化学
青霉属
真菌
血管生成
二维核磁共振波谱
立体化学
藻类
质子核磁共振
核磁共振波谱
植物
生物
癌症研究
食品科学
作者
Shu-Rong Chen,Shih–Wei Wang,Ching‐Yeu Chen,Tzu-Yi Ke,Jue-Jun Lin,Tsong‐Long Hwang,Yi‐Ting Huang,Yu‐Ching Huang,Yao Cheng
标识
DOI:10.1246/bcsj.20220235
摘要
Sixteen azaphilone derivatives, including four new compounds, penicilazaphilones H and I (1 and 2), 11-epi-geumsanol F (3), and 11-epi-geumsanol B (4), together with twelve known analogues (5–16), were isolated from the algae-derived fungus Penicillium sclerotiorum purified from fresh marine macroalgae Grateloupia sp. The planar structures of 1–4 were identified by HRESIMS, IR, NMR, and UV spectroscopic analyses. Their absolute configurations were unambiguously determined by comparing the NMR and ECD spectra. These secondary metabolites were evaluated on the anti-angiogenic effect in human endothelial progenitor cells (EPCs). As a result, compounds 12, 14, and 16 exhibited anti-angiogenic activities by blocking cell growth, migration, and tube formation of EPCs. Additionally, the structure–activity relationships (SAR) for anti-angiogenic effects of isolated azaphilones were deduced. Four new (1–4) and twelve known (5–16) azaphilones were isolated from Penicillium sclerotiorum. All structures were identified by comprehensive spectroscopic analyses and comparing the NMR and ECD spectra. Isochromophilone IV (16) had a significant anti-angiogenic activity with an IC50 value of 19 ± 1 µM. The structure–activity relationships (SAR) of angiogenesis toward isolated azaphilones were discussed.
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