CN107427029A - 虾青素组合物(i) - Google Patents
虾青素组合物(i) Download PDFInfo
- Publication number
- CN107427029A CN107427029A CN201680016343.4A CN201680016343A CN107427029A CN 107427029 A CN107427029 A CN 107427029A CN 201680016343 A CN201680016343 A CN 201680016343A CN 107427029 A CN107427029 A CN 107427029A
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- Prior art keywords
- astaxanthin
- weight
- acid
- monoesters
- composition
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Abstract
本发明涉及虾青素组合物,其用于食品、食品补充剂或饲料中或者用作药物。如果虾青素组合物中含有的至少90重量%的单酯是精确地与一种脂肪族无支链C10‑C22‑单羧酸的单酯,基于组合物中虾青素和虾青素衍生物的总重量,含有至少50重量%、特别是至少60重量%、更特别是至少70重量%、尤其至少80重量%或者至少90重量%的具有脂肪族无支链C10‑C22‑单羧酸的虾青素单酯的虾青素组合物具有特别好的生物利用度。因此,其特别适合用于食品、食品补充剂或饲料,以及作为药物和作为药物制剂或药物组合物的组分,用于治疗用途。
Description
本发明涉及虾青素组合物,其用于食品、食品补充剂或饲料中或者用作药物。
虾青素(3,3'-二羟基-β,β-胡萝卜素-4,4'-二酮)是来自黄叶素类的红色类胡萝卜素着色剂,其如下式所述(所示的是全反式异构体)。
虾青素(下文也作AXT)在3和3'位具有不对称中心,并因此可以作为(3R,3'R)、(3S,3'S)和(3S,3'R)异构体的非对映异构体混合物,作为(3R,3'R)和(3S,3'S)异构体的外消旋物或者以纯异构体的形式存在。合成的AXT完全是非对映异构体(3S,3'S)、(3R,3'S)和(3R,3'R)的混合物。根据各自的天然来源,已从天然来源获得的AXT可以以实质上纯的(3S,3'S)或(3R,3'R)形式存在。类似地,对映体纯的虾青素是可通过全合成得到的。
虾青素主要通过合成制备-就此参见G.Britton,S.Liaanen-Jensen,H.Pfander(编缉),Carotenoids,第2卷,Verlag,Basel,1996,特别是第11页、第267页和281页,以及该文中所引的文献;B.Naturstoffe der chemischen Industrie[Natural substances of the chemical industry],Akademischer Verlag,Heidelberg,2007,第427页和该文中所引的文献;EP 1197483,EP 1285912。
除了合成的虾青素制品,虾青素还可以以工业规模从雨生红球藻(Haematococcuspluvialis)获得(E.A.Johnson,G.H.An,Crit.Rev.Biotechnol.1991,11:297-326)。这提供虾青素单-和二-脂肪酸酯的复杂混合物-就此还参见D.Breithaupt,J.Agric.Food.Chem.2004,52:3870-3875。
虾青素被批准作为饲料添加剂,并主要用作各种动物特别是鲑鱼和鳟鱼的饲料组分。因此,AXT具有维生素样作用,因此在养鱼场对鱼的生殖和免疫应答具有积极作用,并产生吸引人的肉色。虾青素还作为用于食品补充剂的添加剂、作为具有抗氧化性质的化妆品添加剂或者作为食品的着色剂。AXT能保护皮肤免受UV照射引起的应激,在所述功能中,其具有比维生素E显著更强的活性。AXT补充防晒剂的保护作用,并不能被洗掉。
最近,已报道:AXT原则上适合于一系列各种健康病症的治疗-参见例如J.H.Weisburger,Am.J.Clin.Nutr.1991,53:226S–237S;M.Guerin,Trends inBiotechnology,2003,21:210–216;Ghazi Hussein等人,J.Nat.Prod.,2006,69:443–449,虾青素和人类健康–文献调查(Astaxanthin and Human Health–Literature Survey(Algatechnologies)):http://www.astapure-algatech.com/Data/Sub2_1/Files/algatechnologies.pdf,在各情况下具有进一步的检测。
因此,在动物模型上的体内研究得到下述假设,即AXT降低血糖水平,并改善代谢综合征的各种参数(K.Uchiyama,Redox.Rep.2000,7(5):290-3;G.Hussein等人,J.Pharm.Sci.2007,100(Suppl.1):176p;M.Ikeuchi等人,Biosci.Biotechnol.Biochem.2007,71:893–9;Naito,Y.,K.Uchiyama等人,Biofactors2004,20(1):49-59)。
在高血压模型中,AXT致使血流和血管紧张度增加-参见例如H.Yanai等人,(2008)Integrated Blood Pressure Control 1:1–3。
流行病学研究表明:类胡萝卜素类例如虾青素对心脏病具有保护作用-D.A.Cooper等人,Nutr.Rev.1999,57:210-214,J.Krappi等人,Int.J.Nutr.Res.2006,77(1):3-11。由于其抗氧化作用,特别是其抑制低密度脂蛋白氧化的作用,已将类胡萝卜素类例如虾青素推荐用于预防动脉硬化–参见T.Iwamoto等人,J.Atheroscler.Thromb.2000,7:216-222。
此外,各种资料已报道AXT的施用降低癌症风险-参见J.H.Weisburger,Am.J.Clin.Nutr.1991,53:226S–237S。小鼠的体内研究显示虾青素延缓或者事实上抑制肿瘤生长,特别是乳腺癌、膀胱癌和肺癌的生长–参见B.P.Chew等人,Anticancer Res.1999,19:1849-1853,T.Tanaka等人,Carcinogenesis 1994,15:15-19和D.A.Cooper等人,Nutr.Rev.1999,57:133-145。并且,AXT显示促进连接蛋白43的形成,并由此对其他癌症疾病具有化学保护作用(参见A.L.Vine等人,Nutr.Cancer 52(1)(2005),105-113)。
并且,虾青素在调节免疫系统方面发挥作用-参见H.Jyonouchi等人,J.Nutr.1995,125:1570-1573-,并具有抗炎作用;J.Park等人,Nutr.Metab.2010,7:18-27,Kurashige等人,Physiol.Chem.Phys.Med.1990,NMR22:27-38,K.Ohgami等人,Investigative Ophthalmology&Visual Sci.2003,44(6):2694-2701和Y.Suzuki等人,Exp.Eye Res.2006,82(2):275-281。还已推荐将虾青素用于自身免疫疾病例如克罗恩病的治疗。
此外,还推荐将虾青素用于关节疾病的治疗,特别是用于改善炎性关节疾病的症状-参见Y.Nir,G.Spiller,C.Multz C.,含虾青素产品对腕管综合征的作用(Effect of anAstaxanthin-containing product on carpal tunnel syndrome).American College ofNutrition Annual Meeting,San Antonio,德克萨斯,2002年10月,Y.Nir,G.Spiller.LosAltos,California:Health Research and Studies Center 2002.Y.Nir,G.Spiller.J AmColl Nutr,2002,21。
在动物模型中,已显示:AXT的施用对细菌感染过程特别是幽门螺杆菌(Helicobacter pylori)感染引起的肠道炎症具有有利影响–参见M.Bennedsen等人,Immunol.Lett.1999,70:185-189。
此外,已推荐将虾青素用于预防眼睛疾病例如UV照射引起的晶状体和视网膜损害、黄斑变性、白内障和青光眼,用于改善雄性生殖,并用于改善记忆、注意力和身体健康–K.Sawaki等人,Journal of Clinical Therapeutics&Medicines,2002,18:73–88。
虾青素本质上有助于延缓皮肤衰老和减轻皱纹、老年斑和雀斑的形成-SuganumaK等人,Jichi Medical University Journal.2012,35:25-33;K.Tominaga K等人,ActaBiochim Pol.2012;59(1):43-7;E.Yamashita,Carotenoid Science.2006;10:91-5;A.Satoh等人.Oyo Yakuri Pharmacometrics,2011,80(1/2):7-11。
因此,虾青素的主要关注点是用于制备药物,以及用作饲料、食品和食品补充剂,特别是用于人体营养的那些。然而,主要问题是当口服施用时,虾青素被人或动物体不充分地吸收,并且血清或淋巴血清中达到的血清水平是非常低的–参见例如R.M.Clark等人.Lipids 2000,35:803-806;J.Mercke Odeberg等人,Europ.J.Pharm.Sci.2003,19:299-304,M.Osterlie等人,J.Nutr.Biochem,2000,11:482-490。另一个问题是虾青素略溶于适合于制备施用的食品补充剂和药物的辅助剂中。尽管该问题可通过用脂肪酸酯化虾青素而部分克服,但是具有脂肪酸的虾青素的二酯就达到的血清水平而言令人吃惊地具有与非酯化虾青素相当的性质–参见D.A.White等人,Aquacult.Res.2002,33:343-350,Odeberg等人,Eur.J.Pharmac.Sciences 2003,19:299-304,Miyazawa等人,Biosci BiotechnolBiochem,2011,76:1856-1858,Osterlie等人,J.Nutr.Biochem.,11,2000:482-490,Okada等人,Biosci.Biotechnol.Biochem.,2009,73:1928-32,Coral-Hinostroza等人,Comparative Biochemistry and Physiology,Part C,139,2004:99-110。
已知的是虾青素通过被动扩散被吸收到肠道上皮细胞-因此需要一定量的脂肪,并因此其可被食品中的脂肪促进(参见G.N.Coral-Hinostroza等人,Comp.Biochem.Physiol.Part C 2004,139:99-110,具有进一步检测)。J.Mercke Odeberg等人,Europ.J.Pharm.Sci.2003,19:299-304报道可通过特定的基于脂肪的制剂而提高虾青素的口服生物利用度,用于该目的的乳化剂对生物利用度具有大的影响。然而,经制剂的口服生物利用度的提供是有限的,这限制虾青素的可能应用。
本申请人所做的研究已显示从雨生红球藻(Haematococcus pluvialis)获得的“天然虾青素”(虾青素脂肪酸酯的复杂混合物)具有高于虾青素或虾青素二-脂肪酸酯的口服生物利用度。然而,天然虾青素的商品来源是非常有限的。由于所述混合物的复杂性,很少有兴趣将其用于药物用途。
因此,本发明的目的是克服现有技术的缺点,以及特别是制备虾青素衍生物或虾青素组合物,其首先具有更好的口服生物利用度,并且此外,其比自雨生红球藻(Haematococcus pluvialis)获得的“天然虾青素”更容易得到。
较早的欧洲专利申请14184483.7描述虾青素二脂肪酸酯的制备,其通过在叔胺碱存在下,用脂肪酰氯酯化虾青素。如果使用游离酸代替酰氯,主要产物是单-脂肪酸酯,其可通过除去未反应的虾青素从反应混合物中获得。并且,可能的是利用亚化学计量的酰氯以及未反应的虾青素和二脂肪酸酯得到单脂肪酸酯。可通过例如色谱法,从混合物中分离单酯。
令人吃惊地,现在已发现:当至少90重量%的虾青素组合物中存在的单酯是精确地与一种脂肪族无支链C10-C22-单羧酸的单酯时,基于组合物中虾青素和虾青素衍生物的总重量,含有至少50重量%、特别是至少60重量%、尤其至少70重量%,尤其至少80重量%或者至少90重量%的虾青素与脂肪族无支链C10-C22-单羧酸的单酯的虾青素组合物显示特别好的生物利用度。
因此,本发明的主题是虾青素组合物在食品、食品补充剂或饲料中的用途,其中基于组合物中虾青素和虾青素衍生物的总重量,虾青素组合物含有至少50重量%、特别是至少60重量%、尤其优选至少70重量%,并尤其至少80重量%或者至少90重量%的虾青素与脂肪族无支链C10-C22-单羧酸的单酯,其中至少90重量%的虾青素组合物中存在的单酯是精确地与一种脂肪族无支链C10-C22-单羧酸的单酯。
本发明的主题还是此处和下文中所述的虾青素组合物,其作为药物、以及作为药物制剂或药品的组分用于治疗用途。因此,本发明还涉及药物,其含有根据本发明的虾青素组合物,以及至少一种适合于制药目的的佐剂或辅助剂。
本发明还涉及食品添加剂,其含有根据本发明的虾青素组合物,以及至少一种适合于食品的添加剂,即至少一种适合于食品的辅助剂。
本发明还涉及饲料添加剂,其含有根据本发明的虾青素组合物,以及至少一种适合于饲料的添加剂,即至少一种适合于饲料的辅助剂。
本发明还涉及食品补充剂,其含有根据本发明的虾青素组合物,以及至少一种适合于食品补充剂的添加剂,即至少一种适合于食品补充剂的辅助剂。
自然地,上述食品补充剂、饲料添加剂、食品补充剂和药物组合含有根据本发明的虾青素组合物作为唯一的含虾青素的组分,并且其特别不再含未酯化的虾青素或者其他虾青素衍生物。
本发明具有一系列优点。首先,根据本发明的组合物显示比未酯化的虾青素或相应的二酯更好的口服生物利用度,并且在血浆中达到的虾青素血清水平要高数倍。令人吃惊地,根据本发明的虾青素组合物的口服生物利用度甚至比“天然虾青素”更好。并且,所述组合物可容易地合成。最后但并不是最不重要的,由于其比“天然虾青素”复杂性低且口服生物利用度得到改善,根据本发明的组合物还对药物应用是特别有吸引力的。
特别是,根据本发明的虾青素组合物适合于预防和治疗多种疾病症状和健康障碍,例如
-预防和治疗关节疾病,特别是炎性关键疾病例如类风湿性关节炎、关节病和腕管综合征,
-预防和治疗眼病例如对晶状体或视网膜的损害,诸如预防黄斑变性、白内障或青光眼,并用于保护晶状体和视网膜免于UV照射引起的损害,
-预防和治疗皮肤病,以及用于预防和减轻皮肤衰老,特别是预防和减轻皱纹、老年斑和雀斑,
-预防和治疗心脏病,特别是预防心肌梗塞,以及用于改善心肌梗塞后的再愈合,
-预防和治疗2型糖尿病和相关伴发病,例如预防和治疗代谢综合征,用于降低胰岛素抵抗个体的血糖水平或者用于治疗和预防糖尿病肾病,
-预防和治疗肿瘤疾病,特别是宫颈癌、膀胱癌、乳腺癌和肺癌,
-预防和治疗血管病例如动脉硬化,
-治疗细菌感染,特别是改善幽门螺杆菌感染引起的胃肠道疾病病程,
-预防和治疗炎性疾病,特别是自身免疫疾病例如克罗恩病,
-预防和治疗神经变性疾病例如帕金森病,
-用于改善雄性生殖,
-用于改善一般健康情况,
-用于改善记忆和注意力,
-用于改善身体健康,
-用于增强免疫系统。
本发明含义范围内的治疗不仅包含急性或慢性体征、症状和/或机能失常的治疗,而且包含预防治疗(预防),特别是作为复发预防或时期(phase)预防。治疗可以针对症状例如抑制症状。治疗可短期进行,治疗可以是中期的或者治疗还可以是长期治疗例如作为维持治疗的一部分。
上下文中,饲料理解为是用于非人类特别是非人类哺乳动物但还有鱼的营养的产品。因此,饲料添加剂理解为意指制剂,例如粉末或液体形式的,可在生产过程中,将其掺入饲料中。
上下文中,食品理解为意指含有营养物的产品,用于人类营养,其主要用于营养物例如脂肪、蛋白质和碳水化合物的摄入。因此,食品添加剂理解为意指制剂,例如粉末或液体形式的,可在生产过程中,将其掺入食品中。
上下文中,食品补充剂理解为意指适合于口服施用的制剂,并且除传统食品外,其被人摄食,在虾青素或衍生物存在下,主要目的是施用活性物质,以便用所述方式实现普通饮食或一般健康情况的改善。食品补充剂位于食品和药品之间的临界处,并且在EU法律中,由指南2002/46/EC管理。
上下文中在通用术语例如单羧酸或脂肪酸中所用的前缀Cn-Cm指碳原子数的范围,其可包括所述通用术语所指的组的成员。
基于组合物中虾青素和虾青素衍生物的总重量,根据本发明的虾青素组合物主要包含即至少50重量%,特别是至少60重量%,尤其优选至少70重量%,尤其至少80重量%或者至少90重量%的虾青素与脂肪族、无支链C10-C22-单羧酸的单酯。此外,根据本发明的虾青素组合物还可包含未酯化的虾青素和/或一种或多种虾青素二酯,根据本发明,基于组合物中虾青素和虾青素衍生物的总重量,其含量不超过50重量%、特别是40重量%、尤其优选30重量%,尤其是20重量%或10重量%。然而,虾青素组合物还可以唯一地或者几乎唯一地(即大于95重量%)由虾青素与各脂肪族、无支链C10-C22-单羧酸的单酯构成。
根据本发明,单酯是均匀的,即其基本上(即至少90重量%)是精确地一种脂肪族、无支链的C10-C22-单羧酸的单酯。在该语境中,术语“精确地一种”是指单酯是特定的、脂肪族、无支链的C10-C22-单羧酸(即具有相同经验式的脂肪族、无支链的C10-C22-单羧酸)的单酯。在不饱和的、脂肪族、无支链的C10-C22-单羧酸的情况下,特定的脂肪族C10-C22-单羧酸不仅包括各种双键异构体的混合物,而且包括顺式和反式异构体的混合物。如果该组合物还包含虾青素二酯,则二酯通常是与也形成单酯的脂肪族、无支链的C10-C22-单羧酸的二酯。
脂肪族、无支链C10-C22-单羧酸可以是饱和的或者不饱和的。不饱和的脂肪族、无支链C10-C22-单羧酸可以包括一个或多个例如1、2、3、4、5或6个烯类双键。关于各双键,后者可以是顺式-或者反式-构型。脂肪族、无支链C10-C22-单羧酸通常是非官能化的,即除羧基的两个氧原子之外,他们不包括其它杂原子。
饱和的、脂肪族、无支链C10-C22-单羧酸的示例主要是偶数的饱和C10-C22-单羧酸,例如癸酸、月桂酸、肉豆蔻酸、棕榈酸、硬脂酸、花生酸和山萮酸;
不饱和的、脂肪族、无支链C10-C22-单羧酸的示例主要是
-单不饱和C10-C22-单羧酸例如肉豆蔻烯酸、棕榈油酸、油酸及其双键异构体岩芹酸(petroselic acid)、反油酸(elaidic acid)和异油酸(vaccenic acid)(C18-1羧酸)、C20-1酸例如二十碳烯酸(eicosenic acid)和鳕油酸(gadoleic acid),C22-1酸例如鲸蜡烯酸(cetoleic acid)和芥酸;
-多不饱和C10-C22-单羧酸例如亚油酸(C18-2酸),C18-3酸α-亚麻酸、γ-亚麻酸、calendulic acid、石榴酸、α-桐酸和β-桐酸,C20-4酸花生四烯酸,C20-5酸二十碳五烯酸(timnodonic acid=eicosapentaenoic acid)和鰶鱼酸(clupanodonic acid),C22-5酸二十二碳五烯酸和C22-6酸二十二碳六烯酸(cervonic acid)。
优选的C10-C22-单羧酸选自饱和的和不饱和的脂肪族无支链C16-C22-单羧酸。
优选的C10-C22-单羧酸选自单-或多不饱和、脂肪族的、无支链的C10-C22-单羧酸,特别是单-或多不饱和、脂肪族的、无支链的C16-C22-单羧酸。至少单不饱和C10-C22-单羧酸特别选自C18-1、C18-2、C18-3和C18-4脂肪酸。尤其是,其是C18-1脂肪酸。
根据本发明的虾青素组合物中,优选的是其中至少90重量%的虾青素单酯是虾青素精确地与一种脂肪族无支链C16-C22-单羧酸的单酯的那些。
根据本发明的虾青素组合物中,优选的还是其中至少90重量%的虾青素单酯是虾青素精确地与一种单-或多不饱和的脂肪族无支链C10-C22-单羧酸的单酯的那些,包括不饱和的脂肪族无支链C10-C22-单羧酸的顺/反混合物的单酯,以及所述不饱和的脂肪族无支链C10-C22-单羧酸的双键异构体混合物的单酯。
根据本发明的虾青素组合物中,其他还优选的是其中至少90重量%的虾青素单酯是虾青素精确地与一种单-或多不饱和的脂肪族无支链C16-C22-单羧酸的单酯的那些,包括不饱和的脂肪族无支链C16-C22-单羧酸的顺/反混合物的单酯,以及所述不饱和的脂肪族无支链C16-C22-单羧酸的双键异构体混合物的单酯。在本文中,已证明如下是特别有益的:不超过60%、特别是不超过40%并尤其是不超过30%的不饱和脂肪酸以反式-脂肪酸存在,即在脂肪酸残基中全部双键的不超过60%、特别是不超过40%并尤其是不超过30%以反式存在。
根据本发明的虾青素组合物中,其他还特别优选的是其中至少90重量%的虾青素单酯是虾青素与无支链脂肪酸的单酯的那些,所述无支链脂肪酸选自C18-1、C18-2、C18-3和C18-4脂肪酸。在本文中,已证明如下是特别有益的:C18-1、C18-2、C18-3和C18-4脂肪酸的不超过60%,特别是不超过40%并尤其是不超过30%以反式-脂肪酸存在,即在脂肪酸残基中全部双键的不超过60%,特别是不超过40%并尤其是不超过30%以反式存在。
根据本发明的虾青素组合物中,其他还特别优选的是其中至少90重量%的虾青素单酯是虾青素与无支链脂肪酸的单酯的那些,所述无支链脂肪酸选自C16-0和C18-0脂肪酸。
根据本发明的虾青素组合物中,其他特别优选的是其中至少90重量%的虾青素单酯是虾青素与C18-1脂肪酸特别是油酸或者油酸的顺/反异构体混合物的单酯的那些。在这些C18-1脂肪酸的单酯中,优选的是C18-1脂肪酸中,不超过60%,特别是不超过40%并尤其是不超过30%的双键以反式存在。
在一组实施方案中,至少40重量%、特别是至少60重量%或者至少80重量%的单酯,特别是不饱和的脂肪族无支链C16-C22-单羧酸单酯,尤其优选C18-1、C18-2、C18-3和C18-4脂肪酸单酯,并尤其是油酸单酯,以全-E虾青素单酯存在。
在另一组实施方案中,20-90重量%、特别是30-80重量%或者40-70重量%的单酯,特别是不饱和的脂肪族无支链C16-C22-单羧酸的单酯,尤其优选C18-1、C18-2、C18-3和C18-4脂肪酸的单酯,并尤其是油酸单酯,以全-E虾青素单酯存在,并且10-80重量%、特别是20-70重量%或者30-60重量%以虾青素的一种或多种Z异构体例如9-Z、13-Z或15-Z异构体存在,或者以所述虾青素Z异构体的两种或三种的混合物存在。
在另一组实施方案中,至少40重量%、特别是至少60重量%或者至少80重量%的饱和脂肪族无支链C16-C22-单羧酸的单酯尤其优选C16-0或C18-0脂肪酸的单酯以全-E虾青素单酯存在。
在另一组实施方案中,20-90重量%、特别是30-80重量%或者40-70重量%的饱和脂肪族无支链C16-C22-单羧酸的单酯尤其优选C16-0或C18-0脂肪酸单酯的以全-E虾青素的单酯存在,并且10-80重量%、特别是20-70重量%或者30-60重量%的该脂肪酸的单酯以虾青素的一种或多种Z异构体例如9-Z、13-Z或15-Z异构体存在或者以所述虾青素Z异构体的两种或三种的混合物存在。
在另一组实施方案中,至少80重量%、特别是至少90重量%的单酯、特别是不饱和的脂肪族无支链C16-C22-单羧酸的单酯、尤其优选C16-0、C18-0、C18-1、C18-2、C18-3和C18-4脂肪酸的单酯并特别是油酸单酯以虾青素3S,3’S对映体的单酯存在。
在另一组实施方案中,至少80重量%、特别是至少90重量%的单酯、特别是不饱和的脂肪族无支链C16-C22-单羧酸的单酯、尤其优选C16-0、C18-0、C18-1、C18-2、C18-3和C18-4脂肪酸的单酯并特别是油酸单酯以虾青素3R,3’R对映体的单酯存在。
在另一组实施方案中,单酯、特别是不饱和的脂肪族无支链C16-C22-单羧酸的单酯、尤其优选C16-0、C18-0、C18-1、C18-2、C18-3和C18-4脂肪酸的单酯并特别是油酸单酯是虾青素3S,3’S对映体、3R,3'S-内消旋体和3R,3’R对映体的混合物的单酯,特别是这些虾青素形式的统计学混合物。
根据本发明的一组实施方案,根据本发明的虾青素组合物或相应的单酯用于食品添加剂或者饲料添加剂中。所述食品或饲料添加剂包含根据本发明的虾青素组合物,以及至少一种适合于食品或饲料的佐剂或辅助剂。根据本发明目的,适合于食品或饲料的辅助剂应理解为意指批准用于动物和/或人营养的物质。
适合的辅助剂特别是通过在添加剂中将虾青素组合物稀释至更好控制的浓度而允许将添加剂引入到食品中的那些。所述包括上述所有载体,特别是液体载体例如植物油和有机溶剂,但是还包括固体载体例如脂肪、脂肪酸、蜡类、脂肪醇和脂肪醇的脂肪酸酯、碳水化合物、糖醇和无机填充剂,其被批准用于食品或饲料生产。
溶剂的示例是:
-C1-C6-烷醇例如乙醇、1-丙醇、2-丙醇、1-丁醇、2-丁醇、2-甲基-1-丙醇、3-甲基-1-丁醇、1-戊醇及其混合物;
-脂肪族C1-C4-羧酸的C1-C4-烷基酯例如甲酸、乙酸、丙酸或丁酸的甲酯、乙酯、正丙酯、异丙酯、正丁酯、2-丁酯或异丁酯例如乙酸甲酯、乙酸乙酯、乙酸正丙酯、乙酸异丙酯、乙酸正丁酯、乙酸异丁酯、甲酸乙酯及其混合物;和
-脂肪族特别是无环的含有3-6个C原子的酮例如丙酮、甲基乙基酮、异丁基甲基酮及其混合物;和
-来自各类上述溶剂的上述溶剂的混合物。
适当的碳水化合物包括单-、二-、寡-和多-糖。单糖和二糖的示例主要是葡萄糖、果糖、半乳糖、甘露糖、麦芽糖、蔗糖和乳糖。适当的多糖是淀粉和低聚淀粉降解产物(糊精)和纤维素粉。
适当的糖醇主要是山梨聚糖和甘油。
适当的脂肪和油可以是合成、矿物质、植物或动物来源的。
油的示例是植物油例如大豆油、葵花籽油、玉米油、亚麻籽油、菜籽油、红花油、小麦胚芽油、米糠油、椰子油、扁桃仁油(almond oil)、杏仁油、棕榈油、棕榈仁油、鳄梨油、荷荷巴油(jojoba oil)、榛子油、胡桃油、花生油、阿月浑子油(pistachio oil)、中链(=C8-C10)植物脂肪酸的甘油三酯(所谓的MCT油)和PUFA油(PUFA=多不饱和脂肪酸例如二十碳五烯酸(EPA)、二十二碳六烯酸(DHA)和α-亚麻酸),还有半合成甘油三酯例如辛酸/癸酸甘油三酯例如miglyol型,还有液体石蜡、液体氢化聚异丁烯、角鲨烷、角鲨烯,还有动物油和脂肪例如鱼油包括鲭油、鲱鱼(sprat)油、金枪鱼油、大比目鱼油、鳕鱼油和鲑鱼油。优选的是在40℃是液体的植物油和动物来源的油,特别是植物油例如大豆油、葵花籽油、红花油、玉米油、橄榄油、亚麻籽油、油菜籽油、米糠油、椰子油、花生油、棕榈油、棕榈仁油、PUFA油、MCT油,还有鱼油,以及所述油的混合物。
与油相比,脂肪通常具有30℃以上的熔点。脂肪的示例是:
-具有12-30个C原子(饱和的C12-C30-脂肪酸)、特别是14-28个C原子(饱和的C14-C28-脂肪酸)并尤其是16-24个C原子(饱和的C16-C24-脂肪酸)的饱和脂肪酸例如肉豆蔻酸、棕榈酸、珠光脂酸(margaric acid)、硬脂酸、花生酸、山萮酸、蜡酸、蜂花酸(melissicacid)和木蜡酸,及其混合物;
-含有14-30个C原子特别是14-28个C原子并尤其是16-24个C原子的饱和脂肪酸的脂肪酸酯,例如棕榈酸、珠光脂酸、硬脂酸、花生酸、山萮酸、蜡酸、蜂花酸和木蜡酸的酯,及其混合物,特别是上述脂肪酸的甘油单-、二-或三酯及其混合物(下文中称作脂肪酸甘油酯),特别是上述饱和脂肪酸并尤其是含有14-28个C原子并尤其是16-28个C原子的那些饱和脂肪酸的酯,以及优选含有14-28个C原子并尤其是16-28个C原子的上述饱和脂肪酸与C10-C30-脂肪醇特别是C14-C28-脂肪醇的酯。上述饱和脂肪酸的酯还可以基于酯中脂肪酸含量,以至多10重量%的量包含酯化形式的单-或多不饱和脂肪酸。特别是,基于酯中总脂肪酸组分,所述酯中不饱和脂肪酸组分的含量占少于5重量%。
油和脂肪可以是精制油或者粗油/脂肪,其还以通常量包含来源特异性杂质例如蛋白质、磷酸盐/酯、碱金属盐、碱土金属盐等。
适当的脂肪醇特别是含有8-30个C原子的饱和脂肪醇(下文还称C8-C30-脂肪醇),例如鲸蜡醇、硬脂醇、十九醇、花生醇、山萮醇、二十四烷醇、蜡醇、蜜蜡醇(myricylalcohol)和蜂花醇(melissyl alcohol)。
适当的蜡特别是植物或动物来源的天然蜡例如蜂蜡、小烛树蜡(candelillawax)、虫胶蜡、牛油树脂和巴西棕榈蜡,碳水化合物蜡例如石蜡、纯地蜡(ceresin)、沙索蜡(Sasol waxes)、地蜡(ozokerite)和微蜡。
适合于食品的惰性无机填充剂的示例是粉末形式的无机材料(无机填充剂),例如氧化物诸如氧化铝、二氧化硅、二氧化钛;硅酸盐诸如硅酸钠、硅酸镁、滑石、硅酸钙、硅酸锌、硅酸铝如硅酸铝钠、硅酸铝钾、硅酸铝钙、皂土、白陶土和氯化钠。
适合于食品和饲料的辅助剂还包括分散剂,其包括用于将虾青素组合物分散于亲脂性载体的亲脂性分散剂,以及用于将根据本发明的虾青素组合物分散于亲水性载体例如水的保护性胶体,所述辅助剂还包括批准用于食品的抗氧化剂(氧化稳定剂)和着色剂。
抗氧化剂的示例是生育酚例如α-生育酚、α-生育酚棕榈酸酯、α-生育酚乙酸酯、叔丁基苯甲醇、叔丁基羟基茴香醚、抗坏血酸、其盐和酯,例如抗坏血酸钠、抗坏血酸钙、磷酸抗坏血酸酯和棕榈酸抗坏血酸酯和乙氧喹。如果需要,基于添加剂的总重量,抗氧化剂通常以0.01-10重量%的量存在于根据本发明的添加剂中。
防腐剂的示例包括苯甲酸及其盐特别是其钠、钾和钙盐,4-羟基苯甲酸(PHB)及其盐,特别是其钠、钾和钙盐,PHB烷基酯的盐例如PHB甲酯的钠盐、PHB乙酯的钠盐和PHB丙酯的钠盐,山梨酸及其盐特别是其钠、钾和钙盐,丙酸盐例如特别是其钠、钾和钙盐,硼酸和乳酸及其盐。如果需要,基于添加剂的总重量,防腐剂通常以0.001-2重量%的量存在于添加剂中。
典型的亲脂性分散剂是棕榈酸抗坏血酸酯,聚甘油脂肪酸酯例如聚甘油-3聚蓖麻油酸酯(PGPR90),山梨聚糖脂肪酸酯特别是山梨聚糖C10-C28-脂肪酸酯例如山梨聚糖的单-或二-C10-C28-脂肪酸酯诸如山梨聚糖单月桂酸酯、山梨聚糖单油酸酯和山梨聚糖单硬脂酸酯(SPAN60)、乙氧基化山梨聚糖脂肪酸酯例如PEG(20)山梨醇单油酸酯,乳酸与饱和C10-C24-脂肪酸的单酯,饱和C16-C28-脂肪酸的糖酯,丙二醇脂肪酸酯和磷脂例如卵磷脂。如果需要,基于添加剂的总重量,亲脂性分散剂通常以0.01-10重量%的量存在于添加剂中。
保护性胶体是适合于将水不溶性固体分散于含水组合物中的聚合的物质,批准用于食品和饲料的适当的保护性胶体包括例如,
1)蛋白质类保护胶体,
2)木质素磺酸、其盐,特别是其钠盐和钾盐,
3)寡糖和多糖,包括改性的多糖例如糊精、纤维素和纤维素衍生物例如甲基纤维素、羧甲基纤维素及其盐、羟乙基纤维素、羟丙基纤维素和羟丙基甲基纤维素,阿拉伯树胶,果胶,
4)聚乙烯醇,包括部分水解的聚乙烯醇,
5)聚乙烯吡咯烷酮和
上述保护性胶体的混合物。
第1)组蛋白类保护性胶体是溶于水或者在水中可溶胀的聚合物质,并且其由氨基酸构成,并任选地包含糖苷化合物。通常,蛋白类保护性胶体是植物或动物来源的。第1)组蛋白类保护性胶体的示例是酪蛋白类和酪蛋白酸盐,包括αS1、αS2、β和κ酪蛋白及其混合物,醇溶谷蛋白(prolamin)即源自谷物种子的储藏蛋白例如麦醇溶蛋白、黑麦醇溶蛋白(secalin)、燕麦球蛋白(avenalin)、大麦醇溶蛋白、玉米醇溶蛋白、oryzin和高粱醇溶蛋白,乳清蛋白质例如β-乳球蛋白、α-乳清蛋白、血清白蛋白、蛋白胨(proteosepeptone)、免疫球蛋白及其混合物,明胶例如牛、猪和鱼明胶,特别是经酸降解得到的明胶例如明胶A100和A200,经碱降解得到的明胶例如明胶B100和B200,以及经酶降解得到的明胶种类例如以商标Collagel A、Sol DA、Sol PA和Sol LDA(DGF Stoess)可得到的那些产品,还有大豆蛋白质和部分水解的大豆蛋白质和羽扇豆蛋白质。羽扇豆蛋白理解为意指从羽扇豆得到的植物蛋白质。根据优选实施方案,粉状组合物包含至少一种选自第1)组的蛋白类保护性胶体,其任选地与来自第3)组的寡糖或多糖组合。蛋白类保护性胶体的分子量(平均重量)通常是10000-250000道尔顿,特别是15000-200000道尔顿,并尤其是20000-180000道尔顿。优选的保护性胶体是酪蛋白、酪蛋白酸盐例如酪蛋白酸钠、大豆蛋白质、部分水解的大豆蛋白质、醇溶谷蛋白和羽扇豆蛋白。
根据本发明优选组的实施方案,食品或饲料添加剂是根据本发明的虾青素组合物在适合于食品或饲料的油或脂肪中的溶液或混悬液。通常,基于添加剂的总重量,在所述添加剂制剂中的虾青素浓度是0.01重量%~30重量%,特别是0.1重量%~10重量%。对于溶液,浓度优选是0.01-3重量%,特别是0.1-2重量%。对于混悬液,虾青素浓度是1-30重量%,特别是2-20重量%。虾青素浓度指单酯、二酯(任选存在的)以及非酯化虾青素形式的虾青素总浓度。除了适用于食品或饲料的油之外,溶液可以包含上述添加剂,例如亲脂性分散剂和/或抗氧化剂和/或着色剂,其优选为上述量。对于根据本发明的虾青素组合物的混悬液,至少80重量%、特别是至少90重量%的虾青素组合物颗粒通常具有100μm以下特别是70μm以下,并尤其是50μm以下的粒径。通常,混悬液中虾青素组合物的颗粒具有0.2-50μm特别是0.3-30μm,并尤其是0.5-20μm的体积-平均粒径(D4,3值)。将体积-平均粒径理解为意指经稀释的0.01-0.1重量%尤其是0.05重量%混悬液的夫琅禾费(Fraunhofer)衍射测定的体积-平均粒径。
用于食品和饲料的根据本发明的添加剂还可以是粉末。通常,除了根据本发明的虾青素组合物,这些粉末还包括其他粉末组分。所述特别包括助流剂和填充剂。
将助流剂(也称作抗凝剂)理解为意指粉状固体物质,其降低粉末颗粒的互相粘附或者粉末颗粒向容器壁的粘附。助流剂通常是适合于食品的惰性、固体、无机、粉状物质,例如氧化物诸如氧化铝、二氧化硅,特别是微粉化的二氧化硅形式的,诸如热解硅石或者硅胶(E 551)或者二氧化钛(E 171),磷酸盐例如磷酸三钙,氢氧化物类例如氢氧化铝,碳酸盐和碳酸氢盐例如碳酸钠(E 500)、碳酸氢钠、碳酸钾(E 501)、碳酸镁(E 504)和碳酸钙(E170),或者硅酸盐例如硅酸钠(E 550)、硅酸镁(E 553a)、滑石(E 553b)、硅酸钙(E 552)、硅酸锌(E 557),硅酸铝如硅酸铝钠(E 554)、硅酸铝钾(E 555)、硅酸铝钙(E 556)、皂土(E558)、白陶土(E 559)、氯化钠,和/或适合于食品的惰性、固体、有机、粉状物质,例如晶状单-、二-或更高的多糖例如乳糖、糖(蔗糖)、纤维素粉末、硬脂酸或者硬脂酸盐例如硬脂酸镁(E 572)、硬脂酸铵(E 571)或者硬脂酸铝(E 573)。优选地,助流剂具有低于粉末颗粒的粒度。优选地,助流剂的颗粒具有虾青素衍生物粉末颗粒的体积-平均粒径的1/100-1/2的体积-平均粒径。基于粉状添加剂的总重量,助流剂的量通常将不超过10重量%,并且如果存在,通常占0.1-10重量%,优选0.2-5重量%,特别是0.3-3重量%。
除虾青素组合物之外,粉状添加剂组合物包含一种或多种其他粉末组分。除了上述助流剂,所述特别包括适合于食品且优选在50℃特别是80℃是固体的其它有机和无机物质。这些特别包括上述填充剂、保护性胶体、抗氧化剂和防腐剂。通常,根据本发明的粉状组合物中的至少90重量%的粉末颗粒具有500μm以下特别是不超过200μm的粒径。通常,粉末颗粒具有0.5-300μm尤其是0.5-200μm的平均粒度(粒径、平均体积、D4,3值)。
一组根据本发明的粉状食品和饲料添加剂的实施方案中,粉状制剂包含至少一种保护性胶体。所述组合物可分散于水中。虾青素组合物中保护性胶体与虾青素组分的重量比通常是50:1~1:5特别是20:1~1:2,并尤其是10:1~1:1。
在粉状食品和饲料添加剂的优选实施方案中,粉状制剂包含至少一种蛋白类保护性胶体。根据第一组,蛋白类保护性胶体特别是大豆蛋白或者大豆蛋白和其他蛋白类保护性胶体的混合物,例如大豆蛋白和醇溶谷蛋白的混合物、大豆蛋白和羽扇豆蛋白的混合物、大豆蛋白和酪蛋白和/或酪蛋白酸盐的混合物、大豆蛋白和大豆蛋白水解物的混合物。特别是,大豆蛋白形成蛋白类保护性胶体的主要成分;保护性胶体中,它的含量占至少50重量%,特别是至少80重量%或者至少90重量%。根据第二组,蛋白类保护性胶体特别是部分水解的大豆蛋白或者部分水解的大豆蛋白和另外的蛋白类保护性胶体的混合物,例如部分水解的大豆蛋白与醇溶谷蛋白的混合物、部分水解的大豆蛋白与羽扇豆蛋白的混合物、部分水解的大豆蛋白与酪蛋白和/或酪蛋白酸盐的混合物。特别是,部分水解的大豆蛋白形成蛋白类保护性胶体的主要组分;在保护性胶体中,它的含量占至少50重量%,特别是至少80重量%或者至少90重量%。部分水解的大豆蛋白理解为意指已用蛋白酶进行部分酶降解的大豆蛋白。所述部分水解的大豆蛋白的水解度DH通常是至少1%,特别是至少5%,例如1-20%或者特别是5-16%。水解度DH理解为意指水解的肽键数与起始蛋白中肽键总数的商。根据C.F.Jacobsen等人在“Methods of Biochemical Analysis”,第IV卷,171-210页,Interscience Publishers Inc.,纽约1957中所述的,水解度可通过称为“pH-stat法”的方法测定。不但用于制备根据本发明的制剂而且用于制备部分水解大豆蛋白的大豆蛋白通常是市售的大豆蛋白分离物和浓缩物,通常具有70-90重量%的蛋白含量,剩余的10-30重量%是未定的或多或少的其他植物成分。
在粉状食品和饲料添加剂的优选实施方案中,粉状制剂包含选自木质素磺酸盐特别是木质素磺酸钠的至少一种保护性胶体,以及任选的其他保护性胶体特别是来自第3)组中的那些。在所述实施方案中,木质素磺酸盐特别形成保护性胶体的主要成分;保护性胶体中其含量占至少50重量%、特别是至少80重量%或者至少90重量%。
本发明还涉及含有根据本发明的虾青素组合物的食品,其中虾青素组合物的浓度相应于批准用于食品的食品中的虾青素含量。通常,按虾青素计算,根据本发明的组合物浓度是1-500mg/kg各食品。
已经含有根据本发明向其中添加的根据本发明的组合物的食品的示例包括脂肪食品例如香肠,奶酪,食用油,增重粉,蛋白质食品,能量棒,功能饮料例如运动和保健饮料,以及高卡路里饮料,航天员食品,管饲料等。
本发明还涉及含有根据本发明的虾青素组合物的饲料,其中虾青素组合物的浓度对应于批准用于各饲料的饲料中的虾青素含量。通常,按虾青素计算,根据本发明的组合物浓度是1-500mg/kg各饲料。
饲料中的典型组分是碳水化合物源,特别是谷物粉例如小麦或玉米粉、大豆粉,但是还有糖和糖醇,还有蛋白类组分例如大豆浓缩物、鱼粉,谷蛋白例如玉米或小麦谷蛋白,油和脂肪例如上述的可食用油,但是还有其他植物或动物来源的可食用脂肪,还有营养物质例如游离氨基酸、其盐、维生素和微量元素,以及任选的加工助剂例如助流剂、抗结剂、惰性填充剂等,以及任选的防腐剂。典型的鱼饲料组合物以例如3-20重量%的量包含例如谷物粉,以例如1-30重量%的量包含谷蛋白,以例如10-50重量%的量包含一种或多种蛋白质源诸如大豆浓缩物和/或鱼粉,以例如10-50重量%的量包含脂肪和/或油,以例如0.1-2重量%的总量任选地包含一种或多种维生素,以及以例如0.1-5重量%的量任选地包含氨基酸,在各情况中基于饲料组分的总量。
通过向饲料中加入所需量的根据本发明的食品或饲料添加剂,成功制备食品或饲料。当在制备食品或饲料时,添加剂的加入可在食品或饲料生产期间进行或者通过加入至食品或饲料组分中而进行。
所述饲料的具体实施方案涉及饲料丸片(pellets),尤其是用于鱼食的饲料丸片,将其装载根据本发明可得到的虾青素衍生物溶液。基于饲料的总重量,并按虾青素计算,所述丸片通常以10-200ppm的量含有根据本发明的虾青素组合物。通常,优选在减压条件下,通过用根据本发明的虾青素组合物溶液喷洒传统丸片而制备所述丸片,其中喷洒可以持续完成或者优选地分批完成。例如,可能的是将传统丸片引入到适当容器中,向容器施加真空,然后喷洒虾青素组合物在适合于食品的油中的溶液,并且混合丸片,随后向容器中引入空气。以所述方式实现油溶液向丸片的均匀渗透。任选地,可能的是再施加真空,并再以上述方式,喷洒虾青素组合物在适合于食品的油中的溶液。以所述方式,得到在核心含有油和根据本发明的虾青素组合物的丸片。
本发明还涉及食品补充剂。这些食品补充剂包含配制形式的根据本发明的虾青素组合物,即除根据本发明的虾青素组合物之外,其包含至少一种批准用于食品补充剂的辅助剂。这些主要包括上述与食品添加剂相关的辅助剂例如载体、分散剂、抗氧化剂、防腐剂和着色剂,以及用于制备所希望施用形式需要的其他辅助剂。
食品补充剂的经典施用方式是粉状(pulverulent)形式、粉末、颗粒、片剂特别是膜包衣片剂、锭剂、囊剂(sachets)、扁囊剂(cachets)、糖包衣片剂、胶囊剂例如硬-或软-明胶胶囊剂、泡腾片剂和泡腾粉剂。
食品补充剂中虾青素组合物的量通常是每单位剂量0.5-100mg特别是1-50mg,所述量是根据虾青素计算的。
本发明的主题是文中所述的虾青素组合物,作为药物和药物制剂(=药物组合物)的组分而用于治疗用途。其中根据本发明的组合物可应用的适当的适应症是上述的适应症。
在治疗范围内,所述化合物根据本发明的用途包括方法。文中,将通常根据药物和兽医实践配制的有效量的根据本发明的虾青素组合物施用至要治疗的个体,优选至哺乳动物,特别是人、农场动物或家养动物。所述治疗是否是适应的,以及其应采用的形式,取决于个体病例,并需要医学评价(诊断),所述考虑现有体征、症状和/或功能失常,患某些体征的风险、症状和/或功能失常,以及其他因素。
通常,通过每天一次或多次施用进行治疗,任选与其他活性物质或含活性物质的制剂一起或交替施用,从而将优选大约0.1-50mg/kg体重特别是0.5-10mg/kg体重或者1-1000mg特别是2-200mg的日剂量(在各情况中根据虾青素计算的)施用至要治疗的个体,优选通过口服施用。
本发明还涉及药物制剂下文也称作药物组合物的生产,其用于个体优选哺乳动物,特别是人、农场动物或家养动物的治疗。因此,通常将根据本发明的虾青素组合物以药物制剂的形式施用,其包含药学上可接受的辅助剂即赋形剂、根据本发明的虾青素组合物和任选的一种或多种其他活性物质。将所述制剂任选地通过口服途径施用。
适当的药物制剂的示例包括固体药物形式例如粉状形式、粉末、颗粒、片剂特别是膜包衣片剂、锭剂、囊剂、扁囊剂、糖包衣片剂、胶囊剂例如硬-或软-明胶胶囊剂、泡腾片剂和泡腾剂粉,半固体药物形式例如软膏、乳膏剂、水凝胶剂、糊剂或贴剂,以及液体药物形式例如溶液剂、乳剂特别是水包油乳剂、混悬剂例如洗剂、滴眼剂和滴耳剂。还可以进一步使用脂质体或微囊。
当生产药物制剂时,通常将根据本发明的虾青素组合物与赋形剂混合或者用赋形剂稀释。赋形剂可以是固体、半固体或液体物质,其作为活性物质的溶媒、载体或媒介。根据本发明的组合物通常以相当于日剂量或者日剂量的一部分例如日剂量的一半、三分之一或四分之一的量包含虾青素组合物。药物制剂中虾青素组合物的量通常是每单位剂量0.5-200mg特别是1-100mg,根据虾青素计算。
适当的赋形剂列于相关的医学专著中。此外,制剂可包含药学上可接受的载体或惯用辅助剂例如助流剂;润湿剂;乳化剂和助悬剂;防腐剂;抗氧化剂;抗刺激剂;螯合剂;包衣助剂;乳化稳定剂;成膜剂;凝胶形成剂;掩味剂;矫味剂;树脂;凝胶;溶剂;助溶剂;中和剂;扩散促进剂;色素;季铵化合物;再脂化剂和超脂化剂;软膏剂、乳膏剂或油剂的原料;硅酮衍生物;扩散助剂;稳定剂;杀菌剂;栓剂基质;片剂辅助剂例如粘合剂、填充剂、助流剂、崩解剂或包衣剂;抛射剂;干燥剂;遮光剂;增稠剂;蜡;增塑剂和白色矿物油。就此,制剂是基于专家知识的,如同例如Fiedler,H.P.,Lexikon der Hilfsstoffe für Pharmazie,Kosmetik und angrenzende Gebiete[Encyclopedia of adjuvants for Pharmacy,Cosmetics and Related Fields],第4版,Aulendorf:ECV-Editio-Kantor-Verlag,1996中所述的。
对于下述研究,利用下述的虾青素组合物。术语面积%代表经HPLC测定的面积百分数。
虾青素单油酸酯具有下述性质:
虾青素单油酸酯含量>91重量%;
虾青素骨架中的E/Z异构体分布>45面积%全-E异构体;
对映体纯度:>95%ee 3S,3'S对映体;
反式脂肪酸酯含量>40重量%。
虾青素二油酸酯具有下述性质:
虾青素二油酸酯含量>93重量%;
虾青素骨架中的E/Z分布>60面积%全-E异构体;
对映体纯度:>95%ee 3S,3'S对映体;
反式脂肪酸酯含量60重量%。
天然虾青素产品
其来源于雨生红球藻(Haematococcus pluvialis)的虾青素(主要为3S,3'S对映体)与C16-C22-脂肪酸的单酯和二酯的混合物,具有下述组成(根据HPLC-MS测定的,以面积%表示的数据)
1.6%虾青素-C18:4-单酯
9.7%虾青素-C18:3-单酯
15.0%虾青素-C18:2-单酯
28.7%虾青素-C18:1-单酯
5.3%虾青素-C18:0-单酯
剩余的39.7%是77个未确定的峰,各峰<2面积%,然而,其主要为虾青素单酯和二酯。
制备实施例1:虾青素单棕榈酸酯的制备
将3g(11.7mmol)棕榈酸引入到47.37ml(53g,740mmol)二氯甲烷中。将2.85g(17.55mmol)1,1‘-羰基二咪唑(CDI)在室温下分三批加入,每批间隔5分钟。继续搅拌过夜,并在第二天加入3.49g(5.85mmol)虾青素(3S,3'S对映体,ee>95%)。6小时后,向反应混合物中,加入133.8μl乙酸,并在室温下搅拌过夜。20小时后,经薄层色谱(硅胶,流动相环己烷/乙酸乙酯=1:2)检测一样品。薄层色谱显示所用的部分虾青素已转化为虾青素单棕榈酸酯。仅检测到非常少量的虾青素二棕榈酸酯。
通过将反应混合物在硅胶上利用体积比1:2的环己烷/乙酸乙酯色谱分离,可从试剂和未反应的虾青素中分离虾青素单棕榈酸酯。用所述方式,可得到虾青素单棕榈酸酯,其具有>80重量%特别是>90重量%的纯度。
可以类似地得到>80重量%特别是>90重量%的纯度的虾青素单油酸酯。
生物利用度试验
通过测定虾青素在小型猪中的血浆水平,研究生物利用度。将历经96h的血清中的血浆浓度积分(AUC)测定为生物利用度的量度。
所有虾青素衍生物以橄榄油溶液施用:
制剂1:虾青素单油酸酯,在橄榄油中4.2重量%(按游离虾青素计算)
制剂2:虾青素二油酸酯,在橄榄油中3.1重量%(按游离虾青素计算)
制剂3:天然虾青素产品,在橄榄油中2.4重量%(按游离虾青素计算)
本项研究在3只4-5月龄的体重9.5–10.5kg的雄性小型猪上进行。为了采集血样,将导管植入到所有小型猪的股静脉中。小型猪中的两只(2号猪和3号猪)另外具有植入到颈静脉的导管。研究期间,每天用生理盐水冲洗导管。
未处理期间,将小型猪喂食用于小型猪的市售配给品(ration)(SDS,Essex,UK)。在工作日的上午和下午,以及周末的清晨和正午前,将配给品喂食。
在处理日,将已用20%玉米油强化的高脂肪配给品喂食。为此,将224g市售小型猪配给品与54g玉米油混合。1号猪在紧临第1次和第2次处理前接受140g高脂饮食,并在紧临第1次和第2次处理后接受140g,并在第3次处理前2h接受140g,并在第3次处理后1h接受140g。2号猪和3号猪在各情况中在紧临第1次和第2次处理前接受170g高脂配给品,并在紧临第1次和第2次处理后接受110g,并在第3次处理前2h接受170g,并在第3次处理后1h接受110g。
将处理通过1周的间隔各自分开。处理方案如表1中所示:
表1:处理方案
第1次处理 | 第2次处理 | 第3次处理 | |
1号猪 | 制剂3 | 制剂2 | 制剂1 |
2号猪 | 制剂1 | 制剂3 | 制剂2 |
3号猪 | 制剂2 | 制剂1 | 制剂3 |
对于处理,以单一剂量,利用胃管将制剂施用至各猪。单一剂量是50mg/kg虾青素。紧临施用之前和施用之后2h、6h、7h、8h、9h、10h、11h、12h、1h、24h、32h、48h、56h、72h和96h,通过股静脉,从猪采集大约2ml血液。将样品贮存在冰上,并在采样后30min内,在1500g和4-8℃下离心10min。将血浆转移至无菌密封的聚丙烯容器(Micronic,Lelystadt)中,并在低于-75℃的温度下贮存,直到分析。经HPLC,在WIL Research,Den Bosch NL下测定血浆中的虾青素水平。结果显示于下面的表2中。显示的数据是3只受试猪的平均值。
表2:
tlast=直到值达不到检测水平的期间
tmax=最大血清水平的期间
Cmax=最大血清水平
Clast=值达不到检测水平之前的浓度
AUClast=直到值达不到检测水平之前的时间点的浓度积分
AUC∞=外延的浓度积分
t1/2=半衰期
Claims (18)
1.虾青素组合物在食品、食品补充剂或饲料中的用途,其中基于组合物中虾青素和虾青素衍生物的总重,虾青素组合物含有至少50重量%的虾青素与脂肪族C10-C22-单羧酸的单酯,其中虾青素组合物中存在的至少90重量%的单酯是精确地与一种脂肪族无支链C10-C22-单羧酸的单酯。
2.根据权利要求1所述的用途,其中至少90重量%的虾青素单酯是虾青素精确地与一种脂肪族无支链C16-C22-单羧酸的单酯。
3.根据上述权利要求中任何一项所述的用途,其中至少90重量%的虾青素单酯是与至少一种单不饱和脂肪族无支链C10-C22-单羧酸的单酯,包括与该C10-C22-单羧酸的顺/反混合物和双键异构体混合物的单酯。
4.根据权利要求3所述的用途,其中所述至少一种单不饱和脂肪酸选自C18-1、C18-2、C18-3和C18-4脂肪酸。
5.根据权利要求4所述的用途,其中至少90重量%的虾青素单酯是与C18-1脂肪酸的单酯。
6.根据权利要求3-5中任何一项所述的用途,其中虾青素单酯中存在的低于60重量%的不饱和脂肪酸是以反式-脂肪酸存在。
7.根据上述权利要求中任何一项所述的用途,其中至少40重量%的虾青素单酯是以全-反式虾青素单酯形式存在。
8.根据上述权利要求中任何一项所述的用途,其中至少90重量%的虾青素单酯是虾青素单酯的形式存在,所述虾青素在位置3和3’的不对称中心分别具有(S)或(R)构型。
9.食品添加剂、饲料添加剂或食品补充剂形式的组合物,其包含根据权利要求1-8中任何一项所述的虾青素组合物,以及适合于食品、饲料或食品补充剂的辅助剂。
10.根据权利要求9所述的组合物,其选自虾青素组合物和适合于食品或饲料的油或脂肪的溶液和混悬液。
11.粉末形式的根据权利要求9所述的组合物,其含有虾青素组合物和保护性胶体。
12.食品补充剂形式的根据权利要求9所述的组合物,其用于口服施用。
13.食品,其包含根据权利要求1-8中任何一项所述的虾青素组合物,其中虾青素组合物的浓度相应于批准用于食品的虾青素含量。
14.饲料,其包含根据权利要求1-8中任何一项所述的虾青素组合物,其中虾青素组合物的浓度相应于批准用于饲料的虾青素含量。
15.食品或饲料的制备方法,其包含将根据权利要求1-8中任何一项所述的虾青素组合物加入到传统食品或饲料中。
16.根据权利要求1-8中任何一项所述的虾青素组合物,其作为药物以及作为药物制剂的组分用于治疗用途。
17.根据权利要求16所述的虾青素组合物,其用于治疗或预防关节疾病、眼部疾病、皮肤病、皮肤衰老、心脏病、血管疾病、炎性疾病、肿瘤疾病、细菌感染、2-型糖尿病和相关后遗症,以及退行性神经病症,用于改善雄性生殖、记忆、身体健康和注意力,以及用于增强免疫系统。
18.药物制剂,其包含根据权利要求1-8中任何一项所述的虾青素组合物,以及至少一种药学上适当的辅助剂。
Applications Claiming Priority (3)
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EP15159828.1 | 2015-03-19 | ||
EP15159828 | 2015-03-19 | ||
PCT/EP2016/055919 WO2016146801A1 (de) | 2015-03-19 | 2016-03-18 | Astaxanthinzusammensetzungen (i) |
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CN107427029A true CN107427029A (zh) | 2017-12-01 |
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CN201680016343.4A Pending CN107427029A (zh) | 2015-03-19 | 2016-03-18 | 虾青素组合物(i) |
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US (1) | US20180110741A1 (zh) |
EP (1) | EP3270904B1 (zh) |
JP (1) | JP2018510634A (zh) |
CN (1) | CN107427029A (zh) |
AU (1) | AU2016232096A1 (zh) |
BR (1) | BR112017019831A2 (zh) |
WO (1) | WO2016146801A1 (zh) |
Cited By (1)
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CN114513963A (zh) * | 2019-10-11 | 2022-05-17 | 帝斯曼知识产权资产管理有限公司 | 新型类胡萝卜素饲料添加剂 |
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US10836718B2 (en) | 2016-11-25 | 2020-11-17 | Basf Se | Process for preparing astacene |
WO2022091995A1 (ja) * | 2020-10-26 | 2022-05-05 | Eneos株式会社 | シス型アスタキサンチンを含む機能性食品用組成物 |
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JP2001114683A (ja) * | 1999-10-08 | 2001-04-24 | Higashimaru Shoyu Co Ltd | プロテインキナーゼ阻害剤 |
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DE10140180A1 (de) | 2001-08-22 | 2003-03-06 | Basf Ag | Verfahren zur selektiven Reduktion von Alkinverbindungen |
JP2007238441A (ja) * | 2004-12-03 | 2007-09-20 | Fuji Chem Ind Co Ltd | アスタキサンチンを有効成分とする体脂肪減少用組成物 |
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2016
- 2016-03-18 EP EP16712774.5A patent/EP3270904B1/de not_active Not-in-force
- 2016-03-18 BR BR112017019831A patent/BR112017019831A2/pt not_active Application Discontinuation
- 2016-03-18 JP JP2017549002A patent/JP2018510634A/ja not_active Withdrawn
- 2016-03-18 CN CN201680016343.4A patent/CN107427029A/zh active Pending
- 2016-03-18 US US15/559,306 patent/US20180110741A1/en not_active Abandoned
- 2016-03-18 AU AU2016232096A patent/AU2016232096A1/en not_active Abandoned
- 2016-03-18 WO PCT/EP2016/055919 patent/WO2016146801A1/de active Application Filing
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CN114513963A (zh) * | 2019-10-11 | 2022-05-17 | 帝斯曼知识产权资产管理有限公司 | 新型类胡萝卜素饲料添加剂 |
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Publication number | Publication date |
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EP3270904B1 (de) | 2019-03-13 |
JP2018510634A (ja) | 2018-04-19 |
WO2016146801A1 (de) | 2016-09-22 |
BR112017019831A2 (pt) | 2018-05-29 |
EP3270904A1 (de) | 2018-01-24 |
AU2016232096A1 (en) | 2017-10-05 |
US20180110741A1 (en) | 2018-04-26 |
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