title: Limonoids of the phragmalin type from Swietenia macrophylla and their chemotaxonomic significance.
abstract: 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.
authors.affiliation: Instituto de Ciencias Exatas e Naturais, Faculdade de Quimica, Universidade Federal do Para, 66075-110 Belem, PA, Brazil.
authors.forename: Milton Nascimento
authors.initials: MN
authors.lastname: da Silva
authors.forename: Mara Silvia Pinheiro
authors.initials: MS
authors.lastname: Arruda
authors.forename: Kelly Christina F
authors.initials: KC
authors.lastname: Castro
authors.forename: M Fátima das G F
authors.initials: MF
authors.lastname: da Silva
authors.forename: João B
authors.initials: JB
authors.lastname: Fernandes
authors.forename: Paulo C
authors.initials: PC
authors.lastname: Vieira
mesh_terms: 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
chemical_list: D036701:Limonins