CN105377232A - 来自褐色巨藻的抗氧化剂萃取物以及其获得方法 - Google Patents
来自褐色巨藻的抗氧化剂萃取物以及其获得方法 Download PDFInfo
- Publication number
- CN105377232A CN105377232A CN201480033395.3A CN201480033395A CN105377232A CN 105377232 A CN105377232 A CN 105377232A CN 201480033395 A CN201480033395 A CN 201480033395A CN 105377232 A CN105377232 A CN 105377232A
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- extract
- macrocystis pyrifera
- algae
- brown
- water
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Classifications
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Abstract
该发明涉及利用超声辅助连续水性萃取从巨藻中获得抗氧化剂萃取物的方法。该过程可以利用新鲜藻类或干燥藻类在将其重悬浮于水中后进行。藻类在水中的悬浮液以在10和30％之间的固体浓度进行制备。混合物进料到超声破碎系统。萃取物经过过滤和冷冻干燥，得到总多酚浓度为每克冻干物62.4mg当量间苯三酚(对于双叉藻)和每克冻干物44mg当量间苯三酚(对于泡叶藻)。萃取物能够被用作化妆品和食品配方中的成分。
Description
技术领域
本发明涉及从巨藻中萃取化合物。更具体来说，本发明涉及从褐色巨藻(brownmacroalgae)中萃取抗氧化剂。
背景技术
抗氧化剂是存在于巨藻、植物以及特别是水果中的次级代谢产物。它们是抑制或阻止基质(底物，substrate)氧化的化合物。在食品、药品和化妆品行业中，主要使用合成的抗氧化剂化合物，如丁基羟基甲苯(BHT)、没食子酸丙酯或丁基羟基茴香醚(BHA)。天然抗氧化剂，像源自葡萄萃取物、迷迭香萃取物、可可萃取物等的那些，因为它们的低毒性和高抗氧化活性而正在被更好地接受。抗氧化剂化合物的大家族是存在于巨藻中的褐藻多酚(phlorotannins)，其显示良好的抗氧化活性。
用于褐藻多酚萃取的若干方案已经被提出，其中，可以提及的是连续液-液分配，其除了在色谱柱中的纯化外，还主要使用有机溶剂，如甲醇、己烷、二氯甲烷、三氯甲烷、乙酸乙酯和丁醇，如2008年，由Yanping,Z.、Zhong-JiQ.、YongL.、Moon-MooK.、Sang-Hoon,L.和Se-KwonK发表在农业食品化学杂志第56卷7001-7009页的在自由基介导的氧化系统中从铁钉菜分离的褐藻多酚的抗氧化效果(AntioxidantEffectsofPhlorotanninsIsolatedfromIshigeokamuraeinFreeRadicalMediatedOxidativeSystems,Yanping,Z.,Zhong-JiQ.,YongL.,Moon-MooK.,Sang-Hoon,L.&Se-KwonK,J.Agric.FoodChem.,56,7001-7009,2008.)；2010年，由Audibert,L.、Fauchon,M.、Blanc,N.、Hauchard,D.和ArGalla,E发表于植物化学分析杂志第21卷399-405页的在褐色海藻泡叶藻中的酚类化合物：分布及自由基清除活性(PhenolicCompoundsintheBrownSeaweedAscophyllumnodosum:DistributionandRadical-scavengingActivities,Audibert,L.,Fauchon,M.,Blanc,N.,Hauchard,D.&ArGalla,E,Phytochemicalanalysis,21,399-405,2010.)；2009年，由Li,Y.、Qian,Z.J.、Ryu,B.、Lee,S.H.、Kim,M.M.和Kim,S.K.发表在生物有机和药物化学杂志第17卷1963-1973页的化学成分和它的体外抗氧化特性：一种可食用的海洋褐藻腔昆布(Chemicalcomponentsanditsantioxidantpropertiesinvitro:anediblemarinebrownalgaEckloniacava,Li,Y.,Qian,Z.J.,Ryu,B.,Lee,S.H.,Kim,M.M.andKim,S.K.,BioorgMedChem17,1963-1973,2009.)；2011年，由Breton,F.、Cérantola,S.和ArGallE.发表于实验海洋生物及生态学杂志第399卷167-172页的泡叶藻(褐藻)中酚类的分布及自由基清除活性(DistributionandradicalscavengingactivityofphenolsinAscophyllumnodosum(Phaeophyceae),Breton,F.,Cérantola,S.&ArGallE.,JournalofExperimentalMarineBiologyandEcology,399,167–172,2011.)。然而，这些工艺会产生在食品和化妆品中不允许的残留物，如甲醇或有机卤素化合物。此外，如果需要比水低的极性，醇水混合物是与石油溶剂相对的选择。
70％丙酮和乙酸乙酯用作溶剂被报道在2006年，由Nakai,M.、Kageyama,N.、Nakahara,K.和Miki,W.发表于海洋生物技术杂志第8卷409-414页的来自任氏马尾藻萃取物的褐藻多酚作为自由基清除剂的褐藻多酚(PhlorotanninsasRadicalScavengersfromtheExtractofSargassumringgoldianum,Nakai,M.,Kageyama,N.,Nakahara,K.&Miki,W.,MarineBiotechnology,8,409-414,2006)中。首先利用己烷的脂类物质清除相，随后利用70％丙酮-水萃取褐藻多酚被使用在高效液相色谱分析来自褐藻墨角藻的褐藻多酚中，Koivikko,R.、Loponen,J.、Pihlaja,K.和Jormalainen,V.，植物化学分析杂志第18卷326-332页，2007(High-performanceliquidchromatographicanalysisofphlorotanninsfromthebrownalgaFucusvesiculosus,Koivikko,R.,Loponen,J.,Pihlaja,K.andJormalainen,V.,Phytochem.Anal.18,pp.326-332,2007)。纯乙醇和60％乙醇已经被用于褐藻多酚在物种如泡叶藻和墨角藻中的萃取，紧接着应用石油醚或二氯甲烷进行液-液分配(2007年，由Parys,R.、Rosenbaum,A.、Kehraus,S.、Reher,G.、Glombitza,K-W和G.M.发表于天然产物杂志1865-1870页的藻类萃取物中多酚类测定的定量方法的评价(Evaluationofquantitativemethodsforthedeterminationofpolyphenolsinalgalextracts,Parys,R.,Rosenbaum,A.,Kehraus,S.,Reher,G.,Glombitza,K-WandG.M.J.Nat.Prod.,1865-1870,2007.)。
发明内容
从处理褐色巨藻如双叉藻(Bifurcariabifurcata)和泡叶藻获得的萃取物，因为它们的岩藻多糖和褐藻多酚含量，而能够被用于食品、化妆品和/或药品用途。高岩藻多糖含量导致这些萃取物对皮肤具有湿润能力，而抗氧化能力是因为褐藻多酚的存在。
为了不干扰其它期望的用途，需要获得不具备很强特征芳香的天然产物用作化妆品成分，这青睐于水萃取而非应用有机溶剂。萃取物的萃取工艺的另一个期望的特征是使用起来经济、可再生、具有很小或没有毒性且其操作没有危险的溶剂。粗萃取物或者分离部分通常显示比合成抗氧化剂如BHA(丁基羟基茴香醚)或BHT(丁基羟基甲苯)大的抗氧化活性。
该发明的目标方法允许用水获得稳定的产物，其易于操作和添加至不同的产物并且不含微量溶剂。
从褐色巨藻萃取抗氧化剂的方法包括：
a)如果使用新鲜的巨藻，经受活水洗涤，除去沙子和附生植物，并且随后用吸水纸干燥。如果使用干藻，这个用水清洁的过程不是必要的。
b)干燥或新鲜的藻随后以3和5g/g之间的液体/固体(L/S)比与水进行混合。
c)前一步的混合物随后经受研磨过程，优选地在刀片研磨机(bladegrinder)，直到将干巨藻粒径降低至0.5和2mm之间和将新鲜巨藻粒径降低至0.5和3mm之间。
d)当以新鲜巨藻为起始时，将研磨的巨藻与液体溶剂以5和15(g/g)之间的液体/固体(L/S)比混合；当以干燥巨藻为起始时，将研磨的巨藻与液体溶剂以50和150(g/g)之间的液体/固体(L/S)比混合；所述液体溶剂包括纯乙醇或1:1(v/v)比的乙醇：水混合物。
e)通过持续应用超声使混合物经受细胞破碎过程。
f)在前一步得到的固体藻残渣通过沉降并随后离心或过滤进行分离。
g)只有当水被使用时，乙醇或50％的水在不超过40℃的温度真空下除去。
h)浓缩的萃取物被冷冻干燥以得到固体萃取物。
产物被冷却至低于5℃储存并且防止光照以避免其被改变。
在另一方面，本发明涉及从处理褐色巨藻得到的稳定抗氧化剂萃取物，所述褐色巨藻更具体而言是双叉藻(Bifurcariabifurcata)、泡叶藻(Ascophyllumnodosum)、欧非囊根藻(Saccorhizapolyschides)和钝马尾藻(Sargassummuticum)种的巨藻藻类。
附图说明
以附图详细显示的实施方式通过非限制实施例的方式被说明：
图1显示了在连续巨藻进料系统中，超声辅助细胞破碎的图。
图2显示了通过C18反相柱HPLC对褐藻多酚的检测。
图3显示了双叉藻萃取物的紫外吸收图谱，其中特征褐藻多酚图谱类似于间苯三酚。
具体实施方式
在具体的实施方式中，本发明涉及从褐色巨藻中得到的水性抗氧化萃取物，其特征在于a)糖类含量为每克冻干物33和156mg之间的葡萄糖；b)岩藻多糖含量为每克冻干物44和118mg之间的硫酸盐，所述岩藻多糖以消化样品后的总硫酸盐表示；c)褐藻多酚含量为每克冻干物12和62.4mg当量之间的间苯三酚，所述褐藻多酚以间苯三酚表示；和d)海藻酸含量为每克冻干物10和55mg当量之间的葡萄糖醛酸。
在另一方面，本发明涉及化妆品和/或食品组合物，其包括本发明的目标抗氧化萃取物。
从双叉藻萃取抗氧化剂的方法的应用实例以举例的方式被提及并且没有限定其保护范围。萃取连续进行并且温度条件低于40℃以防止抗氧化能力或萃取的化合物量下降。
图1显示了在连续巨藻进料系统中，超声辅助细胞破碎的图，所述连续巨藻进料系统由包括被安置于流通池(104)中的超声波发生器(sonotrode)(105)的超声波产生单元组成，其通过主蠕动泵(102)和另一循环泵(103)进行进料。
在本发明的具体实施方式中，水性抗氧化剂化合物的萃取过程包括以下步骤：
a)120g新鲜巨藻用可饮用水清洗，并且随后用蒸馏水清洗。
b)加入300ml水。
c)通过操作叶片式混合器对巨藻进行预研磨10min，得到小于3mm的粒径。
d)向上一步得到的制备物中加水直到得到L/S比为10，并且将其引入供应槽(100)中，其通过搅拌器(101)进行混合。选择在表1中描述的其中一个萃取条件，表1总结了具有4个中心点的22析因实验设计。
e)连续超声萃取条件考虑功率参数(作为应用的标称功率的振幅或百分比)和藻液流入流通池(超声处理或超声池)(104)的流入率的循环之间的比，其中超声波发生器(105)以3和13W/cm3之间的范围的功率密度连续将超声波施加至混合物。表1总结了对实验设计进行的处理组合。萃取装置需要超声辅助萃取系统，诸如图1所示的超声辅助萃取系统。
f)可沉降的固体残渣被留下以沉降并且通过滗析与上清液分离。
g)下一步由再次离心和分离上清液组成。上清液体积为1200ml，其通过30℃或室温下真空蒸发减少至500ml。
h)得到冻干的萃取物(106)，其在该具体实施方式中，包括1400ml的总体积在其中，并且最后得到固体的和干燥的萃取物。
表1.-4个中心点，22实验设计。振幅调节代码-1、0和1对应于振幅为50％、70％和90％。循环比代码-1、0和+1对应于1、1.5和2，循环流速为300ml/min恒定值。
从新鲜巨藻的萃取产率以湿基计在2.9-6.6％(w/w)范围内，而干燥藻的萃取产率在27.7和57.3％(w/w)之间的范围内；表2包含了分析的各个藻种的产率。
相对于水空白，被冻干并随后再溶解在水中的该萃取物的最大吸光度在250nm和280nm之间，如图3所示。
总多酚含量：
术语多酚被理解为意指存在于植物中的这样的化合物的整个家族，所述化合物包含酚基或衍生自酚基：苯甲酸衍生物、肉桂酸衍生物、类黄酮等。
1965年，由Singleton&Rossi,Singleton,V.L.；Rossi,J.J.发表于美国葡萄栽培与酿酒学报第16卷144-158页的利用磷钼酸磷钨酸试剂的总酚比色法(Colorimetryoftotalphenolicswithphosphomolybdicphosphotungsticacidreagents.Singleton&Rossi,Singleton,V.L.；Rossi,J.J.Am.J.Enol.Vitic.,16,144–158,1965.)中提出的方法经略微改进被用于测定得到的萃取物的多酚含量。因此，使用500μl溶于水中的样品，向其加入2.5ml的福林-乔卡梯奥试剂和2.0ml的Na2CO3。在45℃下温育样品15min后，在765nm下读取吸光度。
| 种 | 产率(％，w/w)d.b. | 产率(％，w/w)w.b. |
| 泡叶藻 | 38.0 | 6.6 |
| 双叉藻 | 27.7 | 4.8 |
| 欧非囊根藻 | 42.0 | 4.9 |
| 钝马尾藻 | 57.3 | 2.9 |
表2-以干基计和以湿基计水性萃取物的产率。d.b.：考虑24h×45℃干燥。
1995年由Brand-WilliamsW、CuvelierME和BersetC.发表在LWT食品科学技术杂志第28卷5–3018的自由基方法评价抗氧化活性的应用(Useofafreeradicalmethodtoevaluateantioxidantactivity”,Brand-WilliamsW,CuvelierME,BersetC.LWTFoodSciTechnol28:5–30181995)中提出的DPPH自由基抑制试验用来测定萃取物的供质子能力。该方法经略微改进被应用如下，其中20μl的萃取物水溶液被加入到980μl的自由基的甲醇溶液(6.9×10-5mol/l)中。16min后在515nm下记录吸光度的下降。针对空白的记录计算DPPH自由基抑制百分比。在5和40mg/ml之间的泡叶藻和双叉藻萃取物的浓度范围被评估以测定EC50，其结果分别为23.73±3.83mg萃取物/ml和17.68±2.2mg萃取物/ml。这些以没食子酸当量(GAE)表示的相同值分别对应于1.08±0.16和1.04±0.13mgGAE/ml。
表3-来自四种褐藻品种的冷冻干燥萃取物的特征。
多糖含量：
术语多糖被理解为意指由糖(主要是己糖和/或戊糖)形成的聚合物，其在植物中的功能为结构组成和能量储备。
多糖含量是通过1956年由Dubois,M.、Gilles,K.A.、Hamilton,J.K.、Rebers,P.A.和Smith,F.发表于分析化学杂志第28卷第350-356页的用于糖和相关物质测定的比色法(Colorimetricmethodfordeterminationofsugarsandrelatedsubstances,Dubois,M.；Gilles,K.A.；Hamilton,J.K.；Rebers,P.A.；Smith,F.Anal.Chem.,28,350–356,1956)中提出的苯酚-硫酸法进行测定。从巨藻双叉藻中得到的萃取物每克冻干物156.7mg葡萄糖的平均糖含量被获得，其比在相同条件下从泡叶藻中得到的高29％。
岩藻多糖被理解为意指藻类的多糖特征的家族，其通过岩藻糖衍生物硫酸化糖的聚合而形成。
平均岩藻多糖含量通过1961年由Dodgson,Dodgson,K.S.发表于生化杂志第78卷第312-317页的糖类和其他硫酸酯的酶或非酶水解研究中无机硫酸盐的测定(Determinationofinorganicsulphateinstudiesontheenzymicandnon-enzymichydrolysisofcarbohydrateandothersulphateesters,Dodgson,Dodgson,K.S.,Biochem.J.,78,pp.312-317,1961)中描述的方法测定，并且被表示为消化样品后的总硫酸盐。双叉藻萃取物中的平均值为每克冻干物118mg硫酸盐，比在相同条件下得到的泡叶藻萃取物高134％。通过ICP-OES技术测定的硫水平(平均每克冻干物36.3mgS)是针对泡叶藻获得的那些(平均18.14mg/g)的两倍。
在藻类中主要的多糖是所谓的藻酸盐，其主要通过葡萄糖醛酸聚合形成。
藻酸盐含量是根据1973年由Blumenkrantz等人(Blumenkrantz,N.和Asboe-Hansen,G.)发表于分析生物化学杂志第54卷第484-489页的定量测定糖醛酸的新方法(Newmethodforquantitativedeterminationofuronicacids,Blumenkrantzetal.,Blumenkrantz,N.andAsboe-Hansen,G.Anal.Biochem,54,pp.484-489,1973)中提出的方法从糖醛酸含量估算的。双叉藻萃取物显示以糖醛酸表示并且用葡萄糖醛酸作为标准的平均藻酸盐含量为每克冻干物55.1mg，其比在相同条件下从泡叶藻得到的高15％。
分光光度法测定总多酚
用间苯三酚作为标准品使用福林-乔卡梯奥法测定总多酚。在双叉藻萃取物中平均总多酚含量(其多酚主要是褐藻多酚)为每克冻干物62.4mg当量的间苯三酚，其比从泡叶藻中获得的高7.3％。
色谱法检测褐藻多酚
术语褐藻多酚被理解为意指通过间苯三酚(1,3,5-三羟基苯)的聚合产生的聚合物，与由儿茶酚/表儿茶酸及衍生物聚合而形成的名称鞣酸类似。鞣酸是植物的细胞壁成分并且褐藻多酚是巨藻的细胞壁成分。
褐藻多酚是根据2007年由Koivikko等(Koivikko,R.、Loponen,J.、Pihlaja,K.和Jormalainen,V.)发表于植物化学分析杂志第18卷第326-332页的来自褐藻墨角藻的褐藻多酚的高效液相色谱分析(High-performanceliquidchromatographicanalysisofphlorotanninsfromthebrownalgaFucusvesiculosusPhytochem,Koivikkoetal.,2007,Koivikko,R.,Loponen,J.,Pihlaja,K.andJormalainen,V.,Anal.18,pp.326-332,2007.)中提出的方法学从冻干的萃取物中萃取的，其中用己烷洗涤的步骤被去除。
称量95mg双叉藻萃取物并且溶解在25ml水中；随后用10ml的丙酮/水：7/3混合物萃取褐藻多酚4次。离心样品以分离上清液。合并上清液部分并用N2流除去丙酮。残渣再悬浮于水中并随后冷冻干燥。冻干物溶解于1ml蒸馏水中并准备注入高效液相色谱设备。色谱分离方法是2008年由Zaragoza,M.C.、López,D.、Sáiz,M.P.、Poquet,M.、Pérez,J.、Puig-Parellada,P.、Mármol,F.、Simonetti,P.、Gardana,C.、Lerat,Y.、Burtin,P.、Inisan,C.、Rousseau,I.、Besnard,M.和Mitjavila,M.T.发表于农业食品化学杂志第56卷第7773-7780页的两种墨角藻萃取物在体外和体内的毒性和抗氧化活性(ToxicityandantioxidantactivityinvitroandinvivooftwoFucusvesiculosusextracts,Zaragoza,M.C.,López,D.,Sáiz,M.P.,Poquet,M.,Pérez,J.,Puig-Parellada,P.,Mármol,F.,Simonetti,P.,Gardana,C.,Lerat,Y.,Burtin,P.,Inisan,C.,Rousseau,I.,Besnard,M.,andMitjavila,M.T.J.Agric.FoodChem,56,pp.7773-7780,2008.)中提出的色谱分离方法。
图2显示了主峰(5-6、11和18)，其信号分别在25-26、30和37min被检测到。褐藻多酚混合物的最大吸光度在273nm处被观察到，如图3所示。紫外-可见光谱图谱与间苯三酚分子标准品的图谱吻合。
权利要求书(按照条约第19条的修改)
1.从褐色巨藻中得到的水性抗氧化剂萃取物及其冻干衍生物，其特征在于：
a)糖含量在每克冻干后的萃取物33和156mg葡萄糖之间；
b)岩藻多糖含量在每克冻干后的冻干物44和118mg硫酸盐之间，所述岩藻多糖被表示为消化样品后的总硫酸盐；
c)褐藻多酚含量在每克冻干后的冻干物12和62.4mg当量间苯三酚之间，所述褐藻多酚被表示为间苯三酚；和
d)藻酸盐含量在每克冻干后的冻干物10和55mg当量葡萄糖醛酸之间。
2.根据权利要求1所述的萃取物，其特征在于，紫外区域的最大吸光度在260-280nm之间。
3.根据权利要求1所述的萃取物，其特征在于，DPPH自由基抑制能力的EC50值为每毫升17.7至23.7mg萃取物。
4.根据权利要求1-3所述的萃取物，其中所述褐色巨藻是双叉藻、泡叶藻、欧非囊根藻和钝马尾藻。
5.从新鲜或干燥褐色巨藻中获得根据权利要求1-4表征的抗氧化剂萃取物的方法，包括：
a)如果使用新鲜巨藻，用水洗涤所述巨藻；
b)将所述巨藻与水以3和5g/g之间的液体/固体(L/S)比进行混合；
c)研磨混合物以获得粒径小于3mm的研磨的巨藻；
d)当以新鲜巨藻为起始时，将所述研磨的巨藻与液体溶剂以5和15(g/g)之间的液体/固体(L/S)比混合；当以干燥巨藻为起始时，将所述研磨的巨藻与液体溶剂以50和150(g/g)之间的液体/固体(L/S)比混合；所述液体溶剂包括纯乙醇或1:1(v/v)比的乙醇：水混合物；
e)通过持续应用超声使混合物经受细胞破碎过程，所述超声具有在3和13W/cm3之间范围的功率密度；
f)在前一步得到的固体藻残渣通过沉降并随后离心或过滤进行分离；
g)于小于40℃的温度下在真空下除去乙醇或50％的水，得到浓缩的萃取物；
h)将所述浓缩的萃取物冷冻干燥，得到冻干的萃取物。
6.根据权利要求5所述的方法，其中研磨的粒径对于干燥巨藻在0.5和2mm之间，而对于新鲜巨藻在0.5和3mm之间。
7.根据权利要求1-4表征的抗氧化剂萃取物作为化妆品和食品配方中的成分的用途。
Claims (7)
1.从褐色巨藻中得到的冻干的抗氧化剂萃取物，其特征在于：
a)糖含量在每克冻干物33和156mg葡萄糖之间；
b)岩藻多糖含量在每克冻干物44和118mg硫酸盐之间，所述岩藻多糖被表示为消化样品后的总硫酸盐；
c)褐藻多酚含量在每克冻干物12和62.4mg当量间苯三酚之间，所述褐藻多酚被表示为间苯三酚；和
d)藻酸盐含量在每克冻干物10和55mg当量葡萄糖醛酸之间。
2.根据权利要求1所述的萃取物，其特征在于，紫外区域的最大吸光度在260-280nm之间。
3.根据权利要求1所述的萃取物，其特征在于，DPPH自由基抑制能力的EC50值为每毫升17.7至23.7mg萃取物。
4.根据权利要求1-3所述的萃取物，其中所述褐色巨藻是双叉藻、泡叶藻、欧非囊根藻和钝马尾藻。
5.从新鲜或干燥褐色巨藻中获得根据权利要求1-4表征的冻干的抗氧化剂萃取物的方法，包括：
a)如果使用新鲜巨藻，用水洗涤所述巨藻；
b)将所述巨藻与水以3和5g/g之间的液体/固体(L/S)比进行混合；
c)研磨混合物以获得粒径小于3mm的研磨的巨藻；
d)当以新鲜巨藻为起始时，将所述研磨的巨藻与液体溶剂以5和15(g/g)之间的液体/固体(L/S)比混合；当以干燥巨藻为起始时，将所述研磨的巨藻与液体溶剂以50和150(g/g)之间的液体/固体(L/S)比混合；所述液体溶剂包括纯乙醇或1:1(v/v)比的乙醇：水混合物；
e)通过持续应用超声使混合物经受细胞破碎过程，所述超声具有在3和13W/cm3之间范围的功率密度；
f)在前一步得到的固体藻残渣通过沉降并随后离心或过滤进行分离；
g)于小于40℃的温度下在真空下除去乙醇或50％的水，得到浓缩的萃取物；
h)将所述浓缩的萃取物冷冻干燥，得到冻干的萃取物。
6.根据权利要求5所述的方法，其中研磨的粒径对于干燥巨藻在0.5和2mm之间，而对于新鲜巨藻在0.5和3mm之间。
7.根据权利要求1-4表征的抗氧化剂萃取物作为化妆品和食品配方中的成分的用途。
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| CN106070339A (zh) * | 2016-06-08 | 2016-11-09 | 北京大学深圳研究生院 | 具有抑藻活性的褐藻多酚组合物及其制备方法和应用 |
| CN108066244A (zh) * | 2018-02-02 | 2018-05-25 | 广州赛莱拉干细胞科技股份有限公司 | 一种含褐藻多酚的组合物 |
| CN108186420A (zh) * | 2018-02-27 | 2018-06-22 | 泉州师范学院 | 铁钉菜提取物在制备海藻源护肤品中的应用 |
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| CN108309834A (zh) * | 2018-04-19 | 2018-07-24 | 广州赛莱拉干细胞科技股份有限公司 | 基于褐藻提取物的护肤组合物 |
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| CN113473999A (zh) * | 2018-12-05 | 2021-10-01 | 拜奥特罗尔有限公司 | 抗病毒组合物 |
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|---|---|
| KR20150140382A (ko) | 2015-12-15 |
| ES2441469A1 (es) | 2014-02-04 |
| JP2016522171A (ja) | 2016-07-28 |
| US20160074317A1 (en) | 2016-03-17 |
| EP2997963A1 (en) | 2016-03-23 |
| EP2997963A4 (en) | 2016-11-23 |
| WO2014167162A1 (es) | 2014-10-16 |
| ES2441469B2 (es) | 2014-07-04 |
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