7-Epiclusianona, a nova benzofenona tetraprenilada e outros constituintes químicos dos frutos de Rheedia gardneriana

Phytochemical investigation of the fruits of Rheedia gardneriana led to the isolation of sesquiterpenes mixture, methyl esters of fatty acids (palmitate, estearate, oleate, linoleate, linolenate), sugars (galactose, glucose, fructose), triterpene (oleanolic acid), steroids mixture (stigmasterol and sitosterol) and the new tetraprenylated benzophenone 7-epiclusianone.

Lupeol

The title compound [systematic name: 3 beta-lup-20(29)-en-3-ol], C(30)H(50)O, was isolated from the leaves of Garcinia brasiliensis (common name: bacupari; a member of the Guttiferae family) and has been shown to have many useful medicinal and biological properties. The lupeol molecule consists of four six-membered rings (adopting chair conformations) and one five-membered ring (with an envelope conformation), all fused in trans fashion. Lupeol is isomorphic with the pentacyclic triterpene 3 beta,30-dihydroxylup-20(29)-ene, which differs from lupeol due to the presence of an additional hydroxy group. The crystal packing is stabilized by van der Waals interactions and intermolecular O-H center dot center dot center dot O hydrogen bonds, giving rise to an infinite helical chain along the c axis.

Catálogo sistemático dos pólens das plantas arbóreas do Brasil Meridional: III - Theaceae, Marcgraviaceae, Ochnaceae, Guttiferae e Quiinaceae

Weitere fuenf Familien werden in diesem 3. Teil des Katalogs der Baumpollen Suedbrasiliens auf ihre Pollenkoerner hin untersucht. Es handelt sich dabei um die Theaceae, Marcgraviaceae, Ochnaceae, Guttiferae und Quiinaceae. Phyllogenetisch schliessen sich diese Fainilien an die Dlleniaceae an. Die Pollenkoerner von Laplacea (Theaceae) unterscheiden sich deutlich von allen der anderen untersuchten Familien. Sie sind dreiporig und haben eine mit Stacheln besetzte Oberflaeche. Bei Marcgravia polyantha und Noranthea brasiliensis (Marcgraviaceae) stossen wir auf Pollenkoerner mit je drei Colpori. Beide Arten lassen sich aber durch ihre verschiedene Oberflaechenstruktur unterscheiden. Ouratea parviflora (Ochnaceae) hat sehr aehnliche Pollenkoerner wie Noranthea brasiliensis, mit drei Colpori, jedoch gleichzeitig auch andere mit vier Colpori. Unter den Guttiferae finden wir eine eigenartige Form bei Kielmeyera, deren Pollenkoerner alle in Tetraden auftreten. Das einzelne Korn hat wieder grosse Aehnlichkelt mit dem von Caryocar brasiliense (Caryoearaceae). Calophyllum brasiliense und Rheedia gardneriana unterscheiden sich erstens durch den groesseren Durchmesser der Koerner bei C. brasiliense und zweitens durch eine feinere Oberflaechenstruktur bei R, gardneriana. Clusia criuva ist dreiporig. Quiina glaziovii (Quiinaceae) ist vierporig und besitzt grosse Aehnlichkeit mit den Pollenkoernern von Davilla rugosa (Dilleniaceae).

Estrutura horizontal e vertical do componente arbóreo em fase de regeneração natural na mata Santa Luzia, no município de Catende-PE

O estudo foi desenvolvido no fragmento denominado Mata Santa Luzia, situado no Município de Catende, PE, nas coordenadas 8º72'49" S e 35º72'47" W, altitude de 239 m, com os objetivos de avaliar a regeneração natural total de espécies arbóreas no fragmento florestal e verificar a diversidade e estrutura das espécies nessa área. Para a estimativa da regeneração natural das espécies arbóreas no fragmento, foram locadas de forma sistemática 15 subparcelas permanentes de 25 m² (5 x 5 m), equidistantes em 50 m. O nível de inclusão adotado foi de CAP < 15 cm e as medições de altura (h), divididas em três classes, em que a classe 1 contemplou indivíduos com 1,0 < h < 2,0 m, a classe 2 com indivíduos 2,0 < h < 3,0 m e a classe 3 com indivíduos com h > 3,0 m. No fragmento foram amostrados 107 indivíduos vivos, pertencentes a 25 famílias botânicas e 36 táxons. Dessas, 33 foram identificadas em nível de espécie, duas em nível de gênero e uma se apresentou como indeterminada. As cinco espécies com maiores valores para regeneração natural total (RNT) foram assim distribuídas: Rheedia gardneriana Planch. & Triana (9,9%), Cupania racemosa (Vell.) Radlk (7,7%), Brosimum discolor Schott (7,4%), Vismia guianensis (Aubl.) Pers. (6,1%) e Protium heptaphyllum (Aubl.) Marchand (5,9%). Provavelmente, essas espécies no futuro serão as principais responsáveis pela manutenção da estrutura e fisionomia da floresta.

Antimicrobial activity of Rheedia brasiliensis and 7-epiclusianone against Streptococcus mutans

This in vitro study evaluated the antimicrobial activity of extracts obtained from Rheedia brasiliensis fruit (bacupari) and its bioactive compound against Streptococcus mutans. Hexane, ethyl-acetate and ethanolic extracts obtained (concentrations ranging from 6.25 to 800 mu g/ml) were tested against S. mutans UA159 through MIC/MBC assays. S. mutans 5-days-old biofilms were treated with the active extracts (100 x MIC) for 0, 1, 2, 3 and 4 h (time-kill) and plated for colony counting (CFU/ml). Active extracts were submitted to exploratory chemical analyses so as to isolate and identify the bioactive compound using spectroscopic methods. The bioactive compound (concentrations ranging from 0.625 to 80 mu g/ml) was then tested through MIC/MBC assays. Peel and seed hexane extracts showed antimicrobial activity against planktonic cells at low concentrations and were thus selected for the time kill test. These hexane extracts reduced S. mutans biofilm viability after 4 h, certifying of the bioactive compound presence. The bioactive compound identified was the polyprenylated benzophenone 7-epiclusianone, which showed a good antimicrobial activity at low concentrations (MIC: 1.25-2.5 mu g/ml; MBC: 10-20 mu g/ml). The results indicated that 7-epiclusianone may be used as a new agent to control S. mutans biofilms; however, more studies are needed to further elucidate the mechanisms of action and the anticariogenic potential of such compound found in R. brasiliensis. (C) 2008 Elsevier GmbH. All rights reserved.

PRENYLATED XANTHONES FROM Rheedia acuminata

Pyranojacareubin; 1,5-dihydroxy-6',6'-dimethyl-2H-pyran(2',3':6,7) -6",6"-dim-ethyI-2H,4H-pyran(2",3":2,3)xanthone and a new xanthone l,6-dihydroxy-5-methoxy-6',6'-dim-ethyl-2H-pyran(2',3':3,2)-7-(3,3-dimethylprop-2-enyl)xanthone were isolated from the ether extract of the root bark of Rheedia acuminata together with friedelin and friedelanol.

PRENYLATED XANTHONES FROM Rheedia acuminata (reprinted from Acta Amazônica, 23(2/3):181-185)

Pyranojacareubin; 1,5-dihydroxy-6',6'-dimethyl-2H-pyran(2,,3':6,7) -6",6"-dime-thyl-2H,4H-pyran(2",3":2,3)xanthone and a new xanthone l,6-dihydroxy-5-methoxy-6',6'-dime-thyl-2H-pyran(2',3':3,2)-7-(3,3-dimethylprop-2-enyl)xanthone were isolated from the ether extract of the root bark of Rheedia acuminata together with friedelin and friedelanol.

Analgesic and anti-inflammatory activity of the aqueous extract of Rheedia longifolia Planch & Triana

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.

Caracterização morfológica da semente e da plântula de bacurizinho (Rheedia acuminata (Ruiz et Pav.) Plachon et Triana - Clusiaceae)

O bacurizinho é uma espécie frutífera do gênero Rheedia, nativa da Amazônia, e raramente cultivada, pois seus frutos, embora comestíveis, apresentam polpa escassa. Os estudos com o bacurizinho visam a sua utilização como porta-enxerto, redutor de porte para outras espécies do gênero Rheedia e Garcinia que apresentam altura elevada, como o bacuripari (Rheedia macrophylla Planchon et Triana- Clusiaceae) e o mangostão (Garcinia mangostana L.). Este trabalho teve como objetivo caracterizar, morfologicamente, a semente e a plântula dessa espécie. A semente é exalbuminosa, bitegumentada, com a testa de coloração marrom, apresentando vários feixes vasculares bem visíveis, distinguindo-se por sua coloração um pouco mais clara. O hilo é arredondado, de coloração escura, com pequena região mais clara ao centro, correspondendo no ponto de entrada de feixe vascular. A micrópila situa-se próxima ao hilo, sobre uma pequena protuberância triangular. O embrião é anômalo, hipocotilar e é representado unicamente por um longo eixo hipocótilo-radícula, sendo os cotilédones diminutos, aparecendo apenas na extremidade superior no lado oposto da micrópila. Durante a germinação, ocorre primeiramente a emergência de delgada raiz primária, no pólo oposto onde será originado o epicótilo. Essa raiz cresce aproximadamente 5-7cm e cessa, fenecendo posteriormente. Por ocasião da emergência do epicótilo, ocorre ao mesmo tempo a formação de uma raiz adventícia, na base do epicótilo, bem mais robusta que a anterior e que se constituirá no sistema radicular da planta. Precedendo a abertura do primeiro par de metáfilos, desenvolvem-se no epicótilo três pares de catafilos opostos e de coloração esverdeada. A germinação é hipógea e a plântula do tipo criptocotiledonar.

Estaquia como processo de clonagem do bacuripari (Redhia gardneriana Miers ex Planch e Triana)

No Brasil, existem diversas fruteiras nativas com potencial de exploração comercial, especialmente na Amazônia, local de origem do bacuripari. Neste sentido, realizou-se um trabalho com o objetivo de avaliar a clonagem dessa espécie pelo processo da estaquia, mediante uso de ácido indolil-3-butírico (AIB), em condições de nebulização intermitente. O delineamento experimental foi o inteiramente casualizado, com 5 tratamentos, caracterizados pelas concentrações de AIB (0; 1.000; 3.000; 5.000 e 7.000 mg.L-1), com 4 repetições e 10 estacas por parcela. Foram avaliados na porcentagem de estacas enraizadas, o número médio de folhas e o comprimento de raízes. O uso de AIB não influenciou na porcentagem de enraizamento.

Viscoelásticos oftálmicos: comparação entre os comerciais e formulações de galactomanana de Dimorphandra gardneriana

Ophthalmic viscosurgical devices (OVD) are materials injected in intraocular space during cataract removal to reduce trauma in the patient's eye. Three Brazilian commercially available OVDs (Medilon®, Metilcelulose® and Ofthyal®) were evaluated as well as formulations based on Dimorphandra gardneriana galactomannan. Viscosity and viscoelastic parameters, such as viscosity at zero shear, pseudoplasticity index, elastic and viscous moduli, relaxation time, were determined and compared. Characteristics of an effective OVD were proposed. None of the Brazilian devices studied fulfill the rheological requirements. Only the galactomannan at 3% concentration showed potential to be used as effective OVD.

Constituintes químicos e atividade antioxidante de Byrsonima gardneriana (Malpighiaceae)

The phytochemical investigation of Byrsonima gardneriana led to the isolation of five triterpenes and one flavonoid: D:B-Friedoolean-5-en-3-one (1), friedoolean-14-en-3-one (2), friedelan-3-one (3), lup-20(29)-en-3-ol (4), 3β-hydroxiolean-12-ene (5) and 3,3',4',5,7-pentahydroxyflavan (6). Their structures were assigned based on spectroscopic analyses, including two-dimensional NMR techniques and comparison with published spectral data. Antioxidant activities of ethanol extract and phases were measured using the 1,2-diphenyl- 2-picryl-hydrazyl (DPPH) free radical scavenging assay, evaluation of total phenolic content and trolox equivalent antioxidant capacity (TEAC).

Leishmanicidal and cholinesterase inhibiting activities of phenolic compounds of Dimorphandra gardneriana and Platymiscium floribundum, native plants from Caatinga biome

In recent years, the Brazilian Health Ministry and the World Health Organization have supported research into new technologies that may contribute to the surveillance, new treatments, and control of visceral leishmaniasis within the country. In light of this, the aim of this study was to isolate compounds from plants of the Caatinga biome, and to investigate their toxicity against promastigote and amastigote forms of Leishmania infantum chagasi, the main responsible parasite for South American visceral leishmaniasis, and evaluate their ability to inhibit acetylcholinesterase enzyme (AChE). A screen assay using luciferase-expressing promastigote form and an in situ ELISA assay were used to measure the viability of promastigote and amastigote forms, respectively, after exposure to these substances. The MTT colorimetric assay was performed to determine the toxicity of these compounds in murine monocytic RAW 264.7 cell line. All compounds were tested in vitro for their anti-cholinesterase properties. A coumarin, scoparone, was isolated from Platymiscium floribundum stems, and the flavonoids rutin and quercetin were isolated from Dimorphandra gardneriana beans. These compounds were purified using silica gel column chromatography, eluted with organic solvents in mixtures of increasing polarity, and identified by spectral analysis. In the leishmanicidal assays, the compounds showed dose-dependent efficacy against the extracellular promastigote forms, with an EC50 for scoporone of 21.4µg/mL, quercetin and rutin 26 and 30.3µg/mL, respectively. The flavonoids presented comparable results to the positive control drug, amphotericin B, against the amastigote forms with EC50 for quercetin and rutin of 10.6 and 43.3µg/mL, respectively. All compounds inhibited AChE with inhibition zones varying from 0.8 to 0.6, indicating a possible mechanism of action for leishmacicidal activity.

Estaquia como processo de clonagem do bacuripari (Redhia gardneriana Miers ex Planch e Triana)

No Brasil, existem diversas fruteiras nativas com potencial de exploração comercial, especialmente na Amazônia, local de origem do bacuripari. Neste sentido, realizou-se um trabalho com o objetivo de avaliar a clonagem dessa espécie pelo processo da estaquia, mediante uso de ácido indolil-3-butírico (AIB), em condições de nebulização intermitente. O delineamento experimental foi o inteiramente casualizado, com 5 tratamentos, caracterizados pelas concentrações de AIB (0; 1.000; 3.000; 5.000 e 7.000 mg.L-1), com 4 repetições e 10 estacas por parcela. Foram avaliados na porcentagem de estacas enraizadas, o número médio de folhas e o comprimento de raízes. O uso de AIB não influenciou na porcentagem de enraizamento.

Detecção in silico, isolamento e caracterização estrutural dos constitutintes micromoleculares antimaláricos e antioxidantes em galhosmdemGarcina gardneriana (Clusiaceae)

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