Anti-inflammatory steroidal sapogenins and a conjugated chalcone-stilbene from Dracaena usambarensis Engl.

Autor: Nchiozem-Ngnitedem VA; Department of Chemistry, University of Nairobi, P. O. Box 30197-00100, Nairobi, Kenya; Institute of Environmental Research (INFU), Department of Chemistry and Chemical Biology, Environmental Chemistry and Analytical Chemistry, TU Dortmund, Otto-Hahn-Straße 6, 44221 Dortmund, Germany., Omosa LK; Department of Chemistry, University of Nairobi, P. O. Box 30197-00100, Nairobi, Kenya. Electronic address: lkerubo@uonbi.ac.ke., Bedane KG; Department of Chemistry, Addis Ababa University, P.O. Box 33658, Addis Ababa, Ethiopia., Derese S; Department of Chemistry, University of Nairobi, P. O. Box 30197-00100, Nairobi, Kenya., Brieger L; Inorganic Chemistry, Department of Chemistry and Chemical Biology, TU Dortmund, Otto-Hahn-Straße 6, 44227 Dortmund, Germany., Strohmann C; Inorganic Chemistry, Department of Chemistry and Chemical Biology, TU Dortmund, Otto-Hahn-Straße 6, 44227 Dortmund, Germany., Spiteller M; Institute of Environmental Research (INFU), Department of Chemistry and Chemical Biology, Environmental Chemistry and Analytical Chemistry, TU Dortmund, Otto-Hahn-Straße 6, 44221 Dortmund, Germany.
Jazyk: angličtina
Zdroj: Fitoterapia [Fitoterapia] 2020 Oct; Vol. 146, pp. 104717. Date of Electronic Publication: 2020 Aug 31.
DOI: 10.1016/j.fitote.2020.104717
Abstrakt: Four new steroidal sapogenins, dracaenogenins CF (1-4), a new conjugated chalcone-stilbene, 3''-methoxycochinchinenene H (5) together with eight known compounds namely, (25S)-spirosta-1,4-dien-3-one (6), trans-resveratrol (7), 4,4'-dihydroxy-3'-methoxychalcone (8), N-trans-coumaroyltyramine (9), N-trans-p-coumaroyloctopamine (10), N-trans-feruloyloctopamine (11), 7-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-N 2 ,N 3 -bis(4-hydroxyphenethyl)-6-methoxy-1,2-dihydronaphthalene-2,3-dicarboxamide (12) and grossamide (13) were isolated from the stems of Dracaena usambarensis Engl. from Kenya. It is important to note that compounds 12 and 13 are being reported from this genus for the first time. Structural elucidation of the isolated compounds was done using spectroscopic (NMR, UV, IR, optical rotation) and spectrometric (HRESIMS) techniques. The absolute and relative configurations of the isolated compounds were determined by employing single crystal X-ray crystallography analysis, NOESY correlations and coupling constants. The anti-inflammatory potencies of the isolated compounds were evaluated by measuring the levels of four cytokines (IL-1β, IL-2, GM-CSF and TNF-α) in the supernatant media of human peripheral blood mononuclear cells (PBMCs) stimulated by lipopolysaccharide (LPS). At the tested concentration of 100 μM, the new conjugated chalcone-stilbene 5, the dihydrochalcone, 8 and the lignanamide, 13 were substantially more potent than the standard drug, ibuprofen, inhibiting the release of all the cytokines, IL-1β, IL-2, GM-CSF and TNF-α from 0.06-58.04% compared to LPS control. These compounds should therefore be considered for development into anti-inflammatory drug candidates. Compound 7 significantly decreased the release of GM-CSF (6.11% of LPS control) and TNF-α (18.35% of LPS control). The cytokine TNF-α was sensitive to all the tested compounds 1-13.
(Copyright © 2020 Elsevier B.V. All rights reserved.)
Databáze: MEDLINE
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