白僵蚕活性成分分离纯化及其药理作用的研究
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摘要
白僵蚕是蚕蛾科家蚕幼虫感染病原白僵菌后致死的干燥菌虫体,作为中药材首载于《神农本草经》,是我国名贵的传统中药材,利用历史悠久。白僵蚕性平味咸、辛(《本经》),具有抗惊厥、抗凝、催眠、抑菌、抗癌、降糖、降脂等药理作用。临床上,白僵蚕使用单方或与其他中药配伍,主要用于外感发热、惊厥、癫痫、抽搐、头痛、偏头痛、面瘫、偏瘫、咳嗽、哮喘、剥脱性皮炎、皮肤瘙痒症、失眠、甲状腺瘤、糖尿病、荨麻疹、脑血栓形成、高血脂症等十几种疾病治疗。目前白僵蚕药用十分广泛,并常年出口外销。白僵蚕具有的众多药理作用,与其富含的功能活性成分直接相关。黄酮类化合物、白僵菌素、多糖作为白僵蚕的重要功能活性成分,其提取与检测、含量变化、组成与结构、药理作用及其机理等没有得到较深入研究。本论文对此进行了研究,主要结果如下：
1、利用CCD响应面方法对白僵蚕中黄酮类化合物的提取进行了优化,建立了白僵蚕粉过80目筛,以80%乙醇为提取溶剂,30：1的液料比,超声波处理20min,在100℃回流提取2.5h,为白僵蚕中黄酮类化合物的最佳提取方案。建立了分光光度法测定白僵蚕中黄酮类化合物的方法,该方法精密度、稳定性、重现性的标准差均在2%以内,回收率在95-105%范围内。利用建立的检测方法,查明了5龄起蚕感染白僵菌后12天内体内黄酮类化合物含量的变化规律。
2、利用HPLC-MS/MS方法,确定了白僵蚕体内白僵菌素含量的检测方法,测得白僵菌素含量为21.64μg/g,方法学检测最低检测限与最低定量限分别为4μg/g和12μg/g,重现性(RSD=1.16%)与3个水平的回收率(109±4.9%,97±3.8%,924±3.4%)均达到了较满意水平。利用建立的检测方法,查明了五龄起蚕感染白僵菌后12天内白僵菌素含量的变化情况。
3、采用阴离子交换层析(DEAE Sepharose F.F.)和凝胶柱层析(Sephacryl S系列材料),对白僵蚕多糖进行分离纯化。经DEAE Sepharose F.F.获得1个蒸馏水洗脱的中性多糖组分BBPW,3个不同浓度NaCl溶液洗脱的酸性多糖组分BBPS-1、BBPS-2、BBPS-3.进一步用Sephacryl S分离BBPW获得2个中性均一组分BBPW-1和BBPW-2,紫外扫描检测二者均不含蛋白质和核酸。红外光谱检测BBPW-2含有糖的特征吸收峰。高效液相色谱检测BBPW-1革BBPW-2为均一组分,BBPW-1分子量为3.67x106Da,是一种高度聚合的大分子多糖,BBPW-2的分子量为2.0×103Da,是一种寡聚糖。
4、对分离得到的均一组分BBPW-2进行了结构鉴定。利用单糖组成分析、甲基化分析、部分酸水解、核磁共振(NMR)技术(一维：1HNMR,13CMR,二维：1H-1H COSY谱、TOCSY谱、HMQC谱、NOESY谱和HMBC谱),对BBPW-2的单糖组成、糖残基个数、糖残基连接方式、构型、连接顺序等进行了研究。单糖组成分析结果显示,BBPW-2含有甘露糖、葡萄糖、半乳糖,比例为1：0.74：0.59；甲基化分析结果显示,BBPW-2含有的甘露糖、葡萄糖、半乳糖这三种单糖摩尔比为1：0.75：0.47,二者比例基本保持一致。甲基化分析结果同时表明,BBPW-2残基种类较多,结构比较复杂,其中甘露糖存在多种连接方式,主要为1位端基连接方式,其次为1,2,6-连接方式,还有少量的1,3-连接方式；葡萄糖主要为1,2,6-连接,还有少量的1位端基连接；半乳糖主要以1,2-连接。NMR分析结果显示,BBPW-2的结构是以β-D-1,2,6-葡萄糖和β-D-1,2,6-甘露糖为主链、以α-D-1,2-半乳糖和α-D-1,3-甘露糖为支链、α-D-甘露糖和β-D-葡萄糖为端基所组成寡聚糖,推断其结构如下：
5、考察了白僵蚕多糖对正常小鼠和环磷酰胺诱导的免疫抑制小鼠免疫功能的影响。发现白僵蚕多糖可提高小鼠的免疫器官重量、腹腔巨噬细胞吞噬功能、淋巴细胞转化率、血清中溶血素抗体水平和脾空斑形成细胞数量,结果表明白僵蚕多糖可从多方面增强正常小鼠和免疫抑制小鼠的免疫功能。
6、AB-8大孔树脂和聚酰胺树脂联用,以60%乙醇洗脱,对白僵蚕黄酮类化合物进行了制备,并考察了黄酮类化合物对人宫颈癌细胞Hela和人胚胎肾细胞HEK293增殖的影响。结果表明,白僵蚕黄酮类化合物对Hela细胞的增殖有明显抑制作用,对HEK293有促进增殖的作用。
7、考察了由超滤法分级得到的3个不同分子量多糖的体外抗癌作用。结果表明,按分子量分级法无法有效筛选出抗癌(Hela)明显却对正常细胞(HEK293)杀伤较小的组分。由阴离子交换柱分离到的4个多糖组分(包括1个中性多糖BBPW,3个酸性多糖BBPS-2、BBPS-2、BBPS-3)对人宫颈癌Hela细胞、人肝癌HepG2细胞有明显的抑制作用,其中中性多糖组分BBPW抑制作用最为明显,大于另外3个酸性多糖BBPS-1、BBPS-2、BBPS-3的抑制作用。另外考察了这4个多糖对小鼠巨噬细胞(RAW264.7)的影响,结果显示4个组分均能明显促进RAW264.7产生NO,并对其增殖有一定的促进作用。结果表明,白僵蚕多糖在体内的抗癌作用的发挥可能是通过增强吞噬细胞功能来实现的。
8、考察了从白僵蚕中性多糖组分BBPW分离出的两个均一组分BBPW-1和BBPW-2的抗癌作用,结果显示二者对Hela、HepG2抑制作用明显,其中大分子量的BBPW-1抑制作用稍微强于BBPW-2。另外还发现,BBPW-2对人乳腺癌细胞MCF-7有长期抑制作用。通过细胞凋亡和细胞周期检测表明,BBPW-2对Hela细胞的抑制作用是通过诱导细胞凋亡和将有丝分裂阻滞在G0/G1期和G2/M期来共同实现的。
Bombyx batryticatus, an oriental crude drug firstly recorded in "Shen Nong's Herbal Classic", is dried dead fungus-insect complex, which is dead and stiffened due to a Beauveria bassiana infection. As a valuable traditional Chinese medicinal material, it has been utilized for thousands of years. Bombyx batryticatus is salty and pungent, natured. It possesses muti-pharmacologic effects including anti-convulsion, anticoagulation, hypnogenesis, anti-fungus, anticancer and hypoglycemic and hypolipidemic effects. So it is widely used clinically alone or compatible with other drugs to treat exogenous fever, convulsion, epilepsy, headache, migraine, facial paralysis, hemiplegia, cough, asthma, exfoliative dermatitis, cutaneous pruritus, insomnia, thyroid adenoma, diabetes, urticaria, cerebral thrombosis, hyperlipidemia. With the deepening of research, Bomby batyaticatus's application is more and more widely. The active constituents play an important role in its pharmacological effects. And flavonoids, beauvericin and polysaccharide, as mainly active component parts, are very helpful to the effects especially in antioxidant, anticancer aspects. The present study focus on extraction, determination, separation and purification, structural identification, pharmacologic actions about the three active constituents. The mainly results are as follows:
1. Flavonoids was optimize-extracted by Central Composite Design of response surface methodology. The optimum program was like this:Bombyx batraticatus was extracted by80%ethanol after sifted with80item, pre-ultrasonic bath for20min,30:1liquid-to-solid ratio, for2.5h at100℃. The spectrophotometric method was established to determine flavonoids in Bombyx batraticatus, with qualified accuracy, stability and repeatability (RSD<2%) and recovery (95-105%). With the obtained optimum conditions, flavonoids content changes were investigated in silkworm body after infection of Beauveria bassiana within12days.
2. With HPLC-MS/MS, the determination method of beauverrion in Bombyx batraticatus was constructed. The results showed beauvericin's content was21.64μg/g. Methodology validation showed the LOD and LOQ were4μg/g and12μg/g. Repeatability (RSD=1.16%) and recoveries at3level (109±4.9%,97±3.8%,92±3.4%) were satisfied. Beauvericin content changes were investigated in silkworm body after infection of Beauveria bassiana within12days.
3. Polysaccharide of Bombyx batraticatus was separated and purified. The obtained crude polysaccharide was isolated and purified using DEAE Sepharose F. F. and gel-filtration chromatography (Sephacryl S-100-500) repeatedly. Two water-soluble homogeneous polysaccharides (BBPW-1, BBPW-2) were obtained. Lack of absorption at280nm and260nm by UV scanning indicated that they contained no protein and nucleic acid. IR spectra showed that the sugar characteristic groups were existed. HPLC producing a single symmetrical peak, indicated each of them was homogeneous and their molecular weight were3.67×106Da,2.0×103Da, respectively.
4. The structure of homogeneous BBPW-2was studied. Their structures were investigated using chemical (Sugar analysis, Methylation analysis, partial acid hydrolysis, etc.), and spectroscopic methods (ID NMR:'H NMR,13C NMR, DEPT spectra;2D NMR:'H-'H COSY, TOCSY, HMQC, NOESY and HMBC spectra; etc.) to confirm the sugar composition, the number of sugar residues, the form of glycosyl linkage, the configuration of anomeric center, the sequence of sugar residues.
Sugar analysis showed this polysaccharide was composed of mannose, glucose, and galactose in the ratio of1:0.74:0.59. Methylation analysis showed it contained2,6and1,3,6mannose linkage,1,6and terminal glucose linkage,1,6and2,6galactose linkage. Methylation analysis showed molar ration was1:0.75:0.47, which was accordance with the result of acetylation analysis. Methylation analysis showed BBPW-2contained1-,1,2,6-and1,3-mannose linkage,1,2,6-and1-glucose linkage and1,2-galactose linkage. NMR analysis further showed that its main chain was composed of (3-D-1,2,6linked glucosyl and (3-D-1,2,6linked mannosyl, side chain was composed of α-D-1,3mannose and α-1,2-D-galactose, and it also contains a minor terminal a-D-mannose and α-D-glucose. The structure was deducted as follows:
5. The effects of crude polysaccharide on immunologic function of normal mice and cyclophosphamide-induce immunosuppressed mice were investigated. It was found that polysaccharide of Bombyx batraticatus could improve immune organs' weight, phagocytic function of abdominal macrophage, lymphocyte transformation rate, hemolysin antibody's level in serum, the number of spleen plaque forming cells, which suggested that Bombyx batraticatus polysaccharide could promote mice immunologic function through many aspects.
6. Crude flavonoids was obtained by combination of AB-8marcoporous resin and amilan and elution with60%ethanol. Its effects on proliferation of cancer cells and normal cells were tested. The results showed that crude flavonoids could obviously suppress cancer cells' proliferation, and promote normal cells' proliferation.
7. Anticancer effect of three polysaccharides with different molecular weight were tested and it was found that they showed proliferation inhibition effect on both cancer cells and normal cells. Anticancer effect of four polysaccharides with different acidity obtained thought DEAE Sepharose F. F. were also tested and the result showed the anticancer effect of neutral polysaccharide eluted by water was more obvious than that of the other three acidic polysaccharides eluted by NaCl solution. All four polysaccharides could increase RAW264.7proliferation, and promote production of NO. Our results suggested that the anti-tumor activity could exert anti-tumor effects by increasing the production of NO by macrophages in vivo.
8. Anticancer effect of two homogeneous polysaccharides (BBPW-1, BBPW-2) separated from Bombyx batraticatus was studied and anticancer mechanism of BBPW-2with clear structure characteristics was implored. Results demonstrated both of two showed evident inhibition effect on cancer cells and the effect of BBPW-1with larger molecular weight was more significant. BBPW-2showed long-term anticancer effect on human breast cancer cells MCF-7. Through cell cycle analysis and apoptosis analysis, we found that the mechanisms of the growth inhibitory effect of BBPW-2on Hela cells is mediated through inducing cell apoptosis and cell-cycle arrest at G0/G1, G2/M phase.
1、利用CCD响应面方法对白僵蚕中黄酮类化合物的提取进行了优化,建立了白僵蚕粉过80目筛,以80%乙醇为提取溶剂,30：1的液料比,超声波处理20min,在100℃回流提取2.5h,为白僵蚕中黄酮类化合物的最佳提取方案。建立了分光光度法测定白僵蚕中黄酮类化合物的方法,该方法精密度、稳定性、重现性的标准差均在2%以内,回收率在95-105%范围内。利用建立的检测方法,查明了5龄起蚕感染白僵菌后12天内体内黄酮类化合物含量的变化规律。
2、利用HPLC-MS/MS方法,确定了白僵蚕体内白僵菌素含量的检测方法,测得白僵菌素含量为21.64μg/g,方法学检测最低检测限与最低定量限分别为4μg/g和12μg/g,重现性(RSD=1.16%)与3个水平的回收率(109±4.9%,97±3.8%,924±3.4%)均达到了较满意水平。利用建立的检测方法,查明了五龄起蚕感染白僵菌后12天内白僵菌素含量的变化情况。
3、采用阴离子交换层析(DEAE Sepharose F.F.)和凝胶柱层析(Sephacryl S系列材料),对白僵蚕多糖进行分离纯化。经DEAE Sepharose F.F.获得1个蒸馏水洗脱的中性多糖组分BBPW,3个不同浓度NaCl溶液洗脱的酸性多糖组分BBPS-1、BBPS-2、BBPS-3.进一步用Sephacryl S分离BBPW获得2个中性均一组分BBPW-1和BBPW-2,紫外扫描检测二者均不含蛋白质和核酸。红外光谱检测BBPW-2含有糖的特征吸收峰。高效液相色谱检测BBPW-1革BBPW-2为均一组分,BBPW-1分子量为3.67x106Da,是一种高度聚合的大分子多糖,BBPW-2的分子量为2.0×103Da,是一种寡聚糖。
4、对分离得到的均一组分BBPW-2进行了结构鉴定。利用单糖组成分析、甲基化分析、部分酸水解、核磁共振(NMR)技术(一维：1HNMR,13CMR,二维：1H-1H COSY谱、TOCSY谱、HMQC谱、NOESY谱和HMBC谱),对BBPW-2的单糖组成、糖残基个数、糖残基连接方式、构型、连接顺序等进行了研究。单糖组成分析结果显示,BBPW-2含有甘露糖、葡萄糖、半乳糖,比例为1：0.74：0.59；甲基化分析结果显示,BBPW-2含有的甘露糖、葡萄糖、半乳糖这三种单糖摩尔比为1：0.75：0.47,二者比例基本保持一致。甲基化分析结果同时表明,BBPW-2残基种类较多,结构比较复杂,其中甘露糖存在多种连接方式,主要为1位端基连接方式,其次为1,2,6-连接方式,还有少量的1,3-连接方式；葡萄糖主要为1,2,6-连接,还有少量的1位端基连接；半乳糖主要以1,2-连接。NMR分析结果显示,BBPW-2的结构是以β-D-1,2,6-葡萄糖和β-D-1,2,6-甘露糖为主链、以α-D-1,2-半乳糖和α-D-1,3-甘露糖为支链、α-D-甘露糖和β-D-葡萄糖为端基所组成寡聚糖,推断其结构如下：
5、考察了白僵蚕多糖对正常小鼠和环磷酰胺诱导的免疫抑制小鼠免疫功能的影响。发现白僵蚕多糖可提高小鼠的免疫器官重量、腹腔巨噬细胞吞噬功能、淋巴细胞转化率、血清中溶血素抗体水平和脾空斑形成细胞数量,结果表明白僵蚕多糖可从多方面增强正常小鼠和免疫抑制小鼠的免疫功能。
6、AB-8大孔树脂和聚酰胺树脂联用,以60%乙醇洗脱,对白僵蚕黄酮类化合物进行了制备,并考察了黄酮类化合物对人宫颈癌细胞Hela和人胚胎肾细胞HEK293增殖的影响。结果表明,白僵蚕黄酮类化合物对Hela细胞的增殖有明显抑制作用,对HEK293有促进增殖的作用。
7、考察了由超滤法分级得到的3个不同分子量多糖的体外抗癌作用。结果表明,按分子量分级法无法有效筛选出抗癌(Hela)明显却对正常细胞(HEK293)杀伤较小的组分。由阴离子交换柱分离到的4个多糖组分(包括1个中性多糖BBPW,3个酸性多糖BBPS-2、BBPS-2、BBPS-3)对人宫颈癌Hela细胞、人肝癌HepG2细胞有明显的抑制作用,其中中性多糖组分BBPW抑制作用最为明显,大于另外3个酸性多糖BBPS-1、BBPS-2、BBPS-3的抑制作用。另外考察了这4个多糖对小鼠巨噬细胞(RAW264.7)的影响,结果显示4个组分均能明显促进RAW264.7产生NO,并对其增殖有一定的促进作用。结果表明,白僵蚕多糖在体内的抗癌作用的发挥可能是通过增强吞噬细胞功能来实现的。
8、考察了从白僵蚕中性多糖组分BBPW分离出的两个均一组分BBPW-1和BBPW-2的抗癌作用,结果显示二者对Hela、HepG2抑制作用明显,其中大分子量的BBPW-1抑制作用稍微强于BBPW-2。另外还发现,BBPW-2对人乳腺癌细胞MCF-7有长期抑制作用。通过细胞凋亡和细胞周期检测表明,BBPW-2对Hela细胞的抑制作用是通过诱导细胞凋亡和将有丝分裂阻滞在G0/G1期和G2/M期来共同实现的。
Bombyx batryticatus, an oriental crude drug firstly recorded in "Shen Nong's Herbal Classic", is dried dead fungus-insect complex, which is dead and stiffened due to a Beauveria bassiana infection. As a valuable traditional Chinese medicinal material, it has been utilized for thousands of years. Bombyx batryticatus is salty and pungent, natured. It possesses muti-pharmacologic effects including anti-convulsion, anticoagulation, hypnogenesis, anti-fungus, anticancer and hypoglycemic and hypolipidemic effects. So it is widely used clinically alone or compatible with other drugs to treat exogenous fever, convulsion, epilepsy, headache, migraine, facial paralysis, hemiplegia, cough, asthma, exfoliative dermatitis, cutaneous pruritus, insomnia, thyroid adenoma, diabetes, urticaria, cerebral thrombosis, hyperlipidemia. With the deepening of research, Bomby batyaticatus's application is more and more widely. The active constituents play an important role in its pharmacological effects. And flavonoids, beauvericin and polysaccharide, as mainly active component parts, are very helpful to the effects especially in antioxidant, anticancer aspects. The present study focus on extraction, determination, separation and purification, structural identification, pharmacologic actions about the three active constituents. The mainly results are as follows:
1. Flavonoids was optimize-extracted by Central Composite Design of response surface methodology. The optimum program was like this:Bombyx batraticatus was extracted by80%ethanol after sifted with80item, pre-ultrasonic bath for20min,30:1liquid-to-solid ratio, for2.5h at100℃. The spectrophotometric method was established to determine flavonoids in Bombyx batraticatus, with qualified accuracy, stability and repeatability (RSD<2%) and recovery (95-105%). With the obtained optimum conditions, flavonoids content changes were investigated in silkworm body after infection of Beauveria bassiana within12days.
2. With HPLC-MS/MS, the determination method of beauverrion in Bombyx batraticatus was constructed. The results showed beauvericin's content was21.64μg/g. Methodology validation showed the LOD and LOQ were4μg/g and12μg/g. Repeatability (RSD=1.16%) and recoveries at3level (109±4.9%,97±3.8%,92±3.4%) were satisfied. Beauvericin content changes were investigated in silkworm body after infection of Beauveria bassiana within12days.
3. Polysaccharide of Bombyx batraticatus was separated and purified. The obtained crude polysaccharide was isolated and purified using DEAE Sepharose F. F. and gel-filtration chromatography (Sephacryl S-100-500) repeatedly. Two water-soluble homogeneous polysaccharides (BBPW-1, BBPW-2) were obtained. Lack of absorption at280nm and260nm by UV scanning indicated that they contained no protein and nucleic acid. IR spectra showed that the sugar characteristic groups were existed. HPLC producing a single symmetrical peak, indicated each of them was homogeneous and their molecular weight were3.67×106Da,2.0×103Da, respectively.
4. The structure of homogeneous BBPW-2was studied. Their structures were investigated using chemical (Sugar analysis, Methylation analysis, partial acid hydrolysis, etc.), and spectroscopic methods (ID NMR:'H NMR,13C NMR, DEPT spectra;2D NMR:'H-'H COSY, TOCSY, HMQC, NOESY and HMBC spectra; etc.) to confirm the sugar composition, the number of sugar residues, the form of glycosyl linkage, the configuration of anomeric center, the sequence of sugar residues.
Sugar analysis showed this polysaccharide was composed of mannose, glucose, and galactose in the ratio of1:0.74:0.59. Methylation analysis showed it contained2,6and1,3,6mannose linkage,1,6and terminal glucose linkage,1,6and2,6galactose linkage. Methylation analysis showed molar ration was1:0.75:0.47, which was accordance with the result of acetylation analysis. Methylation analysis showed BBPW-2contained1-,1,2,6-and1,3-mannose linkage,1,2,6-and1-glucose linkage and1,2-galactose linkage. NMR analysis further showed that its main chain was composed of (3-D-1,2,6linked glucosyl and (3-D-1,2,6linked mannosyl, side chain was composed of α-D-1,3mannose and α-1,2-D-galactose, and it also contains a minor terminal a-D-mannose and α-D-glucose. The structure was deducted as follows:
5. The effects of crude polysaccharide on immunologic function of normal mice and cyclophosphamide-induce immunosuppressed mice were investigated. It was found that polysaccharide of Bombyx batraticatus could improve immune organs' weight, phagocytic function of abdominal macrophage, lymphocyte transformation rate, hemolysin antibody's level in serum, the number of spleen plaque forming cells, which suggested that Bombyx batraticatus polysaccharide could promote mice immunologic function through many aspects.
6. Crude flavonoids was obtained by combination of AB-8marcoporous resin and amilan and elution with60%ethanol. Its effects on proliferation of cancer cells and normal cells were tested. The results showed that crude flavonoids could obviously suppress cancer cells' proliferation, and promote normal cells' proliferation.
7. Anticancer effect of three polysaccharides with different molecular weight were tested and it was found that they showed proliferation inhibition effect on both cancer cells and normal cells. Anticancer effect of four polysaccharides with different acidity obtained thought DEAE Sepharose F. F. were also tested and the result showed the anticancer effect of neutral polysaccharide eluted by water was more obvious than that of the other three acidic polysaccharides eluted by NaCl solution. All four polysaccharides could increase RAW264.7proliferation, and promote production of NO. Our results suggested that the anti-tumor activity could exert anti-tumor effects by increasing the production of NO by macrophages in vivo.
8. Anticancer effect of two homogeneous polysaccharides (BBPW-1, BBPW-2) separated from Bombyx batraticatus was studied and anticancer mechanism of BBPW-2with clear structure characteristics was implored. Results demonstrated both of two showed evident inhibition effect on cancer cells and the effect of BBPW-1with larger molecular weight was more significant. BBPW-2showed long-term anticancer effect on human breast cancer cells MCF-7. Through cell cycle analysis and apoptosis analysis, we found that the mechanisms of the growth inhibitory effect of BBPW-2on Hela cells is mediated through inducing cell apoptosis and cell-cycle arrest at G0/G1, G2/M phase.
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