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海绵是具有代表性的海洋生物,其共附生微生物也是近年来研究的热点。在海洋高盐、高压、低温、寡营养的生存环境下,海绵共附生微生物能够产生结构新颖、生物活性良好的次级代谢产物。其中海绵共附生真菌是海绵化学多样性的重要来源[1]。
曲霉属 (Aspergillus sp)真菌分布广泛而且研究丰富。海洋曲霉属真菌的次级代谢产物主要包括聚酮类[2]、生物碱类[3]、肽类[4]、萜类[5]等化合物,具有抗肿瘤[6]、抗菌[7]、抗病毒[4]等生物活性。本课题的土曲霉(Aspergillus terreus)是从我国南海西沙永兴岛海域的棕色扁海绵Phakellia fusca中分离得到的,属于散囊菌目(Eurotiales)发菌科(Tri-chocomaceaez)的一种真菌,在海洋动植物和陆地植物中均有分布。该菌的次级代谢产物具有多样性,包括生物碱类化合物[8]、丁烯酸内酯类化合物[9]、萜类化合物[10]、环肽类化合物[11]等。本文采用硅胶柱色谱、Sephadex LH-20凝胶柱色谱、高效液相色谱等多种分离方法从土曲霉Aspergillus terreus中共分离得到8个单体化合物。通过理化常数测定、波谱数据分析等方法确定了化合物的结构。化合物1~8的结构见图1。
Study on chemical constituents of sponge-associated Aspergillus terreus
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摘要:
目的 对海绵共附生真菌土曲霉Aspergillus terreus中的化学成分进行研究。 方法 采用葡聚糖凝胶柱色谱、硅胶柱色谱和高效液相色谱等手段分离纯化;通过波谱数据鉴定化合物结构;采用PNPG法和DPPH法分别对分离得到的化合物进行α-葡萄糖苷酶抑制活性和抗氧化活性测试。 结果 从土曲霉Aspergillus terreus中分离得到8个化合物,分别鉴定为methyl-3,4,5-trimethoxy-2-(2-(nicotinamido) benzamido) benzoate ( 1 )、terrelumamide A ( 2 )、emeheterone ( 3 )、(8R,9S)-dihydroisoflavipucine ( 4 )、(8S,9S)-dihydroisoflavipucine ( 5 )、cyclo(S-Pro-S-Phe) ( 6 )、brevianamide F ( 7 )、terrein ( 8 )。活性测试结果表明,化合物 3 具有较强的α-葡萄糖苷酶的抑制活性,IC50值为14.28 µmol/L。 结论 化合物 3 、 4 、 5 、 7 为首次从土曲霉Aspergillus terreus中分离得到。 -
关键词:
- 土曲霉 /
- 化学成分 /
- α-葡萄糖苷酶抑制活性
Abstract:Objective To study the chemical constituents of Aspergillus terreus from sponge epiphytic fungal. Methods Sephadex LH-20 column chromatography, silica gel column chromatography and high performance liquid chroma-tography were used to separate and purify the compounds. The structures of compounds were identified by spectroscopic data. The α-glucosidase inhibitory activity and antioxidant activity of the compounds were tested by PNPG and DPPH methods, respectively. Results Eight compounds were isolated from Aspergillus terreus and identified as methyl-3,4,5-trimethoxy-2-(2-(nicotinamido) benzamido) benzoate ( 1 ), terrelumamide A ( 2) , emeheterone ( 3 ), (8R,9S)-dihydroisoflavipucine ( 4 ), (8S,9S)-dihydroisoflavipucine ( 5 ), cyclo(S-Pro-S-Phe) ( 6 ), brevianamide F ( 7 ), terrein ( 8 ). Compound 3 showed strong inhibitory activity against α-glucosidase and the IC50 value was 14.28 μmol/L. Conclusion Compounds 3 , 4 , 5 , and 7 were obtained from Aspergillus terreus for the first time. -
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