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Chemical-epigenetic method to enhance the chemodiversity of the marine algicolous fungus, Aspergillus terreus OUCMDZ-2739
Tetrahedron ( IF 2.1 ) Pub Date : 2017-11-20 , DOI: 10.1016/j.tet.2017.11.039
Kunlai Sun , Guoliang Zhu , Jiejie Hao , Yi Wang , Weiming Zhu

Four new meroterpenoids identified as (R)-4-((2,2-dimethylchroman-6-yl)methyl)-3-(4-hydroxyphenyl)-5-methoxyfuran-2(5H)-one (1), 1-(2,2-dimethylchroman-6-yl)-3-(4-hydroxyphenyl)propan-2-one (2), (R,E)-3-(2,2-dimethylchroman-6-yl)-4-hydroxy-5-((2-(2-hydroxypropan-2-yl)-2,3-dihydrobenzofuran-5-yl)methylene)furan-2(5H)-one (3), methyl (R)-2-(2-(2-hydroxypropan-2-yl)-2,3-dihydrobenzofuran-5-yl) acetate (4), along with nine known compounds (513) were isolated from a chemical-epigenetic culture of Aspergillus terreus OUCMDZ-2739 with 10 μM trichostatin A (TSA). Under the same condition without TSA, A. terreus OUCMDZ-2739 produced different compounds (1420), supporting that the chemical-epigenetic modification of fungi could enrich the chemodiversity of the fungal products. The cytotoxicity was observed for compound 8 against K562 cell, 9 against MCF-7 and K562 cells and 12 against MCF-7 cell with IC50 values of 9.5, 10.1, 13.0 and 8.5 μM, respectively. Compounds 3, 8 and 17 exhibited stronger α-glucosidase inhibition than 1-deoxynojirimycin and acarbose (positive controls) with IC50 values of 24.8, 1.2, 61.6, 191.7 and 555.1 μM, respectively. The enzyme kinetics study further indicated that compound 8 was an anticompetitive inhibitor with Ki value of 1.42 μM.



中文翻译:

化学表观遗传方法增强海洋藻类真菌曲霉曲霉OUCMDZ-2739的化学多样性

鉴定为(R)-4-((2,2-二甲基苯并吡喃-6-基)甲基)-3-(4-羟基苯基)-5-甲氧基呋喃-2(5 H)-的一个新的四类萜类化合物(1),1 -(2,2-二甲基苯并吡喃-6-基)-3-(4-羟基苯基)丙-2-一(2),(RE)-3-(2,2-二甲基苯并吡喃-6-基)-4 -羟基-5-((2-(2-羟基丙-2-基)-2,3-二氢苯并呋喃-5-基)亚甲基)呋喃-2(5 H)-一(3),甲基(R)-2 - (2-(2-羟基丙-2-基)-2,3-二氢苯并呋喃-5-基)乙酸甲酯(4),具有九个已知化合物(沿5 - 13)从一个化学-后生培养物中分离土曲霉OUCMDZ-2739与10  μ中号曲古抑菌素A(TSA)。下而不TSA相同条件下,土曲霉OUCMDZ-2739产生的不同的化合物(14 - 20),支持该真菌的化学-表观遗传修饰可以丰富真菌产品的chemodiversity。观察到的细胞毒性对化合物8对K562细胞,9针对MCF-7细胞和K562细胞和12针对与IC MCF-7细胞50倍的9.5的值,10.1,13.0和8.5  μ分别男,。化合物3817显示出更强的α葡萄糖苷酶抑制比IC 1-脱氧野尻霉素和阿卡波糖(阳性对照)50 24.8,1.2,61.6,191.7和555.1的值 μ分别男,。酶动力学研究进一步表明,化合物8是一个反竞争抑制剂ķ的1.42值 μ M.

更新日期:2017-11-20
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