| RRC ID |
58908
|
| Author |
Hikita K, Saigusa S, Takeuchi Y, Matsuyama H, Nagai R, Kato K, Murata T, Tanaka H, Wagh YS, Asao N, Kaneda N.
|
| Title |
Induction of enantio-selective apoptosis in human leukemia HL-60 cells by (S)-erypoegin K, an isoflavone isolated from Erythrina poeppigiana.
|
| Journal |
Bioorg Med Chem
|
| 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.
|
| Volume |
28(11)
|
| Pages |
115490
|
| Published |
2020-6-1
|
| DOI |
10.1016/j.bmc.2020.115490
|
| PII |
S0968-0896(20)30311-4
|
| PMID |
32299660
|
| MeSH |
Antineoplastic Agents, Phytogenic / chemistry
Antineoplastic Agents, Phytogenic / isolation & purification
Antineoplastic Agents, Phytogenic / pharmacology*
Apoptosis / drug effects*
Cell Proliferation / drug effects
Cell Survival / drug effects
Dose-Response Relationship, Drug
Drug Screening Assays, Antitumor
Eryptosis
Erythrina / chemistry*
HL-60 Cells
Humans
Molecular Structure
Stereoisomerism
Structure-Activity Relationship
Tumor Cells, Cultured
|
| IF |
3.073
|
| Times Cited |
0
|
| Resource |
| Human and Animal Cells |
HL-60(RCB3683) |
