JPH0366289B2 - - Google Patents
Info
- Publication number
- JPH0366289B2 JPH0366289B2 JP56120373A JP12037381A JPH0366289B2 JP H0366289 B2 JPH0366289 B2 JP H0366289B2 JP 56120373 A JP56120373 A JP 56120373A JP 12037381 A JP12037381 A JP 12037381A JP H0366289 B2 JPH0366289 B2 JP H0366289B2
- Authority
- JP
- Japan
- Prior art keywords
- garlic
- essential oil
- component
- clathrate compound
- cyclic dextrin
- 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
- 240000002234 Allium sativum Species 0.000 claims description 25
- 235000004611 garlic Nutrition 0.000 claims description 25
- 239000000341 volatile oil Substances 0.000 claims description 16
- 229920001353 Dextrin Polymers 0.000 claims description 7
- 239000004375 Dextrin Substances 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 235000019425 dextrin Nutrition 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000004615 ingredient Substances 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 description 6
- 241000282472 Canis lupus familiaris Species 0.000 description 5
- 239000000047 product Substances 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 229920000858 Cyclodextrin Polymers 0.000 description 2
- 239000001116 FEMA 4028 Substances 0.000 description 2
- 201000006353 Filariasis Diseases 0.000 description 2
- 241000287828 Gallus gallus Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 description 2
- 235000011175 beta-cyclodextrine Nutrition 0.000 description 2
- 229960004853 betadex Drugs 0.000 description 2
- 235000013330 chicken meat Nutrition 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000003449 preventive effect Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 210000002700 urine Anatomy 0.000 description 2
- 206010063659 Aversion Diseases 0.000 description 1
- 241000271566 Aves Species 0.000 description 1
- 241000282465 Canis Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 235000013594 poultry meat Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000008729 scordinin Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Description
【発明の詳細な説明】
本発明者等はにんにく成分がロイコチトゾーン
症又はフイラリン症に有効であることを発見し、
特許出願をした。しかし、その製品は不透性容器
を用いない場合は有効成分の一部が揮散する恐れ
がある。また本製品は香りが強いため、配合飼料
製造時に配合することは困難であつた。更にフイ
ラリア症予防剤製造工程である打錠中には一部有
効成分が揮散する欠点があつた。本発明は上記諸
欠点を改良するために種々の研究を行ない完成し
たものである。[Detailed Description of the Invention] The present inventors have discovered that garlic components are effective against leukocytozoonosis or filarinosis,
I filed a patent application. However, if the product is not packaged in an impermeable container, there is a risk that some of the active ingredient may evaporate. In addition, this product has a strong scent, so it was difficult to incorporate it during the production of mixed feed. Furthermore, there was a drawback that some of the active ingredients evaporated during tableting, which is the manufacturing process of the filariasis preventive agent. The present invention has been completed through various researches aimed at improving the above-mentioned drawbacks.
香辛料のエツセンシヤルオイルを環状デキスト
リンに包接せしめることは例えば特開昭50−
82262等により公知であるが、個々の成分につい
ての詳細な研究発表はく、既発表内での追試を行
なつた場合はゲスト成分の被包接量が比較的に少
なく（精油の場合は環状デキストリンに対し最高
６％）、または有機溶媒洗浄により離脱し易い。
これに対し、本発明者等は種々の研究の結果、水
溶媒を無機又は有機の酸によつてPH１〜４に調整
することにより、被包接成分がにんにく精油の場
合、環状デキストリンに対し最高30％まで包接さ
れ、更に附着物を洗浄するために有機溶媒を用い
た場合も比較的に被包接成分が離脱され難いこと
を見出だした。 For example, the inclusion of essential oil of spices in cyclic dextrin was disclosed in Japanese Patent Application Laid-Open No. 1973-
82262, etc., but there are no detailed research publications on individual components, and when additional studies are conducted within the previously published studies, the amount of encapsulation of guest components is relatively small (in the case of essential oils, cyclic (up to 6% based on dextrin) or is easily removed by washing with an organic solvent.
On the other hand, as a result of various studies, the present inventors found that by adjusting the pH of the water solvent to 1 to 4 with an inorganic or organic acid, when the clathrate component is garlic essential oil, the highest It has been found that even when up to 30% of the clathrated components are clathrated and an organic solvent is used to wash the adhesion, it is relatively difficult for the clathrated components to be separated.
更にこの包接化合物を用いて各種製剤を調合し
た場合もにんにく臭はほとんど感じられず、また
製造工程においても精油の揮散は見られず、動物
に与えた場合はその体内において環状デキストリ
ンは完全に分解され、包接化合物でない場合の有
効成分を与えた場合と同等の効力を示すことが判
明した。 Furthermore, when various preparations are prepared using this clathrate compound, there is almost no garlic odor, and no volatilization of the essential oil is observed during the manufacturing process, and when given to animals, cyclic dextrin is completely removed in the animal's body. It was found that the active ingredient was degraded and showed the same efficacy as when the active ingredient was given without the clathrate compound.
以下実施例及び実験例により製造法及び効果確
認につき詳述する。 The manufacturing method and effect confirmation will be explained in detail below using Examples and Experimental Examples.
実施例(1) β−サイクロデキストリン400ｇをク
エン酸にてPH２に調整した水に懸濁させ、これに
にんにく精油（生鮮にんにくより水蒸気蒸留にて
取得したもの）100ｇを加え、全量を２とする。
常温中にて約５時間撹拌する。減圧濾過し、濾集
した固体を常温減圧乾燥又は風乾する。取得物は
白色粉末にてほとんどにおいてはない。収量は約
480ｇ。以下本品をCDGと略称する。Example (1) 400 g of β-cyclodextrin is suspended in water adjusted to pH 2 with citric acid, and 100 g of garlic essential oil (obtained from fresh garlic by steam distillation) is added to make the total amount 2. .
Stir at room temperature for about 5 hours. Filter under reduced pressure, and dry the solid collected under reduced pressure at room temperature or in air. The product obtained is mostly white powder. The yield is approx.
480g. Hereinafter, this product will be abbreviated as CDG.
実施例(2) β−サイクロデキストリン400ｇを塩
酸にてPH３に調整した水に懸濁させ、これににん
にく精油50ｇ、にんにく有効成分（スコルジニ
ン）50ｇを加え、全量を２とする。常温中にて
約５時間撹拌する。減圧濾過し、濾集した固体を
常温減圧乾燥又は風乾する。取得物は白色の粉末
でほとんどにおいてはない。収量は約480ｇ。Example (2) 400 g of β-cyclodextrin is suspended in water adjusted to pH 3 with hydrochloric acid, and 50 g of garlic essential oil and 50 g of garlic active ingredient (scordinin) are added to make the total amount 2. Stir at room temperature for about 5 hours. Filter under reduced pressure, and dry the solid collected under reduced pressure at room temperature or in air. Most of what you get is a white powder. Yield is approximately 480g.
実験例(1) 実施例(1)で得られる濾液についてガス
クロマトグラフイーを行なつたが、にんにく精油
のピークは現れずにんにく精油はすべて包接化合
物の形成に使われたことが判明した。Experimental Example (1) Gas chromatography was performed on the filtrate obtained in Example (1), but the peak of garlic essential oil did not appear, indicating that all of the garlic essential oil was used for the formation of clathrate compounds.
実験例(2) 実施例(1)で用いたにんにく精油の硫黄
定量（シエニガー法）を行なつた結果は51.3％で
あり、CDGのそれは10.6％であつた。以上より
CDG中にはにんにく精油が約20％包接されてい
ることが判明した。Experimental Example (2) The sulfur content of the garlic essential oil used in Example (1) was determined (Schieniger method) to be 51.3%, and that of CDG was 10.6%. From the above
It was found that about 20% of garlic essential oil was included in CDG.
実験例(3) ニワトリ10羽（平均体重は１羽当り２
Kg）を各５羽ずつ２群に分け、Ａ群には１羽当り
CDG15mgを、Ｂ群（対照）には１羽当りにんに
く精油３mgをそれぞれ飼料に混ぜて与え、10日後
には血漿、呼気、尿を採取してガスクロマトグラ
フイーによる定量を行なつたところ、にんにく精
油に由来する物質のピーク高（定量値）について
Ａ・Ｂ両群間に差はなかつた。これにより環状デ
キストリンは体内にて分解され、ロイコチトゾー
ン症の予防効果についてＡ・Ｂ両群に同等の効果
が期待された。Experimental example (3) 10 chickens (average weight 2 per chicken)
Kg) were divided into two groups of 5 birds each, and group A had one bird per bird.
15mg of CDG was given to group B (control), and 3mg of garlic essential oil per bird was mixed into the feed. After 10 days, plasma, exhaled breath, and urine were collected and quantitatively determined by gas chromatography. There was no difference between groups A and B in the peak height (quantitative value) of substances originating from. As a result, the cyclic dextrin was degraded in the body, and both groups A and B were expected to have the same preventive effect on leukocytozoonosis.
実験例(4) 雑種犬（体重は１頭当り約５Kg）８頭
を各４頭ずつ２群に分け、Ａ群には１頭当り
CDG35mgを、Ｂ群（対照）には１頭当りにんに
く精油７mgをそれぞれ飼料に混ぜて与え、10日後
に血漿、呼気、尿を採取してガスクロマトグラフ
イーによる定量を行つたところ、にんにく精油に
由来する物質のピーク高（定量値）についてＡ・
Ｂ両群間に差を生じなかつた。この結果より、環
状デキストリンは犬体内にて分解し、にんにく精
油が遊離したものと推定され、犬フイラリア症の
予防効果についてＡ・Ｂ両群に同等の効果が期待
された。Experimental example (4) 8 mongrel dogs (weighing about 5 kg each) were divided into 2 groups of 4 dogs each, with 1 dog per dog in group A.
35mg of CDG was given to Group B (control), and 7mg of garlic essential oil per head was mixed into the feed. After 10 days, plasma, exhaled breath, and urine were collected and quantitatively determined by gas chromatography. Regarding the peak height (quantitative value) of the substance that
B There was no difference between the two groups. From this result, it was presumed that cyclic dextrin was decomposed in the dog's body and garlic essential oil was liberated, and both groups A and B were expected to be equally effective in preventing canine filariasis.
以上により易揮発性になる欠点を持つにんにく
精油を配合飼料の大量生産時における飼料配合の
初期に配合することができるので、養鶏業者等の
小量生産時の配合の手間を省くことができる。ま
た不透性容器を用いる必要もないため、その分コ
ストダウンを果し得た。さらに投与動物がにんに
く精油の香に対し、忌避を示す場合もあり得るが
CDGの場合はその恐れがない。 As described above, garlic essential oil, which has the disadvantage of being easily volatile, can be added at the beginning of the feed formulation during mass production of compounded feed, thereby saving the labor of compounding for small-scale production by poultry farmers and the like. Furthermore, since there is no need to use an impermeable container, costs can be reduced accordingly. Furthermore, it is possible that treated animals may show an aversion to the scent of garlic essential oil.
In the case of CDG, there is no such fear.
Claims (1)
在下でクエン酸又は揮発性鉱酸にてPHを１〜４に
調整した後、接触せしめ、にんにく成分を環状デ
キストリンへ包接せしめることを特徴とするにん
にく成分包接化合物。 ２ にんにく成分がにんにく有効成分である特許
請求の範囲第１項のにんにく成分包接化合物。 ３ にんにく成分がにんにく精油である特許請求
の範囲第１項のにんにく成分包接化合物。[Scope of Claims] 1 Garlic component and cyclic dextrin are brought into contact after adjusting the pH to 1 to 4 with citric acid or volatile mineral acid in the presence of water, so that the garlic component is included in the cyclic dextrin. A garlic component clathrate compound characterized by: 2. The garlic ingredient clathrate compound according to claim 1, wherein the garlic ingredient is a garlic active ingredient. 3. The garlic component clathrate compound according to claim 1, wherein the garlic component is garlic essential oil.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56120373A JPS5821620A (en) | 1981-07-30 | 1981-07-30 | Clathrate of garlic constituents |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56120373A JPS5821620A (en) | 1981-07-30 | 1981-07-30 | Clathrate of garlic constituents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5821620A JPS5821620A (en) | 1983-02-08 |
| JPH0366289B2 true JPH0366289B2 (en) | 1991-10-16 |
Family
ID=14784593
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56120373A Granted JPS5821620A (en) | 1981-07-30 | 1981-07-30 | Clathrate of garlic constituents |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5821620A (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2550193A1 (en) * | 1983-08-05 | 1985-02-08 | Sal Fine Chemicals Internation | Inclusion complexes of methyl and allyl trisulphide with cyclodextrins, process for preparing them and pharmaceutical compositions containing them |
| JPS6191128A (en) * | 1984-10-11 | 1986-05-09 | Zenichi Kawashima | Preparation of odorless garlic |
| JPS61215328A (en) * | 1985-03-20 | 1986-09-25 | Susumu Oshiba | Antithrombotic agent |
| CN104982762B (en) * | 2015-07-14 | 2017-06-06 | 菏泽天鸿果蔬有限公司 | A kind of garlic polysaccharide piece and preparation method thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5592341A (en) * | 1979-01-05 | 1980-07-12 | Kaken Pharmaceut Co Ltd | Preparation of clathrate compound |
| JPS5646837A (en) * | 1979-09-27 | 1981-04-28 | Kowa Yakuhin Kogyo Kk | Preparation of ibuprofen clathrate compound |
| JPS5661369A (en) * | 1979-10-26 | 1981-05-26 | Iwaki Seiyaku Kk | Inclusion compound of thialamide or its acid addition salt |
-
1981
- 1981-07-30 JP JP56120373A patent/JPS5821620A/en active Granted
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5592341A (en) * | 1979-01-05 | 1980-07-12 | Kaken Pharmaceut Co Ltd | Preparation of clathrate compound |
| JPS5646837A (en) * | 1979-09-27 | 1981-04-28 | Kowa Yakuhin Kogyo Kk | Preparation of ibuprofen clathrate compound |
| JPS5661369A (en) * | 1979-10-26 | 1981-05-26 | Iwaki Seiyaku Kk | Inclusion compound of thialamide or its acid addition salt |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5821620A (en) | 1983-02-08 |
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