Isolation of quinoline alkaloids from three Choisya species by high-speed countercurrent chromatography and the determination of their antioxidant capacity

Abstract Choisya ternata Kunth, C. ternata var. sundance Kunth and the hybrid Choisya 'Aztec-Pearl' are three related species belonging to the Rutaceae family. Ethanol extracts were prepared from the leaves of these three species and evaluated in relation to their antioxidant activity using in vitro and ex vivo models. The ethanol extracts belonging to the three species produced a very high antioxidant profile as evidenced by the DPPH radical scavenging activity, the determination of total phenolics and flavonoid equivalent. The generation of reactive species of oxygen in leukocytes stimulated with LPS was dramatically reduced when the three ethanol extracts were used. The alkaloids anhydroevoxine and choisyine were isolated from the ethanol extract of C. ternata using HEMWat (4:6:5:5) as the solvent system by means of high-speed countercurrent chromatography. This was the first time quinoline alkaloids were isolated from this species using HSCCC. These compounds were also assayed for their capacity to inhibit the generation of ROS in leukocytes stimulated by LPS and the results also suggested that they are reactive oxygenase inhibitors.

Diterpenes and a new benzaldehyde from the mangrove plant Rhizophora mangle

ABSTRACT This work describes the isolation, by high-speed counter-current chromatography, of the diterpenes manool, jhanol and steviol and the benzaldehyde p-oxy-2-ethylhexyl benzaldehyde from the stilt roots hexane extract of the mangrove plant Rhizophora mangle L., Rhizophoraceae. For this, a non-aqueous biphasic solvent system composed of hexane–acetonitrile–methanol 1:1:0.5 (v/v/v) was applied. As far as we know, only steviol was previously isolated in Rhizophoraceae and this is the first time that p-oxy-2-ethylhexyl benzaldehyde is reported.

In vitro and in vivo evaluation of efficacy and safety of photoprotective formulations containing antioxidant extracts

ABSTRACT Chronic exposure to solar radiation could contribute to premature skin aging and skin cancer. Skin presents its own antioxidant defense, however when defenses are out of balance, reactive oxygen species could damage biological structures. In the present work, an oil-in-water photoprotective emulsion was developed and Bauhinia microstachya var. massambabensis Vaz, Fabaceae, extracts at 1% (obtained by extraction with different solvents) were added to this emulsion. In vitro and in vivo efficacy and safety of the formulations were evaluated. Spectrophotometric methods and in vivo Colipa test were performed to evaluated efficacy of the formulations, through sun protection factor (SPF) determination and UVA protection factor assessment. To the in vitro safety assessment HET-CAM, CAM-TBS and Red Blood Cell tests were performed. Results showed that both extracts contributed to a higher in vivo photoprotection (SPF 18) when compared to the formulation without extract (SPF 13), this result could be attributed to the antioxidant activity of the plant extracts that act by capturing reactive oxygen species. Concerning safety, all formulations were considered non-irritant according to in vitro tests. Formulations containing extracts could be considered efficient and safe for cosmetic use since they presented higher sun protection factor and passed the toxicity tests.

Ethnopharmacological studies of Lippia origanoides

Lippia origanoides Kunth. Verbenaceae, is of great importance in the Brazilian traditional medicine. Because of it, this work had the purpose to contribute to the ethnopharmacological knowledge of L. origanoides through an ethnobotanical survey conducted within quilombola (maroon) communities of Oriximiná, Pará, Brazil. Among 254 plants cited in the survey, L. origanoides stood out among the ten most versatile species. The agreed main uses were to treat menstrual cramps, stomachache, and baby and postpartum colic. This could indicate a consensus of the informants to possible antispasmodic, anti-inflammatory and analgesic activities of L. origanoides.Therefore, anti-inflammatory and analgesic activities of L. origanoides extract (aerial parts) were assessed through thermal (hot plate) and chemical (formalin and acetic acid) models of nociception. A dose-dependent reduction in acetic acid-induced writhing was observed after treating mice with L. origanoides extract. The same extract also inhibited significantly formalin-induced licking response and proved to have a central antinociceptive effect, in the hot plate test. This work demonstrates that L. origanoides is used specially by quilombola women from Oriximiná for disorders of the genitourinary system and that biological activities of this species could contribute to these uses. Furthermore, it was also observed antispasmodic, analgesic and antimicrobial uses of other species of the genus Lippia (Goniostachyum section), rich in thymol and carvacrol.

Ethnopharmacological versus random plant selection methods for the evaluation of the antimycobacterial activity

The municipality of Oriximiná, Brazil, has 33 quilombola communities in remote areas, endowed with wide experience in the use of medicinal plants. An ethnobotanical survey was carried out in five of these communities. A free-listing method directed for the survey of species locally indicated against Tuberculosis and lung problems was also applied. Data were analyzed by quantitative techniques: saliency index and major use agreement. Thirty four informants related 254 ethnospecies. Among these, 43 were surveyed for possible antimycobacterial activity. As a result of those informations, ten species obtained from the ethnodirected approach (ETHNO) and eighteen species obtained from the random approach (RANDOM) were assayed against Mycobacterium tuberculosis by the microdilution method, using resazurin as an indicator of cell viability. The best results for antimycobacterial activity were obtained of some plants selected by the ethnopharmacological approach (50 percent ETHNO x 16,7 percent RANDOM). These results can be even more significant if we consider that the therapeutic success obtained among the quilombola practice is complex, being the use of some plants acting as fortifying agents, depurative, vomitory, purgative and bitter remedy, especially to infectious diseases, of great importance to the communities in the curing or recovering of health as a whole.

Anatomia e análise de óleo essencial das folhas de Hennecartia omphalandra J Poisson (Monimiaceae) / Anatomy and essential oil analysis of the leaves from Hennecartia omphalandra J Poisson (Monimiaceae)

Descreve-se a morfo-anatomia e a análise de óleo essencial das folhas de Hennecartia omphalandra J. Poisson (Monimiaceae), uma planta tóxica. A ocorrência de tricomas unicelulares, estômatos paracíticos; braquiesclereídes em grupos no pecíolo e na lâmina foliar, além de esclereídes vermiformes e ramiformes; sistema vascular em arco, com extremidades voltadas para o centro no pecíolo e na forma de arco atenuado na lâmina foliar, sendo o padrão de venação uma variação do tipo craspedódromo-semicraspedódromo, além de óleo essencial armazenado em idioblastos oleíferos não especializados no mesofilo, foram considerados caracteres importantes que podem auxiliar na sua morfo-diagnose. A análise do óleo essencial das folhas revelou a presença de monoterpenos, sesquiterpenos e álcoois sesquiterpênicos, sendo este o grupo mais significativo. Os componentes majoritários identificados foram β-felandreno (24,0 por cento), seguido por germacreno D (10,5 por cento), sabineno (9,3 por cento), biciclogermacreno (8,4 por cento) e β-elemeno (5,3 por cento).

This paper describes the morphological and anatomical aspects and the essential oil analysis of the leaves from Hennecartia omphalandra J. Poisson (Monimiaceae), a toxic plant. The presence of trichomes formed by a single cell, paracitic stomata, groups of braquisclereids in the petiole and leaf blade; vermiform and ramiform sclereids, vascular system in arc softly invaginated at ends in the petiole, and in a flat arc in the middle vein, being the venation pattern a variation of craspedodromous-semicraspedodromous type, and essential oil stored in oil idioblasts in the mesophyll were the most important characters that can help the morphological diagnosis. The analysis of essential oil of the leaves showed the presence of monoterpenes, as well as sesquiterpenes hydrocarbons and alcohols, being the latter the most significant group. The major identified compounds were β-phelandrene (24.0 percent), germacrene D (10.5 percent), sabinene (9.3 percent), bicyclogermacrene (8.4 percent) and β-elemene (5.3 percent).

Considerações anatômicas e análise de óleo essencial do hipanto e do fruto de Hennecartia omphalandra J. Poisson (Monimiaceae) / Anatomical considerations and essential oil analysis of the hypanthium and the fruit of Hennecartia omphalandra J. Poisson (Monimiaceae)

Descreve-se o estudo morfo-anatômico e a análise de óleo essencial do fruto de Hennecartia omphalandra J. Poisson (Monimiaceae), uma planta tóxica. A ocorrência de feixes recurrentes e de um anel descontínuo de braquiesclereides no hipanto; assim como a presença de células oleíferas no mesocarpo, de "idioesclereídes" formando o endocarpo e de células com espessamento parietal em rede, constituindo a testa da semente, foram considerados caracteres importantes que podem auxiliar na sua morfo-diagnose. A análise do óleo essencial dos frutos revelou a presença de monoterpenos, sesquiterpenos e álcoois sesquiterpênicos, sendo este o grupo mais significativo. Os componentes majoritários identificados foram o biciclogermacreno (19,6 por cento) e o β-felandreno (8,7 por cento), além do germacreno D (5,3 por cento), α-bulneseno (5,1 por cento) e valerianol (4,9 por cento).

The morphological and anatomical aspects of flower and fruit and the essential oil analysis of fruits of Hennecartia omphalandra J. Poisson (Monimiaceae), a toxic plant, are described in this paper. The presence of vascular recurrent bundles and of a ring of brachysclereids in the hypanthium; the oil cells in the mesocarp, the "idiosclereids" that constitutes the endocarp and cells with reticulated thick walls, shaping the seed coat were described as characters that may help in its diagnosis. The analysis of the essential oil of fruits showed the presence of monoterpenes, as well as sesquiterpenes hydrocarbons and alcohols, being the latter the most significant group. The major identified compounds were bicyclogermacrene (19.6 percent); β-felandrene (8.7 percent); germacrene D (5.3 percent); α - bulnesene (5.1 percent) and valerianol (4.9 percent).

Screening of Central and South American plant extracts for antimycobacterial activity by the Alamar Blue test / Triagem de extratos de plantas das Américas Central e do Sul para atividade antimicobacteriana pelo teste do Alamar Blue

Forty eight ethanolic crude extracts and fractions (hexane, dichloromethane, ethyl acetate and n-butanol) from ten Brazilian plants (Leguminosae, Monimiaceae and Verbenaceae), 1 from Costa Rica (Verbenaceae) and 1 from Argentina (Verbenaceae) were screened for anti-mycobacterium activity against Mycobacterium tuberculosis (ATCC-27294H37Rv), by the Alamar Blue test, at a fixed concentration of 100 µg/mL. Out of the forty eight, seven were active at this concentration, corresponding to Lantana trifolia (hexane and dichloromethane extracts from leaves), Vitex cooperi (methanol:water, 1:1 extract from barks), Lippia lacunosa (hexane and dichloromethane extracts from leaves) and Lippia rotundifolia (hexane and dichloromethane extracts from leaves), all from the Verbenaceae family.

Quarenta e oito extratos brutos etanólicos e frações (em hexano, diclorometano, acetato de etila e n-butanol) de dez plantas brasileiras pertencentes às famílias Leguminosae, Monimiaceae e Verbenaceae; uma da Costa Rica (Verbenaceae) e uma da Argentina (Verbenaceae) foram ensaiados para verificação da atividade anti-micobacteriana contra Mycobacterium tuberculosis (ATCC-27294H37Rv), pelo teste do Alamar Blue, a uma concentração fixa de 100 µg/mL. Dentre os quarenta e oito extratos e frações estudados, sete mostraram-se ativos na concentração ensaiada - frações em hexano e diclorometano de folhas de Lantana trifolia, extrato em metanol:água, 1:1 de cascas de Vitex cooperi, frações em hexano e diclorometano de folhas de Lippia lacunosa e de Lippia rotundifolia, sendoque todas essas plantas pertencem à família Verbenaceae.