A new isoflavone glucoside and other compounds from Poiretia bahiana C. Mueller: Chemophenetics, fragmentation pattern and biogenetic implications.

The genus Poiretia belongs to the Fabaceae (Leguminosae) family and it encompasses twelve species of flowering plants. The chemistry of this genus is scarcely investigated, although some studies have demonstrated the potential of Poiretia species to produce important bioactive compounds. Herein, we describe the phytochemical investigation of P. bahiana C. Mueller leaves. A new isoflavone glucoside named as 2',4',5'-trimethoxyisoflavone-7-O-ß-D-glucopyranoside (1), along with six known isoflavones (2-7), two rotenones (8-9), cyclitol 3-O-methyl-chiro-inositol (10), the amino acid proline (11), a mixture of sitosterol (12) and stigmasterol (13), and a mixture of the triterpenes lupeol (14) and ß-amirine (15) were obtained from P. bahiana leaves. The structures were established by extensive analysis of their spectroscopic data, which included 1H NMR, 13C NMR, DEPT, and 2D-NMR (13C1H HETCOR and 13C1H COLOC). Two isoflavones (3 and 5) and two rotenones (8-9) exhibited antifungal activity against the plant pathogenic fungus Cladosporium sphaerospermum. Furthermore, the biogenetic implications of the oxygenation pattern of the B-ring of the isoflavones, and the chemophenetics and fragmentation pattern of the isoflavones and rotenones are discussed.

Sensitivity of food spoilage fungi to a smoke generator sanitizer.

Smoke generator sanitizers are easy to handle and can access to hard-to-reach places. They are a promising alternative for controlling food and air borne fungi, which are known to cause losses in the bakery, meat, and dairy industries. Therefore, the present study aimed to evaluate the efficiency of a smoke generator sanitizer based on orthophenylphenol against ten fungal species relevant to food spoilage. The tests were carried out according to the norms by the French protocol NF-T-72281, with adaptations specific for disinfectants diffused in the air. The tests were performed in an enclosed room of approximately 32 m3. Aspergillus brasiliensis (ATCC 16404), Candida albicans (ATCC 10231), Aspergillus flavus (ATCC 9643), Aspergillus chevalieri (IMI 211382), Cladosporium cladosporioides (IMI 158517), Lichtheima corymbifera (CCT 4485), Mucor hiemalis (CCT 4561), Penicillium commune (CCT 7683), Penicillium polonicum (NGT 33/12), and Penicillium roqueforti (IMI 217568) were exposed to the smoke generator sanitizer for 7 h. The product was efficient against C. albicans and C. cladosporioides, although it was unable to reduce 4 log of the other tested species. The variable sensitivity of the fungal species to the sanitizer emphasizes the importance of confronting a target microorganism (causing problems in a specific food industry) with the sanitizer aiming to control it and obtain satisfactory results in hygiene programs.

Evaluation of disinfectants in order to eliminate fungal contamination in computer keyboards of an integrated health center in Piauí, Brazil.

This quantitative and qualitative study aimed to evaluate the level of fungal contamination in computer keyboards from an Integrated Health Center (IHC) at Piauí, Brazil, and to evaluate the efficacy of 50% sodium bicarbonate and 50% alcoholic vinegar solutions to eliminate these microorganisms. Ten keyboards from six sectors of the IHC were chosen randomly, and the collection was performed in three situations: (i) before of disinfection, (ii) after disinfection with solution of sodium bicarbonate, and (iii) after disinfection with solution of alcoholic vinegar. Samples were inoculated in Petri dishes with dextrose agar potato plus chloramphenicol and incubated at room temperature for 72 h. All keyboards were contaminated with opportunistic fungi, with Cladosporium cladosporioides (29.4%) being the most frequent species, followed by Curvularia lunata (17.6%) and Aspergillus niger, Alternaria alternata, and Curvularia clavata with 11.8% each. The two solutions were proven to be efficient in eliminating fungal contamination; however, the sodium bicarbonate solution caused esthetic damages in keyboards. In addition, this study is the first report of the antifungal activity of alcoholic vinegar in filamentous fungi. Based on our findings, we suggest a daily disinfection of keyboards with a 50% vinegar solution plus adequate hygiene from the hands of professionals before and after the use of the computer and its annexes, as key actions to reduce nosocomial infections, particularly in economically disadvantaged countries.

Chemical Composition and in vitro Biological Activities of Essential Oils from Conchocarpus fontanesianus (A. St.-Hil.) Kallunki & Pirani (Rutaceae).

This study aimed at assessing the chemical composition of the essential oils from leaves and fruits of Conchocarpus fontanesianus, an endemic Brazilian species of Rutaceae. The plant material was harvested from two regions of the Atlantic rainforest in the State of São Paulo. The volatile compounds in the essential oils were extracted by hydrodistillation (HD), and analyzed by GC/FID and GC/MS, allowing the quantification and identification of 54 components in total, which comprise about 97% of the total oil composition. From the leaves collected in Caraguatatuba and Juréia-Itatins, the major volatile compounds identified were as follows: spathulenol (22.32% and 16.67%) and α-cadinol (9.7% and 14.76%). However, ß-myrcene (34.56%), (+)-epi-bicyclosesquiphellandrene (8.71%), and bicyclogermacrene (5.80%) were dominant in the fruits collected only in Juréia-Itatins. The in vitro biological activities were tested to evaluate the cytotoxic, antifungal, and antioxidant potential of essential oils from leaves and fruits.

Phenylpropanoid-rich Essential Oils of Piper Species from the Amazon and their Antifungal and Anti-cholinesterase Activities.

The essential oils (EOs) from aerial parts of Piper aduncum, P. callosuin and P. marginatum, collected from the Amazon region of Brazil, were analyzed by GC-MS and then evaluated for their antifungal and anticholinesterase activities. The essential oils were dominated by phenylpropanoids, such as dillapiole (73.0%) in P. aduncum, safrole (66.0%) in P. callosum and 3,4-methylenedioxypropiophenone (21.8%) in P. inarginatum. The analyzed oils showed low to moderate antifungal activity; with detection limits (DL) from 10 to 100 pg against Cladosporium cladosporioides and C. sphareospermum. In the anticholinesterase (AChE) evaluation, the oils of P. callosum (DL = 0.01 ng) and P. marginatum (DL = 0.01 ng) were one hundred times more potent than the standard physostigmine (DL = 1.0 ng). Molecular docking analysis showed that phenylpropanoids docked reasonably well with acetyleholinesterase and may be responsible for the anti-AChE activities of the Piper EOs. This is the first presentation about acetylcholinesterase inhibition by methylenedioxyphenyl-propanoids.

Chemical composition and energetic values of wheat and its sub-products for broiler chicken / Composição química e valores energéticos do trigo e seus subprodutos para frangos de corte

The objective of this study was to determine the chemical composition, apparent metabolizable energy (AME), AME corrected by nitrogen retention (AMEn) and metabolization coefficients (MC and MCn) of different feeds for broilers from the western region of Paraná State. The experiment was conducted at the Physiology of Birds Laboratory at UNIOESTE. Two hundred and sixty male chicks of the Cobb 500 strain, at 21 days old, were distributed in a randomized design with 12 treatments and four replicates of five birds per experimental unit. The feed ingredients studied were ten different wheat middlings, one triticale, one wheat grain and a reference diet. Values for dry matter, nitrogen, gross energy, neutral detergent fiber, acid detergent fiber, mineral matter, calcium, phosphorus, sodium, potassium and magnesium composition were determined as well as the geometric mean diameter of the feed particles. To determine the apparent metabolizable energy (AME) and AME corrected for nitrogen balance (AMEn) the total excreta collection method was used with growing birds. The chemical composition of the feeds was variable. The values for AME and AMEn ranged from 1. 819-2. 958 and 1. 734-2. 882 kcal. kg-1, respectively. Based on these energetic values and the values for gross energy, the coefficients of metabolizability were calculated. The values ranged from 43. 26-75. 24% for MC and from 42. 28-73. 31% for MCn.(AU)

O objetivo deste trabalho foi determinar a composição química e os valores de energia metabolizável aparente (EMA), EMA corrigida pela retenção de nitrogênio (EMAn) e seus respectivos coeficientes de metabolizabilidade (CMA e CMAn) de diferentes alimentos para frangos de corte provenientes da região oeste do Estado do Paraná. O experimento foi realizado no Laboratório de Fisiologia de Aves da UNIOESTE. Foram utilizados 260 pintos de corte machos, da linhagem Cobb 500, com 21 dias de idade, distribuídos em um delineamento inteiramente casualizado, com doze tratamentos, quatro repetições e cinco aves por unidade experimental. Os ingredientes estudados foram dez diferentes farelos de trigo, um triticale, um trigo grão e uma ração referência. Foram determinados valores de matéria seca, nitrogênio, energia bruta, fibra em detergente neutro, fibra em detergente ácido, matéria mineral, cálcio, fósforo, sódio, potássio e magnésio e o valor do diâmetro geométrico médio. Para determinação dos valores de EMA e EMAn foi utilizado o método de coleta total de excretas com aves em crescimento. A composição química dos alimentos estudados apresentaram variações. Os valores de EMA e EMAn variaram de 1819 a 2958 e 1734 a 2882 kcal/kg, respectivamente. De acordo com os valores energéticos e energia bruta, foram calculados os coeficientes de metabolizabilidade, valores estes que variaram de 43,26 a 75,24% para CMA e de 42,28 a 73,31% para CMAn.(AU)

Composição química e atividade antifúngica do óleo essencial de poejo em diferentes estágios de desenvolvimento / Chemical composition and antifungal activity of pennyroyal essential oil in different stages of development

O objetivo deste estudo foi comparar o rendimento, a composição química e a atividade antifúngica do óleo essencial de Mentha pulegium (poejo) em diferentes estágios de desenvolvimento, cultivada sob condições controladas no sul do Brasil. A hidrodestilação de folhas frescas de M. pulegium, coletadas aos 60, 70 e 85 dias após o transplante, apresentou rendimento de óleo essencial de 0,17 %, 0,23 % e 0,17 %, respectivamente. Todas as amostras de óleo apresentaram atividade contra Cladosporium herbarum. Através das análises de cromatografia gasosa (GC) e GC/MS do óleo essencial, foram identificados onze constituintes, sete (mentona, isomentona, neoisomentol, pulegona, piperitona, 1.1- dimetoxi-2- nonino e piperitenona) comuns às três amostras, enquanto dois outros (mentofurano, mirtenal) foram detectados somente nas amostras da primeira e segunda coletas. A pulegona foi o principal constituinte nas duas primeiras amostras (26,65 %), seguida pela piperitenona (20,41; 12,60 %). A concentração de pulegona aumentou para 31,05 % na última coleta, porém o constituinte majoritário foi a piperitenona (36,32 %). Os resultados demonstraram que o óleo essencial de M. pulegium apresenta potencial como agente antifúngico e sua composição química depende do estágio de desenvolvimento da planta.(AU)

The aim of this study was to compare the yield, chemical composition and antifungal activity of the essential oil that is obtained from Mentha pulegium in different developmental stages and cultivated under controlled conditions in southern Brazil. The hydrodistillation of fresh leaves that were collected at 60, 70 and 85 days resulted inessential oil yields of 0.17 %, 0.23 % and 0.17 %, respectively. All of the essential oil samples showed antifungal activity against Cladosporium herbarum. The gas chromatograph (GC) and GC/MS analysis revealed eleven constituents: seven (pulegone, piperitenone, menthone, isomenthone, neoisomenthol, piperitone and 1.1-dimethoxy-2-nonyne) were common to three samples, while menthofuran and myrtenal were detected only in samples of the first and second stages. Pulegone was the main constituent of the essential oil samples from the first and second stages (26.65 %), followed by piperitenone (20.41; 12.60 %). The pulegone concentration increased to 31.05 % in the last collection, while the major constituent was piperitenone (36.32 %). In conclusion, the results demonstrated that M. pulegium essential oil presents potential as an antifungal agent, and its chemical composition depends on the stage of development during which it was extracted.(AU)

Antifungal potential of Avicennia schaueriana Stapf & Leech. (Acanthaceae) against Cladosporium and Colletotrichum species.

UNLABELLED: There is significant interest in research to develop plant extracts with fungicidal activities that are less harmful to the environment and human health than synthetic fungicides. This study aimed to evaluate the antifungal activity of the extracts of Avicennia schaueriana against Colletotrichum and Cladosporium species and to identify the compounds responsible for the activity. Leaves and stems of A. schaueriana were extracted with ethanol and partitioned with petroleum ether, chloroform and ethyl acetate. The antifungal activity of such extracts was tested by bioautography against Cladosporium sphaerospermum, Cladosporium cladosporioides and Colletotrichum lagenarium. Ethanolic extracts, petroleum ether and chloroform fractions of stems had the highest antifungal activity with several active bands (Rf = 0·72 and Rf = 0·55). In the agar dilution assay, ethanolic extract, petroleum ether and chloroform fractions of stems were the most efficacious, presenting 85, 62 and 63% growth inhibition of Colletotrichum gloeopsporioides and minimum inhibitory concentration values between 1 and 1·5 mg ml(-1) , respectively. Analysis carried out using gas chromatography coupled to a mass spectrometry of petroleum ether and chloroform fractions allowed the identification of fatty acids methyl esters, lupeol and naphthoquinones such as lapachol, α-lapachone, naphtho[2,3-b]furan-4,9-dione, 2-isopropyl- and avicenol-C. We may infer that the antifungal activity of A. schaueriana is due to the abundance of these compounds. SIGNIFICANCE AND IMPACT OF THE STUDY: This study shows that Avicennia schaueriana extracts have a high potential for the growth inhibition of Colletotrichum and Cladosporium ssp. and will provide a starting point for discovering new natural products with antifungal activity. Their development is of particular interest to organic production systems where synthetic fungicides cannot be used.

Composição química e atividade antifúngica do óleo essencial de poejo em diferentes estágios de desenvolvimento / Chemical composition and antifungal activity of pennyroyal essential oil in different stages of development

O objetivo deste estudo foi comparar o rendimento, a composição química e a atividade antifúngica do óleo essencial de Mentha pulegium (poejo) em diferentes estágios de desenvolvimento, cultivada sob condições controladas no sul do Brasil. A hidrodestilação de folhas frescas de M. pulegium, coletadas aos 60, 70 e 85 dias após o transplante, apresentou rendimento de óleo essencial de 0,17 %, 0,23 % e 0,17 %, respectivamente. Todas as amostras de óleo apresentaram atividade contra Cladosporium herbarum. Através das análises de cromatografia gasosa (GC) e GC/MS do óleo essencial, foram identificados onze constituintes, sete (mentona, isomentona, neoisomentol, pulegona, piperitona, 1.1- dimetoxi-2- nonino e piperitenona) comuns às três amostras, enquanto dois outros (mentofurano, mirtenal) foram detectados somente nas amostras da primeira e segunda coletas. A pulegona foi o principal constituinte nas duas primeiras amostras (26,65 %), seguida pela piperitenona (20,41; 12,60 %). A concentração de pulegona aumentou para 31,05 % na última coleta, porém o constituinte majoritário foi a piperitenona (36,32 %). Os resultados demonstraram que o óleo essencial de M. pulegium apresenta potencial como agente antifúngico e sua composição química depende do estágio de desenvolvimento da planta.

The aim of this study was to compare the yield, chemical composition and antifungal activity of the essential oil that is obtained from Mentha pulegium in different developmental stages and cultivated under controlled conditions in southern Brazil. The hydrodistillation of fresh leaves that were collected at 60, 70 and 85 days resulted inessential oil yields of 0.17 %, 0.23 % and 0.17 %, respectively. All of the essential oil samples showed antifungal activity against Cladosporium herbarum. The gas chromatograph (GC) and GC/MS analysis revealed eleven constituents: seven (pulegone, piperitenone, menthone, isomenthone, neoisomenthol, piperitone and 1.1-dimethoxy-2-nonyne) were common to three samples, while menthofuran and myrtenal were detected only in samples of the first and second stages. Pulegone was the main constituent of the essential oil samples from the first and second stages (26.65 %), followed by piperitenone (20.41; 12.60 %). The pulegone concentration increased to 31.05 % in the last collection, while the major constituent was piperitenone (36.32 %). In conclusion, the results demonstrated that M. pulegium essential oil presents potential as an antifungal agent, and its chemical composition depends on the stage of development during which it was extracted.

Chemical composition and energetic values of wheat and its sub-products for broiler chicken / Composição química e valores energéticos do trigo e seus subprodutos para frangos de corte

The objective of this study was to determine the chemical composition, apparent metabolizable energy (AME), AME corrected by nitrogen retention (AMEn) and metabolization coefficients (MC and MCn) of different feeds for broilers from the western region of Paraná State. The experiment was conducted at the Physiology of Birds Laboratory at UNIOESTE. Two hundred and sixty male chicks of the Cobb 500 strain, at 21 days old, were distributed in a randomized design with 12 treatments and four replicates of five birds per experimental unit. The feed ingredients studied were ten different wheat middlings, one triticale, one wheat grain and a reference diet. Values for dry matter, nitrogen, gross energy, neutral detergent fiber, acid detergent fiber, mineral matter, calcium, phosphorus, sodium, potassium and magnesium composition were determined as well as the geometric mean diameter of the feed particles. To determine the apparent metabolizable energy (AME) and AME corrected for nitrogen balance (AMEn) the total excreta collection method was used with growing birds. The chemical composition of the feeds was variable. The values for AME and AMEn ranged from 1. 819-2. 958 and 1. 734-2. 882 kcal. kg-1, respectively. Based on these energetic values and the values for gross energy, the coefficients of metabolizability were calculated. The values ranged from 43. 26-75. 24% for MC and from 42. 28-73. 31% for MCn.

O objetivo deste trabalho foi determinar a composição química e os valores de energia metabolizável aparente (EMA), EMA corrigida pela retenção de nitrogênio (EMAn) e seus respectivos coeficientes de metabolizabilidade (CMA e CMAn) de diferentes alimentos para frangos de corte provenientes da região oeste do Estado do Paraná. O experimento foi realizado no Laboratório de Fisiologia de Aves da UNIOESTE. Foram utilizados 260 pintos de corte machos, da linhagem Cobb 500, com 21 dias de idade, distribuídos em um delineamento inteiramente casualizado, com doze tratamentos, quatro repetições e cinco aves por unidade experimental. Os ingredientes estudados foram dez diferentes farelos de trigo, um triticale, um trigo grão e uma ração referência. Foram determinados valores de matéria seca, nitrogênio, energia bruta, fibra em detergente neutro, fibra em detergente ácido, matéria mineral, cálcio, fósforo, sódio, potássio e magnésio e o valor do diâmetro geométrico médio. Para determinação dos valores de EMA e EMAn foi utilizado o método de coleta total de excretas com aves em crescimento. A composição química dos alimentos estudados apresentaram variações. Os valores de EMA e EMAn variaram de 1819 a 2958 e 1734 a 2882 kcal/kg, respectivamente. De acordo com os valores energéticos e energia bruta, foram calculados os coeficientes de metabolizabilidade, valores estes que variaram de 43,26 a 75,24% para CMA e de 42,28 a 73,31% para CMAn.

Antifungal compounds produced by Colletotrichum gloeosporioides, an endophytic fungus from Michelia champaca.

In this study, eight endophytic fungi were isolated from the leaves, stems and roots of Michelia champaca. The isolates were screened and evaluated for their antifungal, anticancer and acetylcholinesterase (AChE) inhibitory activities. All of the extracts exhibited potent activity against two evaluated phytopathogenic fungi. Chemical investigation of EtOAc extracts of the endophytic fungus Colletotrichum gloeosporioides resulted in the isolation of one new compound, 2-phenylethyl 1H-indol-3-yl-acetate (1), and seven known compounds: uracil (2), cyclo-(S*-Pro-S*-Tyr) (3), cyclo-(S*-Pro-S*-Val) (4), 2(2-aminophenyl)acetic acid (5), 2(4-hydroxyphenyl)acetic acid (6), 4-hydroxy- benzamide (7) and 2(2-hydroxyphenyl)acetic acid (8). All of the compound structures were elucidated using 1D and 2D NMR and MS analyses. The antifungal and AChE inhibitory activities of compounds 1-8 were evaluated in vitro. Compound 1 exhibited promising activity against Cladosporium cladosporioides and C. sphaerospermum that was comparable to that of the positive control nystatin.

Antifungal and cytotoxic 2-acylcyclohexane-1,3-diones from Peperomia alata and P. trineura.

Bioactivity-guided fractionation of the separate CH2Cl2 extracts from the aerial parts of Peperomia alata and P. trineura yielded seven polyketides: alatanone A [3-hydroxy-2-(5'-phenylpent-4'E-enoyl)cyclohex-2-en-1-one, 1a] and alatanone B [3-hydroxy-2-(3'-phenyl-6'-methylenedioxypropanoyl)cyclohex-2-en-1-one, 2a] from P. alata and trineurone A [3-hydroxy-2-(11'-phenylundec-10'E-enoyl)cyclohex-2-en-1-one, 1b], trineurone B [3-hydroxy-2-(15'-phenyl-18'-methylenedioxypentadecanoyl)cyclohex-2-en-1-one, 2b], trineurone C [3-hydroxy-2-(17'-phenyl-20'-methylenedioxyheptadecanoyl)cyclohex-2-en-1-one, 2c], trineurone D [3-hydroxy-2-(hexadec-10'Z-enoyl)cyclohex-2-en-1-one, 3a], and trineurone E [(6R)-(+)-3,6-dihydroxy-2-(hexadec-10'Z-enoyl)cyclohex-2-en-1-one, 3b] from P. trineura. The isolated compounds were evaluated for antifungal activity against Cladosporium cladosporioides and C. sphaeospermum and for cytotoxicity against the K562 and Nalm-6 leukemia cell lines.

Structural studies and investigation on the activity of imidazole-derived thiosemicarbazones and hydrazones against crop-related fungi.

New imidazole derived thiosemicarbazones and hydrazones were prepared by condensation of 4(5)-imidazole carboxaldehyde, 4-(1H-imidazole-1-yl)benzaldehyde and 4-(1H-imidazole-1-yl)acetophenone with a thiosemicarbazide or hydrazide. All compounds were characterized by quantitative elemental analysis, IR and NMR techniques. Eight structures were determined by single crystal X-ray diffraction. The antifungal activities of the compounds were evaluated. None of the compounds exhibited significant activity against Aspergillus flavus and Candida albicans, while 4(5)-imidazolecarboxaldehyde thiosemicarbazone (ImT) and 4-(1H-imidazole-1-yl)benzaldehyde thiosemicabazone (4ImBzT) were highly and selectively active against Cladosporium cladosporioides. 4(5)-Imidazolecarboxaldehyde benzoyl hydrazone (4(5)ImPh), 4(5)-imidazolecarboxaldehyde-para-chlorobenzoyl hydrazone (4(5)ImpClPh), 4(5)-imidazolecarboxaldehyde-para-nitrobenzoyl hydrazone (4(5)ImpNO2Ph), 4-(imidazole-1-yl)acetophenone-para-chloro-benzoyl hydrazone (4ImAcpClPh) and 4-(imidazole-1-yl)acetophenone-para-nitro-benzoylhydrazone (4ImAcpNO2Ph) were highly active against Candida glabrata. 4(5)ImpClPh and 4(5)ImpNO2Ph were very effective against C. cladosporioides. In many cases, activity was superior to that of the reference compound nystatin.

Isolation, identification and antimicrobial activity of propolis-associated fungi.

Propolis is a natural product widely known for its medicinal properties. In this work, fungi present on propolis samples were isolated, identified and tested for the production of antimicrobial metabolites. Twenty-two fungal isolates were obtained, some of which were identified as Alternaria alternata, Aspergillus flavus, Bipolaris hawaiiensis, Fusarium merismoides, Lasiodiplodia theobromae, Penicillium citrinum, Penicillium crustosum, Penicillium janthinellum, Penicillium purpurogenum, Pestalotiopsis palustris, Tetracoccosporium paxianum and Trichoderma koningii. These fungi were grown in liquid media to obtain crude extracts that were evaluated for their antibiotic activity against pathogenic bacteria, yeast and Cladosporium cladosporioides and A. flavus. The most active extract was obtained from L. theobromae (minimum inhibitory concentration = 64 µg/mL against Listeria monocitogenes). Some extracts showed to be more active than the positive control in the inhibition of Staphylococcus aureus and L. monocitogenes. Therefore, propolis is a promising source of fungi, which produces active agents against relevant food poisoning bacteria and crop-associated fungi.

Antifungal activity of tetrahydroquinolines against some phytopathogenic fungi.

Seven synthetic tetrahydroquinolines with different substitution patterns were obtained by an imino Diels-Alder condensation reaction and were evaluated against phytopathogenic fungi. Compounds with a methoxy group showed interesting activity against Cladosporium cladosporoides with a MIC value of 13.75 microg/mL

A new minor dimmeric ester from seeds of Cassia fistula L. (Leguminosae).

Bioactivity-guided fractionation of n-hexane phase from MeOH extract of the seeds of Cassia fistula L. (Leguminosae) yielded two bioactive substances against Cladosporium cladosporioides and C. sphaerospermum. After spectroscopic analysis, these compounds were characterised as the known benzyl 2-hydroxy-3,6-dimethoxybenzoate and its dimer dibenzyl 2,2'-dihydroxy-3,6,3″,6″-tetramethoxy-biphenyl-1,1'-dicarboxylate, which showed a new structural arrangement.

Chemical profile and biological potential of non-polar fractions from Centroceras clavulatum (C. Agardh) Montagne (Ceramiales, Rhodophyta).

The present study reports the Gas Chromatography-Mass Spectrometry (GC-MS) evaluation of the hexanes and dichloromethane fractions from extracts of the red alga Centroceras clavulatum (C. Agardh) Montagne. Twenty three compounds were identified, totaling ca. 42% of both fractions (0.18 g mass extract). The main constituents of the fractions were hexadecanoic acid (17.6%) and pentadecanoic acid (15.9%). Several secondary metabolites with interesting biological activity, such as (-)-loliolide, neophytadiene, phytol were identified. In addition, several classes of secondary metabolites, including phenolic compounds (e.g., phenylacetic acid), terpene derivatives, fatty acids, halogenated compound (e.g., 2-chlorocyclohexenol), lignoids, steroids, esters, amides (e.g., hexadecanamide), ketones, carboxylic acids, aldehydes and alcohols were observed. The occurrence of several of these structural classes is described for the first time in this species. The same fractions analyzed by GC-MS, and a separate set of polar fractions, were evaluated against two life cycle stages (epimastigote and trypomastigote forms) of the protozoan Trypanosoma cruzi and against phytopatogenic fungi Cladosporium cladosporiodes and C. sphaerospermum. The dichloromethane fraction was active against both T. cruzi forms (epimastigote IC(50) = 19.1 µg.mL-1 and trypomastigote IC(50) = 76.2 µg.mL-1). The hexanes and ethyl acetate fractions also displayed activity against both fungi species (200 µg) by TLC-bioautography.

Anti-inflammatory, antioxidant and antifungal activity of Chuquiraga spinosa.

CONTEXT: Stem and leaves infusion of Chuquiraga spinosa (R&P) Don. (Asteraceae) is used in the Peruvian traditional medicine for its anti-inflammatory properties and for the treatment of vaginal infections. OBJECTIVE: This study evaluated the antioxidant, anti-inflammatory and antifungal activities of C. spinosa for the first time. MATERIALS AND METHODS: Extracts of methanol, 50% methanol and water were obtained from C. spinosa aerial parts. Antioxidant activity of the extracts was evaluated (DPPH˙, ABTS˙(+) and superoxide radical-scavenging activity). The correlation between these results and total polyphenolic content was determined by Pearson's Correlation Coefficient. Anti-inflammatory activity of 50% methanol extract was evaluated with the rat model of carrageenan-induced acute inflammation and mouse model of TPA-induced acute inflammation. The antifungal activity of the extracts against Cladosporium cucumerinum and Candida albicans was studied by direct bioautography, and antifungal activity against phytopathogenic fungi was performed by culture in potato dextrose agar plates. RESULTS: All the extracts showed high antioxidant activity, and there was correlation between the activity and total polyphenolic compounds. As 50% methanol extract was administered orally, the paw edema in rats was reduced significantly (52.5%). This extract, by topical administration, produced a reduction of 88.07% of the edema TPA-induced in ear of mice. The aqueous and 50% methanol extracts were active against C. albicans (minimum inhibitory concentration of 2.5 and 6.25 µg, respectively). The aqueous extract showed antifungal activity against C. cucumerinum (MIC: 2.5 µg). DISCUSSION AND CONCLUSION: Preliminary phytochemical screening and the analysis of the three extracts by high-performance liquid chromatography diode-array detection showed the majority compounds are flavonoids and phenolic acid derivatives. These compounds may be responsible of the radical-scavenging activity of these extracts as well as responsible of anti-inflammatory effect in vivo of 50% methanol extract. Several authors have demonstrated the antioxidant and anti-inflammatory properties of some flavonoids and phenolic acids. The antifungal activity of the extracts obtained from aerial parts of C. spinosa has been investigated here for the first time. Other studies are necessary to determine the mechanism of action and to identify the bioactive compounds of this plant.

Patagonicosides B and C, two antifungal sulfated triterpene glycosides from the sea cucumber Psolus patagonicus.

Two new triterpene glycosides, patagonicosides B and C (2 and 3, resp.), together with the known patagonicoside A (1), have been isolated from the EtOH extract of the sea cucumber Psolus patagonicus. The structures of the new compounds were established on the basis of extensive NMR spectroscopic analysis ((1)H- and (13)C-NMR, (1)H,(1)H-COSY, HMBC, HSQC, TOCSY, and NOESY), HR-ESI-MS data, and chemical transformations. Compounds 1-3 and their desulfated analogs showed antifungal activities against the phytopathogenic fungus Cladosporium cladosporoides in a dose-dependent fashion.

Isoswertisin flavones and other constituents from Peperomia obtusifolia.

A phytochemical investigation of the leaves and stems of Peperomia obtusifolia (Piperaceae) yielded a new flavone C-diglycoside isoswertisin-4'-methyl-ether-2''α-L-rhamnoside (1), along with four known compounds: isoswertisin-2''α-L-rhamnoside (2), (+)-diayangambin (3), 2-episesalatin (4) and corchoionoside C (5). The structures of the two flavone C-diglycosides (1, 2) were elucidated on the basis of 1D and 2D NMR spectroscopy and MS spectrometric data. These flavones were evaluated by bioautographic assay against Cladosporium cladosporioides and C. sphaerospermum and showed weak antifungal activity.