Stereochemical determination of four 10-membered ring resorcylic acid lactones from the desert plant endophytic fungus Chaetosphaeronema hispidulum.

The Journal of Antibiotics
Min ZhengYong-Gang Zhang

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.

References

Feb 7, 2007·Chemical Communications : Chem Comm·Nicolas Winssinger, Sofia Barluenga
May 11, 2010·Bioorganic & Medicinal Chemistry Letters·Kai-Kai LiYong-Cheng Lin
Mar 20, 2013·Proceedings of the National Academy of Sciences of the United States of America·Yuquan XuIstván Molnár
Jan 7, 2015·European Journal of Medicinal Chemistry·Weiyun ShenJinyan Dong
Aug 11, 2018·Journal of Agricultural and Food Chemistry·Xiao-Yan ZhangGang Ding
Apr 13, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Luying LiGang Ding

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