Evaluación de fenoles y limonoides en hojas de Cedrela odorata (Meliaceae) de una plantación experimental establecida en Tezonapa Veracruz, México / Evaluation of phenols and limonoids in leaves of Cedrela odorata (Meliaceae) from an experimental plantation established in Tezonapa Veracruz, Mexico

Cedrela odorata (Meliaceae) is a native timber tree to Tropical America, known for its high-quality wood, unfortunately, plantations of this species are severely attacked by Hypsipyla grandella. The attraction or repellency of this pest is related to secondary metabolites such as phenols and limonoids (triterpenes); therefore, it is important to study these compounds to understand the phytochemical phenomena behind this problem. With this aim, the concentration of total phenols and limonoides was evaluated in C. odorata leaves from a plantation established in Tezonapa Veracruz, Mexico. For this, a total of 66 tree leaves samples, from seven sites, were analyzed. Phenols and limonoids concentration showed significant differences not only among different provenances, but also among individual trees of the same site (Tukey, p≤0.05). Phenols concentration was variable and in the range from 49 to 223mg EAG/g e for total phenols, from 7 to 158mg EC/g e for flavonoids and from 4 to 104mg EC/g e for proanthocyanidins. Limonoids concentration was also variable, ranging between 227 and 748mg EL/g e. A major compound was found by High-Performance Liquid Chromatography with Ultraviolet Diode Array Detection (HPLC-UV-DAD), which corresponded to a flavonol kaempferol glycoside derivative; additionally, a flavanol catechin was also detected at low concentrations. GC-MS allowed the identification of the sesquiterpenoids β-elemene, E-caryophyllene, aromadendrene, α-humulene, γ-cadinene, D-germacrene, bicyclogermacrene, and the poly terpenoids D-α-tocopherol and β-sitosterol. Our results suggest that the evaluation of phenols may play an important role as a selection parameter for improvement and conservation programs, if they are complemented with conventional breeding practices.

Cedrela odorata (Meliaceae) es una especie forestal maderable nativa de América Tropical, conocida por la alta calidad de su madera. Plantaciones de esta especie son atacadas severamente por Hypsipyla grandella; la atracción o repelencia de la plaga está relacionada con metabolitos secundarios tipo fenoles y limonoides (triterpenos), por lo que el estudio de estos compuestos es importante para comprender algunos fenómenos fitoquímicos. Se evaluó la concentración de fenoles totales y limonoides en hojas de C. odorata (Meliaceae) de una plantación establecida en Tezonapa Veracruz México, se analizaron 66 individuos de siete procedencias. La concentración de fenoles y limonoides mostró diferencias significativas, no solo entre las procedencias sino también entre los árboles de una determinada procedencia (Tukey, p≤0.05). La concentración de fenoles totales varió de 49 a 223mg EAG/g e, los flavonoides de 7 a 158mg EC/g e y las proantocianidinas de 4 a 104mg EC/g e, mientras que en limonoides se obtuvieron valores de 227 a 748mg EL/g e. Mediante Cromatografía Líquida de Alta Resolución con detector UV-Arreglo de Diodos (HPLC-UV-DAD) se encontró un compuesto mayoritario que corresponde a un flavonol de tipo glicósido de Kaempferol y se identificó el flavanol catequina a bajas concentraciones. Por medio de Cromatografía de Gases-Espectrometría de Masas (CG-MS) se identificaron los sesquiterpenos β-elemeno, E-cariofileno, aromadendreno, humuleno, gama-cadineno, D-germacreno, biciclogermacreno y los poli terpenos Di-α-Tocoferol y β-sitosterol. Nuestros resultados sugieren que la evaluación de los fenoles puede desempeñar un papel importante como parámetro de selección en programas de mejora y conservación, si se complementan con las prácticas convencionales de mejoramiento genético.

Farmacognosia y farmacobotánica de especies pertenecientes a los géneros Esenbeckia y Raputia (Rutaceae) / Pharmacognosy and pharmacobotany of species of genera Esenbeckia and Raputia (Rutaceae)

Introducción: Esenbeckia y Raputia son géneros que pertenecen a la familia Rutaceae, que tienen información etnobotánica relevante, la cual deriva en estudios fitoquímicos que demuestran la cantidad de metabolitos secundarios que producen y su variabilidad molecular, lo cual muestra la importancia de estudios posteriores a estos géneros, que están distribuidos en Centroamérica y Suramérica, con el fín de tener información importante en la búsqueda de nuevos agentes terapéuticos para combatir enfermedades del tipo microbiano y afines. Objetivos: reunir y analizar información científica actualizada referente a los géneros Esenbeckia y Raputia como fuente natural de compuestos biológicamente activos, los cuales pueden llegar a ser utilizados en la medicina natural por su potencial farmacológico. Métodos: se incluyeron en el análisis artículos científicos y libros relacionados con los temas de composición química, usos tradicionales y evaluaciones farmacológicas, así como otros elementos de interés en la investigación de plantas medicinales. Resultados: la información analizada puede servir de base para el desarrollo de nuevas investigaciones que avalen el empleo en la terapéutica de productos fitoterápicos con elevada eficacia, seguridad y calidad. La revisión de los resultados en otros grupos de investigación permite establecer estrategias racionales de investigación científica, que contribuyan al uso de los recursos que se encuentran en universidades y centros de investigación y salud. Conclusiones: los elementos encontrados en la bibliografía consultada permiten asegurar que las especies pertenecientes a los géneros Esenbeckia y Raputia, pueden ser potencialmente empleadas en usos fitoterapéuticos, debido, entre otras cosas, al importante número de metabolitos secundarios identificados que poseen actividad farmacológica demostrada.

Introduction: Esenbeckia and Raputia are genera of the family Rutaceae about which relevant ethnobotanical information has been reported. Such data have been obtained from phytochemical studies showing the number of secondary metabolites they produce and their molecular variability. Hence the importance of later studies about these genera, which are distributed in Central and South America, with the purpose of obtaining important information useful in the search for new therapeutic agents against microbial and other related diseases. Objectives: collect and analyze updated scientific information about the genera Esenbeckia and Raputia as natural sources of biologically active compounds which may be used in natural medicine due to their pharmacological potential. Methods: the analysis included scientific papers and books dealing with the chemical composition, traditional uses and pharmacological evaluation of medicinal plants, as well as other topics of interest to natural medicine research. Results: the information analyzed may be the starting point for new research demonstrating the effectiveness, safety and quality of phytotherapy. Review of the results obtained by other research teams makes it possible to establish rational scientific research strategies, thus contributing to the use of resources from universities, research centers and health institutions. Conclusions: according to the information found in the literature consulted, species of genera Esenbeckia and Raputia may be used for phytotherapeutic purposes, due, among other reasons, to the considerable number of identified secondary metabolites with proven pharmacological activity.

Efeito de extratos orgânicos de Meliaceae sobre Bemisia tabaci (Gennadius) biótipo B em tomateiro / Effect of organic extracts from Meliaceae on Bemisia tabaci (Gennadius) B biotype in tomato plants

Avaliou-se o efeito de extratos orgânicos de Azadirachta indica. Melia azedarach. Toona ciliata e Trichilia pallida (Rutales: Meliaceae) sobre ovos e ninfas de Bemisia tabaci (Hemiptera: Aleyrodidae) biótipo B. Folhas e ramos foram secos, moídos e submetidos à extração (Soxhlet) em diclorometano e em etanol. Visando estabelecer uma concentração adequada para os estudos subsequentes, foram utilizados ovos oriundos de 40 adultos que foram mantidos por 24h em folíolos de tomateiro em gaiolas de voil. Após 9 dias, contou-se o número de ninfas e pulverizou-se o extrato de folhas de .. pallida em diclorometano em diferentes concentrações (0,32; 0,56; 1,0; 1,8 e 3,2%), além de água e acetona (controles). A mortalidade ninfal foi avaliada após sete dias. O experimento foi conduzido em delineamento inteiramente aleatorizado, com sete tratamentos e quatro repetições. Posteriormente, extratos em diclorometano e em etanol foram pulverizados sobre ovos na concentração selecionada (0,56%), em experimentos distintos para cada solvente. Após nove dias, avaliou-se a mortalidade dos ovos e fez-se nova pulverização, avaliando-se, após sete dias, a mortalidade ninfal. Os experimentos foram conduzidos em delineamento com blocos aleatorizados (10 tratamentos e quatro repetições). Os dados foram submetidos à análise de regressão, análise de variância e comparados pelo teste de Tukey. Observou-se maior rendimento dos extratos em etanol em relação aos extratos em diclorometano. Os extratos em diclorometano de folhas e de ramos das meliáceas afetaram significativamente a sobrevivência de ovos e ninfas da mosca-branca. Os extratos em etanol afetaram a fase de ninfa, mas não apresentaram atividade ovicida.

The effect of organic extracts from Azadirachta indica. Melia azedarach. Toona ciliata and Trichilia pallida (Rutales: Meliaceae) on eggs and nymphs of Bemisia tabaci (Hemiptera: Aleyrodidae) B biotype was assessed. Leaves and branches were dried, ground and submitted to extraction (Soxhlet) with dichloromethane and ethanol. To establish an adequate concentration for the subsequent tests, eggs were used originating from 40 adults maintained for 24h on tomato leaves in voile cages. After 9 days, the number of nymphs was determined and the dichloromethane extract from T. pallida leaves was sprayed at different concentrations (0.32, 0.56, 1.0, 1.8 and 3.2%); water and acetone were also used (controls). The nymphal mortality was evaluated after 7 days. An entirely randomized design was used, with 7 treatments and 4 replications. Afterwards, dichloromethane and ethanol extracts were sprayed on eggs at the selected concentration (0.56%), in different experiments. After 9 days, the egg mortality was evaluated and a new spraying was conducted to assess the nymphal mortality after 7 days. These experiments were conducted in a randomized block designed (10 treatments and 4 replications). The data was submitted to regression analysis, analysis of variance and compared by the Tukey test. A higher yield was observed for the ethanol extracts in relation to the dichloromethane extracts. The dichloromethane extracts from leaves and branches from meliaceas significantly affected the survival of the whitefly eggs and nymphs. The ethanol extracts affected the nymphal phase, but did not present ovicidal activity.

Trypanocidal activity of flavonoids and limonoids isolated from Myrsinaceae and Meliaceae active plant extracts / Atividade tripanocida de flavonoides e limonoides isolados de extratos ativos de plantas de Myrsinaceae e Meliaceae

The activity of crude extracts of three Rapanea species (Myrsinaceae) and Cipadessa fruticosa (Meliaceae) was evaluated in vitro against the trypomastigote forms of Trypanosoma cruzi. Thirty-three extracts from different organs of these species were assayed and eleven of them showed significant activity (lysis percent >50). The fractionation of an active extract from branches of R. lancifolia (99.5 percent) led to the isolation of two flavonoids: quercetin and taxifolin, which have weak trypanocidal activity. Additionally, one active extract from fruits of C. fruticosa (97.7 percent) afforded mexicanolide limonoids: cipadesin, mexicanolide, febrifugin and cipadesin A, that were slightly active on T. cruzi. Moreover, other two flavonoids (flavone and 7-methoxyflavone), previously assayed against T. cruzi, were isolated from the hexane extract from branches of C. fruticosa (100 percent). The results presented here suggest that the plants evaluated could be a source of new active compounds against T. cruzi.

A atividade de extratos brutos de três espécies de Rapanea (Myrsinaceae) e de Cipadessa fruticosa (Meliaceae) foi avaliada in vitro contra formas tripomastigotas de Trypanosoma cruzi. Foram obtidos 33 extratos de diferentes órgãos das espécies estudadas, sendo que onze deles apresentaram atividades significantes ( por cento de lise > 50) nos ensaios realizados. O fracionamento de um extrato ativo dos galhos de R. lancifolia (99,5 por cento) resultou no isolamento de dois flavonoides (quercetina e taxifolina), que apresentaram baixa atividade tripanocida. De um extrato ativo dos frutos de C. fruticosa (97,7 por cento) foram isolados os limonoides mexicanolídeos cipadesina, mexicanolídeo, febrifugina e cipadesina A, que foram moderadamente ativos sobre T. cruzi. Além disso, outros dois flavonoides (flavona e 7-metoxiflavona), previamente ensaiados contra T. cruzi, foram isolados do extrato hexânico dos galhos de C. fruticosa (100 por cento). Os resultados obtidos aqui sugerem que as plantas avaliadas podem constituir fontes de novas substâncias ativas sobre o T. cruzi.

ATIVIDADE BIOLÓGICA DE UM NOVO TRITERPENO ISOLADO DE Guarea cannata (MELIACEAE)

From the bark of Guarea carinata was isolated as main constituent a diacetilated triterpen (I) of protolimonoids type, derived from apo-tirucalol, that showed antifeedant activity in biological control of Urbanus acawoios(Lepidoptera,Hesperiidae).

Do cerne de Guarea carinata foi isolado como principal constituinte um triterpeno di-acetilado (I). do grupo dos protolimonóides, derivado do apo-tirucalol e que mostrou atividade no controle biológico das larvas de Urbanus acawoioa(WILLIAMS, R. C, 1926) (Lepidoptera Hesperiidac).

Estudo químico das sementes e casca da madeira de guarea trichilioides (meliaceae)

In this paper we related the identification and isolation of stearic, linolenic and palmitic acids and the isolation and structural determination of the 7-desacetoxy-7-hidroxyazadirone present in the hexan extract of the fruits of Guarea trichilioides. From the chloroform extrat of steam bark were isolated and identificated the antraquinones: chrysophanol and physcion.

Da casca da madeira de Guarea trichilioides foram isoladas e identificadas através de métodos espectrométricos as antraquinonas crisofanol e fisciona e das sementes o limonóide 7-desacetoxi-7-hidroxiazadirona. Da fração lipofílica das sementes foram ainda identificados por co-injeçao de padrões, através de cromatografia gasosa os ácidos esteárico, palmítico e linolênico.