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Kuck, Katrin ; Jürgenliemk, Guido ; Lipowicz, Bartosz ; Heilmann, Jörg

Sesquiterpenes from Myrrh and Their ICAM-1 Inhibitory Activity In Vitro

Kuck, Katrin, Jürgenliemk, Guido, Lipowicz, Bartosz und Heilmann, Jörg (2020) Sesquiterpenes from Myrrh and Their ICAM-1 Inhibitory Activity In Vitro. Molecules 26 (1), S. 42.

Veröffentlichungsdatum dieses Volltextes: 26 Feb 2021 17:16
Artikel
DOI zum Zitieren dieses Dokuments: 10.5283/epub.44930


Zusammenfassung

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 ...

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 (IC50: 44.8 and 46.3 mu M, 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.



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Details

DokumentenartArtikel
Titel eines Journals oder einer ZeitschriftMolecules
Verlag:MDPI
Ort der Veröffentlichung:BASEL
Band:26
Nummer des Zeitschriftenheftes oder des Kapitels:1
Seitenbereich:S. 42
Datum23 Dezember 2020
InstitutionenChemie und Pharmazie > Institut für Pharmazie > Lehrstuhl Pharmazeutische Biologie (Prof. Heilmann)
Chemie und Pharmazie > Institut für Pharmazie > Lehrstuhl Pharmazeutische Biologie (Prof. Heilmann)
Identifikationsnummer
WertTyp
10.3390/molecules26010042DOI
Stichwörter / KeywordsULCERATIVE-COLITIS; COFFEE CHARCOAL; LACTONES; COMMIPHORA; COMPONENTS; P65/NF-KAPPA-B; CONSTITUENTS; PATHOGENESIS; INFLAMMATION; EOSINOPHILS; myrrh; Commiphora; ICAM-1; sesquiterpenes; seco-sesquiterpenoides
Dewey-Dezimal-Klassifikation600 Technik, Medizin, angewandte Wissenschaften > 615 Pharmazie
StatusVeröffentlicht
BegutachtetJa, diese Version wurde begutachtet
An der Universität Regensburg entstandenJa
URN der UB Regensburgurn:nbn:de:bvb:355-epub-449302
Dokumenten-ID44930

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