Semisynthesis of apigenin and acacetin-7-O-β-D-glycosides from naringin and their cytotoxic activities.
Apigenin-7-O-β-D-glycosides 1-8 and acacetin-7-O-β-D-glycosides 9-16 were semisynthesized from 4'-O-benzyl apigenin 17 and acacetin 18 by glycosidation and deprotection with the corresponding α-acetylglycosyl bromide, respectively. Compounds 17 and 18 were prepared by iodination followed by base-induced elimination, 4'-O-benzylation, or 4'-O-methylation and acid hydrolysis using naringin as starting material which is readily available and cheap. Their cytotoxic potential against five human cancer cell lines (HL-60, SMMC-7721, A-549, MCF-7, and SW480) was evaluated by standard MTT method. The results show that compounds 2, 9, and 19 exhibit moderate cytotoxicity against HL-60, SMMC-7721, A-549, MCF-7, and SW480, while compound 3 exhibits potent cytotoxicity against MCF-7 selectively. Among the synthesized target compounds, 3, 4, 7, 11, 12, 15, and 16 were new compounds, the natural product 8 was the first synthesized and the synthesis of natural products 5, 6, 13, and 14 was efficiently improved by the new synthetic routes.
College of Chemistry and Chemical Engineering, Hunan University, ChangSha 410082, PR China.
Jidan
J
Liu
Ling
L
Chen
Shuanglian
S
Cai
Qiuan
Q
Wang
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D047310:Apigenin / Q000737:chemistry*; D045744:Cell Line, Tumor; D004353:Drug Evaluation, Preclinical; D044950:Flavanones / Q000737:chemistry*; D047309:Flavones / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis* / Q000494:pharmacology; D054879:Halogenation; D006801:Humans; D020128:Inhibitory Concentration 50
D000970:Antineoplastic Agents; D044950:Flavanones; D047309:Flavones; D006027:Glycosides; D047310:Apigenin; C023717:acacetin; C005274:naringin