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Anti-Inflammatory Lignans from the Fruits of Acanthopanax Sessiliflorus

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Anti-Inflammatory Lignans from the Fruits of Acanthopanax Sessiliflorus Molecules 2013, 18, 41-49; doi:10.3390/molecules18010041 OPEN ACCESS molecules ISSN 1420-3049 www.mdpi.com/journal/molecules Article Anti-inflammatory Lignans from the Fruits of Acanthopanax sessiliflorus Dae-Young Lee 1, Kyeong-Hwa Seo 2, Rak-Hun Jeong 2, Sang-Min Lee 2, Geum-Soog Kim 1, Hyung-Jun Noh 1, Seung-Yu Kim 1, Gye-Won Kim 3, Ji-Young Kim 2 and Nam-In Baek 2,* 1 Herbal Crop Utilization Research Team, National Institute of Horticultural and Herbal Science, RDA, Eumseong 369-873, Korea 2 Graduate School of Biotechnology and Department of Oriental Medicinal Materials & Processing, Kyung Hee University, Yongin 446-701, Korea 3 Brewing Research Center, Han Kyung National University, Ansung 456-749, Korea * Author to whom correspondence should be addressed; E-Mail: [email protected]; Tel.: +82-31-201-2661; Fax: +82-31-201-2157. Received: 24 August 2012; in revised form: 10 December 2012 / Accepted: 14 December 2012 / Published: 21 December 2012 Abstract: A new lignan, named acanthosessilin A (1), as well as eight known lignan and lignan glycosides 29 were isolated from an ethanolic extract of Acanthopanax sessiliflorus fruits. The chemical structures were determined by spectroscopic methods, including HR-EIMS, 1D NMR (1H, 13C, DEPT), 2D NMR (gCOSY, gHSQC, gHMBC, NOESY), and IR spectroscopy. All isolated compounds were tested for the ability to inhibit LPS-induced nitric oxide production in RAW264.7 macrophages. Keywords: Acanthopanax sessiliflorus; lignan; acanthosessilin A; nitric oxide 1. Introduction Acanthopanax sessiliflorus (Rupr. et Maxim) Seem, belonging to the Araliaceae family, is widely distributed in Korea, China, and Japan. The bark and twigs of Acanthopanax species are traditionally used in Korea as anti-rheumatoid arthritis, anti-inflammatory, and anti-diabetic drugs and are recognized to have ginseng-like activities [1,2]. Previous studies on its phytochemicals resulted in the isolation of lignans from the leaves and roots of Acanthopanax species [3–5], and eleutheroside E has been identified as a major compound in the fruits of Acanthopanax species [6]. Lignans are thought to Molecules 2013, 18 42 be the major active constituents of these plants and are believed to play essential roles in the treatment of diseases [7,8]. However, most phytochemical and pharmacological studies have mainly focused on the leaves, bark, and roots of Acanthopanax species, and only a few reports have investigated the fruits. Acanthopanax species are native medicinal plants and the fruits of Acanthopanax species have been used as a remedy to “wipe out evil wind” in traditional medicine [9]. To further investigate the bioactive constituents derived in the fruits of these species, the present phytochemical study was initiated. We report herein on the isolation of a new 3,4-dibenzylfuran lignan (1) from the fruits of A. sessiliflorus, together with eight known compounds 29, and the structural determination of these substances using extensive spectroscopic methods. Several previous studies have provided evidence for the anti-inflammatory effects of extracts and components from Acanthopanax species [10–12]. Therefore, isolated compounds 19 were evaluated for anti-inflammatory activities through the measurement of nitrite, a soluble oxidation product of nitric oxide (NO), in lipopolysaccharide (LPS)-induced RAW 254.7 macrophage cells. 2. Results and Discussion A 70% ethanolic extract of dried A. sessiliflorus fruits was suspended in H2O and extracted with EtOAc. The EtOAc soluble fraction was concentrated under reduced pressure to produce a residue that was subjected to multiple chromatographic steps using Sephadex LH-20, silica gel, and reversed-phase C18, yielding compounds 19 (Figure 1). Figure 1. Chemical structures of isolated compounds 19. Compound 1, obtained as colorless crystals from methanol, exhibited a UV absorption maximum at + 282 nm. The molecular formula was determined to be C20H24O6 from the molecular ion peak [M] at m/z 360.1552 (calcd for C20H24O6, 360.1572) in the HR-EIMS. IR absorption bands at 3,430, 1,648, and 1512 cm−1 were characteristic of hydroxyl and aromatic groups. The 1H-NMR spectrum showed three aromatic proton signals with J4 coupling at δH 6.90 (1H, d, J = 3.2 Hz, H-4), 6.76 (1H, overlapped, H-2), and 6.75 (1H, overlapped, H-6), which were assigned to a 1,3,5-trisubstituted benzene moiety. Three other aromatic proton signals at δH 6.78 (1H, d, J = 2.0 Hz, H-2'), 6.70 (1H, d, J = 8.0 Hz, H-6'), and 6.63 (1H, dd, J = 8.0, 2.0 Hz, H-5') corresponded to another 1,2,4-trisubstituted Molecules 2013, 18 43 benzene moiety. A doublet oxygenated methine proton signal at δH 4.74 (1H, J = 6.8 Hz), assigned to H-7, and two oxygenated methyl proton signals at δH 3.82 (3H) and 3.83 (3H) for two methoxy groups were observed. Two oxygenated methylene proton signals were observed at δH 3.97 (1H, dd, J = 8.4, 6.8 Hz), 3.71 (1H, dd, J = 8.4, 6.8 Hz), 3.82 (1H, overlapped), and 3.62 (1H, dd, J = 10.8, 6.4 Hz), which were assigned to H-9a, H-9b, H-9'a, and H-9'b, respectively. In the high magnetic field, two methine proton signals at δH 2.34 (1H, m, H-8) and 2.72 (1H, m, H-8'), and two methylene proton signals at δH 2.92 (1H, dd, J = 13.2, 4.8 Hz, H-7'a) and 2.48 (1H, dd, J = 13.2, 11.6 Hz, H-7'b) were observed, suggesting the presence of a furan moiety. The 13C-NMR spectrum showed twenty carbon signals, including two methoxy carbon signals [δC 56.3 (OMe-3,5)], confirming 1 to be a lignan. The multiplicity of each carbon was determined using a DEPT experiment. In the aromatic region, six olefin methine carbon signals [δC 122.1 (C-6'), 119.8 (C-5'), 116.1 (C-2), 115.9 (C-6), 113.3 (C-2'), and 110.6 (C-4)], two carbonated quaternary carbon signals [δC 135.7 (C-1) and 133.5 (C-1')] and four oxygenated quaternary carbon signals [δC 149.0 (C-3, 5), 147.0 (C-4'), and 145.7 (C-3')] due to the 1,3,5-tri- and 1,2,4-trisubstituted benzene moieties were observed. The oxygenated methine carbon signal at δC 84.0 (C-7) shifted downfield due to attached to heteroatom (–OH). Also, two oxygenated methylene carbon signals [δC 73.4 (C-9') and 60.4 (C-9)] and two methoxy carbon signals [δC 56.3 (3, 5-OMe)] were observed. In the high magnetic field, two methine carbon signals [δC 54.0 (C-8) and 43.8 (C-8')] and a methylene carbon signal [δC 33.6 (C-7')] were observed. With further analysis of the HSQC and DEPT 135 spectra of 1, the proton and carbon NMR signals could be assigned (Table 1). 1 1 The correlations in the H H COSY spectrum indicated key connectives of H-8 (δH 2.34) with H-7 (δH 4.74), H-8' (δH 2.72), H-9a (δH 3.97), and H-9b (δH 3.71) and H-8' (δH 2.72) with H-7'b (δH 2.48), H-9'a (δH 3.82), and H-9'b (δH 3.62) (Figure 2). In the HMBC spectrum, the long-range correlations of the two aromatic rings with the tetrahydrofuran ring were indicated by cross peaks between H-7 (δH 4.74) and C-2 (δC 116.1), C-6 (δC 115.9), and C-9 (δC 60.4) and between H-7' (δH 2.92, 2.48) and C-1' (δC 133.5), C-2' (δC 113.3), and C-6' (δC 122.1) (Figure 2). In addition, the long-range correlations between the proton signals of methoxy (δH 3.82, 3.83) and the oxygenated quaternary carbon signals of C-3, 5 (δc 149.0) were also identified. The relative stereochemistry of H-8 and H-8' 1 was identified as trans from the lack of NOE effect between H-8 and H-8'. The coupling constant of 6.8 Hz between 25 H-7 and H-8, as well as the optical rotation of 1 ([α] D = −43.5°) suggested an S configuration at C-7 [13]. A lignan with 7S and 8R configuration of similar structure, (3R,4R)-4-[(S)-(hydroxy)(4-hydroxy-3- 20 methoxyphenyl)methyl]-3-(4-hydoxy-3-methoxybenzyl)tetrahydrofuran ([α] D = −49°), supported the above, as reported in the literature [14]. The 13C-NMR spectra (C-7, C-8, C-7', C-8') and NOESY 25 experiment of 1 was very similar to (+) tripterygiol except for the optical rotation ([α] D = +48.3°) and were comparable to the epi-THF lignan [15]. This indicates that the H-8 and H-8' are present in (7S,8R)-configuration. Finally, the structure of 1 was determined to be 3-(3',4'-dihydroxybenzyl)-4-[(7S),7-hydroxy-3,5- dimethoxybenzyl]tetrahydrofuran, and named acanthosessilin A. Comparisons of NMR and MS data for the known compounds 2–9 with reported values led to their identification as (−)-sesamin (2) [16], (−)-hinokinin (3) [3], (+)-syringaresinol (4) [16], (+)-pinoresinol (5) [17], (+)-piperitol (6) [18], (+)-xanthoxylol (7) [19], acanthoside B (8) [20], and simlexoside (9) [21], respectively (Figure 1). Compounds 1, 6, 7, and 9 were isolated from the genus Acanthopanax for the first time. In addition, compounds 3 and 5 were also isolated from this plant for the first time. Molecules 2013, 18 44 1 13 Table 1. H- (400 MHz) and C-NMR (100 MHz) data of compound 1 (in CD3OD, δ in ppm, J in Hz) a.
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