JPH07206753A - Novel compound by demethylation of curcumin and production thereof - Google Patents
Novel compound by demethylation of curcumin and production thereofInfo
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- JPH07206753A JPH07206753A JP6002837A JP283794A JPH07206753A JP H07206753 A JPH07206753 A JP H07206753A JP 6002837 A JP6002837 A JP 6002837A JP 283794 A JP283794 A JP 283794A JP H07206753 A JPH07206753 A JP H07206753A
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- curcumin
- reaction
- production
- inhibitory activity
- tyrosinase
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract
Description
【０００１】[0001]
【産業上の利用分野】この発明は、ο−ジヒドロキシ構
造を有し、強い抗酸化性、抗炎症性及び金属にキレート
作用を及ぼし、・ＯＨを補足する抗酸化剤並びにチロシ
ナーゼ阻害活性を保有することを目的としたクルクミン
脱メチル化新規化合物及びその製造方法に関する。This invention has an o-dihydroxy structure, exerts strong antioxidant property, anti-inflammatory property and chelate action on metals, and possesses an anti-oxidant which complements .OH and a tyrosinase inhibitory activity. The present invention relates to a novel curcumin demethylated compound and a method for producing the same.
【０００２】[0002]
【従来の技術】従来天然にはトコフェロールをはじめ多
くのフェノール性抗酸化物質が存在することが知られ、
多くの研究がなされている。その中で、ターメリックに
存在するクルクミンは分子内にフェノール性水酸基と、
β−ジケトン（diketone）構造を併せ持つことにより強
い抗酸化性や、抗炎症性を示すことが知られている。最
近では抗腫瘍活性があることも報告され注目されてい
る。2. Description of the Related Art Conventionally, it is known that many phenolic antioxidants including tocopherol exist in nature,
Much research has been done. Among them, turmeric curcumin has a phenolic hydroxyl group in the molecule,
It is known that it has strong antioxidative property and anti-inflammatory property by having a β-diketone structure together. Recently, it has been reported that it has an antitumor activity and has been drawing attention.
【０００３】一般的にフェノール性抗酸化物質は、ο−
ジヒドロキシ（dihydroxy ）構造を有するとその活性が
強くなることが知られている。例えばフェルラ酸とカフ
ェ酸が良い例である。また抗酸化性物質の持つ新しい機
能として、ο−ジヒドロキシ構造を有するＮＤＧＡやケ
ルセチンなどがアラキドン酸カスケードにおける５−リ
ポキシゲナーゼ阻害に重要な役割を果すことが注目され
ている。Generally, phenolic antioxidants are ο-
It is known that having a dihydroxy structure enhances its activity. For example, ferulic acid and caffeic acid are good examples. As a new function of antioxidants, it has been noted that NDGA and quercetin having a o-dihydroxy structure play an important role in inhibiting 5-lipoxygenase in the arachidonic acid cascade.
【０００４】[0004]
【発明により解決すべき課題】この発明の発明者らは、
多くの生理活性を有するクルクミンに着目し、これまで
抗酸化性をはじめ、数々の研究を行つた。またクルクミ
ンを脱メチル化することによりο−ジヒドロオキシ構造
を有するクルクミノイドを調整し、その生理活性につい
て検討を加え応用・開発への基礎を確立することを課題
とした。DISCLOSURE OF THE INVENTION Problems to be Solved by the Invention
Focusing on curcumin, which has many physiological activities, we have conducted a number of studies, including antioxidant activity. In addition, the subject was to prepare curcuminoids having o-dihydroxy structure by demethylating curcumin, to study its physiological activity, and to establish the basis for application and development.
【０００５】[0005]
【課題を解決する為の手段】前記課題のために、無水ジ
クロロメタン中で、クルクミンに三臭化ほう素（ＢＢｒ
3 ）を作用させ、−７０℃で１０分間反応後約０℃に戻
し、水を加えて反応を止め、酢酸エチル抽出後 ＴＬＣ ＣＨＣｌ3 ：ＭｅＯＨ：ＡｃＯＨ＝１９：１：
０．２ で単離して生成物を得てこの発明を完成させた。即ちこ
の発明は次の化学式で示すο−ジヒドロキシ構造を有す
るクルクミノイドとしたクルクミン脱メチル化新規化合
物である。[Means for Solving the Problems] To solve the above problems, curcumin is added to boron tribromide (BBr) in anhydrous dichloromethane.
3), react at -70 ° C for 10 minutes, then return to about 0 ° C, add water to stop the reaction, and extract with ethyl acetate. TLC CHCl 3 : MeOH: AcOH = 19: 1:
Completed the invention with isolation at 0.2 to give the product. That is, the present invention is a novel curcumin demethylated compound which is a curcuminoid having an o-dihydroxy structure represented by the following chemical formula.
【０００６】[0006]
【化２】 [Chemical 2]
【０００７】また方法の発明は無水ジクロロメタン中で
クルクミンに三臭化ほう素（ＢＢｒ3 ）を作用させ、−
７０℃で１０分間反応させた後、０℃に戻して反応を止
め、水を加えついで酢酸エチルで抽出することを特徴と
したクルクミン脱メチル化新規化合物の製造方法であ
る。The invention of the method is also the reaction of curcumin with boron tribromide (BBr 3 ) in anhydrous dichloromethane,
A method for producing a novel curcumin demethylated compound, which comprises reacting at 70 ° C. for 10 minutes, returning to 0 ° C. to stop the reaction, adding water and then extracting with ethyl acetate.
【０００８】前記のようにして単離した生成物を用い
て、分光光度計、ＨＰＬＣの機器分析の検討を行い抗酸
化性の検討として （１） ミクロソーム−ＮＡＤΡＨ系 （２） ミクロソーム−ｔ−ＢｕＯＯＨ系による脂質過
酸化反応に対する阻害活性を測定した。Using the product isolated as described above, the spectrophotometer and the HPLC are analyzed for instrumental analysis. As a study of the antioxidant property, (1) Microsome-NADΡ H system (2) Microsome-t-BuOOH The inhibitory activity against lipid peroxidation by the system was measured.
【０００９】また生理活性の検討として （１） ５−リポキシゲナーゼ阻害活性 （２） チロシナーゼ阻害活性を測定した。As a study of physiological activity, (1) 5-lipoxygenase inhibitory activity (2) tyrosinase inhibitory activity was measured.
【００１０】先づ無水ジクロロメタン中でクルクミンに
三臭化ほう素（ＢＢｒ3 ）を作用させて、−７０℃で１
０分間反応後、約０℃に戻して水を加えて反応を止め、
酢酸エチルで抽出し、ＴＬＣで単離した。この生成物は
ＮＭＲによる構造式解析の結果化学式２のジヒドロキシ
クルクミンと決定した（化学式５、表６、７参照）。First, by reacting curcumin with boron tribromide (BBr 3 ) in anhydrous dichloromethane, the mixture was allowed to stand at -70 ° C.
After reacting for 0 minutes, return to about 0 ° C and add water to stop the reaction.
Extracted with ethyl acetate and isolated by TLC. As a result of structural formula analysis by NMR, this product was determined to be dihydroxycurcumin of Chemical Formula 2 (see Chemical Formula 5, Tables 6 and 7).
【００１１】[0011]
【化３】 [Chemical 3]
【００１２】[0012]
【表１】 [Table 1]
【００１３】[0013]
【表２】 [Table 2]
【００１４】[0014]
【化４】 [Chemical 4]
【００１５】以下ジヒドロキシクルクミンの生理活性に
ついて次の実験をした。The following experiment was conducted on the physiological activity of dihydroxycurcumin.
【００１６】[0016]
【実験１】ジヒドロキシクルクミンの抗酸化性について
の測定実験[Experiment 1] Measurement experiment on the antioxidant property of dihydroxycurcumin
【００１７】（１） ミクロソーム−ＮＡＤＰＨ系を用
いて阻害活性の測定 （反応条件） ミクロソーム ０．２５ｍｇProtein ／ｍｌ ＮＡＤＰＨ ０．５ｍＭ サンプル（ＤＭＳＯ）２．５μＭ ０．１Ｍリン酸buffer（ｐＨ７．４） 前記に付３７℃で３０分間インキュベートした後ＴＢＡ
法により阻害活性を測定した。(1) Measurement of Inhibitory Activity Using Microsome-NADPH System (Reaction Conditions) Microsome 0.25 mg Protein / ml NADPH 0.5 mM Sample (DMSO) 2.5 μM 0.1 M Phosphate buffer (pH 7.4) After incubating at 37 ℃ for 30 minutes
The inhibitory activity was measured by the method.
【００１８】（測定結果）前記実験の後、表１の結果を
得た。(Measurement Results) After the above experiment, the results shown in Table 1 were obtained.
【００１９】[0019]
【表３】 [Table 3]
【００２０】前記により明らかなように、過酸化に関与
する金属（Ｆｅ）のキレート力について見ることができ
た。As is clear from the above, the chelating ability of the metal (Fe) involved in peroxidation could be seen.
【００２１】（２） ミクロソーム−ｔ−ＢｕＯＯＨ系
を用いて脂質過酸化反応に対する阻害活性の測定 （反応条件） ミクロソーム ０．２５ｍｇProtein ／ｍｌ ｔ−ＢｕＯＯＨ ５．０ｍＭ サンプル（ＤＭＳＯ）１０μＭ ０．１Ｍリン酸buffer（ｐＨ７．４） 前記に付３７℃で３０分間インキュベートした後ＴＢＡ
で脂質過酸化反応に対する阻害活性を測定した。(2) Measurement of Inhibitory Activity Against Lipid Peroxidation Reaction Using Microsome-t-BuOOH System (Reaction Conditions) Microsome 0.25 mg Protein / ml t-BuOOH 5.0 mM Sample (DMSO) 10 μM 0.1 M Phosphate buffer (pH 7.4) TBA after incubation at 37 ° C for 30 minutes
The inhibitory activity against lipid peroxidation was measured by.
【００２２】（測定結果）前記実験の後、表２を得た。(Measurement Results) Table 2 was obtained after the above experiment.
【００２３】[0023]
【表４】 [Table 4]
【００２４】（結論）前記により明らかなようにキレー
ト剤を入れても過酸化を抑制できなかったことから、フ
ェントン（Fenton）型で生じる・ＯＨなどの捕捉をして
いると考えられる。(Conclusion) As apparent from the above, even if the chelating agent was added, the peroxidation could not be suppressed, and it is considered that the OH and the like generated in the Fenton type are captured.
【００２５】[0025]
【実験２】 ５−リポキシゲナーゼ（５−ＬＯ）阻害活性についての
測定実験 （実験条件）活性測定は、大腸菌によつて培養されたヒ
トの５−ＬＯを、アラキドン酸と反応させ、５−Ｈ
（Ｐ）ＥＴＥの生成量をＨＰＬＣで定量して行つた。[Experiment 2] Measurement experiment for 5-lipoxygenase (5-LO) inhibitory activity (experimental condition) The activity was measured by reacting human 5-LO cultured with E. coli with arachidonic acid to give 5-H.
The amount of (P) ETE produced was quantified by HPLC.
【００２６】これらのピークは、Retention time約２７
分に検出され、阻害物質を添加した時の減少量から阻害
率を求めて比較した（図１、図２）。These peaks have a retention time of about 27.
The inhibitory rate was determined from the amount of reduction detected when the inhibitor was added, and the results were compared (FIGS. 1 and 2).
【００２７】（測定結果）前記を測定した結果表３を得
た。クルクミノイドについては２．５μＭ（最終濃度あ
り対照としたカフェ酸は１０倍量の２５μＭでも全く阻
害を示さなかつた。(Measurement Results) As a result of the above measurement, Table 3 was obtained. For curcuminoids, 2.5 μM (final concentration of caffeic acid as a control did not show any inhibition even at 10-fold amount of 25 μM).
【００２８】[0028]
【表５】 [Table 5]
【００２９】前記におけるリポキシゲナーゼの阻害はフ
ェノール性水酸基によるリポキシゲナーゼ中のＦｅの還
元であると考えられている。Ｆｅ3+状態で活性型のリポ
キシゲナーゼは、不飽和脂肪酸（ＬＨ）とコンプレック
スを作る過程で還元されるがその前にフェノール類が存
在すると、フェノール類が存在するとフェノール性水酸
基の電子供与性により還元される。不活性化型Ｆｅ2+に
なつてしまう。従つてフェノール類のリポキシゲナーゼ
阻害活性の強さは、このＦｅ3+→Ｆｅ2+への還元力に関
係があると考えられる。そこでチトクロームＣにより還
元力の測定を行うことにより活性との相関をみた。The inhibition of lipoxygenase described above is considered to be the reduction of Fe in lipoxygenase by the phenolic hydroxyl group. Active lipoxygenase in the Fe 3+ state is reduced in the process of forming a complex with unsaturated fatty acid (LH), but if phenols are present before it, it is reduced by the electron donating property of the phenolic hydroxyl group if phenols are present. To be done. It becomes inactivated Fe 2+ . Therefore, it is considered that the strength of the lipoxygenase inhibitory activity of phenols is related to the reducing power of Fe 3+ → Fe 2+ . Then, the correlation with the activity was observed by measuring the reducing power with cytochrome C.
【００３０】フェノール類によるリポキシゲナーゼの阻
害メカニズムを化学式３で示す。A chemical formula 3 shows the mechanism of inhibition of lipoxygenase by phenols.
【００３１】[0031]
【化５】 [Chemical 5]
【００３２】即ちチトクロームＣの還元力による５−リ
ポキシゲナーゼ阻害活性化の結果は表４の通りである。That is, Table 4 shows the results of 5-lipoxygenase inhibition activation by the reducing power of cytochrome C.
【００３３】[0033]
【表６】 [Table 6]
【００３４】[0034]
【実験３】 チロシナーゼ阻害活性についての測定実験 チロシナーゼは、分子内にオキシゲナーゼと、オキシダ
ーゼの両方をもつ混合物で、分子内にＣｕを含む金属酵
素であり、Ｃｕ+ ←→Ｃｕ2+の変化が酵素の活性化と基
質の酸化に関係している。[Experiment 3] Measurement experiment on tyrosinase inhibitory activity Tyrosinase is a mixture having both oxygenase and oxidase in the molecule, is a metal enzyme containing Cu in the molecule, and changes in Cu + ← → Cu 2+ are enzymes. Is involved in the activation of and substrate oxidation.
【００３５】このチロシナーゼによつて生成するメラニ
ンは、紫外線から皮膚を守るために作られ細胞のダメー
ジを防ぐことができる。前記メラニンは色黒のもとであ
り、しみや老人性ほくろのもとになる物質だが合成と分
解のバランスが保たれている。しかしながらそのバラン
スがくずれると、メラニン過剩蓄積が起り、しみやそば
かす、老人性色素斑などの原因となる。その際にメラニ
ン生成を抑制することは重要であり、多くの研究もなさ
れている。そこでチロシナーゼの阻害について検討し
た。The melanin produced by this tyrosinase is made to protect the skin from ultraviolet rays and can prevent damage to cells. The above-mentioned melanin is a source of dark black, which is a substance that causes stains and senile moles, but maintains a balance between synthesis and decomposition. However, if the balance is lost, melanin hyperproliferative accumulation occurs, which causes spots, freckles, and senile pigment spots. At that time, it is important to suppress melanin production, and many studies have been made. Therefore, inhibition of tyrosinase was examined.
【００３６】チロシナーゼはチロシンからメラニンを作
る酵素で皮膚の色素形成や野菜の褐変に重要な役割を果
している。前記チロシンからメラニンを生成するのは化
学式４の通りである。Tyrosinase is an enzyme that produces melanin from tyrosine, and plays an important role in skin pigmentation and browning of vegetables. The formation of melanin from tyrosine is represented by Chemical Formula 4.
【００３７】[0037]
【化６】 [Chemical 6]
【００３８】（反応条件） チロシン １．０ｍＭ チロシナーゼ ５０ units／ｍｌ サンプル（ＤＭＳＯ）１０μｌ ０．１Ｍリン酸buffer（ｐＨ７．４） 上記をインキュベートにて２５℃で反応させた後、ＴＣ
Ａを加えて反応停止し、内標としてドーパミンを添加し
た。(Reaction conditions) Tyrosine 1.0 mM Tyrosinase 50 units / ml Sample (DMSO) 10 μl 0.1 M phosphate buffer (pH 7.4) After reacting the above at 25 ° C. by incubation, TC
The reaction was stopped by adding A, and dopamine was added as an internal standard.
【００３９】前記におけるチロシナーゼは、メラノーマ
（黒色腫、メラノサイトの悪性腫瘍）のマーカーとして
知られているため、その生成抑制は抗ガンの立場からも
重要であると考えられた。Since the above-mentioned tyrosinase is known as a marker for melanoma (melanoma, malignant tumor of melanocyte), its production suppression was considered to be important from the standpoint of anti-cancer.
【００４０】前記チロシナーゼの阻害を、メラニン生成
段階の第一生成物であるＤＯＰＡの生成阻害を指標に検
討した。前記により反応させ、ＨＰＬＣにより定量し
た。The inhibition of tyrosinase was examined using the inhibition of the production of DOPA, which is the first product in the melanin production stage, as an index. The reaction was performed according to the above, and quantified by HPLC.
【００４１】内部標準は２ｍＭのドーパミンを１０μｌ
添加した（図５、図６）。The internal standard was 10 μl of 2 mM dopamine.
Was added (FIG. 5, FIG. 6).
【００４２】表５の結果を得た。The results shown in Table 5 were obtained.
【００４３】[0043]
【表７】 [Table 7]
【００４４】前記のようにクルクミンに対して阻害率は
明らかに増強された。As described above, the inhibition rate was clearly enhanced with respect to curcumin.
【００４５】[0045]
【実験例４】これまでメラニン生成抑制を、チロシンか
ら一番最初に生成するドーパ（ＤＯＰＡ）の生成量の減
少によつて評価してきた。これはチロシナーゼに含まれ
るオキシゲナーゼ活性の阻害に着目して検討を行つたの
である。今度はもう一つの活性型であるオキシダーゼ活
性に着目し、メラニン生成抑制について検討した。即ち
ドーパを基質として生成するドーパークロムの生成量の
減少によつて、メラニン生成抑制の指標としたのであ
る。[Experimental Example 4] Up to now, suppression of melanin production has been evaluated by reducing the amount of dopa (DOPA) produced from tyrosine at the very beginning. This was conducted by focusing on the inhibition of oxygenase activity contained in tyrosinase. Next, we focused on another activity type, oxidase activity, and examined suppression of melanin production. That is, the decrease in the amount of doperchrome produced using dopa as a substrate was used as an index for suppressing melanin production.
【００４６】 （反応条件） ドーパ ５ｍＭ ８０μｌ バッファー０．１Ｍリン酸buffer ＰＨ７．４ ６００μｌ サンプル（ＤＭＳＯ溶液） ４０μｌ チロシナーゼ（５００ units／ｍｌ） ８０μｌ 上記の反応液を素早く混合し、ドーパクロムの最大吸収
波長４７５ｎｍで、ドーパの生成量を測定した。(Reaction conditions) Dopa 5 mM 80 μl buffer 0.1 M phosphate buffer PH 7.4 600 μl sample (DMSO solution) 40 μl tyrosinase (500 units / ml) 80 μl Then, the production amount of dopa was measured.
【００４７】阻害率は、図３の回帰直線を求めてその傾
き（ΔＡ４７５／sec ）の比較から求めた。The inhibition rate was determined by finding the regression line in FIG. 3 and comparing the slopes (ΔA475 / sec).
【００４８】[0048]
【実験例５】Ｕ1 （クルクミン）のジヒドロキシ体のド
ーパからドーパクロムの阻害活性を求めた所、図３の通
りである。即ちドーパを基質にドーパクロムへの阻害活
性は、Ｕ1 に較べてジヒドロキシ体ははるかに強力であ
った。このことはジヒドロキシクルクミンのメラニン合
成阻害物質としての可能性を強く示唆するものである
（図４）。[Experimental Example 5] The inhibitory activity of dopachrome was determined from the dopa of dihydroxy form of U1 (curcumin). That is, the inhibitory activity against dopachrome using dopa as a substrate was much stronger in the dihydroxy form than in U1. This strongly suggests the possibility of dihydroxycurcumin as an inhibitor of melanin synthesis (Fig. 4).
【００４９】[0049]
【発明の効果】この発明におけるクルクミン脱メチル化
新規化合物であるジヒドロキシクルクミンは、ミクロソ
ーム−ＮＡＤＰＨ系やミクロソーム−ｔ−ＢｕＯＯＨ系
を用いて阻害活性の測定の結果は、クルクミンと較べて
優れた結果が得られ、抗酸化性が強い効果がある。INDUSTRIAL APPLICABILITY Dihydroxycurcumin, which is a novel compound for demethylating curcumin according to the present invention, is superior to curcumin in the measurement of its inhibitory activity using the microsome-NADPH system and the microsome-t-BuOOH system. It is obtained and has a strong antioxidative effect.
【００５０】又酸化還元酵素のリポキシゲナーゼの阻害
活性もクルクミンと較べて優れた結果が得られ、さらに
チロシナーゼ阻害活性もクルクミンとの比較において優
れている。即ちこの発明のジヒドロキシクルクミンは、
クルクミンより抗酸化性や抗炎症性に優れている。また
チロシナーゼにより生成されるメラニンは、しみやそば
かす、老人性色素斑などの原因となり、このジヒドロキ
シクルクミンによってメラニン生成を抑制できること
は、美容面や老化制御において大変有意義である。Further, excellent results were obtained with respect to the lipoxygenase inhibitory activity of oxidoreductase as compared with curcumin, and the tyrosinase inhibitory activity was also superior as compared with curcumin. That is, the dihydroxycurcumin of this invention is
It has superior antioxidant and anti-inflammatory properties to curcumin. In addition, melanin produced by tyrosinase causes spots, freckles, senile pigment spots, etc. The ability to suppress melanin production by this dihydroxycurcumin is very significant in terms of cosmetics and aging control.
【００５１】またその特性を利用し、化粧品や、食品な
どの添加物として品質保持上優れている。Further, by utilizing its characteristics, it is excellent in quality preservation as an additive for cosmetics and foods.
【図１】ヒト５−リポキシゲナーゼにより生成された５
−Ｈ（Ｐ）ＥＴＥのコントロールのＨＰＬＣクロマトグ
ラム。FIG. 1 5 produced by human 5-lipoxygenase
-H (P) ETE control HPLC chromatogram.
【図２】ヒト５−リポキシゲナーゼにより生成された５
−Ｈ（Ｐ）ＥＴＥの阻害剤によるＨＰＬＣクロマトグラ
ム。FIG. 2. 5 produced by human 5-lipoxygenase
-HPLC chromatogram with an inhibitor of H (P) ETE.
【図３】阻害剤によるドーパ生成阻害率の効果図。FIG. 3 is an effect graph of the dopa production inhibition rate by the inhibitor.
【図４】他の抗酸化物と、ジヒドロキシクルクミンのド
ーパからドーパクロムへの阻害活性比較図。FIG. 4 is a comparative diagram showing the inhibitory activity of other antioxidants and dihydroxycurcumin from dopa to dopachrome.
【図５】ＨＰＬＣによるチロシンの測定図。FIG. 5: Tyrosine measurement diagram by HPLC.
【図６】ＨＰＬＣによるチロシンとドーパの相関図。FIG. 6 is a correlation diagram of tyrosine and dopa by HPLC.
フロントページの続き (51)Int.Cl.6 識別記号 庁内整理番号 ＦＩ 技術表示箇所 Ｃ０９Ｋ 15/06 Continuation of front page (51) Int.Cl. 6 Identification number Office reference number FI technical display area C09K 15/06
Claims (2)
を有するクルクミノイドとしたクルクミン脱メチル化新
規化合物。 【化１】 1. A novel curcumin demethylated compound which is a curcuminoid having an o-dihydroxy structure represented by the following chemical formula. [Chemical 1]
臭化ほう素（ＢＢｒ3 ）を作用させ、−７０℃で１０分
間反応させた後、０℃に戻して水を加えて反応を止め、
ついで酢酸エチルで抽出することを特徴としたクルクミ
ン脱メチル化新規化合物の製造方法。2. Curcumin is reacted with boron tribromide (BBr 3 ) in anhydrous dichloromethane and reacted at −70 ° C. for 10 minutes, then returned to 0 ° C. and water is added to stop the reaction.
Then, a method for producing a new compound of curcumin demethylation, which comprises extracting with ethyl acetate.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007043058A1 (en) * | 2005-10-13 | 2007-04-19 | Ganga Raju Gokaraju | Process for producing enriched fractions of tetrahydroxycurcumin and tetrahydrotetrahydroxy-curcumin from the extracts of curcuma longa |
| KR100759467B1 (en) * | 2006-06-23 | 2007-10-04 | 한국생명공학연구원 | Composition for prevention and treatment of anti-gout containing a compound isolated from inonotus obliquus or phellinus baumi |
| JP2008516954A (en) * | 2004-10-15 | 2008-05-22 | ユニヴァーシティ・オヴ・ノース・キャロライナ・アト・チャペル・ヒル | Novel curcumin analogs and uses thereof |
| US8772252B2 (en) | 2011-01-27 | 2014-07-08 | New York University | Coumarin compounds as melanogenesis modifiers and uses thereof |
| CN104447269A (en) * | 2014-12-05 | 2015-03-25 | 江南大学 | Compound having tyrosinase inhibitory activity and synthesis method of compound |
| JP2019503992A (en) * | 2015-11-24 | 2019-02-14 | ユニヴェルシテ デクス−マルセイユＵｎｉｖｅｒｓｉｔｅ Ｄ’Ａｉｘ−Ｍａｒｓｅｉｌｌｅ | Boron difluoride complex of curcuminoid compound, its production method and use |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03240735A (en) * | 1990-02-05 | 1991-10-28 | Pt Darya Varia Lab | Combination of compounds as anti- inflammatory agent isolated from turmeric spp |
-
1994
- 1994-01-14 JP JP6002837A patent/JP2663239B2/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03240735A (en) * | 1990-02-05 | 1991-10-28 | Pt Darya Varia Lab | Combination of compounds as anti- inflammatory agent isolated from turmeric spp |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8198323B2 (en) | 2002-04-17 | 2012-06-12 | The University Of North Carolina At Chapel Hill | Curcumin analogues and uses thereof |
| JP2008516954A (en) * | 2004-10-15 | 2008-05-22 | ユニヴァーシティ・オヴ・ノース・キャロライナ・アト・チャペル・ヒル | Novel curcumin analogs and uses thereof |
| WO2007043058A1 (en) * | 2005-10-13 | 2007-04-19 | Ganga Raju Gokaraju | Process for producing enriched fractions of tetrahydroxycurcumin and tetrahydrotetrahydroxy-curcumin from the extracts of curcuma longa |
| JP2009511573A (en) * | 2005-10-13 | 2009-03-19 | ゴカラジュ， ガンガ， ラジュ | Process for producing tetrahydroxycurcumin enriched fraction and tetrahydrotetrahydroxycurcumin enriched fraction from curcuma longa extract |
| AU2005337331B2 (en) * | 2005-10-13 | 2011-10-20 | Laila Nutraceuticals | Process for producing enriched fractions of tetrahydroxycurcumin and tetrahydrotetrahydroxy-curcumin from the extracts of curcuma longa |
| KR100759467B1 (en) * | 2006-06-23 | 2007-10-04 | 한국생명공학연구원 | Composition for prevention and treatment of anti-gout containing a compound isolated from inonotus obliquus or phellinus baumi |
| US8772252B2 (en) | 2011-01-27 | 2014-07-08 | New York University | Coumarin compounds as melanogenesis modifiers and uses thereof |
| CN104447269A (en) * | 2014-12-05 | 2015-03-25 | 江南大学 | Compound having tyrosinase inhibitory activity and synthesis method of compound |
| JP2019503992A (en) * | 2015-11-24 | 2019-02-14 | ユニヴェルシテ デクス−マルセイユＵｎｉｖｅｒｓｉｔｅ Ｄ’Ａｉｘ−Ｍａｒｓｅｉｌｌｅ | Boron difluoride complex of curcuminoid compound, its production method and use |
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|---|---|
| JP2663239B2 (en) | 1997-10-15 |
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