Structure and stereochemistry of novel ecdysteroids from the roots of Serratula wolffii

Three new natural ecdysteroids viz. 22‐dehydro‐20‐deoxy‐ajugasterone C (1), 1‐hydroxy‐22‐deoxy‐20,21‐didehydro‐ecdysone (2) and 22‐deoxy‐20,21‐didehydro‐ecdysone (3) were isolated from the methanol extract of the roots of Serratula wolffii. The structures of compounds 1–3 were established by various spectroscopic techniques, including one‐ and two‐dimensional NMR, circular dichroism and mass spectroscopic methods. Copyright © 2010 John Wiley & Sons, Ltd.     

Phytoecdysteroids from Serratula coronata L. for Psoriatic Skincare

Phytoecdysones from Serratula coronata seem to be promising agents for skincare in patients with psoriasis. The aim of the study was to determine the effects of creams containing the extract of S. coronata on psoriatic lesions. Creams with different formulas were prepared: 0-Lekobaza^®, 1-Lekobaza^®, S. coronata, 2-Lekobaza^®, Salicylic acid, 3-Lekobaza^®, S. coronata, Salicylic acid. After examination of skin penetration and biosafety, the designated cream was applied twice daily for 6 weeks on 72 psoriatic plaques located on elbows or knees. The lesions were assessed at baseline and follow-up of 6 weeks. The lesions area was measured, and severity of scaling, erythema, and infiltration was assessed using a 5-point scale (from 0—none to 4—very severe). Skin hydration and structure, pH, transepidermal water loss, erythema, and melanin index were analyzed instrumentally. Creams 1, 2, and 3 significantly reduced the area of psoriatic plaques. Improvement in erythema and infiltration was observed for creams 1 and 3. Creams 1–3 reduced scaling. Our study confirmed a beneficial effect of creams containing S. coronata extract on psoriatic lesions.     

Phytoecdysteroids of plants of the genus Serratula. Ajugasterone C 20,22-monoacetonide from Serratura wolffii

The phytoectysteroids of the epigeal part of the plantSerratula wolffii Andrae have been investigated. The structure of a new ecdysteroid — ajugasterone C 20,22-monoacetonide has been established. Seven known acdysteroids have been isolated and identified.Institute of Biochemistry, Ukrainian Academy of Sciences, Kiev. Institute of Plant Substances, Uzbekistan Republic Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 71–76, January–February, 1992.     

Antioxidant Activity of Ecdysteroids from Serratula strangulata

One new ecdysteroid,(24R)-24-(2-hydroxyethyl)-20-hydrox-yecdysone(3),as well three known ecdysteroids,has been isolated from Chinese herb serratula strangulata and these compoundsd 1-4 showed effective antioxidant activity on AAPH-induced hemolysis of human RBC and Fe^2 cysteine-induced lipid peroxidation of liver microsome.     

Two New Flavone Glucosides from Serratula strangulata

Genus Serratula（Compositae）consists of about 70 species distributed throughout theworld[1]．Serratula species have been used as folk medicine to treat chickenpox,toxicosis,high cholesterol in China[2]. The phytochemical study of plant S．strangulata has not beenreported so far．In the course of our searching for biologically active substances from thisplant,two new flavone glucosides（1,2）were isolated．The present paper covers the isolationand structural elucidation of the two new compounds．     

Sesquiterpenes and Flavonoids from Serratula Strangulata

Phytochemistry investigation of the whole plants of Serratula strangulata has led to the isolation of two sesquiterpenes, six flavonoids, and two isoflavonoids. Among these, a sesquiterpene and two flavonoids are new compounds. The structures of these new compounds were elucidated by spectroscopic methods and 2D NMR techniques.     

Phytoecdysteroids from <Emphasis Type="Italic">Serratula komarovii</Emphasis>

Integristerone A and 2-deoxy-20-hydroxyecdysone were observed for the first time in the aerial and subterrean organs of the eastern Asian plant Serratula komarovii Iljin. -Ecdysone was not found in the plants. The dynamics of phytoecdysteroid content (integristerone A, 20-hydroxyecdysone, and 2-deoxy-20- hydroxyecdysone) in the vegetative and generative organs of this species were investigated.Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 404–406, September–October, 2004.     

Two New Components from Serratula strangulata Iljin

From the alcoholic extract of the whole plants of Serratula strangulata ,two new compounds,named strangusin-A(1) and strangusin-B(2) have been isolated and their structures were established by spectroscopic method.     

Determination of 20-hydroxyecdysone content by thin-layer chromatography and micellar electrokinetic chromatography

Summary Seasonal dependence of 20-hydroxyecdysone content ofSerratula tinctoria andSerratula wolffii (Asteraceae) was investigated by micellar electrokinetic chromatography (MEKC). Samples were collected each month through the vegetation period. The leaves were dried, milled and extracted with methanol. Clean-up of the extracts was by solid-phase extraction using a polyamide micro-column to remove flavonoids and other plant phenolics which can interfere with the analysis. This work deals with the separation of 20-hydroxyecdysone from polypodine B and the seasonal variation of 20-hydroxyecdysone concentration. Determinations have been performed by both thin-layer chromatography and capillary electrophoresis using micellar electrokinetic chromatography. Presented at: Balaton Symposium on High-Performance Separation Methods, Siófok, Hungary, September 3–5, 1997.     

The first two ecdysteroids containing a furan ring from Serratula wolffii

Two new ecdysteroids, named serfurosterone A and serfurosterone B, were isolated from a methanol extract of the roots of Serratula wolffii. Spectroscopic methods revealed that these compounds had previously unknown ecdysteroid structures with acetal functions in the side-chains.     

Phytoecdysteroids of Silene viridiflora

The known ecdysteroids polipodin B, 2-deoxyecdysterone, ecdysterone, 26-hydroxypolipodin B, integristerone A, and sileneosides A and D were observed in the aerial part of Silene viridiflora L. (Caryophyllaceae). 26-Hydroxypolipodin B was observed in this species for the first time.     

矢车菊素结构的2D NMR确定

从菊科药用植物蕴苞麻花头（Serratula stranglata lljin)中分离得到一含氯的愈创木内酯型的倍半萜——矢车菊素（centaurepensin),利用^1H-^1H COSY、HMQC、HMBC及^1H-^1H NOESY等二维波谱技术鉴定了该化合物的结构,并对其^1H和^13C NMR的信号进行了全归属,最终确定了其绝对构型。     

Reversed-phase affinity chromatography of ecdysteroids with boronic acid-containing eluents

Selective effects of boronic acid-containing eluents on the chromatographic behaviour of ecdysteroids are described. The use of such eluents provides a simple, rapid and sensitive means to assess the presence of certain diol groups in ecdysteroids by ordinary RP-HPLC. It is demonstrated that ecdysteroids with different sets of diols in their molecules have individual shapes of chromatographic peaks. A mechanism of the boronic acid effect is discussed.     

Sample preparation for the chromatographic determination of ecdysteroids using solid-phase extraction methods

The ecdysteroids are hormones widely distributed in insects and crustaceans, where they are involved in the regulation of moulting. Methods of sample preparation based on solid-phase extraction of the ecdysteroids from biological samples for subsequent chromatographic analysis are reviewed. Most methods use an initial partition of the sample (or extract) between water or aqueous methanol with a non-polar solvent to remove lipids. The aqueous portion is applied to a cartridge containing C₁₈-bonded silica gel. Removal of polar impurities is then effected, followed by recovery of the ecdysteroids from the cartridge and chromatographic analysis. Results are given for the use of phenylboronic acid (PBA) bonded to silica gel as a means of obtaining a much more specific method of extraction. The PBA phase was shown to have a high affinity for ecdysteroids containing a 20,22-cis-diol but not for compounds possessing only a 2,3-cis-diol.     

Analysis of steroid hormones in effluents of wastewater treatment plants by liquid chromatography-tandem mass spectrometry

This paper presents the development of an analytical procedure for the determination of two sexual steroid hormones: 17beta-estradiol and estrone, and the synthetic contraceptive estrogen, 17alpha-ethynylestradiol in effluents of wastewater treatment plants. Samples are extracted via solid-phase extraction using C18 cartridges. Extracts in ethyl acetate are then purified with a liquid-liquid separation with aqueous sodium chloride, then with a clean-up on a Florisil cartridge. Steroids are analyzed using an LC-MS-MS ion trap system. Internal quantification with the corresponding deuterated steroids leads to limits of quantification at 5 ng/l for estrone and 10 ng/l for estradiol and ethynylestradiol. In mineral spiked water, recoveries are 91% for 17beta-estradiol, 97% for estrone and 87% for 17alpha-ethynylestradiol and RSDs are 15% for 17beta-estradiol, 11% for estrone and 23% for 17alpha-ethynylestradiol.     

Effect of Certain Phytoecdysteroids on Larvae of Colorado Beetle Leptinotarsa decemlineata

The toxicity of phytoecdysteroids 20-hydroxyecdysone (1),-ecdysone (2), polypodin B (3), and poststerone (4) for larvae of colorado beetleLeptinotarsa decemlineataSay. is studied by topical and GI administration.     

Micellar capillary electrophoresis of the ecdysteroids

Summary The technique of micellar capillary electrophoresis has been applied to the separation of ecdysteroids (polyhydroxylated insect hormones) both as pure standards and in the extracts of plants and insect eggs. Succesful separations of a range of closely related ecdysteroids were obtained, however, the quality of the result was found to be critically dependent on the solvent in which the sample was applied and the degree of purity of the extracts. The technique was found to be suitable for the analysis of purified ecdysteroid-rich extracts of plants (Silene nutans, S. otites) and the eggs of the desert locust (Schistocerca gregaria). The elution order of the analytes was similar to that obtained using reversed-phase HPLC.     

Approaches to Total Synthesis of Heterocyclic Steroidal Systems

In heterocyclic steroids the carbon atoms of the steroid skeleton (positions I to 17) are replaced in part by hetero atoms. The term generally denotes compounds containing one or two nitrogen, oxygen, and/or sulfur atoms. The part of the molecule containing the hetero atom is either introduced as a preformed unit or is constructed by stepwise synthesis. The examples given in the present article contain the hetero atoms in ring A, ring B, between rings A and B, and/or between rings C and D.