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Comparison of the in vitro estrogenic activities of compounds from hops (Humulus lupulus) and red clover (Trifolium pratense).
J Agric Food Chem. 2005 Aug 10; 53(16):6246-53.JA

Abstract

Because the prevailing form of hormone replacement therapy is associated with the development of cancer in breast and endometrial tissues, alternatives are needed for the management of menopausal symptoms. Formulations of Trifolium pratense L. (red clover) are being used to alleviate menopause-associated hot flashes but have shown mixed results in clinical trials. The strobiles of Humulus lupulusL. (hops) have been reported to contain the prenylflavanone, 8-prenylnaringenin (8-PN), as the most estrogenic constituent, and this was confirmed using an estrogen receptor ligand screening assay utilizing ultrafiltration mass spectrometry. Extracts of hops and red clover and their individual constituents including 8-PN, 6-prenylnaringenin (6-PN), isoxanthohumol (IX), and xanthohumol (XN) from hops and daidzein, formononetin, biochanin A, and genistein from red clover were compared using a variety of in vitro estrogenic assays. The IC50 values for the estrogen receptor alpha and beta binding assays were 15 and 27 microg/mL, respectively, for hops and 18.0 and 2.0 microg/mL, respectively, for the red clover extract. Both of the extracts, genistein, and 8-PN activated the estrogen response element (ERE) in Ishikawa cells while the extracts, biochanin A, genistein, and 8-PN, significantly induced ERE-luciferase expression in MCF-7 cells. Hop and red clover extracts as well as 8-PN up-regulated progesterone receptor (PR) mRNA in the Ishikawa cell line. In the MCF-7 cell line, PR mRNA was significantly up-regulated by the extracts, biochanin A, genistein, 8-PN, and IX. The two extracts had EC50 values of 1.1 and 1.9 microg/mL, respectively, in the alkaline phosphatase induction assay. On the basis of these data, hops and red clover could be attractive for the development as herbal dietary supplements to alleviate menopause-associated symptoms.

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Authors+Show Affiliations

Overk CR
Department of Medicinal Chemistry and Pharmacognosy, UIC/NIH Center for Botanical Dietary Supplements Research, College of Pharmacy, M/C 781, University of Illinois, 833 South Wood Street, Chicago, Illinois 60612, USA.
Yao P
No affiliation info available
Chadwick LR
No affiliation info available
Nikolic D
No affiliation info available
Sun Y
No affiliation info available
Cuendet MA
No affiliation info available
Deng Y
No affiliation info available
Hedayat AS
No affiliation info available
Pauli GF
No affiliation info available
Farnsworth NR
No affiliation info available
van Breemen RB
No affiliation info available
Bolton JL
No affiliation info available

MeSH

Alkaline PhosphataseCell Line, TumorEstrogen Receptor alphaEstrogen Receptor betaEstrogensGene ExpressionHumansHumulusLuciferasesPhytoestrogensReceptors, ProgesteroneResponse ElementsTransfectionTrifolium

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, U.S. Gov't, P.H.S.

Language

eng

PubMed ID

16076101

Citation

Overk, Cassia R., et al. "Comparison of the in Vitro Estrogenic Activities of Compounds From Hops (Humulus Lupulus) and Red Clover (Trifolium Pratense)." Journal of Agricultural and Food Chemistry, vol. 53, no. 16, 2005, pp. 6246-53.
Overk CR, Yao P, Chadwick LR, et al. Comparison of the in vitro estrogenic activities of compounds from hops (Humulus lupulus) and red clover (Trifolium pratense). J Agric Food Chem. 2005;53(16):6246-53.
Overk, C. R., Yao, P., Chadwick, L. R., Nikolic, D., Sun, Y., Cuendet, M. A., Deng, Y., Hedayat, A. S., Pauli, G. F., Farnsworth, N. R., van Breemen, R. B., & Bolton, J. L. (2005). Comparison of the in vitro estrogenic activities of compounds from hops (Humulus lupulus) and red clover (Trifolium pratense). Journal of Agricultural and Food Chemistry, 53(16), 6246-53.
Overk CR, et al. Comparison of the in Vitro Estrogenic Activities of Compounds From Hops (Humulus Lupulus) and Red Clover (Trifolium Pratense). J Agric Food Chem. 2005 Aug 10;53(16):6246-53. PubMed PMID: 16076101.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Comparison of the in vitro estrogenic activities of compounds from hops (Humulus lupulus) and red clover (Trifolium pratense). AU - Overk,Cassia R, AU - Yao,Ping, AU - Chadwick,Lucas R, AU - Nikolic,Dejan, AU - Sun,Yongkai, AU - Cuendet,Muriel A, AU - Deng,Yunfan, AU - Hedayat,A S, AU - Pauli,Guido F, AU - Farnsworth,Norman R, AU - van Breemen,Richard B, AU - Bolton,Judy L, PY - 2005/8/4/pubmed PY - 2005/9/20/medline PY - 2005/8/4/entrez SP - 6246 EP - 53 JF - Journal of agricultural and food chemistry JO - J Agric Food Chem VL - 53 IS - 16 N2 - Because the prevailing form of hormone replacement therapy is associated with the development of cancer in breast and endometrial tissues, alternatives are needed for the management of menopausal symptoms. Formulations of Trifolium pratense L. (red clover) are being used to alleviate menopause-associated hot flashes but have shown mixed results in clinical trials. The strobiles of Humulus lupulusL. (hops) have been reported to contain the prenylflavanone, 8-prenylnaringenin (8-PN), as the most estrogenic constituent, and this was confirmed using an estrogen receptor ligand screening assay utilizing ultrafiltration mass spectrometry. Extracts of hops and red clover and their individual constituents including 8-PN, 6-prenylnaringenin (6-PN), isoxanthohumol (IX), and xanthohumol (XN) from hops and daidzein, formononetin, biochanin A, and genistein from red clover were compared using a variety of in vitro estrogenic assays. The IC50 values for the estrogen receptor alpha and beta binding assays were 15 and 27 microg/mL, respectively, for hops and 18.0 and 2.0 microg/mL, respectively, for the red clover extract. Both of the extracts, genistein, and 8-PN activated the estrogen response element (ERE) in Ishikawa cells while the extracts, biochanin A, genistein, and 8-PN, significantly induced ERE-luciferase expression in MCF-7 cells. Hop and red clover extracts as well as 8-PN up-regulated progesterone receptor (PR) mRNA in the Ishikawa cell line. In the MCF-7 cell line, PR mRNA was significantly up-regulated by the extracts, biochanin A, genistein, 8-PN, and IX. The two extracts had EC50 values of 1.1 and 1.9 microg/mL, respectively, in the alkaline phosphatase induction assay. On the basis of these data, hops and red clover could be attractive for the development as herbal dietary supplements to alleviate menopause-associated symptoms. SN - 0021-8561 UR - https://www.unboundmedicine.com/medline/citation/16076101/Comparison_of_the_in_vitro_estrogenic_activities_of_compounds_from_hops__Humulus_lupulus__and_red_clover__Trifolium_pratense__ DB - PRIME DP - Unbound Medicine ER -