Shi-Lin Yang

Lomatogonium rotatum (L.) Fries ex Nym (LR) is used as a traditional Mongolian medicine to treat liver and bile diseases. This study aimed to investigate the hepatoprotective effect of LR on mice with CCl₄-induced acute liver injury through conventional assays and metabolomics analysis. This study consisted of male mice (n = 23) in four groups (i.e., control, model, positive control, and LR). The extract of whole plant of LR was used to treat mice in the LR group. Biochemical and histological assays (i.e., serum levels of alanine transaminase (ALT) and aspartate transaminase (AST), and histological changes of liver tissue) were used to evaluate LR efficacy, and metabolomics analysis based on GC-MS and LC-MS was conducted to reveal metabolic changes. The conventional analysis and metabolomic profiles both suggested that LR treatment could protect mice against CCl₄-induced acute liver injury. The affected metabolic pathways included linoleic acid metabolism, α-linolenic acid metabolism, arachidonic acid metabolism, CoA biosynthesis, glycerophospholipid metabolism, the TCA cycle, and purine metabolism. This study identified eight metabolites, including phosphopantothenic acid, succinic acid, AMP, choline, glycerol 3-phosphate, linoleic acid, arachidonic acid, and DHA, as potential biomarkers for evaluating hepatoprotective effect of LR. This metabolomics study may shed light on possible mechanisms of hepatoprotective effect of LR.

Seven acylated triterpene saponins were isolated from the roots of Securidaca inappendiculata by means of various chromatographic techniques such as silica gel, MPLC, preparative HPLC, and semi-preparative HPLC. Their chemical structures were identified as securioside A(1), securioside B(2), 3-O-β-D-glucopyranosyl presenegenin 28-O-β-D-xylopyranosyl-(1-->4)-α-L-rhamnopyranosyl-(1-->2)-[β-D-glucopyranosyl-(1-->3)]-4-O-[(E)-3,4-dimethoxycinnamoyl]-β-D-fucopyranosyl ester(3), 3-O-β-D-glucopyranosyl presenegenin 28-O-β-D-xylopyranosyl-(1-->4)-α-L-rhamnopyranosyl-(1-->2)-[β-D-glucopyranosyl-(1-->3) ] -4-O-[(E/Z)-3, 4-dimethoxycinnamoyl]-β-D-fucopyranosyl ester(3/4), 3-O-β-D-glucopyranosyl presenegenin 28-O-α-L-arabinopyranosyl-(1-->3)-β-D-xylopyranosyl-(1-->4)-α-L-rhamnopyranosyl-(1-->2)-4-O-[(E)-3,4-dimethoxycinnamoyl]-β-D-fucopyranosyl ester(5), polygalasa- ponin XLV(6), and polygalasaponin XLVI (7) on the basis of spectroscopic data analysis and physicochemical properties. Among them, compounds 5-7 were isolated from the plants in genus Securidaca for the first time and compounds 3, 3/4 were isolated from the species for the first time. The cytotoxicity assay showed that compounds 2, 3/4, 5 have moderate cytotoxic activities against Lewis lung carcinoma LLC cells with IC50 values of 41.10, 38.17, and 48.92 µmol · L(-1), respectively; compound 2 exhibited moderate cytotoxic activities against human breast cancer MCF-7 cells with an IC50 value of 47.93 µmol · L(-1).

To study the chemical constituents of the stems of Clematis parviloba, six compounds were isolated from a 95% ethanol extract by using a combination of various chromatographic techniques including column chromatography over silica gel, ODS, Sephadex LH-20, and semi-preparative HPLC. Two new phenolic glycosides, 2-((E)-3-carboxybut-2-en-yl)-4-hydroxy-3-methyl-phenyl-O-beta-D-glucopyranoside (1) and 4'-hydroxy-phenol-beta-D-[6-O-(4"-hydroxy-3", 5"-dimethoxy-benzoate)] glucopyranoside (2) were isolated, together with a known phenolic glycoside, 4'-hydroxy-3'-methoxy-phenol-beta-D-[6-O-(4"-hydroxy-3", 5"-dimethoxy-benzoate)] glucopyranoside (3) as well as three known megastigmane glycosides, linarionoside A (4), linarionoside C (5), and staphylionoside K (6). Their structures were determined on the basis of spectroscopic analysis and chemical evidence. Among them, compounds 1 and 2 were named as clemaparvilosides A (1) and B (2), respectively, and compounds 3-6 were obtained from Clematis genus for the first time.

To isolate and identify chemical constituents of Cassia alata. Compounds were separated and purified by column chromatography with silica gel and Sephadex LH-20, elucidated by spectroscopic methods including 1D and 2D NMR, IR and MS techniques. Twelve compounds were isolated from C. alata, which were identified as chrysoeriol (1), kaempferol (2), quercetin (3), 5,7,4'-trihydroflavanone (4), kaempferol-3-O-beta-D-glucopyranoside (5), kaempferol-3-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranoside (6), 17-hydrotetratriacontane (7), n-dotriacontanol (8), n-triacontanol (9), palmitic acid ceryl ester (10), stearic acid (11), palmitic acid (12). Compounds 3-12 were isolated from C. alata for the first time.

Sixteen triterpenoid saponins (1–16) were isolated from the stems of Clematis parviloba, including a new compound, parvilobaside A (1), which was established as 23-O-acetyl-hederagenin-3-O-β-d-ribopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranoside on the basis of various spectroscopic techniques and chemical evidences. Among the isolated compounds, clematoside S (2) and α-hederin (4) showed moderate cytotoxic activities against four human tumor cell lines (HCT-8, Bel-7402, BGC-823, and A-2780) with IC₅₀ values in the range of 1.44–6.86 μg/ml.

To study the chemical constituents of the stems of Clematis parviloba. The compounds were isolated and purified by repeated column chromatography with silica gel, Sephadex LH-20 and HPLC. Their structures were identified by spectroscopic data together with physical and chemical property. Ten compounds have been isolated from the stems of C. parviloba, and identified as: (+) pinoresionol (1), (+) pinoresionol-4'-O-p-D-glucopyranoside (2), ( +) pinoresionol4, 4'-O-bis-beta-D-glucopyranoside (3), (-) syringaresinol (4), (+) syringaresinol-4'-O-beta-D-glucopyranoside (5), (-)episyringaresinol (6), (+) medioresinol-4'-O-beta-D-glucopyranoside (7), (+) lariciresinol-4-O-beta-D-glucopyranoside (8), (+) lariciresinol-4'-O-beta-D-glucopyranoside (9), (+) lariciresinol-4, 4'-O-bis-beta-D-glucopyranoside (10), respectively. Compounds 6, 7 were isolated from this genus for the first time, and the other ones were isolated from this plant for the first time.

Eighteen different triterpene saponins isolated from Polygala tenuifolia were investigated by electrospray ionization ion trap multiple‐stage mass spectrometry (ESI‐ITMSⁿ) in positive and negative ion modes. MS¹‐MS³/MS⁴ spectra of the both modes were analyzed, and they all gave fragments in line and shared common fragmentation patterns. Key fragments from MSⁿ spectra of both the modes and their proposed fragmentation pathways were constructed with examples illustrated for the formation of characteristic fragments in the saponins. Two special fragmentation patterns were proposed: (1) the formation of fragments by cleavage of CH₂O from Δ¹²‐14α‐CH₂OH of the oleanene‐type saponin aglycone in both positive and negative MSⁿ (n ≥ 2) modes; (2) the occurrence of fragments by cleavage of CO₂ and 3‐glucose as the characteristic structure feature of 23‐COOH at the oleanene‐type saponin aglycones coupled with 3‐Glc substitutes in the negative MSⁿ (n ≥ 2) modes. Peak intensities in MSⁿ spectra were also correlated with structural features and fragmentation preferences of the investigated saponins, which are discussed in detail. In general, fragments formed predominantly by cleavages of glycosidic bonds in the positive mode, while selective cleavages of acyl bonds preceded that of glycosidic bonds in negative MSⁿ (n ≥ 2) mode, both of which could well be applied to the structural analysis of these saponins. Interpretation of MSⁿ spectra presented here provided diagnostic key fragment ions important for the structural elucidation of saponins in P.tenuifolia. Copyright © 2007 John Wiley & Sons, Ltd.