Chaetomadrasins A and B, Two New Cytotoxic Cytochalasans from Desert Soil-Derived Fungus Chaetomium madrasense 375.

Two new cytochalasans, Chaetomadrasins A (1) and B (2), along with six known analogues (3-8), were isolated from the solid-state fermented culture of desert soil-derived Chaetomium madrasense 375. Their structures were clarified by comprehensive spectroscopic analyses, and the absolute configurations of Compounds 1 and 2 were confirmed by electronic circular dichroism (ECD) and calculated ECD. For the first time, Chaetomadrasins A (1), which belongs to the chaetoglobosin family, is characterized by the presence of all oxygen atoms in the form of Carbonyl. Chaetomadrasin B (2) represents the first example of chaetoglobosin type cytochalasan characterized by a hydroxy unit and carbonyl group fused to the indole ring. Compounds 1 and 2 displayed moderate cytotoxicity against HepG2 human hepatocellular carcinoma cells.

Chemical constituents and coagulation activity of Agastache rugosa.

BACKGROUND: In the Chinese traditional medicine, plant of Agastache rugosa (Fisch. & C.A. Mey.) Kuntze (A. rugosa) has been used to treat nausea, vomiting and dispel damp. However, currently, few reports about the chemical constituents, especially the non-volatile components of A. rugosa are available. METHODS: Through separation with various column chromatographies to elucidate the chemical constituents of A. rugosa, the biological activities of the major constituents were investigated. The extracts and main constituents of A. rugosa were evaluated for their anticoagulant effects by assaying the activated partial thromboplastin time (APTT), prothrombin time (PT), thrombin time (TT) and fibrinogen (FIB) in vitro. RESULTS: Seven known compounds (namely compounds 1-7) were isolated from the aerial parts of A. rugosa. They were identified as methyl hexadecanoate (1), ß-sitosterol (2), acacetin (3), ursolic acid (4), apigenin (5), protocatechuic acid (6) and tilianin (7), respectively. Compounds 1 and 6 were isolated from the genus Agastache for the first time, and compound 4 was obtained from the plants for the first time. The results showed that the extract of A. rugosa had a significant procoagulant activity by shortening the time of PT (P < 0.001) and increasing FIB content (P < 0.001), as compared with Vitamin K1. While its major constituents acacetin and tilianin exhibited significant anticoagulant activities by prolonging the times of PT, APTT, TT and reducing FIB content (P < 0.001), as compared with blank control group. CONCLUSIONS: The total extract of A. rugosa possessed significant procoagulant activity, while its main components, acacetin and tilianin possessed significant anticoagulant activities. Further investigation should be pursued to find out the bioactivity components responsible for the procoagulant action of the plant.

Effects of Flavonoids in Lysimachia clethroides Duby on the Activities of Cytochrome P450 CYP2E1 and CYP3A4 in Rat Liver Microsomes.

Incubation systems were established to investigate the effects of quercetin, kaempferol, isoquercitrin and astragalin in Lysimachia clethroides Duby on the activities of CYP2E1 and CYP3A4 in rat liver microsomes in vitro. Probe substrates of 4-nitrophenol and testosterone as well as flavonoids at different concentrations were added to the incubation systems. After incubation, a validated high performance liquid chromatography (HPLC) method was applied to separate and determine the relevant metabolites. The results suggested that kaempferol exhibited a weak inhibition of CYP2E1 activity with an IC50 of 60.26 ± 2.54 µM, while quercetin and kaempferol caused a moderate inhibition of CYP3A4 activity with IC50 values of 18.77 ± 1.69 µM and 32.65 ± 1.32 µM, respectively. Isoquercitrin and astragalin had no effects on the activities of either CYP2E1 or CYP3A4. It could be speculated from these results that the inhibitory effects of quercetin and kaempferol on the activities of CYP2E1 and CYP3A4 could be the mechanisms underlying the hepatoprotective effects of L. clethroides.

[Simultaneous determination of quercitrin, phloridzin and 3-hydroxyl phloridzin in leaves of Malus halliana by ultrasound-assisted ionic liquid-reversed phase liquid chromatography].

To establish a method for the simultaneous determination of phloridzin, 3-hydroxy phloridzin and quercitrin in leaves of Malus halliana by ultrasonic-assisted ionic liquid coupled with RP-HPLC. An Agilent TC-C18 (4.6 mm×250 mm, 5 µm) column was used, with the mobile phase of acetonitrile and 1% phosphoric acid-water (20∶80) by gradient elution at the detection wavelength of 270 nm. The flow rate was 0.8 mL•min⁻¹, and chromatographic column temperature was controlled at the room temperature. Under the optimized conditions, the linear ranges for phloridzin, 3-hydroxy phloridzin and quercitrin were 0.9-112.5 µg (r = 0.999 6), 0.093 2-11.65 µg (r = 0.999 1) and 0.097 2-12.15 µg (r = 0.999 8), respectively. The average recoveries of the three constituents were 99.35%, 98.80% and 98.19%, respectively. The method was environmental friendly, rapid, accurate and highly reproducible, and so suitable for the quantitative analysis of phloridzin, 3-hydroxy phloridzin and quercitrin in leaves of M. halliana.

[Effect of heating treatment on stability of two coumarins in Angelica dahurica and activity of tyrosinase].

To study the heating treatment of Angelica dahurica under different temperature and time conditions on the stability of coumarins and tyrosinase activity. HPLC method was used to determine the contents of imperatorin and isoimperatorin, and tyrosinase activity was assayed by measuring the oxidation rate of L-DOPA in vitro. After heated, the contents of imperatorin increased. Expect for being heated at 90 ℃ for 2 h, the content of isoimperatorin was higher than crude one. Before and after being heated, A. dahurica showed an activating effect on tyrosinase. In the same temperature and time conditions, the activation rate increased with the rise of concentration of tyrosinase extracts. Heating process for A. dahurica could change the contents of imperatorin and isoimperatorin, mainly increasing their concentrations.

[Spectrum-effect relationship in antioxidant activity of Ligustri Lucidi Fructus based on DPPH, ABTS and FRAP assays].

Characteristic chromatogram of Ligustri Lucidi Fructus which were processed by heat treatment with different temperatures and times was developed by HPLC. DPPH, ABTS and FRAP assays were performed to determine the antioxidant activity. The spectrum-effect correlation was studied using Partial Least Squares(PLS)to explore the active ingredients of Ligustri Lucidi Fructus by investigating the relationship between HPLC spectrum and antioxidant activity. S1, S2, S15, S24, S27, S29, S32, S33 and S35 were characteristic compounds in 35 matching characteristic chromatograms which were positive relationship with scavenging DPPH free radical activity. S1, S2, S5, S8, S16, S27 and S33 were significantly positively related to scavenge ABTS free radical activity. S12, S20, S22, S28, S30, S31, S32 and S34 were significantly positively related to restore Fe³âº activity. Among the chromatographic peaks, S1, S2, S27 and S33were positively related to scavenge DPPH free radical and ABTS free radical activity, and S32 was positively related to scavenge DPPH free radical and restore Fe³âº activity. S3, S19, S21, S22, S23, S33 and S34 were determined as salidroside, luteolin-7-O-glucoside, specnuezhenide, oleuropein, ligustroflavone, luteolin andapigenin, respectively. The results showed that although specnuezhenide and salidroside were stipulated index compounds to evaluate the quality of Ligustri Lucidi Fructus, the Ligustri Lucidi Fructus pharmcodynamic effect did not depend on the contents of those index components. The quality of traditional Chinese medicines(TCMs)should be determined by the compound groups associated with pharmcodynamic effect.

[Research progress on chemical compounds and pharmacological effects of Caesalpinia].

Consult literature, the chemical composition of the type of system Caesalpinia plants were summarized and discussed in detail its pharmacological effects. The genus contains major chemical components of high isoflavones, chalcones and diterpenoids, pharmacological effects inhibit melanin production, anti-inflammatory, antioxidant, antibacterial, immune regulation, and further research in this genus offer reference.

Simultaneous determination of alizarin and rubimaillin in Rubia cordifolia by ultrasound-assisted ionic liquid-reversed phase liquid chromatography.

Four kinds of ionic liquids were adopted to analyze the content of rubimaillin and alizarin in Rubia cordifolia roots with ultrasonic-assisted extraction coupled with HPLC. The chromatographic column, Purospher star RP-C18 (4.6 mm x 250 mm, 5 microm), was used. Methanol and 0.4% acetic acid-water as mobile phase with flow rate at 0.85 mL min(-1), gradient elution, detection wavelength at 250 nm, chromatographic column temperature was controlled at room temperature. The result showed that rubimaillin and alizarin had the highest extraction yield when the [ HMIM] PF6methanol solution concentration of 0.6 mol x L(-1) as extraction solvent and the conditions were solid-liquid ratio of 1:80 (g x mL(-1)). Under the optimal extraction conditions, the content of alizarin from 0.01 to 0.04 microg showed a good linearity (r = 0.9999), the average recovery was 97.12%, the content of rubimaillin from 0.41 to 1.35 microg showed a good linearity (r = 0.9999), the average recovery was 98.10%. This experiment adopted environmentally friendly reagent as extraction solvent, the extraction efficiency was improved, and the environmental pollution caused by organic solvent was avoided, the harm of human body aslo was reduced. This method was simple and reliable, its repeatability was also very good, which had an important significance in the study of traditional Chinese medicine active ingredient extraction methods.

[Advance on chemical compounds of Ainsliaea genus].

Plants in Ainsliaea genus, belongs to Compositae family, are traditional Chinese medicine and widely used in folk. These plants contain various types of chemical components, and main components are sesquiterpene lactone and its glycosides. In addition, there are triterpenoids, flavonoids, steroids, phenolic acid, long chain fatty acid and volatile oils. Recently, much attention has been payed to varlous research of A. fragrans. This paper reviewed and summarized the chemical components to provide the theoretical basis for the use of Ainsliaea.

[Analysis of four flavonoids in Lysimachia clethroides using ionic liquid-assisted extraction].

In order to established a method for simultaneous determination of isoquercitrin, astragaline, quercetin and kaempferol in Lysimachia clethroides, the ionic liquid 1-hexyl-3-methylimidazolium hexafluorophosphate ([HMIM]PF6) methanol was used as the ultrasound-assisted extraction solvent combing with RP-HPLC. A Purospher star RP-C1 column was used with the mobile phase of aceto- nitrile, methanol and 0. 4% phosphate acid by gradient elution at the detection wavelength of 360 nm. The flow rate was 0.7 mL x min(-1), and the column temperature was the room temperature. Under the optimized conditions, the linear ranges were 2.54 x 10(-2)-2. 54, 2.50 x 10(-2)- 2.50, 1.54 x 10(-3)-0.154, 1.49 x 10(-3)-0.149 microg for isoquercitrin, astragaline, quercetin and kaempferol, respectively. The average recoveries of the four constituents were 101.1%, 98.90%, 101.0%, 101.6%, respectively. The method was green, simple, rapid and accurate, and provided a valid method for analysis of isoquercitrin, astragaline, quercetin and kaempferol in L. clethroides.

[Determination of oleanic acid and paeoniflorin in Paeonia lactiflora by ultrasound-assisted ionic liquid-reversed phase liquid chromatography].

Four kinds of ionic liquids [BMIM] Br, [BMIM] BF4, [BMIM] PF6, [HMIM] PF6 were used to analyze the content of oleanic acid and paeoniflorin in Paeonia lactiflora with ultrasonic-assisted extraction coupled with HPLC. The chromatographic column, Purospher star RP-C18 (4.6 mm x 250 mm, 5 µm), was used. Acetonitrile and water (90:10) as mobile phase was used to determine the content of oleanic acid with a gradient elution and flow rate at 1.00 mL · min(-1), detection wavelength at 210 nm, chromatographic column temperature at room temperature. Paeoniflorin content was determined using acetonitrile and water (18:82) as mobile phase with a gradient elution and flow rate at 1.00 mL · min(-1), detection wavelength at 250 nm, the chromatographic column temperature at room temperature. The result show that oleanic acid has the highest extraction yield when the conditions are solid-liquid ratio of 1:80 (g · mL(-1)), and the [BMIM] Br methanol solution concentration of 0.6 mol · L(-1). Under the optimal extraction conditions, the content of oleanic acid from 0.24 to 3.76 µg showed a good linearity (r = 0.9999), the average recovery was 97.20%. Paeoniflorin has the highest extraction yield when the conditions are solid-liquid ratio of 1:130 (g · mL(-1)), and the [C4 MIM] PF6 methanol solution concentration of 0.6 mol · L(-1). Under the optimal extraction conditions, paeoniflorin content from 0.42 to 4.20 µg showed a good lin- earity (r = 1.000), the average recovery was 98.84%. This method is simple and reliable, its repeatability is also very good. It has important significance in the study P. lactiflora of ionic liquid microextraction.

[Advances of chemical constituents and pharmacological activities of Myristica genus].

The genus Myristica (Myristicaceae) consists of 120 species, which were distributed in South Asia, from west Polynesia, Oceania, eastern India to the Philippines. Phytochemical studies showed that 164 compounds including a majority of lignans, along with phenglpropanoids, flavonoids and phenolics, have been isolated from this genus, which exhibited anti-microbial, anti-inflammatory, anticancer, hyperglycemic and hepatic protective activities. This article summarizes research progress of the chemical compositions and their pharmacological activities from this genus, which could provide reference for the in-depth development and utilization of the Myristica plants.

Effects of undescribed iridoids in Patrinia punctiflora on insulin resistance in HepG2 cells.

Patrinia punctiflora is a medical and edible Chinese herb with high nutritional and medicinal value. The continuing study of its chemical constituents led to the isolation of six iridoids, which were previously unreported compounds, patriscabioins PU (1-6). Their structures were characterized and confirmed with NMR (1D & 2D), HRMS, IR and UV. Among them, compound 5 was screened to evaluate its insulin resistance activity on an IR-HepG-2 cell model. Compound 5 had no cytotoxicity compared with the control group and could promote glucose uptake in IR-HepG-2 cells. Through further mechanism studies, the undescribed compound 5 could increase the expression levels of PI-3 K, p-AKT, GLUT4 and p-GSK3ß proteins. Moreover, the expression of PEPCK and G6Pase proteins, which are key gluconeogenic enzymes, was also inhibited. Thus, compound 5 promotes the transfer of GLUT4 to the plasma membrane by activating the PI-3 K/AKT signaling pathway, at the same time, promotes glycogen synthesis and inhibits the onset of gluconeogenesis, which in turn ameliorates insulin resistance.

[Advance in studies on pharmacological activities of chelerythrine].

Chelerythrine is a kind of benzo[c] phenanthridine alkaloids, with such pharmacological activities as antitumor, antibiosis and anti-inflammation, which is widely found in plant of Fumariaceae, Papaveraceae, Ranunculaceae and Rutaceae families. This article summarizes the advances in domestic and foreign studies on pharmacological effect of chelerythrine in the recent decade, in the expectation of providing scientific basis for the in-depth studies, development and utilization of chelerythrine.

[Chemical constituents from Lysimachia circaeoides].

OBJECTIVE: To study the chemical constituents from Lysimachia circaeoides. METHODS: The column chromatographic techniques were applied to isolate the constituents. EI-MS and NMR were used to identify the structures. RESULTS: Eight compounds were isolated and identified from the extract of L. circaeoides and their structures were elucidated as kaempferol (1), beta-daucosterol (2), beta-sitosterol (3), quercetin (4), luteolin (5), quercetin-3-O-beta-D-galactoside (6), kaempferol-3-O-beta-D-glucoside (7) and rutin (8). CONCLUSION: Compounds 1 - 8 are isolated from this plant for the first time.

[Chemical constituents of Lysimachia paridiformis].

OBJECTIVE: To study the chemical constituents from Lysimachia paridiformis. METHODS: The column chromatographic techniques were applied to isolate the chemical constituents of Lysimachia paridiformis. EI-MS and NMR were used to identify the structures. RESULTS: Seven compounds were isolated and identified from the extract of L. paridiformis, and their structures were elucidated as stigmasterol (1), oleanolic aicd (2), beta-amyrin (3), quercetin (4), luteolin (5), quercetin-3-O-beta-D-galactoside (6) and beta-daucosterol (7). CONCLUSION: Compound 1 -7 are isolated from this plant for the first time.

[Chemical constituents from Psoralea corylifolia and their antioxidant alpha-glucosidase inhibitory and antimicrobial activities].

Twelve compounds were isolated from Psoralea corylifolia and their structures were identified as isopsoralen (1), psoralen (2), 8-methoxypsoralen (3), psoralidin (4), corylin (5), bavachin (6), daidzein (7), corylifolinin (8), bavachinin (9), neobavaisoflavone (10), daidzin (11) and astragalin (12). The results showed that psoralidin had the activity of scavenging DPPH free radicals activity (IC50 43.85 mg x L(-1)). Psoralidin (IC50 1.32 mg x L(-1))c, oryfolin (IC50 4.97 mg x L(-1)), daidzin (IC50 10.47 mg x S(-1)), daidzein (IC50 34.22 mg) x L(-1)) and astragalin (IC50 31.27 mg x L(-1)) had the activity of scavenging ABTS free radical. Psoralidin (IC50 40.74 mg x L(-1)), coryfolin (IC50 45.73 mg x L(-1)) and daidzein (IC50 49.44 mg x L(-1)) had alpha-glucosidase inhibitory activity. Corylifolinin and neobavaisoflavone had significantly effect of inhibiting SA, MRSA and ESBLs-SA (MIC 0. 781 3, 1.562, 5, 0.781 25 microg x disc(-1) and 6.25, 6.25, 6.25 microg x disc(-1).

[Advances in studies on chemical constituents and biological activities of Desmodium species].

The chemical constituents isolated from Desmodium species (Leguminosae) included terpenoids, flavonoids, steroids, alkaloids compounds. Modem pharmacological studies have showed that the Desmodium species have antioxidant, antibacterial, anti-inflammatory, hepatoprotective, diuretic, antipyretic, analgesic and choleretic activity. This article mainly has reviewed the research advances of chemical constituents and biological activities of Desmodium species since 2003.

[Alpha-glucosidase inhibitory activity of Aeschynanthus maculatus].

OBJECTIVE: To study the inhibitory activity of Aeschynanthus maculatus on alpha-glucosidase. METHOD: The inhibilitory model of in vitro alpha-glucosidase was established. Active extracts of A. maculatus were isolated and identified bymultiple chromatographic methods, and their molecular structures were identifiied by spectral techniques. RESULT: Seven coumpounts were isolated from A. maculatus and isolated as lupeol(1), stigmasterol(2), ursolic acid(3), stigmast-5,22(E)-diene-3beta-ol(4), beta-daucosterol(5), 3-hydroxy-12-taraxasten-28-oic-acid(6) and oleanic acid(7). Compounds 1 (IC50 25.41 mg x L(-1)),3(IC0 4.42 mg L(-1)),4(IC50 11.50 mg x L(-1)),6(IC50 14.17 mg x L(-1)) and 7(IC50 2.88 mg x L(-1)) had higher inhibitory activities than that of acarbose (IC50 1103.01 mg x L(-1)) as the positive control drug. CONCLUSION: Compound 1-7 were isolated from this plant for the first time. Compound 6 was isolated from Gesneriaceae family for the first time. Compound 7 was isolated from Aeschynanthus genus for the first time.

[Determination of effective time of Schizonepeta tenuifalia pieces by classical constant temperature acceleration experiment].

OBJECTIVE: To study the validity of Schizonepeta tenuifalia pieces. METHOD: The change principle for the contents of essential oil and pulegone was determined by the way of classical constant temperature acceleration experiment, and the reacting speed at 20 degrees C was calculated according to Arrhenius index law and effective time was calculated. RESULT: In classical constant temperature experiment, the content change of essential oil with the regular pattern of one level. The effective time of S. tenuifalia pieces stored in 20 degrees C was 2.08 years and the constant of speed is 8.453 4 x 10(-6) carried out by essentialoil, 190 days with the constant of speed is 3.39 x 10(-5) carried out by pulegone. CONCLUSION: The effective time of S. tenuifalia pieces was about 2 years carried out by essential oil and 190 days carried out by pulegone by the way of classical constant temperature experiment.