Special metabolites isolated from Urochloa humidicola (Poaceae)

ABSTRACT This study aims to identify special metabolites in polar extracts from Urochloa humidicola (synonym Brachiaria humidicola) that have allelopathic effects and induce secondary photosensitization in ruminants. The compounds were isolated and identified via chromatographic and spectroscopic techniques. The compounds 4-hydroxy-3-methoxy-benzoic acid, trans-4-hydroxycinnamic acid, and p-hydroxy-benzoic acid; the flavonols isorhamnetin-3-O-β-d-glucopyranoside and methyl quercetin-3-O-β-d-glucuronate; and kaempferitrin, quercetin-3-O-α-l-rhamnopyranoside, and tricin were identified in the extract from the leaves of Urochloa humidicola. Two furostanic saponins, namely, dioscin and 3-O-α-l-rhamnopyranosyl-(1-4)-[α-l-rhamnopyranosyl-(1-2)]-β-d-glucopyranosyl-penogenin, as well as catechin-7-O-β-d-glucopyranoside were identified in the methanolic extract obtained from the roots of this plant. This species features a range of metabolites that may be toxic for animals if used in food and may interfere with the growth medium, thereby inhibiting the development of other species.

Lethal and sublethal effects of essential oil of Lippia sidoides (Verbenaceae) and monoterpenes on Chagas´ disease vector Rhodnius prolixus

The aim of this study was to identify the composition of the essential oil from leaves of Lippia sidoides (EOLS), a typical shrub commonly found in the dry northeast of Brazil, popularly known as “alecrim-pimenta”. Additionally, we investigated the nymphicidal, ovicidal, phagoinhibitory and excretion effects of EOLS, its major constituent thymol and its isomer carvacrol, on fourth instar nymphs and eggs of Rhodnius prolixus, the Chagas’ disease vector. The nymphicidal and ovicidal activity of thymol, carvacrol, and EOLS was assessed by tests using impregnated Petri dishes. The lethal concentration values (LC50) for EOLS, carvacrol, and thymol were 54.48, 32.98, and 9.38 mg/cm2, respectively. The ovicidal test showed that both carvacrol and thymol (50 mg/cm2) inhibited hatching (50% and 23.3%, respectively), while treatments with 10 mg/cm2 or 50 mg/cm2 EOLS did not affect the hatching rate at all (80% and 90%, respectively). We observed an anti-feeding effect in insects fed with blood containing natural products at the higher concentrations (100 µg/mL). Finally, excretion rate was affected by EOLS and carvacrol, but not by thymol. These findings offer novel insights into basic physiological processes that make the tested natural compounds interesting candidates for new types of insecticides.

Effects of Acmella oleracea methanolic extract and fractions on the tyrosinase enzyme

Abstract The aim of the current study is to evaluate the effect of Acmella oleracea (L.) R.K. Jansen, Asteraceae, methanolic extract, hexane (84.28% spilanthol) and dichloromethane (approximately 100% spilanthol) fractions on the tyrosinase enzyme. The dehydrated jambu extract was obtained through maceration using methanol. The extract residue was solubilized in MeOH/H2O (8:2) and subjected to liq.–liq. partition in organic solvents. Both the extraction and the partition procedures were conducted with three replicates. The analyses were performed using GC–MS, 1H and 13C NMR. The hexane fraction provided samples containing 84.28, 82.91 and 62.83% spilanthol in repetitions 1, 2 and 3, respectively. The dichloromethane fraction showed 88.55% spilanthol in repetition 1, and approximately 100% spilanthol in repetitions 2 and 3. The jambu extract as well as the hexane fraction (84.28% spilanthol) were able to activate the oxidizing activity of the tyrosinase enzyme for L-DOPA. The dichloromethane fraction (approximately 100% spilanthol) showed stronger inhibition effect on the tyrosinase enzyme in the first 10 min. The results raise the interest in study in spilanthol formulations for topical use, since it may prevent and/or slow skin hyperpigmentation or depigmentation processes. Furthermore, spilanthol may be used to control the enzymatic browning in fruits and vegetables.

Spilanthol: occurrence, extraction, chemistry and biological activities

Abstract Spilanthol (C14H23NO, 221.339 g/mol) is a bioactive compound that is found in many different plants that are used as traditional remedies throughout the world. It is present in Heliopsis longipes and several species in the genus Acmella, including A. oleracea L., also known as paracress and jambu. Its leaves and flowers have sensory properties (pungency, tingling, numbing, mouth-watering) that make it a popular spice and ingredient in several Brazilian dishes. Spilanthol can exert a variety of biological and pharmacological effects including analgesic, neuroprotective, antioxidant, antimutagenic, anti-cancer, anti-inflammatory, antimicrobial, antilarvicidal and insecticidal activities. So, the aim of this review is to present a literature review on the spilanthol that describes its occurrence, chemistry, extraction and biological activities.

Distribution of metabolites in galled and non-galled leaves of Clusia lanceolata and its antioxidant activity

Essential oils of galled and non-galled leaves of Clusia lanceolata Cambess., Clusiaceae, were obtained by hydrodistillation and analyzed by GC and GC/MS. The chemical composition of both oils was similar, with a predominance of sesquiterpene caryophyllenes. The extracts from the leaves were evaluated regarding total phenols, flavonoids and proanthocyanidins. Galled leaves showed higher levels of phenolics and proanthocyanidins, since the content of flavonoids was higher in non-galled leaves. The chromatographic profiles of extracts were obtained by using HPLC/DAD and LC-ESI-MS. Electrospray ionisation (ESI) in positive and negative ion mode was used to identify four flavones C-glycosides in both extracts. The study constitutes a first report on the chemical research of C. lanceolata. The extract from galled leaves had a higher antioxidant activity.

Bioactivity of the latex from Parahancornia amapa (Apocynaceae) on the development of Rhodnius nasutus (Hemiptera, Reduviidae, Triatominae) under laboratory conditions

Bioactivity of the latex from Parahancornia amapa (Apocynaceae) on the development of Rhodnius nasutus (Hemiptera, Reduviidae, Triatominae) under laboratory conditions. The aim of this study was to verify the effects of the methanolic fraction of the latex from Parahancornia amapa (Apocynaceae) (PALAM) on individuals of the species Rhodnius nasutus Stål (Hemiptera, Triatominae). Many of the insects treated with the substance presented deformities and these may interfere in the feeding and possibly hinder the reproductive capacity. They also presented significant mortality during the molt when compared to the control group, noting a gradual increase in mortality. The treated insects also presented delayed nymphal development (5th instar) and higher adult longevity.

Ouratea genus: chemical and pharmacological aspects

Ouratea and the other genera of the Ochnaceae family are a rich source of flavonoids and biflavonoids. These can be used as chemotaxonomic markers of Ouratea. Some biflavonoids, as well as extracts of the Ouratea species show important biological activities, such as antitumour, antiviral, vasodilation, antimicrobial and DNA topoisomerase inhibition. On the other hand species of this genus are used in folk medicine for gastric distress, dysentery, and diarrhea; as an astringent, a tonic, and for the treatment of inflammation-related diseases. The information collected in this review attempts to summarise the phytochemical and biological activities studied in Ouratea species that may be helpful to guide researches, to undertake further investigation concerning the common properties of Ouratea species and evaluation as a source of active compounds.

Efeito protetor da acetamida sobre as intoxicações experimentais em ratos por monofluoroacetato de sódio e por algumas plantas brasileiras que causam morte súbita / The protective effect of acetamide on experimental poisoning by sodium mono[1]luoroacetate and Brazilian sudden death causing plants in rats

O objetivo deste trabalho é avaliar e comparar o efeito protetor da acetamida nas intoxicações por monofluoroacetato de sódio (MF) e por oito plantas brasileiras que causam "morte súbita" (PBCMS) (Palicourea marcgravii, P. juruana, Pseudocalymma elegans, Arrabidaea bilabiata, Amorimia (Mascagnia) rigida, M. pubiflora, Amorimia (Mascagnia) exotropica e M. aff. rigida) em ratos, bem como descrever o quadro clínico-patológico nos animais intoxicados. Foram utilizados 33 ratos da linhagem Wistar (Rattus norvegicus albinus), nove dos quais ingeriram espontaneamente folhas frescas de P. marcgravii nas doses de 2,0 e 4,0g/kg. Dois desses ratos receberam doses únicas de acetamida de 2,0 e 4,0g/kg, por via oral um minuto antes do fornecimento da planta. Outro rato recebeu 4,0g/kg de acetamida após ingerir 4,0g/kg da planta e manifestar sintomas graves. Nos experimentos com MF, foram administradas a quatro ratos doses de 4,0 e 8,0mg/kg; o intervalo de tempo entre a administração da acetamida e dos extratos concentrados ou do MF variou entre 2 a 4 horas. A dose de acetamida utilizada variou de 2,0 a 8,0g/kg. Nos experimentos com extratos concentrados das oito PBCMS, 20 ratos foram intoxicados por via oral com doses únicas ou repetidas. A acetamida, quando previamente administrada em doses suficientemente altas, evitou o aparecimento dos sinais clínicos ou morte dos animais intoxicados por MF, bem como pelas folhas frescas de P. marcgravii e com os extratos concentrados de cada uma das sete outras PBCMS utilizadas. Todos esses ratos foram novamente submetidos ao mesmo protocolo experimental, porém sem administração de acetamida. Nesses experimentos posteriores todos os ratos manifestaram sinais clínicos e morte (exceto M. aff. rigida, cuja amostra não se revelou tóxica). Todos os ratos apresentaram aurículas de leve a acentuadamente ingurgitadas e, por vezes, também as veias cava cranial e caudal. Havia moderada dilatação cardíaca direita e esquerda em três animais. O fígado de todos os animais apresentava-se de leve a acentuadamente congesto, e em alguns ratos, verificou-se evidenciação do padrão lobular. Observou-se ainda discreta a leve presença de líquido espumoso na superfície de corte dos pulmões em três ratos. O exame histopatológico evidenciou nos rins de seis dos 30 ratos leve a moderada tumefação citoplasmática dos túbulos uriníferos contornados distais e, por vezes, também nos túbulos coletores, mas somente em quatro (dois intoxicados por P. marcgravii, um por P. elegans e outro por A. exotropica) havia a clássica lesão de degeneração hidrópico-vacuolar com picnose nuclear evidente. No fígado de 26 animais havia congestão e, destes, três apresentaram estreitamento compressivo dos cordões hepáticos, oito corpúsculos de choque; em outros três, necrose focal de discreta a moderada. Observou-se ainda, de discreta a moderada vacuolização de hepatócitos em 16 animais. Este trabalho demonstra que a acetamida possui acentuado efeito protetor, capaz de prevenir os sinais clínicos e evitar a morte dos ratos intoxicados por MF, folhas frescas de P. marcgravii e extratos concentrados de outras sete PBCMS. O quadro clínico-patológico observado nos ratos intoxicados pelo MF e pelas PBCMS deste estudo, associado ao efeito protetor da acetamida, confirma que o MF é o princípio tóxico responsável pela morte dos ratos, e, por extensão, também dos bovinos que ingeriram PBCMS.

The protective effect of acetamide in poisoning by sodium monofluoroacetate (MF) and by eight Brazilian sudden death causing plants (BSDCP) (Palicourea marcgravii, P. juruana, Pseudocalymma elegans, Arrabidaea bilabiata, Amorimia (Mascagnia) rigida, M. pubiflora, Amorimia (Mascagnia) exotropica and M. aff. rigida) was studied using rats. Additionally the clinical and pathological picture of the poisoning was described. In these experiments 33 Wistar rats (Rattus norvegicus albinus) were used. Nine rats ate spontaneously the fresh leaves of P. marcgravii at amounts of 2.0 and 4.0g/kg. Two of the rats received orally single doses of acetamide (2.0 and 4.0g/kg) one minute before the plant was supplied. A third rat received 4.0g/kg of acetamide after consumption of 4.0g/kg of the plant and showed severe symptoms of poisoning. In the experiments with MF, doses of 4.0 and 8.0mg/kg were administered to four rats. The interval between the administration of either acetamide and concentrated plant extracts or MF ranged from 2 to 4 hours; the dose of acetamide ranged from 2.0 to 8.0g/ kg. In the experiments with concentrated extracts of eight BSDCP, 20 rats were orally poisoned with single or repeated doses. Acetamide, when previously administered, prevented the appearance of clinical signs and death in all of the rats poisoned by MF, as well as of the ones poisoned by fresh P. marcgravii leaves and by the concentrated extracts of each of the other BSDCP. These rats were re-subjected to the same experimental protocol, yet without the administration of acetamide. In these experiments, all of the rats evidenced clinical signs and death (except M. aff. rigida). All of the rats showed mild to markedly engorged atria, and sometimes also of the cranial and caudal vena cava. In three of the rats, there was a moderate right and left cardiac dilatation. The liver of all rats was slightly or markedly congested, with lobular pattern in some. There was frothy liquid on the cut surface of the lungs in three of the rats. The histopathology of the kidneys in six rats showed slight cytoplasmic swelling of the distal convoluted tubules and sometimes also of the collecting tubules. But only in four rats a vacuolar-hydropic degeneration with nuclear pyknosis was seen. Twenty-six rats showed liver congestion, three of them with compressive narrowing of the hepatic cords, and in eight rats shock corpuscles were observed; another three rats showed slight to moderate focal liver necrosis. A slight to moderate vacuolation of hepatocytes was observed in 16 rats. It can be concluded that acetamide had a protective effect, capable to prevent clinical signs and death of the rats poisoned by MF, and by fresh P. marcgravii leaves and concentrated extracts of seven other BSDCP. The clinical and pathological picture observed in the rats poisoned by MF and BSDCP, associated with the protective effect of acetamide, indicate that MF is the toxic principle responsible for death of the rats, and by extension, for the death of cattle that ate BSDCP.

Chemical constituents from Piptadenia rigida Benth., Fabaceae, "angico"

The phytochemical investigation of the roots of Piptadenia rigida Benth., Fabaceae, known as "angico", afforded sitosterol, lupeol, betuline, the chalcone isoliquiritigenin, the flavonoids, 7,4'-dihydroxyflavone, 7,3',4'-trihydroxyflavone, 7,8,3',4'-tetrahydroxyflavanone, 4-hydroxy-3,5-dimethoxybenzaldehyde and methyl-3,4-dihydroxy-benzoate. Both flavones were also isolated from the branches of this plant. Five derivatives of the aldehyde were obtained by diazomethane treatment. The structures of compounds were identified by IR, NMR and mass spectral data analysis of natural compounds and some derivatives, and by comparison with literature data.

Chemical constituents of Piptadenia gonoacantha (Mart.) J.F. Macbr (pau jacaré)

The phytochemical investigation of Piptadenia gonoacantha (Mart.) J.F. Macbr. (Leguminosae-Mimosoideae), commonly known as "pau jacaré" (alligator stick), afforded sitosterol, campesterol, stigmasterol, the N-benzoylphenylalanine-2-benzoylamide-3-phenylpropyl ester, known as asperphenamate, sitosterol-3-O-β-D-glucopyranoside, besides three flavonoids, apigenin, 5-O-methylapigenin and 7,4'-dihydroxy-3',5-dimethoxyflavone from its branches. From its leaves, the methyl gallate and two flavonoids, vitexin and isovitexin, were isolated. From its bark, a mixture of sitosterol, campesterol, and stigmasterol, besides a mixture of cycloartenone, cycloartan-25-en-3-one, and 24-methylene-cycloartenone, and the pure triterpenes 24-methylenecycloartanol, friedelin, lupeol and lupenone, were isolated. Their structures were established on the basis of spectral analysis, comparison with literature data and GC-MS analysis of the mixtures. The ester, flavonoids and the cycloartanes are been identified for first time in the genus Piptadenia.

O estudo fitoquímico de galhos de Piptadenia gonoacantha (Mart.) J.F. Macbr. (Leguminosae-Mimosoideae), comumente conhecida como "pau jacaré", forneceu sitosterol, estigmasterol, o éster N-benzoilfenilalaninato de 2-N-benzoil-3-fenilpropila, conhecido como asperfenamato, 3-O-β-D-glicopiranosil-sitosterol, além de três flavonóides, apigenina (5,7,4'-triidroxiflavona), apigenina-5-O-metil éter e 7,4'-dihidroxi-3' , 5-dimetoxiflavona. Das folhas isolaram-se galato de metila e dois flavonóides, 8-C-glicopiranosil-5,7,4' -trihidroxiflavona e 6-C-glicopiranosil-5,7,4'-trihidroxiflavona, conhecidas como vitexina e isovitexina. Das cascas desta planta isolaram-se uma mistura de sitosterol, campesterol e estigmasterol; mistura de cicloartenona, cicloartan-25,26-en-3-ona e 24-metileno-cicloartanona, além dos triterpenos, 24-metilenocicloartenol, fridelina, lupeol e lupenona. As estruturas foram estabelecidas através de análise de espectros de IV, RMN ¹H e 13C e massas, além de análise com CG-EM para identificar os componentes das misturas de cicloartanos e esteróides. O éster conhecido como asperfenamato, os flavonóides e os cicloartanos estão sendo registrados pela primeira vez em Piptadenia.

Biflavones and triterpenoids isolated from Ouratea castaneifolia (DC.) Engl., Ochnaceae / Biflavonas e triterpenóides isolados de Ouratea castaneifolia (DC.) Engl., Ochnaceae

This paper presents the chemical investigation of the leaves and stems of Ouratea castaneifolia (DC.) Engl.. There are no chemical or pharmacological studies with this species. Classic phytochemical investigation of the organic extracts together with high pressure liquid chromatography (HPLC) procedures lead to the identification of seventeen metabolites: seven triterpenes (friedelin, 3β-friedelinol, α-amyrin, β-amyrin, lupeol, germanicol and taraxerol), four steroids (sitosterol, stigmasterol and the glycosides sitosteryl 3-O-β-D-glucopyranoside and stigmasteryl 3-O-β-D-glucopyranoside), one isoflavone (5,7,4'-trimethoxyisoflavone), one flavone (5,4'-dihydroxy-7,3',5'-trimethoxyflavone) and four biflavones (amenthoflavone, 7,7"-O-dimethylamenthoflavone, heveaflavone and tetramethylamenthoflavone). The structures of the compounds were established by the analysis of ¹H, 13C NMR spectra including bidimensional techniques. The classes of the identified metabolites are in agreement with previous studies of the Ouratea genus.

O presente trabalho trata da investigação química das folhas e caule da espécie Ouratea castaneifolia (DC.) Engl., sobre a qual não há registros de estudos químicos ou farmacológicos anteriores. O estudo fitoquímico clássico dos extratos orgânicos do caule e das folhas de O. castaneifolia foi aliado à técnica da cromatografia líquida de alta eficiência (CLAE) e resultou na identificação de dezessete metabólitos: sete triperpenos (friedelina, 3β-friedelinol, α-amirina, β-amirina, lupeol, taraxerol e germanicol), quatro esteróides (sitosterol, estigmasterol e os glucosídeos sitosteril 3-O-β-D-glicopiranosídeo e estigmasteril 3-O-β-D-glicopiranosídeo), uma isoflavona (5,7,4´-trimetoxiisoflavona), uma flavona (5,4´-diidroxi-7,3´,5´-trimetoxiflavona), quatro biflavonas (amentoflavona, 7,7"-O-dimetil-amentoflavona, heveaflavona e tetrametilamentoflavona). A identificação das substâncias foi feita com base na análise de espectros de RMN de ¹H, 13C e técnicas bidimensionais. As classes dos metabólitos identificados estão de acordo com aquelas citadas em estudos químicos do gênero Ouratea.

New iodine derivatives of flavonol and isoflavone

The reaction of the flavonol 3,7,3', 4'-tetra-O-methylquercetin (1) and of the isoflavone 7,4'-di-O-methylgenistein (2) with alkaline iodine in methanol afforded four new iodine derivatives: 8-iodo-5-hydroxy-3,7,3', 4'-tetramethoxy- flavone (1a) and 6-iodo-5-hydroxy-3,7,3', 4'-tetramethoxyflavone (1b) from 1; 2 afforded a mixture of two compounds, identified as a racemic mixture of (±)-trans-5-hydroxy-2,3,7,4'-tetramethoxy-8-iodo-isoflavanone (2a) and (±)-trans-5-hydroxy-2,3,7,4'-tetramethoxy-6,8-diiodo-isoflavanone (2b). The formation of these different products reveals a significant difference involving the chemical interaction between the reactive site of α, β-unsaturated ketones of flavonol and isoflavone under the tested reaction conditions (using I2/KOH/MeOH). Furthermore, the trans stereo selectivity is noteworthy in the nucleophylic addition of methanol at the isoflavone α, β-unsaturated system. The structures were identified on the basis of spectral data, mainly 1D and 2D NMR and mass spectra.

A reação do flavonol 3,7,3',4'-tetra-O-metilquercetina (1) e da isoflavona 7,4'-di-O-metilgenisteina (2) com iodo/KOH em metanol forneceu como produto quatro derivados iodados: 8-iodo-5-hidroxi-3,7,3',4'-tetrametoxiflavona (1a) e 6-iodo-5-hidroxi-3,7,3',4'-tetrametoxiflavona (1b) a partir da iodação de 1; a partir de 2 foi obtida uma mistura racêmica composta de (±)-trans-5-hidroxi-2,3,7,4'-tetrametoxi-8-iodo-isoflavanona (2a) e (±)-trans-5-hidroxi-2,3,7,4'-tetrametoxi-6,8-diiodo-isoflavanona (2b). A formação destes diferentes produtos revela a significante diferença envolvendo a interação química entre o sitio reativo de cetonas α, β-insaturadas de flavonol e de isoflavonas nas condições experimentais testadas (usando I2/KOH/MeOH). Além disso, ressalta-se a estereosseletividade trans na adição de metanol ao sistema α, β-insaturado da isoflavona. As estruturas foram identificadas com análise nos dados espectrométricos de RMN 1D e 2D e massas.

A new derivative of dihydroochnaflavone isolated from Luxemburgia species (Ochnaceae) and the complete ¹H and 13C NMR chemical shifts assignments / Um novo derivado da dihidroochnaflavona isolada de Luxemburgia species (Ochnaceae) e o completo assinalamento dos dados de RMN de ¹H e 13C

The biflavonoid 2",3"-dihydroochnaflavone, isolated from the Luxemburgia species (Ochanaceae), was treated with diazomethane to obtain the trimethyl-ether that was treated with pyridine/acetic anhydride to yield a new derivative, 5-acetil-7,4'-dimethyl-flavone-(3'→O-4'")-5"-acetil-7"-methyl-flavanone. The complete ¹H and 13C NMR data assignments of the new derivative were made by the one- and two-dimensional spectral analysis.

O biflavonóide 2",3"-diidroochnaflavona, isolada de espécies de Luxemburgia (Ochanaceae), foi tratada com diazometano e forneceu o éter trimetílico que, em seguida, foi tratado com anidrido acético/piridina obtendo-se um novo derivado, 5-acetil-7,4'-dimetil-flavona-(3'→O-4'")-5"-acetil-7"-metil-flavanona. Fez-se o completo assinalamento dos dados de RMN ¹H e 13C através da análise dos espectros uni- e bidimensionais do derivado.

Outros constituintes isolados de Licania arianeae (Chrysobalanaceae) / Other constituents isolated from Licania arianeae (Chrysobalanaceae)

O ácido flavona-6-sulfônico, 4'-O-metil-5,7-diidroxi-flavona-6-sulfonato, conhecido como niruriflavona, e a saponina, ácido 3-O-[6'-O-4-hidroxibenzoil]-²-D-galactopiranosil-ursa-12-en-28-óico, foram isolados, respectivamente, de madeira e folhas de Licania arianeae. As estruturas foram estabelecidas através da análise de espectros de massas e RMN incluindo experimentos bidimensionais.

The flavone-6-sulfonic acid, 4'-metil-5,7-dihydroxy-flavone-6-sulfonic acid, known as niruriflavone, and the saponin 3-O-[6'-O-4-hydroxybenzoyl]-²-D-galactopyranosyl-ursa-12-en-28-oic acid were isolated, respectively, from wood and leaves of Licania arianeae. The structures were established from the NMR and mass spectra data analysis including two-dimensional NMR experiments.

Atividade anti-helmíntica dos flavonóides isolados das raízes de Andira anthelmia (Leguminosae) / Anthelmintic activity of flavonoids isolated from roots of Andira anthelmia (Leguminosae)

As cascas e as raízes de A. anthelmia têm sido utilizadas tradicionalmente como vermífugas. Um estudo biomonitorado do extrato metanólico das raízes de A. anthelmia conduziu ao isolamento das isoflavonas biochanina A e genisteína da fração acetato de etila; biochanina A 7-O-β-D-glicopiranosídeo, biochanina A 7-O-α-L-rhamnopiranosil-(1→6)-β-D-glicopiranosídeo e biochanina A 7-O-β-D-apiofuranosil-(1→5)-β-D-apiofuranosil-(1→6)-β-D-glicopiranosídeo da fração n-butanólica e catequina da fração metanólica. Suas estruturas foram elucidadas com base em dados espectrométricos. A atividade anti-helmíntica foi investigada em camundongos naturalmente infectados por Aspiculuris tetraptera. Os compostos isolados aplicados nos animais por via intragástrica na dose de 2,0 mg.kg-1 durante três dias consecutivos revelaram percentuais significativos na eliminação de A. tetraptera, quando comparados com o lote controle.

Bioactivity-guided fractions of the methanol extract from the roots of Andira anthelmia led the isolation of the isoflavones biochanin A and genistein from the ethyl acetate fraction; biochanin A 7-O-β-D-glucopyranoside, biochanin A 7-O-α-L-rhamnopyranosyl-(1→6)β-D-glucopyranoside and biochanin A 7-O-β-D-apiofuranosyl-(1→5)-β-D-apiofuranosyl-(1→6)β-D-glucopyranoside from the n-butanol fraction and catechin from the methanol one. Their structures were elucidated on the basis of spectroscopy data. The anthelmintic activity was investigated in mice naturally infected by Aspiculuris tetraptera. The compounds administered in the animals by intragastric route in doses of 2.0 mg.kg-1, were effective in the removal of the total number of the A. tetraptera when compared with the control group.

Cornoside and other constituents from the latex of Parahancornia amapa (Hub. ) Ducke (Apocynaceae) a medicinal plant in Northern Brazil / Cornosídeo e outros constituintes do látex de Parahancornia amapa (Hub. ) Ducke (Apocynaceae) uma planta medicinal no Norte do Brasil

Latex of Parahancornia amapa which is known as "amapa milk" in folk medicine was extracted with hexane, dichloromethane and methanol. From the hexane and dichloromethane were identified mixtures of 3-O-acyl lupeol esters such as identified previously. In the methanol extract, a large amount of carbohydrates, the phenylethanoid glucoside known as cornoside, other phenylethanoids derivatives and methylmyoinositol were identified. The analysis of IR, NMR and GC-LRMS of the natural compounds and tetra-acetylcornoside and comparison with literature data were used to identify the compounds.

O látex de Parahancornia amapa, popularmente conhecido como "leite do amapá" foi extraído com hexano, diclorometano e metanol. As frações obtidas com hexano e diclorometano forneceram misturas de 3-O-acil-lupeol e triterpenos confirmando resultados de estudos já realizados. No extrato metanólico identificou-se uma grande quantidade de mistura de carboidratos, metilmioinositol e derivados de feniletanóides tendo como principal constituinte o cornosídeo. Estes constituintes foram identificados através da análise de espectros de IV, RMN ¹H e 13C e CG-EM das frações e do derivado acetilado do cornosídeo e do metilmioinositol.

Metabólitos especiais isolados de Laseguea erecta (Apocynaceae) / Special metabolites isolated from Laseguea erecta (Apocynaceae)

Do caule de Laseguea erecta foram isolados o lupeol, a cumarina escopoletina, o lignóide pinoresinol e o glicosil-cardenoídeo, alfa-L-tevetosil-digitoxigenina. As estruturas foram identificadas com o uso de técnicas espectroscópicas de IV, RMN ¹H e 13C, incluindo técnicas especiais 1D e 2D, espectroscopia de massas e comparação com dados da literatura.

From the stem of Laseguea erecta the triterpene lupeol, the cumarine scopoletin, the lignoid pinoresinol and digitoxigenin alpha-L-tevetoside, known as thevetioside, were isolated. The structures were identified by IR, mass, ¹H and 13C NMR spectroscopy, including 1D and 2D techniques, together with comparison with literature data.

Pimarane Diterpenes and a Sesquiterpene from Salzmmania nitida

O estudo fitoquímico de Salzmmania nitida D.C. (Rubiaceae) conduziu ao isolamento e identificação de dois novos terpenoides, (+)-3-oxo-thermarol e 11-acetoxi-4alfa-metil-5alfa-eudesmanol além do (+)-termarol. As estruturas foram estabelecidas com base na análise de espectros de IV, Massas e RMN de 1H e 13C (1D e 2D).

New triterpene isolated from Eschweilera longipes (Lecythidaceae)

The phytochemical studies of Eschweilera longipes Miers (Lecythidaceae) have led to the identification of a new triterpene 3beta, 24-dihydroxyfriedelane, the known 1beta, 2beta, 3beta, 19beta-tetrahydroxyurs-12-en-28-oic acid (1beta-hydroxyeucaphic acid) besides the saponin sitosterol 3betaO-betaD-glucopyranoside. The structures were established from the IR, NMR and mass spectra data including 2D NMR experiments of natural substances and of the acetyl derivative of the new triterpene

Ação anti-helmíntica de extratos brutos de andira anthelmia (Vell.) Macbr. e Andira fraxinifolia Benth., camundongos naturalmente infectados por vampirolepis nana e aspiculuris tetraptera vampirolepis nana e aspiculuris tetraptera / Anthelmintic action of the crude extracts of andira anthelmia (Vell.) Macbr. and andira fraxinifolia Benth., in mice vampirolepis nana and aspiculuris tetraptera naturally infected by vampirolepis nana and aspiculuris tetraptera

A atividade anti-helmíntica dos extratos brutos da folha fresca e seca, casca do tronco e da raiz da espécie Andira anthelmia e A. fraxinifolia, foi avaliada sob as espécies Vampirolepis nana e Aspiculuris tetraptera. Foram utilizadas as doses de 8 g/kg/dia para folhas e casca do tronco, e de 1, 2, 4 e 8 g/kg/dia para a casca da raiz de A. anthelmia, e as doses de 8 g/kg/dia para folhas e casca da raiz, e de 4, 8 e 16 g/kg/dia para a casca do tronco de A. fraxinifolia. A dose de 8 g/kg/dia do extrato bruto da folha fresca e seca, da casca do tronco e da raiz, quando comparadas, não apresentaram diferença significativa no percentual de eliminação de V. nana, 14,9 per cent, 16,4 per cent, 6,3 per cent, 17,9 per cent , respectivamente, o mesmo ocorreu quando comparadas ao grupo controle (7,4 per cent). As doses de 2 e 4 g/kg/dia, 49,4 per cent e 42,7 per cent, respectivamente, foram significativa-mente mais ativas para V. nana, em comparação com as demais partes anatômicas e o grupo controle, não apresentando diferença em relação a dose de 1 g/kg/dia da casca da raiz e do mebendazol. A dose 2 g/kg/dia foi significati-vamente mais ativa para A. tetraptera (63,2 per cent), em comparação com as folhas, a casca da raiz nas doses de 1 e 4 g/kg/dia, e o grupo controle, 1,2 per cent, 1,7 per cent, 31,7 per cent, 15,3 percent, 0,1 per cent, respec-tivamente. Contudo, não apresentou diferença significativa em relação ao nitroscanato, sendo menos ativa do que o mebendazol. Embora a dose de 8 g/kg/dia da casca do tronco de A. fraxinifolia tenha apresentado um percentual de eliminação de V. nana maior (37,5 per cent), não foi observado diferença estatística, quando comparado com as demais doses, partes anatômicas, grupo controle e o mebendazol. Similarmente, não foi observado diferença significativa nos percentuais de eliminação de A. tetraptera. Os resultados sugerem o extrato bruto da casca da raiz de A. anthelmia como anti-helmíntico promissor, necessitando de estudos complementares, devido a alta toxicidade apresentada.