Abstract
A new limonoid, swietemacrophin (1), was isolated from the seeds of Swietenia macrophylla, together with five known compounds 2-6. The structure of 1 was determined through extensive 1D/2D-NMR and mass-spectrometric analyses. Swietemacrophin (1), humilinolide F (2), 3,6-O,O-diacetylswietenolide (3), 3-O-tigloylswietenolide (4), and swietemahonin E (5) exhibited inhibition (IC50 values≤45.44 μM) of superoxide anion generation by human neutrophils in response to formyl-L-methionyl-L-leucyl-L-phenylalanine (fMLP). Compounds 1, 4, 5, and swietenine (6) showed potent inhibition with IC50 values≤36.32 μM, against lipopolysaccharide (LPS)-induced nitric oxide (NO) generation.
Keywords:
Meliaceae; Swietenia macrophylla; anti-inflammatory activity; limonoid; structure elucidation.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Anti-Inflammatory Agents / chemistry
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Anti-Inflammatory Agents / isolation & purification*
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Anti-Inflammatory Agents / pharmacology
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Humans
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Inhibitory Concentration 50
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Limonins / chemistry
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Limonins / isolation & purification*
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Limonins / pharmacology
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Lipopolysaccharides / antagonists & inhibitors
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Lipopolysaccharides / pharmacology
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Meliaceae / chemistry*
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N-Formylmethionine Leucyl-Phenylalanine / analogs & derivatives
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N-Formylmethionine Leucyl-Phenylalanine / antagonists & inhibitors
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N-Formylmethionine Leucyl-Phenylalanine / pharmacology
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Neutrophils / cytology
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Neutrophils / drug effects
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Neutrophils / metabolism
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Nitric Oxide / antagonists & inhibitors
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Nitric Oxide / biosynthesis
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Plant Extracts / chemistry
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Primary Cell Culture
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Seeds / chemistry*
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Structure-Activity Relationship
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Superoxides / antagonists & inhibitors
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Triterpenes / chemistry
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Triterpenes / isolation & purification*
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Triterpenes / pharmacology
Substances
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Anti-Inflammatory Agents
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Limonins
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Lipopolysaccharides
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Plant Extracts
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Triterpenes
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swietemacrophin
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Superoxides
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Nitric Oxide
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N-Formylmethionine Leucyl-Phenylalanine
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methionyl-leucyl-phenylalanine