ABSTRACT
Achyranthes bidentata Blume is widely used as a traditional Chinese medicine with the effects of nourishing the liver and kidneys and strengthening muscles and bones. In this work, a rapid and simple strategy was developed for characterizing phytoecdysteroids by ultra-high-performance liquid chromatography coupled with liner ion trap-Orbitrap mass spectrometry using electrospray ionization in the negative mode. As a result, 47 phytoecdysteroids were unambiguously or tentatively characterized. Among them, seven known compounds were identified according to the reference standards along with molecular formula, retention time and fragmentation patterns, while others were mostly potential new compounds. Through targeted isolation, the structures of three new compounds were determined by NMR spectra, which were consistent with LC-MS characterization. The present study provides an efficient method to deeply characterize phytoecdysteroids.
Subject(s)
Achyranthes/chemistry , Chromatography, High Pressure Liquid/methods , Gas Chromatography-Mass Spectrometry , Mass Spectrometry , Medicine, Chinese Traditional , Spectrometry, Mass, Electrospray Ionization/methodsABSTRACT
The phytoecdysteroids (PEs) comprise a large group of biologically-active plant steroids, which have structures similar to those of insect-molting hormones. PEs are distributed in plants as secondary metabolites that offer protection against phytophagus (plant-eating) insects. When insects consume the plants containing these chemicals, they promptly molt and undergo metabolic destruction; the insects eventually die. Chemically, ecdysteroids are a group of polyhydroxylated ketosteroids that are structurally similar to androgens. The carbon skeleton of ecdysteroids is termed as cyclopentanoperhydro-phenanthrene with a
ABSTRACT
Acetone, methanol and aqueous extracts of the leaves, stem bark and root bark of Vitex schiliebenii belonging to the family Verbenaceae were evaluated for their larvicidal activity against late 3rd/early 4th Anopheles gambiae Giles s.s. larvae (Diptera: Culicidae). The extracts of the acetone leaves and stem bark were active with LC50 values of 14.6 and 17.4 ppm respectively at 24 hrs. These extracts exhibited low toxicity to brine shrimps with LC50 values of 180.9 and 154.4 ppm respectively. The constituents in these extracts were isolated and evaluated and the phytoecdysteroids 20-hydroxyecdysone (1) and stigmasterol (2) were identified as the active principles in the acetone stem bark while γ-sitosterol (3) was the active principle of the acetone leaf extract. The methanol leaf extract, the stem bark aqueous extract and the acetone root bark also showed potency against the mosquito species.
ABSTRACT
Study of secondary plant products is important for understanding their functions and for obtaining biologically active compounds for practical use in different spheres of human activity. Among other plant substances, phytoecdysteroids attract great scientific interest, because of their potential contribution to crop protection strategies and their possible medical uses. Silene repens is widespread in Mongolia. Seed of Silene repens were collected in 2008 from Mongolian and Russian Altai and were cultivated in Siberian Botanical Garden at Tomsk State University, Russia.GoalStudy the dynamics of the 20-hydroxyecdysone in various plant organs of cultivated Silene repens.Material and MethodsThe seasonal dynamics of phytoecdysteroid content (20-hydroxyecdysone) observed in the vegetative and generative organs of cultivated Silene repens was investigated. The quantity of phytoecdysteroids was determined by spectrophotometer UV-1800 (Shimadzu, Japan).ResultsThe content of 20-hydroxyecdysone varied from 0.001 to 1.07 % depending on the organ and growth stage. The maximum content of 20-hydroxyecdysone was observed in actively developing parts of organs: during beginning vegetation in roots (0.3 %); during budding, in the bud (1.00 %); during flowering, in the flowers (1.07 %); during fruiting, in roots (0.31 %). The general trends seen in the distribution of 20-hydroxyecdysone found for cultivated Silene repens from Mongolian and Russian Altai during the plant growth cycle. A high content of 20-hydroxyecdysone during flowering and a low amount during fruiting.ConclusionA high content of 20-hydroxyecdysone during flowering in the flowers and buds (1.07 -1,00 %) and low content of 20-hydroxyecdysone during fruiting in the stem (0.001-0.12 %). The seasonal dynamics of phytoecdysteroids in cultivated Silene repens has been studied for the first time.
ABSTRACT
Silene is a genus of the Caryophyllaceae family, contains more than 700 species, which are widely distributed in Northern Hemisphere, but also in Africa, Asia and South American. Phytochemical investigations of Silene species have revealed that many components from this genus are highly bioactive. More than 400 compounds has been isolated, among them major are phytoecdysteroids. The paper reviews the biological (antitumour, antibacterial and antioxidant) activities and the phytoecdysteroids of genus Silene. We summarized the phytoecdysteroids content referring to 171 species from the genus Silene and list 93 phytoecdysteroids isolated over the past few decades. There are also reports on the mentioned folk and traditional effects of Silene plants.
Silene es un género de la familia Caryophyllaceae, conteniendo más de 70 especies, ampliamente distribuidas no solo en el hemisferio norte, sino que también en Africa, Asia y sud América. Investigaciones fotoquímicas de las especies de Silene han revelado que muchos componentes de este género son altamente bioactivos. Más de 400 compuestos han sido aislados, entre ellos los mayoritarios correspondientes a fitoecdiesteroides. El manuscrito revisa las actividades biológicas (antitumorales, antibacterianas y antioxidantes) y los fitoecdiesteroides del género Silene. Resumimos el contenido de fitoecdiesteroides en 171 especies del género Silene y listamos 93 fitoecdiesteroides aislados desde hace unas pocas décadas. Hay también reportes mencionados acerca de los efectos tradicionales y folclóricos de la plantas del género Silene.
Subject(s)
Anti-Bacterial Agents , Antineoplastic Agents, Phytogenic , Antioxidants , Ecdysteroids , Plants, Medicinal/classification , Silene , Ethnopharmacology , Medicine, Traditional , Species SpecificityABSTRACT
BackgroundPhytoecdysteroids are secondary metabolites produced by many plants. Ecdysteroid containing plants have widely been used in medicine and show pharmacological effects such as: anabolic, adaptogenic, genoprotection, hepatoprotection, antiradiation, anti-inflammatory, antidiabetic and anticancerous.GoalThe aim of this study was to determination, isolation and purification of phytoecdysteroids in the Mongolian flora.Materials and МetodsPlants collected during flowering in western and central regions of Mongolia in 2006-2008 and its flowering stage. Plants speciesclassification was identified by Professor D. Oyunchimeg (Department of botany, Hovd university, Mongolia), Professor A. I Pyak and A. L. Ebeli (Department of botany, Tomsk State University, Russia). The main ecdysteroid components were identified in Silene repens by HPLC using the UV spectrometry. The absorption maximum is due to the presence of a conjugated ketone and occurs near 240-250 nm.Results The ecdysteroid containing plants of Mongolian flora has been studied for the first time. Total 297 species from 171 genera in 50 families for ecdysteroid were screened. Most of them represent a random sampling of plants growing in the selected regions. The highest concentration of ecdysteroids was detected in the family of Caryophyllaceae (genera Silene, Elisanthe, Melandrium), Chenopodiaceae (genera Chenopodium and Axyris) and Asteraceae (genera Rhaponticum and Serratula). Ecdysteroids were investigated in 16 from 297 species of the families Сaryophyllaсеае, Asteraceae and Chenopodiaceae of Mongolian flora, but in 6 of them: Silene ichebogdo, Silene mongolica, Elisanthe aprica, Serratula marginata, Chenopodium frutescens, Axyris prostrate at the first time. Ecdysteroid profile has isolated from aerial parts of Silene repens 5 phytoecdysteroids such as: 2-deoxyecdysone, 2-deoxy-20-hydroxyecdysone, polypodine B, 20-hydroxyecdysone, integristerone A and identified by column chromatography and HPLC methods.ConclusionEcdysteroid profile of 297 plant species was investigated. Five ecdysteroids were isolated, their structure were analyzed by HPLC analysis and UV spectrometry in Silene repens. The basic esdysteroids concentrations in plants of Silene jenissensis, Silene repens, Serratula marginata, Stemmacantha uniflorum and Axyris prostrate L. comprise 2.2%, 1.1%, 1.0%, 1.3% and 0.9% dry weight, respectively. Regarding those three species, there appeared a good source for bioactive substance and a new class of pharmaceutical preparation from its aboveground parts is being developed.
ABSTRACT
In addition to three known phytoecdysteroids, a new phenolic glycoside (named, chenoalbuside) was isolated from the methanol extract of the seeds of Chenopodium album. While the structures of all phytoecdysteroids were elucidated by direct comparison of their spectroscopic data with published data, the structure of chenoalbuside was determined unequivocally by a combination of UV, MS and 1D and 2D NMR spectroscopic analyses. The antioxidant potential of the new compound was assessed by the DPPH assay, and the RC50 value was found to be 1.4 x 10-4 mg/mL.