Unusual derivatives from Hypericum scabrum

Abstract Three new compounds (1–3) with unusual skeletons were isolated from the n-hexane extract of the air-dried aerial parts of Hypericum scabrum. Compound 1 represents the first example of an esterified polycyclic polyprenylated acylphloroglucinol that features a unique tricyclo-[4.3.1.11,4]-und...

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Autores principales: Sara Soroury, Mostafa Alilou, Thomas Gelbrich, Marzieh Tabefam, Ombeline Danton, Samad N. Ebrahimi, Marcel Kaiser, Matthias Hamburger, Hermann Stuppner, Mahdi Moridi Farimani
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Publicado: Nature Portfolio 2021
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Acceso en línea:https://doaj.org/article/5f279ebd0d574f698dce59ad958b4e1e
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spelling oai:doaj.org-article:5f279ebd0d574f698dce59ad958b4e1e2021-12-02T15:23:11ZUnusual derivatives from Hypericum scabrum10.1038/s41598-020-79305-y2045-2322https://doaj.org/article/5f279ebd0d574f698dce59ad958b4e1e2021-01-01T00:00:00Zhttps://doi.org/10.1038/s41598-020-79305-yhttps://doaj.org/toc/2045-2322Abstract Three new compounds (1–3) with unusual skeletons were isolated from the n-hexane extract of the air-dried aerial parts of Hypericum scabrum. Compound 1 represents the first example of an esterified polycyclic polyprenylated acylphloroglucinol that features a unique tricyclo-[4.3.1.11,4]-undecane skeleton. Compound 2 is a fairly simple MPAP, but with an unexpected cycloheptane ring decorated with prenyl substituents, and compound 3 has an unusual 5,5-spiroketal lactone core. Their structures were determined by extensive spectroscopic and spectrometric techniques (1D and 2D NMR, HRESI-TOFMS). Absolute configurations were established by ECD calculations, and the absolute structure of 2 was confirmed by a single crystal determination. Plausible biogenetic pathways of compounds 1–3 were also proposed. The in vitro antiprotozoal activity of the compounds against Trypanosoma brucei rhodesiense and Plasmodium falciparum and cytotoxicity against rat myoblast (L6) cells were determined. Compound 1 showed a moderate activity against T. brucei and P. falciparum, with IC50 values of 3.07 and 2.25 μM, respectively.Sara SorouryMostafa AlilouThomas GelbrichMarzieh TabefamOmbeline DantonSamad N. EbrahimiMarcel KaiserMatthias HamburgerHermann StuppnerMahdi Moridi FarimaniNature PortfolioarticleMedicineRScienceQENScientific Reports, Vol 10, Iss 1, Pp 1-10 (2021)
institution DOAJ
collection DOAJ
language EN
topic Medicine
R
Science
Q
spellingShingle Medicine
R
Science
Q
Sara Soroury
Mostafa Alilou
Thomas Gelbrich
Marzieh Tabefam
Ombeline Danton
Samad N. Ebrahimi
Marcel Kaiser
Matthias Hamburger
Hermann Stuppner
Mahdi Moridi Farimani
Unusual derivatives from Hypericum scabrum
description Abstract Three new compounds (1–3) with unusual skeletons were isolated from the n-hexane extract of the air-dried aerial parts of Hypericum scabrum. Compound 1 represents the first example of an esterified polycyclic polyprenylated acylphloroglucinol that features a unique tricyclo-[4.3.1.11,4]-undecane skeleton. Compound 2 is a fairly simple MPAP, but with an unexpected cycloheptane ring decorated with prenyl substituents, and compound 3 has an unusual 5,5-spiroketal lactone core. Their structures were determined by extensive spectroscopic and spectrometric techniques (1D and 2D NMR, HRESI-TOFMS). Absolute configurations were established by ECD calculations, and the absolute structure of 2 was confirmed by a single crystal determination. Plausible biogenetic pathways of compounds 1–3 were also proposed. The in vitro antiprotozoal activity of the compounds against Trypanosoma brucei rhodesiense and Plasmodium falciparum and cytotoxicity against rat myoblast (L6) cells were determined. Compound 1 showed a moderate activity against T. brucei and P. falciparum, with IC50 values of 3.07 and 2.25 μM, respectively.
format article
author Sara Soroury
Mostafa Alilou
Thomas Gelbrich
Marzieh Tabefam
Ombeline Danton
Samad N. Ebrahimi
Marcel Kaiser
Matthias Hamburger
Hermann Stuppner
Mahdi Moridi Farimani
author_facet Sara Soroury
Mostafa Alilou
Thomas Gelbrich
Marzieh Tabefam
Ombeline Danton
Samad N. Ebrahimi
Marcel Kaiser
Matthias Hamburger
Hermann Stuppner
Mahdi Moridi Farimani
author_sort Sara Soroury
title Unusual derivatives from Hypericum scabrum
title_short Unusual derivatives from Hypericum scabrum
title_full Unusual derivatives from Hypericum scabrum
title_fullStr Unusual derivatives from Hypericum scabrum
title_full_unstemmed Unusual derivatives from Hypericum scabrum
title_sort unusual derivatives from hypericum scabrum
publisher Nature Portfolio
publishDate 2021
url https://doaj.org/article/5f279ebd0d574f698dce59ad958b4e1e
work_keys_str_mv AT sarasoroury unusualderivativesfromhypericumscabrum
AT mostafaalilou unusualderivativesfromhypericumscabrum
AT thomasgelbrich unusualderivativesfromhypericumscabrum
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AT ombelinedanton unusualderivativesfromhypericumscabrum
AT samadnebrahimi unusualderivativesfromhypericumscabrum
AT marcelkaiser unusualderivativesfromhypericumscabrum
AT matthiashamburger unusualderivativesfromhypericumscabrum
AT hermannstuppner unusualderivativesfromhypericumscabrum
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