JPH07224278A - Antioxidant and antioxidation method using fucoxanthin - Google Patents
Antioxidant and antioxidation method using fucoxanthinInfo
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- JPH07224278A JPH07224278A JP1824194A JP1824194A JPH07224278A JP H07224278 A JPH07224278 A JP H07224278A JP 1824194 A JP1824194 A JP 1824194A JP 1824194 A JP1824194 A JP 1824194A JP H07224278 A JPH07224278 A JP H07224278A
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- Prior art keywords
- fucoxanthin
- antioxidant
- algae
- contained
- extracted
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Abstract
(57)【要約】
【目的】 良好な抗酸化能を有し、安全性が高く、さら
に容易に製造することのできる抗酸化剤及び抗酸化方法
を提供することを目的とする。
【構成】 珪藻等の藻類から抽出した、下記式で表され
るフコキサンチンを用いる。
【化５】
フコキサンチンは不飽和脂肪酸などの酸化を防ぐ良好な
抗酸化能を有し、天然物として安全性が高い。フコキサ
ンチンは藻類に大量に含まれ、容易に抽出できる。食
品、化粧品及び医薬品用として適する。
(57) [Summary] [Object] An object of the present invention is to provide an antioxidant and an antioxidant method which have good antioxidant ability, are highly safe, and can be easily produced. [Constitution] Fucoxanthin represented by the following formula extracted from algae such as diatom is used. [Chemical 5] Fucoxanthin has a good antioxidant ability to prevent the oxidation of unsaturated fatty acids and is highly safe as a natural product. Fucoxanthin is contained in a large amount in algae and can be easily extracted. Suitable for food, cosmetics and pharmaceuticals.
Description
【０００１】[0001]
【産業上の利用分野】この発明は、フコキサンチンを用
いた抗酸化剤及び抗酸化方法に関するものである。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an antioxidant using fucoxanthin and an antioxidant method.
【０００２】[0002]
【従来の技術】下記式は、褐藻、珪藻（Phaeodactylum
tricornutum ）などの海草類に含まれるフコキサンチン
の構造式を示す。2. Description of the Related Art The following formula is for brown algae and diatom
shows the structural formula of fucoxanthin contained in seaweeds such as tricornutum).
【化３】 フコキサンチンは、脂溶性の橙色の物質であり、キサン
トフィル色素の一つとして知られていた。[Chemical 3] Fucoxanthin is a fat-soluble orange substance and was known as one of xanthophyll pigments.
【０００３】また、発明の名称が「けい藻から抗酸化剤
の取得方法」である特許登録番号１３４３９６号には、
珪藻に抗酸化能があることが示されている。[0003] Further, in Patent Registration No. 134396, whose title is "A method of obtaining an antioxidant from diatoms",
It has been shown that diatoms have antioxidant capacity.
【０００４】[0004]
【発明が解決しようとする課題】しかしながら、従来、
フコキサンチンは色素として知られており、抗酸化能等
を有することは知られていなかった。また、珪藻に含ま
れる抗酸化能を有する物質は、何であるかは不明であっ
た。[Problems to be Solved by the Invention] However, in the past,
Fucoxanthin is known as a pigment, and has not been known to have antioxidant ability or the like. Moreover, it was unclear what the substance having an antioxidant ability contained in diatom.
【０００５】この発明は上記のような問題点を解消する
ためになされたもので、本発明者らは、珪藻に含まれる
抗酸化能を有する物質を鋭意研究し、その物質がフコキ
サンチンであること及び、フコキサンチンを色素として
でなく抗酸化能を有する物質として使用できることを見
出した。従って、この発明は、それらの知見に基づき、
良好な抗酸化能を有し、さらに安全で容易に製造するこ
とのできる抗酸化剤及び抗酸化方法を提供することを目
的とする。The present invention has been made in order to solve the above problems, and the present inventors diligently studied a substance having an antioxidant ability contained in diatom, and the substance is fucoxanthin. It was also found that fucoxanthin can be used not as a pigment but as a substance having antioxidant ability. Therefore, the present invention is based on these findings,
It is an object of the present invention to provide an antioxidant and an antioxidant method which have good antioxidant ability and can be manufactured safely and easily.
【０００６】[0006]
【課題を解決するための手段】請求項１の発明に係る抗
酸化剤は、フコキサンチンを含む。The antioxidant according to the invention of claim 1 contains fucoxanthin.
【０００７】請求項２の発明に係る抗酸化剤は、フコキ
サンチンを含む、食品、化粧品及び医薬品に用いるため
の抗酸化剤である。The antioxidant according to the second aspect of the invention is an antioxidant containing fucoxanthin for use in foods, cosmetics and pharmaceuticals.
【０００８】請求項３の発明に係る抗酸化剤は、藻類よ
り抽出したフコキサンチンを含む、抗酸化剤である。An antioxidant according to a third aspect of the present invention is an antioxidant containing fucoxanthin extracted from algae.
【０００９】請求項４の発明に係る抗酸化方法は、フコ
キサンチンを用いる。In the antioxidant method according to the invention of claim 4, fucoxanthin is used.
【００１０】請求項５の発明に係る抗酸化方法は、フコ
キサンチンを、食品，化粧品及び医薬品に用いるための
抗酸化方法である。The antioxidant method according to the invention of claim 5 is an antioxidant method for using fucoxanthin in foods, cosmetics and pharmaceuticals.
【００１１】請求項６の発明に係る抗酸化方法は、藻類
から抽出したフコキサンチンを用いた、抗酸化方法であ
る。The antioxidant method according to the invention of claim 6 is an antioxidant method using fucoxanthin extracted from algae.
【００１２】[0012]
【作用】請求項１の発明における抗酸化剤は、フコキサ
ンチンが良好な抗酸化能を有するため、優れた抗酸化剤
として使用できる。The fucoxanthin of the present invention can be used as an excellent antioxidant because fucoxanthin has a good antioxidant ability.
【００１３】請求項２の発明における抗酸化剤は、フコ
キサンチンは天然物である珪藻等の藻類に含まれるので
安全性が高く、この抗酸化剤は食品、化粧品及び医薬品
に用いるのに適する。Since the fucoxanthin contained in algae such as diatom which is a natural product is highly safe, the antioxidant in the invention of claim 2 is suitable for use in foods, cosmetics and pharmaceuticals.
【００１４】請求項３の発明における抗酸化剤は、フコ
キサンチンは天然物である珪藻等の藻類に大量に含ま
れ、藻類から容易に抽出されるので、この抗酸化剤は容
易に製造できる。Since the fucoxanthin in the invention of claim 3 is contained in a large amount in natural algae such as diatom and is easily extracted from the algae, the antioxidant can be easily produced.
【００１５】請求項４の発明における抗酸化方法は、フ
コキサンチンが良好な抗酸化能を有するため、優れた抗
酸化方法を提供できる。In the antioxidant method according to the invention of claim 4, since fucoxanthin has a good antioxidant ability, an excellent antioxidant method can be provided.
【００１６】請求項５の発明における抗酸化方法は、フ
コキサンチンは天然物である珪藻等の藻類に含まれるの
で安全性が高く、この抗酸化方法は食品、化粧品及び医
薬品に用いるのに適する。Since the fucoxanthin contained in algae such as diatom which is a natural product is highly safe, the antioxidant method according to the invention of claim 5 is suitable for use in foods, cosmetics and pharmaceuticals.
【００１７】請求項６の発明における抗酸化方法は、フ
コキサンチンは天然物である珪藻等の藻類に大量に含ま
れ、藻類から容易に抽出されるので、この抗酸化方法は
容易に実施できる。In the antioxidant method according to the sixth aspect of the present invention, fucoxanthin is contained in a large amount in natural algae such as diatom and is easily extracted from the algae, so this antioxidant method can be easily implemented.
【００１８】[0018]
実施例１ 以下、この発明の一実施例を図について説明する。藻類
として例えば珪藻の一種であるフェオダクチラムトリコ
ルヌタムを用いて、それをハクソスウィーニー２Ｎ３Ｐ
培地で培養した。培地は、窒素、燐などで強化したもの
であれば他の培地でもよい。得られた藻体を乾燥し、ク
ロロホルム／メタノール（２：１）等の有機溶媒で、藻
体に含まれる脂溶性物質を抽出した。フコキサンチンは
その粗抽出液と共に抽出される。藻体の乾燥は、凍結乾
燥法など藻体に含まれる成分が酸化分解などの影響を極
力受けない方法が望ましい。抽出溶媒は、上記の混合溶
媒の他、各種のアルコール類、アセトン等のケトン類も
使用できる。得られた上記の粗抽出液にはフコキサンチ
ン以外に珪藻に含まれる油脂類、クロロフィル等の色素
が大量に含まれているので、粗抽出液をさらに溶媒抽出
しシリカゲルを担体とするカラムクロマトグラフィ、液
体クロマトグラフィ等の方法で分離して、最終的に、フ
コキサンチンを、薄層クロマトグラフィ上で単一のバン
ドとして精製した。Embodiment 1 An embodiment of the present invention will be described below with reference to the drawings. As an algae, for example, pheoductilum tricornutum, which is a kind of diatom, is used, and it is called Haxosweeney 2N3P.
Cultured in medium. The medium may be another medium as long as it is fortified with nitrogen, phosphorus or the like. The obtained algal cells were dried, and the fat-soluble substance contained in the algal cells was extracted with an organic solvent such as chloroform / methanol (2: 1). Fucoxanthin is extracted with the crude extract. It is desirable to dry the alga body by a method such as a freeze-drying method in which components contained in the alga body are not affected by oxidative decomposition as much as possible. As the extraction solvent, various alcohols and ketones such as acetone can be used in addition to the above mixed solvent. The crude extract obtained above contains a large amount of oils and fats contained in diatoms other than fucoxanthin, pigments such as chlorophyll, so column chromatography using silica gel as a carrier by further solvent extraction of the crude extract, After separation by a method such as liquid chromatography, fucoxanthin was finally purified as a single band on thin layer chromatography.
【００１９】この単一のバンドに含まれる物質を、質量
分析、赤外吸収分光、核磁気共鳴等で分析した。図１に
ＦＡＢ−ＭＳスペクトルグラフィによる分子量測定結果
を示す。高ｍ／ｚ域の拡大スペクトルグラム上で、分子
イオンピークと思われるシグナルがｍ／ｚ＝６５８に観
察される。図２に赤外線吸収スペクトルグラムによる測
定結果を示す。赤外線吸収スペクトルグラム上で、アレ
ン構造が観察される。図３に13ＣＮＭＲスペクトルグラ
フィによる測定結果を示す。合計４２個のＣが帰属され
る。The substances contained in this single band were analyzed by mass spectrometry, infrared absorption spectroscopy, nuclear magnetic resonance and the like. FIG. 1 shows the results of molecular weight measurement by FAB-MS spectroscopy. A signal that is considered to be a molecular ion peak is observed at m / z = 658 on the expanded spectrogram in the high m / z region. FIG. 2 shows the measurement result by infrared absorption spectrum gram. The allene structure is observed on the infrared absorption spectrogram. FIG. 3 shows the measurement results by 13 C NMR spectroscopy. A total of 42 C are assigned.
【００２０】上記の測定結果及びここには示されないが
可視部の吸収曲線、薄層クロマトグラフィの測定結果か
ら、以下の事実が示された。The following facts were shown from the above measurement results, the absorption curve in the visible region, which is not shown here, and the measurement results of thin layer chromatography.
【００２１】１．ＣＨ3 とＨが付いた−Ｃ＝Ｃ−Ｃ＝Ｃ
−の構造がある。 ２．ＣＨ3 が１１個あり、そのうち４個が−Ｃ＝Ｃ−Ｃ
＝Ｃ−構造の鎖上にあり、残りの７個はシクロヘキサン
の６員環にある。 ３．アレン構造Ｃ＝Ｃ＝Ｃがある。 ４．1. CH 3 and -C H is with = C-C = C
-There is a structure. 2. There are 11 CH 3 , of which 4 are -C = C-C
On the chain of the = C-structure, the remaining 7 are in the 6-membered ring of cyclohexane. 3. There is an allene structure C = C = C. 4.
【化４】 のエステル結合がある。 ５．アルコール性−ＯＨがある。 ６．分子量（最大のイオンピーク）が６５８であり、４
２個のＣがある。 ７．吸収曲線がβ−カロチンとよく似ている。 ８．薄層クロマトグラフィで展開するとβ−カロチンよ
り親水基を持っている。[Chemical 4] There is an ester bond of. 5. There is alcoholic-OH. 6. The molecular weight (maximum ion peak) is 658 and 4
There are two Cs. 7. The absorption curve is very similar to β-carotene. 8. When developed by thin layer chromatography, it has a hydrophilic group than β-carotene.
【００２２】以上により、この単一バンドの物質が分子
量６５８のフコキサンチンであることが同定できた。From the above, it was possible to identify that this single band substance was fucoxanthin having a molecular weight of 658.
【００２３】（抗酸化能試験）フコキサンチンの抗酸化
能を調べる試験を行った。不飽和脂肪酸としてリノール
酸及び、酸化反応の開始を促進するためのラジカル発生
剤としてアゾビスイソブチロニトリル（ＡＩＢＮ）を用
いた。リノール酸、ＡＩＢＮは、それぞれ、０．５Ｍ、
６ｍＭ程度のｎ−ヘプタノール溶液として混合し、全量
が５ｍＬの反応系を調整した。１つの反応系にはフコキ
サンチンを添加し、他の反応系には添加しないで対照系
とした。これらの系を、同時に６０℃程度に加熱し、そ
の時生じる過酸化物質の量を時間を追って定量した。結
果を図４に示す。この図において、縦軸は酸化されたリ
ノール酸の量（μｍｏｌ）を、横軸は反応時間を分単位
で示す。−○−はフコキサンチンを添加しない対照系で
あり、−●−はフコキサンチンを添加した系である。こ
の図から明らかなように、フコキサンチンを添加した系
は、対照系に比べて、酸化されたリノール酸の量が少な
く過酸化物質の生成が抑えられている。このことから、
フコキサンチンは抗酸化能を有することがわかる。ＡＩ
ＢＮ等のラジカル発生剤を加えなくても、反応は進行す
るが極めて遅くなり、測定に要する時間は日単位とな
る。(Antioxidant capacity test) A test was conducted to examine the antioxidant capacity of fucoxanthin. Linoleic acid was used as the unsaturated fatty acid, and azobisisobutyronitrile (AIBN) was used as the radical generator for promoting the initiation of the oxidation reaction. Linoleic acid and AIBN are 0.5M,
A 6 mM n-heptanol solution was mixed to prepare a reaction system having a total volume of 5 mL. Fucoxanthin was added to one reaction system and was not added to the other reaction system to serve as a control system. These systems were simultaneously heated to about 60 ° C., and the amount of the peroxide substance generated at that time was quantified over time. The results are shown in Fig. 4. In this figure, the vertical axis represents the amount of oxidized linoleic acid (μmol), and the horizontal axis represents the reaction time in minutes. -○-is a control system in which fucoxanthin is not added, and-●-is a system in which fucoxanthin is added. As is clear from this figure, in the system to which fucoxanthin was added, the amount of oxidized linoleic acid was smaller than that of the control system, and the production of the peroxide substance was suppressed. From this,
It can be seen that fucoxanthin has antioxidant ability. AI
Even if a radical generator such as BN is not added, the reaction proceeds but is extremely slow, and the time required for measurement is in units of days.
【００２４】[0024]
【発明の効果】以上のように、請求項１の発明によれ
ば、不飽和脂肪酸などの酸化を防ぐ良好な抗酸化能を有
するフコキサンチンを含むので、優れた抗酸化剤を提供
できる。As described above, according to the first aspect of the present invention, since fucoxanthin having a good antioxidant ability for preventing the oxidation of unsaturated fatty acids and the like is contained, an excellent antioxidant can be provided.
【００２５】請求項２の発明によれば、天然物として安
全性の点で問題がないフコキサンチンを含むので、請求
項１の発明の効果に加え、食料品、化粧品及び医薬品な
どに添加して利用できる効果もある。例えば、フコキサ
ンチンは脂溶性であるので、食用油、油脂をベースとし
た医薬品、クリーム等の化粧品に添加し、これらの製品
に含まれる油脂類の酸化を防止する。According to the invention of claim 2, since fucoxanthin, which is a natural product and has no problem in terms of safety, is included, therefore, in addition to the effect of the invention of claim 1, it is added to foods, cosmetics, pharmaceuticals and the like. There is also an effect that can be used. For example, since fucoxanthin is fat-soluble, it is added to cosmetics such as edible oils, oil-based drugs and creams to prevent oxidation of oils and fats contained in these products.
【００２６】請求項３の発明によれば、フコキサンチン
は天然物である珪藻等の藻類に大量に含まれ、藻類から
容易に抽出されるので、請求項１または請求項２の発明
の効果に加え、容易に製造できる効果もある。According to the invention of claim 3, fucoxanthin is contained in a large amount in natural algae such as diatom and is easily extracted from the algae. Therefore, the effect of the invention of claim 1 or 2 is obtained. In addition, there is an effect that it can be easily manufactured.
【００２７】請求項４の発明によれば、良好な抗酸化能
を有するフコキサンチンを用いるので、優れた抗酸化方
法を提供できる。According to the invention of claim 4, since fucoxanthin having a good antioxidant ability is used, an excellent antioxidant method can be provided.
【００２８】請求項５の発明によれば、天然物として安
全性の点で問題がないフコキサンチンを用いるので、請
求項４の発明の効果に加え、食料品、嗜好品、化粧品及
び医薬品などに利用できる効果もある。According to the invention of claim 5, fucoxanthin is used as a natural product which has no problem in terms of safety. Therefore, in addition to the effect of the invention of claim 4, it can be applied to foods, luxury items, cosmetics and pharmaceuticals. There is also an effect that can be used.
【００２９】請求項６の発明によれば、フコキサンチン
は天然物である珪藻等の藻類に大量に含まれ、藻類から
容易に抽出されるので、請求項４または請求項５の発明
の効果に加え、容易に実施できる効果もある。According to the invention of claim 6, fucoxanthin is contained in a large amount in algae such as diatom, which is a natural product, and is easily extracted from algae. Therefore, the effect of the invention of claim 4 or 5 is obtained. In addition, there is an effect that it can be easily implemented.
【図１】請求項１ないし６の発明に用いられるフコキサ
ンチンのＦＡＢ−ＭＳスペクトルグラフィによる分子量
測定結果を示すグラフ図である。FIG. 1 is a graph showing the results of measuring the molecular weight of fucoxanthin used in the invention of claims 1 to 6 by FAB-MS spectroscopy.
【図２】請求項１ないし６の発明に用いられるフコキサ
ンチンの赤外線吸収スペクトルグラムによる測定結果を
示すグラフ図である。FIG. 2 is a graph showing the measurement results of infrared absorption spectrum of fucoxanthin used in the invention of claims 1 to 6.
【図３】請求項１ないし６の発明に用いられるフコキサ
ンチンの13ＣＮＭＲスペクトルグラフィによる測定結果
を示すグラフ図である。FIG. 3 is a graph showing the measurement results of fucoxanthin used in the inventions of claims 1 to 6 by 13 C NMR spectroscopy.
【図４】請求項１ないし６の発明に用いられるフコキサ
ンチンの抗酸化能試験のデータを示すグラフ図である。FIG. 4 is a graph showing the data of the antioxidant capacity test of fucoxanthin used in the inventions of claims 1 to 6.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 西川 信行 東京都調布市西つつじが丘二丁目４番１号 東京電力株式会社技術研究所内 (72)発明者 平野 篤 東京都調布市西つつじが丘二丁目４番１号 東京電力株式会社技術研究所内 ─────────────────────────────────────────────────── ─── Continuation of front page (72) Nobuyuki Nishikawa Inventor Nobuyuki Nishitsujigaoka 2-4-1, Chofu-shi, Tokyo Inside TEPCO Technical Research Institute (72) Inventor Atsushi Hirano 2-4 Nishitsujigaoka, Chofu-shi, Tokyo No. 1 Inside TEPCO Technical Research Institute
Claims (6)
抗酸化剤。 【化１】 1. An antioxidant containing fucoxanthin represented by the following formula. [Chemical 1]
１記載の抗酸化剤。2. The antioxidant according to claim 1, which is used in foods, cosmetics and pharmaceuticals.
項１又は２記載の抗酸化剤。3. The antioxidant according to claim 1, wherein fucoxanthin is extracted from algae.
た抗酸化方法。 【化２】 4. An antioxidant method using fucoxanthin represented by the following formula. [Chemical 2]
４記載の抗酸化方法。5. The antioxidant method according to claim 4, which is used for foods, cosmetics and pharmaceuticals.
項４又は５記載の抗酸化方法。6. The antioxidant method according to claim 4, wherein fucoxanthin is extracted from algae.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP01824194A JP3501836B2 (en) | 1994-02-15 | 1994-02-15 | Antioxidant and antioxidant method using fucoxanthin |
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| JP01824194A JP3501836B2 (en) | 1994-02-15 | 1994-02-15 | Antioxidant and antioxidant method using fucoxanthin |
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| JP3501836B2 JP3501836B2 (en) | 2004-03-02 |
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| Application Number | Title | Priority Date | Filing Date |
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| FR2822701A1 (en) * | 2001-04-03 | 2002-10-04 | Lvmh Rech | USE OF ALGAE PHAEODACTYLUM EXTRACT AS A COSMETIC AGENT PROMOTING PROTEASOME ACTIVITY OF SKIN CELLS AND COSMETIC COMPOSITION CONTAINING SAME |
| KR20040047486A (en) * | 2002-11-28 | 2004-06-05 | 김선재 | Preparation of Oxidative Cleavage and Extraction of Fucoxanthin from Sea-weed(Brown algae) |
| WO2006077433A1 (en) * | 2005-01-21 | 2006-07-27 | Promar As | Sunscreen compositions comprising carotenoids |
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| JP2013540110A (en) * | 2010-09-30 | 2013-10-31 | ベイジン ギンコ グループ バイオロジカル テクノロジー カンパニー リミテッド | Application of fucoxanthin in the manufacture of products with neuroprotective action against neurodegenerative diseases |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| IL110139A0 (en) | 1993-06-28 | 1994-10-07 | Howard Foundation | Pharmaceutically-active antioxidants |
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