Cytotoxic Oleanane-Type Triterpenoid Saponins from the Rhizomes of Anemone rivularis var. flore-minore

Xiaoyang Wang,Yi Wang,Haifeng Tang,Xiaoli Sun,Minchang Wang,Min Xu

doi:10.3390/molecules19022121

Xiaoyang Wang, Yi Wang + Show 4 more

Open Access

https://doi.org/10.3390/molecules19022121

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Journal: Molecules	Publication Date: Feb 18, 2014
Citations: 31	License type: CC BY 4.0

Affiliation: Air Force Medical University, Xijing Hospital

Abstract

Phytochemical investigation of the n-BuOH extract of the rhizomes of Anemone rivularis var. flore-minore led to the isolation of five new oleanane-type triterpenoid saponins 1–5, together with five known saponins 6–10. Their structures were determined by the extensive use of 1D and 2D NMR experiments, along with ESIMS analyses and acid hydrolysis. The aglycone of 4 and 5 was determined as 21α-hydroxyoleanolic acid, which was reported in this genus for the first time. The cytotoxicity of these compounds was evaluated against four human cancer cell line, including HL-60 (promyelocytic leukemia), HepG2 (hepatocellular carcinoma), A549 (lung carcinoma) and HeLa (cervical carcinoma). The monodesmosidic saponins 6–8 exhibited cytotoxic activity toward all tested cancer cell lines, with IC50 values in the 7.25–22.38 μM range.

Highlights

The genus Anemone (Ranunculaceae) consists of about 150 species with a nearly global distribution, of which about 50 species are found in China
Our previous phytochemical investigations of the whole plants of this species resulted in the isolation of a new gypsogenin saponin, a new diterpene glycoside, a new lignanoid glycoside, as well as a series of oleanane-type triterpenoid saponins [11,12]
Cytotoxicity was expressed as the concentration of drug inhibiting cell growth by 50% (IC50)

Summary

Introduction

The genus Anemone (Ranunculaceae) consists of about 150 species with a nearly global distribution, of which about 50 species are found in China. More than 10 species of this genus have been used as Chinese folk medicines for a long time. Our previous phytochemical investigations of the whole plants of this species resulted in the isolation of a new gypsogenin saponin, a new diterpene glycoside, a new lignanoid glycoside, as well as a series of oleanane-type triterpenoid saponins [11,12]. As part of our ongoing search for new bioactive natural compounds from this genus [11,12,13,14,15,16], the present study of the rhizomes of A. rivularis var. Flore-minore led to the isolation of five new oleanane-type saponins 1 5, along with five known saponins 6 10 (Figure 1). HL-60, hepatocellular liver carcinoma HepG2, lung carcinoma A549 and cervical carcinoma HeLa

Results and Discussion

General

Plant Material

Extraction and Isolation

Acid Hydrolysis and GC Analysis of the Sugar Moieties in 1–5

Assays for in Vitro Antitumor Activity

Conclusions