
アホエンの生成が最大となることがわかった。また、室
温でも、徐々ではあるが、アホエンの生成がみとめら
れ、１日目には、加熱時の最大量に比べ約1/2量のアホ
エンの生成が確認された。From the following, it was found that after heating at 65 ° C. and 85 ° C., ajoene was maximized after 4 hours. In addition, even at room temperature, the production of ajoene was observed, albeit gradually, and on the first day, production of about 1/2 amount of ajoene was confirmed as compared with the maximum amount during heating.
３． エタノール濃度の検討 凍結ニンニク２０２ｇに塩酸ピリドキシン２mgを加え、
ホモジネートした。水にて全量４００mlとし、クエン酸
を加えてｐＨ３〜４に調整した。これより、７５ml、１
００mlおよび１５０mlをとり、各々にエタノール１５０
ml、１００mlおよび７５mlを加え、６５℃の℃湯浴中に
て加熱した。反応液より、１時間および４時間後に反応
混合液５mlをとり、１と同様に抽出処理して分析を行な
った。結果を、下表２に示す。3. Examination of ethanol concentration To 202 g of frozen garlic, add 2 mg of pyridoxine hydrochloride,
Homogenized. The total volume was adjusted to 400 ml with water, and citric acid was added to adjust the pH to 3-4. From this, 75 ml, 1
Take 00 ml and 150 ml, and add ethanol 150 to each.
ml, 100 ml and 75 ml were added and heated in a 65 ° C. water bath. After 1 hour and 4 hours from the reaction solution, 5 ml of the reaction mixture was taken and extracted in the same manner as in 1 for analysis. The results are shown in Table 2 below.
以上より、エタノール濃度が高いほどアホエン生成量が
高いことがわかった。 From the above, it was found that the higher the ethanol concentration, the higher the amount of ajoene produced.
４． ｐＨ調整における酸の種類の検討 凍結ニンニク５２０ｇに塩酸ピリドキシン４mgを加え、
ホモジネートした。水にて全量１０００mlとし、これに
より２００mlづつを４検体とり、クエン酸、酢酸、リン
酸、塩酸にてｐＨ３〜４に調整した。これらにエタノー
ル２００mlを各々加え、６５℃湯浴中にて加熱した。反
応液より、１時間および４時間後に反応混合液５mlをと
り、１と同様に抽出処理して、分析を行った。結果を表
３に示す。4. Examination of the type of acid in pH adjustment Pyridoxine hydrochloride 4 mg was added to frozen garlic 520 g,
Homogenized. The total volume was adjusted to 1000 ml with water, and 4 samples of 200 ml each were taken and adjusted to pH 3 to 4 with citric acid, acetic acid, phosphoric acid, and hydrochloric acid. To each of these, 200 ml of ethanol was added and heated in a 65 ° C water bath. After 1 hour and 4 hours from the reaction solution, 5 ml of the reaction mixture was taken, extracted in the same manner as in 1, and analyzed. The results are shown in Table 3.
以上により、酸としてリン酸、クエン酸および塩酸がア
ホエン生成量が高いことがわかった。 From the above, it was found that phosphoric acid, citric acid and hydrochloric acid as acids had a high ajoene production amount.
５．反応残渣中のアホエンの回収 凍結ニンニク２６０ｇに塩酸ピリドキシン２mgを加え、
ホモジネートした。水にて全量５００mlとし、クエン酸
を加えてｐＨ３〜４に調整した。これより２００mlをと
り、エタノール２００mlを加え、６５℃湯浴中にて４時
間加熱した。反応後、反応混合液１０mlをとり、遠心分
離（２０００rpm／５分）し、上清は１と同様に抽出処
理し、溶媒を留去し、遠心分離した残渣は、酢酸エチル
５mlにて２回振とう抽出後、溶媒を留去し、残渣をメタ
ノールに溶し、ＨＰＬＣ分析した。この結果、反応中生
成したアホエンの約３４％を残渣から回収することがで
きた。5. Recovery of ajoene in reaction residue To 260 g of frozen garlic, 2 mg of pyridoxine hydrochloride was added,
Homogenized. The total volume was adjusted to 500 ml with water, and citric acid was added to adjust the pH to 3-4. From this, 200 ml was taken, 200 ml of ethanol was added, and the mixture was heated in a water bath at 65 ° C. for 4 hours. After the reaction, take 10 ml of the reaction mixture, centrifuge (2000 rpm / 5 minutes), extract the supernatant in the same manner as in 1, distill off the solvent, and centrifuge the residue twice with 5 ml of ethyl acetate. After shaking extraction, the solvent was distilled off, the residue was dissolved in methanol and analyzed by HPLC. As a result, about 34% of the ajoene produced during the reaction could be recovered from the residue.
【図面の簡単な説明】 図面は、アホエン生成に対する温度の影響を示すグラフ
である。BRIEF DESCRIPTION OF THE DRAWINGS The drawing is a graph showing the effect of temperature on ajoene production.
Claims (2)
性条件下に低級脂肪族アルコールと接触させてこの含水
低級脂肪族アルコール中にアホエンを蓄積させることを
特徴とする、ニンニクの加工法。1. A method for processing garlic, which comprises contacting garlic with a lower aliphatic alcohol under acidic conditions of pH 2 to 6 and aqueous conditions to accumulate ajoene in the hydrous lower aliphatic alcohol.
１項のニンニクの加工法。2. The method for processing garlic according to claim 1, wherein the contact is carried out under heating.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60268177A JPH0643323B2 (en) | 1985-11-28 | 1985-11-28 | Garlic processing method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60268177A JPH0643323B2 (en) | 1985-11-28 | 1985-11-28 | Garlic processing method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62129224A JPS62129224A (en) | 1987-06-11 |
| JPH0643323B2 true JPH0643323B2 (en) | 1994-06-08 |
Family
ID=17454983
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60268177A Expired - Fee Related JPH0643323B2 (en) | 1985-11-28 | 1985-11-28 | Garlic processing method |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0643323B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012519679A (en) * | 2009-03-05 | 2012-08-30 | ニーム バイオテック リミテッド | How to prepare ajoene |
| KR101242580B1 (en) * | 2011-03-21 | 2013-03-19 | 숙명여자대학교산학협력단 | Preparation method for ajoene-enriched garlic extract |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2608252B2 (en) | 1994-09-16 | 1997-05-07 | 名古屋製酪株式会社 | Garlic processing method and method for producing ajoene-containing fats and oils |
| KR100889051B1 (en) | 2008-09-10 | 2009-03-20 | (주)새롬바이오 | Method for anti-browning garlic and anti-browning garlic processed product using the same |
-
1985
- 1985-11-28 JP JP60268177A patent/JPH0643323B2/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012519679A (en) * | 2009-03-05 | 2012-08-30 | ニーム バイオテック リミテッド | How to prepare ajoene |
| KR101242580B1 (en) * | 2011-03-21 | 2013-03-19 | 숙명여자대학교산학협력단 | Preparation method for ajoene-enriched garlic extract |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62129224A (en) | 1987-06-11 |
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