Formation and Identification of Two Hydroxmethylfurfural-Glycine Adducts and Their Cytotoxicity and Absorption in Caco-2 Cells.,Journal of Agricultural and Food Chemistry

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Formation and Identification of Two Hydroxmethylfurfural-Glycine Adducts and Their Cytotoxicity and Absorption in Caco-2 Cells.
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2019-12-17 , DOI: 10.1021/acs.jafc.9b06418
Rui Zeng ₁ , Guangwen Zhang ₁ , Jie Zheng ₁ , Hua Zhou ₁ , Ying Wang ₁ , Caihuan Huang ₁ , Wenzhong Hu , Shiyi Ou ₁

Affiliation

Our previous research showed that thioacetal and Schiff base formed between 5-hydroxymethylfurfural (HMF) and cysteine or lysine considerably decreased the cytotoxicity of HMF. In this study, two adol condensation adducts, named 2β-amino-3α-hydroxy-3-(5-(hydroxymethyl)furan-2-yl)propanoic acid (HGA) and 2α-amino-3β-hydroxy-3-(5-(hydroxymethyl)furan-2-yl)propanoic acid (HGB), were prepared from the reaction products of glycine and HMF, and their cytotoxicities were investigated in Caco-2 cells. Compared with HMF, HGA and HGB displayed lower cytotoxicities against Caco-2 cells with IC50 values of 36.50 and 43.47 mM, respectively, versus 16.11 mM (HMF). In contrast to our findings in thioacetal and Schiff base products, HGA and HGB underwent a very high metabolism rate (99%) in Caco-2 cells. HGA and HGB may degrade to other products instead of HMF since no extracellular or intracellular HMF was detected.

中文翻译：

两种羟甲基糠醛-甘氨酸加合物的形成和鉴定及其在Caco-2细胞中的细胞毒性和吸收。

我们以前的研究表明，5-羟甲基糠醛（HMF）与半胱氨酸或赖氨酸之间形成的硫缩醛和席夫碱可大大降低HMF的细胞毒性。在这项研究中，两个醛缩合加合物分别为2β-氨基-3α-羟基-3-（5-（羟甲基）呋喃-2-基）丙酸（HGA）和2α-氨基-3β-羟基-3-（5从甘氨酸和HMF的反应产物中制备了-（羟甲基）呋喃-2-基丙酸（HGB），并在Caco-2细胞中研究了它们的细胞毒性。与HMF相比，HGA和HGB对Caco-2细胞显示出较低的细胞毒性，IC50值分别为36.50和43.47 mM，而HMF为16.11 mM。与我们在硫缩醛和席夫碱产品中的发现相反，HGA和HGB在Caco-2细胞中的代谢率非常高（99％）。

更新日期：2019-12-18

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