Synthesis of novel ursolic acid-gallate hybrids via 1,2,3-triazole linkage and its anti-oxidant and anti-inflammatory activity study

Synthesis of novel ursolic acid-gallate hybrids via 1,2,3-triazole linkage and its anti-oxidant and anti-inflammatory activity study Full article

Journal

Arabian Journal of Chemistry
ISSN: 1878-5379

Output data

Year: 2024, Volume: 17, Number: 5, Article number : 105762, Pages count : 27 DOI: 10.1016/j.arabjc.2024.105762

Tags

Ursolic acid; Gallic acid; Hybrids; Structure–activity relationships; Anti-inflammatory mechanism

Authors

Qi Zhiwen ¹ , Xie Pujun ¹ , Wang Zhihong ⁴ , Zhou Hao ¹ , Tao Ran ¹ , Popov Sergey A. ² , Yang Guliang ³ , Shults Elvira E. ² , Wang Chengzhang ¹

Affiliations

1	Institute of Chemical Industry of Forest Products, Chinese Academy of Forest
2	Novosibirsk Institute of Organic Chemistry
3	National Engineering Laboratory for Rice and By-products Processing, Food Science and Engineering College, Central South University of Forestry and Technology
4	Guangdong Provincial Key Laboratory of Silviculture, Protection and Utilization, Guangdong Academy of Forestry

Funding (1)

Российский Научный Фонд

23-73-00077

Excessive oxidation can lead to inflammation and affect health. Studies have shown that ursolic acid (UA) and gallic acid are widely employed in medicine and cosmetics owing to their obvious antioxidant and anti-inflammatory properties. In this study, a series of 16 novel UA hybrids tethered via 1,2,3-triazole to the modified gallate moieties were synthesized via CuAAC 1,3-cycloaddition reactions. In vitro, all derivatives were proved to be effective in antioxidation and anti-inflammation activities. Interestingly, compound 20 significantly inhibited the expression of pro-inflammatory cytokines including mRNA of inducible nitric oxide synthase (iNOS) (p < 0.05) and cyclooxygenase-2 (COX-2) (p < 0.01) in lipopolysaccharide (LPS)-induced RAW264.7 cells in a dose-dependent manner. The inhibitory effect of compound 20 on pro-inflammatory cytokines was closely associated with suppression of the LPS-activated PI3K/Akt signal pathway. Compound 20 significantly alleviated inflammation in the gastrointestinal tract of zebrafish in vivo. In addition, compound 20 showed good biosafety in cytotoxicity evaluation. This study provides a novel reference for the development of treatments for health problems related to anti-oxidation and anti-inflammation properties.

Qi Z. , Xie P. , Wang Z. , Zhou H. , Tao R. , Popov S.A. , Yang G. , Shults E.E. , Wang C.
Synthesis of novel ursolic acid-gallate hybrids via 1,2,3-triazole linkage and its anti-oxidant and anti-inflammatory activity study
Arabian Journal of Chemistry. 2024. V.17. N5. 105762 :1-27. DOI: 10.1016/j.arabjc.2024.105762 WOS Scopus OpenAlex

Submitted:	Nov 28, 2023
Accepted:	Mar 25, 2024
Published online:	Mar 26, 2024

Web of science:	WOS:001225600900001
Scopus:	2-s2.0-85189676255
OpenAlex:	W4393195332

DB	Citing
OpenAlex	6
Web of science	4