Bioorganic and medicinal chemistry (2020)
Update date:2022-08-11
Topics:
Asao, Naoki
Hikita, Kiyomi
Kaneda, Norio
Kato, Kuniki
Matsuyama, Haruka
Murata, Tomiyasu
Nagai, Rina
Saigusa, Satomi
Takeuchi, Yuto
Tanaka, Hitoshi
Wagh, Yogesh S.
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.
View MoreChengdu Boon Stream Chemical Industry Co.,Ltd.
Contact:+86-28-83156758
Address:No.859,Dongzikou Road,Jinniu District,Chengdu,Sichuan,P.R.China
Chemvon Biotechnology Co. Ltd.
website:http://www.chemvon.com
Contact:86-21-58550039;86-21-31268550-8004
Address:Suite B-10#, 6999 Chuansha Road, Pudong District, Shanghai 201202, China
Contact:+86-10-67147360/67107388
Address:No.18 Guangming Zhongjie, Chongwen District, Beijing, 100061, China
Xuzhou Tianrun Chemical Co.,Ltd
website:http://www.tianrunchem.cn
Contact:86-516-83832636
Address:fuxing road
Jewim Pharmaceutical (Shandong) Co., Ltd
Contact:+8615621883869
Address:山东省泰安市高新技术产业开发区配天门大街西首
Doi:10.1002/chem.202100571
(2021)Doi:10.1016/j.ejmech.2017.06.033
(2017)Doi:10.1039/c4ra13700k
(2015)Doi:10.1246/cl.1989.449
(1989)Doi:10.1021/ac035417c
(2004)Doi:10.1002/1521-3773(20010803)40:15<2881::AID-ANIE2881>3.0.CO;2-P
(2001)