Elsevier

Phytochemistry Letters

Volume 12, June 2015, Pages 287-290
Phytochemistry Letters

Steroids from the aerial parts of Leonurus japonicus

https://doi.org/10.1016/j.phytol.2015.04.027Get rights and content

Highlights

  • Two new and ten known steroids were isolated from Leonurus japonicus.

  • The structure of 1 was confirmed by single crystal X-ray crystallographic analysis.

  • Compound 2 was characterized by esterification of β-sitosterol with an aliphatic diacid.

  • The isolates were assayed for anti-platelet aggregation activity and cytotoxic activity.

Abstract

Two new steroids, (24S)-stigmast-4,28-diene-24-ol-3-one (1) and mono-β-sitosteryl azelate (2), along with ten known analogues (312), were isolated from the ethanolic extract of Leonurus japonicus Houtt. Their structures were elucidated by spectroscopic and chemical methods. The absolute configuration of 1 was confirmed by single crystal X-ray crystallographic analysis using anomalous scattering of Cu Kα radiation. Compounds 3, 4, and 9 showed significant inhibitory activities against ADP-induced platelet aggregation, while compound 1 had a weak cytotoxic activity against acute myeloid leukemia cell line MV4-11.

Introduction

The aerial parts of Leonurus japonicus Houtt. (Lamiaceae) have been used for centuries as a common traditional Chinese medicine (Liu et al., 2012). Previous investigations on L. japonicus have led to the isolation of many terpenoids and aromatic compounds (Li et al., 2012, Moon, 2010, Romero-González et al., 2006, Seo et al., 2010, Xiong et al., 2015, Zhou et al., 2013). However, only a few steroids have been reported from the genus Leonurus before (Giang et al., 2005, Ye et al., 2014). The present phytochemical examination of the ethanolic extract of L. japonicus has resulted in the characterization of two new (1–2) and 10 known (3–12) steroids (Fig. 1). This paper describes the isolation, structure elucidation, and bioactivities of these isolates.

Section snippets

Results and discussion

Compound 1 was obtained as colorless needles in MeOH. The molecular formula C29H46O2 with seven degrees of unsaturation was indicated by HRESIMS at m/z 427.3593 [M + H]+ and 449.3406 [M + Na]+. The IR absorptions were observed at 3466, 1671, and 1617 cm−1, suggesting the presence of a hydroxyl group and an α,β-unsaturated ketone moiety in 1 (Yang et al., 2014). These observations were in agreement with the signals in the NMR spectrum [δH 5.72 (1H, s); δC 199.8, 171.8, 123.9, and 77.8] (Table 1). In

General experimental procedures

NMR spectra were recorded on a Bruker-AVIIIHD-600 spectrometer. HRESIMS were measured with a Waters Synapt G2 Q-TOF HDMS spectrometer. IR spectra were recorded on a Nicolet 5700 FT-IR microscope or a Perkin–Elmer Spectrum One FT-IR Spectrometer. X-ray data were obatined on a Xcalibur, Atlas, Gemini ultra diffractometer with Cu Kα radiation. Column chromatography was performed with silica Gel (200–300 mesh, Yantai Institute of Chemical Technology, Yantai, China), MCI gel CHP 20P (75–150 μm,

Conflict of interest

The authors declare no conflict of interest.

Acknowledgments

Financial support from the National Natural Sciences Foundation of China (NNSFC, Grant No. 81303209), China Postdoctoral Science Foundation Funded Project (CPSF, Grant No. 2014M562291), Sichuan Science and Technology Basic Research Program (Grant No. 2012JYZ005), and Sichuan Science and Technology Support Program (Grant No. 2011SZ0056) is acknowledged.

References (24)

  • M. Della Greca et al.

    Stigmasterols from Typha latifolia

    J. Nat. Prod.

    (1990)
  • P.M. Giang et al.

    New labdane-type diterpenoids from Leonurus heterophyllus SW

    Chem. Pharm. Bull.

    (2005)
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