Kuck, Katrin and Unterholzner, Anna and Lipowicz, Bartosz and Schwindl, Sebastian and Juergenliemk, Guido and Schmidt, Thomas J. J. and Heilmann, Joerg (2023) Terpenoids from Myrrh and Their Cytotoxic Activity against HeLa Cells. MOLECULES, 28 (4): 1637. ISSN , 1420-3049
Full text not available from this repository. (Request a copy)Abstract
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.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | COMMIPHORA-MYRRHA; ESSENTIAL OIL; NEES ENGL.; SESQUITERPENOID DIMERS; RESINA-COMMIPHORA; CONFIGURATION; BURSERACEAE; TRITERPENES; DERIVATIVES; CHEMISTRY; myrrh; Commiphora; sesquiterpene; disesquiterpenes; triterpenes; HeLa |
| Subjects: | 500 Science > 540 Chemistry & allied sciences 500 Science > 570 Life sciences |
| Divisions: | Chemistry and Pharmacy > Institute of Pharmacy > Pharmaceutical Biology (Prof. Heilmann) |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 14 Mar 2024 11:28 |
| Last Modified: | 14 Mar 2024 11:29 |
| URI: | https://pred.uni-regensburg.de/id/eprint/60087 |
Actions (login required)
 |
View Item |
