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  • Title: Benzoic acid derivatives, acetophenones, and anti-inflammatory constituents from Melicope semecarpifolia.
    Author: Chen JJ, Cho JY, Hwang TL, Chen IS.
    Journal: J Nat Prod; 2008 Jan; 71(1):71-5. PubMed ID: 18163582.
    Abstract:
    Two new benzoic acid derivatives, (E)-3-acetyl-6-(3,7-dimethylocta-2,6-dienyloxy)-2,4-dihydroxybenzoic acid (1) and (E)-3-acetyl-4-(3,7-dimethylocta-2,6-dienyloxy)-2,6-dihydroxybenzoic acid (2), and three new acetophenones, (E)-1-(5-(3,7-dimethylocta-2,6-dienyloxy)-7-hydroxy-2,2-dimethyl-2 H-chromen-8-yl)ethanone (3), (E)-1-(5-(3,7-dimethylocta-2,6-dienyloxy)-7-hydroxy-2-methyl-2-(4-methylpent-3-enyl)-2 H-chromen-8-yl)ethanone (4), and (R,E)-1-(5-(3,7-dimethylocta-2,6-dienyloxy)-3,7-dihydroxy-2,2-dimethylchroman-8-yl)ethanone (5), have been isolated from the fruits of Melicope semecarpifolia, together with eight known compounds. The structures were determined through in-depth NMR and mass spectrometric analyses. Among the isolated compounds, 2-(1'-geranyloxy)-4,6,beta-trihydroxyacetophenone (8), 4-(1'-geranyloxy)-2,6,beta-trihydroxyacetophenone (9), 5-hydroxy-3,7,3',4'-tetramethoxyflavone (10), 5,4'-dihydroxy-3,7,3'-trimethoxyflavone (11), and 5,4'-dihydroxy-3,7-dimethoxyflavone (12) exhibited potent inhibition (IC50<4 microg/mL) on superoxide anion generation and elastase release by human neutrophils in response to fMet-Leu-Phe/cytochalasin B.
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