RESUMEN

Gallesia integrifolia, a notable species in the Atlantic Forest, has been traditionally employed in folk medicine for treating rheumatism, asthma, and worms. This study investigated the cellular antioxidant, antiproliferative, and anti-inflammatory activities of the essential oils (EOs) and crude extracts (CEs) from G. integrifolia flowers, fruits, and leaves. The chemical identification of EOs was performed by GC-MS and CEs by UHPLC-MS. Cellular antioxidant and anti-inflammatory activities were assessed through mouse macrophage cell culture. In addition, the antiproliferative potential was evaluated in gastric, colorectal, breast, and lung tumor cell lines and non-tumor VERO cells. EOs predominantly contained organosulfur compounds in flowers (96.29%), fruits (94.94%), and leaves (90.72%). We found the main compound is 2,2'-Disulfanediyldiethanethiol in the EOs of flowers (47.00%), leaves (41.82%), and fruits (44.39%). Phenolic compounds were identified in CEs. The EOs and CEs demonstrated potential against the tumor cell lines tested (GI50 between 51 and 230 µg/mL). The selectivity index values were greater than 1.0 (1.01 to 3.37), suggesting a relative safety profile. Moreover, the anti-inflammatory activity IC50 ranged from 36.00 to 268 µg/mL, and the cellular oxidation inhibition ranged from 69% to 82%. The results suggest that oils and extracts derived from G. integrifolia have potential for use in various industrial sectors.

Asunto(s)

Antioxidantes , Aceites Volátiles , Ratones , Animales , Chlorocebus aethiops , Antioxidantes/farmacología , Antioxidantes/análisis , Frutas , Células Vero , Hojas de la Planta/química , Flores/química , Antiinflamatorios/farmacología , Antiinflamatorios/análisis , Aceites Volátiles/química , Extractos Vegetales/química

RESUMEN

Three new tetrasulfated triterpene glycosides, chilensosides E (1), F (2), and G (3), have been isolated from the Far-Eastern sea cucumber Paracaudina chilensis (Caudinidae, Molpadida). The structures were established based on extensive analysis of 1D and 2D NMR spectra and confirmed by HR-ESI-MS data. The compounds differ in their carbohydrate chains, namely in the number of monosaccharide residues (five or six) and in the positions of sulfate groups. Chilensosides E (1) and F (2) are tetrasulfated pentaosides with the position of one of the sulfate groups at C-3 Glc3, and chilensoside G (3) is a tetrasulfated hexaoside. The biogenetic analysis of the glycosides of P. chilensis has revealed that the structures form a network due to the attachment of sulfate groups to almost all possible positions. The upper semi-chain is sulfated earlier in the biosynthetic process than the lower one. Noticeably, the presence of a sulfate group at C-3 Glc3-a terminal monosaccharide residue in the bottom semi-chain of compounds 1 and 2-excludes the possibility of this sugar chain's further elongation. Presumably, the processes of glycosylation and sulfation are concurrent biosynthetic stages. They can be shifted in time in relation to each other, which is a characteristic feature of the mosaic type of biosynthesis. The hemolytic action of compounds 1-3 against human erythrocytes and cytotoxic activities against five human cancer cell lines were tested. The compounds showed moderate hemolytic activity but were inactive against cancer cells, probably because of their structural peculiarities, such as the combination of positions of four sulfate groups.

Asunto(s)

Pepinos de Mar , Triterpenos , Animales , Humanos , Glicósidos/química , Pepinos de Mar/química , Triterpenos/química , Línea Celular Tumoral , Hemólisis , Sulfatos , Estructura Molecular

RESUMEN

Five new triterpene (4,4,14-trimethylsterol) di-, tri- and tetrasulfated pentaosides, chilensosides A (1), A1 (2), B (3), C (4), and D (5) were isolated from the Far-Eastern sea cucumber Paracaudina chilensis. The structures were established on the basis of extensive analysis of 1D and 2D NMR spectra and confirmed by HR-ESI-MS data. The structural variability of the glycosides concerned the pentasaccharide chains. Their architecture was characterized by the upper semi-chain consisting of three sugar units and the bottom semi-chain of two sugars. Carbohydrate chains of compounds 2-5 differed in the quantity and positions of sulfate groups. The interesting structural features of the glycosides were: the presence of two sulfate groups at C-4 and C-6 of the same glucose residue in the upper semi-chain of 1, 2, 4, and 5 and the sulfation at C-3 of terminal glucose residue in the bottom semi-chain of 4 that makes its further elongation impossible. Chilensoside D (5) was the sixth tetrasulfated glycoside found in sea cucumbers. The architecture of the sugar chains of chilensosides A-D (1-5), the positions of sulfation, the quantity of sulfate groups, as well as the aglycone structures, demonstrate their similarity to the glycosides of the representatives of the order Dendrochirotida, confirming the phylogenetic closeness of the orders Molpadida and Dendrochirotida. The cytotoxic activities of the compounds 1-5 against human erythrocytes and some cancer cell lines are presented. Disulfated chilensosides A1 (2) and B (3) and trisulfated chilensoside C (4) showed significant cytotoxic activity against human cancer cells.

Asunto(s)

Antineoplásicos , Neoplasias , Pepinos de Mar , Triterpenos , Animales , Humanos , Pepinos de Mar/química , Triterpenos/farmacología , Triterpenos/química , Filogenia , Glicósidos/farmacología , Glicósidos/química , Antineoplásicos/farmacología , Antineoplásicos/química , Azúcares , Sulfatos , Glucosa , Estructura Molecular

RESUMEN

Las saponinas son un tipo de metabolito secundario ampliamente estudiado por sus reconocidas propiedades biológicas. Gran parte de las investigaciones en fitoquímica están dirigidas a encontrar nuevas fuentes naturales de saponinas con aplicación medicinal. La quinua (Chenopodium quinoa Willd.) es una planta que ha alcanzado un valioso reconocimiento por ser una fuente de alimentos altamente nutritivos, así como una especie rica en saponinas triterpénicas contenidas, principalmente, en la cáscara de las semillas. A la fecha, se han identificado alrededor de 30 saponinas derivadas de la hederagenina y de los ácidos oleanólico, fitolacagénico y serjanico en la planta. El consumo del grano de quinua implica la remoción de la cáscara a fin de reducir su sabor amargo, la ingesta de niveles residuales de saponinas y la obtención de un subproducto rico en las mismas. Esta revisión, inicialmente, ofrece una contex-tualización general de las saponinas; posteriormente, recopila las características estructurales de las saponinas identificadas en la quinua, describe el efecto del procesamiento del grano en su contenido de saponinas y, finalmente, expone los efectos biológicos explorados con extractos de saponinas de quinua, los cuales pueden ser considerados como punto de partida en investigaciones futuras dirigidas al fortalecimiento de su uso en el campo farmacéutico y/o nutracéutico.

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Saponins are a type of secondary metabolite that have been widely studied due to their recognized biological properties. Most research into phytochemical has focused on finding new natural sources of saponins with medicinal interest. Quinoa ( Chenopodium quinoa) is a plant that has attained importance as a valuable source of food highly nutritious and rich in triterpenes saponins which are mainly in the outer husks of the seeds. Up to date, about 30 saponins derived from hederagenin, oleanolic acid, phytolaccagenic acid, and serjanic acid have been identified in the plant. Quinoa consumption involves removal of the husk to reduce its bitter taste, the ingestion of residual levels of saponins and obtaining a product rich in saponins. This revision, initially, offers a general contextualization of saponins, then, gathers the structural features of identified saponins in quinoa, describes the effect of the processing of the grain on its saponins content, and finally, exposes the biological properties explored with quinoa saponins extracts which might be considered as a starting point for future investigations aimed at strengthening of their use in the pharmaceutical and/or nutraceutical field.