Effect of the anthraquinones emodin and physcion on availability of selected soil inorganic ions

The effects of emodin and physcion, two anthraquinones involved in Polygonum sachalinense allelopathy, were studied in soils amended with 5, 10 and 15 mg 100 g^-1 soil of each compound, and with their mixtures. Recovery of each compound and its effects on availability of soil Mn⁺⁺, Na⁺, K⁺, Mg⁺⁺, Ca⁺⁺ and PO₄^3- were monitored. Total phenolic content of each soil was determined to study the role of degraded phenolics. Soil amended with 5 mg of emodin and physcion gave maximum recovery of the two anthraquinones. Soil amended with different amounts of two anthraquinones and their mixture had significant lower values for pH compared to control. In general, both anthraquinones affect availability of soil inorganic ions. Compared to unamended control soil, a significant decrease in Mn⁺⁺ availability, and an increase in Na⁺ and K⁺ availability when emodin and physcion were added to the soil was observed. A correlation among soil inorganic ions, relative recovery of two compounds, and total phenolic content of amended soils was observed. Results indicate that emodin and physcion influence the availability of soil inorganic ions. The significance of the effect of allelopathic compounds on soil inorganic ions is discussed.     

Conversion of emodin to physcion by a cell-free preparation of Aspergillus parasiticus

Cultures of Aspergillus parasiticus contained 1.2 mg/litre of physcion. A cell-free extract of a 3-day-old culture of A. parasiticus catalysed the conversion of [³H]emodin and S-adenosyl-L-[Me-¹⁴C]methionine to ³H- and ¹⁴C-labelled physcion. Methylation of emodinanthrone was 9% of the methylation of emodin. Methylation of norsolorinic acid or versicolorin A, compounds associated with aflatoxin biosynthesis, was not detected.     

A naphthalene glucoside lactone from Rhamnus wightii

A new naphthalene glucoside lactone was isolated from the acetone extract of the stem bark of Rhamnus wightii. Cynodontin, chrysophanol, physcion, musizin, lupeol, sitosterol, 7-hydroxy-5-methoxyphthalide, emodin, sitosterol glycoside, β-sorigenin are the known compounds; β-sorigenin may be an artifact of its glucoside. The co-occurrence of two lactone ring compounds, 7-hydroxy-5-methoxyphthalide and the naphthalide glucoside is the significant feature of this plant.     

No clastogenic activity of a senna extract in the mouse micronucleus assay.

In previous studies, an analytically well-defined senna extract, commonly used as a laxative, gave positive responses in vitro in the Ames test and in the CHO assay. Therefore, the objective of this study was to investigate the genotoxic activity of the same senna extract in an in vivo genotoxicity assay by means of the generally acknowledged MNT. After administration of an oral dose of 2000 mg senna extract/kg to NMRI mice of both genders, which is equivalent to 119 mg potential rhein/kg, 5.74 mg potential aloeemodin/kg and 0. 28 mg potential emodin/kg, there were no elevated levels of micronuclei in bone marrow cells. Kinetic studies were performed in parallel to demonstrate target organ availability. Highest concentrations in the plasma were reached after 1 h with 3.4 microg rhein/ml and 0.065 microg aloeemodin/ml. In all cases, emodin was below the limit of quantification. From the results, the in vitro clastogenic activity of the senna extract could not be confirmed in the mouse micronucleus assay. Together with further negative in vivo genotoxicity studies with anthranoids, the conclusion can be drawn that there is no indication so far demonstrating a genotoxic risk for patients taking senna laxatives.     

Chemical constituents isolated from Polygala japonica leaves and their inhibitory effect on nitric oxide production in vitro

A methanolic extract of dried leaves of Polygala japonica Houtt (Polygalaceae) significantly attenuated nitric oxide production in lipopolysaccharide-simulated BV2 microglia. Five anthraquinones chrysophanol (1), emodin (2), aloe-emodin (3), emodin 8-O-beta-D-glucopyranoside (4) and trihydroxy anthraquinone (5), and four flavonoids kaempferol (6), chrysoeriol (7), kaempferol 3-gentiobioside (8) and isorhamnetin (9) were isolated from the methanolic extract using bioactivity-guided fractionation. Among them, compounds 1-4, 6 and 7 showed significant inhibitory effect on lipopolysaccharide-induced nitric oxide production in BV2 microglia at the concentrations ranging from 1.0 to 100.0 microM.     

Antifeedants against Acusta despesta from the Japanese cedar, Cryptomeria japonica

During our studies on the components in Japanese cedar, Cryptomeria japonica, we found that the crude methanol extract of C. japonica showed intense antifeeding activity against one snail species, Acusta despesta, which is well-known as a pest of many vegetables and crops. The active components in the extract were separated into the hexane and ethyl acetate soluble fractions. From the active ethyl acetate soluble fraction, two norlignans, sequirin-C and agatharesinol, were isolated and identified as the active compounds. Both compounds inhibited feeding behavior of A. despesta at 30 microg/cm2 and 40 microg/cm2 concentrations, respectively, when applied by an eggplant leaf or filter paper containing 20 microl of 5% sucrose solution.     

In vivo analgesic and anti-inflammatory activities of ursolic acid and oleanoic acid from Miconia albicans (Melastomataceae)

The aim of this work was to use in vivo models to evaluate the analgesic and anti-inflammatory activities of ursolic acid (UA) and oleanoic acid (OA), the major compounds isolated as an isomeric mixture from the crude methylene chloride extract of Miconia albicans aerial parts in an attempt to clarify if these compounds are responsible for the analgesic properties displayed by this plant. Ursolic acid inhibited abdominal constriction in a dose-dependent manner, and the result obtained at a content of 40 mg kg(-1) was similar to that produced by administration of acetylsalicylic acid at a content of 100 mg kg(-1). Both acids reduced the number of paw licks in the second phase of the formalin test, and both of them displayed a significant anti-inflammatory effect at a content of 40 mg kg(-1). It is noteworthy that the administration of the isolated mixture, containing 65% ursolic acid/35% oleanolic acid, did not display significant analgesic and anti-inflammatory activities. On the basis of the obtained results, considering that the mixture of UA and OA was poorly active, it is suggested that other compounds, rather than UA and OA, should be responsible for the evaluated activities in the crude extract, since the crude extract samples displayed good activities.     

Antifeedants against Acusta despesta from the Japanese Cedar,Cryptomeria japonica II

The hexane-soluble fr. was found to be as intense in antifeeding activity as the crude methnol extract of Cryptomeria japonica against Acusta despesta. This hexane soluble-fraction was used to isolate and identify two sesquiterpenols, (?)-cubebol and (+)-2,7(14),10-bisabolatrien-1-ol-4-one, as the active compounds. Both compounds strongly inhibited the feeding behavior of A. despesta at 120 μg/cm² and 80 μg/cm² concentrations, respectively.     

Anti-inflammatory and antioxidant effects of Croton celtidifolius bark.

Croton celtidifolius Baill commonly known as "sangue-de-adave" is a tree found in the Atlantic Forest of south of Brazil, mainly in Santa Catarina. The bark and leaf infusions of this medicinal plant have been popularly used for the treatment of inflammatory diseases. In this study we evaluated the anti-inflammatory and antioxidant properties of crude extract (CE), aqueous fraction (AqF), ethyl acetate fraction (EAF), butanolic fraction (BuF) and catechin, gallocatechin and sub-fractions, 19SF, 35SF and 63SF that contained a mixture of proanthocyanidins and were derived from the EAF fraction. The CE, AqF, EAF, BuF, catechin and sub-fractions 35SF and 63SF reduced paw edema induced by carrageenan. The CE, fractions, sub-fractions and isolated compounds showed antioxidant properties in vitro, all were able to scavenge superoxide anions at a concentration of 100 microg ml(-1). The EAF, catechin and gallocatechin were most effective in the deoxyribose assay, IC50 0.69 (0.44-1.06), 0.20 (0.11-0.39), 0.55 (0.28-1.08) microg x ml(-1) respectively. The CE and other fractions and sub-fractions inhibited deoxyribose degradation up to 1 microg x ml(-1). In the hydrophobic system only AqF did not show lipid peroxidation inhibition. The CE, other fractions, sub-fractions and isolated compounds inhibited lipidid peroxidation only at a concentration of 100 microg x ml(-1). In summary, this study demonstrates that Croton celtidifolius bark has significant anti-inflammatory and antioxidant activity.     

Microbial glycosylation of four free anthraquinones by Absidia coerulea

Absidia coerulea transformed four anthraquinones from rhubarb, chrysophanol, physcion, emodin and aloe-emodin to their corresponding glycosylated metabolites. The structures of the products were characterized as chrysophanol 8-O-beta-D-glucoside, physcion 8-O-beta-D-glucoside, emodin 6-O-beta-D-glucoside, and aloe-emodin 1-O-beta-D-glucoside, respectively.     

Anti-inflammatory, analgesic and antipyretic activities of Physalis minima Linn

In our present investigation, the crude methanol extract and chloroform fraction of the whole plant of Physalis minima Linn (Solanaceae) was investigated for anti-inflammatory, analgesic and antipyretic activities in NMRI mice and Wistar rats of either sex at 200 and 400 mg/kg, respectively. Various established in-vivo model's were used during the study. Both crude extract and chloroform fraction showed marked anti-inflammatory and analgesic activities as compared to a control at tested doses. The antipyretic potential of the crude extract and chloroform were insignificant in the Brewer's yeast fever model. Therefore, the whole plant of Physalis minima Linn could be considered as a potential candidate for bioactivity-guided isolation of natural anti-inflammatory and analgesic agents.     

扛板归根化学成分研究

从扛板归(Polygonum perfoliatum)根中分离鉴定出7种化合物,其结构分别为β-谷甾醇(1)、反式-对羟基肉桂酸甲酯(2)、槲皮素(3)、槲皮素-3-O-β-D-葡萄糖甙(4)、大黄素(5)、大黄素甲醚(6)和芦荟大黄素(7)。这些成分均为首次从扛板归根中分离得到。     

Metabolic products of microorganisms. 192. The anthraquinones of the Aspergillus glaucus group. II. Biological activity

From the mycelia of Aspergillus cristatus the following anthraquionic pigments were isolated: catenarin, emodin, erythroglaucin, rubrocristin, physcion, physcion-9-anthrone, questin, viocristin, and isoviocristin. The latter two do not belong to the 9, 10-anthraquinone series but to the 1,4-anthraquinones, and so far they have not been reported among naturally occurring quinones.Emodin, catenarin, viocristin, and isoviocristin snowed antibacterial activity with minimal inhibitory concentrations ranging from 1–10 g/ml. In Bacillus brevis catenarin and emodin inhibited the incorporation of uracil and leucine preferentially. At higher concentrations the incorporation of thymidine into the trichloroacetic acid-precipitable fraction of cells was also affected. In the presence of viocristin or isoviocristin all three macromolecular syntheses came to a halt. Rubrocristin, erythroglaucin, and physcion showed no significant inhibitory effects.In Ehrlich ascites carcinoma cells catenarin, emodin, and viocristin inhibited the incorporation of uridine and thymidine. The incorporation of leucine was hardly affected.In vitro, inhibition of DNA-dependent RNA polymerase from Escherichia coli by catenarin and to a lesser extent by emodin was observed, whereas rubrocristin (catenarin-8-methyl ether), physcion, and erythroglaucin were not active.Abbreviations MIC minimal inhibitory concentration - TCA trichloroacetic acid - ECA Ehrlich ascites carcinoma Metabolic Products of Microorganisms. 191. W. Keller-Schierlein und B. Joos; Über das 4-Oxohomotyrosin, ein Abbauprodukt des Echinocandins. Helv. Chim. Acta (in press)     

Phytochemical Profiling and Compound Isolation of Cissus rhombifolia Vahl. Leaves Aqueous Methanolic Extract with the Evaluation of Its Anti-Inflammatory Effect Using Lipopolysaccharide-Induced Inflammation in RAW 264.7 Cells

The inflammatory disorders represent a serious health issue. Certain Cissus species possess anti-inflammatory effect. Cissus rhombifolia Vahl. leaves’ anti-inflammatory activities and phytoconstituents are poorly characterized. In this study, 38 constituents were tentatively characterized in Cissus rhombifolia Vahl. leaves’ aqueous methanolic extract (CRLE) using high-performance liquid chromatography combined with mass spectrometry (HPLC/MS) and Proton Nuclear Magnetic Resonance (¹H-NMR). Myricetin, β-amyrin, and alliospiroside A, were isolated from CRLE using column chromatography. The anti-inflammatory effect of CRLE and its isolated compounds were studied in lipopolysaccharide (LPS)-induced RAW 264.7 cells. 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT assay) was used to assess how CRLE and its isolated compounds affected cell viability. Further, its effects on the production of intracellular NO, and inflammatory cytokines cyclooxygenase-2 (COX-2), tumor necrosis factor alpha (TNF-α), and interleukin 6 (IL-6) were assessed by the Griess test, and cytokine enzyme-linked immunosorbent assays, respectively. CRLE and its isolated compounds, myricetin, β-amyrin, and alliospiroside A decreased the NO production. Western blotting was performed to assess the protein expression levels of the inflammatory cytokines inducible nitric oxide synthase (iNOS). Alliospiroside A downregulated IL-6, TNF-α, and COX-2 and inhibited the expression of iNOS. CRLE and its compounds represent effective alternative candidate to treat inflammatory diseases.     

Pharmacological assay of Cordia verbenacea V: oral and topical anti-inflammatory activity, analgesic effect and fetus toxicity of a crude leaf extract

Cordia verbenacea D.C. (Borraginaceae) is a perennial bush plant that grows widely along the southeastern coast of Brazil. Its leaves have been used in folk medicine for their anti-ulcer, anti-inflammatory and cicatrizing activities. We have already described the anti-inflammatory properties of C. verbenacea and its low toxicity in different acute animal models. In the present study, we investigated the anti-inflammatory activity in sub-chronic animal models of a crude leaf lyophilized extract when administered by oral route or topically applied, and concomitantly, its analgesic potency and toxicity to the fetus. Topical administration of the extract inhibited nystatin-induced edema proportionally to the doses used, and this effect at a dose of 4.56 mg/kg body wt. was similar to that observed with 6.0 mg/kg body wt. of naproxen. In miconazole-induced edema, the leaf extract at a dose of 1.24 mg/kg body wt., orally administered, has a very similar effect as compared to nimezulide (2.5 mg/kg body wt.) and dexamethasone (0.2 mg/kg body wt.). At an oral dose of 2.48 mg/kg body wt. the extract showed a very low analgesic effect, and total absence of fetus toxicity at doses of less than 7.44 mg/kg body wt.     

猴头菌培养物化学成分研究

为研究猴头菌培养物的化学成分,利用硅胶柱色谱、Sephadex LH-20柱色谱、重结晶等分离技术进行系统的分离纯化,根据理化性质及光谱数据鉴定结构。结果从猴头菌固体培养物中共分离得到10个化合物,分别为大黄酚、大黄素甲醚、大黄素、芦荟大黄素、大黄酸、麦角甾醇、β-谷甾醇、5α-豆甾-3,6-二酮、麦角甾醇过氧化物、3-吲哚甲醛。其中化合物1⁵,8,10均为首次从猴头菌培养物中分离得到。     

Anti-inflammatory,analgesic and antipyretic activities of Physalis minima Linn

In our present investigation, the crude methanol extract and chloroform fraction of the whole plant of Physalis minima Linn (Solanaceae) was investigated for anti-inflammatory, analgesic and antipyretic activities in NMRI mice and Wistar rats of either sex at 200 and 400 mg/kg, respectively. Various established in-vivo model's were used during the study. Both crude extract and chloroform fraction showed marked anti-inflammatory and analgesic activities as compared to a control at tested doses. The antipyretic potential of the crude extract and chloroform were insignificant in the Brewer's yeast fever model. Therefore, the whole plant of Physalis minima Linn could be considered as a potential candidate for bioactivity-guided isolation of natural anti-inflammatory and analgesic agents.     

Alterations in secondary metabolism of aposymbiotically grown mycobionts of Xanthoria elegans and cultured resynthesis stages

HPLC analyses of Xanthoria elegans cultivated on different media and either aposymbiontically or with its photobiont revealed that the carbon source and the presence of the algal partner have an impact on the secondary metabolism of the mycobiont. The aposymbiotically (without photobiont) grown mycobiont contained up to 70% more of the main compounds in its thallus than in resynthesis stage. Although this is speculative, the induction of the polyketide pathway may be a feedback mechanism to the absence of the photobiont. All cultures produce a variety of substances which were not detectable in the voucher specimen. Besides physcion (the major substance), we were able to identify emodin as well as physcion-bisanthrone, teloschistin monoacetate and derivatives. A strong inducible effect on the production of physcion, physcion-bisanthrone and on their precursors and derivatives was found for mannitol. By contrast, supplementation of ribitol had negligible effects, if any, on polyketide quantities although it is the main carbon source for the mycobiont in free-living lichens with Trebouxia photobiont.