水母雪莲内生真菌Alterraria sp.的次级代谢产物鉴定
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摘要
目的:研究藏族药水母雪莲内生真菌Alterraria sp.的次级代谢产物。方法:从植物水母雪莲中分离得到内生菌Alterraria sp.,在考察培养条件后,对该菌种进行了扩大培养。运用反复硅胶柱色谱,LH-20凝胶柱色谱、开放ODS柱色谱、高效液相色谱等方法,并结合液质联用分析技术,对菌液的总萃取物进行分离纯化;并根据化合物的理化常数测定及光谱学(1D和2D NMR,MS等)数据分析鉴定所得化合物结构。结果:对水母雪莲中分离得到的内生真菌交链孢菌属Alterraria sp.进行次级代谢产物的研究,共得到9个化合物,分别鉴定为spirotryprostatin A(1),对羟基苯甲醛(2),4-羟基苯基-2’-羟基丙酯(3),二氢对甲氧基肉桂酸(4),4-甲氧基苯甲酸(5),对羟基苯乙酸甲酯(6),4-羟基苯乙醇(7),对羟基苯甲酸(8),3-苯基丙酸(9)。细胞毒测试结果表明,从TPXa中分离得到的化合物1对肺癌细胞株A549具有较强的增殖抑制活性,其IC50为2.0 mg·L-1。结论:以上化合物均为首次从交链孢菌属真菌中分离得到。
Objective: To study the secondary metabolites of an endophytic fungus Alterraria sp. isolated from Saussurea medusa. Method: Alterraria sp. was isolated from the medical plant S. medusa. The strain was cultured in a large-scale after the culture conditions had been optimized. The secondary metabolites were isolated by chromatography methods such as silica gel,Sephadex LH-20 columns,ODS flash column and HPLC,and the analysis of LC-MS. The structures of these compounds were identified by theirphysico-chemical constants and the NMR and MS data. Result: Nine compounds were isolated and identified as spirotryprostatin A( 1),4-hydroxybenzoic aldehyde( 2), 4-hydroxyphenyl-2'-hydroxypropanoate( 3), dihydro-p-methoxycinnamic acid( 4),4-methoxybenzoic acid( 5),p-hydroxymethylphenylacetate( 6),4-hydroxyphenyl ethanol( 7),4-hydroxybenzoic acid( 8),3-phenylpropanoic acid( 9). All compounds were tested for their inhibitory activities against human lung adenocarcinoma strain A-549. Compound 1 exhibited strong cytotoxic activity against A549 with IC50 value of 2. 0 mg·L- 1. Conclusion: All the compounds were isolated from Alterraria for the first time.
Objective: To study the secondary metabolites of an endophytic fungus Alterraria sp. isolated from Saussurea medusa. Method: Alterraria sp. was isolated from the medical plant S. medusa. The strain was cultured in a large-scale after the culture conditions had been optimized. The secondary metabolites were isolated by chromatography methods such as silica gel,Sephadex LH-20 columns,ODS flash column and HPLC,and the analysis of LC-MS. The structures of these compounds were identified by theirphysico-chemical constants and the NMR and MS data. Result: Nine compounds were isolated and identified as spirotryprostatin A( 1),4-hydroxybenzoic aldehyde( 2), 4-hydroxyphenyl-2'-hydroxypropanoate( 3), dihydro-p-methoxycinnamic acid( 4),4-methoxybenzoic acid( 5),p-hydroxymethylphenylacetate( 6),4-hydroxyphenyl ethanol( 7),4-hydroxybenzoic acid( 8),3-phenylpropanoic acid( 9). All compounds were tested for their inhibitory activities against human lung adenocarcinoma strain A-549. Compound 1 exhibited strong cytotoxic activity against A549 with IC50 value of 2. 0 mg·L- 1. Conclusion: All the compounds were isolated from Alterraria for the first time.
引文
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[2]李治滢,杨丽源,周斌,等.灯盏细辛内生真菌的研究Ⅰ:菌种分离及其分类鉴定[J].云南大学学报:自然科学版,2003,5(1):65-68.
[3]王利娟,杨小生,贺新生,等.银杏叶内生真菌抑菌菌株筛选[J].四川食品与培养,2007,43(4):34-36.
[4]项勇,崔京霞,吕安国,等.东北红豆杉内生真菌的分离和筛选[J].东北林业大学报,2002,30(2):30-34.
[5]CUI C B,Kakeya H,Osada H.Novel mammalian cell cycle inhibitors,spirotryprostatins A and B,produced by Aspergillus fumigatus,which inhibit mammalian cell cycle at G2/M phase I[J].Tetrahedron,1996,52(39):12651-12666.
[6]Kim H,Ralph J,LU F,et al.NMR analysis of lignins in CAD-deficient plants.Part 1.Incorporation of hydroxycinnamaldehydes and hydroxybenzaldehydes into lignins[J].Org Biomol Chem,2003,1(2):268-281.
[7]LU X,CHEN G,HUA H,DAI H,et al.Aromatic compounds from endophytic fungus Colletotrichum sp.L10 of Cephalotaxus hainanensis[J].Fitoterapia,2012,83(4):737-741.
[8]Takahashi T,Miyazawa M.Tyrosinase inhibitory activities of cinnamic acid analogues[J].Pharmazie,2010,65(2):913-918.
[9]Gouda Y G,Afaf M abdel-baky,Mdarwish F,et al.Phytochemical study of Jacaranda ovalifolia RBR family bignoniaceae culticated in Egypt[J].Bull Pharm Sci Assiut Univer,2002,25:165-174.
[10]李浩华,潘清灵,陈玉婵,等.深海真菌Penicillium herque FS83次生代谢产物研究[J].天然产物研究与开发,2016,28(3):327-330.
[11]Akaya Y,Furukawa T,Miura S,et al.Antioxidant constituents in distillation residue of awamori spirits[J].J Agric Food Chem,2007,55(1):75-79.
[12]李云秋,柴兴云,孙见凡,等.紫稍花化学成分研究[J].中药材,2010,33(1):60-61.
[13]Devi P,Wahidullah S,Rodrigues C,et al.The spongeassociated bacterium Bacillus licheniformis SAB1:a source of antimicrobial compounds[J].Mar Drugs,2010,8(4):1203-1212.