Antiallergic Agents from Natural Sources 9. Inhibition of Nitric Oxide Production by Novel Chalcone Derivatives from Mallotus philippinensis (Euphorbiaceae)

Author

Daikonya, A., Katsuki,S. and Kitanaga, S.

Date

2004

Journal

Chem. Pharm. Bull

Three novel chalcone derivatives, mallotophilippens C (1), D (2) and E (3) were isolated from the fruits of Mallotus philippinensis MUELL. ARG. These compounds were identified, using chemical and spectral data, as 1-[6-(3,7-dimethyl-octa-2,6-dienyl)-5,7-dihydroxy-2,2-dimethyl-2H-chromen-8-yl]-3-(4-hydroxy-phenyl)-propenone, 3-(3,4dihydroxyphenyl)-1-[6-(3,7-dimethyl-octa-2,6-dienyl)-5,7-dihydroxy-2,2-dimethyl-2H-chromen-8-yl]-propenone and 1-[5,7-dihydroxy-2-methyl-6-(3-methyl-but-2-enyl)-2-(4-methyl-pent-3-enyl)-2H-chromen-8-yl]-3-(3,4-dihydroxyphenyl)-propenone, respectively. They inhibited nitric oxide (NO) production and inducible NO synthase (iNOS) gene expression by a murine macrophage-like cell line (RAW 264.7), which was activated by lipopolysaccharide (LPS) and recombinant mouse interferon-gamma (IFN-gamma). Furthermore, they downregulated cyclooxygenase-2 (COX-2) gene, interleukin-6 (IL-6) gene and interleukin-1beta (IL-1beta) gene expression. These results suggest that they have anti-inflammatory and immunoregulatory effects.