CN107522761B - 一种分离纯化飞燕草素-3-o桑布双糖苷的方法及其降糖用途 - Google Patents
一种分离纯化飞燕草素-3-o桑布双糖苷的方法及其降糖用途 Download PDFInfo
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Abstract
本发明公开了一种分离纯化飞燕草素‑3‑O桑布双糖苷的方法及其降糖用途。仅通过大孔树脂及固相萃取即可从玫瑰茄中大量制备得到纯度为96%的飞燕草素‑3‑O‑桑布双糖苷,方法简单、快速,成本低廉,使之易于工业化生产。体外细胞实验表明,飞燕草素‑3‑O‑桑布双糖苷能够通过促进糖原合成来促进细胞对葡萄糖的消耗,从而起到降糖作用。因此,飞燕草素‑3‑O‑桑布双糖苷可作为降糖功能食品、保健品或降糖药物用于糖代谢异常相关疾病的防治,本发明能为综合开发利用我国玫瑰茄资源提供新的思路。
Description
技术领域
本发明涉及天然产物的分离纯化及医药领域,特别涉及一种从天然来源的玫瑰茄中分离纯化飞燕草素-3-O-桑布双糖苷的方法,以及飞燕草素-3-O-桑布双糖苷在制备降糖功能食品、保健品或降糖药物中的应用。
背景技术
糖尿病是当前威胁人类健康最重要的非传染性疾病之一。糖尿病往往会并发其他代谢综合症,如高血脂、肾衰竭和炎症等,给人类带来巨大的肉体与精神上的痛苦。糖尿病分为两种:I型糖尿病(胰岛素依赖)和II型糖尿病(非胰岛素依赖)。根据国际糖尿病联盟IDF统计,2011年全球糖尿病患者人数高达3.7亿,其中II型糖尿病患者人数占总糖尿病患者人数的90%。到2030年,预计全球将有近5.5亿糖尿病患者。因此,对于研究糖尿病及其并发症的预防及控制策略刻不容缓。
玫瑰茄是锦葵科木槿属的一年生草本植物,广布于热带和亚热带地区,原产于西非、印度,目前在我国的广东、广西、福建、云南、台湾等地均有栽培。玫瑰茄的花萼肉质多汁,并可用于提取天然食用色素(花色苷)。现代研究表明玫瑰茄含有黄酮、原儿茶酸、花青素、异黄酮以及丰富的氨基酸、维生素、等活性物质,这些活性物质能够有效降低胆固醇和甘油三脂、抑制低密度脂蛋白的氧化等功能。因此玫瑰茄具有巨大的商业应用价值。
发明内容
申请人在研究中发现玫瑰茄中富含飞燕草素-3-O-桑布双糖苷,且飞燕草素-3-O-桑布双糖苷能够促进细胞对葡萄糖的消耗及促进细胞糖原的合成,具有一定的降糖活性。基于此,本发明提供了一种从玫瑰茄中大量分离制备高纯度的飞燕草素-3-O-桑布双糖苷的方法,并提供飞燕草素-3-O-桑布双糖苷在制备降糖功能食品、保健品或降糖药物中的应用。
本发明的技术方案如下:
本发明首先公开了一种分离纯化飞燕草素-3-O桑布双糖苷的方法,其步骤如下:
1)将干燥的玫瑰茄与酸性乙醇溶液按照料液比1g:4mL~1g:10mL混合后避光搅拌12-24h,过滤,滤液离心取上清液,上清液在40-45℃下真空旋转蒸发除去乙醇,得到花色苷粗提液Ⅰ;
2)用乙酸乙酯对花色苷粗提液Ⅰ进行萃取,静置分层,收集水相,重复萃取2-6次,收集并合并水相,40-45℃真空旋转蒸发除去残留的乙酸乙酯,得到花色苷粗提液Ⅱ;
3)将所述花色苷粗提液Ⅱ用大孔树脂纯化,纯化的步骤为:将乙醇浸泡12-48h后的大孔树脂装入层析柱中,用水洗至无醇味后,再用HCl溶液和NaOH溶液进行活化,然后将玫瑰茄花色苷粗提物Ⅱ以0.5-1BV/h的流速注入大孔树脂,使得吸附花色苷的树脂的体积为树脂总体积的1/2至4/5,之后使用去离子水以5-8BV/h的流速淋洗树脂,再分别使用3-5BV的5%和10%的乙醇溶液以2-3BV/h的流速洗脱花色苷,收集10%的乙醇溶液洗脱液,40-45℃下真空旋转蒸发除去乙醇,得到花色苷浸膏;所述5%和10%的乙醇溶液中含有体积比为1.5%的盐酸;
4)将上述浸膏用少量去离子水溶解得到样品液,使用固相萃取柱纯化,纯化的步骤为将固相萃取柱使用甲醇活化,然后使用6-10BV去离子水清洗柱体至无甲醇残留,将样品液注入固相萃取柱柱中,用6-10BV的含1.5%甲酸的去离子水冲洗柱体,然后使用5-8BV的5%乙腈水溶液洗脱,所述乙腈水溶液中含1.5%甲酸,收集乙腈洗脱液,40-45℃下真空旋转蒸发,得到飞燕草素-3-O-桑布双糖苷浸膏,用少量去离子水溶解,之后冷冻干燥得到飞燕草素-3-O-桑布双糖苷粉末。
优选的,所述步骤1)中的酸性乙醇溶液是体积百分比为50%-80%的乙醇溶液,乙醇溶液中含酸体积百分比为0.1%-2%,所述的酸为盐酸、甲酸或乙酸中的一种或多种。
优选的,所述步骤1)中的过滤采用三层纱布过滤,滤液离心的方法为转速4000r/min,离心时间为15min。
优选的,所述步骤2)中的每次萃取过程中,乙酸乙酯与花色苷粗提液Ⅰ的体积比为1:1。
优选的,所述大孔树脂为AB-8大孔树脂,比表面积为480-520m2/g,平均孔径为13-14nm,粒径范围在0.3-1.25mm。
优选的,所述步骤3)用HCl溶液和NaOH溶液进行活化的具体步骤为:用2-6倍BV的4%HCl溶液,以3-5BV/h的流速通过树脂层,并浸泡3小时,而后用去离子水以同样流速洗至水洗液呈中性,用2-6倍柱体积4%的NaOH溶液,以3-5BV/h的流速通过树脂层并浸泡3小时,而后用去离子水以同样流速洗至水洗液呈中性。
优选的,所述固相萃取柱为C18色谱柱。优选为C18Sep-Pak cartridge固相萃取柱(Waters Corporation)。
优选的,所述步骤4)样品液注入固相萃取柱的上样体积为柱体积的2/3。
本发明还公开了一种所述飞燕草素-3-O-桑布双糖苷粉末在制备降糖功能食品或降糖药物中的应用。
本发明所建立的方法,仅使用大孔树脂柱和固相萃取柱(C18)即可从玫瑰茄中大量制备得到纯度为96%的飞燕草素-3-O-桑布双糖苷。相对其他液相色谱及逆流色谱方法,本发明中涉及方法更为简单、快速,成本低廉,易于工业化生产。
本发明所述方法制备得到的飞燕草素-3-O-桑布双糖苷展现出显著的葡萄糖消耗活性,即促进细胞对葡萄糖的消耗,从而起到降糖作用。
附图说明
图1为实施例2中纯化后的飞燕草素-3-O-桑布双糖苷高效液相色谱图;
图2为实施例2中飞燕草素-3-O-桑布双糖苷的化学结构式;
图3为实施例5中飞燕草素-3-O-桑布双糖苷分离纯化的高速逆流色谱图;
图4为实施例6中飞燕草素-3-O-桑布双糖苷(D3S)促进细胞对葡萄糖消耗作用;
图5为实施例7中飞燕草素-3-O-桑布双糖苷(D3S)促进细胞糖原合成作用。
具体实施方式
下面结合具体实施例对本发明作进一步描述,以下列举的仅是本发明的具体实施例,但本发明的保护范围并不仅限于此。
实施例1玫瑰茄花色苷的制备
(1)将500g干燥的玫瑰茄与70%乙醇溶液(含1.5%(v/v)盐酸)按照料液比1g:8mL混合后搅拌24h(避光,37℃),三层纱布过滤,滤液以4000r/min离心15min,取上清液,在45℃下真空旋转蒸发除去乙醇,得到花色苷粗提液Ⅰ;
(2)按花色苷粗提液Ⅰ:乙酸乙酯体积比为1:1的比例加入乙酸乙酯萃取,静置分层,收集水相,重复萃取4次,收集并合并水相,40-45℃真空旋转蒸发除去残留的乙酸乙酯,得到花色苷粗提液Ⅱ;
(3)将所述花色苷粗提液Ⅱ注入活化后的AB-8大孔树脂中,先用5BV的去离子水以2.5BV/h的流速冲洗树脂,再分别使用5%和10%的乙醇溶液(含1.5%(v/v)盐酸)以2.5BV/h的流速梯度各洗脱5BV,收集10%的乙醇洗脱液,45℃下真空旋转蒸发除去乙醇,得到花色苷浸膏;
实施例1中的活化方法为:将乙醇浸泡12-48h后的大孔树脂装入层析柱中,用水洗至无醇味后,用2-6倍BV的4%HCl溶液,以3-5BV/h的流速通过树脂层,并浸泡3小时,而后用去离子水以同样流速洗至水洗液呈中性,用2-6倍柱体积4%的NaOH溶液,以3-5BV/h的流速通过树脂层并浸泡3小时,而后用去离子水以同样流速洗至水洗液呈中性。
(4)将所述浸膏用少量的去离子水溶解后,注入C18柱(C18Sep-Pak cartridge,Waters)中,先用8BV含1.5%甲酸去离子水冲洗柱体,然后用8BV的5%乙腈水溶液(含1.5%甲酸)洗脱,收集乙腈洗脱液,45℃下真空旋转蒸发,得到玫瑰茄花色苷浸膏,用少量去离子水溶解,之后冷冻干燥得到玫瑰茄花色苷冻干粉。经计算,500g干燥的玫瑰茄经上述步骤纯化后可得到60mg花色苷冻干粉。
实施例2玫瑰茄花色苷冻干粉组分鉴别
将实施例1中的花色苷冻干粉,配成1mg/mL的溶液,通过0.45μm膜过滤后,使用高效液相色谱检测,检测方法如下:流动相为A相(1.5%甲酸水溶液),B相(乙腈),梯度洗脱:95%-40%A相洗脱30min,进样量10μL,温度30℃,流速0.8mL/min,检测波长520nm。同时用飞燕草素-3-O-桑布双糖苷标准品进行定性和定量分析,结果显示,经上述方法制备得到的花色苷冻干粉飞燕草素-3-O-桑布双糖苷,其纯度达到96.2%;图1为实施例2中纯化后的飞燕草素-3-O-桑布双糖苷高效液相色谱图;图2为实施例2中飞燕草素-3-O-桑布双糖苷的化学结构式。
实施例3玫瑰茄花色苷的制备
(1)将500g干燥的玫瑰茄与70%乙醇溶液(含1.5%(v/v)盐酸)按照料液比1g:10mL混合后搅拌24h(避光,37℃),三层纱布过滤,滤液以4000r/min离心15min,取上清液,在45℃下真空旋转蒸发除去乙醇,得到花色苷粗提液Ⅰ;
(2)按花色苷粗提液Ⅰ:乙酸乙酯体积比为1:1的比例加入乙酸乙酯萃取,静置分层,收集水相,重复萃取6次,收集并合并水相,40-45℃真空旋转蒸发除去残留的乙酸乙酯,得到花色苷粗提液Ⅱ;
(3)将所述花色苷粗提液Ⅱ注入活化后的AB-8大孔树脂中,先用5BV的去离子水以2.5BV/h的流速冲洗树脂,再分别使用5%和10%的乙醇溶液(含1.5%(v/v)盐酸)以2.5BV/h的流速梯度各洗脱4BV,收集10%的乙醇洗脱液,45℃下真空旋转蒸发除去乙醇,得到花色苷浸膏;其中AB-8大孔树脂的活化方法与实施例1相同;
(4)将所述浸膏用少量的去离子水溶解后,注入C18柱(C18Sep-Pak cartridge,Waters)中,先用6BV含1.5%甲酸去离子水冲洗柱体,然后用5BV的5%乙腈水溶液(含1.5%甲酸)洗脱,收集乙腈洗脱液,45℃下真空旋转蒸发,得到玫瑰茄花色苷浸膏,用少量去离子水溶解,之后冷冻干燥得到玫瑰茄花色苷冻干粉。经计算,500g干燥的玫瑰茄经上述步骤纯化后可得到65mg的飞燕草素-3-O-桑布双糖苷,经实施例2的HPLC检测方法检测分析,其纯度达到95.7%。
实施例4玫瑰茄花色苷的制备
(1)将500g干燥的玫瑰茄与50%乙醇溶液(含1.5%(v/v)盐酸)按照料液比1g:6mL混合后搅拌24h(避光,37℃),三层纱布过滤,滤液以4000r/min离心15min,取上清液,在45℃下真空旋转蒸发除去乙醇,得到花色苷粗提液Ⅰ;
(2)按花色苷粗提液Ⅰ:乙酸乙酯体积比为1:1的比例加入乙酸乙酯萃取,静置分层,收集水相,重复萃取2次,收集并合并水相,40-45℃真空旋转蒸发除去残留的乙酸乙酯,得到花色苷粗提液Ⅱ;
(3)将所述花色苷粗提液Ⅱ注入活化后的AB-8大孔树脂中,先用5BV的去离子水以2.5BV/h的流速冲洗树脂,再分别使用5%和10%的乙醇溶液(含1.5%(v/v)盐酸)以2.5BV/h的流速梯度各洗脱5BV,收集10%的乙醇洗脱液,45℃下真空旋转蒸发除去乙醇,得到花色苷浸膏;其中AB-8大孔树脂的活化方法与实施例1相同;
(4)将所述浸膏用少量的去离子水溶解后,注入C18柱(C18Sep-Pak cartridge,Waters)中,先用10BV含1.5%甲酸去离子水冲洗柱体,然后用8BV的5%乙腈水溶液(含1.5%甲酸)洗脱,收集乙腈洗脱液,45℃下真空旋转蒸发,得到玫瑰茄花色苷浸膏,用少量去离子水溶解,之后冷冻干燥得到玫瑰茄花色苷冻干粉。经计算,500g干燥的玫瑰茄经上述步骤纯化后可得到49mg的飞燕草素-3-O-桑布双糖苷,经实施例2的HPLC检测方法检测分析,其纯度达到97.3%。
对本发明实施例1、实施例3和实施例4中步骤(3)中5%乙醇溶液(含1.5%(v/v)盐酸)的洗脱液进行收集和分析,发现5%乙醇溶液洗脱液中几乎无飞燕草素-3-O桑布双糖苷。
实施例5玫瑰茄花色苷的制备-高速逆流色谱法
(1)将500g干燥的玫瑰茄与70%乙醇溶液(含1.5%(v/v)盐酸)按照料液比1g:8mL混合后搅拌24h(避光,37℃),三层纱布过滤,滤液以4000r/min离心15min,取上清液,在45℃下真空旋转蒸发除去乙醇,得到花色苷粗提液Ⅰ;
(2)按花色苷粗提液Ⅰ:乙酸乙酯体积比为1:1的比例加入乙酸乙酯萃取,静置分层,收集水相,重复萃取4次,收集并合并水相,40-45℃真空旋转蒸发除去残留的乙酸乙酯,得到花色苷粗浸膏II;
(3)将所述花色苷粗提液Ⅱ注入活化后的AB-8大孔树脂中,先用5BV的去离子水以2.5BV/h的流速冲洗树脂,再分别使用5%和10%的乙醇溶液(含1.5%(v/v)盐酸)以2.5BV/h的流速梯度各洗脱5BV,收集10%的乙醇洗脱液,45℃下真空旋转蒸发除去乙醇,得到花色苷浸膏;其中AB-8大孔树脂的活化方法与实施例1相同;
(4)将所述的花色苷浸膏用高速逆流色谱法中的流动相溶解。高速逆流色谱法所采用的溶剂体系为,正丁醇:甲基叔丁基醚:乙腈:水=2:2:1:5,含0.1%的三氟乙酸。流速为3mL/min,转速900r/min,检测波长为280nm,收集第二个主峰(28min-35min),即飞燕草素-3-O-桑布双糖苷。45℃下真空旋转蒸发,得到花色苷浸膏,用少量去离子水溶解,之后冷冻干燥得到飞燕草素-3-O-桑布双糖苷冻干粉。经计算,500g的新鲜玫瑰茄经上述步骤纯化后可得到42mg的飞燕草素-3-O-桑布双糖苷,经实施例2的HPLC检测方法检测分析,其纯度达到96.8%。
图3为实施例5中飞燕草素-3-O-桑布双糖苷分离纯化的高速逆流色谱图;相比于实施例1,虽然高速逆流色谱也能制备得到的高纯度的飞燕草素-3-O-桑布双糖苷(收率和高纯度部分得益于本发明步骤(3)中AB-8大孔树脂的使用及酸性乙醇溶液的洗脱方法),但其得率较低,。此外,高速逆流色谱仪器价格昂贵,需使用大量的有机试剂,后处理复杂,因此本发明提供的方法能更简便的制备飞燕草素-3-O-桑布双糖苷,使之易于工业化生产。
实施例6飞燕草素-3-O-桑布双糖苷促进葡萄糖消耗实验
将HepG2细胞接种于6孔板,每孔约2×105个细胞。细胞培养24h后,加药(飞燕草素-3-O-桑布双糖苷浓度为10μg/mL、20μg/mL和40μg/mL;阳性对照为二甲双胍,终浓度为1mM;)不加药为空白对照。孵育24h后,吸取部分培养基用葡萄糖试剂盒(葡萄糖氧化酶-过氧化酶法)测定葡萄糖含量。葡萄糖消耗量计算按照南京建成生物工程研究所的葡萄糖试剂盒(货号:F006)说明书提供的公式计算。如图4结果显示,20μg/mL和40μg/mL浓度下,飞燕草素-3-O-桑布双糖苷能够促进HepG2细胞的葡萄糖消耗量,与对照组相比有显著性提升。
实施例7飞燕草素-3-O-桑布双糖苷促进糖原合成实验
将HepG2细胞接种于6孔板,每孔约2×105个细胞。细胞培养24h后,加药(飞燕草素-3-O-桑布双糖苷浓度为10μg/mL、20μg/mL和40μg/mL;阳性对照为二甲双胍,终浓度为1mM;)不加药为空白对照。孵育24h后,收集细胞并用PBS洗涤两次,用30%氢氧化钾匀浆后,将样品煮沸30分钟。随后加入1.5mL乙醇使糖原沉淀,然后以15000g离心5分钟。将所得沉淀溶解在0.5mL蒸馏水中,加入用浓硫酸稀释的0.2%蒽酮后煮沸20分钟。在620nm检测吸光值,使用外标法定量。糖原含量值采用葡萄糖当量表示。如图5实验结果表明,20μg/mL和40μg/mL浓度下,飞燕草素-3-O-桑布双糖苷能够促进HepG2细胞的糖原合成量,与对照组相比有显著性提升,并且促进效应强于阳性对照二甲双胍(1mM)。
Claims (9)
1.一种分离纯化飞燕草素-3-O桑布双糖苷的方法,其特征在于包括如下步骤:
1)将干燥的玫瑰茄与酸性乙醇溶液按照料液比1g:4mL~1g:10mL混合后避光搅拌12-24h,过滤,滤液离心取上清液,上清液在40-45℃下真空旋转蒸发除去乙醇,得到花色苷粗提液Ⅰ;
2)用乙酸乙酯对花色苷粗提液Ⅰ进行萃取,静置分层,收集水相,重复萃取2-6次,收集并合并水相,40-45℃真空旋转蒸发除去残留的乙酸乙酯,得到花色苷粗提液Ⅱ;
3)将所述花色苷粗提液Ⅱ用大孔树脂纯化,纯化的步骤为:将乙醇浸泡12-48h后的大孔树脂装入层析柱中,用水洗至无醇味后,再用HCl溶液和NaOH溶液进行活化,然后将玫瑰茄花色苷粗提物Ⅱ以0.5-1BV/h的流速注入大孔树脂,使得吸附花色苷的树脂的体积为树脂总体积的1/2至4/5,之后使用去离子水以5-8BV/h的流速淋洗树脂,再分别使用3-5BV的5%和10%的乙醇溶液以2-3BV/h的流速洗脱花色苷,收集10%的乙醇溶液洗脱液,40-45℃下真空旋转蒸发除去乙醇,得到花色苷浸膏;所述5%和10%的乙醇溶液中含有体积比为1.5%的盐酸;
4)将上述浸膏用少量去离子水溶解得到样品液,使用固相萃取柱纯化,纯化的步骤为将固相萃取柱使用甲醇活化,然后使用6-10BV去离子水清洗柱体至无甲醇残留,将样品液注入固相萃取柱中,用6-10BV的含1.5%甲酸的去离子水冲洗柱体,然后使用5-8BV的5%乙腈水溶液洗脱,所述乙腈水溶液中含1.5%甲酸,收集乙腈洗脱液,40-45℃下真空旋转蒸发,得到飞燕草素-3-O-桑布双糖苷浸膏,用少量去离子水溶解,之后冷冻干燥得到飞燕草素-3-O-桑布双糖苷粉末。
2.如权利要求1所述的一种分离纯化飞燕草素-3-O桑布双糖苷的方法,其特征在于所述步骤1)中的酸性乙醇溶液是体积百分比为50%-80%的乙醇溶液,乙醇溶液中含酸体积百分比为0.1%-2%,所述的酸为盐酸、甲酸或乙酸中的一种或多种。
3.如权利要求1所述的一种分离纯化飞燕草素-3-O桑布双糖苷的方法,其特征在于所述步骤1)中的过滤采用三层纱布过滤,滤液离心的方法为转速 4000r/min,离心时间为15min。
4.如权利要求1所述的一种分离纯化飞燕草素-3-O桑布双糖苷的方法,其特征在于所述步骤2)中的每次萃取过程中,乙酸乙酯与花色苷粗提液Ⅰ的体积比为1:1。
5.如权利要求1所述的一种分离纯化飞燕草素-3-O桑布双糖苷的方法,其特征在于所述大孔树脂为AB-8大孔树脂,比表面积为480-520m2/g,平均孔径为13-14nm,粒径范围在0.3-1.25mm。
6.如权利要求5所述的一种分离纯化飞燕草素-3-O桑布双糖苷的方法,其特征在于所述步骤3)用HCl溶液和NaOH溶液进行活化的具体步骤为:用2-6倍BV的4%HCl溶液,以3-5BV/h的流速通过树脂层,并浸泡3小时,而后用去离子水以同样流速洗至水洗液呈中性,用2-6倍柱体积4%的NaOH溶液,以3-5BV/h的流速通过树脂层并浸泡3小时,而后用去离子水以同样流速洗至水洗液呈中性。
7.如权利要求1所述的一种分离纯化飞燕草素-3-O桑布双糖苷的方法,其特征在于所述固相萃取柱为C18色谱柱。
8.如权利要求1所述的一种分离纯化飞燕草素-3-O桑布双糖苷的方法,其特征在于所述步骤4)样品液注入固相萃取柱的上样体积为柱体积的2/3。
9.权利要求1所述方法制备的飞燕草素-3-O-桑布双糖苷粉末在制备降糖功能食品或降糖药物中的应用。
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