王衬,徐亚娟,黄小龙,等.来源于深海链霉菌Streptomyces sp. OUCMDZ-4112的吡咯生物碱[J].中国海洋药物,2016,35(1):1-9.
来源于深海链霉菌Streptomyces sp. OUCMDZ-4112的吡咯生物碱
Pyrrole alkaloids from the deep-sea sediment-derived Streptomyces sp. OUCMDZ-4112
投稿时间：2015-05-07  修订日期：2015-05-13
DOI：
中文关键词:  海洋放线菌  Streptomyces sp. OUCMDZ-4112  天然产物  灵菌红素  细胞毒活性  糖苷酶活性
English Keywords:marine actinobacteria  Streptomyces sp. OUCMDZ-4112  natural products  cytotoxicity  α-glucosidase inhibition
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作者单位E-mail
王衬 中国海洋大学海洋药物教育部重点实验室 932822668@qq.com 
徐亚娟 中国海洋大学海洋药物教育部重点实验室  
黄小龙 中国海洋大学海洋药物教育部重点实验室  
郝杰杰 中国海洋大学海洋药物教育部重点实验室  
朱伟明* 中国海洋大学海洋药物教育部重点实验室 weimingzhu@ouc.edu.cn 
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中文摘要:
      目的: 分离鉴定深海来源放线菌Streptomyces sp. OUCMDZ-4112的活性天然产物。方法：采用硅胶色谱,凝胶色谱及高效液相色谱(HPLC)等常规分离纯化手段对菌株的天然产物进行分离、纯化；运用核磁共振、CD、紫外、红外和旋光等方法鉴定所得化合物的结构；采用MTT法和CCK-8法评价化合物的细胞毒活性、对硝基苯基-α-吡喃葡萄糖苷(PNPG)法评价化合物的α-糖苷酶抑制活性。结果：从深海沉积物来源的链霉菌OUCMDZ-4112的发酵产物中分离鉴定了2个新的吡咯生物碱：S(+)-2-甲氧基-4-氧亚基-4-(2-吡咯基)丁酰胺(1)和R(–)-2-甲氧基-4-氧亚基-4-(2-吡咯基)丁酰胺(2)、以及2个已知的灵菌红素(PGs)：streptoriubin B (3) 和undecylprodigiosin (4)。化合物3和4对K562肿瘤细胞株具有强细胞毒活性,IC50分别为0.60 μmol/L和0.01 μmol/L(阿霉素的 IC50 为0.43 μmol/L)；同时外消旋1/2和化合物3、4具有α-糖苷酶抑制活性,IC50值分别为2.61、0.082和0.92 mmol/L(阿卡波糖的IC50为1.12 mmol/L)。结论：本文首次报道了PGs类化合物 3和 4的α-糖苷酶抑制活性；作为中间产物,新化合物1和 2的分离鉴定,证明了文献中PGs的生合成途径。
English Summary:
      Objective To identify the bioactive natural products of the deep-sea sediment-derived Streptomyces sp. OUCMDZ-4112. Methods The isolation and purification of compounds were performed by means of extraction, column chromatography over silica gel, Sephadex LH-20 and HPLC. And their structures were elucidated by analysis of NMR, MS, UV and CD along with ECD calculation. The cytotoxicity was evaluated by MTT and CCK-8 methods. And the α-glucosidase inhibition was assayed by p-nitrophenyl-α-D-glucopyranoside (PNPG) method. Results Two new pyrrole alkaloids, S( )-2-methoxy-4-oxo-4-(1H-pyrrol-2-yl)butanamide (1) and R(-)-2- methoxy-4-oxo-4-(1H-pyrrol-2-yl)butanamide (2), along with two known prodigiosins (PGs), streptoriubin B (3) and undecylprodigiosin (4) were isolated and identified from the fermentation broth of Streptomyces sp. OUCMDZ-4112. Compounds 3 and 4 showed potent cytotoxicities against K562 cell with the IC50 values of 0.60 μmol/L and 0.01 μmol/L, respectively (positive control, adriamycin, IC50 0.43 μmol/L). In addition, compound 4 and the racemic 1/2 exhibited pronounced α-glucosidase inhibition with the IC50 values of 0.92 and 2.61 mmol/L, respectively (positive control, acarbose, IC501.12 mmol/L). Conclusion The α-glucosidase inhibition of PGs 3 and 4 was reported here for the first time. And the isolation and identification of the new compounds 1 and 2 supported the biosynthesis of PGs in the literatures.
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