黑木耳多糖的分离制备及生物活性研究
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摘要
多糖具有抗肿瘤、降血糖、降血脂、调节免疫和抗氧化等生物活性,存在于动物、植物和微生物中。本文以黑木耳为原料,采用高速逆流色谱和柱层析方法,探索出一套完整的黑木耳多糖活性成分提取、分离、纯化的工艺,得到5种不同的黑木耳同多糖。同时对分离纯化的多糖进一步研究其生物活性,对肿瘤的抑制率、调节免疫能力、改变肿瘤细胞膜特性和抗氧化活性进行了研究,并探讨了其功能与结构之间的关系,以期为进一步开发利用黑木耳提供试验依据。
研究结果如下：
1.设计了三类不同的HSCCC双水相溶剂系统：PEG—磷酸盐系统、PEG—硫酸铵系统、PEG—Dextran—磷酸盐系统。应用正交试验方法根据HSCCC溶剂系统的分离条件,筛选得到了2种可用于HSCCC分离的溶剂系统：PEG1000:Dextran:K2HPO4:KH2PO4: H2O=8:3:20:30:120 (w/w)和PEG1000:K2HPO4:KH2PO4:H2O =0.5:1.25:1.25:7.0 (w/w)系统,本文选用PEG1000:K2HPO4: KH2PO4:H2O=0.5:1.25:1.25:7.0 (w/w)系统作为HSCCC的分离系统。
2.确定了HSCCC分离条件,转速700rpm,流速2.5mL/min,上样量2.0g,并从组分AAFRA中分离得到三种多糖AAPS1、AAPS2和AAPS3,质量分别为192mg、137mg、98mg。
3.组分AAFRB、AAFRC采用DEAE-cellulose、Sephacryl S-500HR柱层析进行分离纯化,得到了纯化后的AAFRB和AAFRC,所得量分别为120.5mg、92.7mg。4.采用HPGPC、PMP-HPLC、UPLC、1D NMR、2D NMR、GC-MS、FTIR等方法对得到的黑木耳多糖AAPS1、AAPS2、AAPS3、AAFRB和AAFRC的结构进行了研究。5种多糖均是由葡萄糖构成的同多糖,分子量分别为：1.62×105、2.59×105、4.83×105、9.30×105、1.20x 106Da,20℃时的比旋光度[α]D分别为：+89.30、+24.7°、+112.6°。+49.6°、+61.20；AAPS1是以(1→6)-a-D-吡喃葡萄糖和(1→3,6)-β-D-吡喃葡萄糖为主链,并在p-D-吡喃葡萄糖的O-3出现支链→4)-α-D-吡喃葡萄糖-(1→；AAPS1:
AAPS2是以(1→3)-p-吡啶葡萄糖残基和(1→3,6)-p-吡啶葡萄糖残基为主链,数量比为2：1,并在(1→3,6)-p-吡啶葡萄糖残基的O-6处有支链(1→)-p-吡啶葡萄糖残基；AAPS2:
AAPS3分子中存在→4-β-D-Glc-1→3-β-D-Glc-1→,→3-β-D-Glc-1→4-p-D-Glc-1→6-w3-D-Glc-1→片段,是以β-D-1,4-Glc,β-D-1,3-Glc和β-D-1,6-Glc残基构成主链的葡聚糖；AAPS3:
AAFRB是由→4)-α-D-Glcp-(1→、→3)-α-D-Glcp-(1→、→3,6)-α-D-Glcp-(1→、α-D-Glcp-(1→、→3)-β-D-Glcp-(1→残基构成,个数比为6：1：1：2：1,并在→3)-α-D-Glcp-(1→的O-6有支链α-D-Glcp-(1→吡啶葡萄糖残基；AAFRB:
AAFRC是→4)-α-D-Glcp-(1→、→3)-α-D-Glcp-(1→、α-D-Glcp-(1→、→4)-β-D-Glcp-(1→和→3)-β-D-Glcp-(1→片段构成,个数比为10：3：4：1：3,并在→3)-α-D-Glcp-(1→的O-6有支链α-D-Glcp-(1→吡啶葡萄糖残基的葡聚糖,AAFRC:
以上5种多糖化合物经查阅相关文献未见报道。
5.采用S180肉瘤小鼠模型研究了黑木耳多糖的抗肿瘤活性、对肿瘤细胞膜特性的影响和免疫学活性。结果表明5种多糖均具有一定的肿瘤抑制率,并且AAPS2和AAFRB能显著提高荷瘤小鼠的肝指数,AAFRB能显著提高胸腺指数；5种多糖均能促进细胞膜磷脂的降解,且与CT组间存在极显著差异(p<0.01),表现出较好的改变肿瘤细胞膜结构的特性；对细胞膜脂流动性(LFU)的研究发现,AAPS2、AAFRB、AAFRC能显著改变细胞膜脂的流动性(p<0.01)；免疫学特性来看,AAPS3、AAFRB多糖对促进脾淋巴细胞增殖有显著作用；除AAPS1的低剂量组外,多糖显示出能显著提高小鼠血清半数溶血值HC50,表明多糖可促进小鼠血清抗体的产生,且随着剂量的增高,增强作用呈现一定的相关性；采用对DPPH·、O2-·、·OH、N02-自由基清除能力和还原力研究发现,5种多糖显示出不同的抗氧化活性,AAPS2清除DPPH-自由基、O2-·自由基能力最强,AAFRC清除·OH自由基的能力最强,AAFRB的清除N02-的能力最强,还原力也最强。真菌多糖的结构对其作用机制也有着不同程度的影响,真菌多糖抗肿瘤的作用方式总体可以分为两类：第1类是以细胞毒为主的直接抗肿瘤方式；第2类是以调节机体免疫为主的间接抗肿瘤方式。通过以上对5种黑木耳多糖活性的研究可知,黑木耳多糖同时具有2种抗肿瘤的作用机制,促进肿瘤细胞的凋亡,并能显著调节免疫器官活性。从其结构分析,含有β构型的多糖活性一般表现出较高的活性,含有α构型的多糖一般只有较低的活性；并且多糖的活性还表现出与分子量有一定的关系,分子量范围在200—300kDa活性最高,同时多糖的糖苷键链接方式对活性也有一定的关系,多糖中含有1→3,1→6糖苷键通常表现出较高的活性,含有1→4糖苷键则活性不高。
Polysaccharides in animals and plants and microorganisms have various bioactivities, such as anti-tumor, reducing blood sugar and blood fat, adjusting immune function and antioxidationt. The present studies aim to extraction, separation and purification of polysaccharides from Auricularia polytricha by high speed countercurrent chromatography and column chromatography. Finally,5 purified polysaccharides were obtained, and their biological activities of tumor inhibition, immune regulation, and antioxidant activity were investigated. The main results are summarized as follows:
1. Two aqueous two-phase HSCCC solvent systems were established for the separation of polysaccharides from Auricularia polytricha, i.e. PEG 1000:Dextran:K2HPO4:KH2PO4:H2O=8:3:20:30:120 (w/w) and PEG1000:K2HPO4:KH2PO4:H2O=0.5:1.25:1.25:7.0 (w/w). The PEG1000:K2HPO4:KH2PO4:H2O=0.5:1.25:1.25:7.0 (w/w) was the best system by orthogonal test.
2. The HSCCC separation conditions were determined by experimental methods. The optimum operation condition is:column rotation speed,700rpm; flow rate of mobile phase,2.5mL/min; sample loading size,2.0g of the crude polysaccharides (AAFRA). The separation yielded three polysaccharides:AAPS1 (192 mg), AAPS2 (173 mg) and AAPS3 (98 mg).
3. Two polysaccharides AAFRB (120.5 mg) and AAFRC (92.7 mg) were obtained by DEAE-cellulose and Sephacryl S-500 HR column chromatography.
4. The structures of the five polysaccharides AAPS1, AAPS2, AAPS3, AAFRB and AAFRC were elucidated by using chromatographic (HPGPC, PMP-HPLC, UPLC) spectral (1D NMR,2D NMR, GC-MS and FTIR) and chemical methods. All the five polysaccharides are composed of glucose. The molecular weights of AAPS1, AAPS2, AAPS3, AAFRB and AAFRC are 1.62×105,2.59×105,4.83×105,9.30×105 and 1.20×106Da, respectively. The specific rotations [α]D in 20℃are+89.3°,+24.7°,+112.6°.+49.6°and +61.2°, orderly for AAPS1, AAPS2, AAPS3, AAFRB and AAFRC. The structures are as follows:
AAPS1:composed of a main chian (1→6)-a-D-glucopyranosyl, and (1→3,6)-β-D-glucopyranosyl and a side chain β-D-glucopyranosyloccurred O-3 of→4)-α-D-glucopyranosyl-(1→. AAPS1:
AAPS2:composed of a backbone (1→3)-linked-β-D-glucopyr-anosyl and (1→3,6)-linked-β-D-glucopyranosyl with a ratio of 2:1, and the single terminal (1→)-β-D-glucopyranosyl links to O-6 position of (1→3,6)-linked-p-D-glucopyranosyl along the main chain. AAPS2:
AAPS3:composed of residues→4-β-D-Glc-1→3-β-D-Glc-1→,→3-β-D-Glc-1→4-β-D-Glc-1→6-p-D-Glc-1→fragments andβ-D-1,4-Glc,β-D-1,3-Glc and p-D-1, and 6-Glc constitute the main chain. AAPS3:
AAFRB:composed of five residues:→4)-α-D-Glcp-(1→,→3)-α-D-Glcp-(1→,→3,6)-α-D-Glcp-(1→,α-D-Glcp-(1→,->3)-β-D-Glcp-(1→with a ratio of 6:1:1:2:1, and the O-6 of→3)-α-D-Glcp-(1→residueslinks to the branched chainα-D-Glcp-(1→; AAFRB:
AAFRC:composed of five residues→>4)-α-D-Glcp-(1→,→3)-α-D-Glcp-(1→,α-D-Glcp-(1→,→4)-β-D-Glcp-(1→and→3)-β-D-Glcp-(1→fragments, and the ratio is 10:3:4:1:3. The O-6 of→3)-α-D-Glcp-(1→links to the branched chainα-D-Glcp-(1→. AAFRC:
The above five polysaccharides have not been reported in any literatures.
5. The anti-tumor activity of the polysaccharides on the tumor cell membrane characteristics and immunological activity were studied by using S180 sarcoma mice. Among the five polysaccharides AAPS2 and AAFRB could significantly improve the liver index. Also AAFRB could significantly increase the thymus index. The five polysaccharides could promote the degradation of membrane phospholipids and showed better changes in tumor cell membrane structure characteristics. On the base of membrane lipid fluidity (LFU), AAPS2, AAFRB, AAFRC could significantly alter membrane fluidity (p<0.01) while AAPS3, AAFRB could significantly promote lymphocyte proliferation. The low dose group of AAPS1 showed a significantly increase of serum half of the hemolytic HC50, which indicated that the polysaccharide can promote serum antibody production with a correlation of dose-activity. The results of scavenging radicals DPPH-,02-·,·OH, NO2-·and reducing power showed that the five polysaccharide had different antioxidant activity. AAPS2 has a stronger activities of scavenging DPPH·radical, 02-·while AAFRC possessed a stronger activity of scavenging·OH radicals capacity and AAFRB has a stronger effect of removal N02 and reducing power. The structures of polysaccharides have directly effects on their mechanism of activities. The mechanism of anti-tumor activity can be divided into two kinds. The first is mainly a direct cytotoxicity against tumor cells; the second is indirect immunological regulation. The analysis of structure-activity relationship showed that polysaccharides withβconfiguration and the glycosidic bonds containing 1→3,1→6 have higher activity than those of a configuration, and the the molecular weight of the polysaccharides related to the activity. The polysaccharides with molecular weight range 200-300kDa showed the higher activity.
研究结果如下：
1.设计了三类不同的HSCCC双水相溶剂系统：PEG—磷酸盐系统、PEG—硫酸铵系统、PEG—Dextran—磷酸盐系统。应用正交试验方法根据HSCCC溶剂系统的分离条件,筛选得到了2种可用于HSCCC分离的溶剂系统：PEG1000:Dextran:K2HPO4:KH2PO4: H2O=8:3:20:30:120 (w/w)和PEG1000:K2HPO4:KH2PO4:H2O =0.5:1.25:1.25:7.0 (w/w)系统,本文选用PEG1000:K2HPO4: KH2PO4:H2O=0.5:1.25:1.25:7.0 (w/w)系统作为HSCCC的分离系统。
2.确定了HSCCC分离条件,转速700rpm,流速2.5mL/min,上样量2.0g,并从组分AAFRA中分离得到三种多糖AAPS1、AAPS2和AAPS3,质量分别为192mg、137mg、98mg。
3.组分AAFRB、AAFRC采用DEAE-cellulose、Sephacryl S-500HR柱层析进行分离纯化,得到了纯化后的AAFRB和AAFRC,所得量分别为120.5mg、92.7mg。4.采用HPGPC、PMP-HPLC、UPLC、1D NMR、2D NMR、GC-MS、FTIR等方法对得到的黑木耳多糖AAPS1、AAPS2、AAPS3、AAFRB和AAFRC的结构进行了研究。5种多糖均是由葡萄糖构成的同多糖,分子量分别为：1.62×105、2.59×105、4.83×105、9.30×105、1.20x 106Da,20℃时的比旋光度[α]D分别为：+89.30、+24.7°、+112.6°。+49.6°、+61.20；AAPS1是以(1→6)-a-D-吡喃葡萄糖和(1→3,6)-β-D-吡喃葡萄糖为主链,并在p-D-吡喃葡萄糖的O-3出现支链→4)-α-D-吡喃葡萄糖-(1→；AAPS1:
AAPS2是以(1→3)-p-吡啶葡萄糖残基和(1→3,6)-p-吡啶葡萄糖残基为主链,数量比为2：1,并在(1→3,6)-p-吡啶葡萄糖残基的O-6处有支链(1→)-p-吡啶葡萄糖残基；AAPS2:
AAPS3分子中存在→4-β-D-Glc-1→3-β-D-Glc-1→,→3-β-D-Glc-1→4-p-D-Glc-1→6-w3-D-Glc-1→片段,是以β-D-1,4-Glc,β-D-1,3-Glc和β-D-1,6-Glc残基构成主链的葡聚糖；AAPS3:
AAFRB是由→4)-α-D-Glcp-(1→、→3)-α-D-Glcp-(1→、→3,6)-α-D-Glcp-(1→、α-D-Glcp-(1→、→3)-β-D-Glcp-(1→残基构成,个数比为6：1：1：2：1,并在→3)-α-D-Glcp-(1→的O-6有支链α-D-Glcp-(1→吡啶葡萄糖残基；AAFRB:
AAFRC是→4)-α-D-Glcp-(1→、→3)-α-D-Glcp-(1→、α-D-Glcp-(1→、→4)-β-D-Glcp-(1→和→3)-β-D-Glcp-(1→片段构成,个数比为10：3：4：1：3,并在→3)-α-D-Glcp-(1→的O-6有支链α-D-Glcp-(1→吡啶葡萄糖残基的葡聚糖,AAFRC:
以上5种多糖化合物经查阅相关文献未见报道。
5.采用S180肉瘤小鼠模型研究了黑木耳多糖的抗肿瘤活性、对肿瘤细胞膜特性的影响和免疫学活性。结果表明5种多糖均具有一定的肿瘤抑制率,并且AAPS2和AAFRB能显著提高荷瘤小鼠的肝指数,AAFRB能显著提高胸腺指数；5种多糖均能促进细胞膜磷脂的降解,且与CT组间存在极显著差异(p<0.01),表现出较好的改变肿瘤细胞膜结构的特性；对细胞膜脂流动性(LFU)的研究发现,AAPS2、AAFRB、AAFRC能显著改变细胞膜脂的流动性(p<0.01)；免疫学特性来看,AAPS3、AAFRB多糖对促进脾淋巴细胞增殖有显著作用；除AAPS1的低剂量组外,多糖显示出能显著提高小鼠血清半数溶血值HC50,表明多糖可促进小鼠血清抗体的产生,且随着剂量的增高,增强作用呈现一定的相关性；采用对DPPH·、O2-·、·OH、N02-自由基清除能力和还原力研究发现,5种多糖显示出不同的抗氧化活性,AAPS2清除DPPH-自由基、O2-·自由基能力最强,AAFRC清除·OH自由基的能力最强,AAFRB的清除N02-的能力最强,还原力也最强。真菌多糖的结构对其作用机制也有着不同程度的影响,真菌多糖抗肿瘤的作用方式总体可以分为两类：第1类是以细胞毒为主的直接抗肿瘤方式；第2类是以调节机体免疫为主的间接抗肿瘤方式。通过以上对5种黑木耳多糖活性的研究可知,黑木耳多糖同时具有2种抗肿瘤的作用机制,促进肿瘤细胞的凋亡,并能显著调节免疫器官活性。从其结构分析,含有β构型的多糖活性一般表现出较高的活性,含有α构型的多糖一般只有较低的活性；并且多糖的活性还表现出与分子量有一定的关系,分子量范围在200—300kDa活性最高,同时多糖的糖苷键链接方式对活性也有一定的关系,多糖中含有1→3,1→6糖苷键通常表现出较高的活性,含有1→4糖苷键则活性不高。
Polysaccharides in animals and plants and microorganisms have various bioactivities, such as anti-tumor, reducing blood sugar and blood fat, adjusting immune function and antioxidationt. The present studies aim to extraction, separation and purification of polysaccharides from Auricularia polytricha by high speed countercurrent chromatography and column chromatography. Finally,5 purified polysaccharides were obtained, and their biological activities of tumor inhibition, immune regulation, and antioxidant activity were investigated. The main results are summarized as follows:
1. Two aqueous two-phase HSCCC solvent systems were established for the separation of polysaccharides from Auricularia polytricha, i.e. PEG 1000:Dextran:K2HPO4:KH2PO4:H2O=8:3:20:30:120 (w/w) and PEG1000:K2HPO4:KH2PO4:H2O=0.5:1.25:1.25:7.0 (w/w). The PEG1000:K2HPO4:KH2PO4:H2O=0.5:1.25:1.25:7.0 (w/w) was the best system by orthogonal test.
2. The HSCCC separation conditions were determined by experimental methods. The optimum operation condition is:column rotation speed,700rpm; flow rate of mobile phase,2.5mL/min; sample loading size,2.0g of the crude polysaccharides (AAFRA). The separation yielded three polysaccharides:AAPS1 (192 mg), AAPS2 (173 mg) and AAPS3 (98 mg).
3. Two polysaccharides AAFRB (120.5 mg) and AAFRC (92.7 mg) were obtained by DEAE-cellulose and Sephacryl S-500 HR column chromatography.
4. The structures of the five polysaccharides AAPS1, AAPS2, AAPS3, AAFRB and AAFRC were elucidated by using chromatographic (HPGPC, PMP-HPLC, UPLC) spectral (1D NMR,2D NMR, GC-MS and FTIR) and chemical methods. All the five polysaccharides are composed of glucose. The molecular weights of AAPS1, AAPS2, AAPS3, AAFRB and AAFRC are 1.62×105,2.59×105,4.83×105,9.30×105 and 1.20×106Da, respectively. The specific rotations [α]D in 20℃are+89.3°,+24.7°,+112.6°.+49.6°and +61.2°, orderly for AAPS1, AAPS2, AAPS3, AAFRB and AAFRC. The structures are as follows:
AAPS1:composed of a main chian (1→6)-a-D-glucopyranosyl, and (1→3,6)-β-D-glucopyranosyl and a side chain β-D-glucopyranosyloccurred O-3 of→4)-α-D-glucopyranosyl-(1→. AAPS1:
AAPS2:composed of a backbone (1→3)-linked-β-D-glucopyr-anosyl and (1→3,6)-linked-β-D-glucopyranosyl with a ratio of 2:1, and the single terminal (1→)-β-D-glucopyranosyl links to O-6 position of (1→3,6)-linked-p-D-glucopyranosyl along the main chain. AAPS2:
AAPS3:composed of residues→4-β-D-Glc-1→3-β-D-Glc-1→,→3-β-D-Glc-1→4-β-D-Glc-1→6-p-D-Glc-1→fragments andβ-D-1,4-Glc,β-D-1,3-Glc and p-D-1, and 6-Glc constitute the main chain. AAPS3:
AAFRB:composed of five residues:→4)-α-D-Glcp-(1→,→3)-α-D-Glcp-(1→,→3,6)-α-D-Glcp-(1→,α-D-Glcp-(1→,->3)-β-D-Glcp-(1→with a ratio of 6:1:1:2:1, and the O-6 of→3)-α-D-Glcp-(1→residueslinks to the branched chainα-D-Glcp-(1→; AAFRB:
AAFRC:composed of five residues→>4)-α-D-Glcp-(1→,→3)-α-D-Glcp-(1→,α-D-Glcp-(1→,→4)-β-D-Glcp-(1→and→3)-β-D-Glcp-(1→fragments, and the ratio is 10:3:4:1:3. The O-6 of→3)-α-D-Glcp-(1→links to the branched chainα-D-Glcp-(1→. AAFRC:
The above five polysaccharides have not been reported in any literatures.
5. The anti-tumor activity of the polysaccharides on the tumor cell membrane characteristics and immunological activity were studied by using S180 sarcoma mice. Among the five polysaccharides AAPS2 and AAFRB could significantly improve the liver index. Also AAFRB could significantly increase the thymus index. The five polysaccharides could promote the degradation of membrane phospholipids and showed better changes in tumor cell membrane structure characteristics. On the base of membrane lipid fluidity (LFU), AAPS2, AAFRB, AAFRC could significantly alter membrane fluidity (p<0.01) while AAPS3, AAFRB could significantly promote lymphocyte proliferation. The low dose group of AAPS1 showed a significantly increase of serum half of the hemolytic HC50, which indicated that the polysaccharide can promote serum antibody production with a correlation of dose-activity. The results of scavenging radicals DPPH-,02-·,·OH, NO2-·and reducing power showed that the five polysaccharide had different antioxidant activity. AAPS2 has a stronger activities of scavenging DPPH·radical, 02-·while AAFRC possessed a stronger activity of scavenging·OH radicals capacity and AAFRB has a stronger effect of removal N02 and reducing power. The structures of polysaccharides have directly effects on their mechanism of activities. The mechanism of anti-tumor activity can be divided into two kinds. The first is mainly a direct cytotoxicity against tumor cells; the second is indirect immunological regulation. The analysis of structure-activity relationship showed that polysaccharides withβconfiguration and the glycosidic bonds containing 1→3,1→6 have higher activity than those of a configuration, and the the molecular weight of the polysaccharides related to the activity. The polysaccharides with molecular weight range 200-300kDa showed the higher activity.
引文
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