Showing papers in "Chemical & Pharmaceutical Bulletin in 1985"
TL;DR: Antioxidative components in the methanol extract of the rhizome of Curcuma longa L. were investigated by using the evaluation method based on the air oxidation of linoleic acid.
Abstract: Antioxidative components in the methanol extract of the rhizome of Curcuma longa L. were investigated by using our evaluation method based on the air oxidation of linoleic acid. Curcuminoids such as curcumin, 4-hydroxycinnamoyl (feruloyl) methane and bis (4-hydroxycinnamoyl) methane were found to be active components. Curcumin was the most active component and its 50% inhibitory concentrations for the air oxidation of linoleic acid were 1.83×10-2% (thiobarbituric acid value) and 1.15×10-2% (peroxide value). These values of curcumin are superior to those of dl-α-tocopherol.
307 citations
TL;DR: The present paper deals with the rate of in vitro degradation of PLA microcapsules in various environmental conditions.
Abstract: In recent years, the use of polylactide (PLA), a synthetic biodegradable polymer, as drug-loaded matrix has been examined in the hope that the matrix will decay and decompose after releasing the drug in a sustained manner over a long period of time in the human body[1–8]. However, no detailed work has been done on the degradation rate of PLA even under in vitro conditions. The present paper deals with the rate of in vitro degradation of PLA microcapsules in various environmental conditions.
208 citations
TL;DR: It appears that EVAI copolymer can be used as a membrane for controlling the release of 5-FU or adriamycin and matrices containing anticancer agent could be useful vehicles for implanted delivery systems for anticancer agents.
Abstract: Ethylene-vinyl alcohol (EVAI) copolymer was evaluated as a vehicle for controlled or sustained release of 5-fluorouracil (5-FU) and adriamycin. The variation of initial drug concentration and, to an even greater extent, the variation in comonomer ratio affected the drug release rate as well as the cumulative amount of the drug released. An increase in the ethylene content of the EVAI copolymer decreased drug release. It appears that EVAI copolymer can be used as a membrane for controlling the release of 5-FU or adriamycin. The antitumor activity of EVAI copolymer matrices containing these anticancer agents was evaluated against Ehrlich ascites carcinoma (EAC) in mice on the basis of changes in body weight and animal survival data. Tumor cell injections were performed on day 0 and matrix implantations on day 3, both intraperitoneally. The suppressive effect of matrices containing anticancer agents on the increase in body weight was higher than that of the free drugs. A prolongation of the life span of tumor-bearing mice following implantation of therapeutic matrices was also noted. Implantation of the EVAI copolymer matrix containing an anticancer agent was less effective against the P388 leukemia than the EAC. These results suggest that EVAI copolymer matrices containing anticancer agents may be effective in cancer chemotherapy. Matrices composed of EVAI copolymer could be useful vehicles for implanted delivery systems for anticancer agents.
167 citations
165 citations
TL;DR: A series of piperazinylalkyl esters bearing a lipophilic substituent on the 4-nitrogen of the piperazine ring was synthesized and tested for hypotensive effect in spontaneously hypertensive rats (SHR).
Abstract: In a search for new 1, 4-dihydropyridine derivatives with a long-lasting effect on the cardiovascular system, a series of piperazinylalkyl esters (I) bearing a lipophilic substituent on the 4-nitrogen of the piperazine ring was synthesized and tested for hypotensive effect in spontaneously hypertensive rats (SHR). Compounds I, especially those having a diphenylmethyl moiety on the piperazine ring, showed extremely potent and long-lasting hypotensive properties. Analogues related to I were also prepared, and the structure-activity relationships are discussed.
150 citations
TL;DR: Methods for the preparation of polymorphs of indomethacin (IMC) were studied and it was concluded that the transformation followed kinetics corresponding to two-dimensional growth of nuclei (Avrami equation), and the activation energy was calculated to be 14.2 kcal/mol from the Arrhenius plot.
Abstract: Methods for the preparation of polymorphs of indomethacin (IMC) were studied in order to obtain the pure polymorphs. The physicochemical properties of IMC polymorphs were measured by using X-ray diffraction analysis. infrared (IR) spectroscopy, differential thermal analysis (DTA) and differential scanning calorimetry (DSC), and two polymorphs (α and γ forms) and one benzene solvate (β form) were identified. The pure α form was obtained when distilled water at room temperature was poured into IMC ethanol solution at about 80°C, and the precipitated crystals were filtered off and dried. The pure β and γ forms were obtained by recrystallization from benzene and ethyl ether, respectively, at room temperature. The melting points of the α and γ forms were 148 and 154°C, respectively, and their heats of fusion were 7.49±0.27 and 8.64±0.13kcal/mol, respectively, as determined by DSC. A mixture of α and γ forms was obtained by the method previously reported for α form preparation ("recrystallization method"), since the pure α form was transformed to the γ form in ethanol at room temperature. The transformation of α form to γ form in ethanol was analyzed by the kinetic method using 9 kinds of kinetic models. It was concluded that the transformation followed kinetics corresponding to two-dimensional growth of nuclei (Avrami equation), and the activation energy was calculated to be 14.2 kcal/mol from the Arrhenius plot. The solubilities of the α and γ forms in distilled water were 0.87 and 0.69mg/100ml, respectively.
148 citations
TL;DR: The results suggest that the changes of glucokinase and glucose-6-phosphatase levels probably represent one of the mechanisms of the hypoglycemic action produced by ginsenoside-Rb2.
Abstract: The effect of ginsenoside-Rb2 purified from ginseng was examined in streptozotocin-induced diabetic rats. The rats of the ginsenoside-Rb2-treated group showed a significant decrease of blood glucose level. A moderate (but statistically insignificant) increase in the hepatic glycogen content was observed. Furthermore, the ginsenoside-Rb2-treated group showed a significant rise of glucokinase activity in the liver, while there was a significant decrease in the activity of glucose-6-phosphatase. These results suggest that the changes of glucokinase and glucose-6-phosphatase levels probably represent one of the mechanisms of the hypoglycemic action produced by ginsenoside-Rb2.
125 citations
TL;DR: Chitosan might be useful as a vehicle for a sustained-release preparation of indomethacin in granular form for the formulation of sustained- release preparations of various drugs.
Abstract: The use of chitosan granules as a means to achieve sustained release of indomethacin was examined. In contrast with the rapid dissolution of indomethacin in powdered form, sustained but almost complete release from chitosan granules was observed. A unique characteristic of the chitosan granules was that they gradually swelled and floated on the acid medium at pH 1.2. This floating property of the granules on the acid medium can be applied to the formulation of sustained-release preparations of various drugs. The effect of cross-linking procedure on the drug release patterns from chitosan granules was also examined. The release rate of the drug from the granules could be controlled by varying the cross-linking procedure. Thus, chitosan might be useful as a vehicle for a sustained-release preparation of indomethacin in granular form.
111 citations
TL;DR: Caffeic acid and chlorogenic acid inhibited the elevation of serum triglyceride, lipid peroxides, total cholesterol, glutamic oxaloacetic Transaminase and glutamic pyruvic transaminase, as well as liver lipid peroxide.
Abstract: The effects of oral administration of the extracts from the leaves of several Artemisia species, and of chlorogenic acid, which is one of their components, and also of caffeic acid (which can be produced by partial hydrolysis of caffeoylquinic acids, which are the main polyphenolic components in these species) on lipid metabolic injury produced in rats by feeding peroxidized oil were investigated. The acetone-water extracts of the leaves of Artemisia princeps, A. montana and A. capillaris reduced the elevation of lipid peroxide concentration in the serum in peroxidized oil-fed rats, and the above extracts reduced the levels of liver triglyceride. The extracts of A. montana and A. capillaris inhibited the elevation of serum glutamic oxaloacetic transaminase and glutamic pyruvic transaminase. Caffeic acid and chlorogenic acid also inhibited the elevation of serum triglyceride, lipid peroxides, total cholesterol, glutamic oxaloacetic transaminase and glutamic pyruvic transaminase, as well as liver lipid peroxide.
103 citations
TL;DR: The crystal structure of aspirin has been redetermined by X-ray diffraction analysis at room temperature by taking account of the non-rigidity of the molecule and applying the condition of vanishing stress.
Abstract: The crystal structure of aspirin has been redetermined by X-ray diffraction analysis at room temperature. The lattice energy, the eleastic constants and the structure parameters corresponding to the equilibrium of a model potential of aspirin crystal have been calculated by taking account of the non-rigidity of the molecule and applying the condition of vanishing stress. The model potential consists of the exp-6 type dispersion and exchange repulsion terms, the Lippincott type hydrogen bond stretching terms and the electrostatic interaction terms between fixed atomic charges. The atomic coordinates of the calculated structure agree well with those determined crystallographically.
101 citations
TL;DR: In this article, a new lignan glycoside was isolated from the bark of Eucommia ulmoides OLIV, and its structure was established as (+)-1-hydroxypinoresinol 4"-O-β-D-glucopyranoside (1) on the basis of chemical evidence and spectroscopic studies.
Abstract: A new lignan glycoside was isolated from the bark of Eucommia ulmoides OLIV. (Eucommiaceae) and its structure was established as (+)-1-hydroxypinoresinol 4"-O-β-D-glucopyranoside (1) on the basis of chemical evidence and spectroscopic studies. An isomer of 1, (+)-1-hydroxypinoresinol 4'-O-β-D-glucopyranoside (2), was also isolated, together with (±)-erythro-, and (±)-threo-guaiacylglycerol (3 and 4), (+)-cyclo-olivil (5) and (-)-olivil (6).
TL;DR: In this paper, 13 carbazole alkaloids were isolated from Murraya euchrestifolia HAYATA (Rutaceae) collected in Taiwan and the structures were elucidated from spectral data and chemical transformations.
Abstract: Thirteen carbazole alkaloids were isolated from Murraya euchrestifolia HAYATA (Rutaceae) collected in Taiwan. Four of them are novel carbazolequinones [murrayaquinone-A (7), -B (8), -C (9), and -D (10)], isolated for the first time from natural sources. Three of others are new alkaloids having the normal carbazole nucleus [murrayafoline-A (1), -B (2), and (+)-murrayazoline (11)]. These structures were elucidated from spectral data and chemical transformations.
TL;DR: The present results suggest that the application of alkyl glycoside vesicles as drug carriers may be feasible and show longer lives on stage in an ampule at 20°C than phosphatidylcholine vesicle.
Abstract: It was observed that alkyl glycosides formed lamellar vesicles like phosphatidylcholine vesicles (liposomes), and the application of these vesicles as drug carriers was attempted. Various alkyl glycosides were synthesized and vesicles were prepared with these glycosides. The encapsulation capacity of the vesicles was examined in relation to alkyl chain length, sugar moiety, and lipid composition. The glucosides of myristyl, cetyl, and stearyl alcohols formed vesicles, but those of lauryl, decyl, and octyl alcohols did not. The vesicles of glucoside, galactoside, and mannoside showed fairly good encapsulation capacity but those of lactoside showed low capacity. An appropriate ratio of glycoside, cholesterol, and dicetylphosphate is an important factor for the formation of these vesicles, especially with regard to dicetylphosphate. The alkyl glycoside vesicles show longer lives on stage in an ampule at 20°C than phosphatidylcholine vesicles. The stability in plasma was also examined. The glycoside vesicles showed rapid release of about 40% of the aqueous contents, but after that, they showed outstanding stability for 48h in plasma at 37°C. On the other hand, phosphatidylcholine vesicles showed rapid release of only about 30%, but they disintegrated gradually and showed low encapsulation capacity (about 20%) after 48h. The present results suggest that the application of alkyl glycoside vesicles as drug carriers may be feasible.
TL;DR: Results suggest that Chrysosplenium plants, which contain large amounts of chrysosplenol B and chrysomethoxyl C, may be useful as medicinal herbs against the common cold caused by rhinovirus infection.
Abstract: The antiviral activity of a wide range of naturally occurring flavonoids was investigated in vitro. Chrysosplenol B and chrysosplenol C, which are contained specifically in Chrysosplenium plants, and axillarin showed potent antiviral activity, especially against rhinovirus. A comparison of the activities of the compounds tested indicated that 3-methoxyl and 5-hydroxyl groups in the flavone skeleton were both necessary for antiviral activity against rhinovirus, and the activity may also be affected by various groups at other positions. The other flavonoids tested had little or no antiviral activity against herpes simplex virus, influenza virus and rhinovirus. These results suggest that Chrysosplenium plants, which contain large amounts of chrysosplenol B and chrysosplenol C, may be useful as medicinal herbs against the common cold caused by rhinovirus infection. These plants have not so far been used as a medicinal herb or as a folk medicine, as far as is known.
TL;DR: The determination of relative astringency (RA) and relative affinity to methylene blue (RMB), based on those of geraniin (RAG and RMBG), shows good reproducibility with small amounts of samples for the estimation of the tannin content of plant extracts, and has been applied to the evaluation of the basal activity of 84 tannins and related compounds.
Abstract: The determination of relative astringency (RA) and relative affinity to methylene blue (RMB), based on those of geraniin (RAG and RMBG), shows good reproducibility with small amounts of samples for the estimation of the tannin content of plant extracts, and has been applied to the evaluation of the basal activity of 84 tannins and related compounds. The values obtained for polyphenols of lower molecular weight, which are not regarded as tannins, were zero or almost zero. An increase of these two values of up to about 1.3-1.4 times with increase of molecular weight of polyphenols (particularly such increase due to galloylation) was observed for each type of tannin tested. The RMBG determination gives values somewhat larger than the RAG values for hydrolyzable tannins, and rather smaller than the RAG values for condensed tannins.
TL;DR: Four bisabolane sesquiterpenoids, α-curcumene, ar-turmerone, β-atlantone and xanthorrhizol, were isolated as major antitumor constituents (against Sarcoma 180 ascites in mice) from the rhizomes of Curcuma xanth orrhiza from the spectroscopic evidence.
Abstract: Four bisabolane sesquiterpenoids, α-curcumene, ar-turmerone, β-atlantone and xanthorrhizol, were isolated as major antitumor constituents (against Sarcoma 180 ascites in mice) from the rhizomes of Curcuma xanthorrhiza. Their structures were deduced from spectroscopic evidence. The antitumor effectivenes was rated (+ + +) for α-curcumene, (+ +) for ar-turmerone and (+ +) for xanthorrhizol at 50 mg/kg in the total packed cell volume method.
TL;DR: The 1, 3-dipolar cycloaddition of an intermediary iminium ylide formed from N-benzyl-N-(methoxymethyl) trimethylsilylmethylamine to conjugated olefinic and acetylenic dipolarophiles in the presence of a catalytic amount of trifluoroacetic acid has been found to give 3 or 3, 4-substituted pyrrolidines and 2, 5-dihydropyrroles.
Abstract: The 1, 3-dipolar cycloaddition of an intermediary iminium ylide formed from N-benzyl-N-(methoxymethyl) trimethylsilylmethylamine to conjugated olefinic and acetylenic dipolarophiles in the presence of a catalytic amount of trifluoroacetic acid has been found to give 3-or 3, 4-substituted pyrrolidines and 2, 5-dihydropyrroles.
TL;DR: The metabolites and degradation products of 2-amino-7-isopropyl-5-oxo-5H-[1] benzopyrano-[2, 3-b] pyridine-3-carboxylic acid were synthesized to confirm the proposed structures and to determine their activity in the rat passive cutaneous anaphylaxis test.
Abstract: The metabolites and degradation products of 2-amino-7-isopropyl-5-oxo-5H-[1] benzopyrano-[2, 3-b] pyridine-3-carboxylic acid (Amoxanox, AA-673, 1), a promising drug for the treatment of bronchial asthma, were synthesized to confirm the proposed structures and to determine their activity in the rat passive cutaneous anaphylaxis test.
TL;DR: It is suggested that the hyaluronidase might be present as one of the target enzymes of the influent calcium ions in the mast cells and might directly control the degranulation.
Abstract: Modulation of hyaluronidase activities by various compounds which are closely related with the degranulation of the mast cells was studied. It was found that compound 48/80, a non-specific histamine releaser from mast cells, activated hyaluronidase strongly. Hyaluronidase activated by CaCl2 or compound 48/80 was inhibited by anti-allergic agents such as disodium cromoglycate (DSCG) or tranilast. On the other hand, tranilast greatly enhanced the activity of the hyaluronidase activated by NaCl. The inhibitory effects of these anti-allergic agents on the activation of the inactive hyaluronidase were shown to be stronger than those on activated hyaluronidase. Since the hyaluronidase activity was modulated by compounds closely associated with allergic phenomena, it is suggested that the hyaluronidase might be present as one of the target enzymes of the influent calcium ions in the mast cells and might directly control the degranulation.
TL;DR: The terpenoid constituents of Ganoderma lucidum (Fr.) KARST (Polyporaceae) and their structures were determined on the basis of spectral data and some chemical interconversions as discussed by the authors.
Abstract: Eight new terpenoid constituents named ganoderenic acids A (1), B (2), C (3) and D (4), ganoderic acids E (5), F (6), and G (7), and lucidenic acid D (8) were isolated from dried fruiting bodies of the fungus, Ganoderma lucidum (Fr.) KARST (Polyporaceae) and their structures were determined on the basis of spectral data and some chemical interconversions.
TL;DR: The anticoagulative principles were isolated from Curcumae Rhizoma by a combination of partition and column chromatographies on silica gel, and identified as 1, 7-bis (4-hydroxy-3-methoxyphenyl)-1, 6-heptadiene-3, 5-dione (curcumin), p, p'-dihydroxydicinnamoylmethane and p-Hydroxycinnamoys
Abstract: The anticoagulative principles were isolated from Curcumae Rhizoma by a combination of partition and column chromatographies on silica gel, and identified as 1, 7-bis (4-hydroxy-3-methoxyphenyl)-1, 6-heptadiene-3, 5-dione (curcumin), p, p'-dihydroxydicinnamoylmethane and p-hydroxycinnamoylferuloylmethane. During the isolation process plasma recalcification time in mice was used to follow the anticoagulative activity of the material.
TL;DR: Through screening of various strains of intestinal bacteria from human feces, Peptostreptococcus anaerobius was shown to have potent ability to transform paeoniflorin to pae onimetaboline I.
Abstract: In the course of studies on the metabolism of active components of crude drugs by intestinal bacteria, paeoniflorin, oxypaeoniflorin, and benzoylpaeoniflorin isolated from the roots of Paeonia albiflora PALLAS (Paeoniaceae) were incubated with a human fecal suspension. Paeoniflorin, as well as oxypaeoniflorin and benzoylpaeoniflorin, was converted to three metabolites (paeonimetabolines I, II and III) by intestinal bacteria. The structure of the major metabolite (paeonimetaboline I) was elucidated by spectroscopic methods. Through screening of various strains of intestinal bacteria from human feces, Peptostreptococcus anaerobius was shown to have potent ability to transform paeoniflorin to paeonimetaboline I.
TL;DR: Of the fifteen compounds isolated, cinnamylphenols, isoflavans, is oflavene and benzoic acid derivative significantly inhibited prostaglandin biosynthesis as well as platelet aggregation induced by arachidonic acid.
Abstract: he root heartwood of Dalbergia odorifera T. CHEN (Leguminosae) is a Chicese medicinal drug (Japanese name koshinko) used for a stagnant blood syndrome (stagnation of disordered blood; Japanese, oketsu). In addition to 10 known compounds, five new phenolic compounds, isomucronustyrene and hydroxyobtustyrene (cinnamylphenols), (+)-isoduartin (isoflavan), odoriflavene (isoflav-3-ene) and (-)-odoricarpan (pterocarpan) were isolated and their structures were elucidated on the basis of chemical and spectroscopic methods. Of the fifteen compounds isolated, cinnamylphenols, isoflavans, isoflavene and benzoic acid derivative significantly inhibited prostaglandin biosynthesis as well as platelet aggregation induced by arachidonic acid.
TL;DR: The results suggest that many tannins may possess anti-inflammatory activity and anti-allergic activity.
Abstract: The inhibitory effects of tannins on the activation of inactive hyaluronidase and on the degranulation from rat mesentery mast cells induced by compound 48/80 were investigated. Among the tested tannins, 1, 2, 3, 4, 6-penta-O-galloylglucose, 1, 2, 3, 6-tetra-O-galloylglucose (hydrolyzable tannins) and 3, 3'-di-O-galloylprodelphinidin B-2 (condensed tannins) showed the strongest inhibitory effects in both cases. These results suggest that many tannins may possess anti-inflammatory activity and anti-allergic activity.
TL;DR: On prepare une serie de derives de l'acide deshydroabietique avec un groupement hydrophile (amino, carbamoyl, carb amoyloxy, ureido, sulfamoyL, ou sulfo) sur les positions 12 et/ou 18 and on teste leur activite antiulcereuse.
Abstract: On prepare une serie de derives de l'acide deshydroabietique avec un groupement hydrophile (amino, carbamoyl, carbamoyloxy, ureido, sulfamoyl, ou sulfo) sur les positions 12 et/ou 18 et on teste leur activite antiulcereuse
TL;DR: A series of N-acyl amino acid analogues of 2 (1H)-quinolinone was synthesized and tested for antiulcer activity against acetic acid-induced gastric ulcer in rats, and 2-(4-chlorobenzoylamino)-3-[2 ( 1H-quinolinon-4-yl] propionic acid (VIIIf) was found to have the most potent activity.
Abstract: A series of N-acyl amino acid analogues of 2 (1H)-quinolinone was synthesized and tested for antiulcer activity against acetic acid-induced gastric ulcer in rats. These compounds were synthesized by the acylation of amino acid derivatives of 2 (1H)-quinolinone, which were obtained from the reaction of ω-bromoalkyl 2 (1H)-quinolinones and acetamidomalonate in the presence of sodium ethoxide, followed by hydrolysis with diluted hydrochloric acid. Among them, 2-(4-chlorobenzoylamino)-3-[2 (1H)-quinolinon-4-yl] propionic acid (VIIIf) was found to have the most potent activity. The structure-activity relationships are discussed.
TL;DR: It was confirmed that the physicochemical state ofSolid dispersions plays a predominant role in the dissolution of the drug from the solid dispersions.
Abstract: Enteric coating agents, such as hydroxypropylmethylcellulose phthalate, methacrylic acidmethacrylic acid methyl ester copolymer, cellulose acetate phthalate, carboxymethylethylcellulose, were investigated as possible carriers for poorly water-soluble drugs in solid dispersions. In most cases, the drugs were present in amorphous form in the solid dispersions of 1 : 3 weight ratio of drug to polymer, though griseofulvin and phenytoin were not. Dissolution behavior was investigated using nifedipine, griseofulvin or spironolactone as a drug. The amorphous solid dispersions showed supersaturation phenomena in JPX 2nd fluid (pH 6.8), but the dissolution rate was suppressed in JPX 1st fluid (pH 1.2). It was confirmed that the physicochemical state of solid dispersions plays a predominant role in the dissolution of the drug from the solid dispersions.
TL;DR: Two novel 2-arylbenzofuran derivatives named mulberrofurans F and G were isolated from the ethyl acetate extract of the root bark of cultivated mulberry tree (Japanese name "Roso", a cultivated variety of Morus lhou KOIDZ).
Abstract: Two novel 2-arylbenzofuran derivatives named mulberrofurans F and G (=albanol A), as well as albanol B (3), were isolated from the ethyl acetate extract of the root bark of cultivated mulberry tree (Japanese name "Roso, " a cultivated variety of Morus lhou KOIDZ.). The structures of mulberrofurans F and G were shown to be 1 and 2, respectively, on the basis of spectral and chemical evidence. Mulberrofurans F (1) and G (2) were derived from chalcomoracin (4) and mulberrofuran C (5), respectively, by photocyclization in acidic solution. The compounds (1, 2, and 3) are optically active and can be regarded biogenetically as variations of Diels-Alder type adducts of chalcone derivatives and a dehydroprenyl-2-arylbenzofuran derivative. Intravenous injection of mulberrofuran F (1), as well as G (2), caused a marked depressor effect in rabbit.