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《Chinese Journal of Marine Drugs》 2013-03
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Metabolites of Aspergillus sp.16-02-1 isolated from a deep sea sediment and preliminary test of their antitumor and antifungal activities

CHEN Xiu-wen1,2,LI Chang-wei2,HUA Wei2,WU Chang-jing2,CUI Cheng-bin2*, Zhu Tian-jiao3,Gu Qian-qun3(1.College of Pharmacy,Guangxi Medical University,Nanning 530021,China; 2.Institute of Pharmacology and Toxicology,Academy of Military Medical Sciences, Beijing 100850,China;3.Key Laboratory of Marine Drugs,Ministry of Education,China; School of Medicine and Pharmacy,Ocean University of China,Qingdao 266003,China)  
Objective To investigate the metabolites of Aspergillus sp.16-02-1 isolated from a deep sea sediment and test their antitumor and antifungal activities.Methods Separating operations were performed in a bioassay-guided manner using various chromatographic means.Compounds isolated were identified on the basis of their physicochemical and spectroscopic data coupled with chemical reactions.Antitumor and antifungal activities were tested by MTT and paper-disc methods,respectively.Results Eight compounds 1-8 were isolated from the metabolites of Aspergillus sp.16-02-1 and identified as neoaspergillic acid(1),ferrineoaspergillin(2),methyl(2'S)-4-methoxy-3-(2'-methyl-3'-hydroxy)propionyloxy-benzoate(3),flavacol(4),cyclo-(trans-4-hydroxy-L-prolyl-L-leucine)(5),cyclo-(trans-4-hydroxyl-L-prolyl-L-phenylalanine)(6),uracil(7) and(11S)-neohydroxyaspergillic acid(8),respectively.Compounds 1-8 inhibited the growth of human cancer K562,HL-60,HeLa and BGC-823 cells to a certain extent and their inhibition rates on K562 cells ranged from 33.6% to 43.6% at 100 g mL-1.Compounds 1 and 8 also showed a weak antifungal activity on Candida albicans ATCC 10231 and Aspergillus terreus Thom var.terreus W-1.Conclusions Compounds 1~4 and 8 were obtained from the metabolites of fungi from deep sea samples,for the first time,among which 1 was the major metabolite of strain 16-02-1,with the yield of 28.8 mg/L.The 2'S for 3 and 11S for 8 absolute configurations,the 13C NMR data of 8 together with its 1H NMR data in DMSO-d6 and CD3OD,and the NMR evidence for the keto-enol tautomerism of 8 in DMSO-d6 were reported for the first time.The inhibitory effect of compounds 2-4 and 8 on several human cancer cell lines was also assayed for the first time.
【Fund】: 国家自然科学基金(81172976 30973631);; 国家高技术研究发展计划(2013AA092901);; 国家科技重大专项(2012ZX09301-003)资助
【CateGory Index】: R96
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