TWI583404B - A method for manufacturing a 7,3',4'-trihydroxyisoflavone composition - Google Patents
A method for manufacturing a 7,3',4'-trihydroxyisoflavone composition Download PDFInfo
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本發明係關於一種7,3’,4’-大豆異黃酮製劑的製備方法，特別關於一種7,3’,4’-大豆異黃酮製劑的製備方法，其可以提升7,3’,4’-大豆異黃酮之溶解度者。 The invention relates to a preparation method of a 7,3',4'-soy isoflavone preparation, in particular to a preparation method of a 7,3',4'-soy isoflavone preparation, which can improve 7,3', 4' - Solubility of soy isoflavones.
7,3’,4’-大豆異黃酮(7,3’,4’-trihydroxyisoflavone)之IUPAC命名係為3-(3,4-二羥基苯基)-7-羥基苯並吡喃-4-酮(3-(3,4-dihydroxyphenyl)-7-hydroxychromen-4-one)，其結構如第1圖所示。7,3’,4’-大豆異黃酮係為一種植物性***，主要來源係為黃豆等植物中，其具有抗氧化、抗發炎及美白等活性，可以添加於化妝品中，以避免氧化壓力所造成的皮膚老化及水份喪失。 The IUPAC nomenclature of 7,3',4'-steatrienoflavone is 3-(3,4-dihydroxyphenyl)-7-hydroxybenzopyran-4- 3-(3,4-dihydroxyphenyl)-7-hydroxychromen-4-one, the structure of which is shown in Fig. 1. 7,3',4'-soy isoflavones are a kind of phytoestrogens. The main source is soybeans and other plants. It has antioxidant, anti-inflammatory and whitening activities and can be added to cosmetics to avoid oxidative stress. Caused by skin aging and loss of moisture.
惟，7,3’,4’-大豆異黃酮的水溶解度差，故而難以為皮膚有效吸收，而影響其生理可用率。因此，有必要提供一種7,3’,4’-大豆異黃酮製劑的製備方法，以改善其水溶解度不良之問題。 However, the water solubility of 7,3',4'-soy isoflavones is poor, so that it is difficult to effectively absorb the skin and affect its physiological availability. Therefore, it is necessary to provide a preparation method of a 7,3',4'-soy isoflavone preparation to improve the problem of poor water solubility.
本發明之主要目的係提供一種7,3’,4’-大豆異黃酮製劑的製備方法，其可以製備一7,3’,4’-大豆異黃酮製劑，且該7,3’,4’-大豆異黃酮製劑相較於7,3’,4’-大豆異黃酮具有較佳水溶解度者。 The main object of the present invention is to provide a preparation method of a 7,3',4'-soy isoflavone preparation, which can prepare a 7,3',4'-soy isoflavone preparation, and the 7,3', 4' The soy isoflavone preparation has better water solubility than the 7,3',4'-soy isoflavone.
本發明提供一種7,3’,4’-大豆異黃酮製劑的製備方法，係包含：提供一混合物，係由7,3’,4’-大豆異黃酮與一助溶劑所組成，該助溶劑 係為聚乙烯基吡咯烷酮；及以球磨法研磨該混合物，以製得一7,3’,4’-大豆異黃酮製劑，該7,3’,4’-大豆異黃酮製劑之粒徑係介於10~1000nm之範圍。 The present invention provides a process for the preparation of a 7,3',4'-soy isoflavone formulation comprising: providing a mixture consisting of 7,3',4'-soy isoflavones and a cosolvent, the cosolvent Is a polyvinylpyrrolidone; and grinding the mixture by ball milling to prepare a 7,3',4'-soy isoflavone preparation, the particle size of the 7,3',4'-soy isoflavone preparation In the range of 10~1000nm.
本發明之7,3’,4’-大豆異黃酮製劑的製備方法，其中，係以行星式球磨機研磨該混合物。 The method for producing a 7,3',4'-soy isoflavone preparation of the present invention, wherein the mixture is ground in a planetary ball mill.
本發明之7,3’,4’-大豆異黃酮製劑的製備方法，其中，該混合物係由以重量百分比計3.3~10%之7,3’,4’-大豆異黃酮及90~96.7%之該助溶劑所組成。 The preparation method of the 7,3',4'-soy isoflavone preparation of the invention, wherein the mixture is from 3.3 to 10% by weight of 7,3', 4'-soy isoflavone and 90 to 96.7% by weight. The solvent is composed of the cosolvent.
本發明之7,3’,4’-大豆異黃酮製劑的製備方法，其中，該混合物係由以重量百分比計3.3%之7,3’,4’-大豆異黃酮及96.7%之該助溶劑所組成。 The preparation method of the 7,3',4'-soy isoflavone preparation of the invention, wherein the mixture is 3.3% by weight of 7,3',4'-soy isoflavone and 96.7% of the cosolvent Composed of.
本發明之7,3’,4’-大豆異黃酮製劑製備方法，藉由使用該吡咯烷酮衍生物做為該助溶劑，係可以透過研磨方式製備具有較小粒徑之該7,3’,4’-大豆異黃酮製劑。藉此，本發明所製備之該7,3’,4’-大豆異黃酮製劑係具有良好的水溶性，達到提升7,3’,4’-大豆異黃酮的生體可用率之功效。 The preparation method of the 7,3',4'-soy isoflavone preparation of the invention, by using the pyrrolidone derivative as the auxiliary solvent, the 7, 3', 4 having a smaller particle size can be prepared by grinding. '-Soy isoflavone preparation. Thereby, the 7,3',4'-soy isoflavone preparation prepared by the present invention has good water solubility and has the effect of improving the bioavailability of 7,3',4'-soy isoflavone.
第1圖：係7,3’,4’-大豆異黃酮之結構圖。 Fig. 1 is a structural diagram of 7,3',4'-soy isoflavones.
第2圖：係聚乙烯基吡咯烷酮之結構圖。 Figure 2: Structure diagram of polyvinylpyrrolidone.
第3圖：係第A1~A3組之平均粒徑分析結果。 Figure 3: The results of the average particle size analysis of Groups A1 to A3.
第4a圖：係第B1~B6組之西方點墨圖譜。 Figure 4a: The western dot blot of the B1~B6 group.
第4b圖：係第B1~B6組之COX-2表現量長條圖。 Figure 4b: Bar graph of COX-2 performance in Groups B1~B6.
第5a圖：係第C1~C6組之西方點墨圖譜。 Figure 5a: Western blotting map of the C1~C6 group.
第5b圖：係第C1~C6組之COX-2表現量長條圖。 Figure 5b: Bar graph of COX-2 performance in Groups C1~C6.
第6圖：係第D1~D6組之DPPH自由基清除率長條圖。 Figure 6: Bar graph of DPPH free radical scavenging rate in groups D1 to D6.
第7圖：係第D1~D6組之清除DPPH自由基半數有效濃度長條圖。 Figure 7: Bar graph of the half effective concentration of DPPH free radicals in groups D1 to D6.
為讓本發明之上述及其他目的、特徵及優點能更明顯易懂，下文特舉本發明之較佳實施例，並配合所附圖式，作詳細說明如下：本發明之7,3’,4’-大豆異黃酮製劑的製備方法，係將7,3’,4’-大豆異黃酮與一助溶劑混合，續以球磨法進行研磨，以製備具有良好水溶性之一7,3’,4’-大豆異黃酮製劑。 The above and other objects, features and advantages of the present invention will become more <RTIgt; The preparation method of 4'-soy isoflavone preparation is to mix 7,3', 4'-soy isoflavone with a co-solvent and continue grinding by ball milling to prepare one of the water-soluble ones 7,3', 4 '-Soy isoflavone preparation.
本發明所述之7,3’,4’-大豆異黃酮係可以自大豆等植物中萃取，或者直接購買商業來源之7,3’,4’-大豆異黃酮，但不以此為限。一般市售之7,3’,4’-大豆異黃酮係為粉末狀，且其平均粒徑約為4000~6000nm。 The 7,3',4'-soy isoflavones of the present invention may be extracted from plants such as soybeans, or commercially available 7,3',4'-soy isoflavones, but not limited thereto. The commercially available 7,3',4'-soy isoflavones are in the form of a powder and have an average particle diameter of about 4,000 to 6,000 nm.
該助溶劑係為一吡咯烷酮衍生物，係指包含吡咯烷酮結構之化合物，可以為單體或聚合物等。藉由吡咯烷酮之結構，可以包覆7,3’,4’-大豆異黃酮，並維持其穩定性。於本發明一實施例中，該助溶劑係為聚乙烯基吡咯烷酮(polyethenylpyrrolidinone)，其結構係如第2圖所示。藉由聚乙烯基吡咯烷酮之聚合結構，可以更進一步幫助分散7,3’,4’-大豆異黃酮。 The cosolvent is a pyrrolidone derivative, and means a compound containing a pyrrolidone structure, and may be a monomer or a polymer. By the structure of pyrrolidone, 7,3', 4'-soy isoflavone can be coated and its stability is maintained. In one embodiment of the invention, the co-solvent is polyvinylethrrolidone (polyethenylpyrrolidinone), the structure of which is shown in Figure 2. The dispersion of 7,3',4'-soy isoflavones can be further assisted by the polymeric structure of polyvinylpyrrolidone.
詳言之，本發明之7,3’,4’-大豆異黃酮製劑的製備方法係先將7,3’,4’-大豆異黃酮及該助溶劑混合以獲得一混合物，續以球磨機研磨該混合物，以製得粒徑介於10~1000nm之範圍的該7,3’,4’-大豆異黃酮製劑。上述球磨機係可以為直線式球磨機或行星式球磨機等，本發明不加以限制。於本實施例中，係以行星式球磨機進行研磨，其所需時間較短，且研磨後該混合物之粒徑較為均勻。 In particular, the 7,3',4'-soy isoflavone preparation of the present invention is prepared by first mixing 7,3',4'-soy isoflavones and the co-solvent to obtain a mixture, which is continuously ground by a ball mill. The mixture is prepared to prepare the 7,3', 4'-soy isoflavone preparation having a particle size ranging from 10 to 1000 nm. The above ball mill may be a linear ball mill or a planetary ball mill, etc., and the invention is not limited. In the present embodiment, the grinding is carried out by a planetary ball mill, which takes a short time and the particle size of the mixture is relatively uniform after grinding.
由於該助溶劑可以包覆7,3’,4’-大豆異黃酮，以穩定該7,3’,4’-大豆異黃酮製劑之結構，其不會在研磨後再度聚集成為粒徑較大之分子，因此，本發明之7,3’,4’-大豆異黃酮製劑的製備方法，可以製備具有較小粒徑之該7,3’,4’-大豆異黃酮製劑，以提升該7,3’,4’-大豆異黃酮製劑 之溶解度，進而提升其生體可用率。 Since the co-solvent can coat 7,3',4'-soy isoflavones to stabilize the structure of the 7,3',4'-soy isoflavone preparation, it does not re-aggregate after grinding to a larger particle size. Molecule, therefore, the preparation method of the 7,3',4'-soy isoflavone preparation of the present invention can prepare the 7,3',4'-soy isoflavone preparation having a smaller particle size to enhance the 7 , 3', 4'-soy isoflavone preparation The solubility, which in turn increases its bioavailability.
為證實經由本發明之7,3’,4’-大豆異黃酮製劑的製備方法確實可以獲得具有較小粒徑之該7,3’,4’-大豆異黃酮製劑，且該7,3’,4’-大豆異黃酮製劑相較於7,3’,4’-大豆異黃酮具有較佳水溶性及生體可用率，遂進行以下實驗。 In order to confirm that the preparation method of the 7,3',4'-soy isoflavone preparation of the present invention can surely obtain the 7,3',4'-soy isoflavone preparation having a smaller particle diameter, and the 7,3' The 4'-soy isoflavone preparation has better water solubility and bioavailability than the 7,3', 4'-soy isoflavone preparation, and the following experiment was carried out.
(A)7,3’,4’-大豆異黃酮製劑之粒徑測試 (A) Particle size test of 7,3',4'-soy isoflavone preparation
以聚乙烯基吡咯烷酮做為該助溶劑，分別以不同比例混合市售之7,3’,4’-大豆異黃酮(平均粒徑約為4850nm)，以製備第A1~A3組之該7,3’,4’-大豆異黃酮製劑，各組之添加比例係如下第1表所示。本實驗係以RetschGmbh Type：PM100之行星式球磨機進行研磨，設定轉速每分鐘400轉，研磨時間20分鐘。 Using polyvinylpyrrolidone as the co-solvent, commercially available 7,3',4'-soy isoflavones (average particle diameter of about 4850 nm) were mixed in different ratios to prepare the 7th group of A1~A3 groups. The 3', 4'-soy isoflavone preparation, the addition ratio of each group is shown in Table 1 below. The experiment was carried out with a planetary ball mill of RetschGmbh Type: PM100, setting the rotation speed at 400 rpm and grinding time for 20 minutes.
本實驗中，係以粒徑分析儀zetasizer 3000Has(Malvern Instruments)。分別針對第A1~A3組進行三次測量後，取其平均粒徑記錄如第3圖。由上述結果可以得知，本發明藉由添加該吡咯烷酮衍生物作為該助溶劑，係可以經由研磨有效降低該7,3’,4’-大豆異黃酮製劑之粒徑，以生成粒徑大小介於10~1000nm之7,3’,4’-大豆異黃酮。 In this experiment, a particle size analyzer zetasizer 3000Has (Malvern Instruments) was used. After three measurements were made for the A1~A3 group, the average particle size was recorded as shown in Fig. 3. It can be seen from the above results that the present invention can effectively reduce the particle size of the 7,3',4'-soy isoflavone preparation by grinding by adding the pyrrolidone derivative as the cosolvent to form a particle size. 7,3',4'-soy isoflavones at 10~1000nm.
(B)7,3’,4’-大豆異黃酮製劑之溶解度測試 (B) Solubility test of 7,3',4'-soy isoflavone preparation
精秤1mg未經處理之7,3’,4’-大豆異黃酮(第A0組)，及包含等量7,3’,4’-大豆異黃酮之上述第A1~A3組該7,3’,4’-大豆異黃酮製劑，分別溶解於1ml之純水溶液中，震盪10分鐘。續以孔徑為0.45μm之濾 膜過濾，並以HPLC分析其7,3’,4’-大豆異黃酮含量，以測試第A0~A4組之溶解度，記錄結果如下第2表所示。 1 mg of untreated 7,3',4'-soy isoflavones (Group A0), and the above A1~A3 group containing equal amounts of 7,3',4'-soy isoflavones 7,3 The ',4'-soy isoflavone preparation was dissolved in 1 ml of pure aqueous solution and shaken for 10 minutes. Continued filtration with a pore size of 0.45 μm The membrane was filtered, and the 7,3',4'-soy isoflavone content was analyzed by HPLC to test the solubility of the A0 to A4 groups, and the results are shown in Table 2 below.
由上述實驗結果可以得知，本發明之7,3’,4’-大豆異黃酮製劑的製備方法，確實可以透過該助溶劑之添加，以研磨方式製備具有較小粒徑之該7,3’,4’-大豆異黃酮製劑。藉此，本發明製備之該7,3’,4’-大豆異黃酮製劑具有良好的水溶性。 It can be known from the above experimental results that the preparation method of the 7,3',4'-soy isoflavone preparation of the present invention can be prepared by grinding to prepare the 7,3 having a smaller particle size by the addition of the auxiliary solvent. ', 4'-soy isoflavone preparation. Thereby, the 7,3',4'-soy isoflavone preparation prepared by the present invention has good water solubility.
(C)7,3’,4’-大豆異黃酮製劑之抗發炎活性測試 (C) Anti-inflammatory activity test of 7,3',4'-soy isoflavone preparation
本實驗選用人類HaCaT角質細胞株，係以該7,3’,4’-大豆異黃酮製劑對該HaCaT細胞株進行前處理1小時，續加入50μg/cm2之PM2.5空氣懸浮粒子以誘發該HaCaT細胞株之COX-2發炎蛋白表現，測試該7,3’,4’-大豆異黃酮製劑對於COX-2發炎蛋白表現之抑制能力。其中，第B1~B6組係以未經製程之7,3’,4’-大豆異黃酮作為對照，而第C1~C6組係使用本發明所製備之7,3’,4’-大豆異黃酮製劑。各組之空氣懸浮粒子及7,3’,4’-大豆異黃酮添加情形係如下第3、4表所示。 In this experiment, human HaCaT keratinocyte strain was selected, and the HaCaT cell line was pretreated with the 7,3', 4'-soy isoflavone preparation for 1 hour, and 50 μg/cm 2 of PM2.5 air suspension particles were continuously added to induce The COX-2 inflammatory protein of the HaCaT cell line was tested for the ability of the 7,3',4'-soy isoflavone preparation to inhibit the expression of COX-2 inflammatory protein. Among them, the B1~B6 group uses the unprocessed 7,3',4'-soy isoflavone as a control, and the C1~C6 group uses the 7,3',4'-soybean prepared by the present invention. Flavonoid preparation. The addition of airborne particles and 7,3',4'-soy isoflavones in each group is shown in Tables 3 and 4 below.
第3表：第B1~B6組之添加情形
夲實驗係以西方點墨法偵測前述各組之COX-2發炎蛋白表現情形，並以GAPDH作為內控制組，其結果分別如第4a圖(第B1~B6組)及第5a圖(第C1~C6組)所示，另分別以第B1組及第C1組之COX-2發炎蛋白表現量作為1，各組之COX-2發炎蛋白相對表現量則分別如第4b圖(第B1~B6組)及第5b圖(第C1~C6組)所示。由實驗結果可以得知，PM2.5空氣懸浮粒子之添加可以誘發該HaCaT細胞株表現COX-2發炎蛋白，而前處理本發明所製備之7,3’,4’-大豆異黃酮製劑則能夠有效預防COX-2發炎蛋白之表現，且具有劑量依賴性。 The 夲 experiment used Western blotting to detect the performance of COX-2 inflammatory proteins in the above groups, and GAPDH was used as the internal control group. The results were as shown in Fig. 4a (Groups B1 to B6) and 5a (Parts). In the C1~C6 group, the COX-2 inflammatory protein expression in Group B1 and Group C1 was taken as 1, and the relative expression of COX-2 inflammatory protein in each group was as shown in Figure 4b (B1~). Group B6) and Figure 5b (Groups C1 to C6) are shown. It can be known from the experimental results that the addition of PM2.5 air-suspended particles can induce the HaCaT cell line to exhibit COX-2 inflammatory protein, while the pretreatment of the 7,3', 4'-soy isoflavone preparation prepared by the present invention can Effectively prevent the performance of COX-2 inflammatory protein in a dose-dependent manner.
(D)7,3’,4’-大豆異黃酮製劑之DPPH自由基清除率測試 (D) DPPH free radical scavenging test for 7,3',4'-soy isoflavone preparations
請參照第5表所示，夲實驗則係混合不同比例之7,3’,4’-大豆異黃酮及聚乙烯基吡咯烷酮後，分別以球磨及攪拌之方式製備第D1~ D6組之該7,3’,4’-大豆異黃酮製劑。 Please refer to the table 5, the experiment is to mix the different ratios of 7,3', 4'-soy isoflavones and polyvinylpyrrolidone, then prepare the D1~ by ball milling and stirring respectively. The 7,3',4'-soy isoflavone preparation of Group D6.
續吸取200μM之DPPH溶液125μl，分別混合不同濃度之第D1~D6組7,3’,4’-大豆異黃酮製劑125μl，於室溫下震盪反應30分鐘後，以ELISA reader測量各組於波長517nm之吸光值，以換算DPPH自由基清除率，紀錄結果如第6圖。另計算各組之清除DPPH自由基半數有效濃度(SC50)，如第7圖所示。 Continue to absorb 125μl of 200μM DPPH solution, mix 125μl of 7,3',4'-soy isoflavone preparations of different concentrations of D1~D6 group, shake the reaction for 30 minutes at room temperature, and measure each group at wavelength by ELISA reader. The absorbance at 517 nm was used to convert DPPH free radical scavenging rate. The results are shown in Figure 6. The half effective concentration (SC 50 ) of the DPPH free radicals of each group was also calculated, as shown in Fig. 7.
依據上述實驗結果可以得知，本發明所製備之該7,3’,4’-大豆異黃酮製劑(第D1~D3組)，相較於僅以攪拌混合之7,3’,4’-大豆異黃酮製劑(第D4~D6組)具有較好的DPPH自由基清除能力。此外，特別係以重量百分比計3.3%之7,3’,4’-大豆異黃酮混合96.7%之該助溶劑(第D3組)，其清除DPPH自由基之能力最佳。 According to the above experimental results, it can be known that the 7,3',4'-soy isoflavone preparation (Groups D1 to D3) prepared by the present invention is compared with the 7, 3', 4'- which is only mixed by stirring. Soy isoflavone preparations (Groups D4 to D6) have better DPPH free radical scavenging ability. Further, in particular, 3.3% by weight of the 7,3',4'-soy isoflavones were mixed with 96.7% of the co-solvent (Group D3), which had the best ability to scavenge DPPH radicals.
綜合上述，本發明之7,3’,4’-大豆異黃酮製劑製備方法，藉由使用該吡咯烷酮衍生物做為該助溶劑，係可以透過研磨方式製備具有較小粒徑之該7,3’,4’-大豆異黃酮製劑。藉此，本發明所製備之該7,3’,4’-大豆異黃酮製劑係具有良好的水溶性，達到提升7,3’,4’-大豆異黃酮的生體可用率之功效。 In summary, the preparation method of the 7,3',4'-soy isoflavone preparation of the present invention, by using the pyrrolidone derivative as the co-solvent, can prepare the smaller particle size by the grinding method. ', 4'-soy isoflavone preparation. Thereby, the 7,3',4'-soy isoflavone preparation prepared by the present invention has good water solubility and has the effect of improving the bioavailability of 7,3',4'-soy isoflavone.
雖然本發明已利用上述較佳實施例揭示，然其並非用以限定 本發明，任何熟習此技藝者在不脫離本發明之精神和範圍之內，相對上述實施例進行各種更動與修改仍屬本發明所保護之技術範疇，因此本發明之保護範圍當視後附之申請專利範圍所界定者為準。 Although the present invention has been disclosed using the above preferred embodiments, it is not intended to be limiting The present invention is not limited to the spirit and scope of the present invention, and various modifications and changes to the above embodiments are still within the technical scope of the present invention. Therefore, the scope of protection of the present invention is attached. The scope defined in the scope of application for patent application shall prevail.
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