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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 and Heilmann, Jörg (2020) Sesquiterpenes from Myrrh and Their ICAM-1 Inhibitory Activity In Vitro. Molecules 26 (1), p. 42.

Date of publication of this fulltext: 26 Feb 2021 17:16
Article
DOI to cite this document: 10.5283/epub.44930


Abstract

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

Item typeArticle
Journal or Publication TitleMolecules
Publisher:MDPI
Open Access Type:Gold (with APC)
Place of Publication:BASEL
Volume:26
Number of Issue or Book Chapter:1
Page Range:p. 42
Date23 December 2020
InstitutionsChemistry and Pharmacy > Institute of Pharmacy > Pharmaceutical Biology (Prof. Heilmann)
Chemistry and Pharmacy > Institute of Pharmacy > Pharmaceutical Biology (Prof. Heilmann)
Identification Number
ValueType
10.3390/molecules26010042DOI
KeywordsULCERATIVE-COLITIS; COFFEE CHARCOAL; LACTONES; COMMIPHORA; COMPONENTS; P65/NF-KAPPA-B; CONSTITUENTS; PATHOGENESIS; INFLAMMATION; EOSINOPHILS; myrrh; Commiphora; ICAM-1; sesquiterpenes; seco-sesquiterpenoides
Dewey Decimal Classification600 Technology > 615 Pharmacy
StatusPublished
RefereedYes, this version has been refereed
Created at the University of RegensburgYes
URN of the UB Regensburgurn:nbn:de:bvb:355-epub-449302
Item ID44930

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