Fungus Aspergillus sp., which was isolated from soft coral Sarcophyton tortuosum, was cultured in the GPY medium containing glucose 10 g/L, peptone 5 g/L, yeast extract 2 g/L, sea water 1 L, at pH=7.5. Four com pounds...Fungus Aspergillus sp., which was isolated from soft coral Sarcophyton tortuosum, was cultured in the GPY medium containing glucose 10 g/L, peptone 5 g/L, yeast extract 2 g/L, sea water 1 L, at pH=7.5. Four com pounds, 3,6-diisobutyl-2（1H）-pyrazinone（1）, 3-isobutyl-6-（1-hydroxy-2-methylpropyl）-2（1H）-pyrazinone（2）, 3-methoxy-4-methyl-2,4-dien-pentanoic acid（3） and penicillic acid（4） were obtained from the AcOEt extract of the culture broth. Their structures were elucidated mainly based on the NMR, HR-EI-MS and X-ray single crystal diffraction experimental data. Compound 3 is a new compound. Compound 1 was previously proposed to be the tautomer of flavacol（3,6-diisobutylpyrazin-2-ol, 5）. However, the evaluation of the NMR and X-ray single crystal diffraction experimental data permitted us to propose that compound 1 existed as amide form instead oftautomers. Compound 1 is stable both in solution and crystal due to strong intermolecular hydrogen bonds. Incidentally supplying anthracenone to the GPY medium with a dose of 100 mg/L, the yield of penicillic acid（4） in the culture broth of the strain Aspergillus sp. was increased dramatically from 6 mg/L to 57 mg/L.展开更多
AIM:To explore the antimicrobial and anticancer activity of the fungi isolated from marine sediments of south India coastal belt.METHODS:Marine sediments were collected from different coastal locations of Kanyakumari ...AIM:To explore the antimicrobial and anticancer activity of the fungi isolated from marine sediments of south India coastal belt.METHODS:Marine sediments were collected from different coastal locations of Kanyakumari District,South India.Aseptically collected marine sediment samples were serially diluted and cultured using SDA media with seawater under appropriate culture conditions.Antimicrobial activity was confirmed by crowded plate techniques.Antimicrobial activity of marine fungi isolate was evaluated against six human pathogenic bacteria viz.,Enterobacter aerogenes.,Escherichia coli,Proteus mirabilis,Bacillus subtilis,Staphylococcus aureus,and Klebsiella pneumoniae.,with different solvents like n-butanol,chloroform,water and acetone.Anticancer activity of the selective fungal extracts was tested against Hep 2 cells using MTT assay.RESULTS:Fungus isolated from Muttom coast of south India showed activity against human pathogens.The fungi isolate Aspergillus protuberus SP1 was identified by partial sequence of large subunit ribosomal RNA(GenBank accession No.:HQ 386016).Different polar and non-polar solvent extracts of the marine-derived fungus isolate showed antibacterial activity towards various Gram-positive and Gram-negative human pathogens.The n-butanol extract of mycelium showed maximum inhibition.Based on antibacterial activity,the n-butanol extract was selected for anticancer test against Hep 2 cell line.The n-butanol extract was subjected to column chromatographic separation using different solvent compositions with ethanol:methanol(9:1) giving better sepeartion.The fraction was analyzed by GC-MS study showing the presence of nine compounds.CONCLUSION:These results are useful for further investigation of the fungus in the future.展开更多
目的阐明深海来源曲霉16-02-1的代谢产物及其抗肿瘤抗真菌活性。方法采用活性跟踪模式,利用多种色谱技术分离纯化代谢产物,结合化学反应的理化及波谱数据鉴定化合物。采用MTT法测试抗肿瘤活性,纸片法测试抗真菌活性。结果从曲霉16-02-1...目的阐明深海来源曲霉16-02-1的代谢产物及其抗肿瘤抗真菌活性。方法采用活性跟踪模式,利用多种色谱技术分离纯化代谢产物,结合化学反应的理化及波谱数据鉴定化合物。采用MTT法测试抗肿瘤活性,纸片法测试抗真菌活性。结果从曲霉16-02-1产物中分离鉴定了新曲霉酸(1)、ferrineoaspergillin(2)、(2'S)-4-甲氧基-3-(2'-甲基-3'-羟基)丙酰基-苯甲酸甲酯(3)、黄曲霉素(4)、环(反式-4-羟基-L-脯氨酸-L-亮氨酸)(5)、环(反式-4-羟基-L-脯氨酸-L-苯丙氨酸)(6)、尿嘧啶(7)和(11S)-新羟基曲霉酸(8)等8个化合物。化合物1～8对人癌细胞K562、HL-60、HeLa、BGC-823有一定抑制作用,在100μg.mL-1浓度下对K562细胞的抑制率在33.6%～43.6%之间,1和8还对白色念珠菌和土曲霉表现出较弱抑菌活性。结论首次从深海来源真菌产物中分离得到化合物1～4和8,其中1为曲霉16-02-1的主产物,发酵产率28.8mg/L。首次报道3的2'S和8的11S绝对构型、8的13 C NMR数据及其在DMSO-d6和CD3OD中的1 H NMR数据、以及8在DMSO-d6中酮式―烯醇式互变异构的NMR证据。化合物2～4和8对部分人癌细胞的抑制活性亦首次测试报道。展开更多
目的 对从混合培养的海洋软珊瑚共附生真菌中获得的结构新颖、活性良好的杂萜类成分进行研究。方法采用大米培养基对2株软珊瑚共附生曲霉属真菌EGF7-0-1和EGF15-0-3进行共培养;根据杂萜类化合物的结构特征,在基于质谱的分子网络(GNPS)...目的 对从混合培养的海洋软珊瑚共附生真菌中获得的结构新颖、活性良好的杂萜类成分进行研究。方法采用大米培养基对2株软珊瑚共附生曲霉属真菌EGF7-0-1和EGF15-0-3进行共培养;根据杂萜类化合物的结构特征,在基于质谱的分子网络(GNPS)和薄层色谱(TLC)的共同指导下,运用多种柱色谱及高效液相色谱(HPLC)等方法对其杂萜类成分进行目标导向分离;通过核磁共振(NMR)、高分辨质谱(HRMS)和旋光(ORD)等技术及物理常数对照等手段对单体化合物进行结构鉴定;采用液相色谱质谱联用(LC-MS^(n))和GNPS技术分析比较获得的杂萜类成分在2株真菌共培养及EGF7-0-1单培养中的含量。结果 从2株海洋真菌Aspergillus sp. EGF7-0-1和EGF15-0-3共培养的大米培养基中共分离得到7个杂萜类化合物,结构分别为terretonin (1)、terretonin A (2)、terretonin D1 (3)、terretonin H (4)、terreustoxin E (5)、aperterpene N (6)和asperterpene J (7)。LC-MSn和GNPS分析结果表明共培养条件下杂萜类化合物更为丰富。结论 化合物1~7均为具6/6/6骈并骨架的3,5-二甲基苔色酸(DMOA)途径衍生而成的杂萜。与菌株EGF7-0-1单培养相比,2株真菌共培养可以诱导产生丰富的杂萜,为进一步新颖杂萜类化合物的挖掘提供支持数据。展开更多
基金Supported by the National Natural Science Foundation of China(Nos.20502036 and 20602044)the Natural Science Founda-tion of Guangdong Province(No.05300667) the Fund for Innovative Chemical Experiment and Research of School of Chemi-stry and Chemical Engineering, Sun Yat-sen University, China
文摘Fungus Aspergillus sp., which was isolated from soft coral Sarcophyton tortuosum, was cultured in the GPY medium containing glucose 10 g/L, peptone 5 g/L, yeast extract 2 g/L, sea water 1 L, at pH=7.5. Four com pounds, 3,6-diisobutyl-2（1H）-pyrazinone（1）, 3-isobutyl-6-（1-hydroxy-2-methylpropyl）-2（1H）-pyrazinone（2）, 3-methoxy-4-methyl-2,4-dien-pentanoic acid（3） and penicillic acid（4） were obtained from the AcOEt extract of the culture broth. Their structures were elucidated mainly based on the NMR, HR-EI-MS and X-ray single crystal diffraction experimental data. Compound 3 is a new compound. Compound 1 was previously proposed to be the tautomer of flavacol（3,6-diisobutylpyrazin-2-ol, 5）. However, the evaluation of the NMR and X-ray single crystal diffraction experimental data permitted us to propose that compound 1 existed as amide form instead oftautomers. Compound 1 is stable both in solution and crystal due to strong intermolecular hydrogen bonds. Incidentally supplying anthracenone to the GPY medium with a dose of 100 mg/L, the yield of penicillic acid（4） in the culture broth of the strain Aspergillus sp. was increased dramatically from 6 mg/L to 57 mg/L.
文摘AIM:To explore the antimicrobial and anticancer activity of the fungi isolated from marine sediments of south India coastal belt.METHODS:Marine sediments were collected from different coastal locations of Kanyakumari District,South India.Aseptically collected marine sediment samples were serially diluted and cultured using SDA media with seawater under appropriate culture conditions.Antimicrobial activity was confirmed by crowded plate techniques.Antimicrobial activity of marine fungi isolate was evaluated against six human pathogenic bacteria viz.,Enterobacter aerogenes.,Escherichia coli,Proteus mirabilis,Bacillus subtilis,Staphylococcus aureus,and Klebsiella pneumoniae.,with different solvents like n-butanol,chloroform,water and acetone.Anticancer activity of the selective fungal extracts was tested against Hep 2 cells using MTT assay.RESULTS:Fungus isolated from Muttom coast of south India showed activity against human pathogens.The fungi isolate Aspergillus protuberus SP1 was identified by partial sequence of large subunit ribosomal RNA(GenBank accession No.:HQ 386016).Different polar and non-polar solvent extracts of the marine-derived fungus isolate showed antibacterial activity towards various Gram-positive and Gram-negative human pathogens.The n-butanol extract of mycelium showed maximum inhibition.Based on antibacterial activity,the n-butanol extract was selected for anticancer test against Hep 2 cell line.The n-butanol extract was subjected to column chromatographic separation using different solvent compositions with ethanol:methanol(9:1) giving better sepeartion.The fraction was analyzed by GC-MS study showing the presence of nine compounds.CONCLUSION:These results are useful for further investigation of the fungus in the future.
文摘目的阐明深海来源曲霉16-02-1的代谢产物及其抗肿瘤抗真菌活性。方法采用活性跟踪模式,利用多种色谱技术分离纯化代谢产物,结合化学反应的理化及波谱数据鉴定化合物。采用MTT法测试抗肿瘤活性,纸片法测试抗真菌活性。结果从曲霉16-02-1产物中分离鉴定了新曲霉酸(1)、ferrineoaspergillin(2)、(2'S)-4-甲氧基-3-(2'-甲基-3'-羟基)丙酰基-苯甲酸甲酯(3)、黄曲霉素(4)、环(反式-4-羟基-L-脯氨酸-L-亮氨酸)(5)、环(反式-4-羟基-L-脯氨酸-L-苯丙氨酸)(6)、尿嘧啶(7)和(11S)-新羟基曲霉酸(8)等8个化合物。化合物1～8对人癌细胞K562、HL-60、HeLa、BGC-823有一定抑制作用,在100μg.mL-1浓度下对K562细胞的抑制率在33.6%～43.6%之间,1和8还对白色念珠菌和土曲霉表现出较弱抑菌活性。结论首次从深海来源真菌产物中分离得到化合物1～4和8,其中1为曲霉16-02-1的主产物,发酵产率28.8mg/L。首次报道3的2'S和8的11S绝对构型、8的13 C NMR数据及其在DMSO-d6和CD3OD中的1 H NMR数据、以及8在DMSO-d6中酮式―烯醇式互变异构的NMR证据。化合物2～4和8对部分人癌细胞的抑制活性亦首次测试报道。
文摘目的 对从混合培养的海洋软珊瑚共附生真菌中获得的结构新颖、活性良好的杂萜类成分进行研究。方法采用大米培养基对2株软珊瑚共附生曲霉属真菌EGF7-0-1和EGF15-0-3进行共培养;根据杂萜类化合物的结构特征,在基于质谱的分子网络(GNPS)和薄层色谱(TLC)的共同指导下,运用多种柱色谱及高效液相色谱(HPLC)等方法对其杂萜类成分进行目标导向分离;通过核磁共振(NMR)、高分辨质谱(HRMS)和旋光(ORD)等技术及物理常数对照等手段对单体化合物进行结构鉴定;采用液相色谱质谱联用(LC-MS^(n))和GNPS技术分析比较获得的杂萜类成分在2株真菌共培养及EGF7-0-1单培养中的含量。结果 从2株海洋真菌Aspergillus sp. EGF7-0-1和EGF15-0-3共培养的大米培养基中共分离得到7个杂萜类化合物,结构分别为terretonin (1)、terretonin A (2)、terretonin D1 (3)、terretonin H (4)、terreustoxin E (5)、aperterpene N (6)和asperterpene J (7)。LC-MSn和GNPS分析结果表明共培养条件下杂萜类化合物更为丰富。结论 化合物1~7均为具6/6/6骈并骨架的3,5-二甲基苔色酸(DMOA)途径衍生而成的杂萜。与菌株EGF7-0-1单培养相比,2株真菌共培养可以诱导产生丰富的杂萜,为进一步新颖杂萜类化合物的挖掘提供支持数据。
