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A nitrogen-containing 3-alkyl-1,4-benzoquinone and a gomphilactone derivative from Embelia ribes.

An unusual nitrogen-containing 3-alkyl-1,4-benzoquinone derivative, N-(3-carboxylpropyl)-5-amino-2-hydroxy-3-tridecyl-1,4-benzoquinone (1), and a gomphilactone derivative, 5,6-dihydroxy-7-tridecyl-3-[4-tridecyl-3-hydroxy-5-oxo-2(5H)-furylidene]-2-oxo-3(2H)-benzofuran (2), together with 14 known compounds, as well as the common plant metabolites sitosterol and daucosterol, were isolated from the ethanolic extract of the roots of Embelia ribes. Their structures were elucidated by means of spectroscopic methods. Cytotoxicities of the purified compounds were tested.

Benzoquinones↗

Proanthocyanidins, from Ribes nigrum leaves, reduce endothelial adhesion molecules ICAM-1 and VCAM-1.

BACKGROUND: The effects of proanthocyanidins (PACs), isolated from blackcurrant (Ribes nigrum L.) leaves, on neutrophil accumulation during inflammatory processes were investigated in vivo and in vitro. METHODS: In vivo studies were performed using carrageenin-induced pleurisy in rats pre-treated with PACs. Exudate volume and PMNs accumulation were measured. Leukocyte cell adhesion molecules (LFA-1, Mac-1 and VLA-4) mobilization in circulating granulocytes were analysed by flow cytometry and endothelial cell adhesion molecules (ICAM-1 and VCAM-1) were detected by immunohistochemistry on lung sections. In vitro studies were conducted on endothelial LT2 cells, stimulated with TNF-alpha, to evaluate ICAM-1, IL-8 and VEGF mRNA expression upon PACs treatment. Data sets were examined by one-way analysis of variance (ANOVA) followed by a Scheffe post-hoc test. RESULTS: Pretreatment of the animals with PACs (10, 30 and 60 mg/kg) inhibited dose-dependently carrageenin-induced pleurisy in rats by reducing pleural exudate formation and PMNs infliltration. Leukocyte cell adhesion molecules mobilization was not down-regulated on granulocytes by PACs. Immunohistochemistry on lung sections showed a decreased production of endothelial cell adhesion molecules. In vitro experiments demonstrated that PACs were able to significantly inhibit ICAM-1 but not IL-8 and VEGF165 mRNA expression. Moreover, VEGF121 mRNA expression was dose-dependently enhanced. CONCLUSION: This study provides evidence to support the anti-inflammatory activity of proanthocyanidins is related to an inhibition of leukocyte infiltration which can be explained at least in part by a down-regulation of endothelial adhesion molecules, ICAM-1 and VCAM-1 and that these compounds are capable of modulating TNF-alpha-induced VEGF transcription.

Journal Article↗

Three new flavonol malonylrhamnosides from Ribes alpinum.

Three new flavonol malonylrhamnosides, 3-O-(4"-O-malonyl)-alpha-L-rhamnopyranosides of mearnsetin, myricetin and quercetin respectively, together with the corresponding mearnsitrin, myricitrin, quercitrin and the 4-O-methyl phloracetophenone 2-O-beta-D-glucopyranoside, were isolated from the leaves of Ribes alpinum and fully characterized by spectrocopic methods including 2D NMR.

Glycosides↗

[Lymphedema in patients treated for breast cancer. A cross-sectional study in the county of Ribe. The need of manual lymph drainage; risk factors].

Over a period of three months circumferences of the upper and lower arm were measured in 334 patients previously treated for breast cancer. Lymphoedema was found in 25 (7.5%) of these patients. The total number of patients with breast cancer who had lymphoedema in one year in Ribe Amt was calculated to 40. As more than one half of the patients only had modest or no subjective symptoms, it is expected that about 20 patients pr. year need manual lymph drainage, and about 20 patients need prophylactic physiotherapy. It was found that the risk for increased circumference of the upper arm was correlated to axillary radiotherapy and the total number of lymph nodes removed from the axilla. The risk of increased circumference of the lower arm was correlated to chemotherapy.

Adult↗

Leaf lipids of Ribes nigrum: a plant containing 16:3, alpha-18:3, gamma-18:3 and 18:4 fatty acids.

The glycerolipid composition of Ribes nigrum (blackcurrant) leaves was determined. The total fatty acid composition was unusual in that alpha-linolenic acid (alpha-18:3) occurred together with cis-7,10,13-hexadecatrienoic acid (16:3) and lower amounts of stearidonic acid (18:4) and gamma-linolenic acid (gamma-18:3). Monogalactosyldiacylglycerol contained the highest proportion of 16:3 with less in digalactosyldiacylglycerol. gamma-18:3 and 18:4 were present in all lipids and 18:4 was always greater than gamma-18:3. The highest percentages of gamma-18:3 and 18:4 were in phosphatidylcholine, but phosphatidylglycerol was particularly low in these acids. In summary, the lipid composition was largely typical of 16:3 plants but there was a minor contribution typical of 18:4 plants. The possibility of three pathways for glycolipid biosynthesis is discussed.

Chromatography, Gas↗

Activity of anthocyanins from fruit extract of Ribes nigrum L. against influenza A and B viruses.

Earlier, we have detected antiviral activity in an extract from Ribes nigrum L. fruits ("Kurokarin", name of the one species of black currant in Japanese) against influenza A and B viruses, and herpes simplex virus 1 (Knox et al., Food Processing 33, 21-23, 1998). In the present study, the antiviral activity of constituents of a Kurokarin extract and the mechanism of its antiviral action were examined. Kurokarin extracts were separated to fractions A to D by column chromatography. The major constituents of the fraction D were estimated as anthocyanins. The fraction D was further fractionated by thin-layer chromatography (TLC) to fractions A' to G'. The fraction E' consisted of 3-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranosyl-cyanidin and 3-O-beta-D-glucopyranosyl-cyanidin, and the fraction F' consisted of 3-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranosyl-delphinidin and 3-O-beta-D-glucopyranosyl-delphinidin, identified by high performance liquid chromatography (HPLC) with standards and by high resolution mass spectrometry. The fractions D' to G' showed potent antiviral activity against influenza viruses A and B. The additive antiviral effect of a combination of the fractions E' and F' was assessed. Anthocyanins in the fraction F' did not directly inactivate influenza viruses A and B, but they inhibited virus adsorption to cells and also virus release from infected cells.

Animals↗

Genetic and environmental correlation and path coefficient analysis of fruit yield per bush and other traits in black currants (Ribes nigrum L.).

Twenty-five F1 hybrid families of black currants (Ribes nigrum L.) originating from diallel crosses of five cultivars were assessed. Phenotypic correlation coefficient between full-sib family means (rFS), genetic correlation coefficient between full-sib family expected values (rG) and the environmental correlation were estimated on the basis of two years of observations for 12 quantitative characteristics studied. Evident repeatability of correlations in both years was proved. A considerable consistency between the values of genetic and phenotypic correlation coefficients was also observed. Coefficients of phenotypic and environmental correlation were significant for many pairs of traits. Most of the significant environmental correlation coefficients were found for the same pairs of characteristics for which phenotypic correlation coefficients were significant. This shows that genetic and environmental factors affected similar traits. Fruit yield expressed the largest number of significant correlations with other traits. Path coefficient analysis indicated that plant and berry size were the main factors influencing directly fruit yield in both years. It was proved that the number and length of one-year-old shoots via bush size had very large indirect effects on fruit yield per plant.

Journal Article↗

New compounds from the seeds of Embelia ribes Burm.

Phytochemical investigation of the seeds of Embelia ribes Burm. resulted in the isolation of three new compounds identified as 3-(4"-hydroxyoctadecanyloxy)-p-quinonyl-5-methylene-8-(10-pentanyloxy)-p-quinone (embelinol) (1), n-pentacosanyl-n-nonadeca-7'-en-9'-alpha-ol-1'-oate (embeliaribyl ester) (2) and 1,2,4,5-tetrahydroxy 3-undecanyl benzene (embeliol) (3) along with the known compound 2,5-dihydroxy-3-undecyl-2,5-cyclohexadiene-1,4-dione (embelin) (4). Their structures have been established on the basis of spectral data analyses and chemical reactions.

Chromatography, Thin Layer↗

Screening of Veronica anthelmintica seed and Embella ribes fruit mixed in equal parts against gastrointestinal nematodes.

The antinematodal activity of a mixed prescription of Veronia anthelmintica seed (Kali zeeri) and Embelia ribes fruit (Babrang) was evaluated in goats. The EPG (Egg per gram) counts were made in the faeces before and on the 3rd, 10th and 15th days of the treatment with the powder in 0.5, 1 and 2 g/kg body weight doses and with the water and methanol extracts equivalent to 2 g/kg of the original powder. The evaluation of data on 15th day of the administration showed that 2 g/kg of powder, its equivalent amount of methanol extract and 0.01 g/kg of morantel tartrate are equally effective and safe in treating natural gastrointestinal nematode infection of the local goats.

Journal Article↗

[Leptospirosis in the Ribe County 1980-1991].

Though only 4.2% of the Danish population live in Ribe County, 12 cases of leptospirosis (22% of the Danish total) were found in the county between 1980-1991. Nine cases were associated with fresh water angling or fish farming. The patients were typically young or middle-aged formerly healthy men, who suddenly became ill with acute febrile disease. Eleven patients survived, one died. Cases were most often seen in late summer and autumn. Four patients required dialysis, and these patients also had relatively high serum levels of bilirubin. Case history and simple laboratory findings are helpful in leading to the diagnosis. Three patients were admitted with the correct diagnosis, and by the third day in hospital all 12 were being treated with relevant antibiotics, eight on suspicion of leptospirosis. Three patients had positive blood cultures on day 4, 6 and 9, and nine patients had late positive serology, two of whom also belonged to the group with positive blood cultures. In two patients the diagnosis was based on clinical findings alone. For these reasons, penicillin should be commenced on clinical suspicion alone.

Adult↗

[Bacteremia in the county of Ribe].

The Department of Microbiology at the Central Hospital of Esbjerg, established in 1987, serves the five hospitals in Ribe county, Denmark. From early on, the department has endeavoured to guide the hospital's antimicrobial policy. In order to investigate whether this involvement had any measurable impact on the antimicrobial resistance pattern in our region, we compared the resistance patterns of 212 strains isolated from the blood of bacteraemic patients in 1988 to those of 317 strains isolated in 1992. No increase in antibiotic resistance was revealed. This is noteworthy since new specialties have been established at the Central Hospital during this period, with an increased number of patients requiring antimicrobial therapy. It is important to survey the antibiotic resistance pattern closely, and that this is done locally.

Anti-Bacterial Agents↗

Fatty acid content and juice characteristics in black currant (Ribes nigrum L.) genotypes.

The fatty acid compositions of seeds from 29 black currant genotypes were determined using a rapid small-scale procedure. There was interest in alpha-linolenic, stearidonic, and, especially, gamma-linolenic acid (GLA) contents, and most samples showed values between 11.1 and 18.7%, between 2.5 and 4.5%, and between 11.6 and 17.4%, respectively. However, six genotypes exhibited gamma-linolenic contents >18%, and values >20% were recorded in four of these genotypes. The fatty acid contents of the six genotypes were also analyzed by using a conventional procedure, and only slight differences in fatty acid composition were found between the two methods. Although GLA content was not strongly correlated with juice parameters, some genotypes had both high GLA contents and desirable juice characteristics. The results obtained provide evidence that it is possible to select for GLA contents without negatively affecting juice quality, and both aspects can be combined in a single cultivar, thereby increasing the added value of the whole fruit.

Beverages↗

Comparison of isolation methods for the determination of important aroma compounds in black currant (Ribes nigrum L.) juice, using nasal impact frequency profiling.

The influence of isolation method on the determination of important aroma compounds in black currant juice was investigated by surface of nasal impact frequency (SNIF) gas chromatography-olfactometry (GC-O). The applied methods were solvent extraction, static headspace, and purge and trap using 15 and 60 min of purge time. By the four methods, a total of 59 odors were observed, and, of these, 44 corresponded to compounds that could be identified. For the headspace methods increasing purge volumes resulted in recoveries of additional, less volatile compounds. The main compound groups recovered by the headspace methods were esters and terpenes, whereas compounds recovered by solvent extraction were not as dominated by fruity odors. For most compounds there was agreement between the size of the SNIF value obtained by GC-O and the amount of the measurable compound found by gas chromatography-mass spectrometry.

Beverages↗

Influence of thermal treatment on black currant (Ribes nigrum L.) juice aroma.

The influence of thermal treatment on black currant juice aroma was investigated in temperature and time ranges relevant for black currant juice concentration processes, namely, 45, 60, 75, and 90 degrees C. Forty-nine aroma compounds were quantified, and the thermal treatment resulted in concentration increases of most terpenes, aldehydes, furans, and phenols, whereas the concentration of esters slightly decreased. Higher temperatures and longer exposure times had larger effects on the aroma compounds. Odor triangle tests showed no sensory difference between pasteurized juice and juice heated at 60 degrees C, whereas juice heated at 90 degrees C differed significantly from pasteurized juice. It is concluded that a 90 degrees C thermal treatment of black currant juice, which is in the temperature range used for conventional evaporation of black currant juice, has an effect on the aroma and sensory properties.

Beverages↗

Volatile monoterpenes in black currant (Ribes nigrum L.) juice: effects of heating and enzymatic treatment by beta-glucosidase.

Changes of terpenes in black currant juice induced by the action of heat were investigated in the present study. Limonene, alpha-terpinene, linalool, alpha-terpineol, 4-terpineol, and menthol added to either black currant juice or a model system were thermally treated at 90 degrees C for 30 min. Similar heat-induced decreases in the concentration of the terpenes were observed in the two systems. The concentration of a range of terpene hydrocarbons and oxygenated terpenes increased, alpha-terpineol being a main conversion product of most of the examined compounds. In the main, the measured loss of compounds exceeded the detected concentrations of products formed. In addition, determination of glycosidically bound terpenes in the juice was carried out by two methods of enzymatic hydrolysis, namely, addition of beta-glucosidase to an Amberlite XAD-2 isolate or directly to black currant juice. The two methods gave the same patterns of seven released volatile aglyconic terpenes. However, none of the released terpenes are important for the odor of black currant juice.

Beverages↗

Extraction of polyphenols from processed black currant (Ribes nigrum L.) residues.

The total phenol and anthocyanin contents of black currant pomace and black currant press residue (BPR) extracts, extracted with formic acid in methanol or with methanol/water/acetic acid, were studied. Anthocyanins and other phenols were identified by means of reversed phase HPLC, and differences between the two plant materials were monitored. In all BPR extracts, phenol levels, determined by the Folin-Ciocalteu method, were 8-9 times higher than in the pomace extracts. Acid hydrolysis liberated a much higher concentration of phenols from the pomace than from the black currant press residue. HPLC analysis revealed that delphinidin-3-O-glucoside, delphinidin-3-O-rutinoside, cyanidin-3-O-glucoside, and cyanidin-3-O-rutinoside were the major anthocyanins and constituted the main phenol class ( approximately 90%) in both types of black currant tissues tested. However, anthocyanins were present in considerably lower amounts in the pomace than in the BPR. In accordance with the total phenol content, the antioxidant activity determined by scavenging of 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) radical cation, the ABTS(*)(+) assay, showed that BPR extracts prepared by solvent extraction exhibited significantly higher (7-10 times) radical scavenging activity than the pomace extracts, and BPR anthocyanins contributed significantly (74 and 77%) to the observed high radical scavenging capacity of the corresponding extracts.

Anthocyanins↗