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Successful isolation of 15 compounds from Polygonti rhizome was obtained by an efficient technique combined with macroporous resin column chromatography pretreatment and three different modes of high-speed counter-current chromatography for the first time. For the pretreatment, AB-8 resin was applied to remove the polysaccharides and enrich four different parts (samples I, II, III, and IV) by polarities. For the separation, sample I was separated by pH-zone-refining counter-current chromatography and seven cycle recycling mode high-speed counter-current chromatography, yielding four alkaloids (1--4); samples II-IV were further separated by the conventional high-speed counter-current chromatography, yielding seven flavonoids (5-10, 12), one steroid saponin (11), and three terpenoids (13-15). Finally, the isolates were assayed for their anti-inflammatory activities against nitric oxide production with compounds 5, 9-10, 13 showing significant anti-inflammatory activities, IC

Three undescribed cembrane type diterpenoids, boscartins AX-AZ (1-3) were discovered from the gum resin of Boswellia carterii. Their structures were elucidated by analyzing the spectroscopic data. Notably, all these three compounds preserved an isopropyl type cembranoid skeleton, featured the same groups of one epoxy ring at C1-C12 and one hydroxy group at C-11, as well as an epoxy ring migrating from C6-C7 to C3-C4. These cembranoids were evaluated for the hepatoprotective and anti-inflammatory activities using two cell models of APAP-induced HepG2 and LPS-induced RAW 264.7. Results showed that compound 1 displayed remarkable hepatoprotective activity at 10 μM (inhibition rate of 47.81 %) and significant anti-inflammatory activity (IC50 of 2.39 μM), with the other two compounds (2 and 3) giving less potently biological activities.

Four new isolates including one new butanediamide glycoside (

Four new cycloartane triterpenoids (1-4) were isolated from the leaves of Dysoxylum binectariferum. Their structures were elucidated on the basis of HRMS and NMR spectroscopic data. Compounds 1-3 represent a class of rare natural 24,25,26,27-tetranor type cycloartane triterpenoids. Compound 3 displayed moderate cytotoxicity against HCT-116 and DLD-1 with IC50 values of 9.8 ± 0.3 μM and 12.0 ± 0.4 μM, respectively. Compound 4 showed moderate activitiy against HCT-116 with IC50 value of 12.1 ± 0.4 μM. Annexin V-PE/7-ADD staining assay indicated that 3 induced apoptosis in HCT-116 cells. This is the first report on discovery of degraded cycloartane triterpenoids from genus Dysoxylum.

Leaves of custard apple are widely used in many places as a popular dietary supplement for the treatment of diabetes. Flavonoids are known to have anti-diabetic activity. In this study, the main flavonoid epimers were separated. The crude extract was first screened by HPLC-DAD before and after incubation with DPPH method to evaluate the antioxidants. An efficient extraction method was employed to remove non-flavonoid components. Subsequently, five main flavonoids with two pairs of epimers including quercetin-3-O-robinobioside, rutin, quercetin-3-O-β-D-glucoside, kaempferol-3-O-robinobioside, and kaempferol-3-O-rutinoside were successfully separated by high-speed counter-current chromatography with ethyl acetate/n-butanol/water (4:1:5, v/v) coupled with online-storage inner-recycling mode. The structures of the separated compounds were identified by spectral techniques. The purity of the separated flavonoid glycosides was over 98%, as determined by HPLC. The separated pure constituents were found to possess the antioxidant capacities following DPPH radical scavenging protocol. The compounds (1-3) exhibited better antioxidant activity. Furthermore, the glucose uptake of crude flavonoid extract had better results than the crude ethanol extract. The present study demonstrates that the efficacy of custard apple leaves in lowering glucose level, and antioxidant capacities of separated pure compounds probably appear to be predominantly responsible for hypoglycaemic properties on HepG2 cells.

New insights into tumor-associated metabolic reprogramming have provided novel vulnerabilities that can be targeted for cancer therapy. Here, we propose a mass spectrometry imaging (MSI)-based metabolomic strategy to visualize the spatially resolved reprogramming of carnitine metabolism in heterogeneous breast cancer. Methods: A wide carnitine coverage MSI method was developed to investigate the spatial alternations of carnitines in cancer tissues of xenograft mouse models and human samples. Spatial expression of key metabolic enzymes that are closely associated with the altered carnitines was examined in adjacent cancer tissue sections. Results: A total of 17 carnitines, including L-carnitine, 6 short-chain acylcarnitines, 3 middle-chain acylcarnitines, and 7 long-chain acylcarnitines were imaged. L-carnitine and short-chain acylcarnitines are significantly reprogrammed in breast cancer. A classification model based on the carnitine profiles of 170 cancer samples and 128 normal samples enables an accurate identification of breast cancer. CPT 1A, CPT 2, and CRAT, which are extensively involved in carnitine system-mediated fatty acid β-oxidation pathway were also found to be abnormally expressed in breast cancer. Remarkably, the expressions of CPT 2 and CRAT were found for the first time to be altered in breast cancer. Conclusion: These data not only expand our understanding of the complex tumor metabolic reprogramming, but also provide the first evidence that carnitine metabolism is reprogrammed at both the metabolite and enzyme levels in breast cancer.

The roots of Dipsacus asper Wall as a commonly used traditional Chinese medicine are used for tonifying liver and kidney and strengthening bones and muscles. However, an effective separation strategy for comprehensive and rapid separation of the main active compounds from the roots of D. asper is nonexistent. This investigation provided an effective separation method based on AB-8 macroporous resin column chromatography using different ratios of ethanol in water and two different modes of high-speed countercurrent chromatography with salt-containing solvent system for rapid enrichment and separation from the roots of D. asper. The macroporous resin column chromatography was performed on AB-8 resin using ethanol in water ratios of 10, 30, 40, 50, and 80% as the optimized enrichment conditions for iridoid glycosides and triterpenoid saponins with different polarities. For high-speed countercurrent chromatography separation, the conventional and recycling modes were combined together to develop a strategy for 12 compounds (1-12) from the enriched parts of 30, 40, and 80% ethanol, including six high-polarity iridoid glycosides (1-6) using inorganic salt-containing solvent system and six triterpenoid saponins (7-12). Recycling high-speed countercurrent chromatography separation was successfully applied to separate two isomers (9 and 10) after 11 cycles.

Eight new cembrane-type diterpenoids, boscartins AH–AK (1–8), along with two known ones (9-10), were isolated from the gum resin of Boswellia carterii. Compounds 1–3 were characteristic of high oxidation assignable to three epoxy groups, while compounds 4–8 were characteristic of two epoxy groups. Spectroscopic examination was used to elucidate their structures. All isolates were evaluated for antiproliferative activity against HCT-116 human colon cancer cells, anti-inflammatory activity against nitric oxide (NO) production, and hepatoprotective activity in vitro. All of them showed weak antiproliferative activity (IC50 > 100 μM), 8 exhibited potent inhibitory effects on NO production (IC50 of 14.8 μM), with the others showing weak anti-inflammatory activity (IC50 > 30 μM), and 1 exhibited more potent hepatoprotective activity than the positive control, bicyclol, at 10 μM against the damage induced by paracetamol in HepG2 cells.

Four new isolates including one new butanediamide glycoside (1), one new flavonoid glycoside (2) and two new flavonone glycosides (3, 4) were identified from the leaves and stems of Panax quinquefolius, among which 1 possessed the firstly reported N,N'-(5-hydroxy-1,3-phenylene) butanediamide skeleton with an unique 6/9 ranged dual-ring structure. The structures were elucidated by the NMR data, ECD analysis and chemical acid hydrolysis. All the compounds (1-4) were tested for their cytotoxicity against two human cancer cell lines of HepG2, A549 and HCT116 by the MTT method. Outstandingly, compound 1 exhibited targeted inhibitory proliferation of HCT116 cell with IC50 value of 12.1 μM, whereas compounds 3 and 4 exhibited targeted inhibitory proliferation of HepG2 cell with IC50 values of 15.3 and 17.3 μM, as well as no obvious cytotoxicity of compounds 1-4 against A549.

Five undescribed cembranoid alcohols, boscartinols A-E (1–5) were discovered from the gum resin of Boswellia carterii. Their structures were elucidated by analyzing the spectroscopic data. Notably, all these five compounds preserved an isopropyl type cembranoid skeleton, featured the same groups of one epoxy ring at C1-C12 and one hydroxy group at C-11, as well as two double bonds migrating from C3 to C9 and one hydroxy group from C3 to C8 within the cembranoid structure. These cembranoids were evaluated for the hepatoprotective and anti-inflammatory activities using two cell models of APAP-induced HepG2 and LPS-induced RAW 264.7. For hepatoprotective activity, compounds 1 and 5 showed remarkable hepatoprotective activity (inhibition rate of 51.6% and 39.8%, respectively) at 10 μM, with the other three compounds of 2–4 showing less potently hepatoprotective. For anti-inflammatory activity, compounds 2–4 showed significant inhibitory effects on NO produced by LPS-induced RAW 264.7 cell (IC50 values of 13.40 μM, 7.08 μM and 14.26 μM), with the other two compounds of 1 and 5 showing less potently anti-inflammatory activities.

Six new isolates including three new alkaloids (1-3), one new secoiridoid glycoside (4) and one new 11-delactonization-secoiridoid glycoside (5), and one new organic acid (6) were identified from the leaves of Lonicera japonica, among which 1 and 2 assigned as a pair of configurational isomers possessed two oxazolidin-2-one fragments connected through NN bond. The structures were elucidated by the NMR data and ICD analysis. All the compounds (1-6) were tested for their antioxidant and hepatoprotective activities using cell models of ABAP-induced HepG

Pb2+ pollution and poisoning are serious environmental and pharmacological concerns. The World Health Organization reported that Pb has resulted in 540,000 deaths in 2016 alone. Therefore, effective drugs or supplements that can alleviate or offset Pb2+-induced toxicity are badly needed. Through screening biocompatible natural compounds, we discovered that chicoric acid exhibited potent protective activities against Pb2+-induced toxicity both in BV-2 microglial cells and in zebrafish from the first days of development. Chicoric acid was able to reduce Pb2+-induced increases in levels of reactive oxygen species and tumor necrosis factor alpha, restoring the cell cycle in BV-2 cells. In the zebrafish model, chicoric acid significantly alleviated the Pb2+-induced serious mortality and malformation of zebrafish larvae in a concentration-dependent manner. These protective activities of chicoric acid were mainly from its alleviation of Pb2+-induced dysregulation of oxidative response pathways, including key genes such as Aox1, Gclm, Hmox1, Nqo1, Scd1, and Srxn1, as well as HO-1 protein. Since Pb2+ is difficult to be completely eliminated from the body and chelating agents may cause serious adverse effects, chicoric acid is likely a potential supplement therapy, in addition to current clinical practices.

A novel bioreactor with high-speed counter-current chromatography (HSCCC) was established for the efficient biotransformation of isoflavone aglycones from soybeans. Further, the transformed isoflavone aglycones were separated by HSCCC with continuous injection mode. β-Glucosidase and snailase were chosen as the optimum enzymes for HSCCC bioreactor biotransformation. Compared with snailase, β-glucosidase showed the advantages in both enzymatic hydrolysis efficiency and the influence to retention of the stationary phase and 4 mL/min were selected as the optimum elution flow-rate. The transformed isoflavone aglycones were separated by HSCCC with a solvent system n-hexane/ethyl acetate/ethanol/water (1:1.6:1:1.6, v/v). From 200 mg crude samples, 82 mg of daidzein, 48 mg of glycitein and 24 mg of genistein were separated with purities over 95%, respectively, as determined by HPLC. The chemical structures of these compounds were identified by EI-MS and 1H-NMR. Our results suggest that HSCCC could be developed as a bioreactor in the preparation of isoflavone aglycones from soybeans for the facility to immobilize and recycle the enzyme.

Three flavonoid glycosides and four flavonoid aglycones were isolated and purified for the first time from the leaves of Platycladus orientalis via two different elution modes of high-speed counter-current chromatography. First, the fractions containing the flavonoid glycosides and flavonoid aglycones were obtained via polyamide column chromatography to remove the nonflavonoids; afterwards, a reverse-inlet (REV-IN) elution mode was applied to purify the flavonoid glycosides using a two-phase solvent system composed of ethyl acetate–ethanol–acetic acid–water (4 : 1 : 0.25 : 5, v/v); then, a forward-inlet (FWD-IN) elution mode was applied to purify the flavonoid aglycones with a two-phase solvent system composed of chloroform–methanol–water (4 : 3 : 2, v/v). In total, three flavonoid glycosides, myricetrin (1, 10.2 mg), quercetin-3-O-α-L-rhamnoside (2, 25.8 mg), and kaempferol-3-O-α-L-rhamnoside (3, 9.3 mg), and four flavonoid aglycones, quercetin (4, 10.5 mg), kaempferol (5, 4.5 mg), amentoflavone (6, 13.8 mg) and myricetin (7, 14.7 mg), were successfully obtained from the enriched fractions of flavonoid glycoside and flavonoid aglycone by the REV-IN mode HSCCC and FWD-IN mode HSCCC, respectively, structures of which were elucidated by HR-ESI-MS and 1H and 13C NMR spectroscopy. The results demonstrate that the combination of polyamide column chromatography and HSCCC is effective for the rapid enrichment and separation of flavonoid glycosides and flavonoid aglycones from the leaves of P. orientalis.

An efficient method for the preparative separation and isolation of ginkgolic acids (GAs) from the sarcotesta of Ginkgo biloba L was developed by combining pH-zone-refining counter-current chromatography (PZRCCC) with inner-recycling mode. Two grams of GAs extract were separated by PZRCCC using a two-phase solvent system of n-heptane–ethyl acetate–methanol–water (2:1:3:1, v/v) with 10 mM HCl added to the upper phase as the retention acid and 10 mM triethylamine (TEA) in the lower phase as the elution base. In a one-step PZRCCC separation, two GA compounds, C15:1 and C17:2, were obtained with purities over 98% along with two mixtures. The mixtures were further separated by inner-recycling CCC mode with n-heptane–ethyl acetate–methanol–acetic acid (5:4:1:1, v/v) as the solvent system. Five main GAs were successfully separated with purities over 98%. The structures of the separated GAs were determined based on standard samples coupled with Electrospray Ionization Mass Spectrometry (ESI-MS) results. This separation method of coupling PZRCCC with inner-recycling CCC is effective for the preparation of GAs from the sarcotesta of G. biloba and could be further applied to separate organic acids of low polarity in other natural products.

Three new terpenes, classified as one cembrane-type diterpenoid (rel)-(1S,5R,7E,11E)-1-isopropyl-8,12-dimethyl-4-methylenecyclotetradeca-7,11-diene-1,5-diol (1), one dinortirucallane-type triterpene 20,21-dinortirucalla-8,24-diene-3β-ol-7-one (2) and one ursane-type triterpene 21β-hydroxy-3-O-acetyl-11-keto-boswellic acid (3), respectively, along with four known triterpenes, were isolated from the gum resin of Boswellia carterii. Their structure elucidations were achieved by in-depth spectroscopic examination, mainly including experiments and analyses of multiple 1D- and 2D-NMR and HR-ESI-MS. The effects on nitric oxide (NO) production in lipopolysaccharide (LPS)-activated RAW264.7 cells of all the isolated compounds were evaluated in vitro. Compound 1, 4, 5 and 7 exhibited potent inhibitory effects on NO production with IC50 values of 1.32, 3.04, 1.42, and 3.25 μM.

Platycosides, the generally recognized main active constituents of Platycodi radix, have been studied extensively for their wide pharmacological activities. Herein, we have successfully developed an efficient method for the enrichment and comprehensive isolation of platycosides from Platycodi radix by MCI resin column chromatography (CC) and two different modes of high-speed counter-current chromatography (HSCCC). MCI resin CC was the preferable enrichment operation for platycosides from the 70%-ethanol extract of Platycodi radix and rendered target platycosides when eluted by 60% aqueous methanol solution. As for the separation, two different modes, including isocratic HSCCC and linear-gradient HSCCC, were applied together to separate the platycosides using a mixture of ethyl acetate, n-butanol and water coupled with evaporative light scattering detection, for the first time. Isocratic HSCCC was applied to separate crude platycosides from Platycodi radix using ethyl acetate–n-butanol–water (1 : 1 : 2, v/v), yielding seven pure platycosides (compounds 1–6, 8) and two fractions of enriched mixtures of compounds 7, 9, 10, and 11. Linear-gradient HSCCC was employed to rapidly separate compounds 7, 9, 10, and 11 by constantly changing the proportions of ethyl acetate and n-butanol in the ethyl acetate–n-butanol–water solvent system. Finally, platycoside E (1), deapio-platycodin D3 (2), platycodin D3 (3), deapio-platycodin D2 (4), platycodin D2 (5), platycodin D (6), polygalacin D2 (7), polygalacin D (8), and three tautomers, namely 2′′-O-acetylplatycodin D (9) and 3′′-O-acetylplatycodin D (9′), 2′′-O-acetylpolygalacin D2 (10) and 3′′-O-acetylpolygalacin D2 (10′), and 2′′-O-acetylpolygalacin D (11) and 3′′-O-acetylpolygalacin D (11′), were obtained from 300 mg of crude platycosides from Platycodi radix.

Eight new cembrane-type diterpenoids, boscartins AP-AW (1–8) were obtained from the gum resin of Boswellia carterii. Among which, six ones (2–7) were isomers, with one hydroxy group and two double bonds migrating along the carbocycle. The structures were elucidated by spectroscopic examination. All isolates were evaluated for anti-inflammatory activity and hepatoprotective activity by cell models of LPS-induced RAW 264.7 mouse peritoneal macrophages and APAP-induced HepG2 cells, respectively. As for anti-inflammatory activity assay, compound 1 exhibited potent activity against NO production (IC50 of 13.1 μM), with the other ones exhibiting weak anti-inflammatory activity (IC50 > 50 μM). As for hepatoprotective activity assay, compound 1 exhibited more significant activity (inhibition rate of 30.7%) than that of the positive control (bicyclol, inhibition rate of 27.2%), and compounds 4, and 6 showed nearly the same activities as the control (inhibition rates of 26.7% and 25.9%, respectively), with the other ones exhibiting weak hepatoprotective activity.

Seven new diterpenoids, classified as three cembrane-type diterpenoids boscartins I-K (1–3) and four prenylaromadendrane-type diterpenoids boscartols K-N (4–7), respectively, along with nine known diterpenoids, were isolated from the gum resin of Boswellia carterii. Their structure elucidations were achieved by spectroscopic examination. All isolates were evaluated for anti-inflammatory activity against nitric oxide (NO) production and antiproliferative activity against MCF-7 human breast cancer cell in vitro. 4 and 5 exhibited potent inhibitory effects on NO production (IC50 of 2.22 and 1.10 μM, respectively), with 11 showing moderate inhibition (IC50 of 8.63 μM), and 12 and 15 demonstrated moderate antiproliferative effects against MCF-7 cell (IC50 of 9.5, and 6.3 μM, respectively).

Two new alkaloid glycosides (1–2), two new amide alkaloids (3 and 6), and two new amine alkaloids (4 and 5), were isolated from Scindapsus officinalis (Roxb.) Schott., along with four known alkaloids (7–10). Structural elucidation of the isolated compounds was established by spectroscopic analysis, especially 2D NMR techniques and comparison with literatures. The absolute configurations of compounds 1 and 2 were determined by the electronic circular dichroism calculations. Compound 1 represent the first example of alkaloid glycoside found to possess an unprecedented 2,5-methanocyclopenta[b]azepine core. All isolates were evaluated for cytotoxic activity against MCF-7 human breast cancer cell and anti-inflammatory activity against nitric oxide (NO) production in vitro. Compounds 4, 6 and 8 demonstrated moderate cytotoxic effects against MCF-7 cell (IC50 of 11.6, 25.3, and 20.5 μM, respectively), and 1, 7 and 9 exhibited moderate inhibitory effects on NO production (IC50 of 19.8, 30.3, and 11.8 μM, respectively).

Eight new cembrane-type diterpenoids, boscartins AH-AK (1-8), along with two known ones (9-10), were isolated from the gum resin of

Herein, we provide an effective separation strategy based on liquid-liquid extraction and two different modes of high speed counter-current chromatography (HSCCC) for the rapid enrichment and separation of compounds from

One new triterpenoid saponin (1), as well as six known ones (2–7), were isolated from the ethanol extract of the thorns of Gleditsia sinensis. Their structures were elucidated by extensive spectroscopic analysis in conjunction with chemical evidence. Cytotoxic activity of compounds 1–6 was evaluated against human breast cancer MCF 7 cells in vitro by the MTT method. Our results revealed moderate activities for compounds 1–6 with IC50 values of 18.43, 30.47, 18.46, 10.02, 30.76, and 17.32 μM, respectively. Furthermore, compounds 1, 3, 4, and 6 induced apoptosis in MCF 7 cell, with 1 and 6 causing late apoptosis of MCF 7 cells, while 3 and 4 acting oppositely.

In this work, six coumarins, including two new ones, 8-(3-hydroxy-2,2-dimethylpropyl)-7-methoxy-2H-chromen-2-one (2) and 5-[(7′,8′-dihydroxy-3′,8′-dimethyl-2-nonadienyl)oxy] psoralen (4), as well a...

Pb

Piper longum L. (Piperaceae) is famous for flavoring food and treatment purposes. N-Alkylamides (NAAs) are the most common secondary metabolites found in Piper species with broad spectrum of biological properties. Because of the similar structures and lower polarities, it is difficult to separate NAAs by traditional chromatographic methods. Herein, an efficient off-line two-dimensional coupled with gradient high-speed counter-current chromatography (HSCCC) method is reported for preparative separation of N-alkylamides from P. longum. The HSCCC solvent system with n-hexane/ethyl acetate/methanol/water (5:4:5:4, v/v) was used for the first dimensional separation. Two pure compounds i.e. piperlonguminine (1) and piperine (2) were successfully separated, coupled with an enriched trace ingredient. Furthermore, the enriched ingredient was used for the second dimensional separation with a gradient HSCCC mode by adjustment of the mobile phase with more enhanced elution ability. Eight minor compounds were successfully separated including retrofractamide A (3), retrofractamide C (4), dehydropipernonaline (5), pipernonaline (6), piperundecalidine (7), guineesine (8), brachystamide B (9), and (2E,4E,12Z)-N-isobutyl-2,4,12- octadecatrienamide (10). The structures of the isolated pure compounds were characterized by ESI-MS, 1H, and 13C NMR spectral analysis.

In general, the simultaneous separation and isolation of compounds with a broad polarity range from natural products is a challenge by ordinary high-speed counter-current chromatography (HSCCC). Indeed, the complex solvent system screening methods limit the broader application of HSCCC. We describe herein a rapid and efficient linear gradient CCC (LGCCC) method that enables the separation of flavonoid glycosides with a broad range of KD values from custard apple leaves. Inner-recycling CCC (IRCCC) mode has been further applied for the separation of compounds with similar KD values. Similarly to binary gradient HPLC, the LGCCC mode is achieved by adjustment of the proportion between ethyl acetate (pump A) and n-butanol (pump B) in an ethyl acetate/n-butanol/water solvent system. Various separation factors have been investigated, including separation mode, rotation speed, flow rate, and sample loading. The IRCCC mode has been used for the secondary separation of two epimers with a simple ethyl acetate/water (1:1, v/v) solvent system. Finally, five main flavonoid glycosides have been successfully separated, namely quercetin-3-O-robinobioside (1, 4.8 mg) and rutin (2, 12.1 mg), quercetin-3-O-β-d-glucoside (3, 4.2 mg), kaempferol-3-O-robinobioside (4, 9.6 mg), and kaempferol-3-O-rutinoside (5, 24.6 mg). The purities of the separated flavonoid glycosides were over 98%, as determined by HPLC. Our study indicates that a suitable combination of LGCCC and IRCCC modes is an effective strategy for separating flavonoid glycosides from custard apple leaves. The mathematical expression of the LGCCC was deduced to illuminate the separation mechanism. It may also be applied to obtain component fractions for the further screening of active compounds from complex natural products.

One new monoterpene glycoside (1), one new phenyl glycoside (2), one new caffeoyl derivative (3), were isolated from Scindapsus officinalis (Roxb.) Schott., along with four known compounds (4&ndash, 7). Structures of the isolated compounds were elucidated by extensive analysis of spectroscopic data, especially 2D NMR data and comparison with literatures. All isolates were evaluated for anti-inflammatory activity against nitric oxide (NO) production in vitro. Compounds 3 and 7 exhibited moderate inhibitory effects on NO production with IC50 values of 12.2 &plusmn, 0.8 and 18.9 &plusmn, 0.3 &mu, M, respectively.

One new monoterpene glycoside (1), one new phenyl glycoside (2), one new caffeoyl derivative (3), were isolated from Scindapsus officinalis (Roxb.) Schott., along with four known compounds (4–7). Structures of the isolated compounds were elucidated by extensive analysis of spectroscopic data, especially 2D NMR data and comparison with literatures. All isolates were evaluated for anti-inflammatory activity against nitric oxide (NO) production in vitro. Compounds 3 and 7 exhibited moderate inhibitory effects on NO production with IC50 values of 12.2 ± 0.8 and 18.9 ± 0.3 μM, respectively.

One new triterpenoid saponin (

One new quinolinic scandine-type monoterpeniod alkaloid, 3-oxo-scandine (1), as well as seven known ones (2–8), was isolated from the roots of Melodinus henryi. Their structures were elucidated by extensive spectroscopic analysis. All of the compounds were prepared and evaluated for their anti-inflammatory activities by measuring the inhibitory activity of nitric oxide (NO) in vitro in RAW 264.7 mouse peritoneal macrophages. Compounds 6 and 7 showed significant activities with IC50 values of 8.54 and 5.19 μM, respectively.

Five new chromone glycosides, officinalisides A (1), B (2), C (3), D (4) and E (5) were isolated from Scindapsus officinalis (Roxb.) Schott., along with six known chromone derivatives, 7-O-α-l-rhamnosyl-nereugenin (6), undulatoside A (7), drynachromoside A (8), drynachromoside B (9), 5,7-dihydroxy-2-methyl chromone(10), 5,7-dihydroxy-2-hydroxymethyl chromone (11). Structural elucidation of the isolated compounds was established by spectroscopic analysis, especially 2D NMR techniques and comparison with literatures. The isolates were evaluated for anti-inflammatory activities in a LPS-stimulated RAW 264.7 model using inhibition of nitric oxide (NO) production as an indicator. Compounds 2, 4 and 10 demonstrated potential anti-inflammatory activity with IC50 values of 16.1, 19.1, and 13.4μM, respectively, compared to the positive control dexamethasone.

Five terpenoids, including two new ones, 3,7-dioxo-tirucalla-8,24-dien-21-oic acid (2) and 3α-acetoxyl-7-oxo-tirucalla-8,24-dien-21-oic acid (3), and three known ones, boscartol A (1), 11-keto-β-boswellic acid (4), and acetyl-11-keto-boswellic acid (5), have been extracted by the ultrapressure extraction and purified by pH-zone-refining countercurrent chromatography and high-speed countercurrent chromatography from olibanum. For ultrapressure extraction, the optimal condition including 200 MPa of extraction pressure, ethyl acetate of extraction solvent, 1:20 (g/mL) of solid/liquid ratio, and 2 min of extraction time were obtained. For the separation, from 1.5 g of the terpenoid extract, 220.1 mg of 4, 255.5 mg of 5, and 212.3 mg of the mixture of 1, 2, and 3 were obtained by pH-zone-refining countercurrent chromatography under the solvent system of chloroform/ethyl acetate/methanol/water (3:1:3:2, v/v/v/v) with aqueous ammonia and trifluoroacetic acid as retention and eluter agents. The enriched mixture (210 mg) was further separated by conventional high-speed countercurrent chromatography with petroleum ether/ethyl acetate/methanol/water (1:0.8:1.1:0.6, v/v/v/v), yielding 30.1 mg of 1, 35.5 mg of 2, 12.3 mg of 3. The structures of these five terpenoids were elucidated by extensive spectroscopic methods.

The aim of this paper was to seek an efficient method to preparative separation of alkaloid compounds from Aconitum coreanum (Guanbaifu), a well-known traditional Chinese medicinal plant for heart disease. Seven alkaloid compounds were successfully purified by pH-zone-refining counter-current chromatography with two-phase solvent system of petroleum ether-ethyl acetate-methanol-water (5:5:1:9, v/v/v/v), 10 mM triethylamine in upper phase and 10 mM hydrochloric acid in lower phase. From 3.5 g of crude extract, 356 mg of Guanfu base I, 578 mg of Guanfu base A, 74 mg of atisine, 94 mg of Guanfu base F, 423 mg of Guanfu base G, 67 mg of Guanfu base R and 154 mg of Guanfu base P were obtained with the purity of 96.40%, 97.2%, 97.5%, 98.1%, 98.9%, 98.3% and 98.4%. Their chemical structures were identified by TOF-MS and 1H-NMR. This study indicated that pH-zone-refining counter-current chromatography was an efficient method for separating the kind of alkaloids with low absorbance values.

Five new caffeoyl cyclobutantetraol esters ( 1 – 5 ) and one hydroxycinnamoyl cyclobutantetraol ester ( 6 ), were isolated from Scindapsus officinalis (Roxb.) Schott, which were the first reported phenolic metabolites incorporating a cyclobutantetraol in nature. Structures of the isolated compounds, including absolute configurations, were elucidated by spectroscopic analysis, especially 2D NMR techniques and exciton chirality CD (ECCD) method. All isolates were evaluated for cytotoxic activity toward MCF-7 human breast cancer cell, anti-inflammatory activity against nitric oxide (NO) production, and their antioxidative activity in the 1,1-diphenyl-2-picrylhydrazyl assay in vitro . Compound 1 showed strong antioxidative activity with IC 50 value of 59.2 μM, and compounds 1 – 6 exhibited weak inhibitory effects on NO production, while hardly showing any cytotoxic effects against MCF-7 cell.

One new flavanocoumarin (1), as well as six known flavonoids (2–7), was isolated from the ethyl acetate extract of the thorns of Gleditsia sinensis. The structures of these compounds were elucidated by extensive spectroscopic measurements and comparison with data reported in literatures. Cytotoxic activities of compounds 1–6 were evaluated against human liver cancer SK-hep-1 cells in vitro by the MTT method, with compound 1 displaying moderate activity (IC50 of 62.53 μM). Furthermore, compound 1 could increase the number of apoptosis cells in a concentration-dependent manner.