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.

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.

Invasão de ecossistemas por Acacia longifolia - caracterização da entomofauna associada e identificação de potenciais polinizadores

Dissertação para a obtenção do Grau de Mestre em Engenharia do Ambiente, perfil de Engenharia Ecológica

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.

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.

Pulmonaria longifolia (Bast.) Boreau subsp. longifolia al massis de Garraf

Pulmonaria

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.

Alkaloids and volatile constituents from the stem of Fusaea longifolia (Aubl.) Saff. (Annonaceae)

ABSTRACT: A phytochemical study of the ethanol extract and an extraction of the volatile compounds, performed by means of Clevenger apparatus were carried out with the stem of Fusaea longifolia (Aubl.) Saff. (Annonaceae). The ethanol extract yielded O-methylmoschatoline, isolated for the first time in this species, and stepholidine, reported for the first time in genus Fusaea. The structural identification of the alkaloids was made based on the analysis of their NMR spectra. Through the use of GC and GC-MS, two sesquiterpenoids, a-cadinol (12.5%) and spatulenol (12.0%) were identified as the major constituents of the essential oil.

Secondary metabolites from Spirotropis longifolia (DC) Baill and their antifungal activity against human pathogenic fungi

A phytochemical study of the ethyl acetate extract of the roots and adventitious roots of Spirotropis longifolia, a monodominant tree species of the Guianan rainforest, has allowed the isolation of three compounds: 2- hydroxy-8,9-methylenedioxy-2',2'-dimethylpyrano-[5',6':4,3]-6a-prenyl-[6aS,11aS]-pterocarpan (spirotropin A), 2-hydroxy-8,9-methylenedioxy-2',2'-dimethy1-3',4'-dihydropyrano-[5',6':4,3]-6a-prenyl-(6aS,11aS]-pterocarpan (spirotropin B), and 5,7-dihydroxy-6.8-dipreny1-2 ''''.2 ''''-dimethylpyrano[5 '''',6 '''': 3',4]-isoflavone (spirotropone). In addition, 10 known compounds, trans-oxyresveratrol, trans-resveratrol, piceatannol, daidzein, genistein, isoprunetin, lupeol, latifolol, gnetin D and gnetin E, were also isolated. These compounds were evaluated for their antifungal activity and their cytotoxicity, and their structures were established by 1D and 2D NMR, HRMS, CD and optical rotation measurements. (C) 2011 Elsevier Ltd. All rights reserved.

Screening of Polyalthia longifolia and Aloe vera for their phytoextractability of heavy metals in tropical soil of the Niger Delta

The work focuses on the screening of Polyalthia longifolia and Aloe vera for their phytoextractability of heavy metal in soil of the Niger Delta. 5kg of soil was polluted with 100 mg of Zn, Fe and Pb each replicated 9 times. Each set was separated into 3 subgroups. The subgroups were phytoextracted with Polyalthia longifolia and Aloe vera alongside a control (no phytoextraction) respectively. After 12 weeks, the concentration of Lead, Iron and Zinc in soils, roots and shoots was determined. Results showed that the two plants have phytoextraction ability with reductions in Zn, Fe, and Pb in the phytoextraction soil . Metal transfer factor was PB: Aloe vera (0.881) > P. longifolia (0.315); Zn: P. longifolia (0.614) > Aloe vera (0.606); Fe: Aloe vera (0.812) > P. longifolia (0.774). Translocation factors for the two plants were in the order: Zn: P. longifolia (0.79) > Aloe vera (0.36); Fe: P. longifolia (0.63) > Aloe vera (0.05); Pb: P. longifolia (0.57) > Aloe vera (0.23). Since the translocation factors were < 1, the plants can be classified as non- hyperaccumulators for these metals.

Lectotypification and synonymy in Hortia (Rutaceae)

During taxonomic revision of the genus Hortia Vandelli (Rutaceae), it was necessary to lectotypify the name H. megaphylla Taubert because of the destruction of the holotype at B (luring World War II. This name is also formally synonymized under H. longifolia Spruce ex Engler. The author attribution is changed for H. longifolia Spruce ex Engler, crediting Spruce rather than Bentham.

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.

Antiproliferative Effect of Benzophenones and their Influence on Cathepsin Activity

The antiproliferative activity of two prenylated benzophenones isolated from Rheedia brasiliensis. the tri-prenylated garciniaphenone and the tetraprenylated benzophenone 7-epiclusianone, was investigated against human cancer cell lines. The antiproliferative activity on melanoma (UACC-62), breast (MCF-7), drug-resistant breast (NCI-ADR), lung/non-small cells (NCI460), ovarian (OVCAR 03), prostate (PC03), kidney (786-0), lung (NCI-460) and tongue (CRL-1624 and CRL-1623) cancer cells was determined using spectrophotometric quantification of the cellular protein content. The effect of these benzophenones on the activity of cathepsins B and G was also investigated. Garciniaphenone displayed cytostatic activity in all cell lines, whereas 7-epiclusianone showed a dose-dependent cytotoxic effect. The IC(50) values for cell proliferation revealed that 7-epiclusianone is more active than garciniaphenone against most of the cell lines. Furthermore, the antiproliferative effects demonstrated by garciniaphenone and 7-epiclusianone were related to their cathepsin inhibiting properties. In conclusion, 7-epiclusianone is a promising naturally occurring agent which displays multiple inhibitory effects which may be working in concert to inhibit cancer cell proliferation in vitro. The putative pathway by which 7-epiclusianone affects cancer cell development may involve cathepsin inhibition. Copyright (C) 2009 John Wiley & Sons, Ltd.

Effects of 7-Epiclusianone on Streptococcus mutans and Caries Development in Rats

The aim of this study was to evaluate the effects of 7-epiclusianone (7-epi) on specific virulence attributes of Streptococcus mutans in vitro and on development of dental caries in vivo. 7-Epi was obtained and purified from fruits of Rheedia brasiliensis. We investigated its influence on surface-adsorbed glucosyltransferase (Gtf) B activity, acid production, and viability of S. mutans in biofilms, as well as on caries development using a rodent model. 7-Epi (100 mu g/mL) significantly reduced the activity of surface-adsorbed GtfB (up to 48.0 +/- 1.8 of inhibition at 100 mu g/mL) and glyco-lytic pH-drop by S. mutans in biofilms (125 and 250 mu g/mL) (vs. vehicle control, p < 0.05). In contrast, the test compound did not significantly affect the bacterial viability when compared to vehicle control (15% ethanol, p > 0.05). Wistar rats treated topically with 7-epi (twice daily, 60-s exposure) showed significantly smaller number of and less severe smooth-and sulcal-surface carious lesions (p < 0.05), without reducing the S. mutans viable population from the animals` dental biofilms. In conclusion, the natural compound 7-epiclusianone may be a potentially novel pharmacological agent to prevent and control dental caries disease.