Synthesis and biological evaluation of moscatilin analogs as anti-inflammatory agents

GUAN Li; WANG Chunyang; ZHAO Huiru; LI Weize; FENG Feng

doi:10.11665/j.issn.1000-5048.20210205

Journal of China Pharmaceutical University > 2021 > 52(2): 171-176. > DOI: 10.11665/j.issn.1000-5048.20210205

GUAN Li, WANG Chunyang, ZHAO Huiru, LI Weize, FENG Feng. Synthesis and biological evaluation of moscatilin analogs as anti-inflammatory agents[J]. Journal of China Pharmaceutical University, 2021, 52(2): 171-176. DOI: 10.11665/j.issn.1000-5048.20210205

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Synthesis and biological evaluation of moscatilin analogs as anti-inflammatory agents

1.
College of Pharmacy, Xi'an Medical University, Xi'an 710021
2.
School of Clinical Medicine, Xi'an Medical University, Xi'an 710021
3.
Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing 211198, China

Funds: This study was supported by the Special Scientific Research Project of Shaanxi Provincial Department of Education (No. 20JK0895)

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Received Date: September 13, 2020
Revised Date: March 03, 2021

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Abstract

Using syringaldehyde as raw material, the phosphine ylide intermediate was efficiently synthesized through acetylated hydroxyl protection, aldehyde group reduction, chlorination and reaction with triphenylphosphine. On this basis, moscatilin (MST) and its 12 analogs (MST-1-MST-12) were synthesized by wittig reaction, deacetylation and double bond reduction. All the structures were confirmed by ¹H NMR, ¹³C NMR and ESI-MS. Bacterial lipopolysaccharide-induced mouse macrophage RAW264.7 inflammation model was used to conduct preliminary anti-inflammatory activity tests in vitro for the target compounds. Results showed that all compounds could inhibit the production of inflammatory factor NO, and that MST-5 exhibited the strongest anti-inflammatory activity (IC₅₀= 0.428 μmol/L).Further exploration is expected for the study of the anti-inflammatory mechanism of MST-5.
- moscatilin,
- bibenzyl,
- synthesis,
- anti-inflammatory activity

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