Elsevier

Tetrahedron

Volume 69, Issue 32, 12 August 2013, Pages 6574-6578
Tetrahedron

Novel sesquiterpenes from Nardostachys chinensis Batal

https://doi.org/10.1016/j.tet.2013.05.134Get rights and content

Abstract

Seven new sesquiterpenes (17) as well as two known sesquiterpenes (89) were isolated from the underground parts of Nardostachys chinensis. Their structures were elucidated by spectroscopic data (NMR, MS) analyses. The absolute configurations were determined by single-crystal X-ray diffraction analysis, the modified Mosher's method, Snatzke's method, and the CD analysis of the in situ formed [Rh2(OCOCF3)4] complex.

Introduction

Nardostachys chinensis Batal, which belongs to the genus Nardostachys (Valerianaceae), is a perennial herb mainly distributed in the Himalayas mountain areas.1 It was well known for enriched with bioactive sesquiterpenes including a series of aristolane,2 nardosinane,3, 4, 5 guaiane-type6, 7 sesquiterpenes, of which exhibited antimalarial,6, 7 antinociceptive,7 and cytotoxic4 activities. In our effort in searching for cardiomyocytes protective sesquiterpenes from this plant, an aristolane-chalcone derivative and a nor-aristolane sesquiterpenoid were discovered.8 Further investigation of the underground parts of N. chinensis led to the isolation of seven new sesquiterpenes (17) along with two known aristolane sesquiterpenes (−)-aristolone (8),9 kanshone F (9)2 (Fig. 1). In this paper, we reported the isolation and structural elucidation of new compounds (17).

Section snippets

Result and discussion

Nardochinone A (1), obtained as colorless needles, had a molecular formula C15H22O4, determined by HRESIMS, with five degrees of unsaturation. The 13C NMR and DEPT spectra revealed 15 carbon signals, attributable to four methyl, two methylene, four methine (one oxygenated), and five quaternary carbons (two carbonyl, one oxygenated, and two olefinic). The olefinic carbons at δ 144.0, 175.1 and the carbonyl carbon at δ 209.7 showed characteristic chemical shifts for an α,β-unsaturated carbonyl

General experimental procedures

Optical rotations were measured on a Jasco P-1020 polarimeter with a 1 cm cell at room temperature. UV spectra were recorded on a JASCO V-550 UV/Vis spectrometer. IR spectra were obtained using a JASCO FT/IR-480 plus spectrometer. CD spectra were obtained on a Jasco J-810 spectropolarimeter at room temperature. HR-ESI-MS spectra were acquired using a Waters Synapt G2 mass spectrometer. The NMR spectra were measured with a Bruker AV-300/400/600 spectrometer at room temperature. Silica gel

Acknowledgements

This research was financially supported by National Major Scientific and Technological Special Project for ‘Significant New Drugs Development’ of China (Grant No. 2011ZX09201-201-28), and National Program on Key Basic Research Project of China (973 Program Grant No. 2012CB518606).

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These authors contributed equally to this work.

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