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. 2018 Aug 1;23(8):1920.
doi: 10.3390/molecules23081920.

Lignan Glycosides and Flavonoid Glycosides from the Aerial Portion of Lespedeza cuneata and Their Biological Evaluations

Jiwon Baek  1 , Tae Kyoung Lee  2 , Jae-Hyoung Song  3 , Eunyong Choi  4 , Hyun-Jeong Ko  5 , Sanghyun Lee  6 , Sang Un Choi  7 , Seong Lee  8 , Sang-Woo Yoo  9 , Seon-Hee Kim  10 , Ki Hyun Kim  11
Affiliations

Lignan Glycosides and Flavonoid Glycosides from the Aerial Portion of Lespedeza cuneata and Their Biological Evaluations

Jiwon Baek et al. Molecules. .

Abstract

Lespedeza cuneata (Fabaceae), known as Chinese bushclover, has been used in traditional medicines for the treatment of diseases including diabetes, hematuria, and insomnia. As part of a continuing search for bioactive constituents from Korean medicinal plant sources, phytochemical analysis of the aerial portion of L. cuneata led to the isolation of two new lignan glycosides (1,2) along with three known lignan glycosides (3⁻7) and nine known flavonoid glycosides (8⁻14). Numerous analysis techniques, including 1D and 2D NMR spectroscopy, CD spectroscopy, HR-MS, and chemical reactions, were utilized for structural elucidation of the new compounds (1,2). The isolated compounds were evaluated for their applicability in medicinal use using cell-based assays. Compounds 1 and 4⁻6 exhibited weak cytotoxicity against four human breast cancer cell lines (Bt549, MCF7, MDA-MB-231, and HCC70) (IC50 < 30.0 μM). However, none of the isolated compounds showed significant antiviral activity against PR8, HRV1B, or CVB3. In addition, compound 10 produced fewer lipid droplets in Oil Red O staining of mouse mesenchymal stem cells compared to the untreated negative control without altering the amount of alkaline phosphatase staining.

Keywords: Lespedeza cuneata; adipocyte and osteoblast differentiation; cytotoxicity; flavonoid glycoside; lignan glycoside.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Chemical structures of compounds 1–14. Glc, glucopyranosyl; Rha, rhamnopyranosyl; Ara(f), arabinofuranosyl.
Figure 2
Figure 2
1H-1H COSY (formula image) and key HMBC (formula image) correlations for 1 and 2.
Figure 3
Figure 3
Reciprocal effects of compound 10 on the differentiation of MSCs into adipocytes or osteoblasts. Mouse mesenchymal stem cells (C3H10T1/2) were treated with 10 μM compound 10. After adipogenic differentiation, the cells were stained with Oil Red O (ORO), and the number of stained lipid droplets was quantitatively evaluated (A). After osteoblast differentiation, the cells were stained for ALP levels, and the ALP activity was measured (B). Ctrl represents untreated negative control. For the positive controls, 40 micrograms of resveratrol (Res) was used for adipogenesis and 5 μM of oryzativol A (OryA) was added for osteogenesis. * denotes 0.01 ≤ p ≤ 0.05 and *** denotes p ˂ 0.001.
See this image and copyright information in PMC

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