Elsevier

Phytochemistry Letters

Volume 13, September 2015, Pages 156-159
Phytochemistry Letters

Short communication
Isoflavones from the leaves of Nicotiana tabacum and their anti-tobacco mosaic virus activities

https://doi.org/10.1016/j.phytol.2015.05.009Get rights and content

Highlights

  • Three new (13) and three known flavones (4–6) were isolated from Nicotiana tabacum.

  • Compounds 1–3 were evaluated for their anti-tobacco mosaic virus (anti-TMV) activities.

  • They exhibited anti-TMV activities with inhibition rates of 25.2, 22.6, and 27.4%, respectively.

Abstract

Three new isoflavones, 4′,8-dihydroxy-6,7-dimethoxyisoflavone (1), 4′,6-dihydroxy-8-methoxycarbonyl-7-methoxyisoflavone (2), 4′,7-dimethoxy-8-hydroxymethyl-6-hydroxyisoflavone (3), together with three known flavones (46), were isolated from the leaves of Nicotiana tabacum. Their structures were elucidated by spectroscopic methods, including extensive 1D- and 2D NMR techniques. Compounds 13 were evaluated for their anti-tobacco mosaic virus (anti-TMV) activities. The results showed that compounds 13 (at the concentration of 20 μM) exhibited anti-TMV activities with inhibition rates of 25.2, 22.6, and 27.4%, respectively.

Introduction

Nicotiana tabacum, tobacco, is a stout herbaceous plant in the Solanaceae (nightshade family) that originated in the tropical Americas (South America, Mexico, and the West Indies) and now cultivated worldwide as the primary commercial source of tobacco, which is smoked or chewed as a drug for its mild stimulant effects (Hu et al., 2006, Kuang and Lu, 2005). In addition, N. tabacum is also used as insecticides, anesthetics, diaphoretics, sedatives, and emetic agents in Chinese folklore medicines because of its useful chemical compounds (Kuang and Lu, 2005, Rodgman and Perfetti, 2008). Previous phytochemical studies of tobacco have shown the presence of sesquiterpenes (Chen et al., 2014, Yang et al., 2013), alkaloids (Braumann et al., 1990, Wei et al., 2005), lignans (Chen et al., 2012a, Gao et al., 2012a), flavonoids (Chen et al., 2013, Chen et al., 2012b, Ye et al., 2012), phenylpropanoids (Leng et al., 2014, Tan et al., 2011), chromanones (Mou et al., 2012, Yang et al., 2014), Biphenyls (Shang et al., 2014a), phenolic amides (Shang et al., 2014b), isocoumarins (Shang et al., 2015), and the homologous. However, the previous reports on occurance of isoflavones in the Solanaceae family are still rather unusual (Arthan et al., 2002, Chen et al., 2012b, Sini and Devi, 2004, Ye et al., 2012).

In continuing efforts to the phytochemistry research on the tobacco leaves of Yunyan-85 (a variety of N. tabacum) led to the isolation of three new (13) and three known (46) isoflavones. This paper deals with the isolation, structural elucidation, and anti-TMV activities of these compounds.

Section snippets

Results and discussion

A 70% aq. acetone extract prepared from the leaves of N. tabacum was partitioned between EtOAc and H2O. The EtOAc layer was subjected repeatedly to column chromatography on Si gel, Sephadex LH-20, RP-18 and preparative HPLC to afford compounds 16, which included three new flavones, 4′,8-dihydroxy-6,7-dimethoxyisoflavone (1), 4′,6-dihydroxy-8-methoxycarbonyl-7-methoxyisoflavone (2), 4′,7-dimethoxy-8-hydroxymethyl-6-hydroxyisoflavone (3), together with three known flavones (46). The structures

General

UV spectra were obtained using a Shimadzu UV-2401A spectrophotometer. A Tenor 27 spectrophotometer was used for scanning IR spectroscopy with KBr pellets. 1D- and 2D NMR spectra were recorded on DRX-500 spectrometers with TMS as internal standard. Unless otherwise specified, chemical shifts (δ) were expressed in ppm with reference to the solvent signals. HRESIMS was performed on an API QSTAR time-of-flight spectrometer, or a VG Autospec-3000 spectrometer, respectively. Preparative HPLC was

Acknowledgments

This research was supported by the National Natural Science Foundation of China (No. 31360081), the Basic Research Foundation of Yunnan Province (2013FB097), and the Basic Research Foundation of Yunnan Tobacco Industry Co., Ltd. (2012JC01).

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