Abstract |
Three new macrocyclic jatrophane diterpenes, named euphomelliferine (1) and euphomelliferenes A (2) and B (3), and one new tetracyclic triterpene, 19(10→9)-abeo-8α,9β,10α-tirucalla-5,25-diene-3β,24-diol (6, C-24 epimers), were isolated from the methanolic extract of Euphorbia mellifera. A known ingenane (7) and two jatrophane diterpenes (4 and 5) were also isolated. Their structures were elucidated by extensive spectroscopic methods, including 1D and 2D homo- and heteronuclear NMR experiments. Jatrophane diterpenes 1-3 and 5 were evaluated for their effects on the reversion of multidrug resistance (MDR) mediated by P-glycoprotein, by using the rhodamine-123 exclusion test, on human MDR1 gene-transfected mouse lymphoma cells (L5178Y MDR) and on human colon adenocarcinoma cells (COLO 320). The apoptosis-inducing activity of these compounds was also tested on COLO 320 cells, using the annexin-V/ propidium iodide assay. Diterpenes 1 and 2 displayed significant MDR reversing activity, in a dose-dependent manner, on both cancer cell models. The tested compounds did not induce apoptosis in the COLO 320 cells.
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Authors | Inês Valente, Mariana Reis, Noélia Duarte, Julianna Serly, Joséph Molnár, Maria-José U Ferreira |
Journal | Journal of natural products
(J Nat Prod)
Vol. 75
Issue 11
Pg. 1915-21
(Nov 26 2012)
ISSN: 1520-6025 [Electronic] United States |
PMID | 23098168
(Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
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Chemical References |
- 19(10-9)-abeo-8alpha,9beta,10alpha-tirucalla-5,25-diene-3beta,24-diol
- ATP Binding Cassette Transporter, Subfamily B, Member 1
- Diterpenes
- Triterpenes
- euphomelliferene A
- euphomelliferene B
- euphomelliferine
- ingenane
- jatrophane
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Topics |
- ATP Binding Cassette Transporter, Subfamily B, Member 1
(drug effects, pharmacology)
- Algorithms
- Animals
- Apoptosis
(drug effects)
- Colonic Neoplasms
(drug therapy)
- Diterpenes
(chemistry, isolation & purification, pharmacology)
- Drug Resistance, Multiple
(drug effects)
- Drug Resistance, Neoplasm
(drug effects)
- Euphorbia
(chemistry)
- Humans
- Mice
- Molecular Structure
- Portugal
- Triterpenes
(chemistry, isolation & purification, pharmacology)
- Tumor Cells, Cultured
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