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Anti-inflammatory polyketides from the mangrove-derived fungus Ascomycota sp. SK2YWS-L
Tetrahedron ( IF 2.1 ) Pub Date : 2017-12-30 , DOI: 10.1016/j.tet.2017.12.057
Zhaoming Liu , Pei Qiu , Jing Li , Guangying Chen , Yan Chen , Hongju Liu , Zhigang She

A pair of novel 2,3-diaryl indone derivatives (+)- and (−)-ascomindone D [(+)-1 and (−)-1, respectively], as well as two new prenylated polyketides ascomfurans C (2) and ascomarugosin A (3) were obtained from the culture of a mangrove endophytic fungus Ascomycota sp. SK2YWS-L together with three known compounds (46). The enantiomers (+)-1 and (−)-1 were purified through chiral HPLC separation, which represented the first example of resolving 2,3-diaryl indone atropisomers in natural products. The structures of the new compounds were determined on the basis of interpretation of spectroscopic data including X-ray diffractions and the absolute configurations of (+)-1 and (−)-1 were elucidated by ECD calculations. The biosynthesis pathway was proposed. In the anti-inflammatory assay, (+)-1 and (−)-1 exhibited potential anti-inflammatory effects by inhibiting against the production of nitric oxide (NO) in lipopolysaccharide (LPS)-induced RAW 246.7 mouse macrophages with the IC50 values of 17.0 and 17.1 μM, respectively.



中文翻译:

来自红树林的真菌Ascomycota sp。的抗炎性聚酮化合物。SK2YWS-L

一对新的2,3-二芳基茚满衍生物(+)-和(-)-阿斯康辛酮D [(+)- 1和(-)- 1分别],以及两个新的烯丙基聚酮化合物ascomfurans C(2)从美洲红树内生真菌Ascomycota sp。的培养中获得了A.和Ascomarugosin A(3)。有三个已知化合物(SK2YWS-L一起4 - 6)。对映体(+)- 1和(-)- 1通过手性HPLC分离纯化产物,这是在天然产物中拆分2,3-二芳基茚酮阻转异构体的第一个实例。在解释包括X射线衍射在内的光谱数据的基础上确定了新化合物的结构,并通过ECD计算阐明了(+)- 1和(-)- 1的绝对构型。提出了生物合成途径。在抗炎试验中,(+)- 1和(-)- 1通过使用IC 50抑制脂多糖(LPS)诱导的RAW 246.7小鼠巨噬细胞中一氧化氮(NO)的产生而表现出潜在的抗炎作用。的17.0和17.1的值 μ分别男,。

更新日期:2017-12-30
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