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Sesquiterpenes from Myrrh and Their ICAM-1 Inhibitory Activity In Vitro
By using various chromatographic steps (silica flash, CPC, preparative HPLC), 16 sesquiterpenes could be isolated from an ethanolic extract of myrrh resin. Their chemical structures were elucidated by 1D and 2D NMR spectroscopy and HRESIMS. Among them, six previously unknown compounds (1–6) and anot...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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MDPI
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7796156/ https://www.ncbi.nlm.nih.gov/pubmed/33374825 http://dx.doi.org/10.3390/molecules26010042 |
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author | Kuck, Katrin Jürgenliemk, Guido Lipowicz, Bartosz Heilmann, Jörg |
author_facet | Kuck, Katrin Jürgenliemk, Guido Lipowicz, Bartosz Heilmann, Jörg |
author_sort | Kuck, Katrin |
collection | PubMed |
description | By using various chromatographic steps (silica flash, CPC, preparative HPLC), 16 sesquiterpenes could be isolated from an ethanolic extract of myrrh resin. Their chemical structures were elucidated by 1D and 2D NMR spectroscopy and HRESIMS. Among them, six previously unknown compounds (1–6) and another four metabolites previously not described for the genus Commiphora (7, 10, 12, 13) could be identified. Sesquiterpenes 1 and 2 are novel 9,10-seco-eudesmanes and exhibited an unprecedented sesquiterpene carbon skeleton, which is described here for the first time. New compound 3 is an 9,10 seco-guaian and the only peroxide isolated from myrrh so far. Compounds 1, 2, 4, 7–9, 11, 13–16 were tested in an ICAM-1 in vitro assay. Compound 7, as well as the reference compound furanoeudesma-1,3-diene, acted as moderate inhibitors of this adhesion molecule ICAM-1 (IC(50): 44.8 and 46.3 μM, respectively). These results give new hints on the activity of sesquiterpenes with regard to ICAM-1 inhibition and possible modes of action of myrrh in anti-inflammatory processes. |
format | Online Article Text |
id | pubmed-7796156 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-77961562021-01-10 Sesquiterpenes from Myrrh and Their ICAM-1 Inhibitory Activity In Vitro Kuck, Katrin Jürgenliemk, Guido Lipowicz, Bartosz Heilmann, Jörg Molecules Article By using various chromatographic steps (silica flash, CPC, preparative HPLC), 16 sesquiterpenes could be isolated from an ethanolic extract of myrrh resin. Their chemical structures were elucidated by 1D and 2D NMR spectroscopy and HRESIMS. Among them, six previously unknown compounds (1–6) and another four metabolites previously not described for the genus Commiphora (7, 10, 12, 13) could be identified. Sesquiterpenes 1 and 2 are novel 9,10-seco-eudesmanes and exhibited an unprecedented sesquiterpene carbon skeleton, which is described here for the first time. New compound 3 is an 9,10 seco-guaian and the only peroxide isolated from myrrh so far. Compounds 1, 2, 4, 7–9, 11, 13–16 were tested in an ICAM-1 in vitro assay. Compound 7, as well as the reference compound furanoeudesma-1,3-diene, acted as moderate inhibitors of this adhesion molecule ICAM-1 (IC(50): 44.8 and 46.3 μM, respectively). These results give new hints on the activity of sesquiterpenes with regard to ICAM-1 inhibition and possible modes of action of myrrh in anti-inflammatory processes. MDPI 2020-12-23 /pmc/articles/PMC7796156/ /pubmed/33374825 http://dx.doi.org/10.3390/molecules26010042 Text en © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Kuck, Katrin Jürgenliemk, Guido Lipowicz, Bartosz Heilmann, Jörg Sesquiterpenes from Myrrh and Their ICAM-1 Inhibitory Activity In Vitro |
title | Sesquiterpenes from Myrrh and Their ICAM-1 Inhibitory Activity In Vitro |
title_full | Sesquiterpenes from Myrrh and Their ICAM-1 Inhibitory Activity In Vitro |
title_fullStr | Sesquiterpenes from Myrrh and Their ICAM-1 Inhibitory Activity In Vitro |
title_full_unstemmed | Sesquiterpenes from Myrrh and Their ICAM-1 Inhibitory Activity In Vitro |
title_short | Sesquiterpenes from Myrrh and Their ICAM-1 Inhibitory Activity In Vitro |
title_sort | sesquiterpenes from myrrh and their icam-1 inhibitory activity in vitro |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7796156/ https://www.ncbi.nlm.nih.gov/pubmed/33374825 http://dx.doi.org/10.3390/molecules26010042 |
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