Total Syntheses and Anti-inflammatory Activities of Syringin and Its Natural Analogues

  • J Nat Prod. 2021 Nov 26;84(11):2866-2874. doi: 10.1021/acs.jnatprod.1c00585.
Hongbo Dong  1  2 ,  Min Wu  1  3 ,  Yingying Wang  1 ,  Weihong Du  1 ,  Yujiao He  1 ,  Zheng Shi  2
Affiliations
  • 1. Antibiotics Research and Re-evaluation Key Laboratory of Sichuan Province, School of Pharmacy, Chengdu University, Chengdu 610052, China.
  • 2. School of Clinical Medical College & Affiliated Hospital, Chengdu University, Chengdu 610052, China.
  • 3. School of Food and Biological Engineering, Chengdu University, Chengdu, 610052, China.
PMID: 34658231 DOI: 10.1021/acs.jnatprod.1c00585
Abstract

Syringin (1), a natural bioactive glucoside isolated from the root of Acanthopanax senticosus (Rupr. Maxim.) Harms, possesses significant anti-inflammatory activity. In this study, we have accomplished the total syntheses of syringin (1), along with its natural analogues 2-12, from a common starting material, syringaldehyde (13), in 4-8 steps with an overall yields of 11.8-61.3%. The anti-inflammatory activities of these compounds were determined against NO production in the LPS-stimulated RAW264.7 cells. Among them, compounds 1-5, 7, and 9 exhibited different levels of anti-inflammatory activity.

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