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Phytochemical Analysis and Bioactivity of Helicteres Baruensis Jacq

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Phytochemical Analysis and Bioactivity of Helicteres Baruensis Jacq Ingeniería Industrial. Año 12, Vol. VI, No. 22 97 Actualidad y Nuevas Tendencias ISSN: 1856-8327 e-ISSN: 2610-7813 Phytochemical analysis and bioactivity of Helicteres baruensis Jacq. (Sterculiaceae) Análisis fitoquímico y bioactividad de Helicteres baruensis Jacq. (Sterculiaceae) Haydelba D’Armas, Arneida Tarache, Gabriel Ordaz González, Maribel Quintero Palabras clave: Helicteres baruensis, bioactividad, hidrocarburos, alcaloides, terpenoides Key words: Helicteres baruensis, bioactivity, hydrocarbons, alkaloids, terpenoids ABSTRACT methylbutyl) phthalate, and bis(2-ethylhexyl) phthalate; fatty acid derivatives such as methyl Samples of Helicteres baruensis Jacq. aerial parts 9,12,15-octadecatrienoate and isopropyl were extracted with methanol, and then octadecanoate; terpenoids such as cyclic 1,2- methanol extract from the leaves was ethanediyl mercaptole (5α)-androstan-3-one, partitioned in petroleum ether and chloroform. 4,8,12,16-tetramethylheptadecan-4-olide, Alkaloids, sterols and polyphenols were the 5,6,7,7a-tetrahydro-2(4H)-benzofuranone, 2- secondary metabolite families detected in methylacetophenone, γ-terpinene, and 6,10,14- crude extracts and primary fractions of leaves trimethyl-2-pentadecanone; and other extract. Fruit and flower extracts exhibited constituents such as 2,4-dimethyl-9- lethal or toxic activity against A. salina, while oxadodecan-4-ol, triphenyl phosphate, and 6- leaf and stem extracts were not toxic against methoxi-2-ethoxi-7-methyl-7H-purine. From this organism at concentrations lower than the chloroform fraction of leaves, a compound -1 1000 μg·mL . However, fractions of leaves containing steroidal nucleus was isolated, extract showed being active, which suggest which is possibly the phytosterol stigmasterol. antagonism among bioactive constituents. In This is the first report of constituents on antimicrobial assay, Gram (+) and Gram (-) Helicteres baruensis Jacq. leaves in the literature, microorganisms were not sensible to crude which confirms the potentiality of this plant to extracts, but they were sensible to fraction of biosynthesize several phytochemical families. leaves extract, which confirm antagonism of this bioactivity. In this sense, aerial parts of H. RESUMEN baruensis Jacq. could be a source of secondary metabolites with pharmaceutical properties. Se extrajeron muestras de partes aéreas de Additionally, analyses by GC-MS of some Helicteres baruensis Jacq. con metanol, y luego el fractions obtained from chromatographic extracto de metanol de las hojas se repartió en separations of petroleum ether fraction from éter de petróleo y cloroformo. Alcaloides, leaves allowed identifying several metabolites, esteroles y polifenoles fueron las familias de among them some lineal saturated and metabolitos secundarios detectados en unsaturated hydrocarbons such as extractos crudos y fracciones primarias de hexatriacontane, (E)-7-tetradecene, (Z)-3- extracto de hojas. Los extractos de frutas y hexadecene, and (E)-3-octadecene; phthalate flores exhibieron actividad letal o tóxica contra derivatives such as dibutyl phthalate, bis(2- A. salina, mientras que los extractos de hojas y D’Armas et al., Phytochemical analysis and bioactivity of Helicteres baruensis Jacq. …, p. 97-116 Ingeniería Industrial. Año 12, Vol. VI, No. 22 98 Actualidad y Nuevas Tendencias ISSN: 1856-8327 e-ISSN: 2610-7813 tallos no fueron tóxicos contra este organismo -3 -hexadeceno y (E) -3-octadeceno; derivados a concentraciones inferiores a 1000 μg · mL-1. de ftalato tales como ftalato de dibutilo, ftalato Sin embargo, las fracciones de extracto de hojas de bis (2-metilbutilo) y ftalato de bis (2- mostraron ser activas, lo que sugiere etilhexilo); derivados de ácidos grasos tales antagonismo entre los componentes bioactivos. como 9,12,15-octadecatrienoato de metilo y En el ensayo antimicrobiano, los octadecanoato de isopropilo; terpenoides tales microorganismos Gram (+) y Gram (-) no como 1,2-etanodiil mercaptole (5α) -androstan- fueron sensibles a los extractos crudos, pero sí 3-ona cíclico, 4,8,12,16-tetrametilheptadecan-4- a la fracción de extracto de hojas, lo que olida, 5,6,7,7a-tetrahidro-2 (4H) - confirma el antagonismo de esta bioactividad. benzofuranona, 2-metilacetofenona, γ- En este sentido, partes aéreas de H. baruensis terpinene y 6,10,14-trimetil-2-pentadecanona; y Jacq. podría ser una fuente de metabolitos otros constituyentes tales como 2,4-dimetil-9- secundarios con propiedades farmacéuticas. oxadodecan-4-ol, trifenilfosfano y 6-metoxi-2- Además, los análisis por GC-MS de algunas etoxi-7-metil-7H-purina. De la fracción de fracciones obtenidas de separaciones cloroformo de las hojas, se aisló un compuesto cromatográficas de la fracción de éter de que contenía núcleo esteroideo, que petróleo de las hojas permitieron identificar posiblemente sea el estigmasterol de fitosterol. varios metabolitos, entre ellos algunos Este es el primer informe de constituyentes hidrocarburos lineales saturados e insaturados sobre Helicteres baruensis Jacq. deja en la como el hexatriacontano, (E) -7-tetradeceno, (Z) literatura, que confirma la potencialidad de esta planta para biosintetizar varias familias INTRODUCTION fitoquímicas. The genus Helicteres belongs to distributed in Venezuela (Rondón & Sterculiaceae family, which has shown being Cumana, 2006; Lárez, 2007; Rondón & a source of secondary metabolites with Cumana-Campos, 2007; Díaz & Febres, biological properties (Al Muqarrabun & 2009; Díaz & Carrasco, 2014; Álvarez & Ahmat, 2015). This genus comprises Leite, 2016). However, they have been little around 60 species (Rondón & Cumana- studied chemically. Campos, 2007; Golberg, 2009), but much of The aim of this study was to evaluate the the phytochemical and bioactivity analysis secondary metabolite profile and appear to be focused on H. isora Linn bioactivity of extracts of Helicteres baruensis (Kumar & Kumar, 2014; Akshatha et al., Jacq. (Sterculiaceae) aerial parts collected in 2015; Manke et al., 2015; Pandey et al., 2015; Sucre state, Venezuela, through Chandirasegaran et al., 2016; Dayal et al., identification of some constituents 2017; Kanthale & Biradar, 2017). The shrubs responsible for that bioactivity, H. guazumifolia Kunth and H. baruensis Jacq. contributing to phytochemical knowledge are the species more abundant in some of this specie. regions of America, and are widely D’Armas et al., Phytochemical analysis and bioactivity of Helicteres baruensis Jacq. …, p. 97-116 Ingeniería Industrial. Año 12, Vol. VI, No. 22 99 Actualidad y Nuevas Tendencias ISSN: 1856-8327 e-ISSN: 2610-7813 METODOLOGY Sampling ether fraction-PEF and chloroform fraction- Sample of H. baruensis Jacq. was collected in CF). Guaracayal area, between Cumaná city and Phytochemical screening Marigüitar sector (latitude and longitude The phytochemicals screening of plants coordinates: 10.45397 and -64.1825638), was performed as per well-established Sucre state, Venezuela. Taxonomic protocols (Domínguez, 1973; Marcano & identification was realized in the Hasegawa, 2002). Reagents used were: herbarium “Isidro Ramón Bermúdez Dragendorff (bismuth nitrate in nitric acid Romero” of Biology Department of and aqueous potassium iodine) for Universidad de Oriente, Sucre Campus, alkaloids, Liebermann-Burchard (acetic Venezuela. anhydride and chloroform with Extracts and first fractions concentrated sulfuric acid) for sterols and Each botanical part (leaves, fruits, stems, triterpenoids, Baljet (picric acid in ethanol and flowers) was separated from others, and aqueous sodium hydroxide) for pulverized and extracted with methanol sesquiterpenlactones; aqueous ferric (puriss. p.a., Fluka Chemie, Seelze, chloride for polyphenols, gelatin for Germany). In each case, solvent was tannins, and Shinoda (magnesium and evaporated in a rotary evaporator concentrated hydrochloric acid) for Heidolph (~11 mbar, 40 °C), for obtaining flavonoids. crude extracts (ME). Afterwards, these Brine shrimp (Artemia salina) lethality extracts were solubilized in assay methanol/distillated water (9:1 in volume) This bioassay was used to detect possible and fractionated with petroleum ether pharmacological properties of extracts. (Class 1A, Fisher Chemical, Fair Lawn, Method described by Meyer et al. (1982) New Jersey, USA). Then, aqueous residues was followed with some modifications. were extracted with pure chloroform Solution of 10,000 μg·mL-1 of each extract (Fluka Chemie, Seelze, Germany), and the and fraction was prepared using a mix of new aqueous residues were discarded. dimethyl sulfide and sterile sea water (1:1 Anhydrous sodium sulfate (Fisher v/v). Then, dilutions of 1,000.00; 100.00; Chemical, Fair Lawn, New Jersey, USA) 1.00; 0.10; and 0.01 μg·mL-1 were prepared. was added in order to dry (~5 g/100 mL of The same solvent system and dilutions solvent) organic fractions in each case. were used as negative controls. Ten nauplii Subsequently, each solvent was of A. salina brine shrimp were put into concentrated under the same conditions to vials containing those solutions. Bioassay obtain crude primary fractions (petroleum was carried out by triplicate. Mortality quantification after 24 h and 48 h was used D’Armas et al., Phytochemical analysis and bioactivity of Helicteres baruensis Jacq. …, p. 97-116 Ingeniería Industrial. Año 12, Vol. VI, No. 22 100 Actualidad y Nuevas Tendencias ISSN: 1856-8327 e-ISSN: 2610-7813 to calculate median lethal concentration layer chromatography (TLC) was (LC50) according to Stephan (1977). performed on glass plates (20×20 cm2) Antibacterial
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