Benzoic acid derivatives, acetophenones, and anti-inflammatory constituents from Melicope semecarpifolia.
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.
Chen
Jih-Jung
JJ
Graduate Institute of Pharmaceutical Technology, Tajen University, Pingtung, Taiwan, Republic of China. jjchen@mail.tajen.edu.tw
Cho
Jui-Ying
JY
Hwang
Tsong-Long
TL
Chen
Ih-Sheng
IS
D000098:Acetophenones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D001565:Benzoates / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D006801:Humans; D015394:Molecular Structure; D009240:N-Formylmethionine Leucyl-Phenylalanine; D009504:Neutrophils / Q000187:drug effects; D010196:Pancreatic Elastase / Q000032:analysis / Q000096:biosynthesis / Q000187:drug effects; D010946:Plants, Medicinal / Q000737:chemistry*; D027821:Rutaceae / Q000737:chemistry*; D013481:Superoxides / Q000037:antagonists & inhibitors; D013624:Taiwan
D000098:Acetophenones; D000894:Anti-Inflammatory Agents, Non-Steroidal; D001565:Benzoates; D013481:Superoxides; D009240:N-Formylmethionine Leucyl-Phenylalanine; D010196:Pancreatic Elastase