Synthesis of Ecdysteroids and Related Compounds

Ковганко, Н. В.; Kashkan, Zh. N.; Chernov, Yu. G.; Ananich, S. K.; Соколов, С. Н.; Survilo, V. L.

doi:10.1023/b:conc.0000011114.96205.98

Cited by 12 publications

(5 citation statements)

References 25 publications

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“…Natural sterols, the precursors in the biosynthesis of ecdysteroids in plants, typically have a 17β-oriented side chain, 21 as do all phytoecdysteroids isolated to date. It must be stressed that the total synthesis of ecdysteroids requires many stereoselective steps and is much less economical than their isolation from plants; 22 therefore, adulteration of the extract with synthetic analogues would be expensive and pointless. It also seems highly improbable that any processing aiming to enrich the 20E content during an extract preparation could result in the 17-epimerization of an ecdysteroid.…”

Section: Results and Discussionmentioning

confidence: 99%

A Commercial Extract of Cyanotis arachnoidea Roots as a Source of Unusual Ecdysteroid Derivatives with Insect Hormone Receptor Binding Activity

Tóth

Herke

Gáti³

et al. 2021

J. Nat. Prod.

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Ecdysteroids act as molting hormones in insects and as nonhormonal anabolic agents and adaptogens in mammals. A wide range of ecdysteroid-containing herbal extracts are available worldwide as food supplements. The aim of this work was to study such an extract as a possible industrial source of new bioactive ecdysteroids. A large-scale chromatographic isolation was performed from an extract of Cyanotis arachnoidea roots. Ten ecdysteroids ( 1 – 10 ) including eight new compounds were isolated and characterized by extensive nuclear magnetic resonance studies. Highly unusual structures were identified, including a H-14β ( 1 , 2 , 4 , and 10 ) moiety, among which a 14β(H)17β(H) phytosteroid ( 1 ) is reported for the first time. Compounds with an intact side chain ( 4 – 10 ) and 11 other natural or semisynthetic ecdysteroids ( 11 – 21 ) were tested for insect ecdysteroid receptor (EcR) binding activity. Two new compounds, i.e., 14-deoxydacryhainansterone ( 5 ) and 22-oxodacryhainansterone ( 6 ), showed strong EcR binding activity (IC 50 = 41.7 and 380 nM, respectively). Six compounds were identified as EcR agonists and another two as antagonists using a transgenic ecdysteroid reporter gene assay. The present results demonstrate that commercial C. arachnoidea extracts are rich in new, unusual bioactive ecdysteroids. Because of the lack of an authentic plant material, the truly biosynthetic or artifactual nature of these compounds cannot be confirmed.

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Section: Results and Discussionmentioning

confidence: 99%

A Commercial Extract of Cyanotis arachnoidea Roots as a Source of Unusual Ecdysteroid Derivatives with Insect Hormone Receptor Binding Activity

Tóth

Herke

Gáti³

et al. 2021

J. Nat. Prod.

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“…However, synthetic ecdysteroid analogues that possess some brassinosteroid-like activity have been prepared [103]. The chemical similarity between the two classes of molecule allows cross-fertilisation in the semi-synthesis of analogues within each class since synthetic strategies and conditions can be similar [104,105].…”

Section: Similarity To Brassinosteroidsmentioning

confidence: 99%

Ecdysteroids

2021

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Ecdysteroid: member of a class of polyhydroxylated steroids found in invertebrate animals (zooecdysteroids; moulting hormones), plants (phytoecdysteroids) and fungi (mycoecdysteroids). Over 500 structural analogues are currently known. Biosynthetically, they derive from C27-, C28- or C29-sterols. The most frequently encountered analogue (in arthropods and plants) is 20-hydroxyecdysone (2β,3β,14α, 20R,22R,25-hexahydroxycholest-7-en-6-one). In arthropods, ecdysteroids occur universally and regulate development by inducing moulting and reproduction, where their action is mediated by high-affinity binding to an intracellular member of the class of nuclear receptor (NR) proteins (ecdysteroid receptor; EcR) dimerised with a second NR (USP/RxR). This receptor complex binds to specific DNA promoter sites and regulates gene expression. In plants, ecdysteroids are a class of secondary compounds, occurring in varying amounts in certain species, but not all in others. Phytoecdysteroids are believed to contribute to the reduction of invertebrate predation by acting as feeding deterrents or endocrine disruptors. Ecdysteroids also possess a wide range of positive pharmacological effects in mammals, where the mode of action involves moderate-affinity binding to plasma-membrane-bound receptors and not interaction with the classical NRs for vertebrate steroid hormones.

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“…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].…”

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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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Synthesis of Ecdysteroids and Related Compounds

Cited by 12 publications

References 25 publications

A Commercial Extract of Cyanotis arachnoidea Roots as a Source of Unusual Ecdysteroid Derivatives with Insect Hormone Receptor Binding Activity

A Commercial Extract of Cyanotis arachnoidea Roots as a Source of Unusual Ecdysteroid Derivatives with Insect Hormone Receptor Binding Activity

Ecdysteroids

Synthesis of New 20-Hydroxyecdysone o-Chlorobenzoyl Derivatives

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