Binding of Flavonoids fromSophora flavescensto the Rat Uterine Estrogen Receptor

Abstract

Prenylflavonoids and lavandulylflavonoids were isolated from the roots of Sophora flavescens Aiton (Fabaceae). The ability of 8-prenylkaempferol (1), kushenol X (2), norkurarinone (3), leachianone A (4), kushenol C (5), maackiain (6) and a root-extract of S. flavescens to displace 17beta-estradiol (E2) from rat uterine estrogen receptor (ER) was determined. Relative binding affinities (RBA) of prenylated flavonoids were weak with RBA values between 0.004 and 0.072. A lavandulyl or prenyl group at the position 8 enhanced binding to rat uterine ER.

Differential inductive profiles of hepatic cytochrome P450s by the extracts of Sophora flavescens in male and female C57BL/6JNarl mice

“…Although the prenylated flavonoids did not affect P450 activities, kurarinone has been reported to exhibit weak estrogenic activity (De Naeyer et al, 2004). A minor ingredient, 8-prenylnaringenin, has been reported to show moderate estrogen receptor-binding affinity in rat uterus (Hillerns and Wink, 2005). Our findings revealed that ingestion of extracts 1 and 2, but not extract 3 caused the gender-relative induction of Cyp2a and Cyp3a.…”

“…The methanol extract of S. flavescens showed estrogenic activity in Ishikawa cells (Yoo et al, 2005). Prenylated flavonoids of S. flavescens, 8-prenylnaringenin and kurarinone, have been reported to show moderate estrogen receptor-binding affinity in rat uterus and exhibit estrogenic activity in Ishikawa cells, respectively (De Naeyer et al, 2004;Hillerns and Wink, 2005). However, the effects of S. flavescens on P450s and the sexual difference in the induction of P450s by S. flavescens have not been reported.…”

Antidiabetic effects of flavonoids from Sophora flavescens EtOAc extract in type 2 diabetic KK-ay mice

“…Most of the remaining compounds were all structurally related 8-lavandulyl flavonoids (Fig. 2) which were identified as kushenol H (1) (Son et al, 2003), kushenol K (2) (Shin et al, 2002), kurarinol (5) , kushenol N (8) (Son et al, 2003), neokurarinol (10) (Kyogoku et al, 1973), kushenol C (11) (Hillerns & Wink., 2005), sophoraflavanone G (12) , leachianone A (13) (Kyogoku et al, 1973), kuraridine (14) , and kushenol A (15) by comparison of their MS, UV, and NMR spectra with published reference data. Other residual compounds were characterized as calycosin (3) and isoxanthohumol (7) , respectively.…”

Flavonoids in Sophora Species

“…However, a lavandulyl or prenyl group at position 8 on the flavonoids could enhance binding to the rat uterine ER (Fig. 12) [10]. …”