Biological Evaluation of Curcumin and Related Diarylheptanoids

Abstract

Nine derivatives of three natural diarylheptanoids, curcumin, demethoxycurcumin and bisdemethoxycurcumin, were prepared. Their antioxidant, free radical scavenging, nitric oxide (NO) inhibitory and cytotoxic activities were evaluated and compared with those of the respective natural compounds. Curcumin (1), demethoxycurcumin (2), demethyldemethoxycurcumin (C3), diacetyldemethoxycurcumin (AC2) and triacetyldemethylcurcumin (AC5) exhibited higher antioxidant activity than quercetin while products from demethylation of 1 and 2 exhibited higher free radical scavenging activity. Compounds AC2 and AC5 were found to be most active in inhibiting breast cancer cells (MCF-7) proliferation with IC50 values of 6.7 and 3.6 μм, respectively. The activity of AC2 is almost doubled and of AC5 almost tripled as compared to curcumin. Their selectivity towards different cell lines is also more noticeable. Compounds AC2 and AC5 also showed increased activity against a human prostate cancer cell line (DU-145) and non-small lung cancer cell line (NCI-H460) with IC50 values of 20.4, 16.3 and 18.3, 10.7 μм, respectively.

Structure elucidation and NMR assignments for curcuminoids from the rhizomes of Curcuma longa

“…Thus, compound 5 was identified as 1-(4-hydroxyphenyl)-7-(3, 4-dihydroxyphenyl)-1, 6-heptadiene-3, 5-dione. This is the first report of 5 from a natural source; however, Venkateswarlu [22] and Abas [23] had synthesized this compound. Its 13 C NMR data is reported here for the first time (Table 2).…”

Development and validation of UPLC method for quality control of Curcuma longa Linn.: Fast simultaneous quantitation of three curcuminoids

“…Curcuminoids have been studied for their anti-inflammatory, anti-Alzheimer, anti-cancer, anti-oxidant, hypoglycemic and anti-microbial features [6][7][8][9][10][11]. The three curcuminoids are the basis for the quality control of C. longa and other plant-derived drugs from the herb [12].…”

Cytotoxicity of Standardized Curcuminoids Mixture against Epithelial Ovarian Cancer Cell Line SKOV-3

“…Previous works showed different IC 50 values for DPPH radical-scavenging activity for curcuminoids. For example, curcumin, DMC, and BDMC displayed free radical scavenging activity with IC 50 values 31.8, 92.5, and 104.4 µM, respectively [23]. In another study by Akter et al, (2019), the IC 50 values were 18, 47, and 198 µM for curcumin, DMC, and BDMC, respectively [24].…”