CN109096056B - 红树林内生真菌来源的没药烷倍半萜类化合物及制备方法和在抗ii型糖尿病药物中的应用 - Google Patents
红树林内生真菌来源的没药烷倍半萜类化合物及制备方法和在抗ii型糖尿病药物中的应用 Download PDFInfo
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Abstract
本发明公开了红树林内生真菌来源的没药烷倍半萜类化合物及制备方法和在抗II型糖尿病药物中的应用。所述没药烷倍半萜类化合物的结构式如式（I）所示。化合物1和2能显著抑制α‑葡萄糖苷酶的活性，其IC50值分别为4.5μM，3.1μM，其中阳性对照阿卡波糖IC50为840.2μM。因此，该类化合物可用于开发α‑葡萄糖苷酶抑制剂药物，用于防治II型糖尿病。
Description
技术领域
本发明涉及药物化合物领域，具体涉及没药烷倍半萜类化合物在制备α-葡萄糖苷酶抑制剂药物中的应用。
背景技术
糖尿病是一种以高血糖，高血脂为特征的代谢性疾病，全球糖尿病地图(IDFDiabetes Atlas)显示2017年全球约4.25亿成人患糖尿病，是公认的世界性疾病。根据发病机制不同，一般分为I型糖尿病(胰岛素依赖型)和II型糖尿病(非胰岛素依赖型)。α-葡萄糖苷酶是一种水解酶，是治疗II型糖尿病的一个重要靶点，其功能是催化体内碳水化合物消化过程的最后一步，将低聚糖水解为单糖，进而导致了人体内血糖水平的提高。因此，抑制α-葡糖苷酶活性，阻止其将膳食淀粉转化为葡萄糖，降低和延迟餐后血糖水平是II型糖尿病的治疗策略。目前，临床上主要有阿卡波糖，米格列醇和伏格列波糖三种α-葡萄糖苷酶抑制剂，它们均来自天然产物。由于高昂的制备成本和不良的副作用限制了它们在临床上的应用，故设计或筛选出副作用少，易合成，成本低廉的α-葡萄糖苷酶抑制剂势在必行。
发明内容
本发明的目的是提供一种没药烷倍半萜类化合物在制备抗糖尿病药物中的应用。
本发明的技术方案如下：
本发明的化合物结构式如下：
本发明中的化合物1和2对α-葡萄糖苷酶具有抑制作用，可用于制备治疗II型糖尿病的药物。
具体实施方式
以下结合实施实例进一步解释本发明，但实施实例并不对本发明做任何形式的限定。
实施例1：
本发明的化合物1和2，是从红树林内生真菌黄曲霉Aspergillus flavusQQSG-3的发酵液中分离得到。红树林内生真菌黄曲霉Aspergillus flavusQQSG-3是从广东惠州红树植物Kandeliaobovata的树干中分离得到。所述红树林内生真菌黄曲霉AspergillusflavusQQSG-3菌株的保藏单位为广东省微生物菌种保藏中心，保藏地址为中国广东省微生物研究所，保藏号为GDMCC No:60380，保藏日期为2018年5月25日。具体步骤如下：
1.种子培养：
(1)配制种子培养基：称取马铃薯葡萄糖水72g，自来水1800mL，平均分装于6个500mL锥形瓶，121℃灭25分钟。
(2)种子的培养：将红树林内生真菌黄曲霉Aspergillus flavusQQSG-3接入种子培养基，在28℃的温度下，置摇床上以120rpm的转速，培养72小时得种子培养液。
2.发酵培养：
(1)配制发酵培养基：东北大米5000g，海盐9g，自来水3L，121℃灭25分钟。
(2)发酵培养：在超净台中将种子液10mL接入装有发酵培养基的锥形瓶中，于25℃静置培养30天。
3.提取分离：
发酵物用甲醇浸泡，浸泡液在48℃下减压浓缩得浸膏11.3g。该浸膏经硅胶柱层析进行分离，分别用10％，20％，30％，40％，50％，60％，70％，80％，100％的乙酸乙酯/石油醚梯度洗脱。其中30％的组分，采用葡聚糖凝胶Sephadex LH-20层析，用体积比为1:1的甲醇-氯仿为洗脱剂进行洗脱，再用硅胶柱层析，1:100的甲醇-氯仿为洗脱剂，获得化合物1(1.4mg)；1:80的甲醇-氯仿为洗脱剂，获得化合物2(1.3mg)。
实施例2：
对实施例1中的化合物进行结构分析测试，得到以下理化性质数据：
化合物1：浅黄色油状，EI-MS(m/z)：339[M-H]-；HR-EI-MS(m/z)：339.19631[M-H]-(理论值339.19657)。
化合物2：浅黄色油状，EI-MS(m/z)：485[M-H]-；HR-EI-MS(m/z)：485.32715[M-H]-(理论值485.32725)。
化合物1和2的NMR数据见表1和表2。
表1化合物1的NMR数据(125MHz/500MHz，TMS，ppm)
表2化合物2的NMR数据(125MHz/500MHz，TMS，ppm)
实施例3：
对实施例1中的化合物1和2进行α-葡萄糖苷酶抑制实验：
采用对硝基苯酚-α-葡萄糖苷(pNPG)为底物，在0.01M磷酸缓冲液(pH＝7.0)中进行。pNPG被α-葡萄糖苷酶酶解为对硝基苯酚，用紫外-可见分光光度计在405nm波长处测量其吸光度的变化而计算酶的活性。样品和阳性对照(阿卡波糖)均配成DMSO溶液(均为5000μM)，酶和底物用0.01M磷酸缓冲液分别配成0.2units/ml和5mM。
方法：在100μl反应体系中，依次加入60μl磷酸缓冲液，20μl葡萄糖苷酶溶液，10μl样品(DMSO)。在37℃下静置10min后，加入10μl基质，再在37℃下静置20min，立即在405nm波长处检测体系的吸光度。用如下公式来计算酶活性：抑制率(％)＝[(B–S)/B]×100％，其中B为加空白DMSO时的吸光度变化值，S为样品的吸光度变化值。测定5个浓度的样品，绘制浓度—抑制率曲线，得出其IC50值，平行测定三次。
结果测得化合物1和2能显著抑制α-葡萄糖苷酶的活性，其IC50分别为4.5μM及3.1μM，其中阳性对照阿卡波糖IC50为840.2μM。
Claims (3)
1.红树林内生真菌来源的没药烷倍半萜类化合物，其结构式如下所示：
2.权利要求1所述没药烷倍半萜类化合物在制备α-葡萄糖苷酶抑制剂中的应用。
3.根据权利要求2所述没药烷倍半萜类化合物的应用，其特征在于所述α-葡萄糖苷酶抑制剂用于防治II型糖尿病。
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
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| CN108191944A (zh) * | 2018-01-18 | 2018-06-22 | 华南师范大学 | 海洋微生物来源的二倍半萜AsperterpinolB衍生物及合成方法与糖酶应用 |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102584547A (zh) * | 2012-01-05 | 2012-07-18 | 中国海洋大学 | 一种没药烷倍半萜二聚体类化合物及其制备方法与应用 |
| CN108191944A (zh) * | 2018-01-18 | 2018-06-22 | 华南师范大学 | 海洋微生物来源的二倍半萜AsperterpinolB衍生物及合成方法与糖酶应用 |
Non-Patent Citations (4)
| Title |
|---|
| Antimicrobial Phenolic Bisabolanes and Related Derivatives from Penicillium aculeatum SD-321, a Deep Sea Sediment-Derived Fungus;Xiao-Dong Li等;《JOURNAL OF NATURAL PRODUCTS》;20150312;第844-849页 * |
| New bisabolane sesquiterpenoids from a marine-derived fungus Aspergillus sp. isolated from the sponge Xestospongia testudinaria;Ling-Ling Sun等;《Bioorganic & Medicinal Chemistry Letters》;20111223;第1326-1329页 * |
| New phenolic bisabolane sesquiterpenoid derivatives with cytotoxicity from Aspergillus tennesseensis;Li Liu等;《The Journal of Antibiotics》;20180207;第538-542页 * |
| Phenolic bisabolanes from the sponge-derived fungus Aspergillus sp.;Shuai Liu等;《Phytochemistry Letters》;20161018;第187-191页 * |
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