ABSTRACT
A macroporous styrene-divinylbenzene copolymer containing N-methylglucamine groups was selected for a new 68Ge/68Ga generator system. This resin packed into a column effectively adsorbed the parent nuclide 68Ge. The daughter 68Ga was eluted from the resin with a solution of a low-affinity gallium chelating ligand such as citric or phosphoric acid. The 68Ge leakage was less than 0.0004% of the 68Ge adsorbed on the resin. By simple mixing of transferrin and desferoxamine conjugated HSA and IgG with the eluate from the column, 68Ga-labeling was completed in high yield.
Subject(s)
Gallium Radioisotopes/chemistry , Germanium/chemistry , Meglumine/chemistry , Polymers/chemistry , Radionuclide Generators , Adsorption , Blood Proteins/chemistry , Chromatography, Affinity/methods , Electrophoresis, Cellulose Acetate , Gamma Rays , Humans , Hydrogen-Ion Concentration , Isotope Labeling , Nuclear Magnetic Resonance, Biomolecular , Radiopharmaceuticals/chemistryABSTRACT
The substitution of gallic acid at the 3 position of (-)-epigallocatechin-3-O-gallate (EGCG) increased the inhibition against topoisomerase I from calf thymus gland and topoisomerase II from human placenta, and the substitution of a hydroxyl group at the 3' position increased the inhibition against the topoisomerase I. These results suggested that the 3 and 3' positions of the EGCG molecule play important roles in the process of inhibition of topoisomerases I and II. EGCG showed strong inhibition against topoisomerases I from wheat germ, calf thymus gland and Vero cells, and showed weak or no inhibition against topoisomerases I from carcinoma cells such as A549, HeLa and COLO 201 cells. EGCG differentially inhibited the topoisomerases I from different sources.
Subject(s)
Catechin/pharmacology , Enzyme Inhibitors/pharmacology , Topoisomerase I Inhibitors , Topoisomerase II Inhibitors , Animals , Catechin/analogs & derivatives , Catechin/chemistry , Cattle , DNA Topoisomerases, Type I/chemistry , DNA Topoisomerases, Type II/chemistry , DNA, Superhelical/drug effects , Humans , Structure-Activity Relationship , Tea/chemistryABSTRACT
A novel inhibitor of topoisomerase I designated as isoaurostatin (1) was isolated from the culture filtrate of Thermomonospora alba strain No. 1520. The structure of 1 was determined to be 6,4'-dihydroxyisoaurone on the basis of spectroscopic (NMR and MS) methods. Compound 1 inhibited the relaxation activity of calf thymus topoisomerase I in a noncompetitive manner and did not inhibit the relaxation and decatenation of human placenta topoisomerase II. Compound 1 is an inhibitor belonging to cleavable complex-nonforming type without DNA intercalation.
Subject(s)
Actinomycetales/chemistry , Benzofurans/isolation & purification , Enzyme Inhibitors/isolation & purification , Topoisomerase I Inhibitors , Animals , Benzofurans/pharmacology , Cattle , DNA Topoisomerases, Type II/metabolism , Enzyme Inhibitors/pharmacology , Humans , Kinetics , Magnetic Resonance Spectroscopy , Mass Spectrometry , Models, Chemical , Placenta/enzymology , Protein Conformation , Thymus Gland/enzymologyABSTRACT
We investigated whether capsianosides, diterpene glycosides, extracted from Capsicum plants could affect human immunodeficiency virus type 1 (HIV-1) infection. Significant effect on virus infection in MAGI/CCR5 cells was neither observed for the X4 virus by capsianosides II, XI, and A, nor for an R5 virus by capsianoside G. Apparent enhancement of X4 HIV-1 infection by capsianoside G was observed and exclusively related to the usage of the CXCR4 coreceptor. The capsianoside G-treated cells had no change in the expression level of CD4, CXCR4, and CCR5, however, colocalization and capping of CD4 and CXCR4, but not of CD4 and CCR5 was observed. Our results suggested that capsianoside G enhanced X4 virus infection at the level of viral penetration through the capping and colocalization of receptors needed for infection.
Subject(s)
CD4 Antigens/drug effects , CD4 Antigens/physiology , Diterpenes/pharmacology , HIV Infections/etiology , HIV Infections/immunology , HIV-1/pathogenicity , Oligosaccharides/pharmacology , Receptors, CXCR4/drug effects , Receptors, CXCR4/physiology , Adsorption , Capsicum/chemistry , Cell Line , DNA, Viral/genetics , Diterpenes/chemistry , Glycosides/chemistry , Glycosides/pharmacology , HIV-1/drug effects , HIV-1/genetics , HeLa Cells , Humans , Oligosaccharides/chemistry , Plants, Medicinal , Proviruses/drug effects , Proviruses/genetics , Receptor Aggregation/drug effects , Transcription, Genetic/drug effects , TransfectionABSTRACT
A new flavonol glycoside, kaempferol 3-O-alpha-L-rhamnopyranosyl -(1-->6)-[alpha-L-rhamnopyranosyl-(1-->2)]-beta-D-galactopyranosyl-7-O-a lpha-L-rhamnopyranoside, named astrasikokioside I, was isolated from aerial part of Astragalus shikokianus, together with two flavonol glycosides, kaempferol 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-galactopyranosyl-7-O-alpha-L- rhamnopyranoside, robinin, and three triterpenoid glycosides, soyasaponin I, sophoraflavoside II and robinioside E.
Subject(s)
Flavonoids/isolation & purification , Oligosaccharides/isolation & purification , Rosales/chemistry , Saponins/isolation & purification , Chromatography, Thin Layer , Flavonoids/chemistry , Oligosaccharides/chemistry , Plant Extracts/chemistry , Saponins/chemistryABSTRACT
Two new cardiac glycosides called cheiranthosides VI (2) and VII (3) were isolated together with a known one, glucoerysimoside (1) from the seeds of Erysimum cheiranthoides. Based on spectroscopic data, the structures of 2 and 3 were characterized as periplogenin 3-O-beta-D-glucopyranosyl(1-->4)-beta-D-fucopyranoside and periplogenin 3-O-beta-D-glucopyranosyl(1-->4)-beta-D-antiaropyranoside, respectively.
Subject(s)
Cardiac Glycosides/isolation & purification , Plants, Medicinal/chemistry , Carbohydrate Sequence , Chromatography, Thin Layer , Magnetic Resonance Spectroscopy , Methanol/chemistry , Molecular Sequence Data , Seeds/chemistry , Solvents , Spectrometry, Mass, Fast Atom BombardmentABSTRACT
Solasodine glycosides were analyzed for the selection of higher-producing natural resources in the fruits of Solanum spp. by western blotting and ELISA using anti-solamargine monoclonal antibody (MAb). Western blotting of Solanum khasianum showed a correlation with the analysis by ELISA. The results indicated that the fruits of S. khasianum contained the highest level of solasodine glycosides, compared to other species having 53.43 +/- 3.90 microg/mg dry wt. The high level of solasodine glycosides in S. khasianum suggests that it may be suitable for commercial production.
Subject(s)
Antibodies, Monoclonal , Phytosterols/immunology , Solanaceae/chemistry , Solanaceous Alkaloids/analysis , Solanaceous Alkaloids/immunology , Blotting, Western , Calibration , Carbohydrate Sequence , Cross Reactions , Enzyme-Linked Immunosorbent Assay , Fruit/chemistry , Glycosides/analysis , Humans , Molecular Sequence DataABSTRACT
Two new methyltransferase inhibitors were isolated from the culture filtrate of Streptomyces sp. strain No. 1513 and named 1513-DMIa and 1513-DMIb. 1513-DMIa and 1513-DMIb were distinguished in certain properties from DMI-1, DMI-2, DMI-3 and DMI-4 previously reported. The molecular weight of 1513-DMIa and 1513-DMIb were estimated to be 576 and 8400 from the results of FAB-MS and gel filtration, respectively. The inhibitory activities of 1513-DMIa and 1513-DMIb were shown to be pH- and temperature-dependent and both inhibited M. EcoRI in an uncompetitive manner with respect to DNA or S-adenosylmethionine (SAM).
Subject(s)
Enzyme Inhibitors/chemistry , Site-Specific DNA-Methyltransferase (Adenine-Specific)/antagonists & inhibitors , Streptomyces/metabolism , Chromatography, Gel , DNA-Cytosine Methylases/antagonists & inhibitors , Deoxyribonuclease EcoRI/antagonists & inhibitors , Enzyme Inhibitors/isolation & purification , Enzyme Inhibitors/pharmacology , Kinetics , Molecular Structure , Molecular Weight , Nuclear Magnetic Resonance, Biomolecular , Spectrometry, Mass, Fast Atom Bombardment , Streptomyces/chemistryABSTRACT
PURPOSE: The aim of this study was to investigate the characteristics of the structural transitions and changes in ligand binding properties of different albumins during the pH-dependent structural transition, often referred to as the N-B transition. METHODS: Structural transitions were evaluated by means of spectrometry, differential scanning calorimetry and chemical modification. In addition, ligand binding properties were investigated using typical site-specific bound drugs (warfarin, phenylbutazone, ibuprofen and diazepam). RESULTS: Conformational changes, including N-B transition, clearly occurred in albumins from all species used in this study. The conformational stabilities of all the albumins were clearly lost in the weakly alkaline pH range. This was probably the result of the destruction of salt bridges between domain I and domain III in the albumin molecule. In addition, the profiles of the ANS-induced fluorescence were different and could be classified into two patterns, suggesting that hydrophobic pockets in the albumin molecules were different for the different species. The data suggest that the amino acid residues responsible for the transitions were some of the His residues located in domain I. Further, the ligand binding properties of the albumins were slightly different but statistically significant. CONCLUSIONS: The overall mechanisms of the N-B transition may be similar for all the albumins, but its impact is considerably different among the species in terms of both structural characteristics and ligand binding properties. Furthermore, the transitions appear to be multi-step transitions.
Subject(s)
Serum Albumin, Bovine/chemistry , Serum Albumin/chemistry , Animals , Binding Sites , Cattle , Diazepam/metabolism , Dogs , Histidine/chemistry , Humans , Hydrogen-Ion Concentration , Ibuprofen/metabolism , Ligands , Phenylbutazone/metabolism , Protein Conformation , Rabbits , Rats , Serum Albumin/metabolism , Serum Albumin, Bovine/metabolism , Species Specificity , Warfarin/metabolismABSTRACT
Topostatin is a new topoisomerase inhibitor isolated from the culture filtrate of Thermononospora alba strain No. 1520. The inhibitor inhibits topoisomerases I and II, and it has neither ability to stabilize the cleavable complex nor ability to intercalate into DNA strands. The molecular formula of topostatin was determined as C36H58N4O11S based on the FAB-MS analyses, and the structure was elucidated to be a novel 14-membered ring containing peptide and terpenoid by various NMR spectroscopies.
Subject(s)
Enzyme Inhibitors/chemistry , Enzyme Inhibitors/pharmacology , Lactams/chemistry , Lactams/pharmacology , Topoisomerase I Inhibitors , Topoisomerase II Inhibitors , Molecular StructureABSTRACT
Cytotoxic activities of 20 steroidal glycosides obtained from Solanum genera plants were examined against various cell lines to provide new evidence as follows: 1) As regarding the sugar linkage, the glycosides possessing a beta-chacotriosyl moiety were the most effective and the presence of the terminal rhamnosyl residue was required for exhibiting strong activity. 2) As for the aglycone, the glycosides carrying a spirostanol aglycone showed the strongest activity and even an aglycone without a sugar linkage presented considerably strong activity.
Subject(s)
Antineoplastic Agents/pharmacology , Glycosides/pharmacology , Steroids/pharmacology , Drug Screening Assays, Antitumor , Drugs, Chinese Herbal/pharmacology , Glycosides/chemistry , Humans , Molecular Structure , Plant Extracts/chemistry , Plant Extracts/pharmacology , Solanum tuberosum , Steroids/chemistry , Tumor Cells, CulturedABSTRACT
Three new cardiac glycosides were isolated along with two known cardenolides from the seeds of Erysimum cheiranthoides. The new ones were characterized by spectral methods as 16 beta-hydroxystrophanthidin (strophadogenin) 3-O-beta-glucopyranosyl-(1-->4)-beta-boiviopyranoside, strophadogenin 3-O-alpha-rhamnopyranosyl-(1-->4)-beta-digitoxopyranoside and strophanthidin 3-O-alpha-rhamnopyranosyl-(1-->4)-beta-digitoxopyranoside, named cheiranthosides I, II and III, respectively.
Subject(s)
Cardenolides/isolation & purification , Plants, Medicinal/chemistry , Carbohydrate Sequence , Cardenolides/chemistry , Magnetic Resonance Spectroscopy , Medicine, Chinese Traditional , Molecular Sequence Data , Spectrometry, Mass, Fast Atom BombardmentABSTRACT
Serum specimens were assayed for human T-lymphotropic virus type II(HTLV-II) infection in 1,500 individuals known to be seropositive for HTLV-I and 30,000 blood donors in Japan. All HTLV-I-positive individuals were negative for HTLV-II. However, one of the blood donors was clearly seropositive for HTLV-II. Further, the donor was shown to be positive for HTLV-IIb. Here we report at least one case with HTLV-II in Japan and discuss the origin of the infection.
Subject(s)
HTLV-II Infections/blood , Human T-lymphotropic virus 2 , Adult , Base Sequence , DNA, Viral/analysis , Enzyme-Linked Immunosorbent Assay , HTLV-I Infections/blood , HTLV-I Infections/epidemiology , HTLV-II Infections/epidemiology , Human T-lymphotropic virus 2/genetics , Humans , Japan/epidemiology , Male , Molecular Sequence DataABSTRACT
From the leaves of Thevetia peruviana four new flavonol glycosides, kaempferol 3-glucosyl(1 --> 4) [6"'-sinapoylglucosyl] (1 --> 2) galactoside and 3-[2""-sinapoylglucosyl](1 --> 4)[6"'-sinapoylglucosyl](1 --> 2)galactoside and kaempferol and quercetin 3-[6"'-sinapoylglucosyl](1 --> 2)galactoside were isolated, together with the known compounds, kaempferol and quercetin 3-glucosyl(1 --> 2)galactoside. The glycosides were characterized from FAB mass, 1H and 13C NMR and UV spectral data.
Subject(s)
Flavonoids/chemistry , Glycosides/chemistry , Carbohydrate Conformation , Carbohydrate Sequence , Flavonoids/isolation & purification , Flavonols , Glycosides/isolation & purification , Magnetic Resonance Spectroscopy , Molecular Sequence Data , Plant Leaves , Spectrometry, Mass, Fast Atom Bombardment , Spectrophotometry, UltravioletABSTRACT
C-nor-D-homo-homologues of cannogenin and uzarigenin glycosides were isolated along with known cardenolide glycosides from the frozen fresh leaves of Thevetia neriifolia. A bisdesmosidic tetraoside of 3 beta,14,21-trihydroxy-5 beta,14 beta-pregnan-20-one was also obtained from the polar fraction and the structure established.
Subject(s)
Cardenolides/isolation & purification , Glycosides/isolation & purification , Plants, Medicinal/chemistry , Saponins/isolation & purification , Magnetic Resonance Spectroscopy , Plant Leaves/chemistry , Spectrometry, Mass, Fast Atom BombardmentABSTRACT
Four new steroidal glycosides, named capsicosides A-D together with proto-degalactotigonin, were isolated from the roots and seeds of Capsicum annuum var. conoides and Capsicum annuum var. fasciculatum. On the basis of detailed chemical and spectroscopic evidence, the structures of capsicosides A-D were shown to be furostanol glycosides corresponding to gitogenin and tigogenin oligoglycosides. Capsicoside A was regarded as the same compound as the previously described capsicoside, whose structure now needs to be revised according to the data presented in this report.
Subject(s)
Capsicum/chemistry , Glycosides/isolation & purification , Phytosterols/isolation & purification , Plants, Medicinal , Carbohydrate Sequence , Glycosides/chemistry , Magnetic Resonance Spectroscopy , Molecular Sequence Data , Phytosterols/chemistry , Spectrometry, Mass, Fast Atom BombardmentABSTRACT
Six new ergostane glycosides, designated as petunioside A, petunioside B, 24-epipetunioside B, petunioside C, 24-epipetunioside C and petunioside D, were isolated from the methanolic extract of the fresh aerial parts of Petunia hybrida. Their structures were determined by means of spectroscopic analysis and single crystal X-ray analysis.
Subject(s)
Ergosterol/chemistry , Glycosides/chemistry , Plants/chemistry , Carbohydrate Conformation , Carbohydrate Sequence , Crystallography, X-Ray , Ergosterol/analogs & derivatives , Ergosterol/isolation & purification , Glycosides/isolation & purification , Magnetic Resonance Spectroscopy , Models, Molecular , Molecular Conformation , Molecular Sequence Data , Spectrometry, Mass, Fast Atom BombardmentABSTRACT
The chemical structures of four cyclic peptides, lyciumins A-D (1-4), three acyclic diterpene glycosides, lyciumosides I-III (5-7) and other three compounds, a tryptophan derivative glycoside (8), a monoterpene glycoside (9) and a steroidal glycoside (10) isolated from Lycium chinense, have been elucidated by a combination of chemical, 1H- and 13C-NMR, and mass spectrometric studies. Lyciumins are interesting because of their monocyclic octapeptides containing a novel C-N linkage between tryprophan N1 and glycine C alpha.
Subject(s)
Diterpenes/chemistry , Glycosides/chemistry , Peptides, Cyclic/chemistry , Plants, Medicinal/chemistry , Amino Acid Sequence , Amino Acids/analysis , Diterpenes/isolation & purification , Glycosides/isolation & purification , Magnetic Resonance Spectroscopy , Molecular Sequence Data , Peptides, Cyclic/isolation & purificationABSTRACT
The structures of two new steroidal glycosides named soladulcosides A and B, isolated from the aerial parts of Solanum dulcamara including new sapogenols, were elucidated as (22R, 25R)-3 beta, 15 alpha, 23 alpha-trihydroxy-5 alpha-spirostan-26-one 3-O-alpha-L-rhamnopyranosyl-(1----2)-beta-D-glucopyranoside and (22R, 25R)-3 beta,23 alpha-dihydroxy-5 alpha-spirostan-26-one 3-O-alpha-L-rhamnopyranosyl-(1----2)-[alpha-L-rhamnopyranosyl-(1----4)]- beta-D-glucopyranoside, respectively.
