Synthesis and Biological Evaluation of Curcuminoid Derivatives

Abstract

Many curcuminoid derivatives have been reported to have multiple biological activities. The aim of this study was to improve the biological activity of curcuminoids by synthesizing 16 new derivatives which combined cinnamic acids with curcuminoids, and we also analyzed the structure-activity relationship of the new compounds. Almost all the new compounds showed encouraging activity, especially compound 7g. It had much better antioxidant activity than curcuminoids and Vitamin C (VC), and also had the most significant antibacterial activity, which was 5-folder better than ampicillin (one of the best marketed antibiotics) with a minimum inhibitory concentration (MIC) of 0.5 µg/mL against Gram-positive cocci (Staphylococcus aureus and Streptococcus viridans) as well as Escherichia coli and 0.6 µg/mL against Enterobacter cloacae. Compound 7g also showed the greatest anticancer activity with a much lower IC 50 , which was 0.51 µM against MCF-7, 0.58 µM against HepG-2, 0.63 µM against LX-2, and 0.79 µM against 3T3. The results suggest that these compounds have promising potential as candidates for the treatment of cancer and thus further studies are warranted.

Recent Advances of Curcumin Derivatives in Breast Cancer

“…It (IC 50 =0.51 μM) showed higher cytotoxic activity than curcumin (IC 50 =9.28 μM) and nearly equal to the positive control drug Adriamycin (IC 50 =0.47 μM) ( Table 1). [46] In 2019, He et al. synthesized compound 11 with enhanced solubility and stability by combining curcumin with niacin.…”

“…It (IC 50 = 0.51 μM) showed higher cytotoxic activity than curcumin (IC 50 = 9.28 μM) and nearly equal to the positive control drug Adriamycin (IC 50 = 0.47 μM) (Table 1). [46] In 2019, He et al synthesized compound 11 with enhanced solubility and stability by combining curcumin with niacin. Compound 11 (IC 50 = 73.40 μM) exhibited potent antiproliferative activity in breast cancer cells and selectively induced G2/M cell cycle arrest and tumor cell apoptosis, whose mechanism was dependent on the activation of p53 expression (Table 1).…”

Polyphenols with Anti-Inflammatory Properties: Synthesis and Biological Activity of Novel Curcumin Derivatives

“…Polyphenols consist of a wide range of compounds that have multiple therapeutic properties [ 1 , 2 , 3 , 4 ]. Curcumin ( 1 ) is a fascinating polyphenol with several biological effects, such as anti-inflammatory, neuroprotective, antioxidant, and anticancer activities [ 2 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 ]. This pleiotropic molecule is found in the rhizome of Curcuma longa , and is a diarylheptanoid with two O-methoxyphenols attached to a β-diketone moiety connected by two symmetrical olefinic bonds [ 13 ].…”

Design and preparation of derivatives of oleanolic and glycyrrhetinic acids with cytotoxic properties

“…32 In this research, we use the method of combination to prepare OA and GA esters to increase their lipophilicity and introduce organic acid groups to increase their polarity. We selected 10 kinds of organic acids (nicotinic acid, 33 indole-3-acetic acid, 3-indolebutyric acid, cinnamic acid, 34 isonicotinic acid, salicylic acid, 35 acetyl 4-hydroxycinnamic acid, 36 acetylsalicylic acid, acetyl 3-hydroxybenzoic acid and acetyl 4-hydroxybenzoic acid) with certain biological activity into the 3-OH position of the OA ester and GA ester, and finally synthesized 20 new OA and GA derivatives, of which 18 new compounds were the target products. We used five cancer cell lines (SGC-7901, MCF-7, Eca-109, HeLa and Hep-G2) to determine the antitumor activity and human skin fibroblasts (HSF) as a control.…”