2. Academic Validation
  3. Trinor- and tetranor-eremophilane sesquiterpenoids with anti-neuroinflammatory activity from cultures of the fungus Septoria rudbeckiae

Trinor- and tetranor-eremophilane sesquiterpenoids with anti-neuroinflammatory activity from cultures of the fungus Septoria rudbeckiae

  • Phytochemistry. 2021 Mar;183:112642. doi: 10.1016/j.phytochem.2020.112642.
Li-Bin Lin 1,  Jian Xiao 2,  Yu-Qi Gao 1,  Qiang Zhang 1,  Rui Han 1,  Jian-Zhao Qi 1,  Wen-Bo Han 3,  Biao Xu 4,  Jin-Ming Gao 5
Affiliations

Affiliations

  • 1 Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A&F University, Yangling, Shaanxi, 712100, People's Republic of China.
  • 2 Shaanxi Key Laboratory of Phytochemistry, College of Chemistry and Chemical Engineering, Baoji University of Arts and Sciences, Baoji, Shaanxi, 721013, People's Republic of China.
  • 3 Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A&F University, Yangling, Shaanxi, 712100, People's Republic of China. Electronic address: wbhan@nwafu.edu.cn.
  • 4 College of Life Sciences, Tarim University, Aral, 843300, People's Republic of China. Electronic address: biaoxu2008@hotmail.com.
  • 5 Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A&F University, Yangling, Shaanxi, 712100, People's Republic of China. Electronic address: jinminggao@nwsuaf.edu.cn.
PMID: 33421888 DOI: 10.1016/j.phytochem.2020.112642
Abstract

Fifteen eremophilane sesquiterpenoids, including nine undescribed congeners, septeremophilane A-H, and chaetopenoid G, together with four conjugated unsaturated polyketide fatty acids, including an undescribed derivative, were isolated from cultures of the fungus Septoria rudbeckiae, a plant pathogenic fungus isolated from the halophyte Karelinia caspia. Septeremophilane A represents an unprecedented tetranor-eremophilane sesquiterpenoid with an α,β-unsaturated δ-lactone unit bearing a hemiacetal group, while septeremophilane B-H possesses a trinor-eremophilane skeleton. Their structures and absolute configurations were established based on spectroscopic data (NMR and HRESIMS), quantum chemical calculations and electronic circular dichroism (ECD) experiments. All metabolites were tested for nitric oxide (NO) production inhibition in lipopolysaccharide (LPS)-activated BV-2 microglial cells, while dendryphiellin D, septeremophilane D, and septeremophilane E were found to display significant inhibition, with IC50 values of 11.9 ± 1.0, 8.5 ± 0.1, and 6.0 ± 0.2 μM, respectively.

Keywords

Anti-neuroinflammatory activity; Asteraceae; Karelinia caspia (Pallas) Lessing; Mycosphaerellaceae; Septoria rudbeckiae; Tetranor-eremophilane sesquiterpenoid; Trinor-eremophilane sesquiterpenoid; Unsaturated polyketide fatty acid.

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