Limonoids of the phragmalin type from Swietenia macrophylla and their chemotaxonomic significance.
Species of Swietenia elaborate limonoid chemistry along only one route, which leads to the mexicanolide type in most species and the phragmalin type in S. mahogani. A hexane extract from leaves of S. macrophylla afforded six new phragmalins with a 8,9,30-ortho-ester unit, namely, 6-O-acetylswietephragmin E (1), 3beta-O-destigloyl-3beta-O-benzoyl-6-O-acetylswietephragmin E (2), 12alpha-acetoxyswietephragmin C (3), 3beta-O-destigloyl-3beta-O-benzoyl-12alpha-acetoxyswietephragmin C (4), 12alpha-acetoxyswietephragmin D (5), and 3beta-O-destigloyl-3beta-O-benzoyl-12alpha-acetoxyswietephragmin D (6). This appears to be the first record of phragamalins from S. macrophylla, and this study shows the potential of tricyclic [3.3.1(2,10).1(1,4)]-decane limonoids as taxonomically useful chemical markers in the Meliaceae.
da Silva
Milton Nascimento
MN
Instituto de Ciencias Exatas e Naturais, Faculdade de Quimica, Universidade Federal do Para, 66075-110 Belem, PA, Brazil.
Arruda
Mara Silvia Pinheiro
MS
Castro
Kelly Christina F
KC
da Silva
M Fátima das G F
MF
Fernandes
João B
JB
Vieira
Paulo C
PC
D001938:Brazil; D036701:Limonins / Q000737:chemistry* / Q000145:classification / Q000302:isolation & purification*; D029582:Meliaceae / Q000737:chemistry* / Q000235:genetics; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D018515:Plant Leaves / Q000737:chemistry
D036701:Limonins