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Five new 12-membered resorcylic acid lactone derivatives, penicimenolides A-E ( 1–5 ), one new ring-opened resorcylic acid lactone derivative penicimenolide F ( 6 ), and six known biogenetically related derivatives ( 7–12 ) were isolated from the culture broth of a strain of  Penicillium  sp. (NO. SYP-F-7919), a fungus obtained from the rhizosphere soil of  Panax notoginseng  collected from the Yunnan province of China. Their structures were elucidated by extensive NMR analyses, a modified Mosher’s method, chemical derivatization and single crystal X-ray diffraction analysis. Compounds  2–4  exhibited potent cytotoxicity against the U937 and MCF-7 tumour cell lines and showed moderate cytotoxic activity against the SH-SY5Y and SW480 tumour cell lines. The substitution of an acetyloxy or 2-hydroxypropionyloxy group at C-7 significantly increased the cytotoxic activity of the resorcylic acid lactone derivatives. Subsequently, the possible mechanism of compound  2  against MCF-7 cells was preliminarily investigated by  in silico  analysis and experimental validation, indicating compound  2  may act as a potential MEK/ERK inhibitor. Moreover, proteomics analysis was performed to explore compound  2 -regulated concrete mechanism underlying MEK/ERK pathway, which is still need further study in the future. In addition, compounds  2–4  and  7  exhibited a significant inhibitory effect on NO production induced by LPS.

Penicimenolides A-F, Resorcylic Acid Lactones from Penicillium sp., isolated from the Rhizosphere Soil of Panax notoginseng