2. Academic Validation
  3. Structures and absolute configurations of butenolide derivatives from the isopod-associated fungus Pidoplitchkoviella terricola

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

  • Phytochemistry. 2022 Jan;193:112981. doi: 10.1016/j.phytochem.2021.112981.
Yi-Jie Zhai 1,  Guang-Ming Huo 2,  Jing Wei 3,  Li-Bin Lin 1,  Qiang Zhang 1,  Jian-Nan Li 1,  Xin Chen 1,  Wen-Bo Han 4,  Jin-Ming Gao 5
Affiliations

Affiliations

  • 1 Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A&F University, 3 Taicheng Road, Yangling, 712100, Shaanxi, China.
  • 2 Institute of Medicinal Fungi, School of Food Science, Nanjing Xiaozhuang University, Nanjing, Jiangsu, 210017, People's Republic of China.
  • 3 College of Biology Pharmacy & Food Engineering, Shangluo University, Shangluo, 726000, Shaanxi, People's Republic of China.
  • 4 Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A&F University, 3 Taicheng Road, Yangling, 712100, Shaanxi, China. Electronic address: wbhan@nwafu.edu.cn.
  • 5 Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A&F University, 3 Taicheng Road, Yangling, 712100, Shaanxi, China. Electronic address: jinminggao@nwsuaf.edu.cn.
PMID: 34653910 DOI: 10.1016/j.phytochem.2021.112981
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.

Keywords

Altenusins; Armadillidium vulgare (Latreille); Butenolides; Insect symbiont; Oniscidae; Pidoplitchkoviella terricola; Structure elucidation; Tyrosinase inhibition; Xylariaceae.

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