Citation: Damodar Kongara, Kim Jin-Kyung, Jun Jong-Gab. Synthesis and pharmacological properties of naturally occurring prenylated and pyranochalcones as potent anti-inflammatory agents[J]. Chinese Chemical Letters, ;2016, 27(5): 698-702. doi: 10.1016/j.cclet.2016.01.043 shu

Synthesis and pharmacological properties of naturally occurring prenylated and pyranochalcones as potent anti-inflammatory agents

a.
Department of Chemistry and Institute of Natural Medicine, Hallym University, Chuncheon 200-702, Republic of Korea
b.
Department of Biomedical Science, College of Natural Science, Catholic University of Daegu, Gyeungsan-Si 700-702, Republic of Korea

Corresponding author: Jun Jong-Gab, jgjun@hallym.ac.kr
Received Date: 4 August 2015
Revised Date: 4 December 2015
Accepted Date: 15 January 2016
Available Online: 1 May 2016

Figures(5)

An efficient approach has been developed for the synthesis of naturally occurring prenylated chalcones viz. kanzonol C (1), stipulin (2), crotaorixin (3), medicagenin (4), licoagrochalcone A (5) and abyssinone D (6) along with the pyranochalcones paratocarpin C (7), anthyllisone (8) and 3-O-methylabyssinone A (9). The key step of the synthesis is a Claisen-Schmidt condensation. Subsequently, their anti-inflammatory effects were investigated in lipopolysaccharides (LPSs)-induced RAW-264.7 macrophages. Of the synthesized chalcones, compounds 5 (IC₅₀=10.41 μmol/L), 6 (IC₅₀=9.65 μmol/L) and 8 (IC₅₀=15.34 μmol/L) show remarkable activity with no cytotoxicity. Compound 9 (IC₅₀=4.5 μmol/L) exhibits maximum (83.6%) nitric oxide (NO) inhibition, but shows slight cytotoxicity. The results reveal that the chalcones bearing the prenyl group at 3- and/or 5-position on ring A (acetophenonemoiety), i.e., 1-4 and 7 show weak, or no inhibition activity, whereas chalcones having the prenyl group only on ring B (aldehyde part), i.e., 5, 6 and 8 show significant activity on the production of inflammatory mediated NO with no cytotoxicity.
- Prenylated chalcone,
- Pyranochalcone,
- Claisen-Schmidt condensation,
- Anti-inflammatory,
- Nitric oxide (NO)
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