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Ecdysteroids from the underground parts of Rhaponticum acaule (L.) DC


Zughdani, Mhmuod; Yusufoğlu, Hasan Soliman; Ekiz, Güner; Linden, Anthony; Çalış, İhsan (2020). Ecdysteroids from the underground parts of Rhaponticum acaule (L.) DC. Phytochemistry, 180:112530.

Abstract

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: 1H-NMR, 13C-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. Based on all of the evidence, the structures of three undescribed stigmastane-type ecdysteroids were established as 2β,3β,11α,20β,22α,24,28-heptahydroxy-6-oxo-stigmast-7-en-25,29-lactone and the cyclic 22,29-hemiacetals 22R and 22S stigmast-7-en-29-al,2β,3β,11α,20α,22,28-hexahydroxy-6-oxo, and the trivial names acaulesterone and rhapocasterones A and B are suggested, respectively. The structures and absolute configurations of 20-hydroxyecdysone and cyclic-22,29-hemiacetal-22R-stigmast-7-en-29-al,2β,3β,11α,20α,22,28-hexahydroxy-6-oxo were confirmed by X-ray crystal-structure analyses of their acetyl derivatives.

Abstract

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: 1H-NMR, 13C-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. Based on all of the evidence, the structures of three undescribed stigmastane-type ecdysteroids were established as 2β,3β,11α,20β,22α,24,28-heptahydroxy-6-oxo-stigmast-7-en-25,29-lactone and the cyclic 22,29-hemiacetals 22R and 22S stigmast-7-en-29-al,2β,3β,11α,20α,22,28-hexahydroxy-6-oxo, and the trivial names acaulesterone and rhapocasterones A and B are suggested, respectively. The structures and absolute configurations of 20-hydroxyecdysone and cyclic-22,29-hemiacetal-22R-stigmast-7-en-29-al,2β,3β,11α,20α,22,28-hexahydroxy-6-oxo were confirmed by X-ray crystal-structure analyses of their acetyl derivatives.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Uncontrolled Keywords:Plant Science, Biochemistry, Molecular Biology, Horticulture, General Medicine
Language:English
Date:1 December 2020
Deposited On:11 Oct 2020 08:43
Last Modified:11 Oct 2020 08:43
Publisher:Elsevier
ISSN:0031-9422
OA Status:Closed
Publisher DOI:https://doi.org/10.1016/j.phytochem.2020.112530
Project Information:
  • : FunderNear East University Scientific Research Projects
  • : Grant IDSAG-2018-1- 029
  • : Project Title

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