A new phenylpropanoic acid congener from Zanthoxylum nitidum.

One new phenylpropanoic acid congener, 2R-(5'-methoxy) pandanusphenol B (1), along with 26 known isolates, were isolated from Zanthoxylum nitidum. Their structures were elucidated by comprehensive spectroscopic data and circular dichroism analyses. All compounds, except 4, 7-10, 15, 17, 19 and 25, were reported from Z. nitidum for the first time. Among them, 16 compounds (1-3, 5-6, 12-14, 16, 20-24 and 26-27) were discovered from genus Zanthoxylum for the first time, while 15 compounds (1-3, 5-6, 12-14, 20-24 and 26-27) were isolated from the Rutaceae family for the first time. All isolates were evaluated for their cytotoxicity against five human cancer cell lines and the results showed that compound 27 exhibited significant cytotoxicity toward HepG2 and T24, with IC50 values of 2.49 and 7.0 µM, respectively.

Corydalis saxicola Bunting: A Review of Its Traditional Uses, Phytochemistry, Pharmacology, and Clinical Applications.

Corydalis saxicola Bunting (CSB), whose common name in Chinese is Yanhuanglian, is a herb in the family Papaveraceae. When applied in traditional Chinese medicine, it is used to treat various diseases including hepatitis, abdominal pain, and bleeding haemorrhoids. In addition, Corydalis saxicola Bunting injection (CSBI) is widely used against acute and chronic hepatitis. This review aims to provide up-to-date information on the botanical distribution, description, traditional uses, phytochemistry, pharmacology, and clinical applications of CSB. A comprehensive review was implemented on studies about CSB from several scientific databases, such as SciFinder, Elsevier, Springer, ACS Publications, Baidu Scholar, CNKI, and Wanfang Data. Phytochemical studies showed that 81 chemical constituents have been isolated and identified from CSB, most of which are alkaloids. This situation indicates that these alkaloids would be the main bioactive substances and that they have antitumour, liver protective, antiviral, and antibacterial pharmacological activities. CSBI can not only treat hepatitis and liver cancer but can also be used in combination with other drugs. However, the relationships between the traditional uses and modern pharmacological actions, the action mechanisms, quality standards, and the material basis need to be implemented in the future. Moreover, the pharmacokinetics of CSBI in vivo and the toxicology should be further investigated.

New alkaloids and their in vitro antitumor activity of Corydalis balansae.

The chemical investigation on Corydalis balansae resulted in the isolation of three previous undescribed compounds (1, 10, and 11) and 17 known compounds. Compound 1 and 2 were obtained as two lignanamide dimers, and compound 11 had a spiro [benzofuranone-benzazepine] skeleton, which was found in Corydalis for the first time. The structures of new compound were determined by the detailed analysis of 1D/2D NMR, UV, and IR data. Absolute configurations of compounds 10 and 11 were defined by their crystal X-ray diffraction data and calculations of electronic circular dichroism (ECD). The CCK-8 method was used to assay the inhibition effect of all the compounds on the growth of Hela, MGC-803, A549, and HepG2 cancer cells. Compound 2, 13, and 14 showed moderate inhibitory activity against the tested cell lines. Compound 2 exhibited potential antitumor activity against MGC-803 cells with an IC50 value of 20.8 µM, while the positive control etoposide was 17.3 µM. Furthermore, results from the cellular-mechanism investigation indicated that compound 2 could induce S-phase cell-cycle arrest and MGC-803 cells apoptosis, which was triggered by the up-regulation of PARP1, caspase-3 and -9, Bax, and down-regulation of Bcl-2. The 2-induced strong apoptosis indicated that compound 2 had good potential as an antitumor lead compound.

Radical cyclizations of enynes/dienes with alcohols in water using a green oxidant.

A simple, eco-friendly, and efficient methodology for performing radical cyclizations of enynes/dienes with alcohols in water has been established. This methodology showed ease of scale up, and it was designed to use mild reaction conditions and no catalyst. It was also designed to employ K2S2O8 as a green oxidant and water as the solvent, conditions making this process clean and easy to operate, hence achieving the criteria of green chemistry.

Ce(OTf)3-Catalyzed Multicomponent Reaction of Alkynyl Carboxylic Acids, tert-Butyl Isocyanide, and Azides for the Assembly of Triazole-Oxazole Derivatives.

Cerium(III) triflate-catalyzed multicomponent reactions between alkynyl carboxylic acids, tert-butyl isocyanide, and organic azides have been developed. In the presence of Ce(OTf)3 (10 mol %), the cascade reaction of one molecule of alkynyl carboxylic acid with three molecules of tert-butyl isocyanides proceeds chemoselectively and regioselectively via a triple and ordered isocyanide insertion process at room temperature, and then the cesium-catalyzed [3 + 2] cycloaddtion reaction between the resulted alkynyl oxazole and organic azides was further initiated by the temperature elevation (100 °C), thereby leading to multisubstituted triazole-oxazole derivatives in practical, time-saving, one-pot operations. Furthermore, some of the synthesized target compounds showed potential anticancer activities against MGC803 (human gastric cancer cell) with IC50 values below 20 µmol L-1.

Synthesis and discovery of asiatic acid based 1,2,3-triazole derivatives as antitumor agents blocking NF-κB activation and cell migration.

A series of asiatic acid (AA) based 1,2,3-triazole derivatives were designed, synthesized and subjected to a cell-based NF-κB inhibition screening assay. Among the tested compounds, compound 6k displayed impressive NF-κB inhibitory activity with an IC50 value in the low micromolar range. A molecular docking study was performed to reveal key interactions between 6k and NF-κB in which the 1,2,3-triazole moiety and the hydroxyl groups of the AA skeleton were important for improving the inhibitory activity. Subsequently, surface plasmon resonance analysis validated the high affinity between compound 6k and NF-κB protein with an equilibrium dissociation constant (KD) value of 0.36 µM. Further studies showed that compound 6k observably inhibited the NF-κB DNA binding, nuclear translocation and IκBα phosphorylation. Moreover, in vitro antitumor activity screening showed that compound 6k (IC50 = 2.67 ± 0.06 µM) exhibited the best anticancer activity against A549 cells, at least partly, by inhibition of the activity of NF-κB. Additionally, the treatment of A549 cells with compound 6k resulted in apoptosis induction potency and in vitro cell migration inhibition. Thus, we conclude that AA based 1,2,3-triazole derivatives may be potential NF-κB inhibitors with the ability to induce apoptosis and suppress cell migration.

Design, synthesis and pharmacological evaluation of novel 2-chloro-3-(1H-benzo[d]imidazol-2-yl)quinoline derivatives as antitumor agents: in vitro and in vivo antitumor activity, cell cycle arrest and apoptotic response.

A series of novel 2-chloro-3-(1H-benzo[d]imidazol-2-yl)quinoline derivatives (3a1-3d6) were designed and synthesized as antitumor agents. In vitro antitumor assay results showed that some compounds exhibited moderate to high inhibitory activities against HepG2, SK-OV-3, NCI-H460 and BEL-7404 tumor cell lines, and most compounds exhibited much lower cytotoxicities against HL-7702 normal cell line compared to 5-FU and cisplatin. In vivo antitumor assay results showed that the representative compound 3a1 exhibited effective inhibition on tumor growth in the HepG2 xenograft mouse model. Mechanistic studies suggested that 3a1 may exert antitumor activity by the up-regulation of Bax, intracellular Ca2+ release, ROS generation, p21, p27 and p53, downregulation of Bcl-2, activation of caspase-9 and caspase-3 and subsequent cleavage of PARP, and inhibition of CDK activity.

Design, synthesis and pharmacological evaluation of new 2-oxo-quinoline derivatives containing α-aminophosphonates as potential antitumor agents.

A series of novel 2-oxo-quinoline derivatives containing α-aminophosphonates were designed and synthesized as antitumor agents. MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay results demonstrated that some compounds exhibited moderate to high inhibitory activity against HepG2, SK-OV-3 and NCI-H460 tumor cell lines, and most compounds showed much lower cytotoxicity against HL-7702 normal cells than 5-FU and cisplatin. The action mechanism of representative compound 5b was investigated by fluorescence staining assay, flow cytometric analysis and western blot (WB) assay, which indicated that this compound induced apoptosis and G2/M phase arrest accompanied by an increase in the production of intracellular Ca2+ and reactive oxygen species (ROS) and affecting associated enzymes and genes.

One-Pot Three-Component Synthesis of Novel Diethyl((2-oxo-1,2-dihydroquinolin-3-yl)(arylamino)methyl)phosphonate as Potential Anticancer Agents.

With the aim of discovering new anticancer agents, we have designed and synthesized novel α-aminophosphonate derivatives containing a 2-oxoquinoline structure using a convenient one-pot three-component method. The newly synthesized compounds were evaluated for antitumor activities against the A549 (human lung adenocarcinoma cell), HeLa (human cervical carcinoma cell), MCF-7 (human breast cancer cell), and U2OS (human osteosarcoma cell) cancer cell lines in vitro, employing a standard 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2-H-tetrazolium bromide (MTT) assay. The results of pharmacological screening indicated that many compounds exhibited moderate to high levels of antitumor activities against the tested cancer cell lines and that most compounds showed more potent inhibitory activities comparable to 5-fluorouracil (5-FU) which was used as a positive control. The mechanism of representative compound 4u (diethyl((2-oxo-1,2-dihydroquinolin-3-yl)(phenyl-amino)methyl)phosphonate) indicated that the compound mainly arrested HeLa cells in S and G2 stages and was accompanied by apoptosis in HeLa cells. This action was confirmed by acridine orange/ethidium bromide staining, Hoechst 33342 staining, and flow cytometry.

Antioxidant and antiglycation properties of different solvent extracts from Chinese olive (Canarium album L.) fruit

OBJECTIVE@#To evaluate the antioxidant activity, antiglycation property, and bioactive components content of different solvent extracts from Chinese olive (Canarium album L.) fruit.@*METHODS@#The dry powder of Chinese olive fruit was extracted with different solvents, i.e., water, water/ethanol (1/1, v/v), ethanol, methanol, acetone and ethyl acetate. The total phenolic, total flavonoids and total triterpenoids contents of various extracts were determined by spectrophotometric methods. Phenolic compounds were identified by high performance liquid chromatography. The assayed antioxidant activity was determined in vitro models such as antioxidant capacity by radical scavenging activity using 2,2'-Azino-bis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS), 1,1-diphenyl-2-picryl- hydrazyl (DPPH) and nitrite oxide methods, chelating activity on metal ions, lipid and protein peroxidation methods. In vitro glucose-bovine serum albumin assay was used to evaluate the antiglycation of various extracts.@*RESULTS@#The water/ethanol extracts of Chinese olive fruit exerted significant scavenging effects on free radicals and strong inhibitory effects on advanced glycation end products formation. The Chinese olive fruit extracts were rich in phenolic compounds and triterpenoids. Gallic acid, ferulic acid and rutin were identified from the water/ethanol extracts. Correlation analysis indicated that there was a linear relationship between the antioxidant potency, free radical scavenging ability and phenolic compounds content of the Chinese olive fruit extracts.@*CONCLUSIONS@#Chinese olive fruit could be a natural candidate for studies of dietary complement to diabetes treatment since it combines antioxidant and antiglycation activities.

Antioxidant and antiglycation properties of different solvent extracts from Chinese olive (Canarium album L.) fruit

Objective: To evaluate the antioxidant activity, antiglycation property, and bioactive components content of different solvent extracts from Chinese olive (Canarium album L.) fruit. Methods: The dry powder of Chinese olive fruit was extracted with different solvents, i.e., water, water/ethanol (1/1, v/v), ethanol, methanol, acetone and ethyl acetate. The total phenolic, total flavonoids and total triterpenoids contents of various extracts were determined by spectrophotometric methods. Phenolic compounds were identified by high performance liquid chromatography. The assayed antioxidant activity was determined in vitro models such as antioxidant capacity by radical scavenging activity using 2,2'-Azino-bis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS), 1,1-diphenyl-2-picryl- hydrazyl (DPPH) and nitrite oxide methods, chelating activity on metal ions, lipid and protein peroxidation methods. In vitro glucose-bovine serum albumin assay was used to evaluate the antiglycation of various extracts. Results: The water/ethanol extracts of Chinese olive fruit exerted significant scavenging effects on free radicals and strong inhibitory effects on advanced glycation end products formation. The Chinese olive fruit extracts were rich in phenolic compounds and triterpenoids. Gallic acid, ferulic acid and rutin were identified from the water/ethanol extracts. Correlation analysis indicated that there was a linear relationship between the antioxidant potency, free radical scavenging ability and phenolic compounds content of the Chinese olive fruit extracts. Conclusions: Chinese olive fruit could be a natural candidate for studies of dietary complement to diabetes treatment since it combines antioxidant and antiglycation activities.

[HPLC fingerprint analysis of cordyceps and mycelium of cultured cordy].

OBJECTIVE: To establish HPLC fingerprints of cordyceps and mycelium of cultured cordy for quality control. METHOD: The analysis was carried out on a Diamonsil C18 column eluted with phosphate buffer (pH 6.5) and methanol as mobile phase, the gradient elution program was used, and the detection wavelength was 260 nm; The similarity of fingerprints was evaluated, then, cluster analysis was studied. RESULT: The method of HPLC fingerprint analysis was validated and in keeping with the requirement. Ten common peaks were found in HPLC fingerprint. Cordyceps from different areas and mycelium of cultured cordy could be distinguished by the HPLC fingerprint. CONCLUSION: All results above exhibit that this method is practicable, reproducible, and reliable as a method for the quality control of cordyceps and mycelium of cultured cordy at present.