Akiyo Sakushima

Hydroxybenzoic acids from Boreava orientalis

A new guaiacylglycerol ether, threo-guaiacylglycerol-8′-vanillic acid ether, pyrocatechuic acid, pyrocatechuic acid 3-O-β-d-glucoside, gentisic acid, gentisic acid 5-O-β-d-glucoside, vanillic acid and vanillic acid 4-O-β-d-glucoside were identified from fruits of Boreava orientalis. Structural elucidation was carried out on the basis of UV, mass, 1H and 13C NMR spectral data, including 2D shift-correlation and selective INEPT experiments.

Estrogenic and anti-estrogenic activities of two types of diesel exhaust particles

In an earlier study using a recombinant yeast screen we found that a suspension of diesel exhaust particles (DEP) and some extracts of DEP are not estrogenic but possess anti-estrogenic activity. In the present study, estrogenic and anti-estrogenic activities of two types of DEP, type-1 (old type) and type-2 (new type) were compared. Whole DEP of both types were found to possess estrogenic and anti-estrogenic activities. The DEP were serially extracted with organic solvents and then with 1 M ammonia and 1 M HCl. In type-2 DEP, the ratio of dry weight of a hexane extract was higher than those of methanol and ammonia extracts, which were lower than those in type-1 DEP. In the hexane extract, estrogenic activity was found in both types of DEP. In the benzene and dichloromethane extracts, estrogenic and anti-estrogenic activities were found in both types of DEP. In the methanol extract, estrogenic activity was found in type-2 DEP, and extracts of both types decreased the activity of estrogen. Anti-estrogenic activity was found in extracts of ammonia and HCl from both types of DEP. It was found that both type-1 and type-2 DEP possess estrogenic and anti-estrogenic activities.

Application of fast atom bombardment mass spectrometry to chlorogenic acids

Abstract The technique of positive- and negative-ion fast atom bombardment mass spectrometry has been shown to be capable of producing molecular mass and useful fragmentation information for the structural elucidation of chlorogenic acids. The mass spectra of chlorogenic acid and the related compounds 3′- O -methylchlorogenic acid, neochlorogenic acid, 4,5-dicaffeoyl quinic acid and 1,5-dicaffeoyl quinic acid are compared with those obtained by electron impact mass spectrometry.

Flavonoids from Rhamnus pallasii

Abstract A new dihydroflavonol, pallasiin, together with kaempferol, quercetin, isorhamnetin, mearnsetin, aromadendrin, eriodictyol and taxifolin, has been isolated from the bark of Rhamnus pallasii and its structure elucidated as 2,3-dihydromyricetin 4′- O -methyl ether.

Mass spectrometry in the structural determination of flavonol triglycosides from Vinca major

Abstract Chlorogenic acid, robinin and a flavonol triglycoside were isolated from the leaves of Vinca major . The structure of the triglycoside was determined to be kaempferol 3- O -(6″- O -rhamnopyranosyl)-galactopyranoside 7- O -glucopyranoside by fast atom bombardment, electron impact and negative ion desorption chemical ionization mass spectrometry.

Separation and Identification of Taxifolin 3- O -Glucoside Isomers from Chamaecyparis Obtusa (Cupressaceae)

Taxifolin 3- O -glucoside isomers, [(2R, 3R)-, (2R, 3S)-, (2S, 3R)- and (2S, 3S)-] were isolated from leaves of Chamaecyparis obtuse (Cupressaceae). Their structures were elucidated on the basis of UV, MS, CD, 1 H- and 13 C-NMR spectral data, including 2D shift correlation. It was found that the compounds could be distinguished by the use of 1 H- and 13 C-NMR spectral data.

Sinapinyl but-3-enylglucosinolate from Boreava orientalis

A new glucosinolate salt, named boreavan A, has been isolated from fruits of Boreava orientalis. Its structure has been established as sinapinyl but-3-enylglucosinolate on the basis of chemical and spectral evidence, including 2D-shift correlation and DEPT NMR experiments.

An anthraquinone glycoside from Rhamnus pallasii

Abstract A new anthraquinone glycoside, together with α-sorinin, has been isolated from the bark of Rhamnus pallasii and its structure elucidated as physc

Studies of isoindoles. 12.1 A structural revision of the 1 :2 mannich type condensation reaction product formed from o-phthalaldehyde and substituted aniline

The structure of the double Mannich condensation product from o-phthalaldehyde and substituted aniline was proved to he iminoisoindoline, but not diimine, based on X-Ray analysis.

Dihydrobenzofuran lignans from Boreava orientalis

Abstract Two new dihydrobenzofuran lignanamides and three known dihydrobenzofuran lignans have been isolated from fruits of Boreava orientalis. The structures of the two new compounds were established as cis- and trans- (2 R ,3 S )-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-7-methoxybenzofuran-5-propen-1-ic(1,5-dimethyl)glutamate amide on the bases of chemical and spectral evidence, including NOE, 2D shift-correlation and HMBC NMR experiments.