JPH01202261A - Bait for red fish and culture of red fish - Google Patents

Bait for red fish and culture of red fish

Info

Publication number
JPH01202261A
JPH01202261A JP63026678A JP2667888A JPH01202261A JP H01202261 A JPH01202261 A JP H01202261A JP 63026678 A JP63026678 A JP 63026678A JP 2667888 A JP2667888 A JP 2667888A JP H01202261 A JPH01202261 A JP H01202261A
Authority
JP
Japan
Prior art keywords
astaxanthin
bait
red
fatty acid
ester
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
Application number
JP63026678A
Other languages
Japanese (ja)
Inventor
Kuniaki Sakado
坂戸 邦昭
Kenichi Mochida
持田 顕一
Hirofusa Nishinaka
西中 弘興
Toshio Abe
安部 敏男
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
KH Neochem Co Ltd
Original Assignee
Kyowa Hakko Kogyo Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Kyowa Hakko Kogyo Co Ltd filed Critical Kyowa Hakko Kogyo Co Ltd
Priority to JP63026678A priority Critical patent/JPH01202261A/en
Publication of JPH01202261A publication Critical patent/JPH01202261A/en
Pending legal-status Critical Current

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  • Feed For Specific Animals (AREA)
  • Fodder In General (AREA)

Abstract

PURPOSE:To improve both the body and flesh colors of red fishes, by incorporating the bait for red fishes with a fatty acid ester of astaxanthin to enhance the light resistance of astaxanthin. CONSTITUTION:Using a conventional method to esterify alcohols, the hydroxyl group of astaxanthin is esterified with a higher fatty acid such as linoleic acid or palmitic acid or a lower fatty acid, thereby the light resistance and other stability of the astaxanthin in an aqueous solution or bait can be improved significantly. Growth of red fishes using this bait would give the color tone near or superior to the body color of natural fishes.

Description

【発明の詳細な説明】 産業上の利用分野 本発明は養殖魚類の体色を改良する餌料に関する。詳し
くいえば本発明は、赤色魚の体色を改良する餌料に関す
る6 また、本発明は赤色魚の体色を改良する養殖方法にも関
する。
DETAILED DESCRIPTION OF THE INVENTION Field of the Invention The present invention relates to a feed that improves the body color of cultured fish. More specifically, the present invention relates to a feed that improves the body color of red fish.6 The present invention also relates to a farming method that improves the body color of red fish.

従来の技術 さけ・ます類の肉色やマダイ類の体色は、主としてアス
タキサンチンに由来し、養殖魚にアスタキサンチンを添
加した餌料を供することにより、肉色および体色を改善
する方法が知られている(特開昭54−70995号公
報、特開昭57−206342号公報、特公昭48−1
2798号公報)。
Conventional technology The flesh color of salmon and trout and the body color of red sea bream are mainly derived from astaxanthin, and a method is known to improve the flesh color and body color by feeding farmed fish with feed containing astaxanthin ( JP-A-54-70995, JP-A-57-206342, JP-A-48-1
No. 2798).

しかしながら一般にカロチノイドは不安定な色素であっ
て、光、特に紫外線によって容易に分解される。アスタ
キサンチンも例外ではなく、水溶液あるいは餌料中での
安定性が極めて乏しいことが判明した。
However, carotenoids are generally unstable pigments and are easily degraded by light, especially ultraviolet light. Astaxanthin is no exception, and it has been found that its stability in aqueous solutions or feeds is extremely poor.

発明が解決しようとする課題 したがってアスタキサンチンの耐光性を改とする技術の
開発が望まれていた。ここに提案する発明は、この課題
を解決することを目的とするものである。
Problems to be Solved by the Invention Accordingly, it has been desired to develop a technique for improving the light resistance of astaxanthin. The invention proposed herein aims to solve this problem.

課題を解決するための手段 発明者らは上記の課題を解決しようとして研究した結果
、アスタキサンチンの水酸基を脂肪酸でエステル化する
ことによって、水溶液あるいは餌料の中でのアスクキサ
ンチンの安定性が大幅に向上することを見出し、本発明
を完成したものである。
Means for Solving the Problems The inventors conducted research to solve the above problems and found that by esterifying the hydroxyl groups of astaxanthin with fatty acids, the stability of astaxanthin in aqueous solutions or feeds was significantly improved. The present invention has been completed based on this discovery.

すなわち本発明は、アスタキサンチンの脂肪酸エステル
を含有することを特徴とする赤色魚用餌料である。
That is, the present invention is a feed for red fish characterized by containing a fatty acid ester of astaxanthin.

また他面において、本発明はアスクキサンチンの脂肪酸
エステルを赤色魚に投与することを特徴とする赤色魚の
養殖方法でもある。
In another aspect, the present invention is also a method for cultivating red fish, which comprises administering a fatty acid ester of askuxanthin to the red fish.

本発明の構成について以下に詳説する。The configuration of the present invention will be explained in detail below.

(アスタキサンチンの脂肪酸エステル)アスタキサンチ
ンをエステル化する脂肪酸としては、リノール酸、オレ
イン酸、バルミチン酸などの飽和又は不飽和脂肪酸を使
うことができるが、これらの高級脂肪酸に限られること
はなく、低級脂肪、酸をも使用することができる。
(Fatty acid ester of astaxanthin) As the fatty acid for esterifying astaxanthin, saturated or unsaturated fatty acids such as linoleic acid, oleic acid, and valmitic acid can be used, but they are not limited to these higher fatty acids, and lower fatty acids can be used. , acids can also be used.

アスクキサンチンの脂肪酸エステルは公知化合物[例え
ば[ヘルベチ力・ヒミカ・アクタ(Helv、  Ch
im、  Acta)第61巻、第2609頁(197
8年)]であって、その製法としては、アルコール類を
エステル化するための慣用方法を使用することができる
Fatty acid esters of asquixanthin are known compounds [e.g. [Helv, Ch.
im, Acta) Volume 61, Page 2609 (197
8)], and the conventional method for esterifying alcohols can be used for its production.

アスタキサンチンの脂肪酸エステルの合成方法を説明す
るために、脂肪酸の例としてバルミチン酸を選択し、ア
スタキサンチンジパルミトイルエステルの合成例を参考
例1及び2として示す。
In order to explain the method for synthesizing astaxanthin fatty acid ester, valmitic acid is selected as an example of the fatty acid, and examples of synthesizing astaxanthin dipalmitoyl ester are shown as Reference Examples 1 and 2.

参考例1 アスクキサンチン26mgをI Omfiのテトラヒド
ロフランに溶解し、0.5rr+12のピリジンと0.
8mI2のバルミトイルクロリドを添加し、室温で一晩
反応させた。反応液に酢酸エチル50mβを加えてエス
テル化されたアスタキサンチンを抽出し、エステル化さ
れたアスタキサンチンを含着する酢酸エチル層を水で洗
浄し、ついで飽和食塩水で洗浄した後、無水硫酸ナトリ
ウム上で乾燥した後に濃縮し、油状のアスタキサンチン
ジパルミトイルエステル40mgを得た。
Reference Example 1 26 mg of asquixanthin was dissolved in I Omfi tetrahydrofuran, and 0.5rr+12 pyridine and 0.5rr+12 pyridine were dissolved.
8ml2 of valmitoyl chloride was added and allowed to react overnight at room temperature. The esterified astaxanthin was extracted by adding 50 mβ of ethyl acetate to the reaction solution, and the ethyl acetate layer impregnating the esterified astaxanthin was washed with water, then with saturated saline, and then washed over anhydrous sodium sulfate. After drying, it was concentrated to obtain 40 mg of oily astaxanthin dipalmitoyl ester.

参考例2 フッラフ4フ口ドチーマ(Phaffia rhodo
zymal酵母の菌体破砕物からアスタキサンチンをア
セトンで抽出し、抽出液を濃縮し、酢酸エチルに転溶し
た後に濃縮し、アスタキサンチン0.18%を含む油状
粗精製物を得た。この油状物質的10gを少量のクロロ
ホルムに溶解し、ヘキサン中で充填したシリカゲルカラ
ム(120mA)に吸着させ、ヘキサン200mj2で
洗浄後、ヘキサン:酢酸エチル=50:Iの組成の溶媒
から徐々に酢酸エチル濃度を増加させてゆくとアスクキ
サンチンが溶出される。これを集めて濃縮し、約95m
gの粗精製物(10ないし20%のアスタキサンチンを
含有する。)を得た。
Reference example 2 Phaffia rhodo
Astaxanthin was extracted from crushed cells of Zymal yeast with acetone, the extract was concentrated, dissolved in ethyl acetate, and then concentrated to obtain an oily crude product containing 0.18% of astaxanthin. 10 g of this oily substance was dissolved in a small amount of chloroform, adsorbed on a silica gel column (120 mA) packed in hexane, washed with 200 mj2 of hexane, and then gradually dissolved in ethyl acetate from a solvent with a composition of hexane: ethyl acetate = 50: I. Askuxanthin is eluted as the concentration is increased. This was collected and concentrated, approximately 95 m
g of a crude product (containing 10 to 20% astaxanthin) was obtained.

このアスタキサンチン粗精製物170mgを10mj+
のテトラヒドロフランに溶解し、0.5m℃のピリジン
と0.8m℃のバルミトイルクロリドを加え、室温で一
晩反応させた。反応液に50mβの酢酸エチルを加えて
不溶物を濾別し、酢酸エチル層を水で洗浄し、ついで飽
和食塩水で洗浄し、無水硫酸ナトリウム上で乾燥後、蒸
発乾固した。残液を少量のヘキサンに溶解し、上述と同
様にシリカゲルカラム(50mJ2)で精製し、ヘキサ
ン:酢酸エチル=10:lの溶出区分を集めて濃縮し、
263mgのアスタキサンチンジパルミトイルエステル
を得た。
170mg of this crudely purified astaxanthin is added to 10mj+
of tetrahydrofuran, pyridine at 0.5 m°C and balmitoyl chloride at 0.8 m°C were added, and the mixture was reacted overnight at room temperature. 50 mβ of ethyl acetate was added to the reaction solution, insoluble matter was filtered off, and the ethyl acetate layer was washed with water, then with saturated brine, dried over anhydrous sodium sulfate, and then evaporated to dryness. The residual liquid was dissolved in a small amount of hexane, purified using a silica gel column (50 mJ2) in the same manner as above, and the eluted fraction of hexane:ethyl acetate = 10:l was collected and concentrated.
263 mg of astaxanthin dipalmitoyl ester was obtained.

実  施  例 実施例1 上記の参考例によって調製されたアスタキサンチンジパ
ルミトイルエステルの餌料中の安定性を検討した。
Examples Example 1 The stability of astaxanthin dipalmitoyl ester prepared according to the above reference example in feed was investigated.

参考例2で得られたアスタキサンチンジパルミトイルエ
ステル127mgを制用餌料(ホワイトフィツシュミー
ル約65%、澱粉的25%、ビール酵母約4%、大豆粕
約4%、ミネラルその他約2%)loogに加え、各l
ogに分けて、あるものは5℃に、他のものは30℃に
90日間放置し、アスタキサンチンエステルの安定性を
検討した。対照飼料としてファッフィア・ロドチーマ酵
母抽出物、オキアミ抽出物およびカロフィルピンクを含
む制用餌料を調製使用した。その結果は下表に示すよう
に、アスタキサンチンの残存率から判定すると、アスタ
キサンチンジパルミトイルエステルは他の試料に比較し
て極めて安定であることが判明した。
127 mg of astaxanthin dipalmitoyl ester obtained in Reference Example 2 was added to control feed (about 65% white fish meal, 25% starch, about 4% brewer's yeast, about 4% soybean meal, about 2% minerals and others). In addition, each l
The stability of the astaxanthin ester was examined by dividing it into 200g and leaving some at 5°C and others at 30°C for 90 days. As a control feed, a controlled feed containing Faffia rhodozyma yeast extract, krill extract, and calophyll pink was prepared and used. The results are shown in the table below, and as judged from the residual rate of astaxanthin, it was found that astaxanthin dipalmitoyl ester was extremely stable compared to other samples.

実施例2 実施例1で示したアスタキサンチンジパルミトイルエス
テルを含有する水産用餌料に同量の水を加えて、マダイ
用餌料を調製した。
Example 2 The same amount of water was added to the aquaculture feed containing astaxanthin dipalmitoyl ester shown in Example 1 to prepare feed for red sea bream.

第1の試験区には上記餌料を使用し、第2の試験区には
、上記餌料のアスタキサンチンジパルミトイルエステル
の代りに等モル量のアスタキサンチンを含む餌料を使用
し、第3の試験区には第1試験区の餌料からアスタキサ
ンチンジパルミトイルエステルを除いた餌料を使用した
The first test group used the above feed, the second test group used a feed containing an equimolar amount of astaxanthin instead of the astaxanthin dipalmitoyl ester in the above feed, and the third test group used a feed containing an equimolar amount of astaxanthin. A feed obtained by removing astaxanthin dipalmitoyl ester from the feed of the first test group was used.

飼育試験には当字のマダイ(体長15〜17am)を各
試験区に13匹ずつ使用し、24ないし25℃で4週間
飼育した後、マダイの色調を判断した。投餌は1日に2
回行い、1回につき約10 g / 13匹を与えた。
In the rearing test, 13 red sea bream (body length: 15 to 17 am) were used in each test section, and after being reared for 4 weeks at 24 to 25°C, the color tone of the red sea bream was determined. Feeding 2 times a day
Approximately 10 g/13 animals were fed each time.

第1の試験区で飼育されたマダイの色調は、天然マダイ
の体色に近いか、それを上回るものであった。
The color tone of the red sea bream raised in the first test area was close to or exceeded the body color of wild red sea bream.

実施例3 参考例1のアスタキサンチンジパルミトイルエステルの
製法において、バルミチン酸の代りにカプロン酸CHJ
(CH!1.C0OHを使い、アスタキサンチンシカブ
ロイルエステルを調製した。このアスタキサンチンシカ
ブロイルエステル130mgを実施例1と同様に制用餌
料100gに混入し、その各10gを使用し、実施例1
と同じアスタキサンチンシカブロイルエステルの餌料中
における安定性を検討した・ 法衣に結果を示すとおり、アスタキサンチンシカブロイ
ルエステルは、他の試料と比較して極めて安定であった
Example 3 In the method for producing astaxanthin dipalmitoyl ester of Reference Example 1, caproic acid CHJ was used instead of valmitic acid.
(CH!1.C0OH was used to prepare astaxanthin cabroyl ester. 130 mg of this astaxanthin cabroyl ester was mixed into 100 g of control feed in the same manner as in Example 1, and 10 g of each was used.
We investigated the stability of astaxanthin cicabroyl ester, which is the same as that of the previous study, in feed.As shown in the results, astaxanthin cicabroyl ester was extremely stable compared to other samples.

発明の効果 本発明の餌料は、空気中および水中において耐光性その
他の安定性が優れ、この餌料を使用してマダイを飼育す
れば、その色調は天然マダイの体色に近いか、+れを上
回るものが得られる。
Effects of the Invention The feed of the present invention has excellent light resistance and other stability in the air and water, and if red sea bream is raised using this feed, the color tone will be close to or slightly different from that of natural red sea bream. You can get more than that.

Claims (2)

【特許請求の範囲】[Claims] (1)アスタキサンチンの脂肪酸エステルを含有するこ
とを特徴とする赤色魚用餌料。
(1) A red fish feed characterized by containing a fatty acid ester of astaxanthin.
(2)アスタキサンチンの脂肪酸エステルを赤色魚に投
与することを特徴とする赤色魚の養殖方法。
(2) A method for cultivating red fish, which comprises administering astaxanthin fatty acid ester to red fish.
JP63026678A 1988-02-09 1988-02-09 Bait for red fish and culture of red fish Pending JPH01202261A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP63026678A JPH01202261A (en) 1988-02-09 1988-02-09 Bait for red fish and culture of red fish

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP63026678A JPH01202261A (en) 1988-02-09 1988-02-09 Bait for red fish and culture of red fish

Publications (1)

Publication Number Publication Date
JPH01202261A true JPH01202261A (en) 1989-08-15

Family

ID=12200056

Family Applications (1)

Application Number Title Priority Date Filing Date
JP63026678A Pending JPH01202261A (en) 1988-02-09 1988-02-09 Bait for red fish and culture of red fish

Country Status (1)

Country Link
JP (1) JPH01202261A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1171002A1 (en) * 1999-04-19 2002-01-16 Norsk Hydro Asa Pigment
WO2003093229A1 (en) * 2002-04-30 2003-11-13 Suntory Limited Astaxanthin medium-chain fatty acid ester, process for producing the same and composition containing the ester
US7253297B2 (en) 2002-02-06 2007-08-07 Dsm Ip Assetts B.V. Astaxanthin esters
EP1867327A1 (en) 2006-06-16 2007-12-19 Yamaha Hatsudoki Kabushiki Kaisha Astaxanthin and esters thereof for protecting neurocytes and treating Parkinson's disease

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6054647A (en) * 1983-09-05 1985-03-29 Riken Vitamin Co Ltd Feed composition for red sea bream

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6054647A (en) * 1983-09-05 1985-03-29 Riken Vitamin Co Ltd Feed composition for red sea bream

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1171002A1 (en) * 1999-04-19 2002-01-16 Norsk Hydro Asa Pigment
US6709688B1 (en) * 1999-04-19 2004-03-23 Norsk Hydro Asa Pigment
US7253297B2 (en) 2002-02-06 2007-08-07 Dsm Ip Assetts B.V. Astaxanthin esters
WO2003093229A1 (en) * 2002-04-30 2003-11-13 Suntory Limited Astaxanthin medium-chain fatty acid ester, process for producing the same and composition containing the ester
KR100941899B1 (en) * 2002-04-30 2010-02-11 산토리 홀딩스 가부시키가이샤 Astaxanthin medium-chain fatty acid ester, process for producing the same and composition containing the ester
EP1867327A1 (en) 2006-06-16 2007-12-19 Yamaha Hatsudoki Kabushiki Kaisha Astaxanthin and esters thereof for protecting neurocytes and treating Parkinson's disease

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