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The first limonoid peroxide in the Meliaceae family: walsuronoid A from Walsura robusta.
- Source :
-
Organic letters [Org Lett] 2007 Jun 07; Vol. 9 (12), pp. 2353-6. Date of Electronic Publication: 2007 May 16. - Publication Year :
- 2007
-
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.
- Subjects :
- Animals
Antimalarials isolation & purification
Antimalarials pharmacology
Bridged-Ring Compounds isolation & purification
Bridged-Ring Compounds pharmacology
Crystallography, X-Ray
Limonins isolation & purification
Limonins pharmacology
Magnetic Resonance Spectroscopy methods
Magnetic Resonance Spectroscopy standards
Microbial Sensitivity Tests
Models, Molecular
Molecular Conformation
Parasitic Sensitivity Tests
Peroxides isolation & purification
Peroxides pharmacology
Plasmodium falciparum drug effects
Reference Standards
Sensitivity and Specificity
Stereoisomerism
Structure-Activity Relationship
Antimalarials chemistry
Bridged-Ring Compounds chemistry
Limonins chemistry
Meliaceae chemistry
Peroxides chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 1523-7060
- Volume :
- 9
- Issue :
- 12
- Database :
- MEDLINE
- Journal :
- Organic letters
- Publication Type :
- Academic Journal
- Accession number :
- 17503836
- Full Text :
- https://doi.org/10.1021/ol070735+