Natural Product Sciences

The Korean Society of Pharmacognosy (한국생약학회)
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Anti-inflammatory and Neurotrophic 2H-1-Benzopyran Derivatives of Chaenomeles sinensis

  • Ha, Young Jun (School of Pharmacy, Sungkyunkwan University) ;
  • Lee, Tae Hyun (School of Pharmacy, Sungkyunkwan University) ;
  • Subedi, Lalita (Gachon Institute of Pharmaceutical Science, Gachon University) ;
  • Kim, Hye Ryeong (School of Pharmacy, Sungkyunkwan University) ;
  • Moon, Gyuri (Department of Biopharmaceutical Convergence, Sungkyunkwan University) ;
  • Kim, Sun Yeou (Gachon Institute of Pharmaceutical Science, Gachon University) ;
  • Kim, Chung Sub (School of Pharmacy, Sungkyunkwan University)
  • Received : 2021.08.14
  • Accepted : 2021.10.18
  • Published : 2022.03.31
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Abstract

Two 2H-1-benzopyran derivatives, methyl 8-hydroxy-2,2-dimethyl-2H-1-benzopyran-5-carboxylate (1) and methyl 8-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carboxylate (2), including a new compound (1) were isolated from the twigs of Chaenomeles sinensis. Their chemical structures were characterized based on analysis of NMR data including 1H and 13C, COSY, HSQC, and HMBC and HRMS data. The isolated compounds (1 and 2) were assessed for their anti-neuroinflammatory activity by measuring inhibition levels of nitric oxide (NO) production in lipopolysaccharide (LPS)-activated BV-2 cells and for their neurotrophic activity by the secretion of nerve growth factor (NGF) in C6 cells. Compounds 1 and 2 exhibited powerful anti-neuroinflammatory effects with IC50 values of 17.14 and 19.30 μM, respectively, without cell toxicity, and also showed moderate effects on the stimulation of NGF secretion levels with 113.15 ± 3.54 and 130.20 ± 8.03%, respectively. The biosynthetic pathway of 1 and 2 was proposed that they would be derived from a protocatechuic acid and an isoprenyl unit.

Keywords

Acknowledgement

This work was supported by the National Research Foundation (NRF) of Korea grant funded by the government of Korea (MSIT) (No. 2012M3A9C4048775) and by the BK21 FOUR Project. We are thankful to the Korea Basic Science Institute (KBSI) for the measurements on mass spectra.

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