title: Simiranes A and B: erythroxylanes diterpenes and other compounds from Simira eliezeriana (Rubiaceae).
abstract: The first phytochemical study of Simira eliezeriana Peixoto (Rubiaceae) allowed the isolation and structural determination of two new diterpenes named simirane A [(5R,6R,8R,9R,10S,11S,13S)-6β,11β-dihydroxy-2,4(18),15-erythroxylatrien-1-one] (1) and simirane B [(5S,8R,9R,10S,11S,13S)-11β-hydroxy-2,4(18),15-erythroxylatrien-1-one] (2), together with seven known compounds: sitosterol (3), stigmasterol (4), campesterol (5), coniferaldehyde (6), vanillin (7), pinoresinol (8) and harman (9) from the bark of the plant. The structures of the compounds were established on the basis of spectroscopic methods, including 1-D and 2-D NMR, HRESI-MS and CD analysis and comparisons with available literature data of known compounds.
authors.affiliation: Laboratório de Química de Produtos Naturais, Departamento de Química, ICE-Universidade Federal Rural do Rio de Janeiro, UFRRJ, BR 465 KM.07, 23890-000, Seropédica-RJ, Brazil. mfaaraujo@gmail.com
authors.forename: Marcelo F
authors.initials: MF
authors.lastname: de Araújo
authors.forename: Ivo J
authors.initials: IJ
authors.lastname: Curcino Vieira
authors.forename: Raimundo
authors.initials: R
authors.lastname: Braz-Filho
authors.forename: Mário G
authors.initials: MG
authors.lastname: de Carvalho
mesh_terms: D000171:Acrolein / Q000031:analogs & derivatives / Q000302:isolation & purification; D001547:Benzaldehydes / Q000302:isolation & purification; D002784:Cholesterol / Q000031:analogs & derivatives / Q000302:isolation & purification; D004224:Diterpenes / Q000032:analysis / Q000737:chemistry / Q000302:isolation & purification*; D000431:Ethanol; D005663:Furans / Q000302:isolation & purification; D006247:Harmine / Q000031:analogs & derivatives / Q000302:isolation & purification; D017705:Lignans / Q000302:isolation & purification; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010840:Phytosterols / Q000302:isolation & purification; D024301:Plant Bark / Q000737:chemistry*; D010936:Plant Extracts / Q000032:analysis / Q000737:chemistry / Q000302:isolation & purification*; D019666:Rubiaceae / Q000737:chemistry*; D012855:Sitosterols / Q000302:isolation & purification
chemical_list: D001547:Benzaldehydes; D004224:Diterpenes; D005663:Furans; D017705:Lignans; D010840:Phytosterols; D010936:Plant Extracts; D012855:Sitosterols; C075384:coniferaldehyde; D000431:Ethanol; D006247:Harmine; C021273:campesterol; C025473:gamma-sitosterol; D000171:Acrolein; C005010:harman; D002784:Cholesterol; C100058:vanillin; C103298:pinoresinol