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Kuck, Katrin ; Unterholzner, Anna ; Lipowicz, Bartosz ; Schwindl, Sebastian ; Jürgenliemk, Guido ; Schmidt, Thomas J. ; Heilmann, Jörg

Terpenoids from Myrrh and Their Cytotoxic Activity against HeLa Cells

Kuck, Katrin, Unterholzner, Anna, Lipowicz, Bartosz, Schwindl, Sebastian, Jürgenliemk, Guido, Schmidt, Thomas J. und Heilmann, Jörg (2023) Terpenoids from Myrrh and Their Cytotoxic Activity against HeLa Cells. Molecules 28 (4), S. 1637.

Veröffentlichungsdatum dieses Volltextes: 06 Mrz 2023 15:12
Artikel
DOI zum Zitieren dieses Dokuments: 10.5283/epub.53896


Zusammenfassung

The oleo-gum resin of Commiphora myrrha (Nees) Engl. has a long history of medicinal use, although many of its constituents are still unknown. In the present investigation, 34 secondary metabolites were isolated from myrrh resin using different chromatographic techniques (silica flash chromatography, CPC, and preparative HPLC) and their structures were elucidated with NMR spectroscopy, HRESIMS, ...

The oleo-gum resin of Commiphora myrrha (Nees) Engl. has a long history of medicinal use, although many of its constituents are still unknown. In the present investigation, 34 secondary metabolites were isolated from myrrh resin using different chromatographic techniques (silica flash chromatography, CPC, and preparative HPLC) and their structures were elucidated with NMR spectroscopy, HRESIMS, CD spectroscopy, and ECD calculations. Among the isolated substances are seven sesquiterpenes (1-7), one disesquiterpene (8), and two triterpenes (23, 24), which were hitherto unknown, and numerous substances are described here for the first time for C. myrrha or the genus Commiphora. Furthermore, the effects of selected terpenes on cervix cancer cells (HeLa) were studied in an MTT-based in vitro assay. Three triterpenes were observed to be the most toxic with moderate IC50 values of 60.3 (29), 74.5 (33), and 78.9 mu M (26). Due to the different activity of the structurally similar triterpenoids, the impact of different structural elements on the cytotoxic effect could be discussed and linked to the presence of a 1,2,3-trihydroxy substructure in the A ring. The influence on TNF-alpha dependent expression of the intercellular adhesion molecule 1 (ICAM-1) in human microvascular endothelial cells (HMEC-1) was also tested for 4-6, 9-11, 17, 18, 20, and 27 in vitro, but revealed less than 20% ICAM-1 reduction and, therefore, no significant anti-inflammatory activity.



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Details

DokumentenartArtikel
Titel eines Journals oder einer ZeitschriftMolecules
Verlag:MDPI
Ort der Veröffentlichung:BASEL
Band:28
Nummer des Zeitschriftenheftes oder des Kapitels:4
Seitenbereich:S. 1637
Datum8 Februar 2023
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/molecules28041637DOI
Stichwörter / KeywordsCOMMIPHORA-MYRRHA; ESSENTIAL OIL; NEES ENGL.; SESQUITERPENOID DIMERS; RESINA-COMMIPHORA; CONFIGURATION; BURSERACEAE; TRITERPENES; DERIVATIVES; CHEMISTRY; myrrh; Commiphora; sesquiterpene; disesquiterpenes; triterpenes; HeLa
Dewey-Dezimal-Klassifikation500 Naturwissenschaften und Mathematik > 540 Chemie
500 Naturwissenschaften und Mathematik > 570 Biowissenschaften, Biologie
StatusVeröffentlicht
BegutachtetJa, diese Version wurde begutachtet
An der Universität Regensburg entstandenJa
URN der UB Regensburgurn:nbn:de:bvb:355-epub-538964
Dokumenten-ID53896

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