Biological activities of marine invertebrates extracts from the northeast brazilian coast / Atividades biológicas de extratos de invertebrados marinhos da costa nordeste do Brasil

Abstract This paper reports the in vitro antiproliferative effects, antiprotozoal, anti-herpes and antimicrobial activities of 32 organic extracts of 14 marine sponges and 14 corals collected in northeast Brazilian coast. The ethanolic extracts of the sponges Amphimedon compressa and Tedania ignis, and the acetone extract of Dysidea sp. showed relevant results concerning the antiproliferative effects against A549, HCT-8, and PC-3 cell lines by sulforhodamine B assay, but also low specificity. Concerning the antiprotozoal screening, the ethanolic extract of Amphimedon compressa and the acetone and ethanolic extracts of Dysidea sp. were the most active against Leishmania amazonensis and Trypanosoma cruzi expressing β-galactosidase in THP-1 cells. In the preliminary anti-HSV-1 (KOS strain) screening, the ethanolic extracts of the sponges Amphimedon compressa, Haliclona sp. and Chondrosia collectrix inhibited viral replication by more than 50%. The most promising anti-herpes results were observed for the ethanolic extract of Haliclona sp. showing high selective indices against HSV-1, KOS and 29R strains (SI> 50 and >79, respectively), and HSV-2, 333 strain (IS>108). The results of the antibacterial screening indicated that only the ethanolic extract of Amphimedon compressa exhibited a weak activity against Enterococcus faecalis, Pseudomonas aeruginosa and Escherichia coli by the disk diffusion method. In view of these results, the extracts of Amphimedon compressa, Tedania ignis and Dysidea sp. were selected for further studies aiming the isolation and identification of the bioactive compounds with antiproliferative and/or antiprotozoal activities. The relevant anti-herpes activity of the ethanolic extract of Haliclona sp. also deserves special attention, and will be further investigated.

Resumo Este artigo reporta as atividades in vitro antiproliferativa, atiprotozoárica, anti-herpética e antimicrobiana de 32 extratos orgânicos provenientes de 14 esponjas marinhas e 14 corais coletados no litoral nordestino brasileiro. Os extratos etanólicos das esponjas Amphimedon compressa e Tedania ignis, e o extrato acetônico de Dysidea sp. demonstraram resultados promissores em relação aos efeitos antiproliferativos frente as linhagens celulares A549, HCT-8, PC-3 pelo método da sulforrodamina B, mas sem especificidade. Em relação à atividade antiprotozárica, os extratos etanólico de Amphimedon compressa e acetônico e etanólico de Dysidea sp. apresentaram atividade contra Leishmania amazonensis e Trypanosoma cruzi através do método de expressão de β-galactosidase em células THP-1. Na investigação preliminar de atividade antiviral frente ao vírus Herpes simplex tipo 1 (cepa KOS), os extratos etanólicos das esponjas Amphimedon compressa, Haliclona sp. e Chondrosia collectrix inibiram mais de 50% da replicação viral. O extrato etanólico da esponja Haliclona sp. demonstrou resultados promissores para atividade anti-herpética com altos índices de seletividade para as cepas KOS (IS >50) e 29R (IS>79) frente ao VHS-1 e cepa 333 (IS>108) frente ao VHS-2. O extrato etanólico da esponja Amphimedon compressa exibiu uma pequena atividade contra Enterococcus faecalis, Pseudomonas aeruginosa and Escherichia coli pelo método de difusão em disco. De acordo com os resultados apresentados, os extratos das esponjas Amphimedon compressa, Tedania ignis e Dysidea sp. serão selecionados para futuros estudos de isolamento e identificação dos compostos bioativos para as atividades antiproliferativa e antiprozoárica. O extrato etanólico de Haliclona sp. será investigado por possuir atividade relevante anti-herpética.

Biological activities of marine invertebrates extracts from the northeast brazilian coast.

This paper reports the in vitro antiproliferative effects, antiprotozoal, anti-herpes and antimicrobial activities of 32 organic extracts of 14 marine sponges and 14 corals collected in northeast Brazilian coast. The ethanolic extracts of the sponges Amphimedon compressa and Tedania ignis, and the acetone extract of Dysidea sp. showed relevant results concerning the antiproliferative effects against A549, HCT-8, and PC-3 cell lines by sulforhodamine B assay, but also low specificity. Concerning the antiprotozoal screening, the ethanolic extract of Amphimedon compressa and the acetone and ethanolic extracts of Dysidea sp. were the most active against Leishmania amazonensis and Trypanosoma cruzi expressing ß-galactosidase in THP-1 cells. In the preliminary anti-HSV-1 (KOS strain) screening, the ethanolic extracts of the sponges Amphimedon compressa, Haliclona sp. and Chondrosia collectrix inhibited viral replication by more than 50%. The most promising anti-herpes results were observed for the ethanolic extract of Haliclona sp. showing high selective indices against HSV-1, KOS and 29R strains (SI> 50 and >79, respectively), and HSV-2, 333 strain (IS>108). The results of the antibacterial screening indicated that only the ethanolic extract of Amphimedon compressa exhibited a weak activity against Enterococcus faecalis, Pseudomonas aeruginosa and Escherichia coli by the disk diffusion method. In view of these results, the extracts of Amphimedon compressa, Tedania ignis and Dysidea sp. were selected for further studies aiming the isolation and identification of the bioactive compounds with antiproliferative and/or antiprotozoal activities. The relevant anti-herpes activity of the ethanolic extract of Haliclona sp. also deserves special attention, and will be further investigated.

Biological activities of marine invertebrates extracts from the northeast brazilian coast

Abstract This paper reports the in vitro antiproliferative effects, antiprotozoal, anti-herpes and antimicrobial activities of 32 organic extracts of 14 marine sponges and 14 corals collected in northeast Brazilian coast. The ethanolic extracts of the sponges Amphimedon compressa and Tedania ignis, and the acetone extract of Dysidea sp. showed relevant results concerning the antiproliferative effects against A549, HCT-8, and PC-3 cell lines by sulforhodamine B assay, but also low specificity. Concerning the antiprotozoal screening, the ethanolic extract of Amphimedon compressa and the acetone and ethanolic extracts of Dysidea sp. were the most active against Leishmania amazonensis and Trypanosoma cruzi expressing -galactosidase in THP-1 cells. In the preliminary anti-HSV-1 (KOS strain) screening, the ethanolic extracts of the sponges Amphimedon compressa, Haliclona sp. and Chondrosia collectrix inhibited viral replication by more than 50%. The most promising anti-herpes results were observed for the ethanolic extract of Haliclona sp. showing high selective indices against HSV-1, KOS and 29R strains (SI> 50 and >79, respectively), and HSV-2, 333 strain (IS>108). The results of the antibacterial screening indicated that only the ethanolic extract of Amphimedon compressa exhibited a weak activity against Enterococcus faecalis, Pseudomonas aeruginosa and Escherichia coli by the disk diffusion method. In view of these results, the extracts of Amphimedon compressa, Tedania ignis and Dysidea sp. were selected for further studies aiming the isolation and identification of the bioactive compounds with antiproliferative and/or antiprotozoal activities. The relevant anti-herpes activity of the ethanolic extract of Haliclona sp. also deserves special attention, and will be further investigated.

Resumo Este artigo reporta as atividades in vitro antiproliferativa, atiprotozoárica, anti-herpética e antimicrobiana de 32 extratos orgânicos provenientes de 14 esponjas marinhas e 14 corais coletados no litoral nordestino brasileiro. Os extratos etanólicos das esponjas Amphimedon compressa e Tedania ignis, e o extrato acetônico de Dysidea sp. demonstraram resultados promissores em relação aos efeitos antiproliferativos frente as linhagens celulares A549, HCT-8, PC-3 pelo método da sulforrodamina B, mas sem especificidade. Em relação à atividade antiprotozárica, os extratos etanólico de Amphimedon compressa e acetônico e etanólico de Dysidea sp. apresentaram atividade contra Leishmania amazonensis e Trypanosoma cruzi através do método de expressão de -galactosidase em células THP-1. Na investigação preliminar de atividade antiviral frente ao vírus Herpes simplex tipo 1 (cepa KOS), os extratos etanólicos das esponjas Amphimedon compressa, Haliclona sp. e Chondrosia collectrix inibiram mais de 50% da replicação viral. O extrato etanólico da esponja Haliclona sp. demonstrou resultados promissores para atividade anti-herpética com altos índices de seletividade para as cepas KOS (IS >50) e 29R (IS>79) frente ao VHS-1 e cepa 333 (IS>108) frente ao VHS-2. O extrato etanólico da esponja Amphimedon compressa exibiu uma pequena atividade contra Enterococcus faecalis, Pseudomonas aeruginosa and Escherichia coli pelo método de difusão em disco. De acordo com os resultados apresentados, os extratos das esponjas Amphimedon compressa, Tedania ignis e Dysidea sp. serão selecionados para futuros estudos de isolamento e identificação dos compostos bioativos para as atividades antiproliferativa e antiprozoárica. O extrato etanólico de Haliclona sp. será investigado por possuir atividade relevante anti-herpética.

Anxiolytic-like, stimulant and neuroprotective effects of Ilex paraguariensis extracts in mice.

Yerba-mate (Ilex paraguariensis St. Hil.) is the most used beverage in Latin America with approximately 426 thousand of tons consumed per year. Considering the broad use of this plant, we aimed to investigate the anxiety-like and stimulant activity of both the hydroethanolic (HE) and aqueous (AE) extracts from leaves of I. paraguariensis. Swiss mice were treated with I. paraguariensis HE or AE chronically or acutely, respectively, followed by evaluation in the elevated plus-maze (EPM; anxiety-like paradigm), open field (OF; locomotor activity) or the step-down avoidance task (memory assessment). Following behavioral protocols the brains were collected for evaluation of acetylcholinesterase (AChE) activity ex vivo. Chronic treatment with HE induced an anxiolytic-like effect and increased motor activity besides augmented AChE activity. Additionally, acute treatment with AE prevented the scopolamine-induced memory deficit in the step-down avoidance task. Overall, our results indicate the importance of the I. paraguariensis-induced CNS effects, since it is a widely used nutraceutical. We have reported anxiolytic, stimulant and neuroprotective effects for this plant species. These effects are potentially modulated by the cholinergic system as well as by caffeine.

Glycosylflavonoids from Cecropia pachystachya Trécul are quorum sensing inhibitors.

The Cecropia genus is widely distributed in Latin America including at least 60 species, and some of them are commonly used in traditional medicine for the treatment of several diseases. We used Cecropia pachystachya Trécul to search for quorum sensing (QS) inhibitors compounds and found that the aqueous extract of C. pachystachya leaves is a promising source of substances with this activity. Using as biosensor Chromobacterium violaceum ATCC 31532 and Escherichia coli pSB403, the compounds chlorogenic acid (2), isoorientin (3), orientin (4), isovitexin (6), vitexin (7), and rutin (9) were identified as QS inhibitors. None of these compounds inhibited the growth of neither the used biosensors nor the microorganisms Staphylococcus aureus ATCC 23591, Escherichia coli ATCC 25922 and Saccharomyces cerevisiae, used here as growth inhibition controls. Along with the rutin, here we presented for the first time the QS-inhibition potential of the C-glycosyl flavonoids. The prospective of this evidence lead to the use of these compounds as antipathogenic drugs or antifoulants.

In vitro antiherpes effects of a C-glycosylflavonoid-enriched fraction of Cecropia glaziovii Sneth.

AIMS: To investigate the in vitro antiherpes effects of the crude aqueous extract obtained from Cecropia glaziovii leaves and their related fractions, the n-butanol fraction (n-BuOH) and the C-glycosylflavonoid-enriched fraction (MeOH(AMB)), and to determine the viral multiplication step(s) upon which this C-glycosylflavonoid-enriched fraction acts. METHODS AND RESULTS: The antiviral activity was evaluated against human herpes virus types 1 and 2 (HHV-1, HHV-2) by plaque reduction assay. The mode of action of the most active fraction was investigated by a set of assays, and the results demonstrated that MeOH(AMB) fraction exerts anti-herpes action by the reduction of viral infectivity (only against HHV-2); by the inhibition of virus entry into cells; by the inhibition of cell-to-cell virus spread as well as by the impaired levels of envelope proteins of HHV-1. The high-performance liquid chromatography (HPLC)-photo-diode array (PDA) analysis showed that the C-glycosylflavonoids are the major constituents of this fraction. CONCLUSIONS: These data showed that the MeOH(AMB) fraction has an antiviral activity against HHV types 1 and 2. The C-glycosylflavonoids are the major constituents of this fraction, which suggests that they could be one of the compounds responsible for the detected anti-herpes activity. SIGNIFICANCE AND IMPACT OF THE STUDY: The MeOH(AMB) fraction can be regarded as a phytopharmaceutical candidate for the treatment of herpetic infections.

Passiflora alata and Passiflora edulis spray-dried aqueous extracts inhibit inflammation in mouse model of pleurisy.

The aqueous leaves extracts of Passiflora alata (100-300 mg/kg, i.p.) and Passiflora edulis (100-1000 mg/kg, i.p.) possess a significant antiinflammatory activity on carrageenan-induced pleurisy in mice. Treatment with the extracts inhibited leukocyte migration and reduced the formation of exudate. Moreover, a significant inhibition of myeloperoxidase and adenosine-deaminase activities was observed at the doses tested (100 or 250 mg/kg, i.p.). At the same doses, a significant decrease of serum C-reactive protein was observed.

Comparação das metodologias da Farmacopéia Brasileira para determinação de água em matérias-primas vegetais, e validação da determinação de água em analisador de umidade para Calendula officinalis L., Foeniculum vulgare Miller, Maytenus ilicifolia Mart. ex. Reissek e Passiflora alata Curtis / Comparison of pharmacopeial methods for water determination in plant raw materials and validation of water determination by infrared drying for Calendula officinalis, Foeniculum vulgare, Maytenus ilicifolia e Passiflora alata

No presente trabalho foi descrita a comparação da aplicabilidade das metodologias preconizadas na Farmacopéia Brasileira (1988) para a determinação de água em drogas vegetais. Foi realizada, ainda, a validação da determinação de água em analisador de umidade. As matérias-primas vegetais analisadas foram Calendula officinalis L. (calêndula), Foeniculum vulgare Miller (funcho), Maytenus ilicifolia Mart. ex. Reissek (espinheira-santa) e Passiflora alata Curtis (maracujá). A análise dos resultados obtidos mostrou que há diferenças estatisticamente significativas (p < 0,05) entre as metodologias "Determinação de água por destilação azeotrópica" e "Determinação de água em drogas vegetais" em estufa, assim como, entre a "Determinação da perda por dessecação" para as drogas vegetais calêndula e funcho. No entanto, não foram observadas diferenças estatisticamente significativas (p < 0,05) entre as duas metodologias de secagem em estufa. Quanto à validação da determinação de água em analisador de umidade, não foram observadas diferenças estatisticamente significativas (p<0,05) entre os resultados das análises em analisador de umidade e os obtidos através da "Determinação da perda por dessecação". Além disso, não foram verificadas diferenças estatisticamente significativas (p < 0,05) para as análises referentes à repetibilidade, precisão intermediária e reprodutibilidade da técnica, o que comprova a exatidão e a precisão da metodologia proposta.

A comparison of the Brazilian pharmacopeial methodologies for water determination in plant raw materials is presented for the following species: Calendula officinalis, Foeniculum vulgare, Maytenus ilicifolia e Passiflora alata. In addition, the validation of water determination by infrared drying was carried out for these species. The results obtained using the azeotropic distillation method (Brazilian Pharmacopoeia - "Determination of Water by Azeotropic Distillation") were significantly different (p<0.05) than those obtained using two different gravimetric methods (Brazilian Pharmacopoeia - "Determination of Water in Vegetable Drugs" and "Determination of loss on Drying"). However, no significant statistical difference was observed between the two gravimetric methodologies. After optimization of operating conditions, the results of water determination by infrared drying were not significantly different than those obtained using the loss on drying pharmaceutical method. Also, no statistically significant differences were observed for repeatability, intermediate precision and reproducibility of the method, demonstrating the accuracy and precision of the proposed methodology.

Constituents from leaves of Quillaja brasiliensis.

A new abietane diterpene, the 19-O-beta-D-glucopyranoside of 16-hydroxylambertic acid was isolated from the leaves of Quillaja brasiliensis together with a known prosapogenin (3-O-beta-D-glucuronopyranosyl-quillaic acid), quercetin, and rutin. The new compound was identified by chemical and spectroscopic methods.

Triterpenes and saponins from Ilex psammophila.

Two new saponins were isolated from the leaves of Ilex psammophila. Their structure was established by chemical and spectroscopic methods as 28-O-beta-D-glucopyranosylester of 20(S)-ilexgenin A ([structure: see text]) and 28-O-beta-D-glucopyranosylester of 20(S)-3beta,19alpha,24-trihydroxyurs-12-ene-23, 28-dioic acid ([structure: see text]).

Análise das bulas de medicamentos fitoterápicos comercializados em Porto Alegre, RS, Brasil / Analysis of phytomedicines package inserts commercialized in Porto Alegre, RS, Brazil

Com o objetivo de avaliar a qualidade das bulas de medicamentos fitoterápicos em relação à presença das frases obrigatórias por lei, bem como de informações específicas exigidas pela legislação de medicamentos fitoterápicos, foram selecionados 65 produtos em farmácias de Porto Alegre contendo pelo menos uma das seguintes plantas medicinais: maracujá, boldo, alcachofra, guaraná e sene. Através de um formulário, analisou-se a presença das frases exigidas pela Portaria 110/97 da ANVS, que regulamenta as bulas de medicamentos, e das informações exigidas pela Resolução RDC 17/00 da ANVS, sobre registro de medicamentos fitoterápicos. A maioria dos produtos analisados não possui bula, e em nenhum deles verificou-se a presença de todas a frases e demais informações exigidas pela legislação vigente. Especialmente significante foi a inexistência de dados sobre reações adversas, contra-indicações e advertências. Foi possível concluir que as bulas de medicamentos fitoterápicos analisados não seguem as normas legais, são incompletas e deficientes de informações, podendo induzir a sérios problemas de saúde.

Sixty-five products with one of the following medicinal plants: passion flower, boldus, artichoke, guarana and senne were acquired in drugstores of Porto Alegre, RS, Brazil. These products were analyzed in order to evaluate the quality of phytomedicines package inserts in relation to the obligatory informations required by the Brazilian drug legislation. Most of the products did not have package inserts, and none of them presented all informations required by the legislation. Furthermore, most of them omitted the potential occurrence of adverse effects, contra-indications and precautions. In conclusion, the analyzed package inserts did not followed the Brazilian drug regulation, were incomplete and showed deficiencies which can induce health consumer problems.

Plantas usadas como medicinais no município de Ipê, RS, Brasil / Medicinal plants used by people from Ipê, Rio Grande do Sul State, Brazil

Foi realizado um levantamento das plantas medicinais utilizadas pela população do município de Ipê, RS, Brasil, visando uma investigação da medicina tradicional, melhoramento e racionalização das práticas medicinais populares, em um projeto envolvendo voluntários da comunidade. Foram entrevistadas 114 pessoas, que mencionaram 252 plantas, das quais foram identificadas 105 espécies, agrupadas em 48 famílias. As plantas coletadas e identificadas foram analisadas, de acordo com dados químicos, farmacológicos e/ou toxicológicos encontrados na literatura científica. Os resultados obtidos mostram que a população deste município faz uso de plantas que, ainda, não foram alvo de pesquisa química, farmacológica e/ou toxicológica e, também, que a mesma faz uso de onze espécies, que são reconhecidamente, responsáveis por efeitos colaterais indesejados, ou ainda, que são tóxicas.

Medicinal plants used by Brazilian people from Ipê city, in Rio Grande do Sul State, were the subject of a survey realized in order to investigate the traditional medicine in this comunity. The project involved 114 individuals who cited 252 medicinal plants. From these plants, 105 species were identified and classified into 48 botanical families. Assessments of all known plants were based on chemical, pharmacological and toxicological data searched in scientific literature. The results show that many of these plants were not yet chemically and/or pharmacologically and/or toxicologically studied, and eleven of them were related to be responsible for side effects or even toxicity in the consulted scientific literature.

[Drug use by pregnant women in six Brazilian cities]. / Uso de medicamentos por gestantes em seis cidades brasileiras.

OBJECTIVE: To describe drugs used during pregnancy by women attending prenatal clinics of the national public health system (SUS) in Brazilian cities. METHODS: Using a structured questionnaire, 5,564 pregnant women between the week 21 to 28 who attended prenatal visits of the SUS in six Brazilian cities were interviewed. The interview questions were grouped in "guided use" to cover pain, cramps, nausea, cough, and others, and "guided medicine" to cover vitamins, iron, and fluoride. The Food and Drug Administration gestational risk classification (1991-1995) was applied. RESULTS: Of a total of 5,564 women, 4,614 (83.8%) used at least one drug during pregnancy, with a total of 9,556 drugs used. The drugs most frequently used were vitamins associated with anti-anemics (33.5%), gastrointestinal drugs (31.3%), analgesics and anti-inflammatory drugs (22.2%), anti-anemics (19.8%), and antibiotics (11.1%). Regarding gestational risk, 3,243 drugs used (34%) belonged to category A risk, 1,923 (22.6%) to category B, 3,798 (39.7%) to category C, 289 (3.0%) to category D, and 55 (0.6%) to category X. CONCLUSIONS: A large variation in drug use across the cities was observed, especially for anti-anemics and vitamins associated with anti-anemics, revealing the lack of a national consensus regarding the use of these drugs during pregnancy. There was no literature data about safety during pregnancy for 12.9% of the drugs used. This percentage, plus the 26.9% of category C drugs, shows that 40% of the drugs used during pregnancy do not belong to the approved safety categories. However, only 3% of the 9,956 drugs used were clearly contraindicated during pregnancy.

Experimentally induced cholangiohepatopathy by dosing sheep with fractionated extracts from Brachiaria decumbens.

Cholangiohepatopathy was induced in 5 lambs by oral administration of extracts from signal grass (Brachiaria decumbens) in Brazil. Grossly there were pale foci multifocally distributed throughout the hepatic parenchyma in 4 lambs. The microscopic changes, which were similar to those produced by other steroidal sapogenins-containing plants such as Tribulus terrestris and Panicum spp., included multifocal cholangitis, bile duct proliferation, and the presence of crystals in the biliary system.

Comparative pharmacological study of hydroethanol extracts of Passiflora alata and Passiflora edulis leaves.

Several species of the genus Passiflora, known in Brazil as "maracujá", have widespread use in folk medicine as sedatives and tranquillizers. The anxiolytic activity of hydroethanol extracts of P. alata and P. edulis leaves was evaluated using the elevated plus-maze test. The extracts presented anxiolytic activity in dosages around 50, 100 and 150 mg/kg.

Tilirosídeo em Croton gnaphalii BAlLL

O gênero Croton possui seiscentas espécies e é originário de regiões tropicais. Croton gnaphelil é conhecida no sul do Brasil como infalivina, sendo utilizada popularmente nos distúrbios hepáticos. A substância majoritária presente nas partes aéreas desta planta foi isolada e identificada através de métodos espectroscópicos, sendo identificada como um glicosídeo acilado, o canferol‑3‑O‑(6"‑O‑p‑cumaroil)‑β‑D‑glicopyranose, também chamado de tilirosídeo.

Croton genus comprises six hundred species being native in tropical forests. Croton gnaphalliis popularly known as "infalivina" in South of Brazil and it is traditionally used for hepatic disorders. The major compound from aerial parts of this plant was isolated and its structure elucidated through spectroscopic analysis. It was identified as an acylglycoside, kaempferol‑3‑O‑(6"‑O‑p‑coumaroyl)‑ β ‑D‑glucopyranoside, known as tiliroside.

Antiinflammatory activity of extracts and fractions from the leaves of Gochnatia polymorpha.

The aqueous and ethanol extracts from the leaves of Gochnatia polymorpha and further fractions obtained from the latter extract using solvents with increasing polarity, including its aqueous residue and the amino acid, 4-hydroxy-N-methyl-proline were investigated by carrageenin-induced pedal oedema formation. It was shown that the aqueous and ethanol extracts and the ethyl acetate fraction demonstrated significant antiinflammatory activity. The chemical investigation of the latter fraction revealed the presence of caffeic acid, chlorogenic acid, 3-0-methylquercetin, hyperosid and rutin. The amino acid 4-hydroxy-N-methyl-proline, a nonprotein amino acid that has not been reported before in the Asteraceae was isolated as a major compound and identified by spectroscopic methods.

Effect of flavonol derivatives on the carrageenin-induced paw edema in the rat and inhibition of cyclooxygenase-1 and 5-lipoxygenase in vitro.

Alkoxyflavonols were synthesized by the Algar-Flynn-Oyamada (AFO) cyclization of chalcones. Hydroxyflavonols were prepared by dealkylation of methoxyflavonols by refluxing in hydroiodic acid. The alkoxyflavonols 3-hydroxy-2-(2,3,4-trimethoxyphenyl)-4H-chromen-4-one (6), 2-(4-ethoxyphenyl)-3-hydroxy-4H-chromen-4-one (7), 2-(4-butoxyphenyl)-3-hydroxy-4H-chromen-4-one (10), and 2-(3-n-butoxyphenyl)-3-hydroxy-4H-chromen-4-one (11) as well as the trihydroxy derivative 3-hydroxy-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one (18) displayed high anti-inflammatory activity in carrageenin-induced rat paw edema. Additionally, the inhibition of enzymes of the arachidonic acid cascade by the derivatives was investigated in vitro. In contrast to the natural compound quercetin, the compounds were more potent inhibiting cyclooxygenase-1 than 5-lipoxygenase except for 3-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one (5). No correlation between the anti-inflammatory activity in the rat paw edema test and the inhibition of 5-lipoxygenase or cyclooxygenase-1 could be observed. In conclusion, the present results suggest that other effects than inhibition of these enzymes of the arachidonic acid cascade are important for the anti-inflammatory activity of the investigated alkoxyflavonols.