LC/MS-based chemical screening of fungal extract fraction library led to identification of three 2,3-aryl substituted furanone metabolites (1–3), including one known butenolide glycoside (1) whose stereochemistry remained unsolved and two new compounds gotjawaside and gotjawalide (2 and 3), from Auxarthron sp. KCB15F070, a fungus isolated from a soil sample of the volcanic island Jeju, Korea. Their planar structures were elucidated by 1D- and 2D-NMR spectroscopic and HRESIMS spectrometric techniques, and the absolute configurations of three compounds were solved using a combination of chemical derivatizations and computational analysis of vibrational circular dichroism (VCD) spectra.
secondary metabolites, ascomycetes, butenolide glycosides, vibrational circular dichroism
Publication DOI: 10.1016/j.tetlet.2019.151227Journal NLM ID: 2984819RPublisher: Elsevier
Correspondence: Jang J-H
; Ahn JS
Institutions: Graduate School of Pharmaceutical Sciences, The University of Tokyo, Tokyo, Japan, Anticancer Agent Research Center, Korea Research Institute of Bioscience and Biotechnology, Cheongju, South Korea, Department of Biomolecular Science, KRIBB School of Bioscience, Korea University of Science and Technology (UST), Daejeon, South Korea, Chemical Biology Research Group, RIKEN Center for Sustainable Resource Science (CSRS), Saitama, Japan, Advanced Elements Chemistry Laboratory, RIKEN, Cluster for Pioneering Research (CPR), Saitama, Japan, Korean Collection for Type Cultures, Korea Research Institute of Bioscience and Biotechnology, Jeongeup, South Korea, Natural Medicine Research Center, Korea Research Institute of Bioscience and Biotechnology, Cheongju, South Korea, RIKEN-KRIBB Joint Research Unit, RIKEN Center for Sustainable Resource Science (CSRS), Saitama, Japan
Methods: 13C NMR, 1H NMR, NMR-2D, IR, extraction, LC-MS, CC, HR-ESI-MS, antibacterial assay, cytotoxicity assay, derivatization, ECD, antifungal assay, VCD
Found