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...
Guardado en:
Autores principales: | , , , , , , , , , |
---|---|
Formato: | article |
Lenguaje: | EN |
Publicado: |
Nature Portfolio
2021
|
Materias: | |
Acceso en línea: | https://doaj.org/article/5f279ebd0d574f698dce59ad958b4e1e |
Etiquetas: |
Agregar Etiqueta
Sin Etiquetas, Sea el primero en etiquetar este registro!
|
id |
oai:doaj.org-article:5f279ebd0d574f698dce59ad958b4e1e |
---|---|
record_format |
dspace |
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 |
_version_ |
1718387267014230016 |