Cimicifoetisides A and B, two cytotoxic cycloartane triterpenoid glycosides from the rhizomes of Cimicifuga foetida, inhibit proliferation of cancer cells
نویسندگان
چکیده
Two new cycloartane-type triterpene glycosides, namely cimicifoetisides A (1) and B (2), along with seven known compounds cimigenol, 25-O-acetylcimigenol, cimigenol 3-O-beta-D-xylopyranoside, 12beta-hydroxycimigenol 3-O-beta-D-xylopyranoside, cimigenol 3-O-alpha-L-arabinopyranoside, 25-deoxyshengmanol 3-O-beta-D-xylopyranoside and cimilactone A, were isolated from the rhizomes of Cimicifuga foetida. Their structures were elucidated as cimigenol 3-O-(2'-O-acetyl)-alpha-L-arabinopyranoside (1) and 25-O-acetylcimigenol 3-O-(2'-O-acetyl)-alpha-L-arabinopyranoside (2). Both compounds 1 and 2 exhibited potent cytotoxicity against rat EAC (Ehrlich ascites carcinoma) and MDA-MB-A231 (human breast cancer) cells with IC50 values of 0.52 and 6.74 microM for 1, and 0.19 and 10.21 microM for 2, suggesting their potential for further investigation as anti-cancer agents.
منابع مشابه
Effect of the standardized Cimicifuga foetida extract on Hsp 27 expression in the MCF-7 cell line.
Cimicifuga foetida, an Asian Cimicifuga species, has been employed as a cooling and detoxification agent in traditional Chinese medicine since ancient times. For this herb, two cycloartane triterpene glycosides isolated from the rhizomes have demonstrated cytotoxicity on rat tumor and human cancer cell lines. Since human Hsp27 is increased in various human cancers and exhibits cytoprotective ac...
متن کاملKHF16 is a Leading Structure from Cimicifuga foetida that Suppresses Breast Cancer Partially by Inhibiting the NF-κB Signaling Pathway
Triterpenoids extracted from Cimicifuga foetida have been reported to inhibit cancer by inducing cell cycle arrest and apoptosis. In this study, KHF16 (24-acetylisodahurinol-3-O-β-D-xylopyranoside), a cycloartane triterpenoid isolated from the rhizomes of C. foetida, showed potent anti-cancer activity in multiple ERα/PR/HER2 triple-negative breast cancer (TNBC) cell lines. KHF16 significantly i...
متن کاملTrinor-cycloartane glycosides from the rhizomes of Cimicifuga foetida.
Three new trinor-cycloartane glycosides, 15alpha-hydroxy-16-dehydroxy-16(24)-en-foetidinol-3-O-beta-D-xylopyranoside (1), 28-hydroxy-foetidinol-3-O-beta-D-xylopyranoside (2) and foetidinol-3-O-beta-D-xylopyranosyl-(1"-->3')-beta-D-xylopyranoside (3) together with the known compound foetidinol-3-O-beta-D-xylopyranoside (4) were isolated from the n-BuOH fraction of the roots of Cimicifuga foetida...
متن کاملCycloartane glycosides from the rhizomes of Cimicifuga racemosa and their cytotoxic activities.
Phytochemical analysis of the rhizomes of Cimicifuga racemosa (Ranunculaceae) resulted in the isolation of twelve cycloartane glycosides (1--12), including four new ones (4--6, 12). The structures of the new compounds were determined by spectroscopic analysis, including two-dimensional (2D) NMR data, and chemical methods. The isolated compounds were evaluated for their cytotoxic activities agai...
متن کاملCycloartane glycosides from Cimicifuga dahurica.
A new cycloartane bisdesmoside and two new trinorcycloartane glycosides, along with four known cycloartane compounds, were isolated from the rhizomes of Cimicifuga dahurica (Ranunculaceae). The structures of the new compounds were elucidated as 3-O-alpha-L-arabinopyranosyl cimigenol 15-O-beta-D-glucopyranoside, 24-hydroxy-12beta-acetoxy-25,26,27-trinorcycloartan-16,23-dione 3beta-O-alpha-L-arab...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Beilstein Journal of Organic Chemistry
دوره 3 شماره
صفحات -
تاریخ انتشار 2007