Structures and absolute configurations of butenolide derivatives from the isopod-associated fungus Pidoplitchkoviella terricola. (January 2022)

• Record Type: Journal Article
• Authors: Zhai, Yi-Jie; Huo, Guang-Ming; Wei, Jing; Lin, Li-Bin; Zhang, Qiang; Li, Jian-Nan; Chen, Xin; Han, Wen-Bo; Gao, Jin-Ming
• Is Part Of: Phytochemistry. Volume 193(2022)
• Publication Date: 2022-01
• Subjects: Armadillidium vulgare (Latreille) -- Oniscidae -- Insect symbiont -- Pidoplitchkoviella terricola -- Xylariaceae -- Butenolides -- Altenusins -- Structure elucidation -- Tyrosinase inhibition; Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2021.112981
• Languages: English
• ISSNs: 0031-9422

Abstract

Abstract : 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. Graphical abstract: Seven undescribed butenolide derivatives, piterriones A–G were isolated from isopod-associated fungus Pidoplitchkoviella terricola . Dihydroaltenuene B exhibited mushroom tyrosinase inhibitory activity. Image 1 Highlights: Seven undescribed butenolide derivatives were isolated from the fungus Pidoplitchkoviella terricola. Their absolute configurations were determined by Mosher's method and microscale derivatization. This is the first report of the dihydroaltenuene B showing tyrosinase inhibitory activity.