Anti-inflammatory and anti-oxidative activities of daidzein and its sulfonic acid ester derivatives. (August 2017)

• Record Type: Journal Article
• Authors: Peng, You; Shi, Yaning; Zhang, Hua; Mine, Yoshinori; Tsao, Rong
• Is Part Of: Journal of functional foods. Volume 35(2017)
• Page Start: 635
• Page End: 640
• Publication Date: 2017-08
• Subjects: Daidzein sulfonic acid ester -- Lipid/water partition coefficient -- Caco-2 epithelial cell -- Anti-inflammatory activity -- JNK; Daidzein (PubChem CID: 5281708); Functional foods -- Analysis -- Periodicals; Food -- Biotechnology -- Periodicals; Nutrition -- Periodicals; 613.2
• DOI: 10.1016/j.jff.2017.06.027
• Languages: English
• ISSNs: 1756-4646

Abstract

Highlights: Solubility and partition coefficient of daidzein were significantly improved by sulfonic acid esterification. Daidzein-4′-acetoxyl-7-benzene sulfonate had anti-inflammatory activity at 10 −2 μM. Daidzein-7-benzene sulfonate showed significant anti-oxidative effect at 100 μM. The derivatives significantly inhibited phosphorylation of JNK. Sulfonic acid esterification is an efficient improvement strategy. Abstract: To improve the activity of the isoflavone daidzein (1 ) and to explore its structure-activity relationship, new daidzein sulfonic acid ester derivatives (2 –4 ) were synthesized. All three derivatives showed significantly enhanced anti-inflammatory activities by 100–10, 000-fold over that of the parent daidzein in TNF-α-stimulated Caco-2 cells. Daidzein derivatives2 and3 showed the same anti-inflammatory effect at 1 μM and derivative4 had at 0.01 μM as 100 μM daidzein. Compound3 also showed significant anti-oxidative effect at 100 μM in H2 O2 -treated caco-2 cells. Treatment with daidzein and its derivatives significantly inhibited TNF-α-induced phosphorylation of JNK. Results suggest that sulfonic acid esterification at 4′- and/or 7- position of daidzein can significantly improve its physicochemical and pharmaceutical properties, consequently the cellular uptake or absorption and ultimately the biological activities.