Involvement of a neutrophil-mast cell axis in the effects of Piper malacophyllum (C. PESL) C. DC extract and its isolated compounds in a mouse model of dysmenorrhoea.

The effects of Piper malacophyllum (C. Pesl) C. DC extracts and its isolated compounds were analysed in a mouse model of primary dysmenorrhoea (PD). Female Swiss mice (6-8 weeks old) on proestrus were intraperitoneally treated with estradiol benzoate for 3 days, to induce PD. Twenty-four hours later, animals were treated 24 h later with vehicle, plant extract, gibbilimbol B, 4,6-dimethoxy-5-E-phenylbutenolide, mixture of 4,6-dimethoxy-5-E-phenylbutenolide and 4,6-dimethoxy-5-Z-phenylbutenolide, or ibuprofen. One hour later, oxytocin was injected and the numbers of abdominal writhing were counted. Then, mice were euthanized and uteri were collected for morphometrical and histological analyses. The effects of P. malacophyllum in inflammation were investigated in mouse peritoneal neutrophils culture stimulated with LPS or fMLP (chemotaxis and mediator release). Finally, uterus contractile and relaxing responses were assessed. Similar to ibuprofen, P. malacophyllum extract and isolated compounds reduced abdominal writhing in mice with PD. Histology indicated a marked neutrophil and mast cell infiltrate in the uterus of PD animals which was attenuated by the extract. The compounds and the extract reduced neutrophil chemotaxis and inflammatory mediator release by these cells. Reduced TNF levels were also observed in uteri of PD mice treated with P. malacophyllum. The extract did not affect spontaneous uterine contractions nor those induced by carbachol or KCl. However, it caused relaxation of oxytocin-induced uterine contraction, an effect blunted by H1 receptor antagonist. Overall the results indicate that P. malacophyllum may represent interesting natural tools for reliving PD symptoms, reducing the triad of pain, inflammation and spasmodic uterus behaviour.

Phytochemical Analysis and Antinociceptive Properties of Hydroalcoholic Extracts of Aleurites moluccanus Bark.

Aleurites moluccanus is used in folk medicine to treat many diseases including pain and inflammatory processes in general. Considering the potential of the leaf extract, evidenced in a previous study, the present study investigates the antinociceptive and anti-inflammatory properties of the hydroethanolic extract of A. moluccanus bark and isolated compounds in animal models of pain. The antinociceptive and anti-inflammatory activities of A. moluccanus bark were evaluated through hyperalgesia induced by carrageenan, PGE2, cytokines, bradykinin, epinephrine, Freund's complete adjuvant, and lipopolysaccharide. Five compounds were isolated from the dichloromethane bark extract: acetyl aleuritolic acid, atraric acid, spruceanol, (5ß,10α)-12-hydroxy-13-methoxy-8,11,13-podocarpatrien-3-one and sonderianol. To optimize the extraction conditions, ethanol 50, 70, and 90°GL were used as extracting solvent, in a 1 : 20 (w/v) drug : solvent ratio, under stirring at room temperature for 4 h. The extracts were named AMC50, AMC70, and AMC90, respectively. These extracts were administered to mice (250 mg/kg, p. o.) with reduced mechanical hyperalgesia activity in the carrageenan test. Of these, AMC90 showed the best results. Pure (5ß,10α)-12-hydroxy-13-methoxy-8,11,13-podocarpatrien-3-one showed a beneficial effect for up to 48 hours after the administration of carrageenan, while acetyl aleuritolic acid was effective only in the first hour. AMC90 was able to reverse the analgesia induced only by prostaglandin E2 and tumor necrosis factor. We also induced hyperalgesia using the lipopolysaccharide and Freund's complete adjuvant models, with positive results. These results support the antinociceptive and anti-inflammatory activity of A. moluccanus bark extract. The observed effects are partly due to the presence of acetyl aleuritolic acid, atraric acid, and (5ß,10α)-12-hydroxy-13-methoxy-8,11,13-podocarpatrien-3-one.

In silico and in vitro degradation studies of isolated phloroglucinols eugenial C and eugenial D from Eugenia umbelliflora fruits.

INTRODUCTION: Eugenia umbelliflora fruits are an important source of phloroglucinols, as eugenial C and eugenial D, related to antimicrobial activity against Staphylococcus aureus. However, for the establishment of new antimicrobial substances, it is essential to know their stability profile, in view of driving the administration route and the release system development. METHODOLOGY: The in silico approaches, based on the Fukui indices and bond dissociation analysis, were performed. Eugenial C and eugenial D, isolated from the green fruits of E. umbelliflora, with purity > 90%, were submitted to stress degradation including: acid (0.5 mM hydrochloric acid) and alkaline (0.5 mM sodium hydroxide) hydrolysis, and oxidation (0.25% hydrogen peroxide), in different periods, monitoring by high-performance liquid chromatography with ultraviolet detector (HPLC-UV). Eugenial C was also submitted to UV-visible radiation (2,400 lux/h) and dry/humid heating (40°C, 75% relative humidity). RESULTS: In silico studies indicated that both molecules have regions of high susceptibility to nucleophilic and electrophilic attack as well as sites likely to suffer auto-oxidation. Under in vitro tests, both phloroglucinols proved to be very unstable under hydrolysis (eugenial C and D were degraded 23.8% and 89.0% in acid and 78.4% and 97.8% in alkaline conditions, respectively) and oxidation (eugenial C and D degraded 31.9% and 28.6%, respectively), both during 5 min. Eugenial C degraded 12.6% and 63.8% under dry and humid heat, respectively, without photosensitivity. CONCLUSION: The in vitro stress tests monitored by HPLC-UV were in agreement with in silico degradation prediction. Phloroglucinols could be unstable if administered by oral route and also under environmental conditions demanding a protective release system.

Improvement in phloroglucinol compound extracted from different parts of Eugenia umbelliflora monitored by LC-UV and antimicrobial activity.

The phloroglucinol eugenial C, eugenial D and eugenial E are the main active compounds in Eugenia umbelliflora fruits. This study aims to evaluate the extraction conditions of E. umbelliflora, using ethanol as solvent, focusing on the phloroglucinol and antimicrobial activity. In order to optimize the extraction conditions, ethanol 50, 70 and 90 oGL was used as a solvent in the proportions of 1:20 (w/v) of drug:solvent ratio (D:S), stirring (330 rpm) at room temperature during 4 h, monitored by LC-UV and antimicrobial assay. The LC-UV method developed was linear over a concentration range of 3.4-68.0, 5.3-106.0 and 5.0-100.8 µg.mL-1 of eugenial C, eugenial D and eugenial E, having LOQ of 1.68, 1.33 and 0.8 µg.mL-1, respectively. The fruits showed the best herbal raw material and showed the highest phloroglucinol concentration and activity against S. aureus, when extracted with ethanol 90oGL, during 4 h, at 1:20 of D:S.

Aleurites moluccana (L.) Willd. Leaves: Mechanical Antinociceptive Properties of a Standardized Dried Extract and Its Chemical Markers.

Seeking to develop a new analgesic phytomedicine, a spray-dried extract (SDE) of Aleurites moluccana (L.) Willd. leaves was developed in scale up (5 kg). The SDE was standardized at 3% w/w in relation to the flavonoid 2''-O-rhamnosylswertisin. The SDE batches were evaluated in relation to their physical, physiochemical, and pharmacological characteristics. The results demonstrated the reproducibility of the scale up SDE process which, when dosed orally, reduced carrageenan-induced mechanical hypernociception, with an ID(50)% of 443 mg/kg. Similar results were obtained with animals injected with complete Freund's adjuvant (CFA), in which SDE caused inhibition of 48 ± 4%. SDE was effective in preventing prostaglandin E2 (PGE2)-induced mechanical hypernociception (inhibition of 26 ± 10% and 33 ± 3%, at 250 and 500 mg/kg, respectively). Swertisin and 2''-O-rhamnosylswertisin isolated from the own extract were effective in inhibiting the hypernociceptive response induced by carrageenan (70 ± 2% and 50 ± 5%, resp.). Furthermore, 2''-O-rhamnosylswertisin was capable of significantly inhibiting the mechanical sensitization induced by CFA or PGE2, with inhibitions of 25 ± 3% and 94 ± 6%, respectively. These results suggest that the effects of SDE are related, at least in part, to the presence of these flavonoids.

Corticoid-like anti-inflammatory effect of Vochysia bifalcata Warm.: Preclinical evidence of efficacy and safety.

ETHNOPHARMACOLOGICAL RELEVANCE: Vochysia bifalcata is a Brazilian native tree commonly used for economic purpose in the reforestation and in the manufacture of products. However, the potential usage of other parts of the plant is usually wasted. Besides, other species of Vochysia are well known for its anti-inflammatory action. AIM OF THE STUDY: In this study we evaluate the possible anti-inflammatory activity of the hydroethanolic extract from the leaves of V. bifalcata in models of mice skin inflammation. MATERIALS AND METHODS: Effects of V. bifalcata were evaluated in croton oil-induced acute and chronic skin inflammation. The role of glucocorticoid receptors in the extract effect was assessed by using a glucocorticoid receptor antagonist and by a specific binding assay. Possible adverse effects were evaluated after multiple treatments with the extract in a skin atrophy model. RESULTS: Topical application of V. bifalcata reduced ear edema formation, cell infiltration and interleukin (IL)-6 and tumor necrosis factor (TNF)-α levels. In the chronic model, besides edema formation and cell infiltration, the extract inhibited epidermal hyperproliferation and Proliferating Cell Nuclear Antigen expression. V. bifalcata seems to act by biding to corticoid receptors, however it did not induce corticoid related undesirable effects. CONCLUSION: Hydroethanolic extract from leaves of V. bifalcata could be an interesting tool in the search for new anti-inflammatory and antiproliferative agents for the treatment of skin disorders.

Chemical and pharmacological aspects of the genus Calophyllum.

The Calophyllum genus (Clusiaceae) is composed of ca. 200 species, with a pantropical distribution. Some species are used as medicinal agents to treat a large number of diseases, including gastric ulcers, infections, pain, tumors, and inflammatory processes, among others. A review of the literature regarding the chemical and biological aspects of these plants indicates cytotoxic activity against several cell lines, inhibition of HIV-1 reverse transcriptase, antisecretory and cytoprotective properties, antinociceptive, molluscicidal and antimicrobial effects, etc., related particularly to the presence of coumarins, xanthones, flavonoids, and triterpenes. This review, therefore, deals with the chemistry, and pharmacology or biology of the main plants belonging to the genus Calophyllum, with particular emphasis on C. brasiliense, studied by our research group.

Aleurites moluccanus and its main active constituent, the flavonoid 2″-O-rhamnosylswertisin, in experimental model of rheumatoid arthritis.

ETHNOPHARMMACOLOGICAL RELEVANCE: Aleurites moluccana is used in folk medicine to treat pain, fever, asthma, hepatitis, gastric ulcer and inflammatory process in general, and the nut oil had been topically applied to treat arthritis and other joint pain, however the seeds are classified as toxic for oral use. AIM: Faced with the need for new alternative to treat the symptoms and modify rheumatoid arthritis (RA) the aim of this work was to evaluate the effects of A. moluccanus' leaves dried extract in rats and mice submitted to complete Freund adjuvant (CFA)-induced RA. MATERIAL AND METHODS: Wistar Rats and Swiss mice were submitted to CFA-induced RA in the right hindpaw. They received A. moluccanus extract (orally; p.o.), dexamethasone (subcutaneously), 2″-O-rhamnosylswertisin (p.o.) or vehicle (p.o.), from the 14th day after the CFA injection for up to 8 days. The mechanical hypersensitivity was evaluated using the von Frey filaments and the paw-oedema was measured using a plethysmometer. The rats' injected hindpaw was used to perform the histological analysis. RESULTS: A. moluccanus was able to significantly reduce the mechanical hypersensitivity in both ipsi- and contralateral hindpaws of mice injected with CFA, in a dose dependent manner. Furthermore, the paw-oedema was progressively reduced by A. moluccanus. Similar results were obtained for the positive-control drug dexamethasone and the isolated compound 2″-O-rhamnosylswertisin. Besides the effects mentioned above, the extract was also effective to repair the joint damage in CFA-induced RA rats, including reduction of fibrosis, cartilage degradation and bone erosion scores. CONCLUSION: These results together with the literature data reinforce the anti-hypersensitivity and anti-inflammatory activity of A. moluccanus extract. Part of the observed effects is due to the presence of the compound 2″-O-rhamnosylswertisin. The fact that the extract acted as a disease modifier point this herbal product as a promisor and safe tool to treat RA and other associated chronic diseases.

Effects of Eugenia umbelliflora O. Berg (Myrtaceae)-leaf extract on inflammation and hypersensitivity.

ETHNOPHARMACOLOGICAL RELEVANCE: The leaves of Eugenia species are widely used in popular medicine to treat several diseases, such as arthritis, rheumatism and diabetes. Eugenia umbelliflora O. Berg is popularly known in Brazil as "baguaçu", name also conferred to Eugenia jambolana probably due to their apparent similarity. Although the popular use scientifically proved of E. jambolana as anti-diabetes and also as anti-inflammatory, there are only two scientific studies demonstrating anti-ulcer and bactericide activities of E. umbelliflora leaves extract, without reference to its possible anti-inflammatory activity. AIM OF THE STUDY: The aim of this study was to show the anti-oxidant and anti-inflammatory activity of the methanol extract obtained from E. umbelliflora leaves (EuL) using in vitro and in vivo protocols. MATERIALS AND METHODS: The total phenolic content was evaluated using the folin-Ciocalteu colorimetric method and phloroglucinols content by HPLC. The anti-oxidant activity was evaluated by ORAC, ABTS•+, DPPH, and metal chelation methods. The anti-inflammatory activity was investigated using carrageenan-induced inflammation in the subcutaneous tissue of male Swiss mice orally pre-treated with the EuL (0.3, 1 or 3 mg/kg). The leukocyte influx (optical microscopy) and secretion of chemical mediators (TNF, IL-6, IL-1ß and CXCL1, by enzyme-linked immunosorbent assay) were quantified in the inflamed exudate. Histological analysis of the pouches was also performed. The anti-hypersensitive activity was investigated using carrageenan-induced mechanical hypersensitivity and mice were then evaluated using the von Frey filaments. The Open Field test was used to evaluate possible interference of adverse effect of EuL on locomotor activity that could lead to misinterpretation of the hypersensitivity evaluation. RESULTS: The EuL demonstrated important and moderate reducing capacity on ABTS•+ and DPPH assays, respectively, but with slight activity in ORAC test. It reflects low protection against cell damage. The EuL also presented 30% of phenolic compounds. The phloroglucinols content of EuL was 25.9 mg/g, 18.4 mg/g and 16.6 mg/g of eugenial C, eugenial D and eugenial E, respectively. The in vivo analysis of the inflammatory exudate of EuL-treated mice demonstrated reduction in the polymorphonuclear cells (PMN) migration to the inflamed tissue, as well as the reduction of the pro-inflammatory cytokine IL-1ß. Histologically, it was observed evident decrease in the oedema, formed essentially by non-haemorrhagic fibrin exudate, as well as PMN infiltrate, when compared with control mice injected with carrageenan. Furthermore, the extract also presented effective reduction of the mechanical hypersensitivity induced by carrageenan without any interference in animal's locomotor and exploratory activity. CONCLUSIONS: Together, the results herein obtained show that EuL presented anti-inflammatory activity by decreasing the influx of PMN to the inflamed tissue, as well as the cytokine IL-1ß level. This anti-inflammatory activity was also accompanied by significant anti-hypersensitive effect. The effects presented by EuL seem not to be correlated with an antioxidant activity. However other extract chemical compounds could be responsible for its important anti-inflammatory effects.

The hydroethanolic Litchi chinensis leaf extract alleviate hepatic injury induced by carbon tetrachloride (CCl4) through inhibition of hepatic inflammation.

Various medicinal plants are traditionally used in a hepatoprotective manner, like, for example, the Litchi chinensis leaf infusion that is employed in Chinese medicine as liver tonics to strengthen hepatic functioning. In this context, the present study was designed to evaluate the hepatoprotective and acute toxicological effects of hydroethanolic L. chinensis leaf extract in HepG2 cells and mice. Specifically, the cytotoxicity and hepatoprotective activities of L. chinensis leaf extract were evaluated in HepG2 cells and in vivo against carbon tetrachloride (CCl4)-induced acute liver injury. The administration of CCl4 in mice provokes cell swelling, loss of sinusoid capillary spaces and structural disarrangement of the hepatic lobe, apoptosis and leukocyte infiltration. Further, CCl4 evokes an increase in serum alanine aminotransferase (ALT), tumor necrosis factor (TNF) and interleukin-6 (IL-6) levels in hepatic tissue. However, Silymarin, the positive control, and the L. chinensis extract were able to restore the viability of cells treated with CCl4 at all concentrations evaluated, reduced the inflammatory parameters, TNF and IL-6, reestablished hepatic tissue morphology and did not induce acute toxicological alterations. The data obtained underscore that the extract from L. chinensis leaves features hepatoprotective activity, corroborating with ethnopharmacological use, and does not lead to acute toxicological effects.

Taraxerol as a possible therapeutic agent on memory impairments and Alzheimer's disease: Effects against scopolamine and streptozotocin-induced cognitive dysfunctions.

Alzheimer's disease (AD) is a neurodegenerative disorder associated with cognitive impairment and cholinergic neuronal death, characteristic of the effect of time on biochemical neuronal function. The use of medicinal plants as an alternative form of prevention, or even as a possible treatment of AD, is therefore interesting areas of research, since the standard drugs have many side effects. Taraxerol (TRX) is a triterpene that has been isolated from several plant species, and its various pharmacological properties have already been identified, such the acetylcholinesterase (AChE) inhibition activity in vitro. There is a lack of information in literature that confirms the effect of TRX in an animal AD-like model. Seeking to fill this gap in the literature, in the present work we assessed the effect of TRX on AChE activity in the animals' encephalon and hippocampus. We also investigated the effect of TRX (1.77 µM/side, 0.5 µL) isolated from leaves of Eugenia umbelliflora Berg. on aversive memory impairments induced by scopolamine (2 µg/side, 0.5 µL) infused into rat hippocampus, and the effect of TRX (0.89 and 1.77 µM/side, 0.5 µL) on aversive memory impairments induced by streptozotocin (STZ) (2.5 mg/mL, 2.0 µL) infused i.c.v. into mice, using the step-down inhibitory avoidance task. We found that TRX significantly inhibited AChE activity in the animal's hippocampus. Furthermore, TRX significantly improved scopolamine and STZ-induced memory impairment. Taking together, these results confirms its AChE activity inhibition in animals and indicate that TRX has anti-amnesic activity that may hold significant therapeutic value in alleviating certain memory impairments observed in AD.

Photochemoprotective effects against UVA and UVB irradiation and photosafety assessment of Litchi chinensis leaves extract.

Actually, there has been an increase in the use of natural products as skin photoprotective agents. In this way, the aim of present study was to investigate the L. chinensis leaves extract photochemoprotection potential and photosafety using in vitro methods. The extract cytotoxicity, cytoprotection and photochemoprotection against UVA and UVB radiation were assayed in L929 cells. The DNA damage was evaluated by comet assay. DCFH-DA, SOD, CAT and GSH assays were employed to verify the oxidative stress. We also determined the spectrophotometric Solar Protection Factor (SPF) of the extract. The photosafety was evaluated in red blood cells (RBC). In addition, the HET-CAM and agarose overlay tests were employed to evaluate the irritant potential. The results obtained show that extract is not cytotoxic and present cytoprotective activity against H2O2 and is able to protect the cells against DNA damage induced by UVA and UVB radiation. The extract was able to reduce the ROS production. The SPF obtained was 18.9 at 1mg/mL. We demonstrate that L. chinensis extract is photosafe and protect RBCs against oxidative damage, and did not induce irritation. Data herein obtained pointed out the potential of L. chinensis extract for photochemoprotection against UVA/UVB radiation and its damaging effects on human skin.

Hydroalcoholic extract of Sapium glandulatum (Vell.) Pax displays potent anti-inflammatory activities through a glucocorticoid receptor-dependent pathway.

BACKGROUND: Ethnobotanical studies of the Sapium genus reveal that many species are widely used in several countries as therapeutic drugs and they are widely used in folk medicine for treatment of different diseases, including skin inflammation. This raises interest in the study of the pharmacological properties and phytochemical composition of these plants. The biological properties of Sapium glandulatum, a native species of southern Brazil, has not been reported in the literature. PURPOSE: The aim of the present study was to investigate the anti-inflammatory action of the hydroalcoholic extract of Sapium glandulatum (EHSG) leaves in mouse models of acute or chronic skin inflammation. STUDY DESIGN/METHODS: Topical effects of EHSG were evaluated in 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced edema in the ear. Systemic effects of the extract were studied in a TPA-induced ear edema model, as well as in a carrageenan-induced paw edema model. To gain insight into the mechanism by which EHSG blocked inflammation, we evaluated the role of glucocorticoid receptors (GR) using the TPA-induced ear edema model and also measured specific binding in a glucocorticoid assay. Possible adverse effects of EHSG were evaluated after multiple treatments with the extract in the skin atrophy model on the ear and with the alkaline comet assay. RESULTS: EHSG presented potent anti-inflammatory activity when applied topically in acute and chronic models, inhibiting edema formation and leukocyte migration as well as expression pro-inflammatory cytokines IL-1ß, IL-6 and TNF-α in the tissue. Similar anti-inflammatory effects were found following oral treatment in both ear and paw edema models. Strikingly, the EHSG-induced blockade of leukocyte migration was reversed by mifepristone, a GR antagonist. Additionally, a specific binding assay revealed that ESGH interacts with GR. Multiple treatments with EHSG failed to induce adverse effects when evaluated in the skin atrophy model and bone marrow genotoxicity test. CONCLUSION: Taken together, our data suggest that EHSG is a potential source of anti-inflammatory tool compounds for the treatment of pro-inflammatory-derived skin diseases, and its mechanism of action may be, at least in part, via the GR pathway.

Antinociceptive action of the extract and the flavonoid quercitrin isolated from Bauhinia microstachya leaves.

This study examined the antinociceptive effect of Bauhinia microstachya (Leguminosae), a native plant widely distributed in the South of Brazil, in several chemical and mechanical models of pain. The methanolic extract (ME) from B. microstachya (3--30 mg kg(-1), i.p.) and the isolated compound quercitrin (1--10 mg kg(-1), i.p.), given 30 min earlier, produced a dose-dependent inhibition of acetic-acid-induced visceral pain in mice, with a mean ID50 value (dose necessary to reduce the nociceptive response by 50% relative to the control value) of 7.9 and 2.4 mg kg(-1), respectively. The ME of B. microstachya (3--100 mg kg(-1), i.p., 30 min earlier) also caused a dose-dependent inhibition of capsaicin-induced pain, with a mean ID50 value of 18.8 mg kg(-1). Moreover, the ME (3--100 mg kg(-1), i.p., 30 min earlier) produced marked inhibition of both phases of formalin-induced pain, with mean ID50 values for the neurogenic and the inflammatory phases of 30.3 and 17.2 mg kg(-1), respectively. In addition, the ME of B. microstachya (3--300 mg kg(-1), i.p., 30 min earlier) inhibited, in a graded manner, the hyperalgesia induced by bradykinin (3.2 microg/paw), substance P (13.5 microg/paw), carrageenan (300 microg/paw), capsaicin (100 microg/paw) and adrenaline (100 ng/paw) in the rat paw, with mean ID50 values of 20.5, 17.9, 101.8, 54.2 and 99.7 mg kg(-1), respectively. Taken together, these data demonstrate that ME of B. microstachya elicited a pronounced antinociceptive action against several chemical and mechanical models of pain in mice and rats. The precise mechanism responsible for the antinociceptive effect of the extract still remains unclear, but seems to be partly related to modulation of the release or action of pro-inflammatory mediators involved in the models of pain used. Finally, the flavonoid quercitrin isolated from this plant appears to contribute for the antinociceptive property of the methanolic extract.

Macrocarpal-like Compounds from Eugenia umbelliflora Fruits and Their Antibacterial Activity.

Certain members of the genus Eugenia are used as foods. One of these species is Eugenia umbelliflora, which is used for its fruits. The aim of the study was to isolate the constituents of the CH2Cl2 fraction obtained from E. umbelliflora O. Berg (Myrtaceae) and also to evaluate its antimicrobial properties. Two new meroterpenoids, eugenial C (3) and eugenial D (4) were isolated from the unripe fruits of E. umbelliflora and their structures established mainly by extensive NMR spectroscopy. In previous studies, the CH2Cl2 extract showed significant antibacterial activity, which can be attributed to meroterpenoids isolated in this study. The compounds eugenials C and D exhibited potent activity against Bacillus subtilis and Staphylococcus aureus and different strains of MRSA and activity similar to those of the antibiotics used in antimicrobial therapies.

Separation of flavonoids from Aleurites moluccana leaves using chitosan modified with heptaldehyde.

Heptaldehyde-modified chitosan (heptyl-chitosan, CH-Hp) was investigated as adsorbent for chromatograhic separation of the flavonoids from A. moluccana. The amount of 2"-O-rhamnosylswertisin isolated (30.0 mg) was approx. twice as high as swertisin (17.5 mg). The improved surface hydrophobicity effected by the heptyl groups promoted the separation of flavonoids. From the results obtained, CH-Hp seems to be more suitable for separation of glycosylated flavonoids than other flavonoids. Thus, modified chitosan described here can be used for hydrophobic interaction chromatography as sucessfully illustrated with flavonoids.

Separation of C-glycoside flavonoids from Aleurites moluccana using chitin and full N-acetylated chitin.

This paper describes a comparative study using different chromatographic supports (fully N-acetylated chitin, chitin and silica gel) to separate the flavonoids swertisin and 2"-O-rhamnosylswertisin from Aleurites moluccana. The results show that the flavonoids have apparently been separated by the hydrogen bond between the stationary phase (chitin and chitin-100) and flavonoids under the conditions studied.

Contribution of α,ß-Amyrenone to the Anti-Inflammatory and Antihypersensitivity Effects of Aleurites moluccana (L.) Willd.

The aim of the study was to analyze the constituents of the dichloromethane fraction obtained from A. moluccana and also to evaluate the anti-inflammatory and antinociceptive properties of α,ß-amyrenone isolated from A. moluccana in mice. The dichloromethane fraction was evaluated by gas chromatography and submitted to purification. The mixture of α,ß-amyrenone was isolated and then evaluated using the carrageenan-induced paw-oedema or pleurisy and CFA-induced arthritis models in mice. Five triterpenes, α,ß-amyrenone, glutinol, and α,ß-amyrin were isolated from dichloromethane fraction of A. moluccana leaf extract. The mixture of α,ß-amyrenone, dosed orally, was able to reduce mechanical hypersensitivity and paw-oedema induced by carrageenan, interfering with neutrophil migration. Similar results were observed in the carrageenan-induced pleurisy model. Repeated administration of the compounds was also effective in reducing the mechanical sensitization and oedema developed in the arthritis model induced by CFA. In conclusion, the results demonstrate that α,ß-amyrenone interferes in both acute and chronic inflammatory processes. We can infer that these effects involve, at least in part, a reduction in the neutrophil migration. Therefore, it seems reasonable to suggest that α,ß-amyrenone could represent a new therapeutic tool for the management of painful and inflammatory diseases, especially those presenting a chronic profile.

Chemical composition, antioxidant and antinociceptive properties of Litchi chinensis leaves.

OBJECTIVES: Litchi chinensis has been traditionally used in folk medicine to treat several ailments. In this study, we investigated the chemical composition, antioxidant and antinociceptive activity of L. chinensis leaves. METHODS: The antioxidant capacity of the extract, fraction and compounds was evaluated using the 1,1-diphenyl-picrylhydrazyl (DPPH) and 2,2'-azinobis (3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) assays, and the liposome model with peroxyl radicals generated by 2,2'-azobis (2-amidinopropane) dihydrochloride radical. The pharmacological models of acute nociception used in mice were: writhing test with acetic acid (AA), hotplate (HP), glutamate (GLU), capsaicin (CP) and formalin (FM) tests. KEY FINDINGS: The main compounds isolated were procyanidin A2 (PA2), procyanidin B2 (PB2) and (-)-epicatechin. The biochemical features of the crude extracts and their ethyl acetate fraction (EtOAcFR) presented high antioxidant activity, and the antioxidant activity of PA2 and PB2 was remarkably high, with DPPH and ABTS. The crude methanol extract (MeOHEXTR), EtOAcFR and PB2 were effective in reducing nociception in FM and HP models. MeOHEXTR and EtOAcFR treatments also reduced pain induced by GLU and AA. In the CP model, only EtOAcFR and PB2 were effective. CONCLUSIONS: The results demonstrate the antinociceptive and antioxidant of MeOHEXTR, EtOAcFR and PB2.

Euglobal-like compounds from the genus Eugenia.

Two regioisomeric meroterpenoids, Eugenial A and B, have been isolated from the fruits of Eugenia multiflora and their structures established on the basis of NMR evidences. They possess a phloroglucinol-monoterpene structure similar to the euglobals occurring in the sister genus Eucaliptus. A simple method to distinguish between regioisomeric pairs was pointed.