Changhao Zhang

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.

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.

A new biflavonoid from the whole herb of Lepisorus ussuriensis

Abstract A new biflavonoid, 7-O-methylnaringenin-(4′→O→6″)-scutellarein (1), together with 11 known compounds (2–12) were isolated from the whole herb of Lepisorus ussuriensis. The structure of compound 1 was elucidated by spectroscopic analyses. Amongst them, dihydroquercetin (6), diosmetin (9), baicalein (11) and 7,8-dihydroxyflavone (12) were reported from the family Polypodiaceae for the first time. Meanwhile, quercetin (7), diosmetin (9) and luteolin (10) inhibited TNF-α-induced NF-κB reporter gene expression on HeLa cells up to 30 and 100 μM. Graphical abstract