Antimicrobial activity of natural ecdysteroids from Serratula coronata L. and their acyl derivatives

Ширшова, Т. И.; Politova, N. K.; Burtseva, S. A.; Beshlei, I. V.; Володин, В. В.

doi:10.1007/s11094-006-0106-7

Cited by 13 publications

(13 citation statements)

References 7 publications

(6 reference statements)

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“…From a microbiological point of view, the chloroform extract seems the most interesting because of the presence of phytoecdysteroids (Mamadalieva et al, 2008). The literature data indicate the antimicrobial activity of slightly polar acylated ecdysteroids, such as simple acetyl derivatives (Shirshova et al, 2006;Mamadalieva, 2012). The following pharmacological effects are attributed to Leuzea carthamoides, a plant containing high levels of ecdysteroids (especially 20-hydroxyecdysone, also identified in the Ragged Robin): roborant, adaptogenic and antidepressive (Slama and Lafont, 1995).…”

Section: Pharmacological Profilementioning

confidence: 99%

Ragged Robin (Lychnis flos-cuculi) - a plant with potential medicinal value

Maliński

Michalska

Tomczykowa

et al. 2014

Revista Brasileira de Farmacognosia

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Taxonomy Secondary metabolites Biological activity In vitro cultures Micropropagation A B S T R A C T Lychnis flos-cuculi L., Caryophyllaceae, contains a number of active compounds belonging to several chemical groups. Previous studies have led to the identification of phytoecdysteroids, triterpenoids saponins, volatile compounds, fatty acid derivatives, phenolic acids and flavonoids. Research on pharmacological activity showed that plant extracts inhibited the growth of bacteria and fungi. The antimitotic properties of preparations from the herb L. flos-cuculi were also reported. The phytochemical analyses demonstrated that this taxon contains pharmaceutically promising compounds, but more phytochemical and pharmacological studies of L. flos-cuculi are needed for further information regarding this plant. This review summarizes reports regarding chemical composition and biological activity of L. flos-cuculi as well as several cognate species, which pose opportunities related to in vitro propagation and cell and tissue cultures. In vitro-regenerated plantlets could be a good source of genetically uniform plant material for future research.

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Section: Pharmacological Profilementioning

confidence: 99%

Ragged Robin (Lychnis flos-cuculi) - a plant with potential medicinal value

Maliński

Michalska

Tomczykowa

et al. 2014

Revista Brasileira de Farmacognosia

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“…Proved manifestation phytoecdysteroids adaptogenic, anabolic, radioprotective, anti-ischemic, and tonic action were set efficiency of their use in blocking the inflammatory and immunological processes in the healing of wounds and burns [1][2][3][4][5].…”

Section: Introductionmentioning

confidence: 99%

Preparation and Analysis of the NMR Spectra of the Pharmaceutical Substance«oose-11,12,13»

Berkenov¹,

Um²

2017

Asian J Pharm Clin Res

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Objective: The main issue of this work is obtained, to researching of supramolecular complexes of 20-hydroxyecdysone (20 E) with α-, β-, and γ-cyclodextrins (CD). Methods:The foundation of substance phytoecdysteroid 20 E was isolated from an ethanol extract plant Otites orae-syvaschicae Klok (OOSE). A method of the development of pharmaceutical substances was used during complexed organic relationship in the way of intense mechanical mixing 20 E with α-, β-or γ-СD. The complexation of 20 E with α-, β-, and γ-СD was studied by nuclear magnetic resonance (NMR) method of spectroscopy. Results:In the study of the integrated intensities molecules signals steroid guest and host CD complex stoichiometric ratio 1:1 was proved. The formation of clathrates was established after A and B nuclei ecdysterone had been arranged in the internal cavity of CD.Сonclusion: Supramolecular complexes of 20 E with α-, β-, and γ-СD were received during made works. The objects of research were analyzed and described with the help of NMR spectroscopy. The developed technology will be the main device for operating and identification of pharmaceutical substance

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“…Three secondary ones on C 2 , C 22 , and C 3 are more reactive; on C 25 , C 20 , and C 14 , less reactive [3,4]. A study of the chemical modifications of 20-hydroxyecdysone defined the reactivities of the hydroxyls toward conjugation and placed them in the following order of decreasing reactivity: C 2 > C 22 > C 3 > C 25 > C 20 >> C 14 [5].We synthesized o-chlorobenzoyl derivatives of 20-hydroxyecdysone. Acylation of 20-hydroxyecdysone used o-chlorobenzoylchloride in Py at 45-50°C for 2 h [6].…”

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Synthesis of New 20-Hydroxyecdysone o-Chlorobenzoyl Derivatives

et al. 2015

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Acylation by o-chlorobenzoylchloride produced new 20-hydroxyecdysone (1) derivatives with o-chlorobenzoyl fragments (2)(3)(4)(5) in the 20-hydroxyecdysone.Phytoecdysteroids are widely distributed in hundreds of plant species belonging to dozens of families and genera. A total of >400 ecdysteroids including >300 of plant origin have been identified. Recent research found that practically all terrestrial and aquatic plants have genes for synthesizing ecdysteroids [1].Chemical modifications of 20-hydroxyecdysone derivatives are currently of great interest. 20-Hydroxyecdysone is the most common phytoecdysteroid and offers a convenient synthon for preparing new biologically active compounds for medical and household needs [2]. 20-Hydroxyecdysone is polyhydroxylated with six hydroxyls. Three secondary ones on C 2 , C 22 , and C 3 are more reactive; on C 25 , C 20 , and C 14 , less reactive [3,4]. A study of the chemical modifications of 20-hydroxyecdysone defined the reactivities of the hydroxyls toward conjugation and placed them in the following order of decreasing reactivity: C 2 > C 22 > C 3 > C 25 > C 20 >> C 14 [5].We synthesized o-chlorobenzoyl derivatives of 20-hydroxyecdysone. Acylation of 20-hydroxyecdysone used o-chlorobenzoylchloride in Py at 45-50°C for 2 h [6]. Therefore, a mixture of 20-hydroxyecdysone mono-, di-, tri-, and tetraesters was rather readily obtained by direct esterification with a large excess of the acid chloride.Column chromatography of the mixture separated pure components such as the novel 2-O-(o-chlorobenzoyl)-20-hydroxyecdysone (2), 2,3-di-O-(o-chlorobenzoyl)-20-hydroxyecdysone (3), 2,3,22-tri-O-(o-chlorobenzoyl)-20-hydroxyecdysone (4), and 2,3,22,25-tetra-O-(o-chlorobenzoyl)-20-hydroxyecdysone (5). Their structures were elucidated using PMR and 13 C NMR spectra and 2D experiments. It is of utmost importance to note that the labile 14D-hydroxy and ' 7 -6-ketone groups characteristic of starting 20-hydroxyecdysone (1) were retained in all acylation products. The number of o-chlorobenzoyl groups attached to 20-hydroxyecdysone could be determined rather simply from the PMR spectral data of the acylation products.

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Antimicrobial activity of natural ecdysteroids from Serratula coronata L. and their acyl derivatives

Cited by 13 publications

References 7 publications

Ragged Robin (Lychnis flos-cuculi) - a plant with potential medicinal value

Ragged Robin (Lychnis flos-cuculi) - a plant with potential medicinal value

Preparation and Analysis of the NMR Spectra of the Pharmaceutical Substance«oose-11,12,13»

Synthesis of New 20-Hydroxyecdysone o-Chlorobenzoyl Derivatives

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