Showing papers in "Chemical & Pharmaceutical Bulletin in 1983"
TL;DR: In this article, the identification of three new monomeric acylated flavan-3-ols (asinensins A and B) from green tea leaves was confirmed.
Abstract: Along with four dimeric proanthocyanidin gallates, viz. prodelphinidin B-2 3'-O-gallate (IV) and procyanidins B-2 3, 3'-di-O-gallate (V), B-2 3'-O-gallate (VI) and B-4 3'-O-gallate (VII), two novel dimeric flavan-3-ol gallates (VIII and IX) named theasinensins A and B, in which two flavan units are linked at the B-ring, have been isolated from fresh green tea leaves, and their structures have been established on the basis of spectroscopic evidence in conjunction with enzymatic hydrolyses with tannase. Three new monomeric acylated flavan-3-ols have also been isolated, and their structures were similarly characterized as (-)-epigallocatechin 3-O-p-coumaroate (I), (-)-epigallocatechin 3, 3'-di-O-gallate (II) and (-)-epigallocatechin 3, 4'-di-O-gallate (III). In addition, the occurrence of the known (-)-epicatechin 3-O-gallate (X), (-)-epigallocatechin 3-O-gallate (XI), (+)-catechin (XII), (-)-epicatechin (XIII), (-)-epigallocatechin (XIV) and (-)-epicatechin 3-O-(3-O-methyl)-gallate (XV) in green tea leaves was confirmed.
257 citations
TL;DR: Some monomeric polyphenols, represented by (-)-epigallocatechin gallate, showed inhibitory effects stronger than those of the condensed tannins in these systems, particularly on the lipid peroxidation induced by ADP and NADPH.
Abstract: The inhibitory effects of 25 tannins and related compounds on the lipid peroxidation induced by adenine 5'-diphosphate (ADP) and ascorbic acid in rat liver mitochondria, and on that induced in rat liver microsomes by ADP and nicotinamide adenine dinucleotide phosphate (NADPH), were determined. All of the tannins, except for some polyphenols of low molecular weight and methylated polyphenols, showed significant inhibition in these two systems at the concentration of 1μg/ml. Almost complete inhibition of the lipid peroxidation in the two systems was shown by some ellagitannins such as pedunculagin, isoterchebin, etc., at the dose of 5μg/ml. Marked differences of the inhibitory activities were observed among the tannins depending on the tannin structure, including the stereoisomerism in the monomer of condensed tannin, and on the experimental system used. The inhibitory effects of most of the hydrolyzable tannins were higher than those of the condensed tannins in both systems. Some monomeric polyphenols, represented by (-)-epigallocatechin gallate, showed inhibitory effects stronger than those of the condensed tannins in these systems, particularly on the lipid peroxidation induced by ADP and NADPH. The inhibitory effects of these tannins in both systems were very much stronger than that of α-tocopherol.
216 citations
TL;DR: Xanthine oxidase (XO) inhibitors were isolated from the flowers and buds of Daphne genkwa SIEB and were identified as genkwanin (1), apigenin (2), luteolin 7-methyl ether (3) and lutenolin (4).
Abstract: Xanthine oxidase (XO) inhibitors were isolated from the flowers and buds of Daphne genkwa SIEB. et ZUCC. (Thymelaeaceae) and were identified as genkwanin (1), apigenin (2), luteolin 7-methyl ether (3) and luteolin (4). Compounds 2 and 4 showed particularly strong inhibitory activity against XO. The modes of inhibition by 2 and 4 with respect to xanthine as a substrate were of mixed type. This is the first report of isolation of 3 and 4 from these flowers and buds.
169 citations
TL;DR: It is concluded that in human tumors a thymidine phosphorylase activity converts 5'-DFUR to 5-fluorouracil, an activated form.
Abstract: Activities of pyrimidine nucleoside phosphorylases were assayed in extracts of human tumors, normal tissues of the same organs and tumors of mice (Sarcoma-180) and guinea pigs (Line-10), with thymidine (dThd), uridine (Urd), and 5'-deoxy-5-fluorouridine (5'-DFUR) as substrates. The nucleoside cleaving activities were higher in extracts of human tumor tissues than in those of normal tissues of the same organs. In human tissues, phosphorolytic activitiy towards dThd was high, while that towards Urd was low. In animal tumors, Urd was the best substrate. 1-(2'-Deoxy-β-D-glucopyranosyl)-thymine (GPT), a specific inhibitor of uridine phosphorylase, inhibited the phosphorolysis of Urd and 5'-DFUR in extracts of animal tumors, but not that of dThd and 5'-DFUR in extracts of human tumors. A thymidine phosphorylase preparation was partialy purified from human lung cancer. Km values of the preparation were 2.43×10-4 M and 1.69×10-3 M for dThd and 5'-DFUR, respectively. We conclude that in human tumors a thymidine phosphorylase activity converts 5'-DFUR to 5-fluorouracil, an activated form.
139 citations
TL;DR: In this paper, a new lignan diglycoside was isolated from the bark of Eucommia ulmoides OLIV. (Eucommiaceae) and its structure was established as (+)-medioresinol di-O-β-D-glucopyranoside (1) by means of chemical and spectral studies.
Abstract: A new lignan diglycoside was isolated from the bark of Eucommia ulmoides OLIV. (Eucommiaceae) and its structure was established as (+)-medioresinol di-O-β-D-glucopyranoside (1) by means of chemical and spectral studies. (+)-Pinoresinol di-O-β-D-glucopyranoside (2), liriodendrin (3) and (+)-pinoresinol O-β-D-glucopyranoside (4) were also isolated.
128 citations
TL;DR: In this paper, the main chemical constituents of anthraquinone glycosides were also obtained from the roots of Rubia cordifolia, and the structures were established by various chemical and spectroscopic methods.
Abstract: From Radix Rubiae (dried roots of Rubia cordifolia), mollugin, 1-hydroxy-2-methyl-9, 10-anthraquinone, alizarin, 1, 3-dihydroxy-2-ethoxymethyl-9, 10-anthraquinone, lucidin primeveroside, ruberythric acid and three new anthraquinones, 2-methyl-1, 3, 6-trihydroxy-9, 10-anthraquinone, 2-methyl-1, 3, 6-trihydroxy-9, 10-anthraquinone 3-O-(6'-O-acetyl)-α-rhamnosyl-(1→2)-β-glucoside and 2-methyl-1, 3, 6-trihydroxy-9, 10-anthraquinone 3-O-α-rhamnosyl (1→2)-β-glucoside, were isolated. The new anthraquinone glycosides were also obtained from the roots of R. akane, as the main chemical constituents of anthraquinone glycosides. The structures were established by various chemical and spectroscopic methods.
124 citations
TL;DR: It was proved that ginsenoside Rg1 was not significantly metabolized in the liver, and the decomposition and/or metabolism of ginseng saponins in rat stomach and large intestine were confirmed.
Abstract: The pharmacokinetic charactor of ginsenoside Rg1, one of the main saponins of ginseng (Panax ginseng C.A. MEYER), was investigated in rats by using thin-layer chromatography (TLC) and a dual-wavelength TLC scanner. Ginsenoside Rg1 was absorbed rapidly from the upper parts of the digestive tract (accounting for 1.9-20.0% of the dose of Rg1 administered orally). The serum level of ginsenoside Rg1 reached its peak at 30 min, and the maximum levels of ginsenoside Rg1 in tissues were attained within 1.5 h. However, ginsenoside Rg1 was not found in the brain. Ginsenoside Rg1 was excreted into rat urine and bile in a 2 : 5 ratio. It was also proved that ginsenoside Rg1 was not significantly metabolized in the liver. However, the decomposition and/or metabolism of ginsenoside Rg1 in rat stomach and large intestine were confirmed.
112 citations
TL;DR: Three peptide-like yellow compounds (1, 2, 3) containing a guanidine moiety, one of which (named hymenialdisine, 2) is a monobrominated derivative, and six 3β-hydroxymethyl-A-norsterane derivatives [purified as the acetates] were isolated from the Okinawan marine sponge Hymeniacidon aldis and their structures were elucidated on the basis of physicochemical evidence including the X-ray crystallographic analysis of 2.
Abstract: Three peptide-like yellow compounds (1, 2, 3) containing a guanidine moiety, one of which (named hymenialdisine, 2) is a monobrominated derivative, and six 3β-hydroxymethyl-A-norsterane derivatives [purified as the acetates : 4a, 5a, 6a, 7a (a mixture of two compounds), and 8a] were isolated from the Okinawan marine sponge Hymeniacidon aldis and their structures were elucidated on the basis of physicochemical evidence including the X-ray crystallographic analysis of 2.
102 citations
TL;DR: In this article, the triterpene-oligoglycosides were isolated from the root of Korean Astragalus membranaceus BUNGE and the structure of astragaloside IV was elucidated.
Abstract: Twelve triterpene-oligoglycosides were isolated from the glycosidic constituents of Astragali Radix, the root of Korean Astragalus membranaceus BUNGE. (Leguminosae). They were acetylastragaloside I (3), isoastragalosides I (5) and II (7), astragalosides I (4, major), II (6), III, IV (8), V, VI and VII, which contain a 9, 19-cyclolanostane cycloastragenol (1) as the aglycone, and astragaloside VIII and soyasaponin I (9), which possess an oleanene-type aglycone, soyasapogenol B. By means of chemical degradations, which included a selective cleavage method for the glucuronide linkage, and 13C-NMR examinations, the structure of astragaloside IV was elucidated as 3-O-β-D-xylopyranosyl-6-O-β-D-glucopyranosylcycloastragenol (8). In addition, the structures of five acetyl derivatives of 8 : acetylastragaloside I, astragaloside I, isoastragaloside I, astragaloside II and isoastragaloside II, were elucidated as 3-O-β-(2', 3', 4'-tri-O-acetyl)-D-xylopyranosyl- (3), 3-O-β-(2', 3'-di-O-acetyl)-D-xylopyranosyl- (4), 3-O-β-(2', 4'-di-O-acetyl)-D-xylopyranosyl- (5), 3-O-β-(2'-O-acetyl)-D-xylopyranosyl- (6) and 3-O-β-(3'-O-acetyl)-D-xylopyranosyl-6-O-β-D-glucopyranosylcycloastragenol (7), respectively.
100 citations
TL;DR: There was no significant difference in % release of B.B.FCF after 12 h from ointments containing glycerin and polyethylene glycol (PEG) as excipients, and the release rate was related to the consistency of CP gel ointment rather than to water absorption.
Abstract: A new type of highly viscous ointment containing Carbopol-934 (CP) for application to the oral mucosa was formulated. The release properties of Brilliant Blue FCF (B.B.FCF) and the absorption of sodium salicylate through the oral mucosa from the ointment were studied. In release test using the agar gel bed method, there was no significant difference in % release of B.B. FCF after 12 h from ointments containing glycerin and polyethylene glycol (PEG) as excipients. However, the form of the ointment containing glycerin was maintained for 24 h whereas the ointment containing PEG liquefied. The 50% release time (T50) decreased with increase of glycerin content, but the difference of water absorption was negligible. Therefore, the release rate of B.B. FCF was related to the consistency of CP gel ointment rather than to water absorption. In vivo absorption of sodium salicylate from the ointment in hamster cheek pouch was also investigated. Absorption was fast from both 12.5 and 20% CP ointments, and the drug absorption was sustained for 5 h from 12.5% CP ointment.
96 citations
TL;DR: Antitumor cyclic hexapeptides named RA-VII, V, IV and III were isolated from the MeOH Extracts of Rubia cordifolia and R. akane.
Abstract: Antitumor cyclic hexapeptides named RA-VII, V, IV and III were isolated from the MeOH Extracts of Rubia cordifolia and R. akane.
TL;DR: From the dried stems of Tinospora tuberculata BEUMEE (Menispermaceae), N-transferuloyl tyramine (1), n-cis-feruloyyl tyramerine (2), and a new phenolic glucoside, tinotuberide (6), were isolated as discussed by the authors.
Abstract: From the dried stems of Tinospora tuberculata BEUMEE (Menispermaceae), N-transferuloyl tyramine (1), N-cis-feruloyl tyramine (2), and a new phenolic glucoside, tinotuberide (6), were isolated The structure of 6 was elucidated as 3-(4'-β-D-glucopyranosyloxy-3', 5'-dimethoxyphenylmethoxy)-2-trans-propen-1-ol
TL;DR: In this article, four diarylheptanoids (5R)-trans-1, 7-diphenyl-5-hydroxy-6-hepten-3-one (VIIa), (3S, 5S)-trans-, trans-farnesol (I), trans-cinnamaldehyde, three flavonoids [alpinetin (II), cardamomin (III) and pinocembrin (IV)], and their structures were determined on the basis of chemical and spectral evidence.
Abstract: Four new diarylheptanoids [(5R)-trans-1, 7-diphenyl-5-hydroxy-6-hepten-3-one (VIIa), (3S, 5S)-trans-1, 7-diphenyl-3, 5-dihydroxy-1-heptene (VIIIa), trans-1, 7-diphenyl-5-hydroxy-1-heptene (IX) and trans, trans-1, 7-diphenyl-5-hydroxy-4, 6-heptadien-3-one (Xa)] have been isolated from the seeds of Alpinia katsumadai HAYATA, together with trans, trans-farnesol (I), trans-cinnamaldehyde, three flavonoids [alpinetin (II), cardamomin (III) and pinocembrin (IV)], and two known diarylheptanoids [(3S, 5R)-3, 5-dihydroxy-1, 7-diphenylheptane (V) and trans, trans-1, 7-diphenyl-4, 6-heptadien-3-one (VI)], and their structures were determined on the basis of chemical and spectral evidence. This is the first time that trans-cinnamaldehyde, IV, V and VI have been isolated from these seeds.
TL;DR: A mannan and water-soluble glucans from Dictyophora indusiata, a water-insoluble glucan from Ganoderma japonicum, a galactomannan from Cordyceps cicadae, and acidic heteroglycans from Auricularia auricula-judae and auricularia species were tested for antitumor activity against subcutaneously implanted sarcoma 180 in mice by intraperitoneal administration.
Abstract: A mannan and water-soluble glucans from Dictyophora indusiata, a water-insoluble glucan from Ganoderma japonicum, a galactomannan from Cordyceps cicadae, and acidic heteroglycans from Auricularia auricula-judae and Auricularia species (Yu er), whose structural features have been reported in our previous papers of this series, were tested for antitumor activity against subcutaneously implanted sarcoma 180 in mice by intraperitoneal administration. Considerable antitumor activity was observed with partially O-acetylated (1→3)-α-D-mannan (T-2-HN) at doses of 10 mg·kg-1·d-1×10, water-soluble (1→3)-β-D-glucans having β-1→6 linked D-glucosyl side chains (T-4-N and T-5-N) at doses 5 or 10 mg·kg-1·d-1×10, and a glucuronoxyloglucomannan (U-3-A) at doses of 25 mg·kg-1·d-1×10.
TL;DR: From Red Ginseng, all of the known saponins of White Ginseng were isolated in yields similar to those obtained from Black Ginseng.
Abstract: From Red Ginseng, all of the known saponins of White Ginseng were isolated in yields similar to those obtained from White Ginseng. Two additional minor saponins, notoginsenoside-R1 (19) (the saponin of roots of Panax notoginseng) and quinquenoside-R1 (20) (the saponin of roots of P. quinquefolium), were also isolated and identified. Besides these known saponins, two new minor saponins named ginsenosides-Rs1 (17) and -Rs2 (18) were also isolated. Compounds 17 and 18 were established to be monoacetates at the 6-hydroxyl group of the terminal glucosyl moiety of the sophorosyl unit of ginsenosides-Rb2 (5) and-Rc (7), respectively.
TL;DR: In this paper, the Bu2SnO method was used for selective mono-benzoylation of pento-and hexo-pyranosides (Me β-L-Ara, Ph α-Lα, Me α-D-Xyl, Me β-D-, Xyl, Xyl-Me α-G-Glc, EH-Meα-Dα, Xα-Gα, Gα-Hα, Hα-Eα, Eα-Oα, Oα-Meβ-D
Abstract: Selective mono-benzoylation of some pento- and hexo-pyranosides (Me β-L-Ara, Ph α-L-Ara, Me α-D-Xyl, Me β-D-Xyl, Me α-D-Glc, Me β-D-Glc, Me α-D-Gal, Me β-D-Gal, and Me α-D-Man) by using Bu2SnO was examined in comparison with the results of the (Bu3Sn)2-O method and direct benzoylation. The Bu2SnO method is particularly useful in that it selectively activates an equatorial hydroxyl group which bears an oxygenated function (OH or OMe) in a cis relationship at an adjacent position, even in the presence of a more reactive primary OH group. The various mono- and di-O-benzoyl derivatives prepared in this work were unambiguously identified by analysis of their 13C-nuclear magnetic resonance spectra.
TL;DR: The pharmacokinetic character of ginsenoside Rb1 (Rb1), one of the main 20 (S)-protopanaxadiol group saponins of gINSeng (Panax ginseng C.A. MEYER), was investigated in rats and the results are quite different from the results on ginseneside Rg1 in rats.
Abstract: The pharmacokinetic character of ginsenoside Rb1 (Rb1), one of the main 20 (S)-protopanaxadiol group saponins of ginseng (Panax ginseng C.A. MEYER), was investigated in rats. First, quantitative analysis of Rb1 in biological samples was investigated and the most suitable assay procedure for each biological sample was established. Little Rb1 was absorbed from the digestive tract after oral administration (100mg/kg) to rats. The serum level of Rb1 in rats after intravenous injection (5 mg/kg) declined biexponentially, and the half-life of the β-phase was 14.5 h. The long persistence of Rb1 in serum and tissues in rats after intravenous administration was assumed to correlate with the high activity of plasma protein binding. Rb1 was gradually excreted into urine, but not bile. Unabsorbed Rb1 in the digestive tract was rapidly decomposed and/or metabolized mainly in the large intestine. These results are quite different from our results on ginsenoside Rg1 in rats.
TL;DR: Based on chemical and physicochemical investigations including carbon-13 nuclear magnetic resonance (13C-NMR) examinations and methylation analyses, the structures of three astragalosides were elucidated as discussed by the authors.
Abstract: Based on chemical and physicochemical investigations including carbon-13 nuclear magnetic resonance (13C-NMR) examinations and methylation analyses, the structures of three astragalosides, which were isolated from Astragali Radix, the root of Korean Astragalus membranaceus BUNGE (Leguminosae), were elucidated : astragaloside III is 3-O-[β-D-glucopyranosyl (1→2)-β-D-xylopyranosyl] cycloastragenol (3), astragaloside V is 3-O-[β-D-glucopyranosyl (1→2)-β-D-xylopyranosyl]-25-O-β-D-glucopyranosyl-cycloastragenol (5) and astragaloside VI is 3-O-[β-D-glucopyranosyl (1→2)-β-D-xylopyranosyl]-6-O-β-D-glucopyranosyl-cycloastragenol (6).
TL;DR: The biodegradability of poly (ethylene carbonate) and poly (propylene carbonate), synthesized from carbon dioxide and alkylene epoxides, was investigated and no retardation in body weight gain was observed in polycarbonate-implanted rats.
Abstract: The biodegradability of poly (ethylene carbonate) and poly (propylene carbonate), synthesized from carbon dioxide and alkylene epoxides, was investigated. The biodegradation of poly (ethylene carbonate) pellets in the peritoneal cavity in rats was observable 2 d after implantation and was nearly completed within 2 weeks. The degradation of poly-(propylene carbonate) pellets was not measurable after 2 months. The degradation rate of the pellets made of mixtures of the two types of polycarbonates decreased with increase in poly (propylene carbonate) content. No retardation in body weight gain was observed in polycarbonate-implanted rats. No visible undesirable reaction was observed at the implanted sites.
TL;DR: In this article, tannin-related compounds (I-VI) have been isolated from commercial rhubarb, and their structures have been established on the basis of chemical and spectroscopic data to be 1-O-galloylglycerol (I), gallic acid 3-Oβ-D-(6'-O-glucopyranoside (II), 1, 6-di-O-, β-D-D)-glucose (III), 6-o-galloylelglucoside (IV), 4-(4
Abstract: Six tannin-related compounds (I-VI) have been isolated from commercial rhubarb, and their structures have been established on the basis of chemical and spectroscopic data to be 1-O-galloylglycerol (I), gallic acid 3-O-β-D-(6'-O-galloyl)-glucopyranoside (II), gallic acid 4-O-β-D-(6'-O-galloyl)-glucopyranoside (III), 1, 6-di-O-galloyl-β-D-glucose (IV), 6-O-galloylglucose (V) and 4-(4'-hydroxyphenyl)-2-butanone 4'-O-β-D-(2"-O-galloyl)-glucopyranoside (VI, named isolindleyin).
TL;DR: In suspended particulates collected in Yokohama over various 24-h periods, the following seven nitrophenols were detected as mentioned in this paper ; o-nitrophenol, p-nitro-, 2, 6-dinitrophenolate, 2, 4-dinetrophenoid, 2-methyl-6-nitroid, 2methyl-4-nitronoid, and 3-methyl -4nitrophetoid.
Abstract: In suspended particulates collected in Yokohama over various 24-h periods, the following seven nitrophenols were detected ; o-nitrophenol, p-nitrophenol, 2, 6-dinitrophenol, 2, 4-dinitrophenol, 2-methyl-6-nitrophenol, 2-methyl-4-nitrophenol and 3-methyl-4-nitrophenol These nitrophenols were also observed in smog chamber experiments carried out with benzene and toluene in the presence of nitrogen dioxide in air
TL;DR: Two new derivatives of butyrolactone I were isolated from Aspergillus terreus IFO 4100 and the structures were determined and three enzymes involved in the biosynthesis were identified.
Abstract: Two new derivatives of butyrolactone I were isolated from Aspergillus terreus IFO 4100, and the structures were determined. A metabolic pathway from phenylalanine to butyrolactone I was established by administration of potential intermediates to growing or resting cells of Aspergillus terreus IFO 8835 and by enzymatic studies. Three enzymes involved in the biosynthesis were identified.
TL;DR: In this article, the structure of cycloastragenol and astragenol were elucidated as (20R, 24S)-3β, 6α, 16β, 25-tetrahydroxy-20, 24-epoxy-9, 19-cyclolanostane (1), and (20 R, 24 S)-3 β, 6β, 16 β, 25Tetrahyldoxy-20 (20), 24-Eoxy-lanost-9 (11)-ene (5), respectively.
Abstract: Triterpene-oligoglycoside constituents of Astragali Radix, the root of Korean Astragalus membranaceus BUNGE (Leguminosae), were isolated. By means of enzymatic and chemical degradations, the 9, 19-cyclolanostane-type triterpene named cycloastragenol (1), which was the common genuine aglycone of ten of eleven astragalosides, and the lanost-9 (II)-ene-type counterpart named astragenol (5), which was an artifact aglycone secondarily formed from 1, were isolated. On the basis of chemical and physicochemical evidence, the structures of cycloastragenol and astragenol were elucidated as (20R, 24S)-3β, 6α, 16β, 25-tetrahydroxy-20, 24-epoxy-9, 19-cyclolanostane (1) and (20R, 24S)-3β, 6α, 16β, 25-tetrahydroxy-20, 24-epoxy-lanost-9 (11)-ene (5), respectively.
TL;DR: A series of ω-(1-substituted-5-tetrazolylalkoxy)-2-oxoquinolines was synthesized and tested for inhibitory activity towards collagen-and adenosine diphosphate (ADP)-induced aggregation of rabbit blood platelets in vitro.
Abstract: A series of ω-(1-substituted-5-tetrazolylalkoxy)-2-oxoquinolines was synthesized and tested for inhibitory activity towards collagen-and adenosine diphosphate (ADP)-induced aggregation of rabbit blood platelets in vitro. These compounds were prepared by the reaction of 1-substituted-5-(ω-chloroalkyl)-tetrazoles and hydroxy-2-oxoquinolines in the presence of a base. Among them, 6-[3-(1-cyclohexyl-5-tetrazolyl)propoxy]-1, 2-dihydro-2-oxoquinoline (IVb) was found to have the most potent inhibitory activity. The structure-activity relationships are discussed.
TL;DR: In this article, the locations of the acetyl groups of Saponins 7 and 9 were established to be at the 4-hydroxyl group of the xylosyl unit of 8 and at the 3, 4-oxyl groups in the terminal arabinosyl units of 7, respectively.
Abstract: From pericarps of Sapindus mukurossi (Japanese name : Enmei-hi), saponins of hederagenin (1), 2-7, 9, 11 and 12 were isolated along with sapindosides A (10) and B (8), both of which have already been isolated from this crude drug. Saponins 7 and 9 were identified as α-L-arabinopyranosyl (1→3)-α-L-rhamnopyranosyl (1→2)-α-L-arabinopyranoside and α-L-arabinofuranosyl (1→3)-α-L-rhamnopyranosyl (1→2)-α-L-arabinopyranoside of 1, respectively, both of which were recently isolated from Lecaniodiscus cupanoides by Sandberg et al. New saponins named mukurozi-saponins E1 (11) and G (12) were proved to be the mono-acetate of 8 and the di-acetate of 7, respectively. By means of mass and 13C nuclear magnetic resonance (NMR) spectroscopy, the locations of the acetyl groups of 11 and 12 were established to be at the 4-hydroxyl group of the xylosyl unit of 8 and at the 3, 4-hydroxyl groups of the terminal arabinosyl unit of 7, respectively. The other new saponins, named mukurozi-saponins X (6), Y1 (5) and Y2 (4), were revealed to be β-sophorosyl esters of 10, 8 and 7, respectively, by comparison of the mass and 13C NMR spectra with those of the β-sophorosyl ester of 1 (13), which was synthesized from 1 as a reference compound for the study of the anomalous glycosylation shifts. Studies on the structures of the remaining saponins, 2 and 3, are in progress. The water solubilities of the monodesmosides, 7-9, which cause remarkable enhancement of the absorption of sodium ampicillin from rat intestine and rectum, were greatly increased by the bisdesmosides, 4-6.
TL;DR: An increase in lipid peroxidation and a decrease in activity of SOD in the brain after oral administration of aluminum hydroxide constitute one of the factors for the mechanism of brain injury by aluminum.
Abstract: The effect of aluminum ingestion on the lipid peroxidation in rat brain, lung, liver, spleen and kidney was examined. Aluminum hydroxide, 100 mg/kg body weight, was administered orally once a day for 7 d, and the amount of lipid peroxide (TBA value) and the activity of superoxide dismutase (SOD) were measured 24 h after the last administration. Lipid peroxide was increased in the brain, to 142% of the control. TBA values in the lung, liver, spleen and kidney were similar to those in the control group. Pretreatment of rat brain, lung, liver, spleen, and kidney homogenates with aluminum chloride in an ice-bath increased the TBA value in the brain significantly compared with that of the control. Examination of variation in SOD activity showed that the activity in the brain was decreased, while that in the kidney was increased, compared with those of the control. Activities of SOD in the lung, liver, and spleen were similar to those of the control. These results suggest that an increase in lipid peroxidation and a decrease in activity of SOD in the brain after oral administration of aluminum hydroxide constitute one of the factors for the mechanism of brain injury by aluminum.
TL;DR: The lung surfactants modified with palmitic acid, stearic acid and a mixture of fatty acids showed better surface activities in vitro and gave better lung pressure-volume characteristics in situ than those with oleic Acid and triacylglycerols.
Abstract: The relations between the kinds of fatty acids and triacylglycerols present and the properties of lung surfactants were examined with modified lung surfactants. Palmitic acid-tripalmitoylglycerol, stearic acid-tristearoylglycerol and mixtures of fatty acids-triacylglycerols gave good surface activities with the lung surfactant, but oleic acid-trioleoylglycerol did not give good surface activity in vitro. Lung surfactants modified with palmitic acid-tripalmitoylglycerol, stearic acid-tristearoylglycerols and the mixtures restored the initial lung pressure-volume characteristics to the excised lung after these characteristics had been lost as a result of lavage in situ. Fatty acids gave better surface activities with the lung surfactant than triacylgycerols. The lung surfactants modified with palmitic acid, stearic acid and a mixture of fatty acids showed better surface activities in vitro and gave better lung pressure-volume characteristics in situ than those with oleic acid and triacylglycerols. The protein contained in the bovine lung surfactant was a lipoprotein in which the molar ratio of phopsholipids to protein was about 100 : 1. The molecular weight of the protein was 35000 and was reduced to 10000 by pretreatment with 2-mercaptoethanol after the removal of the phospholipids from the lipoprotein. This protein contained a large proportion of nonpolar amino acids. The lipoprotein showed spontaneous spreading with 1, 2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC), and with mixtures of DPPC and palmitic acid or tripalmitoylglycerol. The lipoprotein also enlarged the areas of the hysteresis loops of DPPC and the mixtures.
TL;DR: In this article, the formation of spironolactone (SP) with three cyclodextrins (α-, β-, γ-CyDs) in aqueous solution and in the solid state were studied by the solubility method, by spectroscopic methods (UV, CD, IR) and by X-ray diffractometry, and their modes of interaction were assessed.
Abstract: Inclusion complex formations of spironolactone (SP) with three cyclodextrins (α-, β-, γ-CyDs) in aqueous solution and in the solid state were studied by the solubility method, by spectroscopic methods (UV, CD, IR) and by X-ray diffractometry, and their modes of interaction were assessed. The solid complexes of SP with β- and γ-CyDs were obtained in molar ratios of 1 : 2 and 2 : 3, respectively, and their dissolution, membrane permeation and oral absorption properties were examined. The rates of dissolution and permeation through a cellophane membrane in water were significantly increased by inclusion complexation (γ-CyD complex>β-CyD complex>SP alone), depending upon the solubility of the test samples. The serum levels of SP following oral administration of CyD complexes were found to be greater than those after administration of SP alone. The results indicated that the γ-CyD complex rather than β-CyD complex may have great utility as a faster dissolving form of SP able to produce higher serum levels.
TL;DR: Benzylic, allylic carbons and the carbon α to hetero atoms are electrochemically oxidized to the corresponding carbonyl group in the presence of N-hydroxyphthalimide under mild conditions as mentioned in this paper.
Abstract: Benzylic, allylic carbons and the carbon α to hetero atoms are electrochemically oxidized to the corresponding carbonyl group in the presence of N-hydroxyphthalimide under mild conditions.