Elsevier

Fitoterapia

Volume 99, December 2014, Pages 92-98
Fitoterapia

Neolignans, lignans and glycoside from the fruits of Melia toosendan

https://doi.org/10.1016/j.fitote.2014.09.008Get rights and content

Abstract

Four new neolignans, meliasendanins A–D (14), and a new glycoside, toosenoside A (5), together with ten known ones (615), were isolated from a n-BuOH partition of the fruits of Melia toosendan. Their structures were elucidated by analyses of extensive spectroscopic data and comparison of the NMR data with those reported previously. Meliasendanin A (1) was a rare neolignan containing isochroman moiety, and its absolute configuration was determined using a CD spectrum. Toosenoside A (5) was an unusual glycoside with a rare naturally occurring aglycone and its structure was confirmed by X-ray single crystal diffraction analysis. The antioxidant activity of the isolated neolignans and lignans was evaluated by ABTS radical-scavenging assay. Compounds 1 and 13 exhibited strong antioxidant activity, with IC50 values of 62.8 and 45.1 μM, respectively.

Introduction

Melia toosendan Sieb. et Zucc. (Meliaceae) is widely distributed in the southwest region of China. The fruits of M. toosendan (“Chuan-Lian-Zi” in Chinese) is a traditional Chinese medicine (TCM) recorded in Pharmacopoeia of China and has been used as an antiparasitic and analgesic agent [1], [2], [3]. Previous phytochemical studies on different parts of M. toosendan have led to reports of a series of highly functionalized limonoids, euphane- and tirucallane-type triterpenoids, steroids and lignans [4], [5], [6], [7], [8], [9], [10], [11], [12], [13], [14], [15], [16], [17], [18], [19], [20]. The lipophilic phytochemicals of this species have been extensively investigated in recent years, while the hydrophilic constituents were rarely reported [21]. As part of a program to search for bioactive constituents from TCMs, this study mainly focused on the hydrophilic components. The n-BuOH-soluble part of the 95% EtOH extract of the fruits of M. toosendan was investigated, and four new neolignans, meliasendanins A–D (14), a new glycoside, toosenoside A (5) (Fig. 1), together with ten known compounds (including eight neolignans and two lignans) were isolated. Herein, we report the details of the isolation and structural elucidation of these new compounds, along with the evaluation of the antioxidant activity of the isolated neolignans and lignans.

Section snippets

General

Melting points (uncorrected) were determined on a X-6 precise melting point instrument. Optical rotations were measured by using a PerkinElmer 341 polarimeter at room temperature. CD spectra were recorded with an Olis DSM 1000 CD Spectropolarimeter. IR spectra were measured on a PerkinElmer 1725X-FT spectrometer. 1H and 13C NMR measurements were recorded on a Bruker Avance-600 spectrometer with TMS as the internal reference and chemical shifts are expressed in δ (ppm). HRESIMS were obtained

Results and discussion

Compound 1 was obtained as a yellow solid. The molecular formula was determined as C18H20O6 from the quasi-molecular ion peak [M + Na]+ at m/z 355.1149 (calcd for C18H20O6Na, 355.1152) in the positive-ion HRESIMS, representing 9° of unsaturation. The IR absorptions revealed the presence of hydroxyl (3367 cm 1) and aromatic (1612, 1519 and 1446 cm 1) functionalities. In the 1H NMR spectrum (Table 1), one ABX spin system signal at δH 6.95 (1H, d, J = 1.6 Hz, H-2), 6.78 (1H, dd, J = 8.1, 1.6 Hz, H-6) and

Conflict of interest

The authors declare no competing financial interest.

Acknowledgments

This work was supported by a grant from the Key Programs of Chinese Academy of Sciences (No. KSZD-EW-Z-004) and the National Science & Technology Pillar Program during the Eleventh Five-year Plan Period (No. 2011BAC09B04).

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