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

Abstract

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.

Highly Oxidized Ecdysteroids from a Commercial Cyanotis arachnoidea Root Extract as Potent Blood–Brain Barrier Protective Agents

“…The structure of the isolated compounds was elucidated based on their molecular formulas, which were obtained by high-resolution mass spectrometry (HRMS) and on detailed nuclear magnetic resonance (NMR) studies. A preliminary assessment of the NMR spectra revealed that the currently isolated compounds 2 – 4 shared structural similarities with 14β,15-dihydrocalonysterone ( 1 , C 27 H 42 O 7 ) that was recently reported by our group; 10 therefore, the structure elucidation is described in relation to this compound.…”

“…Furthermore, while the cytoprotective effect of 20E in mammals has been relatively well described, little is known about the pharmacology of minor ecdysteroids. Therefore, as a follow-up to our recent report, in this current study it was the aim to further evaluate the chemical value of the commercially available Cyanotis extract and the pharmacological value of the isolated ecdysteroids with regard to their potential cytoprotective effects on the BBB.…”

“…In our previous work, it was demonstrated that commercial extracts of this herbal drug contain rare minor ecdysteroids and that such compounds have the potential for the development of new compounds for biological pest management. 10 Damage to the blood−brain barrier (BBB) is a key mechanism in the pathogenesis of many acute (e.g., stroke, traumatic brain injury) and chronic central nervous system (CNS) pathologies (e.g., Alzheimer's, Parkinson's, and Huntington's disease). 11−13 Thus far, the possible BBBprotective activity of ecdysteroids has not been studied.…”

“…These food supplements typically originate from the roots of Cyanotis arachnoidea C. B. Clarke (Commeliniaceae). In our previous work, it was demonstrated that commercial extracts of this herbal drug contain rare minor ecdysteroids and that such compounds have the potential for the development of new compounds for biological pest management …”

“…In our previous work, it was demonstrated that commercial extracts of this herbal drug contain rare minor ecdysteroids and that such compounds have the potential for the development of new compounds for biological pest management. 10 …”