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
Formato:	article
Lenguaje:	EN
Publicado:	Nature Portfolio 2021
Materias:	Medicine R Science Q
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 AT marziehtabefam unusualderivativesfromhypericumscabrum AT ombelinedanton unusualderivativesfromhypericumscabrum AT samadnebrahimi unusualderivativesfromhypericumscabrum AT marcelkaiser unusualderivativesfromhypericumscabrum AT matthiashamburger unusualderivativesfromhypericumscabrum AT hermannstuppner unusualderivativesfromhypericumscabrum AT mahdimoridifarimani unusualderivativesfromhypericumscabrum
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Unusual derivatives from Hypericum scabrum

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