CN106029789A - 花青素复合物 - Google Patents
花青素复合物 Download PDFInfo
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- CN106029789A CN106029789A CN201580010394.1A CN201580010394A CN106029789A CN 106029789 A CN106029789 A CN 106029789A CN 201580010394 A CN201580010394 A CN 201580010394A CN 106029789 A CN106029789 A CN 106029789A
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0092—Dyes in solid form
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
- A61K31/353—3,4-Dihydrobenzopyrans, e.g. chroman, catechin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/69—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
- A61K47/6949—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes
- A61K47/6951—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes using cyclodextrin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
- C08B37/0012—Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof
- C08B37/0015—Inclusion compounds, i.e. host-guest compounds, e.g. polyrotaxanes
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B61/00—Dyes of natural origin prepared from natural sources, e.g. vegetable sources
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0083—Solutions of dyes
Abstract
本发明的主题是一种由花青素和甲基化的β环糊精构成的复合物,该复合物能够配制为含水溶液以及配制为固体,以及本发明的主题是一种用于制备这种复合物的方法。根据本发明的复合物是仓储稳定的并且能良好地配制成含水溶液。
Description
技术领域
本发明涉及一种由花青素和甲基化的环糊精构成的复合物。
背景技术
花青素是细胞色素的染料,染料在通常较高的有胚植物中存在。花青素是无糖的(糖苷配基)并且与含糖的花色素苷紧密相关。花青素是染料并且具有抗氧化的特性。
从WO 2013/144297 A1中已经已知:花青素与磺基烷基醚β环糊精复合。
发明内容
本发明基于以下目的:提供可良好操作的、可配置的并且仓储稳定且相对浓缩形式的花青素。
目的通过一种由花青素和甲基化的β环糊精构成的复合物实现。
首先阐述在本发明的范围中应用的术语。
花青素具有如下描述的基本结构。
该式中的取代基选自:氢、羟基基团和甲氧基基团。
环糊精是由α-1,4糖苷结合的葡萄糖分子构成的环形的低聚糖。β环糊精具有七个葡萄糖单元。在甲基化的β环糊精中,葡萄糖单元的羟基基团设有甲基基团。根据本发明,通常仅将β环糊精的21个羟基基团中的一部分甲基化。
甲基化的β环糊精的制备对于本领域技术人员是常见的,相应的产品例如从Wacker Chemie以名称获得。
本发明认识到:花青素、如飞燕草素令人惊讶地以远高于现有技术中与其他的环糊精复合的浓度而与甲基化的β环糊精复合。因此这尤其是令人惊讶的,因为例如在WO 2013/144297 A1中执行与一系列的环糊精的复合实验,在复合实验中,具有花青素的复合物的浓度或者加荷以数量级的形式降低。
因此,本发明实现:以高的浓度进而高的掺杂优选以含水的或水溶的形式提供花青素,进而以简单的方式使得能够进行活体内施用、例如体内施用。此外,本发明的特别的优点是:甲基化的环糊精、尤其RAMEB以其所使用的浓度不是或者最多或是轻微毒性的,尤其在活体内不触发或最多触发轻微的且不令人担心的溶血作用。
优选地,β环糊精以甲基基团取代的取代度为10至15、优选为11至14、更优选为12至13。
尤其优选地,将RAMEB(随机甲基化-β环糊精)用作为甲基化的β环糊精。其是取代度为大约每个糖单元1.8个甲基基团或每个环糊精环12.5个甲基基团(取代度DS为大约12.5)的统计甲基化的、β环糊精。RAMEB是例如由Wacker Chemie以名称W7M Pharma市售的。
根据本发明的复合的花青素优选选自以橙苷色素、矢车菊色素、飞燕草色素、欧天芥菜色素、木樨黄定、天竺葵色素、锦葵色素、芍药色素、矮牵牛色素和玫瑰色素构成的组。
符合上面描述的式I的化学结构具有下面取代模式。
在本发明的范围内,尤其优选的是具有飞燕草色素的复合物。
此外,本发明的主题是根据本发明的复合物的含水溶液。
本发明的另一主题是一种用于制备根据本发明的复合物以及相应的含水溶液的方法,方法具有如下步骤:
a.制备甲基化的β环糊精的含水溶液,
b.添加花青素并且混合,以制备复合物。
在步骤a)中,优选制备含水溶液,其包含10至60重量百分比的、优选20至50重量百分比的、更优选30至50重量百分比的所使用的环糊精。
在本发明的范围中尤其优选的是:含水溶液的pH值在添加花青素、优选飞燕草色素期间或之后、然而优选在添加其之前调节到7或更低的pH值、优选6至7的pH值。证实:在该pH值的情况下,能够在含水溶液中设定复合物的高浓度。
尤其优选的是,花青素的浓度优选以氯化物计算为至少10mg/ml、更优选至少20mg/ml、更优选至少50mg/ml、更优选至少80mg/ml。能够无问题地达到例如100mg/ml的浓度。
同样地,本发明的主题是一种固体,其包含由花青素和甲基化的β环糊精构成的复合物,固体通过从含水溶液中去除溶剂来获得。从含水溶液中去除溶剂能够通过对于本领域技术人员常用的方法、例如升华干燥(冷冻干燥)来进行。该根据本发明的固体是长期仓储稳定的,并且能够无问题地再次与水混合成含水的进而可在活体内施用的溶液。根据本发明的含水溶液和固体具有高的仓储稳定性。
在根据本发明的制造期间,通过搅拌混合含水溶液的组成部分,对于混合的优选的时间段为2至20h。优选地,在暗室中工作,以便避免光引发的氧化。
具体实施方式
下面阐述本发明的实施例。
1.所使用的材料
从Wacker Chemie获得RAMEB并且从Extrasynthese公司获得氯化飞燕草色素。
2.确定飞燕草色素含量
为了确定含飞燕草色素的组分中的氯化飞燕草色素的含量使用反相HPLC方法。在此,使用如下试剂:
清洁的水
用于色层分析法的甲醇
甲酸,分析用(p.a.)
1M盐酸作为当量标准的溶液。
将Waters X BridgeTM C18.335μl,150mm x 4.6mm用作为柱。
移动相如下:
通道A:水950ml、甲醇50ml、甲酸10ml
通道B:水50ml、甲醇950ml、甲酸10ml
应用如下的梯度程度:
时间[分钟] | 通道B的百分比 |
0 | 0 |
5 | 0 |
25 | 60 |
30 | 100 |
停止时间:35分钟
再运行时间(延后时间):8分钟
流速:1ml/min
注射体积:20μl
柱温度:30℃+/-2℃
紫外可见吸收光谱检测器:用于化验的为530μm,用于检测杂质的为275μm
能量计:面积
溶液和试样准备
稀释溶液1:由100ml甲醇和2.6ml 1M HCL构成的混合物
稀释溶液2:由100ml百分之四十的甲醇和2.6ml 1M HCL构成的混合物
标定溶液:通过称重10mg氯化飞燕草色素装入10ml烧瓶中并且溶液在稀释溶液1中来制备飞燕草色素的基准溶液。在溶解之后,借助稀释溶液2稀释大约10倍以制备大约0.1mg/ml的浓度。
以简单的方式和方法制备检验标定溶液。标定溶液立即借助于HPLC来分析,因为氯化飞燕草色素在溶液中是不稳定的。
制备测试溶液:
为了确定根据本发明制备的固体(制备参见下文)的飞燕草色素含量,将大约50mg该组分称重装入10ml烧瓶中。随后,溶液在稀释溶液2中并且借助相同的稀释溶液2进一步稀释至调节出大约0.1mg/ml的飞燕草色素浓度。
试样中的飞燕草色素含量的确定借助Agilent ChemStation软件利用借助上面描述的外部标准进行标定来计算。
实例1
飞燕草色素与RAMEB复合
在水中制备40重量百分比的RAMEB的溶液。
将1ml含水的环糊精溶液填入到玻璃烧瓶中。随后,添加250mg氯化飞燕草色素。
将悬浮液在30℃的情况中在暗室中搅拌4小时。随后,通过具有0.8μm孔大小的膜片过滤器进行过滤。
实例2
根据本发明的固体的制备
根据实例1的溶液被冷冻并且随后在-48℃的情况中和大约10.3Pa(77mTorr)的压力下升华干燥。获得0.36g的固体,其具有31.1重量百分比的飞燕草色素含量。
该固体以高的浓度以仓储时间更长且能够容易地在活体内施用的形式提供飞燕草色素。复合物占飞燕草色素的含量远高于在现有技术中的情况。
Claims (11)
1.一种由花青素和甲基化的β环糊精构成的复合物。
2.根据权利要求1或2所述的复合物,其特征在于,所述β环糊精以甲基基团取代的取代度为10至15、优选为11至14、更优选为12至13。
3.根据权利要求2所述的复合物,其特征在于,甲基化的所述β环糊精是RAMEB。
4.根据权利要求1至3中任一项所述的复合物,其特征在于,所述花青素选自以橙苷色素、矢车菊色素、飞燕草色素、欧天芥菜色素、木樨黄定、天竺葵色素、锦葵色素、芍药色素、矮牵牛色素和玫瑰色素构成的组。
5.根据权利要求4所述的复合物,其特征在于,所述花青素是飞燕草色素。
6.一种根据权利要求1至5中任一项所述的复合物的含水溶液。
7.根据权利要求6所述的含水溶液,其特征在于,所述花青素的浓度以氯化物计算为至少10mg/ml、更优选至少20mg/ml、更优选至少50mg/ml、更优选至少80mg/ml。
8.一种固体,包含由花青素和甲基化的β环糊精构成的复合物,所述固体通过从根据权利要求6或7中任一项所述的含水溶液中去除溶剂来获得。
9.一种用于制备花青素和甲基化的β环糊精构成的复合物的方法,所述方法具有如下步骤:
a.制备甲基化的β环糊精的含水溶液,
b.添加花青素并且混合,以制备所述复合物。
10.根据权利要求9所述的方法,其特征在于,在步骤a)中制备的溶液包含10至60重量百分比的、优选20至50重量百分比的、更优选30至50重量百分比的甲基化的所述β环糊精。
11.根据权利要求9或10所述的方法,其特征在于,在步骤b)中的混合以2至20h的时间段进行。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP14157248.7A EP2913366A1 (de) | 2014-02-28 | 2014-02-28 | Anthocyanidin-Komplex |
EP14157248.7 | 2014-02-28 | ||
PCT/EP2015/054084 WO2015128437A1 (de) | 2014-02-28 | 2015-02-26 | Anthocyanidin-komplex |
Publications (2)
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CN106029789A true CN106029789A (zh) | 2016-10-12 |
CN106029789B CN106029789B (zh) | 2018-10-12 |
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CN201580010394.1A Active CN106029789B (zh) | 2014-02-28 | 2015-02-26 | 花青素复合物 |
Country Status (9)
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US (2) | US20170014377A1 (zh) |
EP (2) | EP2913366A1 (zh) |
JP (1) | JP6488315B2 (zh) |
KR (1) | KR102320130B1 (zh) |
CN (1) | CN106029789B (zh) |
CA (1) | CA2940793A1 (zh) |
DK (1) | DK3110890T3 (zh) |
ES (1) | ES2665291T3 (zh) |
WO (1) | WO2015128437A1 (zh) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106459608A (zh) * | 2014-08-02 | 2017-02-22 | 株式会社Lg化学 | 染料复合物、光转换膜和包括其的电子装置 |
CN112062877A (zh) * | 2020-06-09 | 2020-12-11 | 北京博诺安科科技有限公司 | 一种甲基化-β-环糊精及其制备、表征方法和应用 |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9925274B2 (en) | 2012-11-15 | 2018-03-27 | Sapiotec Gmbh | Delphinidin complex as an antiphlogistic or immunosuppressive active ingredient |
EP2931287B1 (de) | 2012-12-11 | 2017-10-04 | Sapiotec GmbH | Delphinidin zur bekämpfung von melanomzellen |
CN105213367A (zh) * | 2015-10-28 | 2016-01-06 | 邓宏伟 | 越橘花青素组合物及其在制备防治近视药物或食品的应用 |
CN114957185A (zh) * | 2022-05-31 | 2022-08-30 | 安徽大学绿色产业创新研究院 | 一种提高花青素稳定性的方法 |
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WO2013144303A1 (de) * | 2012-03-30 | 2013-10-03 | Sapiotec Gmbh | Antibakterielle wirkstoffe auf der basis anthocyanidin- cyclodextrin- komplexen |
WO2013144297A1 (de) * | 2012-03-30 | 2013-10-03 | Sapiotec Gmbh | Anthocyanidin-komplex |
CN103491981A (zh) * | 2010-12-31 | 2014-01-01 | 东塘实验室有限公司 | 含有环糊精的细胞水合组合物 |
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2014
- 2014-02-28 EP EP14157248.7A patent/EP2913366A1/de not_active Withdrawn
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2015
- 2015-02-26 DK DK15706257.1T patent/DK3110890T3/en active
- 2015-02-26 CN CN201580010394.1A patent/CN106029789B/zh active Active
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JP2017510562A (ja) | 2017-04-13 |
US20170014377A1 (en) | 2017-01-19 |
KR102320130B1 (ko) | 2021-10-29 |
US20210030713A1 (en) | 2021-02-04 |
EP3110890A1 (de) | 2017-01-04 |
JP6488315B2 (ja) | 2019-03-20 |
WO2015128437A1 (de) | 2015-09-03 |
ES2665291T3 (es) | 2018-04-25 |
KR20160124134A (ko) | 2016-10-26 |
EP2913366A1 (de) | 2015-09-02 |
CN106029789B (zh) | 2018-10-12 |
DK3110890T3 (en) | 2018-04-23 |
EP3110890B1 (de) | 2018-01-10 |
CA2940793A1 (en) | 2015-09-03 |
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