Abstract
Walsuronoid A (1), a limonoid featuring an unprecedented 3,4-peroxide-bridged A-seco skeleton, together with walsuronoids B (2) and C (3) possessing a rare 18(13-->14)-abeo-limonoid skeleton, was isolated from Walsura robusta. The structures were elucidated by spectroscopic analysis and chemical correlation, and that of 1 was confirmed by single-crystal X-ray diffraction. Biosynthetic pathway of 2 and 3 was proposed and was chemically mimicked. Compounds 1 and 2 showed weak antimalarial activity.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Animals
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Antimalarials / chemistry*
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Antimalarials / isolation & purification
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Antimalarials / pharmacology
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Bridged-Ring Compounds / chemistry*
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Bridged-Ring Compounds / isolation & purification
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Bridged-Ring Compounds / pharmacology
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Crystallography, X-Ray
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Limonins / chemistry*
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Limonins / isolation & purification
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Limonins / pharmacology
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Magnetic Resonance Spectroscopy / methods
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Magnetic Resonance Spectroscopy / standards
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Meliaceae / chemistry*
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Microbial Sensitivity Tests
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Models, Molecular
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Molecular Conformation
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Parasitic Sensitivity Tests
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Peroxides / chemistry*
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Peroxides / isolation & purification
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Peroxides / pharmacology
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Plasmodium falciparum / drug effects
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Reference Standards
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Sensitivity and Specificity
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Stereoisomerism
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Structure-Activity Relationship
Substances
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Antimalarials
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Bridged-Ring Compounds
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Limonins
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Peroxides
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walsuronoid A
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walsuronoid B
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walsuronoid C