Shepo Shi

Phenylethanoid glycosides with anti-inflammatory activities from the stems of Cistanche deserticola cultured in Tarim desert

Five new phenylethanoid glycosides, cistanosides J-N (1-5), together with 15 known ones (6-20) were isolated from the stems of Cistanche deserticola cultured in Tarim desert, China. Their structures were elucidated on the basis of extensive spectroscopic analysis (IR, HR-ESIMS, 1D- and 2D-NMR) and chemical degradation. All the compounds obtained were examined for their inhibitory effect on the lipopolysaccharide (LPS)-induced nitric oxide (NO) production in mouse microglial cells (BV-2 cells), and compounds 2 and 8 showed potent inhibition on the NO production with IC50 values of 14.94 μM and 14.32 μM, respectively.

Simultaneous characterisation of fifty coumarins from the roots of Angelica dahurica by off-line two-dimensional high-performance liquid chromatography coupled with electrospray ionisation tandem mass spectrometry.

INTRODUCTION The root of Angelica dahurica is a traditional Chinese medicine that used for the treatment of headache, toothache, abscess, furunculosis and acne. Coumarins were the major bioactive constituents of A. dahurica, hence it is worthwhile developing a method to simultaneously characterise them, especially those in trace amounts. OBJECTIVE To develop an efficient method for the simultaneous characterisation of coumarins in A. dahurica. METHODS A method using off-line two-dimensional high-performance liquid chromatography coupled with electrospray tandem mass spectrometry (off-line 2D-HPLC-ESI/MS(n) ) was developed. RESULTS In total 50 coumarins, including 32 linear furanocoumarins, 16 bifuranocoumarins and two non-furanocoumarins, were identified from the roots of A. dahurica. The possible MS fragmentations of these coumarins are also proposed. CONCLUSION The method described here allows rapid and convenient identification of the coumarins in A. dahurica, and may be applied to other herbal medicines containing linear furanocoumarins.

Anti-neuroinflammatory constituents from Polygala tricornis Gagnep

Two new compounds (S)-(+)-butyl-4-methylene-5-oxo-pyrrolidin-2-carboxylate (1) and (5-formylfuran-2-yl)methyl 4-hydroxy-2-methylenebutanoate (2), together with four known compounds (3-6) were isolated from the roots of Polygala tricornis Gagnep. Their structures were determined on the basis of 1D- and 2D-NMR experiments and by comparison with physical data of known compounds. All the isolated compounds were examined for their inhibitory effect on the nitric oxide (NO) production induced by lipopolysaccharide (LPS) in BV-2 microglial cells, and compounds 1 and 2 exhibited pronounced inhibition on the NO production with IC(50) values of 14.1 μM and 1.77 μM, respectively.

Coreosides A-D, C14-polyacetylene glycosides from the capitula of Coreopsis tinctoria and its anti-inflammatory activity against COX-2.

Four new C14-polyacetylene glycosides, namely coreosides A-D (1-4), were isolated from the capitula of Coreopsis tinctoria, a Snow chrysanthemum or Snow tea that is used as a folk tea for prevention of cardiovascular disease in southern Xinjiang, China. Coreosides A-D feature a long chain structure as its aglycon with two acetylenes on C-8 and C-10 and two olefinics on C-6 and C-12 sites, which construct a large conjugate system. The structures were elucidated on the basis of spectroscopic evidences and hydrolysis. Compounds 1-4 exhibited significant inhibition against cyclooxygenase-2 at the concentration of 1×10(-6) mol/L, with its IC50 values of 0.22-8.8×10(-2) μmol/L.

Homolog-focused profiling of ginsenosides based on the integration of step-wise formate anion-to-deprotonated ion transition screening and scheduled multiple reaction monitoring

Homolog-focused profiling is a favored option to bridge targeted metabolomics toward non-targeted metabolomics. In current study, an attempt was made for the large-scale ginsenoside-specific analysis in ginseng (G) and American ginseng (AG). When formic acid (0.1%, v/v) was introduced as the mobile phase additive, formate anion-to-deprotonated ion transitions ([M+HCOO](-)>[M-H](-)) with an optimal collision energy (-32eV) could result in satisfactory responses for ginsenosides. Therefore, a step-wise multiple reaction monitoring (MRM)-based method employing [M+HCOO](-)>[M-H](-) ion pairs was constructed to screen ginsenosides among 501-1250u (for Q1) with a step-size of 2u, and MRM also served as a survey experiment to trigger enhanced product ion scans for MS(2) spectrum acquisition on a hybrid triple quadrupole-linear ion trap mass spectrometer; then, the identification of those observed ginsenosides was achieved on the basis of the well-defined mass cracking patterns for ginsenosides; afterwards, scheduled MRM was introduced for large-scale relatively quantitative analysis of all detected ginsenosides. Finally, comparative metabolomics were performed to differentiate G, AG, and their processed products. Method validation was carried out using thirteen authentic compounds. A total of 221 ginsenosides, among which 185 ones were annotated, were observed and relatively quantitated. All crude materials were obviously classified into groups I-III. Above all, the MRM-based homolog-focused profiling of ginsenosides could be used as a reliable tool to gain an in-depth view for ginsenoside-enriched herbal products.

Quinolone alkaloids with antibacterial and cytotoxic activities from the fruits of Evodia rutaecarpa.

Five new quinolone alkaloids, euocarpines A-E (16-20), four new natural products (1, 4, 12, and 14), and eleven known natural products were isolated from the fruits of Evodia rutaecarpa (Juss.) Benth. The structures of the new compounds were elucidated based on spectroscopic evidence. All compounds were evaluated for their antibacterial activity against three strains and for their cytotoxic activity against four human tumor cell lines. The results revealed that 5, 7-11, 13, 14, and 16-20 exhibited moderate antibacterial activities (MIC values: 4-128 μg/mL), and 9, 11, 14, and 17 exhibited moderate cytotoxic activities against HepG-2, Hela, BEL7402, and BEL7403 (IC50 values: 15.85-56.36 μM).

Simultaneous determination of aconite alkaloids and ginsenosides using online solid phase extraction hyphenated with polarity switching ultra-high performance liquid chromatography coupled with tandem mass spectrometry

Aconite alkaloids and ginsenosides have been demonstrated as the effective constituents in Shenfu injection (SFI), which is a widely used Chinese herbal formulation prepared from red ginseng and processed aconite root. Quality control is quite critical to meet the increasing demand of SFI in the market and to guarantee safety in clinics, in particular regarding the toxic aconite alkaloids. Given the significant merits of online solid phase extraction (SPE) for sample preparation, an online SPE-based method was developed to simultaneously quantify ten aconite alkaloids and thirteen ginsenosides in SFI using UHPLC-MS/MS. Because of their distinct ionization behaviors, polarity switching was implemented in the ion source domain with a scheduled program, and positive and negative ionization modes were applied for alkaloids and saponins, respectively. Quantitative terms of the proposed method with respect to linearity, limit of detection, lower limit of quantification, precision, and accuracy were evaluated, and the results indicated that the method is sensitive, convenient, and reliable. The developed method was successfully applied for the simultaneous determination of aconite alkaloids and ginsenosides in ten batches of SFI (SFI1-10). The validated method can be adopted as a meaningful tool for the quality control of SFI concerning aconite alkaloids and ginsenosides, and also it offers a reliable choice for the widely qualitative analysis of constituents in complex matrices being free from tedious sample preparation procedures.

Anti-inflammatory dimeric furanocoumarins from the roots of Angelica dahurica.

Seven new dimeric furanocoumarins, dahuribiethrins A-G (1-7), were isolated from the roots of Angelica dahurica. Their structures were determined by chemical derivatization and extensive spectroscopic techniques, including (1)H NMR, (13)C NMR, HSQC, (1)H-(1)H COSY, HMBC, and NOESY experiments. Compounds 2, 3, 4, and 5 exhibited significant inhibition of nitric oxide production in the lipopolysaccharide (LPS)-stimulated RAW264.7 macrophage cells with IC50 values in the range of 8.8-9.8 μM.

Anti-neuroinflammatory sesquiterpenes from Chinese eaglewood.

Nine new sesquiterpenes (1-9), together with seventeen known ones (10-26), were isolated from Chinese eaglewood. Their structures were established by extensive spectroscopic analysis, and the absolute configuration of 6 was determined by the modified Moshers method. Compounds 7, 10, 14, 15, and 21 exhibited significant inhibition of nitric oxide production in lipopolysaccharide-stimulated BV-2 microglial cells with IC50 values in the range 7.1-53.8 μM.

Anti-inflammatory 2-(2-phenylethyl)chromone derivatives from Chinese agarwood.

Five new 2-(2-phenylethyl)chromone derivatives (1-5), along with eleven known compounds (6-16) were isolated from Chinese agarwood. Their structures were elucidated by spectroscopic data (NMR, UV, IR, and MS) analyses and comparison of their spectroscopic and physical data with the literature values. The absolute configurations of 2-4 were determined by electronic circular dichroism (ECD) calculations. Compounds 2-4, 11, 12, and 15 exhibited significant inhibition of nitric oxide production in lipopolysaccharide-stimulated RAW 264.7 cells with IC50 values in the range 1.6-7.3μM.