Lavandulifolioside: A New Phenylpropanoid Glycoside from Stachys lavandulifolia

A new phenlypropanoid glycoside has been isolated from the methanolic extract of the aerial parts of Stachys lavandulifolia (Lamiaceae), lavandulifolioside (1) . On the basis of chemical and spectral data the structure of the new compound 1 has been elucidated as β-(3,4-dihydroxyphenyl)ethyl O-α-L -arabinopyranosyl-(1→2)-α-L -rhamnopyranosyl-(1→3)-4-O-caffeoyl-β-D -glucopyranoside.     

The Biological Effects of Forsythia Leaves Containing the Cyclic AMP Phosphodiesterase 4 Inhibitor Phillyrin

Forsythia fruit (Forsythia suspensa Vahl (Oleaceae)) is a common component of Kampo medicines for treating the common cold, influenza, and allergies. The main polyphenolic compounds in the leaves of F. suspensa are pinoresinol β-d-glucoside, phillyrin and forsythiaside, and their levels are higher in the leaves of the plant than in the fruit. It is known that polyphenolic compounds stimulate lipid catabolism in the liver and suppress dyslipidemia, thereby attenuating diet-induced obesity and polyphenolic anti-oxidants might attenuate obesity in animals consuming high-fat diets. Recently, phillyrin was reported as a novel cyclic AMP phosphodiesterase 4 (PDE4) inhibitor derived from forsythia fruit. It was expected that the leaves of F. suspensa might display anti-obesity effects and serve as a health food material. In this review, we summarized our studies on the biological effects of forsythia leaves containing phillyrin and other polyphenolic compounds, particularly against obesity, atopic dermatitis, and influenza A virus infection, and its potential as a phytoestrogen.     

Synthesis of possible metabolites of chlorpromazine. I. 7-hydroxy derivatives of chlorpromazine,nor1-chlorpromazine and nor2-chlorpromazine

The title compounds and various derivatives have been prepared as analytical standards for the identification of chlorpromazine metabolites in biological materials. Additional evidence is presented for the existence of a halogen-induced Smiles rearrangement in the phenothiazine series.     

Phenolic compounds from stem bark of Acanthopanax senticosus and their pharmacological effect in chronic swimming stressed rats

Ten phenolic compounds, isofraxidin (1), (+)-syringaresinol-di-O-beta-D-glucoside (2), syringin (3), chlorogenic acid (4), isofraxidin-7-O-beta-D-glucoside (5), 2,6-dimethoxy-p-benzoquinone (6), (+)-pinoresinol-O-beta-D-glucoside (7), (7), (+)-syringaresinol-O-beta-D-glucoside (8), (+)-pinoresinol-di-O-beta-D-glucoside (9) and (+)-medioresinol-di-O-beta-D-glucoside (10), were isolated from the stem bark of Acanthopanax senticosus Harms and identified, respectively. The aqueous extract of the stem bark exhibited a prolonging effect on the exercise time to exhaustion in chronic swimming stressed rats. The effect on the exercise time in the chronic swimming stressed rats was respectively tested for compounds 2 and 4, which are major constituents of the stem bark. As a result, it was indicated that compound 2 is the compound responsible for part of the pharmacological effect which the aqueous extract of the stem bark showed.     

Synthesis of possible metabolites of chlorpromazine. II. 3-, 8- and 9-hydroxychlorpromazine

The title compounds have been prepared as analytical standards for the identification of chlorpromazine metabolites in biological materials. Unequivocal structural proof of key compounds was accomplished by using at least two unrelated syntheses for each one. Resistance of some phenothiazines to preparation via classic Smiles rearrangement is discussed. More examples are offered of halogen-induced Smiles rearrangement. A rare example of phenothiazine polymorphism is presented.     

Determination of lead at the ng ml-1 level by reduction to plumbane and measurement by inductively-coupled plasma emission spectrometry

A detection limit of 1 ng ml^-1 for lead is obtained by the reported method. Samples are prepared in 0.5 M hydrochloric acid—0.8 M hydrogen peroxide. Plumbane is produced (with 64% efficiency) by the addition of 5% sodium tetrahydroborate in 0.5% NaOH, and is transported by the argon feed directly to an inductively-coupled argon plasma for emission spectrometry. Decreased hydrogen generation and greater stability of the plasma also contribute to the improved detection limit. The method is shown to be generally applicable to As, Sb, Bi, Sn, Te and Se, with detection limits at the ng ml^-1 level.     

A Review of Red Yeast Rice,a Traditional Fermented Food in Japan and East Asia: Its Characteristic Ingredients and Application in the Maintenance and Improvement of Health in Lipid Metabolism and the Circulatory System

Red yeast rice has been used to produce alcoholic beverages and various fermented foods in China and Korea since ancient times; it has also been used to produce tofuyo (Okinawan-style fermented tofu) in Japan since the 18th century. Recently, monacolin K (lovastatin) which has cholesterol-lowering effects, was found in some strains of Monascus fungi. Since statins have been used world-wide as a cholesterol-lowering agent, processed foods containing natural statins are drawing attention as materials for primary prevention of life-style related diseases. In recent years, large-scale commercial production of red yeast rice using traditional solid-state fermentation has become possible, and various useful materials, including a variety of monascus pigments (polyketides) that spread as natural pigments, in addition to statins, are produced in the fermentation process. Red yeast rice has a lot of potential as a medicinal food. In this paper, we describe the history of red yeast rice as food, especially in Japan and East Asia, its production methods, use, and the ingredients with pharmacological activity. We then review evidence of the beneficial effects of red yeast rice in improving lipid metabolism and the circulatory system and its safety as a functional food.     

New Binuclear Copper Complexes [(9S3)Cu(CN)Cu(9S3)]Xn (X=BF4, n=1; X=TCNQ,n=2) (9S3=1, 4, 7‐trithiacyclononane): Syntheses,Crystal Structures and Magnetic Properties

The binuclear Cu complex salts of 1, 4, 7‐trithiacyclononane (9S3) with an inorganic anion (BF₄)^‐ and with an organic radical anion TCNQ^‐ (7, 7′, 8, 8′‐tetracyanoquinodimethanide) were synthesized and their molecular and crystal structures were examined in connection with the magnetic properties. The new complex cation [Cu(9S3)CN(9S3)Cu]⁺ varies its charges and magnetic properties depending on the counter anions; [Cu(9S3)CN(9S3)Cu](BF₄) ( 1 ) was obtained as diamagnetic colorless crystals, while [Cu(9S3)CN(9S3)Cu](TCNQ)₂ ( 2 ) was obtained as dark blue crystals with antiferromagnetic properties. Complex 1 crystallized in the monoclinic space group C2/c with a = 26.863(2), b = 7.0878(5), c = 13.4864(8) Å, β = 116.318(2)°. Complex 2 crystallized in the triclinic space group P1¯ with a = 12.521(1), b = 20.2698(8), c = 8.0205(4) Å, α = 100.688(4), β = 93.846(5), γ = 94.953(4)°. Both complexes are comprised of cyano‐bridged two Cu(9S3) ions with tetrahedral coordination. The X‐ray structural study revealed that 1 has two crystallographically equivalent copper(I) atoms, while 2 has two crystallographically independent Cu^I/II sites. The two Cu^I/II sites could not be distinguished from the X‐ray structural study. For 2 the IR spectra show that both crystallographically independent TCNQ species were monoanions and are strongly dimerized due to π‐stacking, which well explains their diamagnetic contribution to the magnetic susceptibility and the highly insulating property of this salt. The temperature‐dependent magnetic susceptibility of 2 showed a deviation from the Curie‐Weiss behaviour around 60 K, which indicates a strong antiferromagnetic intermolecular interaction between the copper complexes and that such intermolecular interaction should partly occur via the TCNQ radical anion dimer.