Estrogenic activity of constituents from the rhizomes of Rheum undulatum Linné

Seon Ju Park, Yun Na Kim, Hee Jae Kwak, Eun Ju Jeong, Seung Hyun Kim

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Stilbenes have been reported to be phytoestrogen compounds owing to its structural similarity to the estrogenic agent diethylstilbestrol. To find new stilbene-derivative phytoestrogens, isolation of stilbene-rich R. undulatum was performed and led to identify six new compounds (1–5 and 28), one newly determined absolute configurations compound (27) together with 21 previously reported compounds (6–26). The structures of compounds were determined on the basis of extensive spectroscopic methods including 1D and 2D NMR and CD spectra data. All the isolated compounds were tested for their estrogenic activities in HepG2 cells transiently transfected with ERα ERβ and ERE-reporter plasmid. Among them, stilbene-derivatives, piceatannol 3′-O-β-D-xylopyranoside (12), cis-rhaponticin (16) and rhapontigenin 3′-O-β-D-glucopyranoside (17), showed the more potent binding affinity for estrogen receptors than 17β-estrodiol.

Original languageEnglish
Pages (from-to)552-557
Number of pages6
JournalBioorganic and Medicinal Chemistry Letters
Volume28
Issue number4
DOIs
Publication statusPublished - 2018 Feb 15

Fingerprint

Rheum
Stilbenes
Rhizome
Phytoestrogens
Derivatives
Diethylstilbestrol
Hep G2 Cells
Estrogen Receptors
Estrogens
Plasmids
Nuclear magnetic resonance

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

Cite this

Park, Seon Ju ; Kim, Yun Na ; Kwak, Hee Jae ; Jeong, Eun Ju ; Kim, Seung Hyun. / Estrogenic activity of constituents from the rhizomes of Rheum undulatum Linné. In: Bioorganic and Medicinal Chemistry Letters. 2018 ; Vol. 28, No. 4. pp. 552-557.
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Estrogenic activity of constituents from the rhizomes of Rheum undulatum Linné. / Park, Seon Ju; Kim, Yun Na; Kwak, Hee Jae; Jeong, Eun Ju; Kim, Seung Hyun.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 28, No. 4, 15.02.2018, p. 552-557.

Research output: Contribution to journalArticle

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