Aturanosides A and B, glycosylated anthraquinones with antiangiogenic activity from a soil-derived Streptomyces species.
Aturanosides A and B, glycosylated anthraquinones with antiangiogenic activity from a soil-derived Streptomyces species.
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Aturanosides A 和 B，糖基化蒽醌，具有抗血管生成活性，来自土壤来源的链霉菌属物种。
DOI：
10.1021/acs.jnatprod.8b00307
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发表时间：
2018
期刊：
影响因子：
5.1
通讯作者：
and Ahn J.S.
中科院分区：
文献类型：
--
作者：
Jang J.-P.;Hwang G.J.;Jang M.;Takahashi S.;Ko S.K.;Osada H.;Jang J.H.;and Ahn J.S.
土壤来源的链霉菌培养物提取物的化学研究。RK 88 -1441导致了两个新的糖基化蒽醌，aturanosides A（1）和B（2），以及一个新的蒽醌衍生物aturanocin（3）的分离和表征。通过详细的NMR和MS光谱分析确定了这些化合物的结构。根据偶合常数、ROESY相关性和化学衍生化的大小，确定1和2的糖单元的绝对构型分别为6-O-[N-乙酰基-α-d-氨基葡萄糖-（1→2）-α-l-鼠李糖苷]和6-O-α-l-鼠李糖苷。化合物1和2对人脐静脉内皮细胞（HUVECs）无细胞毒性，但显著抑制血管内皮生长因子（VEGF）诱导的血管形成和侵袭。VEGF受体2的磷酸化和血管内皮钙粘蛋白的表达在蛋白水平上也被观察到下调。
A chemical investigation of a culture extract from a soil-derivedStreptomycessp. RK88-1441 led to the isolation and characterization of two new glycosylated anthraquinones, aturanosides A (1) and B (2), and a new anthraquinone derivative, aturanocin (3). The structures of these compounds were elucidated by detailed NMR and MS spectroscopic analyses. The absolute configurations of the sugar units, based on the magnitudes of the coupling constants, ROESY correlations, and chemical derivatization, from1and2are 6-O-[N-acetyl-α-d-glucosamino-(1→2)-α-l-rhamnoside] and 6-O-α-l-rhamnoside, respectively. Compounds1and2showed no cytotoxicity against human umbilical vein endothelial cells (HUVECs), but significantly suppressed vascular endothelial growth factor (VEGF)-induced tube formation and invasion of HUVECs. The down-regulation of both the phosphorylation of VEGF receptor 2 and the expression of vascular endothelial cadherin at the protein level were also observed.