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Biomedical subjects

Yoshihisa Takaishi

Publications and source records attributed to Yoshihisa Takaishi.

At least 19 recordsLinked to original sources

Xanthones from stems of Hypericum chinense.

Six new xanthones, 4,6-dihydroxy-2,3-dimethoxyxanthone (1), 2,6-dihydroxy-3,4-dimethoxyxanthone (2), 6-hydroxy-2,3,4-trimethoxyxanthone (3), 3,6-dihydroxy-1,2-dimethoxyxanthone (4), 4,7-dihydroxy-2,3-dimethoxyxanthone (5), and 3,7-dihydroxy-2,4-dimethoxyxanthone (6) were isolated from the stems of Hypericum chinense, together with four known xanthones. Their structures were established based on spectroscopic studies.

Chromatography, High Pressure Liquid↗

Terpenoids from Juniperus polycarpus var. seravschanica.

Two eudesmanes, two abietanes, two podocarpanes and other nine known compounds were isolated from the dried fruits of Juniperus polycarpus var. seravschanica. Their structures were established on the basis of analysis of spectroscopic evidence. Some of the isolated terpenoids showed antimalarial activity.

Abietanes↗

Xanthones from Hypericum chinense.

Six xanthones, 1,3,7-trihydroxy-2-(2-hydroxy-3-methyl-3-butenyl)-xanthone (1), 1,7-dihydroxy-2,3-[2''-(1-hydroxy-1-methylethyl)-dihydrofurano]-xanthone (2), 1,3,7-trihydroxy-5-methoxyxanthone (3), 1,7-dihydroxy-5,6-dimethoxyxanthone (4), 4,5-dihydroxy-2,3-dimethoxyxanthone (5), 1,3-dihydroxy-2,4-dimethoxyxanthone (6) and 21 known xanthones were isolated from the leaves and stems of Hypericum chinense. Their structures were established based on spectroscopic studies.

Hypericum↗

Immunosuppressive diacetylenes, ceramides and cerebrosides from Hydrocotyle leucocephala.

Three C-17 diacetylenic compounds (1-3), one monoterpenoid (4), seven ceramides (leucoceramides A-G, 5a-g), six cerebrosides (leucocerebrosides A-F, 6a-f) and nine known compounds were isolated from the methanolic extract of Hydrocotyle leucocephala. Their structures were established by spectroscopic methods. The isolated compounds 1-3, 5a-g, 6a-f and 7 were shown to be active in the lipopolysaccharide (LPS) induced cytokine production assay for IL-10, IL-12, and TNF-alpha.

Acetylene↗

Tripfordines A-C, sesquiterpene pyridine alkaloids from Tripterygium wilfordii, and structure anti-HIV activity relationships of Tripterygium alkaloids.

Three new sesquiterpene pyridine alkaloids, tripfordines A-C (1-3), were isolated from an ethanolic extract of the roots of Tripterygium wilfordii, along with eight known pyridine alkaloids, and tested for in vitro cytotoxic and anti-HIV activity. The structures of the new compounds were established on the basis of spectroscopic data interpretation. Anti-HIV structure-activity relationships (SAR) for this compound type are proposed on the basis of the screening results from the newly isolated compounds and prior data of known sesquiterpene pyridine alkaloids. The position of a carboxyalkyl chain on the pyridine moiety was not critical since both 2'- and 4'-substituted compounds exhibited high anti-HIV activity (EC(50) 0.1 microg/mL). In contrast, a hydroxy group at C-8' (carboxypropyl side chain) or C-9' (carboxybutyl side chain) was found to affect anti-HIV activity.

Alkaloids↗

Chemical constituents from the peels of Citrus sudachi.

A methanol extract of the peels of Citrus sudachi gave five new compounds (1-5) and 27 known compounds. The structures were elucidated on the basis of spectroscopic evidence. Several of these compounds were assayed for antimicrobial activity against methicillin-resistant Staphylococcus aureus and Helicobacter pylori, and sudachitin (6) and 3'-demethoxysudachitin (7) were the most active.

Anti-Bacterial Agents↗

Biyouyanagin A, an anti-HIV agent from Hypericum chinense L. var. salicifolium.

[structure: see text] A structurally unique hydrophobic compound, biyouyanagin A, was isolated from the MeOH extract of the leaves of Hypericum chinense L. var. salicifolium. The structure of biyouyanagin A was elucidated on the basis of spectroscopic evidence. Biyouyanagin A showed a significant activity against HIV and inhibited cytokine production.

Anti-HIV Agents↗

Effects of triterpene saponins from Astragalus species on in vitro cytokine release.

Roots of Astragalus species are used to treat leukemia and for wound healing in Turkish folk medicine. In order to evaluate this information, the effect of 13 cycloartane- and 1 oleanan-type triterpene saponins isolated from Turkish species (Astragalus brachypterus, Astragalus cephalotes, Astragalus microcephalus, and Astragalus trojanus), as well as methanol extracts from the roots of three Astragalus species (Astragalus cephalotes, Astragalus oleifolius and Astragalus trojanus) were studied. Cytokine concentrations of interleukins IL-1beta, IL-8 and TNF-alpha after bacterial lipopolysaccharide (LPS) and IL-2, IL-4 and INF-gamma after phorbolacetate (PHA) stimulation were determined using commercial enzyme-linked immunosorbent assay (ELISA) kits. All triterpene saponins tested in the present study showed a prominent IL-2 inducing activity between 35.9% and 139.6%. Among the extracts the highest score was obtained for Astragalus oleifolius (141.2%). Glycosides of 20,24-epoxy and 20,25-epoxy cycloartanes showed higher IL-2 inducing activity than those of acyclic-cycloartane derivatives as well as aglycone of 20,24-epoxy cycloartanes, cycloastrogenol. Especially the activity of Astragaloside VII, a tridesmosidic glycoside of cycloastrogenol, was the most remarkable. The oleanan-type triterpene saponin also showed a prominent IL-2 inducing activity. IL-2 is a cytokine produced by activated T cells, which has shown powerful immunostimulatory and antineoplastic properties. Accordingly, the IL-2 inducing activity of the triterpene saponins might be the mechanism involved in order to explain the immunomodulatory and anticancer effects of Astragalus species.

Adjuvants, Immunologic↗

Champanones, yellow pigments from the seeds of champa (Campomanesia lineatifolia).

Chemical investigation of the methanol extract of the seeds of Campomanesia lineatifolia Ruiz and Pav. (Myrtaceae) led to the isolation of two new beta-triketone type compounds, named champanones A (1) and B (2), together with the known 2,3-dihydro-5-hydroxy-6,8,8-trimethyl-2-phenyl-4H-1-benzopyran-4,7(8H)-dione (champanone C) (3). The structures of 1 and 2 were determined to be 2,2,4,4-tetramethyl-6-(1-oxo-3-phenylprop-2-enyl) cyclohexane-1,3,5-trione (occurs as an enol form) and 2,2,4-trimethyl-6-(1-oxo-3-phenylprop-2-enyl)cyclohexane-1,3,5-trione (occurs as an enol form), respectively, by means of spectroscopic analysis. The three compounds showed mild antimicrobial activity.

Anti-Infective Agents↗

Cyclobutane dimers from the Colombian medicinal plant Achyrocline bogotensis.

Five cyclobutane dimers, achyrodimers A-E (1-5), along with 11 known compounds were isolated from the methanol extract of the Colombian medicinal plant Achyrocline bogotensis. Their structures were elucidated by spectroscopy. Several of these compounds were screened for cytokine-inducing activity in human peripheral blood mononuclear cells.

Achyrocline↗

Anti-Helicobacter pylori compounds from Santalum album.

Six new sesquiterpenes, (Z)-2beta-hydroxy-14-hydro-beta-santalol (1), (Z)-2alpha-hydroxy-albumol (2), 2R-(Z)-campherene-2,13-diol (3), (Z)-campherene-2beta,13-diol (4), (Z)-7-hydroxynuciferol (5), and (Z)-1beta-hydroxy-2-hydrolanceol (6), together with five known compounds, (Z)-alpha-santalol (7), (Z)-beta-santalol (8), (Z)-lanceol (9), alpha-santaldiol (10), and beta-santaldiol (11), were isolated from Santalum album, by using bioassay-guided fractionation for Helicobacter pylori. The structures were determined by extensive NMR studies. The absolute configuration of compound 3 was determined by a modified Mosher method. The crude extracts as well as the isolated compounds showed antibacterial activity against H. pylori. Especially, compounds 7 and 8 have strong anti-H. pylori activities against a clarithromycin-resistant strain (TS281) as well as other strains.

Anti-Bacterial Agents↗

Terpene alkaloids from Tripterygium wilfordii.

Two new sesquiterpene alkaloids, 1beta-hydroxy-2beta,5alpha,11-triacetoxy-7beta-nicotinoyl-8beta-benzoyl-dihydroagarofuran, and 1beta,5alpha,11-triacetoxy-7beta-nicotinoyl-8beta-benzoyl-dihydroagarofuran were isolated from the xylem of Tripterygium wilfordii, together with six known compounds. Their structures were elucidated on the basis of spectroscopic studies.

Molecular Structure↗

Alkyl gallates, intensifiers of beta-lactam susceptibility in methicillin-resistant Staphylococcus aureus.

We found that ethyl gallate purified from a dried pod of tara (Caesalpinia spinosa) intensified beta-lactam susceptibility in methicillin-resistant and methicillin-sensitive strains of Staphylococcus aureus (MRSA and MSSA strains, respectively). This compound and several known alkyl gallates were tested with MRSA and MSSA strains to gain new insights into their structural functions in relation to antimicrobial and beta-lactam susceptibility-intensifying activities. The maximum activity of alkyl gallates against MRSA and MSSA strains occurred at 1-nonyl and 1-decyl gallate, with an MIC at which 90% of the isolates tested were inhibited of 15.6 microg/ml. At concentrations lower than the MIC, alkyl gallates synergistically elevated the susceptibility of MRSA and MSSA strains to beta-lactam antibiotics. Such a synergistic activity of the alkyl gallates appears to be specific for beta-lactam antibiotics, because no significant changes were observed in the MICs of other classes of antibiotics examined in this study. The length of the alkyl chain was also associated with the modifying activity of the alkyl gallates, and the optimum length was C5 to C6. The present work clearly demonstrates that the length of the alkyl chain has a key role in the elevation of susceptibility to beta-lactam antibiotics.

Anti-Bacterial Agents↗

Cupaniol, a New branched polyprenol, from Cupania latifolia.

A new branched polyprenol, designated cupaniol, has been isolated from the methanol extract of the leaves of Cupania latifolia (Sapindaceae). The structure was determined to be (2E,6E,12E,16E)-3,7,13,17,21-pentamethyl-10-(1-methylethenyl)-2,6,12,16,20-docosapentaen-1-ol on the basis of spectral analysis and conversion to a known compound.

Chromatography, High Pressure Liquid↗

Immunosuppressive sesquiterpenes from Tripterygium wilfordii.

Five new sesquiterpenes, 1beta-furanoyl-2beta,3alpha,7alpha,8beta,11-pentaacetoxy-4alpha,5alpha-dihydroxy-dihydroagarofuran (1), 1beta,2beta,3alpha,5alpha,7beta,8beta,11-heptaacetoxy-dihydroagarofuran (2), 1beta-furanoyl-2beta,3alpha,7alpha,8beta,11-pentaacetoxy-5alpha-hydroxy-dihydroagarofuran (3), 1beta,7beta,8alpha-triacetoxy-2beta-furanoyl-4alpha-hydroxy-11-isobutyryloxy-dihydroagarofuran (4), and 1beta-nicotinoyl-2beta,5alpha,7beta-triacetoxy-4alpha-hydroxy-11-isobutyryloxy-8alpha-furanoyl-dihydroagarofuran (5), were isolated from the xylem of Tripterygium wilfordii, together with a known compound (6). Their structures were elucidated on the basis of spectroscopic studies. Compounds 2-5 showed significant immunosuppressive activities.

Drugs, Chinese Herbal↗

Folk medicine in Uzbekistan. I. Toshkent, Djizzax, and Samarqand provinces.

Uzbekistan is one of the Turcic republics in Central Asia where a desert continental climate mainly prevails in territories. Nevertheless, this expedition was carried out in the northeast and east higher lands, where flora is richer. The interviews were performed in seven villages of Toshkent and in neighboring provinces of Samarqand, Djizzax and at Urgut Bazaar of Samarqand. Altogether 177 folk remedies were recorded in the surveyed area. Among these folk remedies, 162 remedies were obtained from 79 different kinds of plant species that belong to 31 different families, whereas, 15 animal originated remedies that belong to 8 different animals are listed, which includes their vernacular and scientific names, indications and recipes for preparations.

Animals↗

Kaurane and abietane diterpenoids from Tripterygium doianum (Celastraceae).

Extraction of Tripterygium doianum (Celastraceae) afforded five new diterpenoids and 11 known diterpenoids belonging to the ent-kaurane and abietane families. Their structures were established based on spectroscopic studies. The isolated compounds showed moderate cytotoxicity against human tumor cell assays.

Abietanes↗