Chlorinated polyketide obtained from a Daldinia sp. treated with the epigenetic modifier suberoylanilide hydroxamic acid.

Chlorinated polyketide obtained from a Daldinia sp. treated with the epigenetic modifier suberoylanilide hydroxamic acid.
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DOI:
10.1021/np500522z
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发表时间:
2014-11-26
影响因子:
5.1
通讯作者:
Cichewicz, Robert H.
Cichewicz, Robert H.
中科院分区:
生物学2区
文献类型:
--
作者:
Du, Lin;King, Jarrod B.;Cichewicz, Robert H.

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从Daldinia sp.中分离纯化出一种新的氯化五环聚酮类化合物达地酮E(1)。用表观遗传修饰剂Suberoylanilde异羟肟酸(SAHA)处理的真菌分离物。还从同一真菌中纯化了一种与生物合成相关的含有环氧化物的达地酮类似物2。两个化合物的结构都是通过波谱方法确定的,绝对构型是通过分析它们的核磁共振数据(耦合常数和ROESY关联)以及比旋光和电子捕获光谱的密度泛函计算确定的。在这些研究过程中,确定了代谢物2和以前报道的达地酮B具有相同的光谱数据,导致对报道的结构进行了修订。化合物1和2也显示了清除DPPH自由基的活性,其效力与阳性对照抗坏血酸相当。
A new chlorinated pentacyclic polyketide, daldinone E (1), was purified from a Daldinia sp. fungal isolate treated with the epigenetic modifier suberoylanilide hydroxamic acid (SAHA). A biosynthetically related epoxide-containing daldinone analogue, 2, was also purified from the same fungus. The structures of both compounds were established by spectroscopic methods, and the absolute configurations were assigned by analysis of their NMR data (coupling constants and ROESY correlations) and DFT calculations of specific rotations and ECD spectra. During the course of these studies it was determined that metabolite 2 and the previously reported daldinone B shared the same spectroscopic data, leading to a revision of the reported structure. Both compounds 1 and 2 also exhibited DPPH radical scavenging activities with potency comparable to the positive control ascorbic acid.
DOI: 10.1080/00021369.1975.10861598
发表时间: 1975-01-01
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