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Anti-herpes simplex virus type-1 flavonoids and a new flavanone from the root of Limonium sinense.

From the root of Limonium sinense (Girard) Ktze a new (2R,3S)-3,5,7,4'-tetrahydroxy-3',5'-dimethoxyflavanone was isolated and named isodihydrosyringetin (3), together with nine other known compounds, (-)-epigallocatechin 3-O-gallate (1), samarangenin B (2), myricetin (4), myricetin 3-O-alpha-rhamnopyranoside (5), quercetin 3-O-alpha-rhamnopyranoside (6), (-)-epigallocatechin (7), gallic acid (8), N-trans-caffeoyltyramine (9), and N-trans-feruloyltyramine (10). All of them were examined for their inhibitory effects on herpes simplex virus type-1 (HSV-1) replication in Vero cells. Both compounds 1 and 2 exhibited potent inhibitory activities in HSV-1 replication. Comparison of the IC50 values indicated that compounds 1 and 2 had higher inhibitory activities than the positive control acyclovir (38.6 +/- 2.6 vs. 55.4 +/- 5.3 microM, P < 0.001; 11.4 +/- 0.9 vs. 55.4 +/- 5.3 microM, P < 0.0005). Cytotoxicity was unlikely involved because no cell deaths were observable in the Vero cells following 5 day treatments with compound 1 or 2.

Animals↗

Role of sulfate concentration in dechlorination of 3,4,5-trichlorocatechol by stable enrichment cultures grown with coumarin and flavanone glycones and aglycones.

Metabolically stable anaerobic enrichment cultures have been obtained from sediment samples contaminated with chlorophenolic compounds. Enrichment was carried out with esculin, esculetin, naringin, naringenin, fraxin, quercetin, and acetate in media with two sulfate concentrations. These cultures were used to examine the O-demethylation of 4,5,6-trichloroguaiacol and the dechlorination of 3,4,5-trichlorocatechol. Whereas O-demethylation was observed in all cultures, the occurrence of dechlorination was significantly more restricted. The presence of the carbohydrate moiety in the cultures enriched with the glycones repressed development of populations which were able to carry out dechlorination. Although sulfate at a concentration of 2 g/liter in the primary enrichments blocked the development of populations able to bring about dechlorination, addition of sulfate at this concentration did not inhibit dechlorination in cultures possessing this capability. Different dichlorocatechol isomers were produced under the various conditions, so that in view of the established resistance of some of these to further dechlorination, the ultimate fate of 3,4,5-trichlorocatechol in the natural environment remains partly unresolved. No enrichment culture containing a low sulfate concentration was able to dechlorinate either 2,4,5-trichlorophenol or 2,4,6-trichlorobenzoate.

Anaerobiosis↗

O-demethylation and sulfation of 7-methoxylated flavanones by Cunninghamella elegans.

Metabolism of 7-O-methylnaringenin (sakuranetin) by Cunninghamella elegans NRRL 1392 yielded naringenin and naringenin-4'-sulfate. C. elegans also converted 5, 3', 4'-trihydroxy-7-methoxyflavanone into eriodictyol-4'-sulfate. Furthermore, incubation of 5, 4'-dihydroxy-7, 3'-dimethoxyflavanone with the same fungus gave homoeriodictyol (5, 7, 4'-trihydroxy-3'-methoxyflavanone) and homoeriodicytol-7-sulfate. The structures of the new metabolites were established by spectral analysis including 2D-NMR, HR-ESI-FT-MS beside hydrolysis by acid.

Cunninghamella↗

[Pharmacological and radioprotective properties of some gamma-pyrone derivatives (flavanones and flavanols)].

In experiments set up on mice, rats and guinea pigs 8 gamma-pyron derivatives were studied. They proved to be little toxic, do not change significantly the arterial pressure and respiration, exercise a depressing action on the central nervous system, produce a marked antiphlogistic (normal and irradiated animals), radio-protective and antihistaminic effects and influence norephinephrine, homovanillic acid and dopamine metabolism in the brain.

Animals↗