65388-04-7Relevant articles and documents
Induction of enantio-selective apoptosis in human leukemia HL-60 cells by (S)-erypoegin K, an isoflavone isolated from Erythrina poeppigiana
Asao, Naoki,Hikita, Kiyomi,Kaneda, Norio,Kato, Kuniki,Matsuyama, Haruka,Murata, Tomiyasu,Nagai, Rina,Saigusa, Satomi,Takeuchi, Yuto,Tanaka, Hitoshi,Wagh, Yogesh S.
, (2020/04/17)
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.
Anti-AGEs and antiparasitic activity of an original prenylated isoflavonoid and flavanones isolated from Derris ferruginea
Morel, Sylvie,Helesbeux, Jean-Jacques,Séraphin, Denis,Derbré, Séverine,Gatto, Julia,Aumond, Marie-Christine,Abatuci, Yannick,Grellier, Philippe,Beniddir, Mehdi A.,Le Pape, Patrice,Pagniez, Fabrice,Litaudon, Marc,Landreau, Anne,Richomme, Pascal
, p. 498 - 503 (2013/11/06)
A new isoflavonoid, 5-hydroxy-3-(4-hydroxyphenyl)-8-isopropenyl-8,9- dihydro-4H-furo-[2,3-h]-chromen-4-one named derrisisoflavone G (1), four known prenylated flavanones (2-5), four known isoflavonoids (6-9) and two phenolic derivatives (10, 11) have been
Selective C-6 prenylation of flavonoids via europium(III)-catalyzed claisen rearrangement and cross-metathesis
Tischer, Sandra,Metz, Peter
, p. 147 - 151 (2008/02/03)
Starting from the readily available parent flavonoids, the flavanone 6-prenylnaringenin, the isoflavone 6-prenylgenistein (wighteone, erythrinin B) and a protected derivative of the flavonol 6-prenylquercetin (gancaonin P) have been synthesized in short reaction sequences featuring the title processes as key steps.