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ABSTRACT: A new ester, armatuside (1), along with 13 known compounds (2-14), were obtained from the ethanolic extract of the heartwoods of Osmanthus armatus. The structures of all compounds were deduced using 1D, and 2D NMR spectroscopic methods. The absolute configuration of 1 was deduced by chemical correlation with a known compound. Compounds 2-14 were isolated from the plant for the first time.
Natural product research 06/2010; 24(10):948-52. · 1.01 Impact Factor
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ABSTRACT: Two new flavonol glycosides which contain rare alpha-D-galactose or alpha-D-glucose were obtained from the flowers of Rhododendron irroratum Franch., namely myricetin 3-O-beta-D-galactoside-3'-O-alpha-D-glucoside (1) and myricetin 3-O-beta-D-galactoside-3'-O-alpha-D-galactoside (2). Their structures were determined by UV, IR, HR-ESI-MS, ESI-MS, 1D- and 2D-NMR techniques.
Natural product research 06/2010; 24(10):920-5. · 1.01 Impact Factor
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ABSTRACT: We recently established that asparanin A, a steroidal saponin extracted from Asparagus officinalis L., is an active cytotoxic component. The molecular mechanisms by which asparanin A exerts its cytotoxic activity are currently unknown. In this study, we show that asparanin A induces G(2)/M phase arrest and apoptosis in human hepatocellular carcinoma HepG2 cells. Following treatment of HepG2 cells with asparanin A, cell cycle-related proteins such as cyclin A, Cdk1 and Cdk4 were down-regulated, while p21(WAF1/Cip1) and p-Cdk1 (Thr14/Tyr15) were up-regulated. Additionally, we observed poly (ADP-ribose) polymerase (PARP) cleavage and activation of caspase-3, caspase-8 and caspase-9. The expression ratio of Bax/Bcl-2 was increased in the treated cells, where Bax was also up-regulated. We also found that the expression of p53, a modulator of p21(WAF1/Cip1) and Bax, was not affected in asparanin A-treated cells. Collectively, our findings demonstrate that asparanin A induces cell cycle arrest and triggers apoptosis via a p53-independent manner in HepG2 cells. These data indicate that asparanin A shows promise as a preventive and/or therapeutic agent against human hepatoma.
Biochemical and Biophysical Research Communications 05/2009; 381(4):700-5. · 2.48 Impact Factor
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ABSTRACT: Seven new pentacyclic triterpenoid saponins, named dianversicosides A-G (1-7), together with nine known compounds, were isolated from the aerial parts of Dianthus versicolor. The structures of 1-7 were elucidated on the basis of spectroscopic data and chemical evidence. The absolute configuration of the 3-hydroxyl-3-methylglutaryl (HMG) group in 1-4 was ascertained by chemical analysis combined with a chiral HPLC method. Cytotoxic activities of the isolated compounds were evaluated against a small panel of cancer and other cell lines.
Journal of Natural Products 04/2009; 72(4):640-4. · 3.13 Impact Factor
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ABSTRACT: Three new pentasaccharide resin glycosides, batatosides III-V (1-3), were isolated from the roots of Sweet potato (Ipomoea batatas). Saponification of the crude resin glycoside mixture yielded substituents and simonic acid B. The structures of the isolated compounds (1-3) were established through spectroscopic analyses, including high field NMR spectroscopy and HR-ESI-MS, and chemical correlation. The major characteristics of 3 are the presence of three different substituents, especially the substituent of cinnamic acid was seldom. The monosaccharides of 1-3 were proved by GC-MS and the absolute configuration of aglycone was further established as S by Mosher's method with R-methyloxyphenylacetic acid (MPA) and S-MPA.
CHEMICAL & PHARMACEUTICAL BULLETIN 01/2009; 56(12):1670-4. · 1.59 Impact Factor
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ABSTRACT: One new (Sarsasapogenin O) and seven known steroids were isolated from the roots of Asparagus officinalis L. Their structures were elucidated on the basis of spectroscopic analysis, including various 2D-NMR techniques, hydrolysis, and by comparison of spectral data of known compounds. These compounds together with nine steroids which were previously isolated from this plant, were tested for cytotoxic activity. Among them, eight compounds displayed significant cytotoxicities against human A2780, HO-8910, Eca-109, MGC-803, CNE, LTEP-a-2, KB and mouse L1210 tumor cells.
Journal of Integrative Plant Biology 07/2008; 50(6):717-22. · 2.53 Impact Factor
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ABSTRACT: Solvothermal reaction of 5,10,10-trimethyl-bicyclo[2.2.1]-heptano-2-phenyl imidazole (TBHPI-H) with CuBr as a catalyst gave a one-dimensional infinite chain metal organic framework (MOF) ( 1) with the formulation {[( cis-(2C-2C)bi-TPHPI) 2( trans-(2C-2C)Bi-TPHPI)](Cu 2Br 2)(Cu 4Br 4)} n . The (2C-2C)bi-TPHPI ligand formed in situ was shown to be present as both the cis and trans C(2)−C(2) coupling isomers, which was confirmed by LC-MS analysis revealing two peaks at 19.96 and 21.65 min containing a peak at 503 Da assignable to the [M + H] + molecular ion fragment. To our knowledge, the trapping and structural characterization of such intermediates through formation of MOF complexes is unprecedented.
04/2008;
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ABSTRACT: Biotransformation of sinapic acid (1) with H2O2/Momordica charantia peroxidase, which exists in the widely used food M. charantia, at pH 5.0, 43 degrees C, in the presence of acetone resulted in six compounds, including four new compounds. Compound 2 was the first isolation of a new unique sinapic acid tetrameric derivate, which is formed by peroxidase catalysis in vitro. Besides 2, three other new sinapic acid dimers, 3-5 have also been isolated. Their structures were established on the basis of spectroscopic data. Compound 5 showed a stronger antioxidative activity than the parent sinapic acid (1). Compounds 4 and 5 significantly inhibited the growth of HL-60 cell at the concentration of 10-5 microl/L.
Journal of Agricultural and Food Chemistry 03/2007; 55(3):1003-8. · 2.82 Impact Factor
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ABSTRACT: Heat treatment of a solution of MeOH and water containing the quitenine ligand HQA [HQA = 6-methoxyl-(8S,9R)-cinchonan-9-ol-3-carboxylic acid] and ZnCl2 at 70 degrees C to give the one-dimensional (1D) chain coordination polymer {(HQA)(ZnCl2)(2.5H2O)}n (1). The local coordination geometry around the zinc center in 1 displays a slightly distorted tetrahedron, with the HQA ligand adopting a zwitterionic moiety similar to that found in natural amino acids. Measurements on a powdered sample of 1 reveal a strong second-harmonic-generation response of ca. 20 times larger than that for KDP (KH2PO4). Notably, measurements on the dielectric properties of 1 showed that the 1D chain coordination polymer exhibited a dipolar chain relaxation process and a high dielectric constant (epsilon0= 37.3).
Inorganic Chemistry 07/2006; 45(13):4868-70. · 4.60 Impact Factor
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ABSTRACT: The syntheses and luminescent properties of three novel zinc coordination polymers containing tetrazolyl ligands are described. In situ [2+3] cycloaddition reactions of acetonitrile or p-tolylnitrile with sodium azide in the presence of Zn(ClO(4))(2) as a Lewis acid (Demko-Sharpless tetrazole synthesis method) under hydrothermal (solvothermal) reaction conditions gave [Zn(CH(3)CN(4))(2)](3)(H(2)O) (1) and [Zn(4-MPTZ)(2)] (3) [4-MPTZ = 5-(4-methylphenyl)tetrazole], respectively. On the other hand, [Zn(HCN(4))(2)] (2) was obtained by directly reacting tetrazole with Zn(OAc)(2) under hydrothermal reaction conditions. The structure of 1 shows a super-diamond-like topological network with a diamond subunit as a connecting node. For 2, a diamond-like topological network is also found, but it is 2-fold interpenetrated. The structure of 3 reveals a 2D layered network with a hexagonal net, with the adjacent layers in the network stacked in an ABAB sequence. Photoluminescence studies revealed coordination polymers 1, 2, and 3 exhibit strong blue fluorescent emissions at lambda(max) = 396, 418, and 397 nm, respectively, in the solid state at room temperature.
Inorganic Chemistry 08/2005; 44(15):5278-85. · 4.60 Impact Factor
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ABSTRACT: The in situ hydrothermal reactions of ZnCl(2) with benzonitrile, 2-amino-5-cyanopyridine, and trans-2,3-dihydro-2-(4' '-cyanophenyl)-benzo[e]indole in the presence of NaN(3) and water afford two 3D-diamond-like networks, (CN(4)-C(6)H(5))(2)Zn (1) and (NH(2)-C(5)H(3)N-CN(4))(2)Zn (2), and one 2D square grid network, [(CN(4)-C(6)H(4)-C(12)H(7)N-C(5)H(4)N)(2)Zn].1.5H(2)O (3), in which these ligands gradually involve a noncenter-A-D (acceptor-donor) system, a one-center-A-D system, and a two-center-A-D system, respectively. All three compounds crystallize in noncentrosymmetric space groups (I2d for 1 and 2 and Fdd2 for 3) and display strong second harmonic generation (SHG) responses. Among the three new complexes, 3 shows the largest SHG effect, which is about 50 and 500 times that of urea and KDP (KH(2)PO(4)), respectively. The two-center-A-D system (multicenter push-pull electronic effect) in 3 may be responsible for it having the largest SHG effect. Interestingly, the three compounds exhibit strong fluorescent emissions at different wavelengths, 1 and 2 with blue fluorescent emissions at 390 and 415 nm and 3 with yellow-green fluorescent emissions at 495 and 532 nm.
Inorganic Chemistry 06/2005; 44(10):3618-25. · 4.60 Impact Factor
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ABSTRACT: The in situ hydrolysis of phthalyl--glutaminyl-histidine with Cd(ClO4)2·6H2O in the presence of water and methanol affords a novel two-dimensional cadmium coordination polymer, a new phase, anhydrous cadmium(II) phthalate, (1). The structure was determined by single crystal X-ray diffraction. Crystal data: P21/c, a = 13.8168(14), b = 7.0351(7), c = 8.2054(8) Å, β = 105.540(2)°, V = 768.43(13) Å3, Z = 4, R1 = 0.0380, wR2 = 0.1111.Zweidimensionales, wasserfreies Cadmium(II)-phthalatDie in situ-Hydrolyse von Phthalyl--glutaminyl-histidin mit Cd(ClO4)2·6H2O in Gegenwart von Wasser/Methanol ergibt ein neuartiges, zweidimensionales Cadmium-Koordinationspolymer - ein wasserfreis Cadmium(II)-phthalat, (1). Die Struktur wurde durch Einkristall-Röntgenstrukturanalyse bestimmt: Raumgruppe P21/c, a = 13.8168(14), b = 7.0351(7), c = 8.2054(8) Å, β = 105.540(2)°, V = 768.43(13) Å3, Z = 4, R1 = 0.0380, wR2 = 0.1111.
Zeitschrift für anorganische Chemie 08/2004; 630(11):1623 - 1626.
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ABSTRACT: We recently established that asparanin A, a steroidal saponin extracted from Asparagus officinalis L., is an active cytotoxic component. The molecular mechanisms by which asparanin A exerts its cytotoxic activity are currently unknown. In this study, we show that asparanin A induces G2/M phase arrest and apoptosis in human hepatocellular carcinoma HepG2 cells. Following treatment of HepG2 cells with asparanin A, cell cycle-related proteins such as cyclin A, Cdk1 and Cdk4 were down-regulated, while p21WAF1/Cip1 and p-Cdk1 (Thr14/Tyr15) were up-regulated. Additionally, we observed poly (ADP-ribose) polymerase (PARP) cleavage and activation of caspase-3, caspase-8 and caspase-9. The expression ratio of Bax/Bcl-2 was increased in the treated cells, where Bax was also up-regulated. We also found that the expression of p53, a modulator of p21WAF1/Cip1 and Bax, was not affected in asparanin A-treated cells. Collectively, our findings demonstrate that asparanin A induces cell cycle arrest and triggers apoptosis via a p53-independent manner in HepG2 cells. These data indicate that asparanin A shows promise as a preventive and/or therapeutic agent against human hepatoma.
Biochemical and Biophysical Research Communications.
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ABSTRACT: AimTo study the chemical constituents from the rhizome of Alpinia galangaMethodsSilica gel and Sephadex LH-20 column chromatographies were used to isolate the chemical constituents, and spectroscopic techniques were employed to elucidate their structures.ResultsA new phenylpropanoid was isolated from the rhizome of Alpinia galanga. Its structure was established as 4, 4′[(2E, 2′E)-bis(prop-2-ene)-1,1′-oxy]-diphenyl-7,7′-diacetata.ConclusionThe compound is a new phenylpropanoid.
Chinese Journal of Natural Medicines.
