Mei Jin

Two new diarylheptanoids isolated from the roots of Juglans mandshurica.

Two new diarylheptanoids, ( − )-threo-3′,4″-epoxy-1-(4-hydroxyphenyl)-7-(3-methoxyphenyl)heptan-2,3-diol (1) and (1α,3β,5α,6α)-1,5-epoxy-3,6-dihydroxy-1,7-bis(3-methoxy-4-hydroxy-phenyl)-heptane (2), along with one known diarylheptanoid, rhoiptelol B (3), were isolated from the roots of Juglans mandshurica. The structures of compounds 1 and 2 were identified based on HR-ESI-MS, 1D and 2D NMR including 1H–1H COSY, HMQC, HMBC and NOESY spectroscopic methods.

A new phenolic glycoside from Juglans mandshurica

A new phenolic glycoside, 6-O-(4′-hydroxy-3′,5′-dimethoxybenzoyl)-d-glucopyranose (4), and nine known compounds (1–3 and 5–10) were isolated from Juglans mandshurica Maxim. Compound structures were elucidated by NMR, HR-ESI-MS and acid hydrolysis. Compounds 5 and 6 are reported from this genus for the first time. Among compounds 1–10, only 1 exhibited cytotoxicity against MGC-803, A549, K562, JAR, HeLa, CaSKi and SiHa cell lines (IC50: 2.0, 5.3, 2.3, 6.9, 4.0, 6.6 and 2.7 μM, respectively).

Chemical Constituents of the Leaves of Juglans mandshurica

Juglans mandshurica Maxim. (Juglandaceae), characterized as a deciduous tree, is widely distributed in China and Korea. Its leaves, fruits, roots, and stem barks have been used as a folk medicine for the treatment of cancer in Asia and Europe [1]. Previous phytochemical works on J. mandshurica reported polyphenols, quinones, flavonoids, terpenoids, and diarylheptanoids [2–8]. Some of them showed antioxidative, cytotoxic, and topoisomerase I and II inhibitory activity, anti-complement activity, and inhibitory effects on DNA polymerase and RNase H activity of HIV-1 reverse transcriptase [2–5, 8]. However, most phytochemical and pharmacological studies have mainly focused on the stem barks, roots, and fruits of J. mandshurica, and only a few reports have investigated the leaves. In continuation of our studies on this plant [5, 7, 9–11], 14 compounds, including four phenylpropanoids (1–4), six polyphenols (5–10), and four C13-norisoprenoids (11–14) were isolated from the leaves of J. mandshurica. To the best of our knowledge, compound 12 was firstly isolated from this plant and 1, 8–14 were isolated from the Juglans genus for the first time. The structures of these compounds were elucidated on the basis of spectroscopic analysis and comparison with the related compounds reported in the literature. Extraction and Isolation. The dried leaves of J. mandshurica (3 kg) were extracted with 70% MeOH (3 5 L) at room temperature. The MeOH extract (500 g) was suspended in H2O and partitioned in turn with petroleum ether (PE), CH2Cl2, EtOAc, and n-BuOH. The CH2Cl2 extract (5 g) was separated on a series of MPLC using a Bonna-Agela FCH120-S cartridge (120 g, CH2Cl2–MeOH, 100% CH2Cl2 to 100% MeOH, v/v), by Sephadex LH-20 column chromatography (MeOH), and finally purified by preparative HPLC (MeOH–H2O, 4:6 to 9:1, v/v) and HPTLC with a developing solvent system of PE–EtOAc to afford compounds 1–14. Compounds 1–10 were identified as caffeic acid methyl ester (1) [5, 7, 9–12], trans-coumaric acid methyl ester (2) [13], cinnamic acid (3) [14], ferulic acid (4) [15], gallic acid (5) [16], gallic acid methyl ester (6) [17], vanillin (7) [18], 1,3,5-trimethoxybenzene (8) [19], 4-hydroxybenzoic acid methyl ester (9) [20], and benzoic acid (10) [21] by comparison of their 1H and 13C NMR data with those reported in the literature. (6R,9S)-3-Oxo-ionol (11). Yellow amorphous solid; C13H20O2. [ ] 20 D +3.44 (c 0.20, MeOH). 1H NMR (300 MHz, CDCl3, , ppm, J/Hz): 0.95 (3H, s, H-11), 1.01 (3H, s, H-12), 1.26 (3H, d, J = 6.4, H-10), 1.88 (3H, s, H-13), 2.03 (1H, d, J = 16.0, H-2b), 2.33 (1H, d, J = 16.0, H-2a), 2.49 (1H, d, J = 8.9, H-6), 4.31 (1H, m, H-9), 5.49 (1H, dd, J = 16.0, 9.0, H-7), 5.63 (1H, dd, J = 16.0, 6.3, H-8), 5.88 (1H, s, H-4). 13C NMR (75 MHz, CDCl3, , ppm): 23.6 (C-13), 23.8 (C-10), 27.3 (C-11), 28.0 (C-12), 36.3 (C-1), 47.5 (C-2), 55.5 (C-6), 68.4 (C-9), 125.9 (C-7), 126.6 (C-4), 138.6 (C-8), 162.2 (C-5), 199.5 (C-3) [22, 23].

A new chromene from the fruiting bodies of Chroogomphus rutilus

A new chromene, acetic acid 2R-(4,8-dimethylnona-3,7-dienyl)-8-hydroxy-2-methyl-2H-chromen-6-yl ester (1), was isolated from the fruiting bodies of Chroogomphus rutilus, together with six known compounds (2–7). The structures of these compounds were identified based on 1D and 2D NMR, including 1H–1H COSY, HMQC and HMBC spectroscopic methods. Of these seven compounds, 2 and 3 showed cytotoxicity against HSC-T6, SK-Hep1 and A549 cell lines.

A new phenyl glycoside from the aerial parts of Equisetum hyemale

A new phenyl glycoside, 2-(sophorosyl)-1-(4-hydroxyphenyl)ethanone (9), was isolated from the ethanolic extract of the aerial parts of Equisetum hyemale L., together with eight known compounds (1–8). The structures of these compounds were elucidated using a combination of spectroscopic analyses and chemical method. Of these nine compounds, 4 and 7 showed hepatoprotective effects towards tacrine-induced cytotoxicity in Hep 3B cells with EC50 values of 42.7 ± 1.5 and 132.6 ± 2.8 μM, respectively.

One new 1,4-napthoquinone derivative from the roots of Juglans mandshurica

Abstract A new 1,4-napthoquinone derivative, namely (S)-(-)-3-(8-hydroxy-1,4-dioxo-1,4-dihydro-naphthalen-2-yl)-3-(4-hydroxy-3-methoxyphenyl)-propionic acid methyl ester (1), was isolated from the roots of Juglans mandshurica Maxim. The structure was identified based on HR-ESI-MS, 1D and 2D NMR spectroscopic methods.

A new diarylheptanoid and a new diarylheptanoid glycoside isolated from the roots of Juglans mandshurica and their anti-inflammatory activities

Abstract A new diarylheptanoid, (2S,3S,5S)-2,3,5-trihydroxy-1,7-bis(4-hydroxy- 3-methoxyphenyl)heptane (1), and a new diarylheptanoid glycoside, (2S,3S,5S)-2,3-dihydroxy-5-O-β-d-xylopyranosyl-7-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)heptane (2), together with three known compounds, rhoiptelol C (3), rhoiptelol B (4) and 3′,4″-epoxy-2-O-β-d-glucopyanosyl-1-(4-hydroxyphenyl)- 7-(3-methoxyphenyl)heptan-3-one (5) were isolated from the roots of Juglans mandshurica (Juglandaceae). The structures of compounds 1 and 2 were identified based on HR-ESI-MS, 1D and 2D NMR spectroscopic methods. Compounds 1–5 were assayed for their inhibitory effects on the production of NO, TNF-α and IL-6 in LPS-stimulated RAW264.7 cells.

Two new conjugated ketonic fatty acids from the stem bark of Juglans mandshurica.

The present study was designed to isolate and characterize novel chemical constituents of the stem bark of Juglans mandshurica Maxim. (Juglandaceae). The chemical constituents were isolated and purified by various chromatographic techniques. The structures of the compounds were elucidated on the basis of spectral data (1D and 2D NMR, HR-ESI-MS, CD, UV, and IR) and by the comparisons of spectroscopic data with the reported values in the literatures. Two long chain polyunsaturated fatty acids (1 and 2) were obtained and identified as (S)-(8E,10E)-12-hydroxy-7-oxo-8,10-octadecadienoic acid (1) and (S)-(8E, 10E)-12-hydroxy-7-oxo-8,10-octadecadienoic acid methyl ester (2). To the best of our knowledge, this is the first report on the isolation and structural elucidation of the two new conjugated ketonic fatty acids from this genus.

Anti-inflammatory activities of the chemical constituents isolated from Trametes versicolor

Abstract Twenty-seven compounds including nine triterpenoids (1–9), eight sterols (10–17), two ribonucleotides (18, 19), four phenols (20–23), three glycosides (24–26), and one furan (27) were isolated from the fruiting bodies of Trametes versicolor (L.) Lloyd. This study is the first confirmation of the presence of the 11 compounds (3, 5, 6, 8, 18, 20, 21, 23–25, and 27) isolated from the Polyporaceae family, with six of these (2 and 12–16) from the genus Trametes. Compounds 3, 4, 10, 11, 16 and 17 were found to significantly inhibit the production of NO, TNF-α and IL-6 in a dose-dependent manner.

Chemical Constituents of the Stem Barks of Quercus mongolica

Quercus mongolica Fisch. (Fagaceae) is a deciduous tree growing in or near the forest gaps, mainly distributed in China, Japan, Korea, and eastern Mongolia. The stem bark of Q. mongolica has been traditionally used for the treatment of dysentery, jaundice, hemorrhoids, and enteritis [1]. Previous investigations on Q. mongolica have reported flavonoids, polyphenols, triterpenoids, paclitaxel, and sterols with hepatoprotective, antioxidant, and anticancer activities [2–8]. In our continuous effort to explore potential active ingredients from this plant, 16 compounds, including two sterols (1, 2), two triterpenes (3, 4), two glycosides (5, 6), four flavonoids (7–10), three phenols (11–13), and three coumarins (14–16) were isolated from the stem bark of Q. mongolica. This is the first report of compound 6 from the family Fagaceae, compounds 5, 6, and 16 from the genus Quercus, and compounds 3–7, 12, 15, and 16 from Q. mongolica. The structures of compounds 1–16 were identified by comparison of the experimental and reported physicochemical data. Extraction and Isolation. The dried stem barks of Q. mongolica (5 kg) were extracted with EtOH (20 L × 3) at room temperature. The crude extract (739 g) was suspended in water and further partitioned with CH2Cl2, EtOAc, and n-BuOH, in succession. The EtOAc extract (45 g) was subjected to a series of open silica gel columns (petroleum ether–EtOAc, 20:1 to 3:1, CH2Cl2–MeOH, 20:1 to 5:1) and purified by MPLC (MeOH–H2O, 9:1 to 7:1) to afford compounds 1–3 and 7–12. The CH2Cl2 extract (136 g) was loaded into a series of open silica gel columns (CH2Cl2–MeOH, 15:1 to 100% MeOH) and purified by preparative HPLC (MeOH–H2O, 10:1 to 7:3) to give compounds 4–6 and 13–16. Compounds 1–16 were identified as β-sitosterol (1) [9], daucosterol (2) [10], (+)-ursolic acid (3) [11], maslinic acid (4) [11], methyl-α-D-fructofuranoside (5) [12], methyl-β-D-fructofuranoside (6) [12], (+)-dihydrokaempferol (7) [13], (+)-catechin (8) [14], (–)-dihydroquercetin (9) [15], quercetin (10) [16], vanillin (11) [17], ethyl gallate (12) [18], tachioside (13) [19], scopoletin (14) [12], scopolin (15) [12], and fraxin (16) [20] by comparison of their 1H and 13C NMR data with the spectroscopic data reported in the literature. (+)-Ursolic Acid (3). White amorphous powder, C30H48O3. 1H NMR spectrum (300 MHz, CD3OD, δ, ppm, J/Hz): 0.73 (3H, s, H-24), 0.82 (3H, s, H-25), 0.83 (3H, d, J = 6.3, H-29), 0.91 (3H, s, H-23), 0.92 (3H, d, J = 6.3, H-30), 1.07 (3H, s, H-26), 1.24 (3H, s, H-27), 3.10 (1H, dd, J = 10.7, 4.6, H-3), 5.18 (1H, t, J = 3.7, H-12) [11]. Maslinic Acid (4). Yellow amorphous powder, C30H48O4. 1H NMR spectrum (300 MHz, CD3OD, δ, ppm, J/Hz): 0.78 (3H, s, H-29), 0.79 (3H, s, H-26), 0.89 (3H, s, H-25), 0.92 (3H, s, H-30), 0.98 (3H, s, H-24), 0.99 (3H, s, H-27), 1.14 (3H, s, H-23), 2.93 (1H, d, J = 10.7, H-3), 3.63 (1H, d, J = 1.7, H-2), 5.23 (1H, d, J = 3.7, H-12) [11]. Methyl-α-D-fructofuranoside (5). White amorphous powder, C7H14O6. 1H NMR spectrum (300 MHz, CD3OD, δ, ppm, J/Hz): 3.27 (3H, s, MeO-2), 3.59 (1H, d, J = 12.0, H-1a), 3.68 (1H, d, J = 12.0, H-1b), 3.74 (1H, d, J = 2.9, H-6a), 3.80 (1H, m, H-6b), 3.82 (1H, m, H-5), 3.86 (1H, dd, J = 4.1, 6.4, H-4), 4.00 (1H, d, J = 4.1, H-3). 13C NMR spectrum (75 MHz, CD3OD, δ, ppm): 49.9 (MeO-2), 60.5 (C-1), 62.8 (C-6), 78.9 (C-4), 82.6 (C-3), 84.7 (C-5), 109.2 (C-2) [12]. Methyl-β-D-fructofuranoside (6). White amorphous powder, C7H14O6.H NMR spectrum (300 MHz, CD3OD, δ, ppm, J/Hz): 3.32 (3H, s, MeO-2), 3.50 (1H, d, J = 11.8, H-1a), 3.56 (1H, m, H-6a), 3.63 (1H, d, J = 11.8, H-1b), 3.70 (1H, m, H-6b), 3.74 (1H, m, H-5), 3.89 (1H, dd, J = 8.0, 5.6, H-4), 4.08 (1H, d, J = 8.0, H-3). 13C NMR spectrum (75 MHz, CD3OD, δ, ppm): 49.9 (MeO-2), 61.5 (C-1), 64.7 (C-6), 77.2 (C-4), 78.8 (C-3), 83.5 (C-5), 105.2 (C-2) [12].