2. Academic Validation
  3. Induction of enantio-selective apoptosis in human leukemia HL-60 cells by (S)-erypoegin K, an isoflavone isolated from Erythrina poeppigiana

Induction of enantio-selective apoptosis in human leukemia HL-60 cells by (S)-erypoegin K, an isoflavone isolated from Erythrina poeppigiana

  • Bioorg Med Chem. 2020 Jun 1;28(11):115490. doi: 10.1016/j.bmc.2020.115490.
Kiyomi Hikita 1,  Satomi Saigusa 1,  Yuto Takeuchi 1,  Haruka Matsuyama 1,  Rina Nagai 1,  Kuniki Kato 2,  Tomiyasu Murata 1,  Hitoshi Tanaka 2,  Yogesh S Wagh 3,  Naoki Asao 4,  Norio Kaneda 5
Affiliations

Affiliations

  • 1 Laboratory of Analytical Neurobiology, Faculty of Pharmacy, Meijo University, 150 Yagotoyama, Tempaku, Nagoya 468-8503, Japan.
  • 2 Laboratory of Natural Product, Faculty of Pharmacy, Meijo University, 150 Yagotoyama, Tempaku, Nagoya 468-8503, Japan.
  • 3 Advanced Institute for Materials Research, Tohoku University, 2-1-1 Katahira, Aoba-ku, Sendai 980-8577, Japan.
  • 4 Advanced Institute for Materials Research, Tohoku University, 2-1-1 Katahira, Aoba-ku, Sendai 980-8577, Japan; Division of Chemistry and Materials, Graduate School of Science and Technology, Shinshu University, Ueda, Nagano 386-8567, Japan.
  • 5 Laboratory of Analytical Neurobiology, Faculty of Pharmacy, Meijo University, 150 Yagotoyama, Tempaku, Nagoya 468-8503, Japan. Electronic address: nkaneda@meijo-u.ac.jp.
PMID: 32299660 DOI: 10.1016/j.bmc.2020.115490
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.

Keywords

Anti-proliferative activity; Anti-tumor agent; Enantio-selective apoptosis induction; Erypoegin K; HL-60 cell; Isoflavone.

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