Showing papers in "Chemical & Pharmaceutical Bulletin in 1982"
TL;DR: It was found that intraperitoneal or oral administration of resveratrol or piceid reduced triglyceride synthesis from 14C-palmitate in the liver of mice and these stilbene components did not affect hormone-induced lipolysis in fat cells from rat eqididymal adipose tissue.
Abstract: The effects of the roots of Polygonum cuspidatum SIEB. et ZUCC. ("Kojo-kon" or "Itadori-kon" in Japanese) and its stilbene components (resveratrol and piceid) on lipid metabolism in rats and mice (higher animals) were investigated. Resveratrol and piceid inhibited the deposition of triglyceride and cholesterol in the liver of rats fed corn oil-cholesterol-cholic acid mixture. Piceid reduced the serum triglyceride and low density lipoprotein-cholesterol (LDL-ch) levels, and atherogenic index [total cholesterolhigh density lipoprotein-cholesterol (HDL-ch)/HDL-ch] in the oil mixture-fed rats. It was found that intraperitoneal or oral administration of resveratrol or piceid reduced triglyceride synthesis from 14C-palmitate in the liver of mice. In contrast, these stilbene components did not affect hormone-induced lipolysis in fat cells from rat eqididymal adipose tissue.
271 citations
TL;DR: The structure-activity relationship study showed that the 5-(4-oxybenzyl) moiety is essential for substantial activity in 5-substituted thiazolidine-2, 4-diones.
Abstract: More than 100 5-substituted thiazolidine-2, 4-diones were prepared and their hypoglycemic and hypolipidemic activities were evaluated with genetically obese and diabetic mice, yellow KK. The structure-activity relationship study showed that the 5-(4-oxybenzyl) moiety is essential for substantial activity. Among these compounds, 5-(4-cyclohexylmethoxy) benzylthiazolidine-2, 4-dione (47), 5-[4-(1-methylcyclohexylmethoxy) benzyl]-thiazolidine-2, 4-dione (49, ADD-3878) and 5-{4-[2-(3-pyridyl) ethoxy] benzyl} thiazolidine-2, 4-dione (59) exhibited the most favorable properties in terms of activity and toxicity.
260 citations
TL;DR: In this article, the authors synthesize benzoxazoles, benzothiazoles and benzimidazoles having substituents on the azole and benzene nuclei for antifungal, insecticidal and herbicidal activities.
Abstract: Benzoxazoles, benzothiazoles and benzimidazoles having substituents on the azole and benzene nuclei were synthesized evaluated for antifungal, insecticidal and herbicidal activities. It was found that benzimidazoles tended to exhibit antifungal activity while benzothiazoles tended to show herbicidal activity. Chloro, trifluoromethyl, methoxy and ethoxy groups at the 5 position were potent substituents, and the 2-pyridyl group at the 2 position is a common structural unit. Among several active derivatives, 7-chloro-2-(2-pyridyl) benzimidazole and 2-(2-pyridyl)-5-trifluoromethylbenzothiazole exhibited significant activity against Panonycus citri.
190 citations
TL;DR: In addition to [6]-gingerol four new constituents were isolated as potent inhibitors of prostaglandin (PG) biosynthesis from ginger, the roots of Zingiber officinale Roscoe.
Abstract: In addition to [6]-gingerol four new constituents were isolated as potent inhibitors of prostaglandin (PG) biosynthesis from ginger, the roots of Zingiber officinale Roscoe. Their structures were identified as [6]- and [10]-dehydrogingerdione (I and II) and [6]- and [10]-gingerdione (III and IV) by the interpretation of spectral data.
158 citations
TL;DR: In this paper, two new acyl glycosides, leucosceptosides A (IV) and B (V), have been isolated from Leucusceptrum japonicum (MIQ) and were determined to be 2-(3, 4-dihydroxyphenylethyl) 1-O-α-L-rhamnopyranosyl-(1→3)-β-D-(4-Ocaffeyl)-glucopyrano-glucophyranoside, respectively.
Abstract: Two new acyl glycosides, leucosceptosides A (IV) and B (V), have been isolated from Leucosceptrum japonicum (MIQ.) KITAMURA et MURATA, together with martynoside (III), acteoside (I) and an acteoside isomer (II). The structures of IV and V were determined to be 2-(3, 4-dihydroxyphenylethyl) 1-O-α-L-rhamnopyranosyl-(1→3)-β-D-(4-O-caffeyl)-glucopyranoside and 2-(3-hydroxy-4-methoxyphenylethyl) 1-O-α-L-rhamnopyranosyl-(1→3)-O-[β-D-apiofuranosyl (1→6)]-β-D-glucopyranoside, respectively, on the basis of chemical and spectral data.
142 citations
TL;DR: The profile of local anesthetic effect of dibucaine in microspheres in vivo was different from the release profile in vitro, and the more the amount of dIBucaine, the stronger was the localAnesthetic effect.
Abstract: DL-Polylactic acid microspheres containing dibucaine were prepared, and release patterns of dibucaine from the microspheres as well as the local anesthetic effects of the drug in the microspheres were examined. The influences of nonsolvents and dibucaine concentration at preparation on the characteristics and dibucaine contents of the microspheres were investigated. Higher pH in nonsolvents and higher dibucaine concentration at preparation resulted in increased dibucaine contents in the microspheres. The release patterns of dibucaine from microspheres varied significantly among microspheres with different dibucaine contents, and the release mechanisms of dibucaine from microspheres were greatly influenced by disintegration of the microspheres. The local anesthetic effects of 0.1 ml aliquots of dibucaine hydrochloride solutions were examined at four concentrations in vivo. Then, the local anesthetic effects of dibucaine in microspheres were compared with those of the above solutions in relation to the release rate of dibucaine from microspheres in vitro. The more the amount of dibucaine, the stronger was the local anesthetic effect. The local anesthetic effect of dibucaine in microspheres lasted much longer (300 h) than that of dibucaine hydrochloride solutions. The profile of local anesthetic effect of dibucaine in microspheres in vivo was different from the release profile in vitro.
136 citations
105 citations
TL;DR: A dosage form containing a local anesthetic for toothache was developed, using lidocaine as a model drug in HPC and CP as the peripheral base and the absorption when this dosage form was applied to the human gingiva was studied.
Abstract: In the present study, as a continuation of the previous work on a new mucosal dosage form for insulin using hydroxypropyl cellulose-H (HPC) and Carbopol-934 (CP), we attempted to develop a dosage form containing a local anesthetic for toothache, using lidocaine as a model drug in HPC and CP as the peripheral base. The dissolution profile of lidocaine was investigated with various mixing ratios of freeze-dried HPC/CP (FD-HPC/CP) to lidocaine in the core base, and the absorption when this dosage form was applied to the human gingiva was also studied. It was found that the rate in the dissolution test was delayed with increase in the amount of FD-HPC/CP in the core base and that the absorption of lidocaine was about 30% after 1 hour and then increased by about 10% of the initial amount per hour for 4 hours in preparations containing 5 and 10 mg of FD-HPC/CP.
94 citations
89 citations
TL;DR: A series of compounds bearing the 4-(2-methyl-2-phenylpropoxy) benzyl moiety was prepared and their hypoglycemic and hypolipidemic activities were evaluated with genetically obese and diabetic mice, yellow KK.
Abstract: A series of compounds bearing the 4-(2-methyl-2-phenylpropoxy) benzyl moiety was prepared and their hypoglycemic and hypolipidemic activities were evaluated with genetically obese and diabetic mice, yellow KK. Among these compounds, 5-[4-(2-methyl-2-phenylpropoxy) benzyl] thiazolidine-2, 4-dione (18, AL-321) was found to prossess hypoglycemic and hypolipidemic activities higher than or comparable to those of ethyl 2-chloro-3-[4-(2-methyl-2-phenylpropoxy) phenyl] propionate (1a). The acidic thiazolidine-2, 4-dione ring appeared to be essential for the activities.
87 citations
TL;DR: A new caffeoyl glycoside of β, 3, 4-trihydroxyphenethyl alcohol, designated as suspensaside (1), was isolated from the fruits of Forsythia suspensa VAHL (Oleaceae), and exhibited antibacterial activity against Staphylococcus aureus TERASHIMA.
Abstract: A new caffeoyl glycoside of β, 3, 4-trihydroxyphenethyl alcohol, designated as suspensaside (1), was isolated from the fruits of Forsythia suspensa VAHL (Oleaceae). The structure of 1 was established as DL-β, 3, 4-trihydroxyphenethyl-O-α-L-rhamnopyranosyl-(1→6)-4-O-caffeoyl-β-D-glucopyranoside on the basis of analysis of the carbon-13 nuclear magnetic resonance spectrum and chemical evidence. Compound 1 exhibited antibacterial activity against Staphylococcus aureus TERASHIMA. with MIC 4.1 mM (2.6 mg/ml).
TL;DR: In this article, five N-ethyl-N-(2-hydroxy-3-sulfopropyl) aniline derivatives have been synthesized and assessed as water-soluble hydrogen donors for the photometric determination of hydrogen peroxide in the presence of peroxidase.
Abstract: Five N-ethyl-N-(2-hydroxy-3-sulfopropyl) aniline derivatives have been synthesized and assessed as water-soluble hydrogen donors for the photometric determination of hydrogen peroxide in the presence of peroxidase. These compounds, sodium salts of N-ethyl-N-(2-hydroxy-3-sulfopropyl) aniline, N-ethyl-N-(2-hydroxy-3-sulfopropyl)-m-toluidine, N-ethyl-N-(2-hydroxy-3-sulfopropyl)-m-anisidine, 3, 5-dimethyl-N-ethyl-N-(2-hydroxy-3-sulfopropyl) aniline and 3, 5-dimethoxy-N-ethyl-N-(2-hydroxy-3-sulfopropyl)-aniline, gave high absorbances at visible wavelengths in media in the weakly alkaline to fairly acidic pH range. Further, the urea adduct of hydrogen peroxide could be conveniently used as a standard material.
TL;DR: Water-soluble polysaccharides, designated as GIa and GIb, were isolated from the bark of Melia azadirachta and their inhibiting effect on subcutaneously inoculated Sarcoma-180 was tested.
Abstract: Water-soluble polysaccharides, designated as GIa and GIb, were isolated from the bark of Melia azadirachta (Meliaceae) and their inhibiting effect on subcutaneously inoculated Sarcoma-180 was tested. GIa and GIb each gave a single peak on ultracentrifugation and gel filtration. Methylation, periodate oxidation and 13C-NMR spectroscopic studies suggested that GIa is composed of the following repeating unit ; α-D-Glc 1→4α-D-Glc 1→4α-D-Glc 1→4α-D-Glc 1→4α-D-Glc 6←1α-L-Araf. GIb is a branched arabinofucoglucan, containing a main chain of (1→4)-linked α-D-glucopyranosyl units substituted in the 6 position with side chains of α-L-arabinofuranosyl units. 3-O-substituted fucopyranose is attached to the α-(1→4) glucose units at the 4 position in the main chain.
TL;DR: Trimethylstannyl and bis derivatives of pyridine, quinoline, and isoquinoline were prepared from the corresponding halo and dihalo (chloro or bromo) derivatives and trimethyl stannyl sodium, which was generated in situ from chlorotrimethyl-stannane and sodium.
Abstract: Trimethylstannyl and bis (trimethylstannyl) derivatives of pyridine, quinoline, and isoquinoline were prepared from the corresponding halo and dihalo (chloro or bromo) derivatives and trimethylstannyl sodium, which was generated in situ from chlorotrimethyl-stannane and sodium. These stannyl derivatives readily underwent iododestannation on treatment with iodine to produce the corresponding iodo and diiodo derivatives of pyridine, quinoline, and isoquinoline, respectively, in good yields.
TL;DR: Two new biphenyl ether lignans were isolated from the leaves of Magnolia obovata THUNB and showed antibacterial activity against a cariogenic bacterium, Streptococcus mutans, but was less active than magnolol (5) and honokiol (6).
Abstract: Two new biphenyl ether lignans, named obovatol (1) and obovatal (2) were isolated from the leaves of Magnolia obovata THUNB. (Magnoliaceae) and their chemical structures were determined to be 4', 5-diallyl-2, 3-dihydroxybiphenyl ether and 3, 4-dihydroxy-5-(pallylphenoxy) cinnamic aldehyde by means of chemical and spectral studies. The former substance showed antibacterial activity against a cariogenic bacterium, Streptococcus mutans, but was less active than magnolol (5) and honokiol (6).
TL;DR: DL-Polylactic acid microspheres were prepared from three lots of PLA by a solvent-evaporation process and release patterns of butamben, tetracaine and dibucaine from these micro Spheres were examined.
Abstract: DL-Polylactic acid (PLA) microspheres were prepared from three lots of PLA by a solvent-evaporation process and release patterns of butamben, tetracaine and dibucaine from these microspheres were examined. As a first step, the physicochemical characteristics of three lots of PLA were examined. The release mechanism was examined by scanning electron microscopy. Microsphere characteristics and release patterns from the microspheres were dependent on both PLA characteristics and the local anesthetics used for the preparation.
TL;DR: The extent of racemization and the coupling efficiency during the coupling of benzyloxycarbonyl-L-phenylalanyl-Lvaline with L-proline tert-butyl ester were conveniently and rapidly determined by the use of high performance liquid chromatography with high accuracy.
Abstract: The extent of racemization and the coupling efficiency during the coupling of benzyloxycarbonyl-L-phenylalanyl-L-valine with L-proline tert-butyl ester were conveniently and rapidly determined by the use of high performance liquid chromatography with high accuracy. An extensive examination of various known coupling methods revealed that the coupling methods using diphenyl phosphorazidate (DPPA) and, especially, diethyl phosphorocyanidate (DEPC) afforded the best results. Reported results using DPPA and DEPC as peptide coupling reagents are also summarized (Table I).
TL;DR: It is suggested that chitin and chitosan may be suitable for use as diluents with friction-lowering properties in direct compression processes.
Abstract: As a part of a series of study on pharmaceutical applications of chitin and chitosan, the fluidity and compressibility of combined powders of lactose with chitin and chitosan, and potato starch with chitin and chitosan, as well as the disintegration properties of the tablets made from these powders were investigated in comparison with those of crystalline cellulose with lactose and potato starch. The lubricating properties of combined powders of lactose with chitin and chitosan were also investigated in comparison with those of lactose with crystalline cellulose. The fluidity of combined powders with chitin and chitosan was greater than that of the powder with crystalline cellulose. The hardest tablet was obtained with chitosan, followed by crystalline cellulose and chitin in that order. Tablets containing less than 70% of chitin or chitosan passed the disintegration test of JP X. The ejection force of the tablets of lactose/chitin and lactose/chitosan was significantly smaller than that of lactose/crystalline cellulose tablets. It is suggested that chitin and chitosan may be suitable for use as diluents with friction-lowering properties in direct compression processes.
TL;DR: Two new alkaloids, 4, 9-dimethoxy-1-vinyl-β-carboline (XI) and β-carbolin-1yl 3-(4, 8-dimethyltimethyl-4-methoxyβ-caroline-1]-1-yl)-1mETHoxypropyl ketone (XII) were isolated from the wood of Picrasma quassioides BENNET (Simaroubaceae) together with known alkaloid, 1.
Abstract: Two new alkaloids, 4, 9-dimethoxy-1-vinyl-β-carboline (XI) and β-carbolin-1-yl 3-(4, 8-dimethoxy-β-carbolin-1-yl)-1-methoxypropyl ketone (XII) were isolated from the wood of Picrasma quassioides BENNET (Simaroubaceae) together with known alkaloids, 1-ethyl-4-methoxy-β-carboline (VI), 4-methoxy-1-vinyl-β-carboline (VII), 4, 8-dimethoxy-1-vinyl-β-carboline (VIII), canthin-6-one (IX), and 5-methoxycanthin-6-one (X). The structures of these alkaloids were elucidated on the basis of spectroscopic evidence.
TL;DR: In this paper, a new class of flavan-3-ols substituted at the A-ring with a C6-C3 unit, together with caffeic acid (5) and (-)-epicatechin (6), have been isolated.
Abstract: As a result of an investigation of the relatively lower-molecular-weight phenolics in the bark of Cinchona succirubra (Rubiaceae), cinchonains Ia (1), Ib (2), Ic (3) and Id (4), a new class of flavan-3-ols substituted at the A-ring with a C6-C3 unit, have been isolated, together with caffeic acid (5) and (-)-epicatechin (6). The structures of these compounds have been established on the basis of chemical and spectroscopic evidence. A direct coupling of caffeic acid and (-)-epicatechin leading to the formation of cinchonains has also been achieved.
TL;DR: Balanophonin, a new neo-lignan was isolated from Balanophora japonica Makino and its structure and stereochemistry were determined by a combination of chemical method and extensive use of 1H and 13C-NMR spectrometry as discussed by the authors.
Abstract: Balanophonin, a new neo-lignan was isolated from Balanophora japonica Makino and its structure was discussed. Structure and stereochemistry were determined by a combination of chemical method and extensive use of 1H and 13C-NMR spectrometry.
TL;DR: Bioproduction of chaetoglobosins, novel type cytochalasans, by Chaetomium spp.
Abstract: Bioproduction of chaetoglobosins, novel type cytochalasans, by Chaetomium spp. was examined. Details of the culture conditions and methods for separation of the metabolites of Chaetomium globosum are presented. Some cytological effects of chaetoglobosins were also mentioned.
TL;DR: In this article, the root and rhizoma of Ledebouriella seseloides WOLFF (Umbelliferae), together with five known coumarins (1-5) and six known chromones (6, 7, 10, 11, 13 and 14).
Abstract: Three new chromones (8, 9, and 12), named 3'-O-angeloylhamaudol, ledebouriellol, and 4'-O-β-D-glucosyl-5-O-methylvisamminol, respectively, were isolated from the root and rhizoma of Ledebouriella seseloides WOLFF (Umbelliferae), together with five known coumarins (1-5) and six known chromones (6, 7, 10, 11, 13 and 14). The structures of 8, 9, and 12 were elucidated as (3S)-3, 4-dihydro-5-hydroxy-3-(2-methyl-2-butenyl) oxy-2, 2, 8-trimethyl-2H, 6H-benzo [1, 2-b : 5, 4-b'] dipyran-6-one, (3S)-3, 4-dihydro-2, 2-dimethyl-5-hydroxy-8-hydroxymethyl-3-(2-methyl-2-butenyl) oxy-2H, 6H-benzo [1, 2-b : 5, 4-b'] dipyran-6-one, and (2S)-2, 3-dihydro-2-(1-β-D-glucopyranosyloxy-1-methylethyl)-4-methoxy-7-methyl-5H-furo [3, 2-g] [1] benzopyran-5-one, respectively, by chemical and spectral studies.
TL;DR: In this paper, three diarylheptanoids were isolated as inhibitors of prostaglandin biosynthesis from the methanol extract of Alpinia offioinarum Hance.
Abstract: Three new diarylheptanoids were isolated as inhibitors of prostaglandin biosynthesis from the methanol extract of Alpinia offioinarum Hance. Their structures were elucidated to be 7-(4 "-hydroxy-3"-methoxyphenyl)-1-phenyl-3, 5-heptadione (I), 5-methoxy-7-(4 "-hydroxy-3"-methoxyphenyl)-1-phenyl-3-heptanone (IV), and 5-hydroxy-7-(4"-hydroxyphenyl)-1-phenyl-3-heptanone (VI) by the interpretation of spectral data.
TL;DR: A short step synthesis of cyclopentatrienylidene retinals [(9)-(11)] is reported and the formation of the novel rhodopsin analogue from the isomer is described.
Abstract: A short step synthesis of cyclopentatrienylidene retinals [(9)-(11)] is reported and the formation of the novel rhodopsin analogue (12) from the isomer (9) is described.
TL;DR: In this paper, the structures of momordicosides K and L, bitter principles in the fruits of Momordica charantia L, were elucidated as 7-O-β-D-glucopyranosides of 3β, 7β-dihydroxy-25-methoxy-cucurbita-5, 23-dien-19-al, respectively.
Abstract: The structures of momordicosides K and L, bitter principles in the fruits of Momordica charantia L. (Cucurbitaceae), were elucidated as 7-O-β-D-glucopyranosides of 3β, 7β-dihydroxy-25-methoxy-cucurbita-5, 23-dien-19-al and 3β, 7β, 25-trihydroxy-cucurbita-5, 23-dien-19-al, respectively, from spectral and chemical evidence.
TL;DR: The structures of three triterpenoidal saponins, onjisaponins A (1), B (2) and E (3), were determined on the basis of spectral and chemical evidence as mentioned in this paper.
Abstract: The structures of three triterpenoidal saponins, onjisaponins A (1), B (2) and E (3), were determined on the basis of spectral and chemical evidence as presenegenin-(3)-β-D-glucopyranosido-(28)-2-O-{[β-D-apio-D-furanosyl (1→3)] [β-D-galactopyranosyl (1→4)-β-D-xylopyranosyl (1→4)]-α-L-rhamnopyranosyl}-3-O-(α-L-rhamnopyranosyl)-4-O-(4'-methoxy-cinnamoyl)-β-D-fucopyranoside, presenegenin-(3)-β-D-glucopyranosido-(28)-2-O-[β-D-galactopyranosyl (1→4)-β-D-xylopyranosyl (1→4)-α-L-rhamnopyranosyl]-3-O-(α-L-rhamnopyranosyl)-4-O-(4'-methoxycinnamoyl)-β-D-fucopyranoside (=senegin III) and presenegenin- (3)-O-β-D-glucopyranosido-(28)-2-O-[β-D-galactopyranosyl (1→4)-β-D-xylopyranosyl (1→4)-α-L-rhamnopyranosyl]-4-O-(3', 4', 5'-trimethoxycinnamoyl)-β-D-fucopyranoside, respectively. The 13C nuclear magnetic resonance spectra of onjisaponins A, B, E and their derivatives were investigated and each carbon signal was assigned as shown in Table I.
TL;DR: The structures of soyasapogenols A, B, and E, three of five hitherto isolated sapogenols of soybean (Glycine max Merrill), were re-investigated based on the chemical and X-ray analyses as discussed by the authors.
Abstract: The structures of soyasapogenols A, B, and E, three of five hitherto isolated sapogenols of soybean (Glycine max Merrill), were re-investigated. Based on the chemical and X-ray analyses, it has been shown that the structures of soyasapogenols A, B, and E should be partly revised respectively from 1', 2', and 3'to 1, 2, and 3 and consequently the structures of soyasaponins I, II, and III are expressed as 6, 7, and 8.
TL;DR: A new caffeoyl glycoside of 3, 4-dihydroxy-β-phenethyl alcohol, designated as forsythiaside (1), was isolated from the fruits of Forsythia suspensa VAHL (Oleaceae).
Abstract: A new caffeoyl glycoside of 3, 4-dihydroxy-β-phenethyl alcohol, designated as forsythiaside (1), was isolated from the fruits of Forsythia suspensa VAHL (Oleaceae). The structure of 1 is proposed to be 3, 4-dihydroxy-β-phenethyl-O-α-L-rhamnopyranosyl-(1→6)-4-O-caffeoyl-β-D-glucopyranside on the basis of analysis of the carbon-13 nuclear magnetic resonance spectrum.