Turkesterone

Two undescribed alkaloids, 15-carboxydihydroerysotrine ( 1 ) and (14  R )-4-methoxy-13,14-dihydrooxypalmatine ( 2 ), along with six known compounds, 1,6-didehydro-3,15,16-trimethoxy-9-methylerythrinanium ( 3 ), 8-oxytetrahydropalmatine ( 4 ), 20-hydroxyecdysone ( 5 ), makisterone A ( 6 ) turkesterone ( 7 ) and magnoflorine ( 8 ) were isolated from the root part of Cocculus hirsutus (L.) W. Theob. Their structures were established based on detailed analysis of NMR, UV-Vis, HRESIMS, and single-crystal XRD spectroscopic experiments...

RATIONALE: Recently, there has been a report suggesting that ecdysteroids can enhance sports performance, making them relevant substances in doping control. Hence, it is imperative to examine the analytical characteristics of ecdysteroids in biological samples to identify their misuse in competitive sports. METHODS: To assess the doping of ecdysteroids such as ecdysone, ecdysterone, ponasterone A, turkesterone, and ajugasterone C, a fast and sensitive extraction and detection method was developed, optimized, and validated using equine urine and plasma...

Besides their common use as an adaptogen, Rhaponticum carthamoides (Willd.) Iljin. rhizome and its root extract (RCE) are also reported to beneficially affect lipid metabolism. The main characteristic secondary metabolites of RCE are phytoecdysteroids. In order to determine an RCE's phytoecdysteroid profile, a novel, sensitive, and robust high-performance thin-layer chromatography (HPTLC) method was developed and validated. Moreover, a comparative analysis was conducted to investigate the effects of RCE and its secondary metabolites on adipogenesis and adipolysis...

The genus Ajuga (Lamiaceae) is rich in medicinally important species with biological activities ranging from anti-inflammatory, antitumor, neuroprotective, and antidiabetic to antibacterial, antiviral, cytotoxic, and insecticidal effects. Every species contains a unique and complex mixture of bioactive metabolites-phytoecdysteroids (PEs), iridoid glycosides, withanolides, neo-clerodane terpenoids, flavonoids, phenolics, and other chemicals with high therapeutic potential. Phytoecdysteroids, the main compounds of interest, are natural anabolic and adaptogenic agents that are widely used as components of dietary supplements...

Natural-derived steroids and their analogues are present in various plants and insects. To minimize the chance of missing a positive doping test and avoiding potentially serious health problems, adequate screening methods are necessary for the detection of a wide range of natural-derived steroids and their analogues in dietary supplements. In this study, an accurate and simple liquid-chromatography-tandem mass spectrometry (LC-MS/MS) method was developed and validated to determine and quantify the natural-derived steroids and their analogues according to the International Conference on Harmonization of technical Requirements for Registration of Pharmaceuticals for Human Use guidelines...

Vitex doniana Sweet is an African medicinal species that is prescribed as an aqueous bark extract to be applied topically or orally to achieve anti-infective outcomes. In select regions it is also taken orally as an antimalarial agent. The aim of the current study was to explore the biological properties of V. doniana and isolated compounds in the context of pathogenic bacteria and the protozoan parasite Plasmodium falciparum . Three compounds were isolated and assigned by nuclear magnetic resonance spectroscopy as ecdysteroids: (1) 20-hydroxyecdysone, (2) turkesterone, and (3) ajugasterone C...

Ecdysteroids (ECs) are steroid hormones originally found in the animal kingdom where they function as insect molting hormones. Interestingly, a relatively high number of these substances can also be formed in plant cells. Moreover, ECs have certain regulatory effects on plant physiology, but their role in plants still requires further study. One of the main aims of the present study was to verify a hypothesis that fenarimol, an inhibitor of the biosynthesis of ECs in the animal kingdom, also affects the content of endogenous ECs in plants using winter wheat Triticum aestivum L...

In addition to two known ecdysteroids, 20-hydroxyecdysone and turkesterone, three previously undescribed stigmastane-type ecdysteroids were isolated from the underground parts of Rhaponticum acaule (L.) DC. by chromatographic techniques (CC, VLC, MPLC). The structures of the compounds were established by chemical (acetylation) and spectroscopic methods including UV, IR, HRMS, 1D-NMR: 1 H-NMR, 13 C-NMR, DEPT-135. and 2D-NMR: COSY, NOESY, HSQC, HMBC. Two compounds were isolated as an isomeric mixture and each of them was purified and converted to the corresponding acetylated derivative...

INTRODUCTION: Ajuga turkestanica is a plant used in traditional medicine for its high ecdysteroid content, including the presence of the particularly active turkesterone, which possess efficient anabolic activity. OBJECTIVES: To isolate and identify minor ecdysteroids present in a semi-purified plant fraction containing ca. 70% turkesterone. MATERIAL AND METHODS: Multi-step preparative HPLC (combining RP- and NP-HPLC systems) was used to purify the different components present in the turkesterone fraction...

Introduction of phytoecdysteroids (ecdysterone, turkesterone and ñyasterone) to rats subjected to prolonged immobilization stress significantly decreased involution of the thymus and spleen, contributed to normalization of increased mass of adrenal glands, and restored their content of ascorbic acid and cholesterol. In the liver of stressed animals, phytoecdysteroids prevented sharp decrease in the glycogen concentration, showed a clear trend toward normalization of the ratio of lactic and pyruvic acids, maintained homeostasis of macroergic phosphorus compounds, and increased the activity of antioxidant enzymes that inhibit lipid peroxidation...

A novel phytoecdysteroid, vitexirone, has been isolated from a MeOH extract of the root bark of the East African medicinal plantVitex fisherii by recycling high-performance liquid chromatography on a semipreparative scale. In addition, three known phytoecdysteroids, 20-hydroxyecdysone, ajugasterone C, and turkesterone, also were isolated. The structure of vitexirone has been established spectroscopically. The position and stereochemistry of the 11-α-hydroxy group of ajugasterone C and vitexirone were confirmed by the(1)H-(1)H homonuclear COSY NMR data...

A series of phytoecodysteroids, including alpha-ecdysone, 2-deoxy-alpha-ecdysone, and 2-deoxyecdysterone isolated from Silene praemixta, integristerone A and ecdysterone isolated from Rhaponticum carthamoides and 22-acetylcyasterone and turkesterone isolated from Ajuga turkestanica, exhibit a pronounced hypoglycemic effect in experiments on intact male rats. The most active compounds--ecdysteron and turkesterone--also produce an expressed hypoglycemic effect in animals with model hyperglycemia induced by the administration of glucose, adrenalin and alloxan...

Influence of phytoecdysteroids (isolated from Ajuga turkestanica) and bemithyl on the duration of swimming of laboratory animals (mice, rats) under various experimental conditions was studied. Turkesteron and cyasteron increased duration of dynamic work carried out by animals, decreased fatigue, and accelerated recovery processes to a greater extent that did bemithyl. The positive influence of phytoecdysteroids on the working capacity is based on the activation of metabolic processes in skeletal muscles, directed to support the homeostasis of energy production...

Seventeen additional minor ecdysteroid compounds were isolated and identified from the roots of Leuzea carthamoides (Wild.) DC. Eight of them are new phytoecdysteroids: carthamoleusterone (13) is a new side-chain cyclo-ether with five-membered ring; 14-epi-ponasterone A 22-glucoside (12) is a rare and unusual natural 14 beta-OH epimer; 15-hydroxyponasterone A (11) is also new and rare with its C-15 substituted position, as well as 22-deoxy-28-hydroxymakisterone C (18) possessing secondary hydroxyl in position C-28 and 26-hydroxymakisterone C (20) with hydroxy groups in positions 25 and 26...

Turkesterone is a phytoecdysteroid possessing an 11alpha-hydroxyl group. It is an analogue of the insect steroid hormone 20-hydroxyecdysone. Previous ecdysteroid QSAR and molecular modelling studies predicted that the cavity of the ligand binding domain of the ecdysteroid receptor would possess space in the vicinity of C-11/C-12 of the ecdysteroid. We report the regioselective synthesis of a series of turkesterone 11alpha-acyl derivatives in order to explore this possibility. The structures of the analogues have been unambiguously determined by spectroscopic means (NMR and low-resolution mass spectrometry)...

Three ecdysteroid 7,9(11)-dien-7-ones (dacryhainansterone, 25-hydroxydacryhainansterone and kaladasterone) were prepared by dehydration of the corresponding 11a-hydroxy ecdysteroids (ajugasterone C, turkesterone and muristerone A, respectively). The biological activities of the dienones in the Drosophila melanogaster B(II) cell bioassay, which reflect the affinity for the ecdysteroid receptor complex, showed that the dienones retain high biological activity. Irradiation at 350 nm of the ecdysteroid dienones (100 nM) with bacterially-expressed dipteran and lepidopteran ecdysteroid receptor proteins (DmEcR/DmUSP or CfEcR/CfUSP), followed by loading with [(3)H]ponasterone A revealed that irradiation of dacryhainansterone or kaladasterone resulted in blocking of >70% of the specific binding sites...

Two new ecdysteroids, 24-epi-pinnatasterone (1) and scabrasterone (2), together with 11 known ecdysteroids, calonysterone, pterosterone, 24-epi-makisterone A, 20-hydroxyecdysone (3), polypodine B, ajugasterone C, pinnatasterone (4), 11alpha-hydroxyecdysone, 24-epi-abutasterone, 20,26-dihydroxyecdysone, and turkesterone (5), were isolated from the stem bark of Vitex scabra. This plant species contained a very high concentration (1.8%) of 3 and thus provided a good source of this parent ecdysteroid and related rare ecdysteroids...

Phytoecdysteroids ecdysteron and turkesteron isolated from Ajuga turkestanica (Rgl.) Brig. decrease the manifestations of uremic intoxication in rats with experimental renal pathology induced by a nephrotoxic mixture (containing uranyl acetate and glycerol). Injected in a dose of 5 mg/kg, the drugs restore glomerular filtration level, favor the disappearance of the albuminuria and normalize urinary sediments. The nephroprotector effect of the phytoecdysteroids studied resembles the action of a steroidal anabolic drug nerobol...

A new ecdysteroid, 26-hydroxypinnatasterone (1), together with 20-hydroxyecdysone, was isolated from the stem barks of Vitex cymosa. 20-Hydroxyecdysone, ajugasterone C, ajugasterone C monoacetonide and turkesterone were isolated from the branches of V. polygama. The structure of 1 was determined by spectroscopic methods.

Disorders of lung local defensive mechanisms were noted in rats with alloxane-induced diabetes mellitus, which showed itself as neutrophilic infiltration and decrease of macrophagal bactericidal action in the lungs. All this contributed to the development and chronization of bronchopulmonary inflammatory diseases. Use of maninil caused further inhibition of cellular and humoral lung immunity indices. Addition of 11,20-dihydroxyecdysone (turkesterone) to the therapy resulted in positive changes in the lung defense mechanisms...