Long-Ping Zhu

Structural characterization and anti-fatigue activity of polysaccharides from the roots of Morinda officinalis

Three polysaccharides MP-1, MP-2, and MP-3 were isolated from hot water extract of Chinese medicine Morinda officinalis through 95% ethanol precipitation and gel-filtration chromatography (DEAE-Sepharose CL-6B column and Sephadex G-75 or G-100 column). MP-1 was identified as an inulin-type fructan with simple linear (2-->1)-linked structure. Both MP-2 and MP-3 were acidic polysaccharides which consisted predominantly of galacturonic acid, arabinose and galactose. Partial structure characterization of MP-3 was carried out by partial acid hydrolysis and periodate oxidation. The total polysaccharides of the herb were tested in mice weight-loaded swimming model and were found to have anti-fatigue activity.

Thin-layer chromatographic identification of Chinese propolis using chemometric fingerprinting.

INTRODUCTION Poplar tree gum has a similar chemical composition and appearance to Chinese propolis (bee glue) and has been widely used as a counterfeit propolis because Chinese propolis is typically the poplar-type propolis, the chemical composition of which is determined mainly by the resin of poplar trees. The discrimination of Chinese propolis from poplar tree gum is a challenging task. OBJECTIVE To develop a rapid thin-layer chromatographic (TLC) identification method using chemometric fingerprinting to discriminate Chinese propolis from poplar tree gum. METHODS A new TLC method using a combination of ammonia and hydrogen peroxide vapours as the visualisation reagent was developed to characterise the chemical profile of Chinese propolis. Three separate people performed TLC on eight Chinese propolis samples and three poplar tree gum samples of varying origins. Five chemometric methods, including similarity analysis, hierarchical clustering, k-means clustering, neural network and support vector machine, were compared for use in classifying the samples based on their densitograms obtained from the TLC chromatograms via image analysis. RESULTS Hierarchical clustering, neural network and support vector machine analyses achieved a correct classification rate of 100% in classifying the samples. A strategy for TLC identification of Chinese propolis using chemometric fingerprinting was proposed and it provided accurate sample classification. CONCLUSION The study has shown that the TLC identification method using chemometric fingerprinting is a rapid, low-cost method for the discrimination of Chinese propolis from poplar tree gum and may be used for the quality control of Chinese propolis.

Diterpenoids from aerial parts of Flickingeria fimbriata and their nuclear factor-kappaB inhibitory activities.

Chemical investigation of the aerial parts of Flickingeria fimbriata (Bl.) Hawkes resulted in isolation of sixteen ent-pimarane diterpenoids, including five rare 16-nor-ent-pimarane diterpenoids, two 15,16-dinor-ent-pimarane diterpenoids and one ent-pimarane diterpenoid. Structures were mainly elucidated by extensive spectroscopic analysis, and their absolute configurations were unequivocally determined by the exciton chirality method, the modified Moshers method, the CD experiments (including Snatzkes method) and chemical transformations, respectively. All the isolated compounds were screened for inhibitory effects on the nuclear factor-kappaB (NF-κB) in lipopolysaccharide (LPS) induced murine macrophage RAW264.7 cells, using a NF-κB-dependent luciferase reporter gene assay. Several of these compounds displayed comparable or even better activities than the positive control pyrrolidinedithiocarbamate (PDTC) (IC50=26.3 μM) with IC50 values in the range of 14.7-29.2 μM and structure-activity relationships are briefly proposed.

Chlojaponilactone B from Chloranthus japonicus: Suppression of Inflammatory Responses via Inhibition of the NF-κB Signaling Pathway

Bioassay-guided fractionation of an ethanolic extract of Chloranthus japonicus led to the isolation of the known lindenane-type sesquiterpenoid chlojaponilactone B (1). This compound exhibited pronounced inhibition of nitric oxide (NO) production in lipopolysaccharide (LPS)-induced RAW 264.7 macrophages. Further anti-inflammatory assays showed that 1 suppressed the levels of some key inflammation mediators, such as iNOS, TNF-α, and IL-6, in a dose-dependent manner, and reduced the ear thickness and neutrophil infiltration in 12-O-tetradecanoylphorbol-13-acetate (TPA)-stimulated mice. A mechanistic study revealed that compound 1 exerted its anti-inflammatory effects via the suppression of the NF-κB signaling pathway, which inhibited NF-κB-dependent transcriptional activity, IκBα phosphorylation, and p65 nuclear translocation. In contrast, chlojaponilactone B (1) was found to exert little influence on the MAPK signaling pathway.

Bioactive norditerpenoids from Flickingeria fimbriata

Seven new degraded diterpenoids (1–6 and 11), four new ent-pimarane type diterpenoids (7–10) and a known analogue (12) were isolated from the stem of Flickingeria fimbriata. Compounds 1–4, namely norflickinflimiods A–D, possessed a rare 16-nor-ent-pimarane skeleton, and 5–6, namely norflickinflimiods E and F, represented an unusual skeleton of 15,16-dinor-ent-pimarane. The structures including the absolute configurations of 1–12 were elucidated using spectroscopic analysis, single-crystal X-ray diffraction, computational methods, and chemical correlations. All the isolates were screened for anti-inflammatory and antitumor activities, and compounds 5, 6, 9, and 12 showed potent inhibitory activities against lipopolysaccharide (LPS)-induced TNF-α production in RAW264.7 cells with IC50 values less than 10 μM, while compounds 8–11 exhibited cytotoxicity against MCF-7 cells (9.6, 9.0, 12.0, and 15.6 μM).

Solidification of floating organic drop liquid-phase microextraction cell fishing with gas chromatography–mass spectrometry for screening bioactive components from Amomum villosum Lour

In this study, a novel solidification of floating organic drop liquid-phase microextraction cell fishing with gas chromatography-mass spectrometry (SFOD-LPME-CF-GC-MS) method was established and used to screen, isolate and analyze bioactive components from Amomum villosum Lour. extract. Through comparision of its effect on the models of normal cell and inflammatory cells, anti-inflammatory active components of essential oil from A. villosum Lour. were readily screened, and the components obtained are in agreement with related pharmacological articles. SFOD-LPME-CF-GC-MS was used to analyze the interaction of A. villosum Lour. extracts with normal and lipopolysaccharide-stimulated RAW264.7 macrophage cells. The effect of A. villosum Lour. essential oil extracts in the LPS-stimulated RAW264.7 model were also assessed in terms of cytotoxicity and nitric oxide production as an indication of bioactivity. Three potentially bioactive components were identified, demonstrating that SFOD-LPME-CF-GC-MS can be used successfully in the drug-screening process. This approach avoids the requirement for protein precipitation, but more importantly, generates a high concentration ratio, allowing analysis of trace components in traditional Chinese medicines. SFOD-LPME-CF-GC-MS is a simple, fast, effective and reliable method for the screening and analysis of bioactive components, and it can be extended to screen other bioactive components from TCMs.

Two new glycosides isolated from Sapindus mukorossi fruits: effects on cell apoptosis and caspase-3 activation in human lung carcinoma cells

Two new glycosides (1, 2) and two saponins (3, 4) were isolated from the fruits of Sapindus mukorossi Gaertn. The two glycosides were designated as sapindoside G (1) and 4′′,4′′′′′-O-diacetylmukurozioside IIa (2). All four compounds exhibited inhibitory effects against A549 human lung adenocarcinoma cells with inhibition rates up to 69.2–83.3% at a concentration of 100 μg/mL. Flow cytometric analysis revealed that compounds 1–4 could suppress A549 cell growth by promoting cell apoptosis, which was related to the activation of caspase-3. Graphical abstract

ISOLATION AND PURIFICATION OF FOUR BIOACTIVE CONSTITUENTS FROM Alpinia officinarum HANCE UTILIZING HIGH-SPEED COUNTER-CURRENT CHROMATOGRAPHY

Galangal, the rhizome of Alpinia officinarum Hance (Chinese pinyin name: Gao-liang-jiang), is one of the most popular Chinese herbs that has extensive pharmacological effects. In this study, a high-speed counter-current chromatography (HSCCC) method has been used for the first time to separate key bioactive chemical constituents from galangal. Four compounds including 5 R-hydroxy-7-(4-hydroxy-3-methoxyphenyl)-1-phenyl-3-heptanone, kaempferol-4′-methylether, galangin, and 7-(4-hydroxy-3-methoxyphenyl)-1-phenyl-4E-en-3-heptanone were obtained from the chloroform extract of galangal using HSCCC. Their structures were identified by ESI-MS, 1H NMR, and 13C NMR. The study showed the value of orthogonal selectivity in liquid–liquid chromatography with references to an example of superior resolution in preparative HSCCC as compared to analytical HPLC, where it baseline-resolved two components that co-eluted with analytical reverse phase HPLC assay. The study also showed examples of the considerable resolution choices offered by different biphasic solvent systems.

A new triterpenoid saponin and an oligosaccharide isolated from the fruits of Sapindus mukorossi

A new triterpenoid saponin (1) and a new oligosaccharide (2), together with three known saponins (3–5), have been isolated from n-BuOH extract of the fruits of Sapindus mukorossi Gaertn. The structures were elucidated using detailed analysis of one- and two-dimensional nuclear magnetic resonance spectra along with their mass spectrometric data and the results of acid hydrolysis. Of the isolated compounds 1 and 3–5 displayed cytotoxic effects against human cancer cell lines in A-549 (lung carcinoma), MDA-231 (breast carcinoma) and PC-3 (prostatic carcinoma).

Three new cassane diterpenes from the seeds of Caesalpinia minax Hance

Abstract Four fractions were prepared from the crude extract of Caesalpinia minax Hance and the inhibitory activity of nitric oxide (NO) production release of RAW 264.7 cells stimulated by lipopolysaccharide (LPS) was evaluated. The ethyl acetate (EtOAc) fraction showed obvious inhibitory effect. Bioassay-guided fractionation led to the isolation of three new cassane diterpenes, caesalmin X (1), caesalmin Y (2) and caesalmin Z (3), together with 19 known cassane diterpenoids (4–22). Their structures were mainly characterised on the basis of extensive spectroscopic analyses and comparison with reported data. Moreover, three compounds (20–22) which possessed furanditerpenoid 7,17-lactone structures, displayed moderate activities, with IC50 value of 29.85, 27.38 and 25.40 μM, respectively.