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CC BY-NC-ND 4.0 · Planta Med 2017; 83(14/15): 1242-1250
DOI: 10.1055/s-0043-118226
Natural Product Chemistry and Analytical Studies
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Bupleurum chinense Roots: a Bioactivity-Guided Approach toward Saponin-Type NF-κB Inhibitors

Xin Liu   *
1   Institute of Pharmaceutical Sciences, Department of Pharmacognosy, University of Graz, Austria
,
Simone Latkolik   *
2   Department of Pharmacognosy, University of Vienna, Austria
,
Atanas G. Atanasov
2   Department of Pharmacognosy, University of Vienna, Austria
3   Institute of Genetics and Animal Breeding of the Polish Academy of Sciences, Jastrzebiec, Poland
,
Olaf Kunert
4   Institute of Pharmaceutical Sciences, Department of Pharmaceutical Chemistry, University of Graz, Austria;
,
Eva-Maria Pferschy-Wenzig
1   Institute of Pharmaceutical Sciences, Department of Pharmacognosy, University of Graz, Austria
,
Elke H. Heiss
2   Department of Pharmacognosy, University of Vienna, Austria
,
Clemens Malainer
2   Department of Pharmacognosy, University of Vienna, Austria
,
Andreas Schinkovitz
1   Institute of Pharmaceutical Sciences, Department of Pharmacognosy, University of Graz, Austria
,
Manfred Kollroser
5   Institute of Forensic Medicine, Medical University of Graz, Austria
,
Verena M. Dirsch
2   Department of Pharmacognosy, University of Vienna, Austria
,
Rudolf Bauer
1   Institute of Pharmaceutical Sciences, Department of Pharmacognosy, University of Graz, Austria
› Author Affiliations
Further Information

Publication History

received 18 February 2017
revised 04 August 2017

accepted 08 August 2017

Publication Date:
08 September 2017 (online)

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Abstract

The roots of Bupleurum chinense have a long history in traditional medicine to treat infectious diseases and inflammatory disorders. Two major compounds, saikosaponins A and D, were reported to exert potent anti-inflammatory activity by inhibiting NF-κB. In the present study, we isolated new saikosaponin analogues from the roots of B. chinese interfering with NF-κB activity in vitro. The methanol-soluble fraction of the dichloromethane extract of Radix Bupleuri was subjected to activity-guided isolation yielding 18 compounds, including triterpenoids and polyacetylenes. Their structures were determined by spectroscopic methods as saikogenin D (1), prosaikogenin D (2), saikosaponins B2 (3), W (4), B1 (5), Y (6), D (7), A (8), E (9), B4 (10), B3 (11), and T (12), saikodiyne A (13), D (14), E (15) and F (16), falcarindiol (17), and 1-linoleoyl-sn-glycero-3-phosphorylcholine (18). Among them, 4, 15, and 16 are new compounds, whereas 6, previously described as a semi-synthetic compound, is isolated from a natural source for the first time, and 13–17 are the first reports of polyacetylenes from this plant. Nine saponins/triterpenoids were tested for inhibition of NF-κB signaling in a cell-based NF-κB-dependent luciferase reporter gene model in vitro. Five of them (1, 2, 4, 6, and 8) showed strong (> 50%, at 30 µM) NF-κB inhibition, but also varying degrees of cytotoxicity, with compounds 1 and 4 (showing no significant cytotoxicity) presenting IC50 values of 14.0 µM and 14.1 µM in the cell-based assay, respectively.

Key words

Bupleurum chinense - Apiaceae - NF-κB - saponin - polyacetylene - lysophosphatidylcholine

* These authors contributed equally to this work.


Supporting Information

    Data regarding the inhibition of the NF-κB transactivation activity by pooled fractions 1 – 10 are shown in Fig. 1S of the supporting information. Also spectroscopic and spectrometric data for the identification of known compounds (1–3, 5, 7–14, and 17–18) are provided in the supporting information.

  • Supporting Information
 

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