Seven undescribed isopimarane diterpene glycosides hypoxylonoids A-G, along with five known analogues were obtained from the fungus Xylaria hypoxylon. The structures and absolute configurations of hypoxylonoids A-G were confirmed by extensive spectroscopic and single-crystal X-ray diffraction analyses. Among these compounds, the γ-lactone moiety formed between C-19 and C-6 of hypoxylonoid A; the 1,2-methyl shift of Me-18 of hypoxylonoids B and E; and the decarboxylation of C-19 of hypoxylonoid E, make them outstanding from the isopimarane family. Single crystal X-ray diffraction analyses of hypoxylonoids A, C, F, and 15-hydroxy-16-α-D-mannopyranosyloxyisopimar-7-en-19-oic acid was performed to determine their absolute structural configuration.
Xylariaceae, Isopimarane diterpene glycosides, X-ray diffraction analyses, Xylaria hypoxylon
NCBI PubMed ID: 33316595Publication DOI: 10.1016/j.phytochem.2020.112613Journal NLM ID: 0151434Publisher: Elsevier
Correspondence: C. Chen
; Y. Zhang
Institutions: Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, Tongji Medical College, Huazhong University of Science and Technology, Wuhan, 430030, Hubei Province, China, State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650204, Yunnan Province, China
Methods: 13C NMR, 1H NMR, NMR-2D, X-ray, TLC, GC, FTIR, HPLC, extraction, optical rotation measurement, fermentation, HR-ESI-MS, antibacterial assay, cytotoxicity assay, NO production, enzyme inhibition assay
Found