BACKGROUND Sporothrix brasiliensis is the causative agent of zoonotic cases of sporotrichosis in Brazil and is associated with atypical and severe presentations in cats, dogs, and humans. Sporotrichosis treatment is usually time- and cost-consuming, sometimes with poor response and host toxicity. Schinus terebinthifolius has proven efficacy against bacteria and fungi of clinical interest. OBJECTIVE To determine the in vitro activity of S. terebinthifolius against S. brasiliensis. METHODS Five S. brasiliensis isolates and three reference strains were subjected to a hydroethanol extract derived from the leaves of S. terebinthifolius and its fractions. The minimal inhibitory concentration (MIC) was determined using the broth microdilution method according to the M38-A2 CLSI guidelines. Also, the fungicidal/fungistatic activity of the extract and fractions was studied. FINDINGS The crude extract of S. terebinthifolius inhibited the growth of S. brasiliensis (MIC: 0.5-1.0 µg/mL), while the partitioned extracts dichloromethane, ethyl acetate, and butanol demonstrated growth inhibition at 8 µg/mL due to a fungistatic activity. MAIN CONCLUSIONS Due to its in vitro efficacy against S. brasiliensis and its known pharmacological safety, S. terebinthifolius is a candidate to be tested using in vivo models of sporotrichosis.

Resumen Esta investigación se llevó a cabo para evaluar los efectos de los extractos de Rheedia longifolia (Clusiaceae), Garcinia xanthochymus (Clusiaceae), Plumbago scandens (Plumbaginaceae) Hovenia dulcis (Rhamnaceae), Malpighia glabra (Malpighiaceae), Euphorbia tirucalli (Euphorbiaceae) y Nerium adelfa (Apocynaceae) sobre la tasa incubación de los huevos de Dermacentor (Anocentor) nitens y Ripicephalus sanguineus (Acari: Ixodidae) en concentraciones de 1.000 ppm. Los extractos de R. longifolia, H. dulcis, M. glabra y E. tirucalli retrasaron significativamente la incubación de los huevos de R. sanguineus en tres días, pero los grupos tratados con los extractos de G. xanthochymus y P. scandens eclosionaron después de 14 días. Para las garrapatas D. (A.) nitens, los extractos de H. dulcis y N. adelfa retrasaron la eclosión de los huevos durante tres días, sin embargo, la acción de los extractos de R. longifolia, G. xanthochymus, P. scandens y E. tirucalli causó un retraso mayor de siete días. Para los dos tipos de garrapatas, los huevos del grupo control tardaron un día para eclosionar. Los extractos H. dulcis y M. glabra fueron eficaces in vitro en huevos de R. sanguineus (89 %) y D. (A.) nitens (100 %) y se pueden considerar como candidatos potenciales para el control biológico de estas garrapatas.

Abstract This investigation was carried out to evaluate the effects of the plant extracts of Rheedia longifolia (Clusiaceae), Garcinia xanthochymus (Clusiaceae), Plumbago scandens (Plumbaginaceae), Hovenia dulcis (Rhamnaceae), Malpighia glabra (Malpighiaceae), Euphorbia tirucalli (Euphorbiaceae) and Nerium adelfa (Apocynaceae) on eggs of Dermacentor (Anocentor) nitens and Ripicephalus sanguineus (Acari: Ixodidae) at concentrations of 1,000 ppm. The extracts had a significant effect on the hatching rate of eggs. The extracts of R. longifolia, H. dulcis, M. glabra and E. tirucalli delayed the hatching of R. sanguineus eggs by three days; however, the group treated with the extracts of G. xanthochymus and P. scandens did not hatch until day fourteen. For the tick D. (A.) nitens, extracts of H. dulcis and N. oleander delayed egg hatching by three days; however, the action of extracts from R. longifolia, G. xanthochymus, P. scandens and E. tirucalli caused a delay of seven days. For the control groups of both species, eggs hatched in one day. H. dulcis and M. glabra were effective in vitro on eggs of R. sanguineus and D. (A.) nitens (89 and 100 %, respectively), and can be considered to be potential candidates for the biocontrol of those ticks.

Derivados de benzofenonas despertam grande interesse científico. A família Clusiaceae é conhecida por produzir grandes quantidades dessas substâncias, com vários resíduos isoprênicos em suas estruturas, os quais são responsáveis pela complexidade e variedade estrutural observada nesta classe de substâncias, e também contribuem para suas atividades biológicas. Clusia é um gênero importante pertencente à família Clusiaceae, com 55 benzofenonas poliisopreniladas diferentes identificadas até o momento. Essas substâncias foram analisadas sob perspectivas biossintéticas e quimiossistemáticas, permitindo determinar características relacionadas à sua produção, acumulação e distribuição dentro desse gênero. As benzofenonas poliisopreniladas encontradas em Clusia apresentaram um grau elevado de prenilação, com 2 a 5 unidades isoprênicas e uma maior ocorrência em flores e frutos. A seção Cordylandra mostrou uma ocorrência muito semelhante de derivados de 2,4,6-triidroxibenzofenona e biciclo[3.3.1]nonano-2,4,9-triona, a maioria deles com 4 unidades isoprênicas. Na seção Anandrogyne predominam derivados de 2,4,6-triidroxibenzofenona com 2 unidades isoprênicas, e em Chlamydoclusia predominam os derivados de biciclo[3.3.1]nonano-2,4,9-triona com 4 unidades isoprênicas. Embora altamente preniladas, essas substâncias mostraram índices de oxidação baixos, o que, sob uma perspectiva evolucionária, corrobora o fato de que Clusiaceae é uma família em transição, com alguns aspectos comuns tanto à famílias botânicas basais, quanto derivadas.

Benzophenone derivatives are special metabolites that arouse great scientific interest. The Clusiaceae family is known for producing large amounts of benzophenone derivatives with several isoprene residues on their structures, which are responsible for the observed complexity and structural variety in this class of substances, and also contribute to their biological activities. Clusia is an important genus belonging to Clusiaceae, with 55 different polyisoprenylated benzophenones identified so far. These substances were analyzed from biosynthetic and chemosystematic points of view, allowing the determination of characteristics regarding their production, accumulation and distribution within this genus. Polyisoprenylated benzophenones found in Clusiashowed a high prenylation degree, with 2 to 5 isoprene units and a greater occurrence in flowers and fruits. Section Cordylandra showed a very similar occurrence of 2,4,6-trihydroxybenzophenone derivatives and bicyclo[3.3.1]nonane-2,4,9-trione derivatives, the majority of them with 4 isoprene units. In section Anandrogyne there is a predominance of simple 2,4,6-trihydroxy-benzophenone derivatives, with 2 isoprene units, and in Chlamydoclusia predominates bicyclo[3.3.1]nonane-2,4,9-trione derivatives with 4 isoprene units. Although highly prenylated, these substances showed low oxidation indexes, which from an evolutionary perspective corroborates the fact that Clusiaceae is a family in transition, with some common aspects with both basal and derived botanical families.

Our solemn homage to the great Master Otto R. Gottlieb who knew how to teach the mystery of evolutionary relationships between chemistry and its natural sources. The micromolecular chemical study of the family Bignoniaceae shows a profile predominantly characterized by the occurrence of metabolites derived from acetic acid biosynthetic pathways such as terpenoids, quinones, flavonoids and special aromatic derivatives. Analysis of different chemosystematic parameters for the metabolite data collected, provided valuable information for the systematic characterization of the Bignoniaceae family within the Angiosperm derived taxa.

Plumbago scandens L. é uma espécie brasileira tropical/subtropical que ocorre ao longo da costa. Quimicamente, é principalmente representada por naftoquinonas, flavonóides, terpenóides e esteróides. objetivo do presente trabalho é estudar mudanças quantitativas da produção metabólica nas raízes de Plumbago scandens durante diferentes estágios de desenvolvimento fisiológico, relativos à floração. Os resultados indicaram a presença de quatro substâncias nos extratos: plumbagina, epi-isoshinanolona, ácido palmítico e sitosterol, independente do estágio de desenvolvimento. A naftoquinona plumbagina tem sempre mostrado ser o componente majoritário de todos os extratos. Naftoquinonas exibiram seus maiores conteúdos durante a floração, enquanto o conteúdo dos dois outros componentes decresceu durante este estágio, revelando um perfil inverso. A composição química modificou dependendo das necessidades da planta.

Plumbago scandens L. is a Brazilian tropical/subtropical species that occurs along the coast. Chemically it is mainly represented by naphthoquinones, flavonoids, terpenoids and steroids. The aim of the present work is to study quantitative changes in the root metabolic production of Plumbago scandens during different physiologic developmental stages relative to floration. The results indicated the presence of four substances in the extracts: plumbagin, epi-isoshinanolone, palmitic acid and sitosterol, independent on developmental stage. The naphthoquinone plumbagin has always showed to be the major component of all extracts. Naphthoquinones exhibited their highest content during floration, while the content of the two others components decreased during this stage, revealing an inverse profile. The chemical composition changed depending on the plant requirements.

Rheedia longifolia Planch et Triana belongs to the Clusiaceae family. This plant is widely distributed in Brazil, but its chemical and pharmacological properties have not yet been studied. We report here that leaves aqueous extract of R. longifolia (LAE) shows analgesic and anti-inflammatory effects. Oral or intraperitoneal administration of this extract dose-dependently inhibited the abdominal constrictions induced by acetic acid in mice. The analgesic effect and the duration of action were similar to those observed with sodium diclofenac, a classical non-steroidal analgesic. In addition to the effect seen in the abdominal constriction model, LAE was also able to inhibit the hyperalgesia induced by lipopolysaccharide from gram-negative bacteria (LPS) in rats. We also found that R. longifolia LAE inhibited an inflammatory reaction induced by LPS in the pleural cavity of mice. Acute toxicity was evaluated in mice treated with the extract for seven days with 50 mg/kg/day. Neither death, nor alterations in weight, blood leukocyte counts or hematocrit were noted. Our results suggest that aqueous extract from R. longifolia leaves has analgesic and anti-inflammatory activity with minimal toxicity and are therefore endowed with a potential for pharmacological control of pain and inflammation.

Análise por cromatografia com fase gasosa e cromatografia com fase gasosa acoplada à espectrometria de massas de óleos essenciais obtidos de folhas de Echinodorus grandiflorus ("Chapéu-de-couro") em duas diferentes populações (folhas grandes e folhas pequenas), coletadas mensalmente entre setembro de 1998 e dezembro de 1999, revelou 17 componentes. Fitol foi o constituinte majoritário em ambas populações. Os principais representantes sesquiterpênicos foram (E)-cariofileno, alfa-humuleno e (E)-nerolidol.

Analysis by Gas Chromatography and Gas Chromatography/Mass Spectrometry of the essential oils obtained from leaves of Echinodorus grandiflorus ("Chapéu de couro") from two different populations (Big Leaves and Small Leaves), collected monthly between September 1998 and December 1999 revealed 17 components. Phytol was the major constituent for both populations. The main sesquiterpene representatives are (E)-caryophyllene, alpha-humulene and (E)-nerolidol.

O gênero Plumbago pertence à família Plumbaginaceae e apresenta uma variedade de atividades biológicas, a maioria atribuída à presença de naftoquinonas. Plumbagina é uma naftoquinona natural que pode ser obtida a partir de raízes de Plumbago scandens L. Na tentativa de descobrir a melhor técnica de extração dessa substância foram usadas, maceração estática, maceração dinâmica, extração com auxílio de ultrassom e extração em Soxhlet. Quatro substâncias foram detectadas qualitativamente: as naftoquinonas plumbagina e epi-isoshinanolona, o ácido palmítico e o sitosterol. Plumbagina foi sempre o componente majoritário em todos os extratos analisados e sua determinação quantitativa foi realizada através de cromatografia com fase gasosa acoplada à espectrometria de massas. A extração em Soxhlet foi a técnica mais eficiente para obtenção de plumbagina, entretanto a longa exposição a temperaturas elevadas favoreceu a degradação da plumbagina.

The Plumbago genus belongs to the Plumbaginaceae family and it is known due to its variety of biological uses, most of them attributed to the presence of naphthoquinones. Plumbagin is a naturally occurring naphthoquinone that can be obtained from roots of Plumbago scandens L. In order to find out the better technique for plumbagin extraction, were applied: static maceration, dynamic maceration, with assistance of ultrasonic waves and in Soxhlet apparatus. Four compounds were qualitatively detected in all extracts: the naphthoquinones plumbagin and epi-isoshinanolone, palmitic acid and sitosterol. Plumbagin was always the major component in all analyzed extracts and it was quantitatively determined by gas chromatograph coupled with mass spectrometer. Soxhlet was the most efficient extraction technique however, prolonged heating time promoted plumbagin degradation.

Plumbagin is a naturally occurring naphthoquinone isolated from roots of Plumbago scandens. The plant was collected at the Campus of Fundação Oswaldo Cruz, Rio de Janeiro, Brazil. P. scandens is used as a traditional medicine for the treatment of several diseases. The antimicrobial activity of plumbagin was evaluated using the macrodilution method. The compound exhibited relatively specific activity against bacteria and yeast. The minimum inhibitory concentration test showed the growth inhibiton of Staphylococcus aureus at a concentration of 1.56 µg/ml and of Candida albicans at a concentration of 0.78 µg/ml. These results suggest the naphthoquinone plumbagin as a promising antimicrobial agent.

ABSTRACT Plumbaginales belongs to the superorder Malviflorae and comprises two families, Plumbaginaceae and Limoniaceae. Its representatives are chemically characterized by the presence of naphthoquinones, flavonoids, terpenoids and steroids, many of them being the responsible for biodynamic activities. The extracts of some species of Plumbaginales and also some isolated compounds revealed to be of great importance in the search of new drugs, since they have been described in literature for the treatment of many diseases such as: leishmaniasis, Chagas' disease, malaria, cancer and others. Plants represent a valuable source of bioactive compounds and should be investigated, as a promise in the development of effective, ready available and lesscostly drugs families Limoniaceae naphthoquinones flavonoids steroids activities leishmaniasis Chagas disease malaria others investigated effective

The genus Plumbago belongs to the family Plumbaginaceae, order Plumbaginales. Comparative chemical profile of P. scandens (native) and P. auriculata (cultivated) was obtained by normal and reversed-phase high performance liquid chromatography with photodiode array detector. Comparison of the ultraviolet espectra and the retention times for the compounds allowed to find similar metabolic patterns in roots, stems and leaves. Four flavonoids, one phenolic acid or derivative and the naphtoquinone plumbagin were comparatively identified to standards.

Muitas são as substâncias do metabolismo vegetal que têm despertado grande interesse, principalmente no setor de fármacos. No presente estudo, foram avaliadas as atividades antineoplásica e tripanocida de extratos vegetais de Hovenia dulcis (Rhamnaceae) cultivada sob condições in vivo e in vitro. Extratos metanólicos das folhas de material jovem desenvolvido in vivo e in vitro, exibiram altas porcentagens na inibição do crescimento de todas as linhagens de células tumorais testadas, enquanto extratos etanólicos do pseudofruto mostraram seletividade com elevado percentual de inibição do crescimento celular nas linhagens SP2/0 e BW. Quanto à atividade tripanocida, os extratos aquoso do pseudofruto e metanólico das folhas das plantas germinadas in vivo, apresentaram percentual de inibição em 48 h, de 95% e 100%, respectivamente.

Plants produce a wide range of secondary metabolites, many of which are pharmaceutically important. In this paper were evaluated anti-cancer and trypanocidal activities from Hovenia dulcis (Rhamnaceae) in vivo and in vitro propagated plants. Methanolic extracts of young leaves from in vivo and in vitro material were remarkably active for all tumor cells lines tested, while ethanolic extracts of pseudofruit showed high degree of selectivity against to SP2/0 and BW cells in culture. Mortality of 95 and 100% (48 h) on Trypanosoma cruzi were observed on the aqueous extract of pseudofruit and methanolic extracts of leaves from seedlings.

ABSTRACT Plumbaginaceae is composed by perennial herbs or subshrubs of cosmopolitan distribution. The present study aimed to evaluate the content of condensed tannins from leaves of two Plumbaginaceae species Plumbago auriculata Lam. e Plumbago scandens L. The tannin extraction was carried out by acid hydrolysis and the quantification was obtained through colorimetric analysis using epicatechin as standard sample. The results indicated a high tannin production in Plumbago auriculata while the slight content was found in P. scandens, indicating these metabolites as important differential markers of these plants.

RESUMO A família Plumbaginaceae é constituída por ervas ou subarbustos perenes de distribuição cosmopolita. O presente estudo visou avaliar o teor de taninos condensados em folhas de duas espécies de Plumbaginaceae: Plumbago auriculata Lam. e Plumbago scandens L. A extração dos taninos foi realizada através de hidrólise ácida e a quantificação foi feita através de análise colorimétrica em comparação com um padrão (epicatequina). Os resultados obtidos indicam uma produção maior de taninos condensados em Plumbago auriculata, em detrimento da sua baixa produção em P. scandens, indicando essa classe metabólica como importante marcador diferencial dessas plantas.