CN1129613C - 夹竹桃花多糖及其制备方法和应用 - Google Patents
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Abstract
一种具有神经生长因子作用的夹竹桃花多糖，夹竹桃花多糖是由夹竹桃花中提取分离再通过柱层析纯化制得。经实验证实夹竹桃花多糖对神经细胞有明显的促生长分化作用，对损伤的神经细胞有明显的修复功能，其作用或与神经生长因子相当或优于神经生长因子，因此夹竹桃花多糖可用于制备治疗老年痴呆症、中风、儿童智力低下等疾病的药物。
Description
本发明涉及多糖类及其作为药物的应用，尤其是涉及夹竹桃花多糖及其制备方法和应用。
诸如肝素之类的多糖在血液系统中具有抗凝血作用是较早被发现的，它已作为药物应用于临床。五十年代以后随着对糖功能认识的深入，逐步发现一定结构的多糖对机体的免疫系统有显著的作用：如抗肿瘤作用，抗病毒特别是抗爱滋病作用，抗炎作用和抗辐射作用。这些多糖已有三种作为药物在国内外临床上正式使用(非正式使用的还有数种)。当然还发现某些结构的多糖对消化道系统也有作用如抗呕吐，抗溃疡等(Kigohara H.Yamada H.Kitasato Arch Exp.Med.1991，64：167；方积年：多糖类药物，陈惠黎主编“糖复合物的结构与功能”上海医大出版社，1997，p325)。所有作为药物而应用于临床的多糖最大特点是毒副作用小。但是多糖对神经系统的作用至今还未见有人报道过。根据糖类的生物学特性的研究在1998年Thomas曾预言，多糖有可能作为治疗老年性痴呆的药物应用于临床(Thomas.WR，Current Opinion in Biotechnology，1998，9：74-79)。因此寻找一种具有类似于神经生长因子作用的多糖，是一个很有意义的工作。我们从分离到的30余种多糖中，筛选到一个来源于夹竹桃花中的多糖，发现它不但具有较强的免疫促进作用，而且还具有对神经细胞PC12的明显的促进繁殖与分化作用。
为此，本发明目的是提供一种具有神经生长因子作用的夹竹桃花多糖及其衍生物。
本发明另一目的是提供夹竹桃花多糖的制备方法，是由夹竹桃花中提取分离纯化而得。
本发明又一目的是提供夹竹桃花多糖用于制备治疗老年痴呆症，中风，儿童智力低下等疾病的药物的应用。
本发明夹竹桃花多糖是由夹竹桃花中提取分离获得的多糖。
由夹竹桃花多糖可制备得硫酸化夹竹桃花多糖和羧甲基化夹竹桃花多糖。
夹竹桃花多糖的制备方法：
夹竹桃花多糖是由夹竹桃花中提取分离获得，其步骤如下：
1、提取、分离：夹竹桃花经乙醇回流，脱脂后的干花，经沸水提取，过滤：(a)得滤液，滤液经浓缩，三倍乙醇沉淀，沉淀物溶于水，加十六烷基三甲基溴化物(CTAB) 沉淀，离心，上清液经透析，醇沉、干燥等步骤获得一多糖组份(NIF2)粗产物。沉淀物经醋酸溶解，醇沉，去蛋白等步骤，获另一多糖组份(NIF1)粗产物。(b)残渣经氢氧化钠溶液提取，再经透析、醇沉等步骤获另一多糖组份(NIF3)粗产物(详见图1)。
2、纯化：多糖组份NIF2经二乙氨乙基纤维素(DEAE-Cellulose)柱层析，水，0.2M NaCl，0.4M NaCl，4.0M NaCl展层，获得初步纯化的各多糖组份NIF2I，NIF2II，NIF2III，NIF2IV，上述四组份再经DEAE-Cellulose和/或聚丙烯酰胺葡聚糖(Sephacryl S-300)和/或葡聚糖凝胶G-200(Sephadex G-200)柱层析获得最后纯化的各多糖组份，分别命名为J7，J8，J6，J4，J5和J1(详见图2)。NIF1及NIF3也经二乙氨乙基-琼脂糖凝胶(DEAE-Sepharose)和/或Sephacryl S-300柱层析如NIF2的类似纯化过程，分别获得纯的多糖其他组份：J10，J3，J2和J9(详见图3和图4)。
各组份经常规方法如全水解，分子量测定，核磁共振，红外光谱等化学及光谱方法证明为多糖结构。
对上述纯化获得的10个夹竹桃花多糖组份进行纯度鉴定：以0.001ml/L的NaOH溶液为流动相，0.2ml/分的流速在KS-805多糖柱上进行纯度分析，测得各多糖组份J1-J10均为单一对称峰，说明所有组份均已达到单一纯品。
夹竹桃花多糖的分子量测定：以标准T-葡聚糖系列T-500，T-110，T-70，T-40，T-20为标准品，按纯度鉴定中所述条件进行HPLC，测得保留时间，以保留时间对已知标准分子量对数作图，得标准曲线然后进行夹竹桃花多糖样品，相同条件进行HPLC，测得保留时间，从标准曲线即可求得对应的分子量，分别为J1(分子量＞1×106)，J2(1.6×104)，J3(1.6×105)，J4(＞1×106)，J5(＞1×106)，J6(＞1×106)，J7(5.0×103)，J8(1.1×104)，J9(＞1×106)，J10(＞1×106)。
本发明夹竹桃花多糖衍生物的制备：
(1)硫酸化夹竹桃花多糖制备：取纯的夹竹桃花多糖在无水吡啶中，与氯磺酸反应，NaOH中和，透析，冻干即得硫酸化夹竹桃花多糖。
(2)羧甲基化夹竹桃花多糖的制备：取纯夹竹桃花多糖溶解于NaOH中，与氯乙酸反应，醋酸中和，透析、冻干，即得羧甲基化夹竹桃花多糖。
本发明夹竹桃花多糖经实验证实对神经细胞(PC-12细胞)有明显的促生长分化作用，对损伤的神经细胞有明显的促进修复功能。夹竹桃花多糖对PC-12细胞的作用主要表现在刺激细胞的伸长，带有活动的生长锥轴突样的神经轴突生长。由图5中可见，PC-12细胞置于不同浓度的夹竹桃花多糖溶液中，以神经生长因子(NGF)作阳性对照，均显示至少两倍于原细胞神经轴突的生长，夹竹桃花多糖在浓度为10μg/ml时即能诱导神经节伸展，由此证明其作用十分类似于NGF。实验结果显示其作用或与NGF相当或优于NGF。因此夹竹桃花多糖可用于制备治疗老年痴呆症，中风、儿童智力低下等疾病的药物。也可对抗H2O2等化学物质对神经细胞的损伤，对损伤细胞有明显的促进修复功能。夹竹桃花多糖还可用于实验中促神经细胞生长，分化及神经细胞损伤修复的阳性对照试剂。
本发明夹竹桃花多糖具有类似于NGF的作用，而NGF在动物体内含量少，分离纯化困难，而夹竹桃来源丰富，夹竹桃花多糖的分离纯化相对来说比较简单，便于生产。因此对神经系统具有生物活性的夹竹桃花多糖，具有重大的学术意义及应用前景。
本发明通过以下附图和实施例作进一步阐述，但并不限制本发明的内容。
附图说明：
图1由夹竹桃花提取分离获得夹竹桃花多糖的粗产物NIF1，NIF2及NIF3的流程图。
图2由夹竹桃花多糖粗产物NIF2纯化得多糖组份J1，J4，J5，J6，J7和J8流程图。
图3由夹竹桃花多糖粗产物NIF1纯化得多糖组份J10流程图。
图4由夹竹桃花多糖粗产物NIF3纯化得多糖组份J2，J3和J9流程图。
图5是夹竹桃花多糖组份J1，J2，J3，J4和J5对神经细胞PC-12的作用示意图。
实施例1：
夹竹桃花500g置于沙氏提取器中，用95％乙醇回流8小时，乙醇液弃去，夹竹桃花置于红外灯下去乙醇，得干花，然后用10升沸水提取8小时，过滤得滤液，滤液减压浓缩至1.5升，搅拌下加入4.5升95％之乙醇，得沉淀，沉淀经离心，弃去上清液。沉淀物溶于水1000ml，然后滴加5％浓度的十六烷基三甲基溴化铵(CTAB)300ml，离心得上清液及沉淀物，上清液经水透析，三倍乙醇沉淀，离心，真空干燥，得粗多糖NIF24.6g。沸水提取后的残渣，再用5％NaOH室温提取过夜，离心，上清液用盐酸调PH至7.0，透析，加入3倍乙醇沉淀，离心，真空干燥，得另一粗多糖NIF3 3.2g。用5％CTBA沉淀之沉淀物，溶于5％HOAC 500ml中，加入1500ml乙醇沉淀，离心得沉淀物，沉淀物溶于400ml水中，加入15％三氟乙酸(TCA)，离心去沉淀，上清液经透析，三倍乙醇沉淀、离心、真空干燥得另一粗多糖NIF12.2g。
实施例2：
NIF2 4.6g如图2所示，经DEAE-纤维素层析柱后，用水，0.2M NaCl，0.4M NaCl及4M NaCl相继展层，分部收集，取硫酸-苯酚法显色之阳性部份，各部份分别对蒸馏水透析2天，然后冷冻干燥，分别得到NIF2I0.83g，NIF2II 0.65g，NIF2III 0.94g及NIF2IV 0.76g。NIF2I再经DEAE-纤维素柱层析一次，水展层，取糖部份，透析，冷冻干燥得NIF2I A0.64g， NIF2I A再经DEAE-纤维素柱层析一次，经水展层，如前法透析，冷冻干燥得二个组份，J7 0.19g，J8 0.21g。NIF2II经Sephacryl S-300柱层析，0.2M NaCl展层，然后透析，冷冻干燥，得J6 0.32g。NIF2III经DEAE-纤维素柱层析，0.4M NaCl展层，透析，然后冷冻干燥得NIF2IIIB 0.234g，NIF2IIIC 0.518g。NIF2IIIB再经Sephadex G-200柱层析，水展层，透析，冷冻干燥得J4 0.18g。NIF2IIIC经Sephacryl S-300柱层析，0.2M NaCl展层，然后透析，冷冻干燥得J5 0.4g。NIF2IV经Sephacryl S-300柱层析，0.2M NaCl展层，然后透析，冷冻干燥得J1 0.35g。
实施例3
NIF1 2.2g溶于200ml水中，在搅拌中逐步加入100％的乙醇，使溶液的最终浓度为45％，离心，去上清液，得沉淀。溶解于水，经DEAE-Sepharose柱层析，0.4M NaCl展层，然后对蒸馏水透析2天，未透过液，冷冻干燥得NIF1E45 0.53g。然后再经Sephacryl S-300柱层析，0.2M NaCl展层，透析，冷冻干燥，得J10 0.2g。
实施例4
NIF3 3.2g溶于少量水中，然后DEAE-Sepharose柱层析，相继用水及0.4M NaCl展层，分别得NIF3I，NIF3III各1.2g及0.61g，NIF3I再经DEAE-Sepharose柱层析，水展层得NIF3IA，再一次DEAE-Sepharose柱层析，水展层得J3 0.16g，J2 0.42g。
NIF3III经Sephacryl S-300柱层析，0.2M NaCl洗脱，然后透析，冷冻干燥得J9 0.29g。
Claims (3)
1、一种制备夹竹桃花多糖的制备方法，其特征在于，是由夹竹桃花中提取分离夹竹桃花多糖，其步骤如下：
a.提取分离由夹竹桃花经乙醇脱脂，水提取后得到滤液和残渣：
所得残渣用NaOH提取处理，其上清液再经透析、醇沉、离心、真空干燥处理得到夹竹桃花多糖的一个组分NIF3粗产物；
所得滤液经浓缩，用三倍乙醇沉淀，弃去上清液，将所得沉淀物溶于水，加十六烷基三甲基溴化物沉淀，离心，所得上清液经透析、醇沉、离心、真空干燥处理后获得另一多糖组分NIF2粗产物；所得沉淀物经醋酸溶解，醇沉，去蛋白，获得另一多糖组分NIF1粗产物；
b.纯化将步骤a中的提取分离的三个夹竹桃花多糖的粗产物选用下列的层析柱：
先经二乙氨乙基-纤维素和/或二乙氨乙基-琼脂糖凝胶，再经聚丙烯酰胺葡聚糖S-300和/或葡聚糖凝胶G-200，进行2-3次层析提纯得到夹竹桃花多糖的纯产物。
2、一种由权利要求1所述的方法制备的夹竹桃花多糖。
3、如权利要求2所述的夹竹桃花多糖的应用，其特征在于，所述夹竹桃花多糖可用于制备治疗老年性痴呆症、中风或儿童智力低下疾病的药物。
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| CN100387703C (zh) * | 2003-06-11 | 2008-05-14 | 上海高科联合生物技术研发有限公司 | 多脂磷伞Pa-I·H菌株及培育多脂磷伞的方法和以其活性成分制成的药物 |
| CN101613414B (zh) * | 2008-06-26 | 2011-09-07 | 中国科学院上海药物研究所 | 两种夹竹桃寡糖及其制备方法和用途 |
| US10307450B2 (en) | 2010-01-11 | 2019-06-04 | Phoenix Biotechnology, Inc. | Method of treating neurological conditions with extract of Nerium species or Thevetia species |
| US9011937B2 (en) * | 2010-11-22 | 2015-04-21 | Phoenix Biotechnology, Inc. | Method of treating neurological conditions with extract of Nerium species or Thevetia species |
| US10383886B2 (en) | 2010-01-11 | 2019-08-20 | Phoenix Biotechnology, Inc. | Method of treating neurological conditions with oleandrin |
| KR101742852B1 (ko) * | 2010-11-22 | 2017-06-15 | 피닉스 바이오테크놀러지 인코포레이티드. | 네리움 종 또는 테베티아 종의 추출물로 신경학적 병태를 치료하는 방법 |
| US10702567B2 (en) | 2016-09-14 | 2020-07-07 | Phoenix Biotechnology, Inc. | Method and compositions for treating viral infection |
| US10729735B1 (en) | 2016-09-14 | 2020-08-04 | Phoenix Biotechnology, Inc. | Method and compostitions for treating coronavirus infection |
| US10596186B2 (en) | 2016-09-14 | 2020-03-24 | Phoenix Biotechnology, Inc. | Method and compositions for treating viral infections |
| US11331291B2 (en) | 2017-09-14 | 2022-05-17 | Phoenix Biotechnology, Inc. | Method of and improved composition for treating triterpene-responsive conditions, diseases or disorders |
| EP3681477A4 (en) | 2017-09-14 | 2021-06-09 | Phoenix Biotechnology, Inc. | PROCEDURES AND IMPROVED COMPOSITION FOR TREATMENT OF TREITERPEN RESPONSIBLE CONDITIONS, DISEASES, OR DISORDERS |
| US11806359B2 (en) | 2020-03-31 | 2023-11-07 | Phoenix Biotechnology, Inc. | Method and compositions for treating Coronavirus infection |
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| US4533548A (en) * | 1981-12-02 | 1985-08-06 | Kitasato Institute | Acidic polysaccharide CH-1 isolated from Chlorella pyrenoidosa and the use thereof |
| EP0246069A2 (en) * | 1986-05-13 | 1987-11-19 | Hüseyin Ziya Dr. Özel | Extracts of nerium species, methods of preparation, and use therefore |
| DE3915929A1 (de) * | 1989-05-16 | 1990-11-22 | Hueseyin Ziya Prof Dr Oezel | Polysaccharid mit immunstimulierender wirkung, verfahren zu dessen gewinnung und arzneimittel enthaltend dieses polysaccharid |
| EP0398313A2 (de) * | 1989-05-16 | 1990-11-22 | Hüseyin Ziya Dr. Özel | Polysaccharide mit immunstimulierender und antiproliferativer Wirkung, Verfahren zu ihrer Gewinnung und Arzneimittel enthaltend diese Substanzen |
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| US4533548A (en) * | 1981-12-02 | 1985-08-06 | Kitasato Institute | Acidic polysaccharide CH-1 isolated from Chlorella pyrenoidosa and the use thereof |
| EP0246069A2 (en) * | 1986-05-13 | 1987-11-19 | Hüseyin Ziya Dr. Özel | Extracts of nerium species, methods of preparation, and use therefore |
| DE3915929A1 (de) * | 1989-05-16 | 1990-11-22 | Hueseyin Ziya Prof Dr Oezel | Polysaccharid mit immunstimulierender wirkung, verfahren zu dessen gewinnung und arzneimittel enthaltend dieses polysaccharid |
| EP0398313A2 (de) * | 1989-05-16 | 1990-11-22 | Hüseyin Ziya Dr. Özel | Polysaccharide mit immunstimulierender und antiproliferativer Wirkung, Verfahren zu ihrer Gewinnung und Arzneimittel enthaltend diese Substanzen |
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