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Biomedical subjects

Shigeru Takaoka

Publications and source records attributed to Shigeru Takaoka.

13 recordsLinked to original sources

Chemical constituents of Malagasy liverworts: cyclomyltaylanoids from Bazzania madagassa.

Five cyclomyltaylanoids (2-6), together with 1R,5R-diacetoxycyclomyltaylan-10-one (1), (+)-globulol, and ent-4beta,10alpha-dihydroxyaromadendrane have been isolated from the diethyl ether fraction of the Malagasy liverwort, Bazzania madagassa. The structure of 1 was confirmed by X-ray analysis, while those of the compounds were established on the basis of one- and two-dimensional NMR spectroscopic evidence, and comparison with data reported in the literature. The chemosystematics of B. madagassa are discussed.

Crystallography, X-Ray↗

Cinnafragrins A-C, dimeric and trimeric drimane sesquiterpenoids from Cinnamosma fragrans, and structure revision of capsicodendrin.

Two new dimeric sesquiterpenoids and a new trimeric drimane sesquiterpenoid named cinnafragrins A-C (1-3), together with cinnamodial (4), D-mannitol, capsicodendrin (5), and a vitamin E analogue, delta-tocotrienol, were isolated from Cinnamosma fragrans, a Malagasy medicinal plant. The structures of the new compounds were determined on the basis of physical, chemical, and spectroscopic evidence. Capsicodendrin, previously isolated from Capsicodendron dinisii and tentatively suggested to be a tetramer of cinnamodial, was revised structurally as a mixture of C-12'-epimers of 12'-hydroxycinnafragrin B by extensive 2D NMR analysis and X-ray crystallography of the lactone derivative, cinnafragrolide (6). The chemosystematics of the family Canellaceae are discussed.

Crystallography, X-Ray↗

Momordica charantia constituents and antidiabetic screening of the isolated major compounds.

Bioguided fractionation of the methanol extract of Momordica charantia dried gourds led to the isolation of three new cucurbitane triterpenoids (1-3), together with eight known compounds (4-11). The aglycone of momordicoside I was isolated from the ether soluble fraction in a high amount. The structures of the metabolites were established on the basis of one and two dimensional NMR spectroscopic evidence, X-ray analysis, and comparison with the reported data in the literature. A number of phytochemicals have been isolated from Momordica charantia but the constituents responsible for the hypoglycaemic/antihyperglycaemic activities have not been determined. Therefore, in order to evaluate the contribution of the cucurbitane triterpenoids of the ether fraction of M. charantia methanol extract to in vivo anti-diabetic effects, the major compounds, 5beta,19-epoxy-3beta,25-dihydroxycucurbita-6,23(E)-diene (4), and 3beta,7beta,25-trihydroxycucurbita-5,23(E)-dien-19-al (5) have been tested and have shown blood hypoglycaemic effects in the diabetes-induced male ddY mice strain at 400 mg/kg. The two aglycones of charantin did not show any hypoglycaemic effects. Our finding is the first demonstration that major pure cucurbutanoid compounds of M. charantia have in vivo hypoglycaemic effects.

Animals↗

ent-Verticillane-type diterpenoids from the Japanese liverwort Jackiella javanica.

Three ent-verticillane diterpenoids and two ent-sesquiterpenoids were isolated from the Japanese liverwort Jackiella javanica Schiffn. together with five known ent-verticillane and three ent-kaurane diterpenoids, and three sesquiterpenoids. Five ent-verticillane epoxides were synthetically prepared from ent-verticillols action to clarify the absolute configuration of natural ent-9,10-epoxyverticillol. Their structures were established by extensive NMR spectroscopic and X-ray crystallographic analyses.

Diterpenes↗

Psychophysical sensory examination in individuals with a history of methylmercury exposure.

Paresthesias are the first symptom that people report following toxic doses of methylmercury. The authors conducted a psychophysical study of tactile sensation to evaluate the somatosensory abilities of subjects living in a methylmercury-polluted area around Minamata City, Japan. The authors examined control subjects and methylmercury-exposed subjects with and without numbness. A history of methylmercury exposure was taken and a neurological examination performed. Aluminum-oxide abrasive papers were used as stimuli in a psychophysical sensory examination of fine-surface-texture discrimination. Difference thresholds from 3 microm were calculated by the two-alternative, forced-choice technique. Difference thresholds in control subjects were also calculated for comparison. The difference threshold was 6.3 microm in exposed subjects with sensory symptoms, 4.9 microm in exposed subjects without sensory symptoms, and 2.7 microm in control subjects. Acuity of fine-surface-texture discrimination was disturbed not only in subjects with clinical complaints of hand numbness, but also in subjects without hand numbness who lived in the district where methylmercury exposure occurred. Sensory testing using a psychophysical test of fine-surface-texture discrimination in this population suggests that the number of individuals affected by methylmercury exposure in the polluted area was greater than previously reported.

Aged↗

Tyromycic acids B-E, new lanostane triterpenoids from the mushroom Tyromyces fissilis.

Four new triterpenoids, tyromycic acids B-E (1-4), were isolated from a methanol-soluble extract of the fruit bodies of the Japanese inedible mushroom Tyromyces fissilis. Tyromycic acids B-D possess a lanostane skeleton, while tyromycic acid E is based on a rare 14(13-->12)abeo-lanostane skeleton. Their structures were determined by spectral data analysis and by single-crystal X-ray crystallography.

Agaricales↗

Terpenoids and aromatic compounds from the New Zealand liverworts Plagiochila, Schistochila, and Heteroscyphus species.

A new clerodane- and two new ent-rosane-type diterpenoids have been isolated from the New Zealand liverworts Heteroscyphus billardierii and Plagiochila deltoidea, respectively. The known bisbibenzyl compounds and acetophenones have also been isolated from Schistochila glaucescens and Plagiochila fasciculata. Their structures were established by extensive NMR techniques. Chemosystematics of the Plagiochila species have been discussed.

Hepatophyta↗

New sesquiterpenoids from the New Zealand liverwort Chiloscyphus subporosus.

A new aromadendrane-type sesquiterpenoid, 4(15)-aromadendren-12,5alpha-olide and an aromadendrane-guaianolide dimer have been isolated from the New Zealand liverwort Chiloscyphus subporosus. Their structures were established by extensive NMR techniques and X-ray crystallographic analysis.

Antineoplastic Agents, Phytogenic↗

Two novel ravenelones from the edible mushroom Pulveroboletus ravenelii.

Two novel butenolides, isoravenelone (1) and ravenelone (2), and a large amount of a known compound, vulpinic acid (3), were isolated from the methanolic extract of the Japanese fungus Pulveroboletus ravenelii (Boletales). These structures were elucidated by two dimensional (2D) NMR, MS, IR and UV spectra, and X-ray crystallographic analysis.

4-Butyrolactone↗

A novel ent-kaurane diterpenoid from the Croton tonkinensis GAGNEP.

A novel ent-kaurane diterpenoid, ent-1alpha-acetoxy-7beta,14alpha-dihydroxy-kaur-16-en-15-on has been isolated from leaves of Croton tonkinensis GAGNEP. Its structure was determined by a combination of spectroscopy, X-ray crystallographic analysis and the chemical reaction acetylation.

Acetylation↗

Polysulfide derivatives from Ferula foetida.

The ethyl acetate-soluble fraction from a methanol extract of Ferula foetida has afforded six new sulfide derivatives, (E)-3-methylsulfinyl-2-propenyl sec-butyl disulfide (foetisulfide A) (1), (Z)-3-methylsulfinyloxy-2-propenyl sec-butyl disulfide (foetisulfide B) (2), (E)-3-methylsulfinyloxy-2-propenyl sec-butyl disulfide (foetisulfide C) (3), bis(3-methylthio-2E-propenyl) disulfide (foetisulfide D) (4), 3,4,5-trimethyl-2-thiophenecarboxylic acid (foetithiophene A) (5), 3,4,5-trimethyl-2-(methylsulfinyloxymethyl)thiophene (foetithiophene B) (6), along with six known compounds. The structures of 1-6 were established on the basis of spectroscopic studies, with the elucidation of 5 confirmed by single-crystal X-ray crystallography.

Chromatography, High Pressure Liquid↗

Sesquiterpenes from Ferula penninervis.

The ethyl acetate soluble extract of the dried roots of Ferula penninervis gave 17 new sesquiterpenes [15 of the guaiane-type, ferupennins A-O (1-15), and two of the eudesmane-type, 1alpha-hydroxy-2-oxo-5alpha,7beta,11betaH-eudesm-3-en-6alpha,12-olide (16) and penninervin (17)] and nine known sesquiterpenes. The structures of the new compounds were elucidated on the basis of spectroscopic evidence and X-ray analysis. The absolute configuration of ferupennin A (1) was determined by a modified Mosher method.

Acetates↗