Inhibition of Proinflammatory Cytokine Release by Flavones and Flavanones from the Leaves of Dracaena steudneri Engl

  • Planta Med. 2021 Mar;87(3):209-217. doi: 10.1055/a-1306-1368.
Vaderament-A Nchiozem-Ngnitedem  1  2 ,  Leonidah Kerubo Omosa  1 ,  Kibrom Gebreheiwot Bedane  3 ,  Solomon Derese  1 ,  Michael Spiteller  2
Affiliations
  • 1. Department of Chemistry, University of Nairobi, Nairobi, Kenya.
  • 2. Institute of Environmental Research (INFU), Department of Chemistry and Chemical Biology, Chair of Environmental Chemistry and Analytical Chemistry, TU Dortmund, Dortmund, Germany.
  • 3. Department of Chemistry, Addis Ababa University, Addis Ababa, Ethiopia.
PMID: 33285592 DOI: 10.1055/a-1306-1368
Abstract

The leaves of Dracaena steudneri yielded 6 new flavonoids-3,5,7-trihydroxy-6-methyl-3',4'-methylenedioxyflavone (1: ), 5,7-dihydroxy-3-methoxy-6-methyl-3',4'-methylenedioxyflavone (2: ), 3,5,7-trihydroxy-6-methoxy-3',4'-methylenedioxyflavone (3: ), (2S,3S)-3,7-dihydroxy-6-methoxy-3',4'-methylenedioxyflavanone (4: ), 4',5,7-trihydroxy-3,3',8-trimethoxy-6-methylflavone (5: ), (2R) 7-hydroxy-2',8-dimethoxyflavanone (6: )-together with 13 known congeners. Their structures were established using spectroscopic and spectrometric methods including NMR, CD, and HRMSn measurements. The compounds were evaluated for their anti-inflammatory potential through measurement of the levels of cytokines IL-1β, IL-2, GM-CSF, and TNF-α in the supernatant of human peripheral blood mononuclear cells stimulated by lipopolysaccharide. Flavones derivatives 1: -4: with a C-3'/4' methylenedioxy substituent led to a substantial increase in the production of IL-1β and GM-CSF out of 4 pro-inflammatory cytokines relative to LPS control. Quercetin derivatives 5, 11,: and 13: with a hydroxyl group at C-4' inhibited the production of IL-2, GM-CSF, and TNF-α. The presence of a C-2/C-3 double bond in 14: was pivotal to the significantly stronger (0.4 to 27.5% of LPS control) inhibitory effect compared to its dihydro derivative 8: (36.2 to 262.7% of LPS control) against all tested cytokines. It is important to note that the inhibitory activity of 14: was substantially higher than that of the standard drug used, ibuprofen.

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