Pyranodipyran Derivatives with Tyrosyl DNA Phosphodiesterase 1 Inhibitory Activities and Fluorescent Properties from Aspergillus sp. EGF 15-0-3 |
| |
Authors: | Xia Wei Fang-Ting Wang Mei-Xia Si-Tu Hao Fan Jin-Shan Hu Hao Yang Shan-Yue Guan Lin-Kun An Cui-Xian Zhang |
| |
Institution: | 1.School of Pharmaceutical Sciences, Guangzhou University of Chinese Medicine, Guangzhou 510006, China; (X.W.); (M.-X.S.-T.); (H.F.); (J.-S.H.);2.School of Pharmaceutical Sciences, Sun Yat-Sen University, Guangzhou 510006, China; (F.-T.W.); (H.Y.);3.Instrumental Analysis & Research Center, Sun Yat-Sen University, Guangzhou 510275, China; |
| |
Abstract: | Four new benzodipyran racemates, namely (±)-aspergiletals A–D (3–6), representing a rare pyrano4,3-h]chromene scaffold were isolated together with eurotiumide G (1) and eurotiumide F (2) from the soft-coral-derived fungus Aspergillus sp. EGF 15-0-3. All the corresponding optically pure enantiomers were successfully separated by a chiral HPLC column. The structures and configurations of all the compounds were elucidated based on the combination of NMR and HRESIMS data, chiral separation, single-crystal X-ray diffraction, quantum chemical 13C NMR, and electronic circular dichroism calculations. Meanwhile, the structure of eurotiumide G was also revised. The TDP1 inhibitor activities and photophysical properties of the obtained compounds were evaluated. In the TDP1 inhibition assay, as a result of synergy between (+)-6 and (−)-6, (±)-6 displayed strong inhibitory activity to TDP1 with IC50 values of 6.50 ± 0.73 μM. All compounds had a large Stokes shift and could be utilized for elucidating the mode of bioactivities by fluorescence imaging. |
| |
Keywords: | soft-coral-derived fungus pyranodipyran derivatives tyrosyl DNA phosphodiesterase 1 inhibitory activities fluorescent properties |
|
|