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New Lanostane-Type Triterpenes with Anti-Inflammatory Activity from the Epidermis of Wolfiporia cocos

  • Te-Ri-Gen Bao
    Te-Ri-Gen Bao
    Teaching and Research Department of Chinese Materia Medica Resources, College of Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, People’s Republic of China
  • Guo-Qing Long
    Guo-Qing Long
    Teaching and Research Department of Chinese Materia Medica Resources, College of Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, People’s Republic of China
  • Yong Wang
    Yong Wang
    Teaching and Research Department of Chinese Materia Medica Resources, College of Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, People’s Republic of China
    More by Yong Wang
  • Qian Wang
    Qian Wang
    College of Pharmacy, Shenyang Pharmaceutical University, Shenyang 110016, People’s Republic of China
    More by Qian Wang
  • Xuan-Li Liu
    Xuan-Li Liu
    Teaching and Research Department of Chinese Materia Medica Resources, College of Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, People’s Republic of China
    More by Xuan-Li Liu
  • Gao-Sheng Hu
    Gao-Sheng Hu
    Teaching and Research Department of Chinese Materia Medica Resources, College of Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, People’s Republic of China
    More by Gao-Sheng Hu
  • Xiao-Xu Gao*
    Xiao-Xu Gao
    Teaching and Research Department of Chinese Materia Medica Resources, College of Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, People’s Republic of China
    *Email: [email protected]
    More by Xiao-Xu Gao
  • An-Hua Wang*
    An-Hua Wang
    Teaching and Research Department of Chinese Materia Medica Resources, College of Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, People’s Republic of China
    *Email: [email protected]
    More by An-Hua Wang
  • , and 
  • Jing-Ming Jia*
    Jing-Ming Jia
    Teaching and Research Department of Chinese Materia Medica Resources, College of Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, People’s Republic of China
    *Email: [email protected]
Cite this: J. Agric. Food Chem. 2022, 70, 14, 4418–4433
Publication Date (Web):March 29, 2022
https://doi.org/10.1021/acs.jafc.2c00823
Copyright © 2022 American Chemical Society

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    Abstract

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    A chemical study on the epidermis of cultivated edible mushroom Wolfiporia cocos resulted in the isolation and identification of 46 lanostane triterpenoids, containing 17 new compounds (117). An experimental determination of their anti-inflammatory activity showed that poricoic acid GM (39) most strongly inhibited NO production in LPS-induced RAW264.7 murine macrophages with an IC50 value at 9.73 μM. Furthermore, poricoic acid GM induced HO-1 protein expression and inhibited iNOS and COX2 protein expression as well as the release of PGE2, IL-1β, IL-6, TNF-α, and reactive oxygen species (ROS) in LPS-induced RAW264.7 cells. Mechanistically, poricoic acid GM suppressed the phosphorylation of the IκBα protein, which prevented NF-κB from entering the nucleus to lose transcriptional activity and inhibited the dissociation of Keap1 from Nrf2, thereby activating Nrf2 into the nucleus to regulate antioxidant genes. Furthermore, the MAPK signaling pathway may play a significant role in poricoic acid GM-induced elimination of inflammation. This work further confirms that lanostane triterpenoids are key ingredients responsible for the anti-inflammatory properties of the edible medicinal mushroom W. cocos.

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.jafc.2c00823.

    • Cell viability and NO production of the EtOH extract and solvent-partitioned fractions in RAW264.7 macrophages; experimental ECD and calculated ECD spectra of new compounds; the stack graph of compounds 15 and 161H NMR spectra; mRNA levels of iNOS, COX2, IL-1β, IL-6, TNF-α, etc., in LPS-stimulated RAW264.7 cells; and NMR spectra of 146 (PDF)

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    Cited By

    This article is cited by 1 publications.

    1. HtooTint Wai, Glenn C. Micalizio. Toward the Asymmetric de Novo Synthesis of Lanostanes: Construction of 7,11-Dideoxy-Δ5-lucidadone H. The Journal of Organic Chemistry 2022, 87 (21) , 14975-14979. https://doi.org/10.1021/acs.joc.2c02042

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