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A benzoquinone and flavonoids from Cyperus alopecuroides.

A benzoquinone, named alopecuquinone, was isolated from the ethanol extract of the inflorescences of Cyperus alopecuroides. Its structure was primarily elucidated by spectroscopic analysis including 1H, 13C NMR, APT, HMQC, 1H-1H COSY and CIMS. The known flavonoids, vicenin 2, orientin, diosmetin, quercetin 3,3'-dimethyl ether and its 3,4'-dimethyl ether, were also isolated and characterized. The ethanol extract of the plant material showed moderate estrogenic activity using a strain of Saccharomyces cerevisiae.

Benzoquinones↗

Structures of new sesquiterpenes and hepatoprotective constituents from the Egyptian herbal medicine Cyperus longus.

Six new sesquiterpenes, cyperusols A(1) (1), A(2) (2), B(1) (3), B(2) (4), C (5), and D (6), together with two monoterpenes and 13 sesquiterpenes were isolated from an Egyptian herbal medicine, the whole plants of Cyperus longus. The stereostructures of the new sesquiterpenes were determined on the basis of chemical and physicochemical evidence. In addition, the principal constituents were found to exhibit inhibitory activity on D-galactosamine-induced cytotoxicity in primary cultured mouse hepatocytes.

Animals↗

The fate of organic matter in a papyrus (Cyperus papyrus L.) dominated tropical wetland ecosystem in Nyanza Gulf (Lake Victoria, Kenya) inferred from delta13C and delta15N analysis.

Papyrus swamps usually form at the interface between river inlet and open lake. From one such wetland ecosystem (the Kibos system located in the Nyanza Gulf, Lake Victoria, Kenya), three sediment cores were recovered using piston corer in order to determine the fate of organic matter derived from papyrus and possible nutrient pathways in this system. The coring represented a transect from the river through the floating papyrus mat to the lake. Two short cores were retrieved from the lake and river. One long core (2 m) was recovered on a floating papyrus mat. The C:N ratio showed similar trends down core from the three locations. This may possibly be due to diagenic processes such as autolysis, dissolution and microbial mineralisation occurring in the sediments. Statistical analysis through one-way ANOVA revealed no significant differences in the C:N ratios between stations. Results of the stable carbon isotope ratios revealed that the delta(13)C of the river and lake samples were persistently more negative than -20 per thousand over the whole profile indicating possible contribution from terrestrial derived carbon. Regarding the floating mat core, the delta(13)C values ranged from -18.99 per thousand on the top of the floating mat but gradually increased to -16.82 per thousand towards the bottom of the core indicating possible contribution of carbon from Cyperus papyrus that has a delta(13)C value of -13.45+/-0.62 per thousand. Statistical analysis through one-way ANOVA revealed significant differences in the delta(13)C values between stations. The stable nitrogen isotope values were highly positive both in the river and in the lake station (delta(15)N > 10 per thousand), indicating possible contamination from sewage wastes. Values in the swamp were less positive suggesting first, the formation of ammonium depleted in (15)N from intense organic matter mineralisation, secondly indicating the delta(15)N signal of papyrus and, finally that nitrogen fixation processes were possibly occurring in the swamp. Statistical analysis through one-way ANOVA revealed significant differences in the delta(15)N values between stations. The stable isotope findings suggested that carbon derived from papyrus is retained in the swamp. Impoverished oxygen concentration in the swamp suggests high mineralisation of organic matter in the swamp indicating that the retained papyrus-derived carbon is largely respired. We conclude that further studies should be undertaken to determine the respiration rates in the wetland.

Carbon Isotopes↗

Low growth temperatures modify the efficiency of light use by photosystem II for CO2 assimilation in leaves of two chilling-tolerant C4 species, Cyperus longus L. and Miscanthus x giganteus.

Two C4 plants, Miscanthus x giganteus and Cyperus longus L., were grown at suboptimal growth temperatures and the relationships between the quantum efficiencies of photosynthetic electron transport through photosystem II (PSII) (PSII operating efficiency; Fq'/Fm') and CO2 assimilation (phiCO2) in leaves were examined. When M. x giganteus was grown at 10 degrees C, the ratio of the PSII operating efficiency to phiCO2 increased relative to that found in leaves grown at 14 and 25 degrees C. Similar increases in the Fq'/Fm': phiCO2 occurred in the leaves of two C. longus ecotypes when the plants were grown at 17 degrees C, compared to 25 degrees C. These elevations of Fq'/Fm': phiCO2 at low growth temperatures were not attributable to the development of anthocyanins, as has been suggested for maize, and were indicative of the operation of an alternative sink to CO2 assimilation for photosynthetic reducing equivalents, possibly oxygen reduction via a Mehler reaction, which would act as a mechanism for protection of PSII from photoinactivation and damage. Furthermore, in M. x giganteus grown at 10 degrees C, further protection of PSII was effected by a 20-fold increase in zeaxanthin content in dark-adapted leaves, which was associated with much higher levels of non-photochemical quenching of excitation energy, compared to that observed in leaves grown at 14 and 25 degrees C. These differences may explain the long growing season and remarkable productivity of this C4 plant in cool climates, even in comparison to other C4 species such as C. longus, which occur naturally in such climates.

Adaptation, Physiological↗

Effects of methylated derivatives of Luteolin isolated from Cyperus alopecuroides in rat H4IIE hepatoma cells*.

Polyphenols are ubiquitous substances in human diet. Their antioxidative, antiinflammatory and antiviral effects are of interest for human health, and polyphenols such as luteolin are used at high concentrations in food supplements. Luteolin is metabolized to glucuronides, but also to methylated derivatives. For example, O-methylation of the catechol group mediated by the catechol-O-methyl transferase, is an important step in flavonoid metabolism. The aim of this project was to determine the effect of O-methylation on antioxidative capacity and cytotoxicity of luteolin in H4IIE rat hepatoma cells. Therefore we analyzed the effects of luteolin 5,3'-dimethylether, isolated from the flowers of foxtail flatsedge (Cyperus alopecuroides) and luteolin 5,7,3',4'-tetramethylether compared to the non-methylated flavonoid luteolin. The antioxidative potential of luteolin was lowered by methylation, an effect that seems to be mediated by masking of the catechol moiety in the B ring. The cytotoxic potential of luteolin 5,3'-dimethylether is comparable to luteolin, but the tetramethylether showed no cytotoxic effect. The cytotoxic effect of luteolin but not luteolin 5,3'-dimethylether was mediated via apoptosis (caspase-3 activation). We conclude that the O-methylation of luteolin led to a decreased radical-scavenging activity and to a reduction in the apoptotic potential of the flavonoid.

Animals↗

Investigations on rhizoplane Actinobacteria communities of papyrus (Cyperus papyrus) from an Egyptian wetland.

Wetlands have important global ecological functions, which include carbon storage and water interception. Wetland contributes to the maintenance of regional and global biodiversity. Though many important wetland ecological functions are based on microbial metabolism, we have scanty knowledge on microbial diversity in wetlands. Plant rhizoplane habitats are considered to harbor highly diverse bacterial communities. Most of the floating mats on river Nile are dominated by papyrus (Cyperus papyrus). Papyrus root samples were collected from a floating mat at the "Gold Island" inside the Nile River at Cairo, Egypt in February 1996 and May 1997 in order to investigate the rhizoplane actinobacteria communities. The root-tip regions were cut off, repeatedly washed, macerated and plated. Using the plate-count technique with three actinobacteria media, an average of 2.1 x 10(4) CFUg-1 root actinobacteria were obtained. All actinobacteria colonies were isolated, purified and investigated by classical and molecular methods. In the papyrus rhizoplane Streptomyces anulatus, Micromonospora sp., Rhodococcus luteus, Verrucosispora gifhornensis and Aureobacterium liquefaciens dominated, moreover Actinoplanes utahensis, and Str. diastaticus were also present. The physiological traits of the members of dominant groups revealed that these bacteria might be active in the rhizoplane and can be present there is their vegetative forms.

Actinobacteria↗

Biosynthetic pathway of insect juvenile hormone III in cell suspension cultures of the sedge Cyperus iria.

In most insect species, juvenile hormones regulate critical physiological processes such as metamorphosis and reproduction. In insects, these sesquiterpenoids are synthesized by retrocerebral endocrine organs, the corpora allata, via the classical mevalonate (MVA) pathway. One of these compounds, juvenile hormone III (JH III), has also been identified in the sedge Cyperus iria. In higher plants, biosynthesis of the sesquiterpenoid backbone may proceed through two distinct pathways: the MVA pathway or the 2C-methyl erythritol 4-phosphate pathway or through a combination of both pathways. Cell suspension cultures of C. iria were used to elucidate the biosynthetic pathway of JH III in the plant. Enzyme inhibition and labeling studies conclusively demonstrated that the biosynthesis of the sesquiterpenoid backbone of JH III proceeds via the MVA pathway. Inhibitor and precursor feeding studies also suggest that later steps of JH III biosynthesis in C. iria are similar to the insect pathway and that the final enzymatic reaction in JH III biosynthesis is catalyzed by a cytochrome P(450) monooxygenase.

Aldose-Ketose Isomerases↗

The effect of wastewater discharge on biomass production and nutrient content of Cyperus papyrus and Miscanthidium violaceum in the Nakivubo wetland, Kampala, Uganda.

The nutrient content of representative plant parts and biomass production in the Nakivubo wetland, correlation of these with the wastewater flow patterns and determination of nutrient uptake, storage and biomass production of Cyperus papyrus (papyrus) and Miscanthidium violaceum was studied. On average papyrus vegetation under the influence of wastewater had higher nutrient content in the above ground biomass (1.6% N and 0.23% P on dry weight basis) than those not affected (0.98% N and 0.18% P). The biomass varied between 3,529-5,844 g/m2 and 883-1,156 g/m2 in the two respective sites. The juvenile plants of papyrus and Miscanthidium had higher concentrations of P and N in their organs compared to the mature ones. Considering the nutrients stored by the dominant vegetation and the current flow patterns of wastewater in the Nakivubo wetland, harvesting of the above ground biomass once a year, would remove 7.7% of the N input and 15.8% of the P input of the annual total load entering the wetland. However, if the wetland is bio-manipulated and the wastewater flow distributed over the whole wetland, up to 70% nitrogen and 76% phosphorus would be removed by harvesting above ground papyrus biomass.

Biodegradation, Environmental↗

The repellant and antifeedant properties of Cyperus articulatus against Tribolium casteneum Hbst.

Cyperus articulatus is an insect repellant plant commonly found in Northern Nigeria and used traditionally in pest control. The light petroleum and methanol extracts of the plant's rhizome were evaluated against Tribolium casteneum Hbst (the red flour beetle) using standard techniques. The methanol extract showed more antifeedant property than the light petroleum extract, while both the extracts were observed to have similar repellant actions.

Animals↗

Two novel flavans from Cyperus conglomeratus.

Separation of the extract of the underground tubers of Cyperus conglomeratus Rottb. (family Cyperaceae) afforded, in addition to known compounds, two novel flavans, which were identified, by one and two dimensional NMR, MS and IR spectra, as 5-hydroxy-7,3',5'-trimethoxyflavan and 5,7-dihydroxy-3',5'-dimethoxy-6-prenylflavan.

Flavins↗

Microbial counts and invert sugars in juice extracts from stored tubers of Cyperus esculentus Linn. (earth almond).

The microbial populations and the levels of invert sugars in juice extracts from healthy tubers of Cyperus esculentus L. stored at 10, 20, 30 and 40 degrees C were determined. Bacterial counts increased with time and attained the peak on the 25th and 35th d at 40 and 30 degrees C respectively. Similar trends were obtained for the yeasts, but the peak counts were recorded on the 20th and 35th d at 40 and 30 degrees C respectively. At 10 and 20 degrees C, the counts, both for bacteria and yeasts increased throughout the 40-d period. Invert sugar levels increased throughout the investigation period at all the tested temperatures. Highest levels were recorded at about 30 and 40 degrees C while the lowest levels were obtained at 10 degrees C. Of the seven bacteria and five yeasts tested, only Saccharomyces rouxii, S. cerevisiae, Schizosaccharomyces sp., Pseudomonas chlororaphis, P. fluorescens and Bacillus subtilis brought about significant hydrolysis of sucrose in vitro. Results on the microbial populations and levels of invert sugars in raw juice extracts suggest that yeasts could possibly play a greater role than bacteria in the hydrolysis of sucrose in vivo.

Bacteria↗

Survey of aflatoxins and ochratoxin A in stored tubers of Cyperus esculentus L.

The mold incidence, moisture contents, pH and levels of mycotoxins (aflatoxins B1, G1 and ochratoxin A) on/of/in rootstock snack (tubers of Cyperus esculentus L.) samples were monitored during a 150-day storage period. Whereas the mold incidence, moisture and mycotoxin levels increased with storage time, the pH declined during the same period. Altogether, 12 fungal species, mostly toxigenic, including Aspergillus flavus, A. parasiticus and A. ochraceus were isolated. At collection period only 3 of the 9 snack samples analysed contained trace amounts of aflatoxins. By 120th day, all the 9 samples were contaminated and the average levels were 454 and 80 ppb for aflatoxin B1 and aflatoxin G1 respectively on the 150th day. Ochratoxin A was not detected before 120th day and then only at low levels, occurring in a maximum of four-samples and ranging between 10 and 80 ppb.

Aflatoxins↗

Antimalarial sesquiterpenes from tubers of Cyperus rotundus: structure of 10,12-peroxycalamenene, a sesquiterpene endoperoxide.

Activity-guided investigation of Cyperus rotundus tubers led to the isolation of patchoulenone, caryophyllene alpha-oxide, 10,12-peroxycalamenene and 4,7-dimethyl-1-tetralone. The antimalarial activities of these compounds are in the range of EC50 10(-4)-10(-6) M, with the novel endoperoxide sesquiterpene, 10,12-peroxycalamenene, exhibiting the strongest effect at EC50 2.33 x 10(-6) M.

Animals↗

Effects of coal gasification slag as a substrate for the plant Cyperus esculentus and the worm Eisenia fetida.

A further development of the coal gasification process will result in an increase of the amount of coal gasification slag (CGS). As yet little is known about the effects of storage in uncovered dumps. If there are any environmental effects, they are most likely caused by accumulation of metals from the CGS or by unacceptable physical properties of the CGS. Growth inhibition, mortality, and metal accumulation were analyzed for the plant Cyperus esculentus and the worm Eisenia fetida on CGS substrate. Pulverized fuel ash (PFA) was used as a reference. Both in the substrate and in tissues the concentrations of the cations Cu, Ni, Pb, and Zn and the anions As, B, Cr, Mo, Sb, and Se were determined. The availability of anions for C. esculentus and for E. fetida is greater in PFA than in CGS. The extent and rate of uptake of anionic metals by the plants is on the whole higher in the wetland situation. The availability of metals, expressed as the concentration factor (CF), in most cases appears to be smaller than 1 for nearly all elements. In E. fetida a CF greater than 1 was found only for the element As, in PFA substrate and 50% CGS. In C. esculentus a CF greater than 1 was found for B and Mo in the PFA substrate as well.

Animals↗

Studies on protective effect of Cyperus scariosus extract on acetaminophen and CCl4-induced hepatotoxicity.

1. The hepatoprotective activity of aqueous-methanolic extract of Cyperus scariosus (Cyperaceae) was investigated against acetaminophen and CCl4-induced hepatic damage. 2. Acetaminophen produced 100% mortality at a dose of 1 g/kg in mice while pretreatment of animals with plant extract (500 mg/kg) reduced the death rate to 30%. 3. Acetaminophen at a dose of 640 mg/kg produced liver damage in rats as manifested by the rise in serum levels of alkaline phosphatase (ALP), glutamate oxaloacetate transaminase (GOT) and glutamate pyruvate transaminase (GPT) to 430 +/- 68, 867 +/- 305 and 732 +/- 212 IU/l (n = 10) respectively, compared to respective control values of 202 +/- 36, 59 +/- 14 and 38 +/- 7. 4. Pretreatment of rats with plant extract (500 mg/kg) significantly lowered (P < 0.05) the respective serum ALP; GOT and GPT levels to 192 +/- 31, 63 +/- 9 and 35 +/- 8. 5. The hepatotoxic dose of CCl4 (1.5 ml/kg; orally) raised serum ALP, GOT and GPT levels to 328 +/- 30, 493 +/- 102 and 357 +/- 109 IU/l (n = 10) respectively, compared to respective control values of 177 +/- 21, 106 +/- 15 and 47 +/- 12. 6. The same dose of plant extract (500 mg/kg) was able to significantly prevent (P < 0.05) CCl4-induced rise in serum enzymes and the estimated values of ALP, GOT and GPT were 220 +/- 30, 207 +/- 95 and 75 +/- 38, respectively. 7. The plant extract also prevented CCl4-induced prolongation in pentobarbital sleeping time confirming hepatoprotectivity.(ABSTRACT TRUNCATED AT 250 WORDS)

Acetaminophen↗

Constituents of the essential oil of Cyperus alopecuroides.

We have investigated the constituents of the essential oil of Cyperus alopecuroides. Three new compounds, the hydrocarbon, (-)-eudesma-2,4(15)-11-triene, the sesquiterpene alcohol (-)-eudesma-3,11-dien-5-ol and the diterpene hydrocarbon (-)-dolabella-3,7,18-triene were isolated and their structure elucidated.

Chromatography, Affinity↗

Sedative properties of the decoction of the rhizome of Cyperus articulatus.

The decoction of the rhizome of Cyperus articulatus is empirically used in several African countries in the treatment of a wide variety of human diseases. Studies were conducted in mice in order to determine scientifically the pharmacological properties of this medicinal herb. At the same time, the qualitative chemical characterisation of the total extract showed that C. articulatus contains flavonoids, saponins, tannins, terpenes and sugars. The total extract of the rhizome of C. articulatus does not appear to possess either anaesthetic or paralysing effects. In contrast, spontaneous motor activity is significantly reduced by the extract. However, when compared to diazepam, C. articulatus does not seem to have muscle relaxant effects. When associated with sodium thiopental or diazepam, the total extract facilitates sleep induction, and increases the total sleep time without any concomitant analgesic effect. These observations suggest that the rhizome of C. articulatus has pharmacological properties similar to those of sedatives. The sedative actions probably explain at least part of the therapeutic efficiency claimed for this plant in traditional medicine.

Animals↗

Anticonvulsant properties of the methanolic extract of Cyperus articulatus (Cyperaceae).

The methanolic extract of rhizomes of Cyperus articulatus, a plant used in traditional medicine in Africa and Latin America for many diseases, possesses anticonvulsant activity in mice. This extract protected mice against maximal electroshock (MES)- and pentylenetetrazol (PTZ)-induced seizures. It also delayed the onset of seizures induced by isonicotinic acid hydrazide and strongly antagonized N-methyl-D-aspartate-induced turning behavior. The ED(50) for protection against seizures was 306 (154-541) mg/kg intraperitoneally (i.p.) for the PTZ test and 1005 (797-1200) mg/kg i.p. for the MES test. The ED(50) of methanolic extract against N-methyl-D-aspartate-induced turning behavior was 875 (623-1123) mg/kg i.p. C. articulatus L. methanolic extract protected 54% of mice from seizures induced by strychnine at the dose of 1000 mg/kg i.p. but had no or a moderate effect only against picrotoxin- or bicuculline-induced seizures. With these effects, the rhizome of C. articulatus L. possesses anticonvulsant properties in animals that might explain its use as a traditional medicine for epilepsy in Africa.

Animals↗