Syntheses and Anti-inflammatory Activity of Natural 1,3-Diarylpropenes

First syntheses of five natural 1,3-diarylpropenes (cinnamylphenols) 2–4, 7, and 8 along with synthesis of two other natural 1,3-diarylpropenes 1 and 5 and E-isomer of mucronulastyrene (6) were achieved by Friedel–Crafts alkylation as a key step. Subsequently, their anti-inflammatory effects were al...

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Veröffentlicht in:Chemical & pharmaceutical bulletin 2016/06/01, Vol.64(6), pp.632-637
Hauptverfasser: Jung, Jong-Woon, Kim, Jin-Kyung, Jun, Jong-Gab
Format: Artikel
Sprache:eng
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Zusammenfassung:First syntheses of five natural 1,3-diarylpropenes (cinnamylphenols) 2–4, 7, and 8 along with synthesis of two other natural 1,3-diarylpropenes 1 and 5 and E-isomer of mucronulastyrene (6) were achieved by Friedel–Crafts alkylation as a key step. Subsequently, their anti-inflammatory effects were also investigated in lipopolysaccharide (LPS)-induced RAW264.7 macrophages. The compounds exhibited significant inhibition of inflammatory mediated nitric oxide (NO) production with no cytotoxicity except compound 8 (dalberatin B) at 10 µM concentration and IC50 values were found in the range from 4.05 to 16.76 µM.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.c16-00089