A valepotriate-enriched fraction from Valeriana glechomifolia Meyer inhibits leukocytes migration and nociception in formalin test in rodents

Abstract Previous pre-clinical studies demonstrated that a valepotriates enriched fraction from Valeriana glechomifolia F.G. Mey., Caprifoliaceae, was effective against lipopolysaccharide from Escherichia coli (LPS)-induced sickness behavior as well as significantly decreased the cortical expression of pro inflammatory cytokines interleukin-1β and tumor necrosis factor-α. Other studies revealed anti-inflammatory properties of V. wallichii and V. amurensis. These findings open up new perspectives for Valeriana genus pharmacology, once it has been commonly associated to sedative and anxiolytic properties. The aim of this study was to investigate the antichemotactic, antinociptive and anti-inflammatory activities of a valepotriate-enriched fraction obtained from aerial and subterranean parts of V. glechomifolia submitted to supercritical CO2 extraction. The biological activities were assessed by means of formalin test in CF1 mice and Wistar rat's leukocytes migration assay (modified Boyden chamber method). Valepotriate-enriched fraction (1, 10 and 30 mg/kg, p.o.) inhibited the nociceptive behavior in the late phase of the formalin test in a dose dependent manner. The effect of the valepotriate-enriched fraction highest dose was comparable with that of diclofenac 50 mg/kg (p.o.). Valepotriate-enriched fraction (0.1-1 µg/ml) inhibited the leukocyte migration induced by lipopolysaccharide from Escherichia coli in a concentration dependent manner. This antichemotatic effect was comparable with that of indomethacin (0.1-1 µg/ml) and better than diclofenac (1 µg/ml) effect. This study demonstrated for the first time that a valepotriate-enriched fraction obtained from V. glechomifolia display a peripheral anti-inflammatory like activity.

Anti-inflammatory activity and chemical analysis of extracts from Trifolium riograndense

Abstract Aiming to investigate new therapeutic agents with fewer side effects, the number of studies about natural products has increased. Phenolic compounds comprise a well-studied class of abundant plant-derived compounds, whose anti-inflammatory activity has been described. Isoflavones are phenolic compounds that occur mainly in the Leguminosae family, and can be found in many species, such as Trifolium riograndense Burkart, Leguminosae (clover). In this study an HPLC method was used to determine and quantify four isoflavones (genistein, daidzein, formononetin, and biochanin A) in hydrolyzed leaf, flower, stolon, and root extracts of T. riograndense. In vivo anti-inflammatory activity was investigated using the rat paw edema method and in vitro chemotaxis model with a dry extract from the leaves, which had the highest amount of isoflavones. The major isoflavone found in all parts of the plant was formononetin. The chemotaxis assay revealed that the different concentrations (0.2-50 µg/ml) of the dry extract significantly inhibited neutrophil migration in a concentration-dependent manner (more than 90%). In the rat paw edema test, oral administration of clover extract 100 mg/kg was able to significantly inhibit the edema formation induced by carrageenan. In conclusion, chemical analyses showed that Trifolium riograndense is a plant rich in isoflavones and a new interesting option as isoflavone source. The results of the biological tests taken together show that the extract of T. riograndense has anti-inflammatory effect in rodents.

Essential oil composition and antichemotactic activity of stenachaenium benth species native to south Brazil / Composición y actividad antiquimiotaxica del aceite esencial de especies stenachaenium benth. nativas de sur de Brasil

Chemical composition of essential oils from four Stenachaenium species from South Brazil were established by gas chromatography coupled with mass spectrometry (GC/MS). The major compounds identified in the oil of S. megapotamicum were a coumarin derivative, 2H-1-benzopyran-2-one,7-(3-methylbutoxy) (24.0 percent), beta-bisabolene (12.8 percent) and thymol methyl ether (7.1 percent). The oil of S. adenanthum contained mainly pogostol (14.0 percent). S. riedelli oil showed significant presence of aliphatic compounds, with predominance of hexadecanoic acid in all samples (leaves, inflorescence and leaves collected during of inflorescence period). Hexadecanoic acid (23.8 percent) was also the main component in S. macrocephalum. Concerning antichemotactic activity, all the oil samples tested showed a significant leukocyte migration inhibition compared to chemotactic stimulant (lipopolysaccharide from Escherichia coli - LPS), at concentrations of 1 to 5 μg/mL, except for S. adenanthum. These results suggest that the essential oils of some Stenachaenium species could inhibit acute inflammatory process, because the migration of neutrophils occurs mainly in the early inflammatory process.

Se estableció la composición química de los aceites esenciales de cuatro especies de Stenachaenium del Sur de Brasil mediante cromatografía de gases acoplada a espectrometría de masas (CG/EM). Los compuestos mayoritarios identificados en el aceite de S. megapotamicum fueron: un derivado de cumarina, 2H-1-benzopiran-2-ona,7- (3-metilbutoxi) (24,0 por ciento), beta-bisaboleno (12,8 por ciento) y éter metil timol (7,1 por ciento). El aceite de S. adenanthum presentó principalmente pogostol (14,0 por ciento). El aceite de S. riedelli mostró una significativa presencia de compuestos alifáticos, con predominio de ácido hexadecanoico en todas las muestras (hojas, inflorescencias y hojas recolectadas durante del período de la inflorescencia). También el ácido hexadecanoico (23,8 por ciento) fue el principal componente en S. macrocephalum. En cuanto a la actividad antichemotaxica, todas las muestras de aceites ensayadas a concentraciones de 1 a 5 μg/ml, excepto para S. adenanthum, mostraron una inhibición significativa en la migración de leucocitos en comparación con agente quimiotáctico (lipopolisacárido de Escherichia coli – LPS). Estos resultados sugieren que los aceites esenciales provenientes de diferentes especies de Stenachaenium podrían inhibir procesos inflamatorios agudos, debido a que la migración de los neutrófilos se produce principalmente en el proceso inflamatorio temprano.

In vivo and in vitro anti-inflammatory activity of red clover Trifolium pratense dry extract

Red clover Trifolium pratense L., Fabaceae, contains four isoflavones, mainly formononetin and biochanin A, and in smaller concentrations, daidzein and genistein. These compounds have gained a lot interest due to its human health benefits, such as estrogenic and progestogenic activities, antioxidant, anti-cancer and others. The objective of this study was to determine in vivo and in vitro anti-inflammatory activity of red clover dry extract. The in vitro anti-inflammatory activity was assayed by the technique using the Boyden chamber method, evaluating the leukocyte migration inhibition (chemotaxis). The in vivo anti-inflammatory activity was tested by a carrageenan-induced rat paw edema test. The results of anti-inflammatory in vitro test showed that there was a significant inhibition of leukocyte migration at the concentrations of 100, 50, 25, 10 and 5 µg/mL of red clover dry extract, these doses resulted in 94.73, 95.39, 94.73, 84.68 and 78.75 percent of inhibition for each dose, respectively. The anti-inflammatory in vivo test resulted in a significant activity in both tested doses (100 and 50 mg/kg of red clover dry extract) and at each tested time. The average percentage of edema inhibition was 63.37 percent. The findings of this study suggested that red clover extract might be suitable for the treatment of inflammatory diseases.

Chemical composition of essential oils of Piper jacquemontianum and Piper variabile from Guatemala and bioactivity of the dichloromethane and methanol extracts

The essential oils from two native species from Guatemala were studied for their chemical composition and the dichloromethane and methanol extracts for their biological activity. A GC-MS analysis of the essential oil from Piper jacquemontianum Kunth, Piperaceae, showed 34 constituents, consisting mainly of linalool (69.4 percent), while Piper variabile C. DC. essential oil had 36 constituents, camphor (28.4 percent), camphene (16.6 percent) and limonene (13.9 percent) being the major components. Dichloromethane extracts of both species were cytotoxic against MCF-7, H-460 and SF-268 cell lines (<7 µg/mL). Dichloromethane extract of P. jacquemontianum was slightly active against bacteria (0.5 mg/mL), was active against promastigotes of Leishmania (20.4-61.0 µg/mL), and epimastigotes of Trypanosoma cruzi (51.9 µg/mL). The methanol extract of P. variabile showed antimalarial activity against Plasmodium falciparum F32 (4.5 µg/mL), and the dichloromethane extract against Leishmania (55.8-76.3 µg/mL) and T. cruzi (45.8 µg/mL). None of the extracts from the two species was active against Aedes aegypti larvae and Artemia salina nauplii.

Composição química e atividade antioxidante do óleo volátil de Eupatorium polystachyum DC / Chemical composition and antioxidant activity of the volatile oil from Eupatorium polystachyum DC

Os óleos voláteis das folhas e inflorescências de Eupatorium polystachyum DC. (Asteraceae), coletado no Rio Grande do Sul, Brasil, foram caracterizados por CG-EM e sua atividade antioxidante foi avaliada utilizando-se o método de DPPH. Foram obtidos rendimentos de 1,6 e 0,9 por cento de óleo em relação às folhas e inflorescências frescas, sendo identificados 34 compostos, correspondendo a 99,1 e 99,5 por cento do óleo volátil, respectivamente. Os óleos apresentaram exclusivamente compostos terpênicos, sendo que as folhas contêm grande quantidade de monoterpenos (66,4 por cento) enquanto que as inflorescências apresentaram quantidades equivalentes de mono e sesquiterpenos (51,8 e 47,7 por cento, respectivamente). As amostras apresentaram-se qualitativamente muito semelhantes sendo constituídas majoritariamente por: beta-pineno (14,7 e 9,8 por cento), beta-mirceno (15,3 e 10,8 por cento) e limoneno (22,8 e 20,5 por cento) entre os monoterpenos e beta-cariofileno (10,4 e 15,4 por cento), germacreno D (7,2 e 9,4 por cento) e biciclogermacreno (12,0 e 19,2 por cento) entre os sesquiterpenos. As diferenças entre as amostras foram basicamente quantitativas. Os óleos apresentaram atividade antioxidante pelo ensaio com DPPH por bioautografia na diluição de 1:10 em éter etílico (v/v).

The essential oil obtained from leaves and flowers of Eupatorium polystachyum DC. (Asteraceae) collected in Rio Grande do Sul State, Brazil, was characterized by GC-MS and its antioxidant activity was assessed by DPPH assay. The yield of essential oil, relative to fresh material, was 1.6 and 0.9 percent for leaves and flowers, respectively. Both oils are constituted exclusively by terpenic compounds. Leaf oil contains great quantity of monoterpenes (66.4 percent); on the other hand, inflorescence oil contains comparable quantities of mono- and sesquiterpenes (51.8 and 47.7 percent, respectively). The same compounds are majority in both oils: beta-pinene (14.7 and 9.8 percent), beta-myrcene (15.3 and 10.8 percent) and limonene (22.8 and 20.5 percent) among monoterpenes and beta-caryophyllene (10.4 and 15.4 percent), germacrene D (7.2 and 9.4 percent) and bicyclogermacrene (12.0 and 19.2 percent) among sesquiterpenes. The oils had antioxidant activity by DPPH assay in 1:10 dilution in ethyl ether (v/v).

Composição química do óleo volátil de Myrcianthes nativas da região sul do Brasil / Chemical composition of the volatile oils of native Myrcianthes species from South Brazil

O óleo essencial das folhas de Myrcianthes gigantea (Myrtaceae), coletadas no Rio Grande do Sul, foi obtido por hidrodestilação em Clevenger e analisado por CG/detector de ionização de chamas e CG/EM. Trinta e seis compostos foram identificados, totalizando 90,1 por cento do conteúdo do óleo. A composição do óleo demonstrou predominância de sesquiterpenos cíclicos, principalmente da via de ciclização do germacrano, apresentando espatulenol (28,8 por cento) e seu isômero, iso-espatulenol (9,5 por cento), como principais constituintes. A composição do óleo das folhas de M. cisplatensis e M. pungens, coletadas na mesma região, também foi analisada e comparada com estudos prévios reportados para estas espécies coletadas em outros países da América da Sul. O óleo essencial de M. cisplatensis apresentou um alto conteúdo de monoterpenos (56,3 por cento), especialmente das séries pinano e p-mentano, com três compostos majoritários: 1,8-cineol (29,8 por cento), limoneno (10,9 por cento) e a-pineno (8,9 por cento), sendo similar ao reportado. Para o óleo de M. pungens 36 compostos foram identificados, porém sem predomínio majoritário, onde b-cariofileno (10,1 por cento), foi o principal deles. O óleo desta espécie difere do relatado para exemplares coletados na Argentina, rico em monoterpenos, sugerindo uma possível ocorrência de quimiotipos.

The essential oil of Myrcianthes gigantea (Myrtaceae) leaves, which were collected in Rio Grande do Sul (Southern Brazil), was obtained by hydrodistillation in a Clevenger apparatus. The chemical investigation was performed by GC-FID and GC-MS. Thirty-six compounds were identified accounting for 90.1 percent of the oil content. The analyzed species was rich in cyclic sesquiterpenes, mainly those from the germecrane cyclization pathway, among them spathulenol (28.8 percent) and its isomer, iso-spathulenol (9.5 percent). Leaves of M. cisplatensis and M. pungens were also collected in the same region and the analysis of the oil composition was compared with those previously reported for collections from other countries in South America. M. cisplatensis oil showed a high content of monoterpenes (56.3 percent), specially from the p-mentane and pinane groups, with three major compounds: 1,8-cineole (29.8 percent), limonene (10.9 percent) and a-pinene (8.9 percent). These findings are in agreement with those reported previously. For M. pungens, thirty-six compounds were identified without a predominant component. b-caryophyllene (10.1 percent), with caryophyllane skeleton, was the main substance for this sample. For this species the oil composition was quite different from those related for two exemplars collected in Argentina, in which both oil were rich in monoterpenes. This result suggests the occurrence of chemotypes.