Antioxidant and anticancer activity of 3'-formyl-4', 6'-dihydroxy-2'-methoxy-5'-methylchalcone and (2S)-8-formyl-5-hydroxy-7-methoxy-6-methylflavanone.
Two new flavonoids - 3'-formyl-4',6'-dihydroxy-2'-methoxy-5'-methylchalcone (FMC) and (2S)-8-formyl-5-hydroxy-7-methoxy-6-methylflavanone (FMF) - isolated from the buds of Cleistocalyx operculatus, were investigated for their antioxidant and anticancer activity. Total antioxidant activity and reducing ability were measured. 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical and superoxide anion radical scavenging assays were carried out to evaluate the antioxidant potential of the two compounds. The antioxidant activity of the two compounds increased in a concentration-dependent manner. FMC and FMF at a concentration of 500 microM inhibited lipid peroxidation by 64.3 +/- 2.5% and 60.3 +/- 2.3%, respectively, an antioxidant activity approximately similar to that of 500 microM alpha-tocopherol (66.3 +/- 2.5%). Similarly, the effect of FMC and FMF on reducing power increased in a concentration-dependent manner. In DPPH radical scavenging assays, the IC50 values of FMC and FMF were 50.2 +/- 2.8 microM and 75.8 +/- 2.5 microM, respectively. Moreover, FMC and FMF scavenged the superoxide generated by the phenazine methosulfate (PMS)/reduced beta-nicotinamide adenine dinucleotide (NADH) nitroblue tetrazolium (NBT) system, with IC50 values of 56.3 +/- 2.3 microM and 317.5 +/- 2.9 microM, respectively. The anticancer activity of the two compounds were determined in five human cancer cell lines, SMMC-7721 (liver cancer), 8898 (pancreatic cancer), K562 (chronic leukaemia), HeLa (tumour of cervix uteri) and 95-D (high metastic lung carcinoma). FMC and FMF showed broad-spectrum anticancer activity against all the human cancer cell lines tested. The results obtained in the current study indicate that the two flavonoids could be a potential source of natural antioxidant and anticancer agents. To our knowledge, this is the first report on bioactivity of FMC and FMF.
Ye
Chun-Lin
CL
Department of Biological and Chemical Engineering, Zhejiang University of Science and Technology, Hangzhou 310012, PR China.
Liu
Yu
Y
Wei
Dong-Zhi
DZ
D000970:Antineoplastic Agents / Q000302:isolation & purification / Q000494:pharmacology*; D000975:Antioxidants / Q000302:isolation & purification / Q000494:pharmacology*; D001713:Biphenyl Compounds; D045744:Cell Line, Tumor / Q000187:drug effects; D047188:Chalcones / Q000302:isolation & purification / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D004365:Drugs, Chinese Herbal / Q000302:isolation & purification / Q000494:pharmacology*; D044950:Flavanones / Q000302:isolation & purification / Q000494:pharmacology*; D005419:Flavonoids / Q000302:isolation & purification / Q000494:pharmacology*; D035264:Flowers; D016166:Free Radical Scavengers; D006801:Humans; D015227:Lipid Peroxidation / Q000187:drug effects; D027822:Myrtaceae / Q000737:chemistry*; D008517:Phytotherapy; D010851:Picrates; D010946:Plants, Medicinal; D013481:Superoxides; D024502:alpha-Tocopherol / Q000494:pharmacology
C520277:(2S)-8-formyl-5-hydroxy-7-methoxy-6-methylflavanone; C520276:3'-formyl-4',6'-dihydroxy-2'-methoxy-5'-methylchalcone; D000970:Antineoplastic Agents; D000975:Antioxidants; D001713:Biphenyl Compounds; D047188:Chalcones; D004365:Drugs, Chinese Herbal; D044950:Flavanones; D005419:Flavonoids; D016166:Free Radical Scavengers; D010851:Picrates; D013481:Superoxides; C004931:1,1-diphenyl-2-picrylhydrazyl; D024502:alpha-Tocopherol