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ABSTRACT An overview is provided on the cytogenetic of Chilean plants, highlighting information gathered from more than a century of work carried out by foreign and national researchers who have contributed to the study of native species. We briefly present the progress made to date and also emphasize some strategies that, in our opinion, could spur further advances in this second century of cytogenetic studies in Chilean plants.
RESUMEN Se presenta una visión general de la citogenética de plantas chilenas, destacando información recopilada durante más de un siglo de trabajo realizado por investigadores nacionales y extranjeros que han contribuido al estudio de las especies nativas. Presentamos brevemente los progresos realizados hasta la fecha y también destacamos algunas estrategias que, en nuestra opinión, podrían impulsar mayores avances en este segundo siglo de estudios citogenéticos en plantas chilenas.
RESUMO
Heliotropium taltalense is an endemic species of the northern coast of Chile and is used as folk medicine. The polyphenolic composition of the methanolic and aqueous extract of the endemic Chilean species was investigated using Ultrahigh-Performance Liquid Chromatography, Heated Electrospray Ionization and Mass Spectrometry (UHPLC-Orbitrap-HESI-MS). Fifty-three compounds were detected, mainly derivatives of benzoic acid, flavonoids, and some phenolic acids. Furthermore, five major compounds were isolated by column chromatography from the extract, including four flavonoids and one geranyl benzoic acid derivative, which showed vascular relaxation and were in part responsible for the activity of the extracts. Since aqueous extract of H. taltalense (83% ± 9%, 100 µg/mL) produced vascular relaxation through an endothelium-dependent mechanism in rat aorta, and the compounds rhamnocitrin (89% ± 7%; 10-4 M) and sakuranetin (80% ± 6%; 10-4 M) also caused vascular relaxation similar to the extracts of H. taltalense, these pure compounds are, to some extent, responsible for the vascular relaxation.
Assuntos
Aorta/metabolismo , Extratos Vegetais/química , Polifenóis , Vasodilatação/efeitos dos fármacos , Animais , Heliotropium/química , Masculino , Polifenóis/química , Polifenóis/farmacologia , Ratos , Ratos Sprague-DawleyRESUMO
The infusion of the desertic plant Nolana ramosissima I.M. Johnst showed vascular smooth muscle relaxation in rat aorta and the presence of several phenolic compounds, which were detected by high resolution UHPLC-Orbitrap-HESI-MS. In addition, five flavonoids were rapidly isolated from a methanolic extract using high-performance counter-current chromatography (HPCCC). The N. ramosissima extract showed endothelium-independent relaxation effect in rat aorta. Sixty-one compounds were detected in the infusion, mainly glycosylated flavonoids, flavanones and several oxylipins, suggesting that a synergistic effect between the compounds in the extracts could be responsible for the relaxation activity. Vascular activity experiments were done in isolated organ bath. In rat aorta, a nitric oxide inhibitor did not prevent the relaxation effects of the extract; however, a selective guanylyl cyclase inhibitor partially blunted this effect. The compound 5,3'-dihydroxy-4'7-dimethoxyflavone presented higher relaxation effect than 100 µg/mL of N. ramosissima extract. The extract and the isolated metabolites from N. ramosissima can show relaxation effects on rat aorta by a mechanism that is independent of the endothelium.
Assuntos
Aorta/fisiopatologia , Endotélio Vascular/fisiopatologia , Flavonoides , Extratos Vegetais/química , Solanaceae/química , Vasodilatação/efeitos dos fármacos , Animais , Feminino , Flavonoides/química , Flavonoides/isolamento & purificação , Flavonoides/farmacologia , Ratos , Ratos Sprague-DawleyRESUMO
Chilean Plants Cytogenetic Database (CPCD) is a resource available on line in electronic format, which provides a cytogenetics catalogue for continental and insular Chilean vascular plants. In this report, we made reference to the CPCD, discussing aspects on its coverage, features and usages. Currently, the database stores cytogenetic information for 247 species, 107 genera, and 55 families belonging to Pteridophyta, Pinophyta, and Magnoliophyta.
La Base de Datos Citogenéticos de Plantas Chilenas (CPCD) es un recurso disponible en formato electrónico en línea, que provee de un catálogo citogenético para plantas vasculares de Chile continental e insular. En esta comunicación hacemos referencia a la CPCD, discutiendo aspectos sobre su cobertura, rasgos y usos. Actualmente, la base de datos contiene información citogenética para 247 especies, 107 géneros y 55 familias pertenecientes a Pteridophyta, Pinophyta y Magnoliophyta.
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ABSTRACT High-resolution mass spectrometry is currently used to determine the mass of biologically active compounds in plants and UHPLC-Orbitrap is a relatively new technology that allows fast fingerprinting and metabolomics analysis. In this work, several phenolic compounds including eleven phenolic acids, two fatty acids, two chromones and fourteen flavones were rapidly identified in the methanolic extracts of aerial parts and flowers of the unique Chilean species Ophryosporus triangularis Meyen, Asteraceae, growing in the Atacama Desert by means of ultrahigh resolution liquid chromatography orbitrap MS analysis (UHPLC-PDA-OT-MS) for the first time. The UHPLC-MS fingerprint generated can be used for the authentication of this endemic species. The methanolic extracts of the aerial parts and flowers showed also antioxidant capacities (65.34 ± 1.32 and 52.41 ± 1.87 µg/ml in the DPPH assay, 184.88 ± 13.22 and 196.80 ± 13.28 µmol TE/g dry weight in the ferric reducing power assay and 56.17 ± 3.03 and 65.41 ± 1.96% in the superoxide anion scavenging assay, respectively).
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BACKGROUND: Azorella compacta (Apiaceae) is a native Chilean cushion shrub which produces a resin containing mulinane and azorellane diterpenoids. This plant has been used since pre-Colombian times to treat inflammation and dental neuralgias. In this work the first preparative fractionation of diterpenoids present in this plant by means of high-speed counter-current chromatography (HSCCC) was applied, and cytotoxic effects of the isolated compounds were evaluated for the first time against a panel of MCF7 cells. RESULTS: The major compounds isolated were identified by means of spectroscopy as azorellanol, 13α, 14α-dihydroxymulin-11-en-20-oic acid, mulinolic acid, mulin-11,13-dien-20-oic acid, 17-acetoxy-mulin-11,13-dien-20 oic acid, and 17-acetoxy-mulinic acid (compounds 7, 9-11 and 13, respectively), and four minor diterpenoids [7-deacetyl-azorellanol (6), 13-epi-azorellanol, 7-acetoxy-mulin-9,12-diene, and 17-acetoxy-mulin-11,13-dien-20-oic acid (compounds 4, 8 and 12)], together with three new minor diterpenoids: 13ß,14ß-dihydroxymulin-11-en-20-oic acid (1), 13-epiazorellanone (2) and 13-epi-7-deacetyl-azorellanol (3) were identified. Besides, compounds 4, 6, 7, 8 and 11 displayed good cytotoxic activity (less than 50% cell viability at 100 µM). Among them, compound 7, an acetylated azorellane, was the most active. CONCLUSIONS: HSCCC allowed the isolation of 13 diterpenoids present in A. compacta. Three compounds are reported for the first time. Isolated azorellanes are more potent cytotoxic agents than are mulinanes. © 2015 Society of Chemical Industry.
Assuntos
Antineoplásicos Fitogênicos/farmacologia , Apiaceae/química , Distribuição Contracorrente/métodos , Diterpenos/química , Diterpenos/farmacologia , Plantas Medicinais/química , Antineoplásicos Fitogênicos/administração & dosagem , Antineoplásicos Fitogênicos/química , Neoplasias da Mama , Chile , Diterpenos/administração & dosagem , Relação Dose-Resposta a Droga , Feminino , Humanos , Células MCF-7 , Estrutura MolecularRESUMO
The antioxidant features, polyphenolic composition and chromatographic fingerprints of the aerial parts from three Chilean endemic plants from the Paposo Valley located on the cost of the Atacama Desert were investigated for the first time using high pressure liquid chromatography coupled with photodiode array detector and electrospray ionization mass analysis (HPLC-PDA-ESI-MS) and spectroscopic methods. The phenolic fingerprints obtained for the plants were compared and correlated with the antioxidant capacities measured by the bleaching of the DPPH radical, the ferric reducing antioxidant power (FRAP) and quantification of the total content of phenolics and flavonoids measured by spectroscopic methods. Thirty phenolics were identified for the first time for these species, mostly phenolic acids, flavanones, flavonols and some of their glycoside derivatives, together with three saturated fatty acids (stearic, palmitic and arachidic acids). Nolana ramosissima showed the highest antioxidant activity (26.35 ± 1.02 µg/mL, 116.07 ± 3.42 µM Trolox equivalents/g dry weight and 81.23% ± 3.77% of inhibition in the DPPH, FRAP and scavenging activity (SA) assays, respectively), followed by N. aplocaryoides (85.19 ± 1.64 µg/mL, 65.87 ± 2.33 µM TE/g DW and 53.27% ± 3.07%) and N. leptophylla (124.71 ± 3.01, 44.23 ± 5.18 µM TE/g DW and 38.63% ± 1.85%).