In vitro antioxidant activity and qualitative phytochemical analysis of two Vismia (Hypericaceae) species collected in Los Andes, Venezuela / Actividad antioxidante in vitro y análisis fitoquímico cualitativo de dos especies de Vismia (Hypericaceae) recolectadas en Los Andes, Venezuela

Abstract:Vismia genus is distributed mainly in tropical and subtropical regions of Central, South America and some areas of Africa. According to previous investigations, antioxidant potential of Vismia species might be related to anthrones, anthraquinones, flavonoids and phenol derivatives biosynthesized by these plants. In this investigation, phytochemical screening of Vismia baccifera (VB) from Mérida-Venezuela and Vismia macrophylla (VM) from Táchira-Venezuela methanolic extracts, carried out using various chemical assays, revealed an abundant presence of anthraquinones in both species analyzed. Glycosides were also present while flavones and dehydroflavones were observed abundantly in VB but moderated in VM. Triterpenes were also detected and steroids showed to be abundant in VM but moderate in VB. On the other hand, antioxidant capacity measured by the DPPH assay showed that VM possesses a stronger antioxidant activity than VB with IC50 5.50 µg mL-1. Phenol and flavonoid assays carried out by Folin-Ciocalteu and colorimetric test also revealed that methanol extracts of both species contain high concentrations of these metabolites. A relationship between the antioxidant activity, total phenol and flavonoids content of the extracts analyzed was demonstrated in this investigation since those samples with higher phenolic concentrations showed likewise higher antioxidant activity. Rev. Biol. Trop. 64 (4): 1431-1439. Epub 2016 December 01.

Resumen:El género Vismia esta distribuido principalmente en las regiones tropicales y subtropicales de Centro, Sur América y algunas zonas de África. De acuerdo a reportes previos, el potencial antioxidante de las especies de Vismia puede estar relacionado con antronas, antraquinonas, flavonoides y derivados fenólicos biosintetizados por estas plantas. En la presente investigación, el tamizaje fitoquímico de los extractos metanólicos de Vismia baccifera (VB) de Mérida-Venezuela y Vismia macrophylla (VM) de Táchira-Venezuela realizado con diferentes ensayos químicos reveló abundante presencia de antraquinonas en ambas especies analizadas. Glucósidos también estuvieron presentes mientras que flavonas y dehidroflavonas fueron observados abundantemente en VB pero con presencia moderada en VM. Triterpenos y esteroides también fueron detectados mostrando ser abundantes en VM y moderados en VB. Por otro lado, la actividad antioxidante determinada por el método DPPH reveló que VM posee actividad antioxidante más fuerte que VB con un IC50 de 5.50 µg mL-1. El ensayo del contenido de fenoles y flavonoides realizado con los métodos de Folin-Ciocalteu y test colorimétrico también demostró que los extractos metanólicos de ambas especies contienen altas concentraciones de estos metabolitos. En este estudio se observó una relación entre la actividad antioxidante, el contenido de fenoles y de flavonoides en los extractos analizados ya que las muestras que presentaron concentraciones más altas de fenoles y flavonoides también mostraron una mayor actividad antioxidante.

Composición química y evaluación de la actividad antifúngica del aceite esencial de corteza de Vismia baccifera var. dealbata / Chemical composition and evaluation of anti-fungal activity of essential oil from Vismia baccifera var. dealbata bark

El objetivo de este trabajo fue evaluar la susceptibilidad de levaduras del género Candida y el Complejo Cryptococcus neoformans al aceite esencial de Vismia baccifera var. dealbata. El aceite, procedente de Chiguará, estado Mérida-Venezuela, fue analizado por CG/ EM logrando la identificación de trece componentes, que constituyeron el 97,7% de la mezcla; tres de ellos se apreciaron como productos mayoritarios, representando el 70,4% de la totalidad (Óxido de cariofileno 31,4%, β-cariofileno 26,4% y α-zingibireno 12,6%). El ensayo de actividad antifúngica mostró que dicho aceite inhibió el crecimiento de varias cepas de los géneros Candida y el Complejo C. neoformans, evaluadas cualitativamente por difusión en agar con disco a una concentración de 1.000 μg/mL; se observaron halos de inhibición entre 8 y 12 mm, exhibiendo valores de CMI entre 1,6 y 1.000 μg/mL en el ensayo cuantitativo por el método “Spot on a lawn”. Los datos obtenidos fueron sometidos a análisis de varianza y la prueba de Tukey, obteniéndose una actividad inhibitoria relevante contra Candida krusei. Este estudio constituye el primer reporte, tanto de la composición química como de evaluación antifúngica del aceite esencial extraído a partir de especies del género Vismia.

The purpose of this study was to evaluate the susceptibility of Candida genus yeasts and the Cryptococcus neoformans Complex to essential oil from Vismia baccifera var. dealbata. This oil, obtained at Chiguará, Mérida State, was analyzed by GC/MS, which identified thirteen components that constituted 97.7% of the mixture; three of them were established as majority products, representing 70.4% of the total: (cariophyllene oxide 31.4%, β-cariophyllene 26.4%, and α-zingibirene 12.6%). The anti-fungal assay showed that this oil inhibited the growth of several Candida genus strains and of the C. neoformans Complex, qualitatively evaluated by agar disk diffusion at a 1,000 μg/ mL concentration; inhibition halos of a between 8 to 12 mm diameter were observed, showing MIC values between 1.6 and 1,000 μg/mL in the “Spot on a lawn” quantitative assay. The data obtained were submitted to ANOVA and Tukey’s test, demonstrating a relevant inhibitory activity against Candida krusei. This study constitutes the first report, both of the chemical composition and of the anti-fungal evaluation, of the essential oil extracted from Vismia genus species.

Revisión bibliográfica sobre la composición química y actividades farmacológicas del género Vismia (Guttiferae) / A review on the chemical composition and pharmacological activities of Vismia genus (Guttiferae)

Vismia genus is an important source of natural medicinal products, thus, information collected in this review is an attempt to cover the most recent developments in the ethnopharmacology, pharmacology and phytochemistry of this genus. Anthraquinones and other quinonoid derivates, terpenoids and volatile constituents have been reported as the major constituents isolated from different Vismia species. On the other hand, pharmacological studies carried out to date have revealed the variety of anti-plasmodium, antioxidant, antimicrobial and antifungical properties of extracts and pure isolated compounds of the different species tested. The information summarized in this paper intends to serve as a reference tool to practitioners in the fields of etnopharmacology and chemistry of natural products.

El género Vismia es una fuente importante de productos naturales medicinales, es por esto que la información reunida en la presente revisión cubre los estudios más recientes en la etnofarmacología, farmacología y fitoquímica de este género. Antraquinonas y otros derivados quinoides, terpenos y constituyentes volátiles han sido reportados como los compuestos mayormente aislados de las diferentes especies de Vismia. Por otro lado, los estudios farmacológicos realizados hasta los momentos muestran las diversas propiedades antiplasmodicas, antioxidantes, antimicrobianas y antifúngicas que presentan tanto los extractos como los compuestos puros aislados de las diferentes especies ensayadas. La información resumida en este documento intenta servir de material de apoyo para investigadores en los campos de la etnofarmacologia y la química de productos naturales.

NMR elucidation and crystal structure analysis of 1-hydroxy-3, 6-dimethoxy-8-methyl-9h-xanthen-9-one (lichexanthone) isolated from Vismia baccifera (Guttiferae) / Elucidación por RMN y análisis de la estructura cristalina de 1-hidroxi-3,6-dimetox1-8-methil-9h-xanten-9-ona (lichexanthone)

In the present investigation the structural analysis of 1-hydroxy-3,6-dimethoxy-8-methyl-9h-xanthen-9-one (lichexanthone) isolated from Vismia baccifera var. dealbata collected in Mérida-Venezuela, was established by NMR (1H and 13C), mass spectrometry and single crystal X-ray diffraction. Lichexanthone crystallizes in the monoclinic system, space group P21/c (No 14) with unit cell parameters a = 11.6405(5) Å; b = 7.5444(3) Å; c = 15.2341(6) Å; = 102.280(1)°; V = 1307.26(9) Å3; Z = 4. The structure refinement converged to R = 0.0397, wR2 = 0.1076, S = 1.04. Lichexanthone had been isolated before from Parmotrema sp and Ruprechtia tangarana (Polygonaceae). However, to the best of our knowledge, this is the first report of this compound obtained from V. baccifera var. dealbata (Guttiferae).

En la presente investigación el análisis estructural de 1-hidroxi-3,6-dimetoxi-8-metil-9h-xanten-9-ona (lichexanthone) aislada de Vismia baccifera var. dealbata colectada en Mérida-Venezuela, fue determinado por RMN (1H y 13C), espectrometría de masas y difracción de rayos X. La lichexanthona cristaliza en un sistema monoclínico con un grupo espacial P21/c (No 14) y parámetros de celda de a = 11.6405 (5) Å; b = 7.5444 (3) Å; c = 15.2341 (6) Å; = 102.280(1)°; V = 1307.26(9) Å3; Z = 4. El refinamiento de la estructura convergió a los valores de R = 0.0397, wR2 = 0.1076, S = 1.04. La lichexanthona ha sido aislada de Parmotrema sp y Ruprechtia tangarana (Polygonaceae). Sin embargo, para nuestro conocimiento, esta es la primera vez que se reporta el aislamiento de este compuesto en la especie V. baccifera var. dealbata (Guttiferae).

Banco de sementes de uma floresta secundária amazônica dominada por Vismia

The floristic compostion of a secondary forest dominated by Vismia in central Amazonia was studied and compared to the composition of the seed bank in the soil. The area contained 20 tree species, with Vismia being the dominant genus in importance value, relative density, and basal area. The seed bank collected from the area exhibited 17 species that germinated, all pioneers, of which half were herbaceous and half were woody. In general, the composition of the seed bank was characteristic of successional stages with a strong influence from the abandoned pasture, the presence of pioneer species, and a large number of herbs and grasses. Two genera, Goupia and Laetia, were absent from the bank, although adult individuals were in the canopy. The three genera over-represented in the seed bank, relative to the canopy, were Cecropia, Bellucia and Trema, whose seeds probably arrived after the development of the canopy of Vismia. In field plots where the canopy was removed, germination mirrored the composition of the established vegetation in the area without the presence of new species exclusive to the seed bank. Thus, the return to primary forest will be delayed and depend on the proximity of seed sources as well as the presence of dispersers to contribute a diverse seed rain.

A composição florística de uma floresta secundária dominada por Vismia na Amazônia central foi estudada e comparada de acordo com sua composição ao banco de sementes no solo. A área apresentou um total de 20 espécies arbóreas, sendo Vismia o gênero dominante em indíce de valor de importância, densidade relativa e área basal. O banco de sementes coletado na área apresentou germinação de apenas 17 espécies, todas pioneiras, entre as quais metade foi de herbáceas e a outra metade de lenhosas. A composição do banco de sementes foi em geral característica de estágios sucessionais, com forte influência do histórico de pastagem, presença de espécies pioneiras e um elevado número de herbáceas e gramíneas. Os gêneros Goupia e Laetia estiveram ausentes no banco mesmo com indivíduos adultos representados no dossel. Os três gêneros com maior representação no banco de sementes em relação ao dossel foram Cecropia, Bellucia e Trema, os quais provavelmente germinaram de sementes chegadas depois do desenvolvimento do dossel de Vismia. As parcelas que tiveram o dossel removido refletiram muito bem a composição da vegetação estabelecida na área, onde sementes de espécies da floresta mais madura não germinaram. Desta forma, o retorno à floresta primária deverá ser um processo lento e dependente de fontes de sementes próximas, além da presença de dispersores capazes de contribuir com a chuva de sementes.