Wei Qu

Phenols and flavonoids from the aerial part of Euphorbia hirta

AIM To investigate the chemical constituents of the aerial part of Euphorbia hirta Linn. METHODS The chemical constituents were isolated and purified by various chromatographic techniques, and their structures were elucidated on the basis of spectroscopic analysis. RESULTS Nine compounds were isolated and identified as scopoletin (1), scoparone (2), isoscopoletin (3), quercetin (4), isorhamnetin (5), pinocembrin (6), kaempferol (7), luteolin (8), gallic acid (9). CONCLUSION Among them compounds 1-3, 5-8 were found from this plant for the first time.

A New Diarylheptanoid from the Rhizomes of Alpinia officinarum

Abstract Aim To study the chemical constituents from the rhizomes of Alpinia officinarum Hance. Methods The chemical constituents were isolated with various chromatographic techniques, and their chemical structures were elucidated on the basis of spectral analysis. Results Five diarylheptanoids were obtained and their structures were identified as 5-ethoxyl-7-(4-hydroxy-3-methoxy-phenyl)-1-phenyl-3-heptanone ( 1 ), 5-hydroxy-1,7-diphenyl-3-heptanone ( 2 ), 5-hydroxy-7-(4-hydroxyl-3-methoxyphenyl)-1-phenyl-3-heptanone ( 3 ), 5-methoxy-7-(4-hydroxy-3-methoxyphenyl)-1-phenyl-3-heptanone ( 4 ), and ( E )-7-(4-hydroxy-3-methoxyphenyl)-1-phenylhept-4-en-3-one ( 5 ). Conclusion Compound 1 is a new diarylheptanoid.

A new dimeric diarylheptanoid from the rhizomes of Alpinia officinarum

AIM To study the chemical constituents of the rhizomes of Alpinia officinarum Hance. METHOD Compounds were isolated by repeated column chromatography, and their structures were elucidated on the basis of spectral analysis. The cytotoxic activities of these compounds were evaluated with the T98G and B16F10 cell lines by the MTT assay. RESULTS A dimeric diarylheptanoid, named alpinin B (1), along with three known diarylheptanoids were obtained, and their structures were identified as alpinin B (1), 1, 7-diphenyl-3,5-heptanedione (2), (4E)-1, 7-diphenylhept-4-en-3-one (3) and (4E)-7- (4-hydroxyphenyl)-1-phenylhept-4-en-3-one (4). CONCLUSION Compound 1 is a new dimeric diarylheptanoid. The biosynthetic pathway of 1 was speculated to originate from a Michael reaction between compounds 2 and 3. Compound 3 showed cytotoxicity against the human glioblastoma T98G cell line with IC50 of 27 μmol·L(-1).

Two new cassane diterpenoids from the seeds of Caesalpinia sappan Linn.

Abstract Aim To study the chemical components of the seeds of Caesalpinia sappan. Methods Compounds were isolated and purified by column chromatography. Their structures were elucidated on the basis of spectroscopic methods. In addition, the cytotoxic activity of these compounds were evaluated using SF-268, MCF-7 and HepG2 cell lines by the MTT assay. Results Four cassane diterpenoids were obtained and their structures were identified as phanginin L (1), phanginin M (2), phanginin I (3), phanginin G (4). Conclusion Phanginin L (1) and phanginin M (2) are new cassane diterpenoids. Compound 1 showed moderate cytotoxicity against HepG2 cell line with IC50 of 9.13 μg·mL−1.

Chemical Constituents from the Stems of Ilex pubescens var. glabra

Abstract Aim To study the chemical constituents from the stems of Ilex pubescens var. glabra . Methods The chemical constituents were isolated from the petroleum ether and EtOAc fractions and purified by various chromatographic methods. Their structures were elucidated on the basis of physical characteristics and spectral data. Results Ten compounds were obtained and their structures were identified as 3- O -β-D-galactopyranosyl-stigmasta-5, 25-diene ( 1 ), 5, 25-stigmastadien-3-ol ( 2 ), 3β-acetoxy-28-hydroxyurs-12-ene ( 3 ), oleanolic acid ( 4 ), β-sitosterol ( 5 ), betulinic acid ( 6 ), pomolic acid ( 7 ), syringic acid ( 8 ), β-daucosterol ( 9 ) and esculetin ( 10 ). Conclusion Compound 1 was isolated from this genus for the fist time and compounds 2–9 were firstly isolated from this plant.

YGS40, an active fraction of Yi-Gan San, reduces hydrogen peroxide-induced apoptosis in PC12 cells.

In our previous study, we have elucidated the chemical profile of YGS40, a fraction of Yi-Gan San (YGS), used for the treatment of Alzheimers disease (AD). Oxidative stress-induced apoptosis is implicated in neurodegenerative disorders such as AD. The aim of the present study was to explore the protective effects of YGS40 against hydrogen peroxide (H2O2)-induced apoptosis in PC12 cells and the underlying mechanisms. PC12 cells were exposed to 100 μmol·L(-1) of H2O2 for 12 h with or without YGS40 pretreatment. Cytotoxicity was determined by MTT (3, (4, 5-dimethylthiazole-2-yl) 2, 5-diphenyl-tetrazolium bromide) and lactate dehydrogenase (LDH) release assays; apoptosis was detected by Annexin V/propidium iodide coupled staining and by determining caspase-3 activity and Bax and Bcl-2 protein levels. Mitochondrial membrane potential (MMP) was assessed by the retention of rhodamine123; and the activities of superoxide dismutase (SOD) and malondialdehyde (MDA) were measured using commercially available enzymatic kits. Pretreatment with YGS40 significantly prevented H2O2-induced cytotoxicity and protected the cells against H2O2-triggered apoptosis characterized by externalization of membrane phosphatidylserine and caspase-3 activation and the increased ratio of Bax/Bcl-2 in PC12 cells. Further studies showed that YGS40 suppressed H2O2-induced MMP loss, increased SOD activity, and decreased MDA level. These findings suggest that YGS40 may be beneficial for the prevention and treatment of oxidative stress-mediated disorders.

A new quinoline alkaloid from the roots of Dictamnus angustifolius

AIM To investigate the quinoline alkaloids from the roots of Dictamnus angustifolius G.Don ex Sweet (Rutaceae). METHOD The quinoline alkaloids were isolated by various column chromatographic methods and their structures were elucidated on the basis of spectral analysis. RESULTS A new quinoline alkaloid, 5-methoxylrobustine (1), along with five known quinoline alkaloids were obtained, and their structures were identified as dictamnine (2), robustine (3), isopteleine (4), γ-fagarine (5), and skimmianine (6). Cytotoxicity testing of these alkaloids showed that all of them had weak cytotoxic activities against human breast cancer cells (MCF7). CONCLUSION Compound 1 is a new quinoline alkaloid. Alkaloid 3 showed stronger anti-proliferation effect than the other alkaloids.

Two new ortho benzoquinones from Uncaria rhynchophylla.

The present study was designed to determine the chemical constituents of the stems and hooks of Uncaria rhynchophylla. The chemical constituents were isolated and purified from CH2Cl2 fraction by chromatography. Their structures were elucidated by spectroscopic analyses. Their cytotoxicity was tested using MTT method. Two new ortho benzoquinones, 3-diethylamino-5-methoxy-1, 2-benzoquinone (1) and 3-ethylamino-5-methoxy-1, 2-benzoquinone (2), together with a known compound isorhynchophyllic acid (3) were isolated from U. rhynchophylla. These compounds were evaluated for their cytotoxicity against cancer cells A549, HepG2 and A2780. Compounds 1 and 2 were new ortho benzoquinones and showed weak antiproliferative activities on A549, HepG2 and A2780 cells. Compound 3 significantly inhibited the proliferation of A549, HepG2 and A2780 cells with IC50 values being 5.8, 12.8 and 11.8 µmol·L(-1), respectively.

A new β-carboline alkaloid from the seeds of Griffonia simplicifolia

AIM To study the chemical constituents from the seeds of Griffonia simplicifolia Baill. METHODS The chemical constituents were isolated and purified by a combination of chromatographic materials including silica gel, Sephadex LH-20, and preparative TLC. Their structures were elucidated on the basis of MS and NMR data analysis. The cytotoxic activities were evaluated against HepG2 cancer cell line using the MTT colorimetric method. RESULTS A new β-carboline alkaloid, griffonine (1), together with seven known alkaloids, hyrtioerectine B (2), 3-carboxy-6-hydroxy-β-carboline (3), hyrtiosulawesine (4), 5-hydroxyindole-3-carbaldehyde (5), 5-hydroxy-3-(2-hydroxyethyl) indole (6), trigonelline (7), and 5-hydroxytryptamine (8) were isolated and identified. Alkaloids 1, 2 and 4 showed growth inhibitory effects on the HepG2 cell line with IC50 values of 23.5, 9.6 and 19.3 μmol·L(-1), respectively. CONCLUSION Alkaloid 1 is new and was named griffonine. Alkaloids 2-7 were isolated from this plant for the first time. Alkaloids 1, 2 and 4 were potentially cytotoxic.

1-Methoxycarbony- β -carboline from Picrasma quassioides exerts anti-angiogenic properties in HUVECs in vitro and zebrafish embryos in vivo

Angiogenesis is a crucial process in the development of inflammatory diseases, including cancer, psoriasis and rheumatoid arthritis. Recently, several alkaloids from Picrasma quassioides had been screened for angiogenic activity in the zebrafish model, and the results indicated that 1-methoxycarbony-β-carboline (MCC) could effectively inhibit blood vessel formation. In this study, we further confirmed that MCC can inhibit, in a concentration-dependent manner, the viability, migration, invasion, and tube formation of human umbilical vein endothelial cells (HUVECs) in vitro, as well as the regenerative vascular outgrowth of zebrafish caudal fin in vivo. In the zebrafish xenograft assay, MCC inhibited the growth of tumor masses and the metastatic transplanted DU145 tumor cells. The proteome profile array of the MCC-treated HUVECs showed that MCC could down-regulate several angiogenesis-related self-secreted proteins, including ANG, EGF, bFGF, GRO, IGF-1, PLG and MMP-1. In addition, the expression of two key membrane receptor proteins in angiogenesis, TIE-2 and uPAR, were also down-regulated after MCC treatment. Taken together, these results shed light on the potential therapeutic application of MCC as a potent natural angiogenesis inhibitor via multiple molecular targets.