[Synthesis of baicalin derivatives and evaluation of their anti-human immunodeficiency virus (HIV-1) activity].
The aglycone baicalien(1) and the key intermediate 5,6-O-dibenzyl-baicalien(3) were prepared from baicalin in order to evaluate the influence of different glycosyloxies linked to baicalien on anti-HIV activity. Four new flavone-glycosides namely 5-hydroxyl-6-O-benzyl-flavone-7-beta-D-glucoside(12), 5-hydroxyl-6-O-benzyl-flavone-7-beta-D-galactoside(13), 5-hydroxyl-6-O-benzyl-flavone-7-alpha-D-mannoside(14) and 5-hydroxyl-6-O-benzyl-flavone-7-alpha-D-arabinoside (15) were synthesized by condensation of the corresponding protected glycosyl bromides with (3). Biological activity test showed that (a) both baicalin and baicalien inhibited HIV-1 RT; (b) the 6-hydroxyl substitution of baicalin and baicalien is necessary for their inhibitory activity on HIV-1 RT; (c) the HIV-1 inhibitory activity and cytotoxicity of baicalien were higher than those of baicalin, the two compounds were found to have almost identical therapeutic index.
Zhao
J
J
Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences, Beijing 100050.
Zhang
Z
Z
Chen
H
H
Zhang
X
X
Chen
X
X
D000998:Antiviral Agents / Q000138:chemical synthesis*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis; D044950:Flavanones; D005419:Flavonoids / Q000138:chemical synthesis* / Q000494:pharmacology; D054303:HIV Reverse Transcriptase / Q000378:metabolism; D015497:HIV-1 / Q000187:drug effects* / Q000201:enzymology; D006801:Humans
D000998:Antiviral Agents; D004791:Enzyme Inhibitors; D044950:Flavanones; D005419:Flavonoids; C038044:baicalin; C006680:baicalein; D054303:HIV Reverse Transcriptase