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| Item type: | Article | ||||
|---|---|---|---|---|---|
| Journal or Publication Title: | Bioorganic & medicinal chemistry | ||||
| Publisher: | Elsevier | ||||
| Volume: | 11 | ||||
| Number of Issue or Book Chapter: | 17 | ||||
| Page Range: | pp. 3659-3663 | ||||
| Date: | 2003 | ||||
| Additional Information (public): | CAN 140:125216 11-1 Plant Biochemistry 83869-56-1 (GM-CSF) Role: BSU (Biological study, unclassified), BIOL (Biological study) (cytotoxic vs. anti-inflammatory effects of guaianolide-type sesquiterpene lactones); 648891-46-7; 648891-47-8 Role: NPO (Natural product occurrence), PAC (Pharmacological activity), PRP (Properties), THU (Therapeutic use), BIOL (Biological study), OCCU (Occurrence), USES (Uses) (cytotoxic vs. anti-inflammatory effects of guaianolide-type sesquiterpene lactones); 427893-96-7 (3beta -O-(2-Methylbutyryl)-moroccolide A); 427893-97-8 (Moroccolide A) Role: PAC (Pharmacological activity), THU (Therapeutic use), BIOL (Biological study), USES (Uses) (cytotoxic vs. anti-inflammatory effects of guaianolide-type sesquiterpene lactones) | ||||
| Institutions: | Chemistry and Pharmacy > Institute of Pharmacy > Pharmaceutical Biology (Prof. Heilmann) | ||||
| Identification Number: |
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| Keywords: | Transcription factors Role: BSU (Biological study, unclassified), BIOL (Biological study) (NF-kB (nuclear factor of k light chain gene enhancer in B-cells) cytotoxic vs. anti-inflammatory effects of guaianolide-type sesquiterpene lactones) Anti-inflammatory agents Cytotoxicity Human Inflammation Transcriptional regulation Warionia saharae (cytotoxic vs. anti-inflammatory effects of guaianolide-type sesquiterpene lactones) Interleukin 1beta Interleukin 2 Interleukin 6 Natural products Tumor necrosis factors Role: BSU (Biological study, unclassified), BIOL (Biological study) (cytotoxic vs. anti-inflammatory effects of guaianolide-type sesquiterpene lactones) Sesquiterpenes Role: NPO (Natural product occurrence), PAC (Pharmacological activity), PRP (Properties), THU (Therapeutic use), BIOL (Biological study), OCCU (Occurrence), USES (Uses) (lactones cytotoxic vs. anti-inflammatory effects of guaianolide-type sesquiterpene lactones) Molecular structure (of sesquiterpene lactones) New natural products (sesquiterpene lactones) Warionia sesquiterpene lactone antiinflammatory agent cytotoxicity | ||||
| Dewey Decimal Classification: | 500 Science > 570 Life sciences 500 Science > 540 Chemistry & allied sciences | ||||
| Status: | Published | ||||
| Refereed: | Yes, this version has been refereed | ||||
| Created at the University of Regensburg: | No | ||||
| Item ID: | 17215 |
Abstract
Four guaianolide type sesquiterpene lactones (SL), namely the new 1,2-dihydro-3-oxo-costic acid guaianyl ester 3beta -O-(1,2-didehydro-3-oxo-costoyloxy)-4beta ,10beta -dihydroxy-guaia-1(2)-en-6beta ,12-olide (1) and 3beta -O-(1,2-didehydro-3-oxo-costoyloxy)-4beta ,10beta -dihydroxy-guaia-1(2)-en-6alpha ,12-olide (2), as well as the known moroccolide A [5alpha H-2beta ,4-epoxy-3beta ...
Abstract
Four guaianolide type sesquiterpene lactones (SL), namely the new 1,2-dihydro-3-oxo-costic acid guaianyl ester 3beta -O-(1,2-didehydro-3-oxo-costoyloxy)-4beta ,10beta -dihydroxy-guaia-1(2)-en-6beta ,12-olide (1) and 3beta -O-(1,2-didehydro-3-oxo-costoyloxy)-4beta ,10beta -dihydroxy-guaia-1(2)-en-6alpha ,12-olide (2), as well as the known moroccolide A [5alpha H-2beta ,4-epoxy-3beta -hydroxy-guaia-1(10),11(13)-dien-6beta ,12-olide, 3] and 3beta -O-(2-methylbutyryl)-moroccolide A [5alpha H-2beta ,4-epoxy-3beta -(2-methylbutyryloxy)-guaia-1(10),11(13)-dien-6beta ,12-olide, 4] were examd. for their cytotoxic and anti-inflammatory effects in HeLa, Jurkat T and human peripheral blood mononuclear cells. Compds. 1, 2 and 4 were found to exert a strong cytotoxicity similar in potency in all investigated cell types, whereas 3 was significantly less active. Along with the cytotoxic effect compds. 1 and 4 showed a potent and comparable down-regulation of the mRNAs of the house-keeping genes beta -actin and GAP-DH in PBMCs after 20 h. In contrast, the down-regulation of the PMA-induced mRNA levels of the NF-kB-driven pro-inflammatory genes IL-2, IL-6, GM-CSF, TNF-alpha , and IL-1beta in PBMCs is significantly stronger with compd. 4. Compd. 3 did not significantly modulate cytokine mRNAs levels at biochem. relevant concns. The electromobility shift assay (EMSA), revealed a stronger inhibition of NF-kB for 1 (IC50 2.5 micro M) than for 4 (IC50 5 micro M). Both compds. were also subjected to an IL-6 luciferase reporter gene assay and showed IC50 values of 1.0 (1) and 1.2 micro M (4). Thus, the NF-kB inhibition measured by EMSA, as well as the IL-6 luciferase assay did not reflect the differential modulation of pro-inflammatory genes measured with RT-rt-PCR.
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