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A new pentaketide derivative, penilactonol A (<b>1</b>), and two new hydroxyphenylacetic acid derivatives, (2’<i>R</i>)-stachyline B (<b>2</b>) and (2’<i>R</i>)-westerdijkin A (<b>3</b>), together with five known metabolites, bisabolane-type sesquiterpenoids <b>4</b>–<b>6</b> and meroterpenoids <b>7</b> and <b>8</b>, were isolated from the solid culture of a marine alga-associated fungus <i>Penicillium chrysogenum</i> LD-201810. Their structures were elucidated based on extensive spectroscopic analyses, including 1D/2D NMR and high resolution electrospray ionization mass spectra (HRESIMS). The absolute configurations of the stereogenic carbons in <b>1</b> were determined by the (Mo₂(OAc)₄)-induced circular dichroism (CD) and comparison of the calculated and experimental electronic circular dichroism (ECD) spectra, while the absolute configuration of the stereogenic carbon in <b>2</b> was established using single-crystal X-ray diffraction analysis. Compounds <b>2</b> and <b>3</b> adapt the 2’<i>R</i>-configuration as compared to known hydroxyphenylacetic acid-derived and <i>O</i>-prenylated natural products. The cytotoxicity of <b>1</b>–<b>8</b> against human carcinoma cell lines (A549, BT-549, HeLa, HepG2, MCF-7, and THP-1) was evaluated. Compound <b>3</b> exhibited cytotoxicity to the HepG2 cell line with an IC₅₀ value of 22.0 μM. Furthermore, <b>5</b> showed considerable activities against A549 and THP-1 cell lines with IC₅₀ values of 21.2 and 18.2 μM, respectively.