Cimiracemates A–D, phenylpropanoid esters from the rhizomes of Cimicifuga racemosa
Four phenylpropanoid esters, cimiracemates A–D (1–4), were isolated from the EtOAc fraction of the rhizome of C. racemosa. Their structures were elucidated by means of spectral methods, including 2D NMR spectroscopy.
Introduction
The roots and rhizomes of Cimicifuga racemosa (L.) Nutt. (Actaea racemosa L.) (Ranunculaceae) (Compton et al., 1998), commonly known as black cohosh, have a long and diverse history of medicinal use dating back to native North American indigenous groups (Foster, 1999, McKenna et al., 2001). It is presently used in the treatment of climacteric symptoms related to menopause (Liske, 1998, Lieberman, 1998), with a clinical history spanning over the last 40 years (Stielhler, 1959, Foeldes, 1959, Stefan, 1959, Brucker, 1960, Schildge, 1964, Stolze, 1982, Vorberg, 1984, Jarry and Harnischfeger, 1985, Jarry et al., 1985, Pethoe, 1987, Duker et al., 1991). As part of our studies on botanical dietary supplements for women's health, we have been investigating the biological and chemical profiles of the rhizomes of this plant. Previously, we reported on the isolation and structure elucidation of 26-deoxyactein and the clarification of the nomenclature of 27-deoxyactein (Chen et al., 2002b), as well as on the isolation and structure determination of eight new 9,19-cyclolanostane-triterpene glycosides (cimiracemosides I-P) (Chen et al., 2002a).
In the present investigation, four phenylpropanoid esters, cimiracemates A–D (1–4) were isolated along with three known compounds: isoferulic acid, ferulic acid, and methyl caffeate from the rhizomes of C. racemosa. In this paper, the isolation of these compounds and the elucidation of their structures by means of spectral data are described.
Section snippets
Results and discussions
Cimiracemates A–D (1–4) were obtained by repeated chromatography of the EtOAc fraction prepared from the rhizomes of C. racemosa by sequential chromatography on silica gel (SiO2) and RP-18 columns, and C-18 HPLC.
Cimiracemate A (1) was obtained as a light brown powder. The molecular formula was determined to be C19H18O7 on the basis of a negative HR-ESIMS m/z 357.0974 (calc. 357.0974 for C19H17O7). UV absorptions at 291 (log ε: 3.77) and 325 (log ε: 3.96) nm showed that 1 has a conjugated
General
Mps uncorr. TLC precoated Kieselgel 60 F254 Si and RP-18 (0.25 mm, Merck). CC silica gel (mesh 230–400) eluted with CHCl3–MeOH (gradient) or CHCl3–acetone–H2O (17:1:0.1), and CC RP-18 (Lobar Lichroprep, 40–63 μm, 25×310 mm, Merck) eluted with MeOH–H2O (55:45) at the rate of 4 ml/min, 5% H2SO4 in n-BuOH and UV were used for detection of TLC. Semi-preparative HPLC was carried out on a Waters 996 system equipped with a photodiode array detector on a Watrex GROM-Sil 120 ODS-4 HE semipreparative
Acknowledgements
This research was funded by grant No. P50 AT00155 through the National Center for Complementary and Alternative Medicine (NCCAM), the Office of Dietary Supplements (ODS), the National Institute of General Medicine (NIGMS), and the Office for Research on Women's Health (ORWH). Contents are solely the responsibility of the authors and do not necessarily represent the official views of NCCAM, ODS, NIGMS or ORWH.
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