Beshanzoides A-D, unprecedented cycloheptanone-containing polyketides from P-4-1, an endophytic fungus of the endangered conifer .

Journal: RSC advances
Published Date: Dec 14, 2021

Abstract

A number of previously undescribed (1-7) and structurally related known (8-17) isobenzofuran-type polyketides were obtained from the fermentation of P-4-1, an endophytic fungus isolated from the fresh trunk bark of the critically endangered conifer . Beshanzoides A-D (1-4, resp.) feature a cycloheptanone-containing isobenzofuran ring system hitherto unknown, which might be biosynthesized two steps of aldol reactions starting from a common co-occurring isobenzofuran-type polyketide as the precursor. The new structures were elucidated by spectroscopic methods, electronic circular dichroism data, and single crystal X-ray diffraction analyses. Beshanzoide E (5) showed antimicrobial activity (MIC: 16 μg mL) against , whereas (±)-strobide A (10) inhibited (MIC: 16 μg mL) . Cyclopaldic acid (12) and 3--methyl-cyclopaldic acid (13) exhibited inhibitory effects against acetyl-CoA carboxylase 1 (ACC1) with IC values of 0.96 and 11.77 μM, respectively. Compound 12 also inhibited (IC: 7.56 μM) ATP-citrate lyase (ACL).

Authors

  • Hao-Wei Chen
    Department of Natural Medicine, School of Pharmacy, Fudan University Shanghai 201203 PR China jxiong@fudan.edu.cn jfhu@fudan.edu.cn.
  • Chun-Xiao Jiang
    Department of Natural Medicine, School of Pharmacy, Fudan University Shanghai 201203 PR China jxiong@fudan.edu.cn jfhu@fudan.edu.cn.
  • Jiyang Li
    Department of Natural Medicine, School of Pharmacy, Fudan University Shanghai 201203 PR China jxiong@fudan.edu.cn jfhu@fudan.edu.cn.
  • Na Li
    School of Nursing, Fujian University of Traditional Chinese Medicine, Fuzhou, China.
  • Yi Zang
    State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences Shanghai 201203 PR China.
  • Xi-Ying Wu
    Department of Natural Medicine, School of Pharmacy, Fudan University Shanghai 201203 PR China jxiong@fudan.edu.cn jfhu@fudan.edu.cn.
  • Wen-Xue Chen
    Department of Chemistry, Fudan University Shanghai 200438 PR China.
  • Juan Xiong
    Department of Natural Medicine, School of Pharmacy, Fudan University Shanghai 201203 PR China jxiong@fudan.edu.cn jfhu@fudan.edu.cn.
  • Jia Li
    Zhongshan Institute for Drug Discovery, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Zhongshan Tsuihang New District, Guangdong, 528400, PR China; School of Pharmacy, Zunyi Medical University, Zunyi, 563000, PR China; National Center for Drug Screening, State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, 201203, PR China.
  • Jin-Feng Hu
    Department of Natural Medicine, School of Pharmacy, Fudan University Shanghai 201203 PR China jxiong@fudan.edu.cn jfhu@fudan.edu.cn.

Keywords

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