Journal
MOLECULES
Volume 19, Issue 10, Pages 16058-16081Publisher
MDPI AG
DOI: 10.3390/molecules191016058
Keywords
anti-inflammatory; diarylpentanoid; RAW 264.7; curcumin; SAR; pharmacophore
Funding
- Ministry of Education (MOE) of Malaysia [ERGS/1/11/STG/UPM/01/24]
- Universiti Putra Malaysia [ERGS/1/11/STG/UPM/01/24]
- Scientific Chair Unit, Taibah University
- Malaysian Ministry of Science, Technology and Innovation (MOSTI) under the National Science Foundation (NSF)
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A series of ninety-seven diarylpentanoid derivatives were synthesized and evaluated for their anti-inflammatory activity through NO suppression assay using interferone gamma (IFN-gamma)/lipopolysaccharide (LPS)-stimulated RAW264.7 macrophages. Twelve compounds (9, 25, 28, 43, 63, 64, 81, 83, 84, 86, 88 and 97) exhibited greater or similar NO inhibitory activity in comparison with curcumin (14.7 +/- 0.2 mu M), notably compounds 88 and 97, which demonstrated the most significant NO suppression activity with IC50 values of 4.9 +/- 0.3 mu M and 9.6 +/- 0.5 mu M, respectively. A structure-activity relationship (SAR) study revealed that the presence of a hydroxyl group in both aromatic rings is critical for bioactivity of these molecules. With the exception of the polyphenolic derivatives, low electron density in ring-A and high electron density in ring-B are important for enhancing NO inhibition. Meanwhile, pharmacophore mapping showed that hydroxyl substituents at both meta-and para-positions of ring-B could be the marker for highly active diarylpentanoid derivatives.
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