Chromatography

Derivatization

Stereochemistry

Tyrosinase

Organic chemistry

Absolute configuration

Enzyme

Butenolide

Kojic acid

Mass spectrometry

Chemistry

Phytochemistry

In this research, twenty aromatic and branched aliphatic polyketides, including seven previously undescribed butenolide derivatives, piterriones A-G and one known analogue, along with twelve known altenusin derivatives, were isolated from the isopod-associated fungus Pidoplitchkoviella terricola. Their structures were elucidated by analysis of NMR (1D and 2D) and mass spectrometry data, and their absolute configurations were determined by Mosher's method, microscale derivatization, and comparison of their specific rotations and ECD spectra. Dihydroaltenuene B exhibited mushroom tyrosinase inhibitory activity with an IC50 value of 38.33 ± 1.59 μM, which was comparable to that of the positive control, kojic acid (IC50 = 39.72 ± 1.34 μM). A molecular-docking study disclosed the hydrogen bonding interactions between the 3-OH and 4'-OH of dihydroaltenuene B and the His244, Met280 and Gly281 residues of tyrosinase.

Structures and absolute configurations of butenolide derivatives from the isopod-associated fungus Pidoplitchkoviella terricola