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Planta Med 2005; 71(6): 495-500
DOI: 10.1055/s-2005-864148
Original Paper
Pharmacology
© Georg Thieme Verlag KG Stuttgart · New York

Phenolic Esters from the Rhizomes of Cimicifuga racemosa do not Cause Proliferation Effects in MCF-7 Cells

Stefan Stromeier1 , Frank Petereit1 , Adolf Nahrstedt1
  • 1Institute of Pharmaceutical Biology and Phytochemistry, Westfälische Wilhelms-Universität, Münster, Germany
Further Information

Publication History

Received: September 14, 2004

Accepted: December 29, 2004

Publication Date:
21 June 2005 (online)

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Abstract

Five phenylpropanoid esters, caffeoylglycolic acid, 2-caffeoylpiscidic acid (cimicifugic acid D), 3,4-dihydroxyphenacyl caffeate (petasiphenone), 3,4-dihydroxyphenyl-2-oxopropyl isoferulate (cimiciphenol) and 3,4-dihydroxyphenacyl isoferulate (cimiciphenone) were isolated from a commercially available extract of the rhizomes of Cimicifuga racemosa (L.) Nutt. (syn. Actaea racemosa L.) for the first time; the known cimicifugic acids A, B, E, F, fukinolic acid, fukiic acid and caffeic acid were also obtained. Cimiciphenone and caffeoylglycolic acid are new natural products. The structures were elucidated by means of spectroscopic data (ESI-MS, 1H-, 13C-NMR, COSY, HMQC, HMBC and NOE experiments). Ferulic acid and isoferulic acid were detected by HPLC analysis in comparison to standards. The estrogenic activity of the isolated compounds was tested in an estrogen-dependent MCF-7 mamma carcinoma cell line; 17β-estradiol (10-11 M) and the phytoestrogen coumestrol (10-7 - 10-5 M) were used as references. The results suggest that, in contrast to an earlier report, the phenolic esters do not exert a proliferative (estrogenic) effect in this test system.

Key words

MCF-7 cells - phytoestrogens - Cimicifuga racemosa - Actaea racemosa - Ranunculaceae - phenylpropanoid esters - cimiciphenone - caffeoylglycolic acid - estrogenic activity - E-Screen assay

References

  • 1 McKenna D J, Jones K, Humphrey S, Hughes K. Black Cohosh: Efficacy, Safety, and use in clinical and preclinical applications.  Altern Ther Health Med. 2001;  7 93-100
    PubMedSearch in Google Scholar
  • 2 Upton R. Monograph: Black Cohosh Rhizome. American Herbal Pharmacopoeia 2002
    Search in Google Scholar
  • 3 Liu Z -P, Yang Z -H, Zhu M -X, Huo J -S. Estrogenicity of black cohosh (Cimicifuga racemosa) and its effect on estrogen receptor level in human breast cancer MCF-7 cells.  J Hyg Res. 2001;  30 77-9
    PubMedSearch in Google Scholar
  • 4 Liu J, Burdette J E, Xu H, Gu C, van Breemen R B, Bhat K PL, Booth N, Constantinou A I, Pezutto J M, Fong H HS, Farnsworth N R, Bolton J L. Evaluation of estrogenic activity of plant extracts for the potential treatment of menopausal symptoms.  J Agric Food Chem. 2001;  49 2472-9
    CrossrefPubMedSearch in Google Scholar
  • 5 Löhning A M. Beitrag zur pharmakologischen Charakterisierung von Zubereitungen aus Cimicifuga racemosa Nutt., Ranunculaceae.  PhD thesis, University of Muenster 1999
    Search in Google Scholar
  • 6 Kruse S O, Löhning A, Pauli G, Winterhoff H, Nahrstedt A. Fukiic and piscidic acid esters from the rhizome of Cimicifuga racemosa and the in vitro estrogenic activity of fukinolic acid.  Planta Med. 1999;  65 763-4
    PubMedSearch in Google Scholar
  • 7 Soule H, Vazquez J, Long A, Albert S, Brennan M. A human cell line from a pleural effusion derived from a breast carcinoma.  J Natl Cancer Inst. 1973;  51 1409-13
    PubMedSearch in Google Scholar
  • 8 Soto A, Sonnenschein C, Chung K, Fernandez M, Olea N, Olea Serrano F. The E-SCREEN assay as a tool to identify estrogens: An update on estrogenic environmental pollutants.  Environ Health Perspect. 1995;  103 (Suppl 7) 113-22
    PubMedSearch in Google Scholar
  • 9 Takahira M, Kusano A, Shibano M, Kusano G, Miyase T. Piscidic acid and fukiic acid esters from Cimicifuga simplex .  Phytochemistry. 1998;  49 2115-9
    CrossrefPubMedSearch in Google Scholar
  • 10 Takahira M, Yanagi M, Kusano A, Shibano M, Baba K, Kusano G, Sakurai N, Nagai M. Phenolic constituents of Cimicifuga species rhizomes.  Natural Medicines. 1998;  52 330-8
    PubMedSearch in Google Scholar
  • 11 Yaoita Y, Kikuchi M. Petasiphenone, a phenolic compound from the rhizomes of Petasites japonicus .  Phytochemistry. 1994;  37 1773-4
    CrossrefPubMedSearch in Google Scholar
  • 12 Chen S, Fabricant D, Lu Z, Fong H, Farnsworth N. Cimiracemosides I - P, new 9,19-cyclolanostane triterpene glycosides from Cimicifuga racemosa .  J Nat Prod. 2002;  65 1391-7
    CrossrefPubMedSearch in Google Scholar
  • 13 Payne J, Jones C, Lakhani S, Kortenkamp A. Improving the reproducibility of the MCF-7 cell proliferation assay for the detection of xenoestrogens.  The Science of the Total Environment. 2000;  248 51-62
    CrossrefPubMedSearch in Google Scholar
  • 14 Körner W, Hanf V, Schuller W, Bartsch H, Zwirner M, Hagenmaier H. Validation and Application of a rapid in vitro assay for assessing the estrogenic potency of halogenated phenolic chemicals.  Chemosphere. 1998;  37 2395-407
    CrossrefPubMedSearch in Google Scholar
  • 15 Sakamura S, Yoshihara T, Toyoda K. Fukiic acid isolated from the hydrolysate of a polyphenol in Petasites japonicus .  Agr Biol Chem. 1969;  33 1795-7
    PubMedSearch in Google Scholar
  • 16 Kolodynska Z, Wieniawski W. Synthesis of caffeoylglycolic acids.  Act Pol Pharm. 1967;  XXIV 261-6
    PubMedSearch in Google Scholar
  • 17 Cos P, De Bruyne T, Apers S, Vanden Berghe D, Pieters L, Vlietinck A J. Phytoestrogens: Recent developments.  Planta Med. 2003;  69 589-99
    Thieme ConnectPubMedSearch in Google Scholar
  • 18 Hostanska K, Nisslein T, Freudenstein J, Reichling J, Saller R. Cimicifuga racemosa extract inhibits proliferation of estrogen receptor-positive and negative human breast carcinoma cell lines by induction of apoptosis.  Breast Cancer Res Treatm. 2004;  84 151-60
    PubMedSearch in Google Scholar
  • 19 Stromeier S. Phytochemische Untersuchungen und Prüfung auf estrogene Aktivität von phenolischen Inhaltsstoffen aus Cimicifuga racemosa (L.) Nutt. PhD thesis, University of Münster 2004
    Search in Google Scholar
  • 20 Tabanca N, Khan S I, Bedir E, Annavarapu S, Willet K, Khan I A, Kirimer N, Baser K HC. Estrogenic activity of isolated compounds and essential oils of Pimpinella species from Turkey, evaluated using a recombinant yeast screen.  Planta Med. 2004;  70 728-35
    Thieme ConnectPubMedSearch in Google Scholar

Prof. Dr. Adolf Nahrstedt

Westfälische Wilhelms-University

Institute of Pharmaceutical Biology and Phytochemistry

Hittorstr. 56

48149 Münster

Germany

Fax: ++41-251-833-8340

Email: nahrste@uni-muenster.de