海洋曲霉Aspergillus ruber TX-M4-1的次级代谢产物研究

Secondary metabolites from marine-derived Aspergillus ruber TX-M4-1

目的 对来自涠洲岛火山口的海洋曲霉Aspergillus ruber TX-M4-1的次级代谢产物进行研究。方法 利用硅胶、凝胶和高效液相等柱色谱方法进行分离纯化,运用紫外、红外、质谱和核磁共振波谱等分析方法对化合物进行结构鉴定,分别采用96孔板微量法、CCK-8法和DPPH法对化合物的抗菌活性、肿瘤细胞毒活性及抗氧化活性进行测试。结果 从海洋曲霉Aspergillus ruber TX-M4-1的发酵产物中分离鉴定了1个新的苯甲醛类化合物及10个已知结构的化合物,分别鉴定为5′-顺式-四氢金色灰绿曲霉素(1)、2-(1′,5′-庚二烯基)-3,6-二羟基-5-(3"-甲基-2"-丁烯基)苯甲醛(2)、异二氢金色灰绿曲霉素(3)、二氢金色灰绿曲霉素(4)、四氢金色灰绿曲霉素(5)、灰绿曲霉黄色素(6)、谷甾醇(7)、胆固醇(8)、链蠕孢素(9)、脱氢海胆灵(10)和新海胆灵A(11)。化合物1、5和6具有清除自由基活性,20μmol/L浓度下其DPPH自由基清除率分别为61.9%、88.0%和91.9%。结论 化合物1为新的苯甲醛类化合物。化合物1、5和6具有强的抗氧化活性。

Objective To study the secondary metabolites of marine-derived Aspergillus ruber TX-M4-1. Methods The secondary metabolites were isolated and purified by silica gel column chromatography, gel column chromatography and HPLC methods. The structures of the compounds were identified by UV, IR, MS and NMR. The antimicrobial, antitumor and antioxidant activities of compounds were evaluated by 96-well microtiter plate method, CCK-8 method and DPPH method, respectively. Results One new benzaldehyde compound and 10 compounds with known structures were isolated from the fermentation products of marine-derived Aspergillus ruber TX-M4-1. 5′-cis-isotetrahydroauroglaucin(1), 2-(1′,5′-heptadienyl)-3,6-dihydroxy-5-(3 "-methyl-2"-butenyl)benzaldehyde(2), isodihydroauroglaucin(3), dihydroauroglaucin(4), tetrahydroauroglaucin(5), flavoglaucin(6), β-sitosterol(7),cholesterol(8), catenarin(9), dehydroechinulin(10) and neoechinulin A(11), respectively. Compounds 1, 5 and 6 exhibited radical scavenging activity against DPPH with inhibition rates of 61.9%, 88.0% and 91.9% at a DPPH concentration of 20 μmol/L,respectively. Conclusion Compound 1 is a new benzaldehyde. Compounds 1, 5 and 6 exhibited strong antioxidant activity.