期刊
BIOORGANIC CHEMISTRY
卷 141, 期 -, 页码 -出版社
ACADEMIC PRESS INC ELSEVIER SCIENCE
DOI: 10.1016/j.bioorg.2023.106898
关键词
Isocoumarins; Phomopsis prunorum; Structural elucidation; Polyketide and shikimate pathways; Proangiogenic activity
In this study, seven novel isocoumarins, prunolactones A-G (1-7), with an unusual spiropentacyclic skeleton were isolated from the endophytic fungus Phomopsis prunorum. The structures and absolute configurations of these compounds were determined through spectroscopic analysis, X-ray diffraction, and ECD calculations. Additionally, three of these compounds showed significant in vivo proangiogenic activity in transgenic zebrafish.
Seven novel isocoumarins, prunolactones A-G (1-7), featuring an unusual 6/6/6/6/6 spiropentacyclic skeleton, together with two biosynthetic precursors phomopsilactone (8) and methyl 3-epi-shikimate (9), were isolated from the endophytic fungus Phomopsis prunorum guided by UPLC-QTOF-MS and 1H NMR spectroscopic analytical techniques. Their structures including absolute configurations of 1-7 were elucidated based on extensive spectroscopic data, X-ray diffraction analysis, and ECD calculations. Biogenetically, compounds 1-7 are proposed to be derived from polyketide and shikimate pathways via key intermolecular Diels - Alder reactions. Compounds 2, 3, and 7 showed significant in vivo proangiogenic activity in transgenic zebrafish.
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