Abstract:
:Erypoegin K, an isoflavone isolated from the stem bark of Erythrina poeppigiana, has potent apoptosis-inducing effect on human leukemia HL-60 cells. Erypoegin K has a chiral carbon at the C-2'' position of its furan ring and naturally occurs as a racemic mixture of (S)- and (R)-isomers. In the present study, we semi-synthesized (RS)-erypoegin K from genistein and separated the optical isomers by HPLC using a chiral column to characterize its apoptosis-inducing activity. Apoptotic cell death was assessed by analyzing caspase-3 and caspase-9 activation, nuclear fragmentation, and genomic DNA ladder formation. (S)-erypoegin K showed exclusive anti-proliferative and apoptosis-inducing activity, with an IC50 value of 90 nM, about 50% lower than that of its racemic mixture (175 nM). By contrast, no apoptosis-inducing activity was shown by the (R)-isomer. In addition, methylglyoxal accumulation in the culture medium was observed only in cells treated with (S)-erypoegin K. These results demonstrated that (S)-erypoegin K is a unique bioactive component that has potent apoptosis-inducing activity on HL-60 cells.
journal_name
Bioorg Med Chemjournal_title
Bioorganic & medicinal chemistryauthors
Hikita K,Saigusa S,Takeuchi Y,Matsuyama H,Nagai R,Kato K,Murata T,Tanaka H,Wagh YS,Asao N,Kaneda Ndoi
10.1016/j.bmc.2020.115490subject
Has Abstractpub_date
2020-06-01 00:00:00pages
115490issue
11eissn
0968-0896issn
1464-3391pii
S0968-0896(20)30311-4journal_volume
28pub_type
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