Abstract
Four 10-membered ring resorcylic acid lactones (RALs) including a new compound hispidulactone F (1) and three known analogs hispidulactone B (2), 2 R, 4R-sonnerlactone (3), and 2 R, 4S-sonnerlactone (4) were isolated from the special bioenvironmental desert plant endophytic fungus Chaetosphaeronema hispidulum. The structure of the new compound hispidulactone F (1) was determined by extensive spectra analysis including HR-ESI-MS, NMR (1H, 13C, 1H-1H COSY, HSQC, and HMBC). Hispidulactone F (1) and hispidulactone B (2) were a pair of stereoisomers at C-3, whereas 2 R, 4R-sonnerlactone (3) and 2 R, 4S-sonnerlactone (4) were another pair of stereoisomers at C-4. The stereochemistries of the hydroxyl groups at C-3 in 1 and 2, and at C-4 in 3 and 4 were first determined by modified Mosher’s reactions. Thus, the absolute configuration C-3 in hispidulactone B (2) was not right in our previous report, and was rectified to be R. Compounds 1 and 4 were evaluated for their cytotoxic effects on the proliferation of HepG2. The possible biosynthetic pathway of compounds 1–4 was also presented.
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Acknowledgements
We acknowledge financial support from the National Key Research and Development Program of China “Research and Development of Comprehensive Technologies on Chemical Fertilizer and Pesticide Reduction and Synergism” (2017YFD0201402 for D. G), National Natural Science Foundation of China (31670011 for YGZ), the Special Project for Academic Construction of Peking Union Medical College (Tsinghua, 211-201920100902 for GD), the National Major Increase or Decrease Project-Construction of the Sustainable Utilization Capacity of Famous Traditional Chinese Medicine Resources (2060302 for JCQ).
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Stereochemical determination of four 10-membered ring Resorcylic acid lactones from the desert plant endophytic fungus Chaetosphaeronema hispidulum
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Zheng, M., Xu, ZL., Yang, RM. et al. Stereochemical determination of four 10-membered ring resorcylic acid lactones from the desert plant endophytic fungus Chaetosphaeronema hispidulum. J Antibiot 73, 471–474 (2020). https://doi.org/10.1038/s41429-020-0297-2
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DOI: https://doi.org/10.1038/s41429-020-0297-2