Antiglycative and anti-inflammatory effects of lipophilized tyrosol derivatives
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(2020) 2:28
Food Production, Processing and Nutrition
RESEARCH
Open Access
Antiglycative and anti-inflammatory effects of lipophilized tyrosol derivatives Xiaoqian Hu1, Mingfu Wang2* and Fereidoon Shahidi2,3*
Abstract To expand the application of tyrosol, a series of lipophilized tyrosol derivatives were synthesized via esterification of tyrosol with fatty acids of different chain lengths. The antiglycative activity of tyrosol esters so prepared was subsequently examined in the bovine serum albumin/glucose system. A quasi-parabolic shape was observed when the activity was plotted against alkyl chain length. Additionally, the anti-inflammatory effects of these derivatives were evaluated against methylglyoxalinduced inflammation in RAW264.7 cells. The same trend on anti-inflammatory activity was found as in the antiglycation study. The results showed that tyrosol esters with C12:0 and C14:0 were two most efficient ones among all the tested derivatives. Thus, some lipophilized tyrosol derivatives were stronger antiglycative and anti-inflammatory agents compared to the parent compound, tyrosol. Keywords: Tyrosyl esters, Lipophilization, Glycation, Methylglyoxal, Inflammation, Phenolipids
Introduction Glycation is a non-enzymatic reaction between reducing sugars and proteins, forming an unstable Schiff base which rearranges to a relatively stable Amadori product (Yan et al. 2003). Glycation occurs in living organisms under normal and pathological conditions. Once Amadori product is formed, it follows a further reaction to produce dicarbonyl intermediates as precursors (Ahmed and Thornalley 2003). Advanced glycation end products (AGEs) are the outcome of glycation process with crosslinked and fluorescent structures (Luevano-Contreras and Chapman-Novakofski 2010). AGEs are found in different types of cells, particularly during aging and chorionic disorders such as diabetes and Alzheimer’s disease (Yamagishi and Matsui 2016). Besides, excessive accumulation of AGEs is thought to etiologically contribute to chronic pathologies (Crisostomo et al. 2013; Ramasamy et al. 2005). Methylglyoxal (MGO), a well-known precursor of AGEs, is generated in cells during oxidation of glucose as well as lipids (Thornalley 2005). MGO has been found in * Correspondence: [email protected]; [email protected] 2 College of Food Science and Technology, Shanghai Ocean University, Shanghai 201306, China Full list of author information is available at the end of the article
various tissues, where they may be involved in some detrimental processes, particularly under hyperglycemic conditions. MGO may interact with cellular proteins or extracellular matrix proteins to form AGEs, and impair the function of proteins, leading to cellular dysfunction like inflammation response (Cantero et al. 2007; Vulesevic et al. 2016). Therefore, strategies for preventing AGEs formation and AGEs/MGO-induced dysfunction have attracted much interest in recent years. Some polyphenolic compounds have previously been investigated to inhibit the formation of AGEs and sho
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