Binding of Flavonoids from Sophora flavescens to 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.
Integrity signals
Registry
Cites
Statistics
Claims the paper makes
Claims other papers make about this one
Each is checked against this paper’s own text: does it say what the citing paper says it does?
Sophoflavescenol, a prenylated flavonol from Sophora flavescens, has anti-Alzheimer's disease activity.
“Some compounds such as sophoflavescenol, a prenylated flavonol segregated from S. flavescens have anti-AD activity [93]”
From Phytotherapy: A promising approach for the treatment of Alzheimer's disease (2022) · cites this paper as [93]
Cited by
Sorted by citations
Biology and chemistry of endophytes
Zhang, H., Song, Y., & Tan, R. X. (2006) · Natural Product Reports · doi:10.1039/b609472b · Cited by 998 · see citing works
He, X., Fang, J., Huang, L., et al. (2015) · Journal of Ethnopharmacology · doi:10.1016/j.jep.2015.06.010 · Cited by 334 · see citing works
Prenylated isoflavonoids from plants as selective estrogen receptor modulators (phytoSERMs)
Simons, R. G., Gruppen, H., Bovee, T. F. H., et al. (2012) · Food & Function · doi:10.1039/c2fo10290k · Cited by 111 · see citing works
Lee, H. W., Ryu, H. W., Kang, M.-G., Park, D., Oh, S., & Kim, H. (2016) · Bioorganic & Medicinal Chemistry Letters · doi:10.1016/j.bmcl.2016.08.044 · Cited by 105 · see citing works
Estrogenic flavonoids and their molecular mechanisms of action
Kiyama, R. (2022) · The Journal of Nutritional Biochemistry · doi:10.1016/j.jnutbio.2022.109250 · Cited by 82 · see citing works
Boozari, M., Soltani, S., & Iranshahi, M. (2019) · Phytotherapy Research · doi:10.1002/ptr.6265 · Cited by 76 · see citing works
Phytotherapy: A promising approach for the treatment of Alzheimer's disease
John, O. O., Amarachi, I. S., Chinazom, A. P., Adaeze, E., Kale, M. B., Umare, M. D., & Upaganlawar, A. B. (2022) · Pharmacological Research - Modern Chinese Medicine · doi:10.1016/j.prmcm.2021.100030 · Cited by 69 · see citing works
Phytochemistry and biological properties of isoprenoid flavonoids from Sophora flavescens Ait
Li, J., Zhang, X., Shen, X., et al. (2020) · Fitoterapia · doi:10.1016/j.fitote.2020.104556 · Cited by 66 · see citing works
Yang, X., Yang, J., Xu, C., Huang, M. N., Zhou, Q., Lv, J., Ma, X., Ke, C., Yang, Y., Shu, G., et al. (2015) · Journal of Ethnopharmacology · doi:10.1016/j.jep.2015.05.043 · Cited by 55 · see citing works
Ke, J., Cheng, J., Luo, Q., et al. (2020) · Food Chemistry · doi:10.1016/j.foodchem.2020.127816 · Cited by 54 · see citing works
Echeverria, V., Echeverria, F., Barreto, G. E., Echeverría, J., & Mendoza, C. (2021) · Frontiers in Pharmacology · doi:10.3389/fphar.2021.644103 · Cited by 52 · see citing works
Connolly, J. D., & Hill, R. A. (2008) · Natural Product Reports · doi:10.1039/b718038c · Cited by 46 · see citing works
Yang, X., Baburin, I., Plitzko, I., Hering, S., & Hamburger, M. O. (2011) · Molecular Diversity · doi:10.1007/s11030-010-9297-7 · Cited by 42 · see citing works
“4) which were identified as kushenol H (1), kushenol K (2), kurarinol (3), kushenol P (5), norkurarinol (6), kushenol I (7), kushenol N (8), (–)-kurarinone (9), kushenol X (10), neokurarinol (11), kushenol C (12), sophoraflavanone G (13), leachianone A (14), kuraridine (15), and kushenol A (16) by comparison of their…”
Chen, C., Tsai, P.-C., Wei, B., & Chiou, W. (2008) · European Journal of Pharmacology · doi:10.1016/j.ejphar.2008.05.018 · Cited by 39 · see citing works
Segun, P. A., Ogbole, O. O., Ismail, F. M. D., et al. (2019) · Fitoterapia · doi:10.1016/j.fitote.2019.02.019 · Cited by 28 · see citing works
“The known compounds vedelianin (4) [6], schweinfurthin G (5) [24], 8-prenylkaempferol (6) [25], mappain (7) [26], broussoflavonol F (8) [27], and isomacarangin (9) [11] were determined by the comparison of their spectroscopic data with those reported in the literature (Fig.”
Murray, T., Kang, J., Astheimer, L. B., et al. (2007) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf070266q · Cited by 25 · see citing works
Chen, L., Huang, X., Wang, H., et al. (2020) · Journal of Pharmaceutical and Biomedical Analysis · doi:10.1016/j.jpba.2020.113297 · Cited by 25 · see citing works
Chiou, W., Lee, C., Liao, J.-F., et al. (2010) · Life Sciences · doi:10.1016/j.lfs.2010.12.009 · Cited by 25 · see citing works
Polyphenols from Erythrina crista-galli: Structures, Molecular Docking and Phytoestrogenic Activity
Ashmawy, N. S., Ashour, M. L., Wink, M., et al. (2016) · Molecules · doi:10.3390/molecules21060726 · Cited by 23 · see citing works
“This finding is in agreement with our previous work showing the binding effect of prenylated flavonoids to the uterine estrogen receptor of rats [54]; the presence of a 5-hydroxy group and an 8-prenyl group were essential for such binding.”
ResultSelf-citationShen, G., Luo, Y., Yao, Y., et al. (2022) · Frontiers in Plant Science · doi:10.3389/fpls.2022.1034943 · Cited by 22 · see citing works
“In (1)H NMR spectrum (Figure S5), the characteristic signals (Hillerns and Wink, 2005; Kim et al., 2018) were identified as follows: dH=1.”
BackgroundConstituents from the Seeds of Sophora Alopecuroides L.
Rong, Z.-J., Hu, G., Lin, S.-Y., et al. (2020) · Molecules · doi:10.3390/molecules25020411 · Cited by 18 · see citing works
“The other known compounds were identified as (−)-maackiain (6) [8], neoliquiritin (7) [9], methyl 4-coumarate (8) [10], methyl ferulate (9) [11] and (+)-Wikstromol (10) [12] from the comparison of their NMR data with that reported in the literature.”
BackgroundLi, P., Chai, W. C., Wang, Z., et al. (2021) · Natural Product Research · doi:10.1080/14786419.2021.1983570 · Cited by 17 · see citing works
“…(2) (Mizobuchi and Sato 1984), (2S)-(-)-exiguaflavanone K (3) (Iinuma et al. 1994), (2S)(-)-sophoraflavanone G (4) (Shirataki et al. 1988), (2S)-leachianone A (5) (Hillerns and Wink 2005), (2S)-(-)-kushenol E (6) (Li et al. 2008a), (2S)-(-)-leachianone G (7) (Iinuma Figure 1.”
Ueng, Y., Chen, Y., Tsai, C.-C., et al. (2009) · Journal of Ethnopharmacology · doi:10.1016/j.jep.2009.09.018 · Cited by 17 · see citing works
Chiou, W., Chen, C., & Wei, B. (2009) · Evidence-based Complementary and Alternative Medicine · doi:10.1093/ecam/nep066 · Cited by 17 · see citing works
“Regarding the tested compound 8-PK, which exerted estrogenic activity by binding to rat uterine and was an effective inhibitor of α-glucosidase, a key enzyme involved in diabetes type 2 [32, 33].”
BackgroundYang, Y., Liu, T., Li, G., et al. (2023) · Molecules · doi:10.3390/molecules28052048 · Cited by 16 · see citing works
“alopecurone G (10) [21], sophoraflavone G (11) [22], leachianone A (12) [23], kurarinone”
BackgroundBioactive pterocarpans from Trigonella foenum-graecum L
Wu, Z. Y., Cai, Y., Yuan, R., et al. (2019) · Food Chemistry · doi:10.1016/j.foodchem.2019.126092 · Cited by 15 · see citing works
Kong, S., Liao, Q., Liu, Y., et al. (2024) · The American Journal of Chinese Medicine · doi:10.1142/s0192415x24500447 · Cited by 15 · see citing works
Lorenzana-Martínez, G., Santerre, A., Andrade‐González, I., & Bañuelos‐Pineda, J. (2020) · Nutritional Neuroscience · doi:10.1080/1028415x.2020.1804095 · Cited by 15 · see citing works
“It has also been shown that the flavonoids genistein and daidzein [73], among others, including cyanidin and del-”
Backgroundα-Glucosidase Inhibitors from the Roots of Sophora flavescens
Quang, T. H., Ngân, N. T. T., Minh, C. V., et al. (2012) · Bulletin of the Korean Chemical Society · doi:10.5012/bkcs.2012.33.5.1791 · Cited by 12 · see citing works
Long, G.-Q., Hu, G., Gao, X., et al. (2021) · Natural Product Research · doi:10.1080/14786419.2021.1894562 · Cited by 10 · see citing works
“…as 6,8-diprenylkaempferol (3) (Meragelman et al. 2001), (2S,20’S)-6-lavandulyl-7,40-dimethoxy-5,20-dihydroxylflavanone (4) (Cao et al. 2019), isoglabranin (5) (Kim et al. 2008) and 8-Prenylkaempferol (6) (Hillerns and Wink 2005) from their NMR data comparison with reported in the literature.”
BackgroundLignans and Flavonoids from Cajanus cajan (L.) Millsp. and Their α‐Glucosidase Inhibitory Activities
Lei, X., Liu, S., Zhao, Y., et al. (2022) · Chemistry & Biodiversity · doi:10.1002/cbdv.202200414 · Cited by 8 · see citing works
“The known compounds (Figure 1) were identified as isoswertisin (4),[14] taxifolin (5),[15] caudatan B (6),[16] (2R,4R)-2-(5-hydroxy-2-methylphenyl)-8-(3-methylbut2-en-1-yl)-4-(l-oxidaneyl)chromane-3,7-diol (7),[17] 8prenykaempferol (8),[18] 2-(2,4-dihydroxyphenyl)-3,5-dihydroxy-7-methoxy-8-(3-methylbut-2-en-1-yl)chrom…”
ResultShirataki, Y., & Motohashi, N. (2009) · Topics in heterocyclic chemistry · doi:10.1007/7081_2009_128 · Cited by 8 · see citing works
Wu, X., Tan, J., Liu, C.-F., et al. (2025) · Phytochemistry · doi:10.1016/j.phytochem.2025.114512 · Cited by 5 · see citing works
Estrogenic Prenylated Flavonoids in Sophora flavescens
Nishi, K., Imamura, I., Hoashi, K., et al. (2024) · Genes · doi:10.3390/genes15020204 · Cited by 4 · see citing works
“…sophoraflavanone G (8-lavandulyl-2 ′ -hydroxynaringenin) can be produced biosyn-thetically through 8-lavandulylation and 2 ′ -hydroxylation from 8-prenylnaringenin [30], which has strong estrogenic activity, it (norkurarinone) binds weakly to rat uterine ER (EC 50 of 8.224 ± 4.138 µ g/mL [29]).”
BackgroundInfluentialMa, Y.-Z., Zhang, D.-C., Yang, L., et al. (2025) · Phytochemistry · doi:10.1016/j.phytochem.2025.114654 · Cited by 3 · see citing works
Xu, Y., Chen, J., Li, Y., et al. (2024) · Phytochemistry · doi:10.1016/j.phytochem.2024.114288 · Cited by 3 · see citing works
Park, S., Lee, S., Weon, Y.-H., et al. (2021) · Plants · doi:10.3390/plants10081546 · Cited by 3 · see citing works
“It is also known that flavonoids such as 8-prenylkamperol, kushenol X, and norkurinone, which are major components from Sophora flavescens Aiton root extract, bind with estrogen receptors to exhibit physiological activity [38].”
BackgroundXu, Y., Chen, J., Li, Y., et al. (2024) · SSRN Electronic Journal · doi:10.2139/ssrn.4865649
- Authors
- Hillerns, P. I., & Wink, M.
- Affiliations
- Heidelberg University (DE)
- Venue
- Planta Medica
- Publisher
- Georg Thieme Verlag KG
- Published
- 2005-10
- Volume
- 71
- Issue
- 11
- Pages
- 1065-1068
- ISSN
- 0032-0943 (ISSN-L)
- 1439-0221
- OpenAlex
- W1963954388
- Cited by
- 38
- References
- 0
- Citations by year
- 2025: 2 · 2024: 4 · 2023: 1 · 2022: 3 · 2021: 5 · 2020: 5 · 2019: 3 · 2016: 2 · 2015: 2 · 2012: 2
- FWCI
- 0.50
- Type
- journal article
- Language
- de
- Open access
- closed
- Locations
- Planta Medica (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Bioactive natural compounds
- Health Sciences › Medicine › Pathology and Forensic Medicine › Phytoestrogen effects and research
- Life Sciences › Agricultural and Biological Sciences › Plant Science › Phytochemistry and Biological Activities
- Keywords
- Sophora flavescens, flavonoids, prenylated flavonoids, uterine estrogen receptor, maackiain, root extract, binding affinity, phytoestrogens
- MeSH terms
- Animals, Female, Flavonoids, Plant Extracts, Receptors, Estrogen, Uterus, Molecular Structure, Rats, Sprague-Dawley, Plant Roots, Sophora, Rats
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review
