Synthesis, cytotoxicity evaluation and molecular docking studies on 2′,4′-dihydroxy-6′-methoxy-3′,5′-dimethylchalcone derivatives

Abstract

Semi-synthetic DMC derivatives were synthesised and displayed biological potency against various cancer cell lines.

Effects of 2′,4′-Dihydroxy-6′-methoxy-3′,5′-dimethylchalcone from Syzygium nervosum Seeds on Antiproliferative, DNA Damage, Cell Cycle Arrest, and Apoptosis in Human Cervical Cancer Cell Lines

“…TLC chromatogram of crude CH 2 Cl 2 extract from S. nervosum seeds visualized under UV 254 nm (Figure S2). The chemical structure of DMC was verified by comparison of its spectroscopic data to previously published values, and all values were found to be identical with previous study [15,16]. The physical appearance of DMC is a yellow needle-shaped crystals obtained from crystallization using n-hexane-CH 2 Cl 2 , and its melting point is 124.2-125.6 • C. The UV-VIS spectrum of DMC in phosphate buffered saline at pH 7.4 (Figure S3) showed and minor band of benzoyl system at wavelength of maximum absorbance (λ max ) of 228 nm and major band of cinnamoyl system at λ max of 395 nm, which are characteristic of flavonoids with a structural skeleton of chalcone [26].…”

“…TLC chromatogram of crude CH2Cl2 extract from S. nervosum seeds visualized under UV 254 nm (Figure S2). The chemical structure of DMC was verified by comparison of its spectroscopic data to previously published values, and all values were found to be identical with previous study [15,16]. The physical appearance of DMC is a yellow needle-shaped crystals obtained from crystallization using n-hexane-CH2Cl2, and its melting point is 124.2-125.6 °C.…”

“…This effect might occur through the inhibitory effects on carcinogen-bioactivated enzymes rather than a direct action on mutagens [10,11]. The main chemical compound isolated from the buds and seeds of S. nervosum is 2 ,4 -dihydroxy-6 -methoxy-3 ,5 -dimethylchalcone (DMC), which has been reported for biological activities, including anti-inflammatory, antiviral, antidiabetic, and anticancer [12][13][14][15][16].…”

“…Alternatively, natural products from agricultural waste can be used in pharmacological applications, such as the production of anticancer drugs and anticancer developments for high value-added products [15]. In addition, the main pure compound from the seeds of S. nervosum from agricultural waste is DMC [15,16]. The chemical structure of DMC has been elucidated, as shown in Figure 1 [15][16][17][18][19][20].…”

“…In addition, the main pure compound from the seeds of S. nervosum from agricultural waste is DMC [15,16]. The chemical structure of DMC has been elucidated, as shown in Figure 1 [15][16][17][18][19][20]. DMC is a chalcone derivative that has many reported biological activities, including anti-inflammatory, antiviral, antidiabetic, and anticancer [12][13][14][15].…”