title: Phytotoxins from Tithonia diversifolia.
abstract: Tithonia diversifolia (Mexican sunflower) is a dominant plant of the Asteraceae family, which suggests it produces allelochemicals that interfere with the development of surrounding plants. The study described herein was conducted to identify the compounds that have phytotoxic activity in T. diversifolia extracts. Ethyl acetate extracts of the leaves, stems, and roots showed significant inhibition of wheat coleoptile growth, and the leaf extract had similar inhibitory effects to a commercial herbicide. Fourteen compounds, 12 of which were sesquiterpene lactones, have been isolated. Two sesquiterpene lactones are reported for the first time and were isolated as an inseparable mixture of 8β-O-(2-methylbutyroyl)tirotundin (4) and 8β-O-(isovaleroyl)tirotundin (5). Their structures were determined by spectroscopic analysis, including NMR techniques and mass spectrometry. The sesquiterpene lactones 1β-methoxydiversifolin (6), tagitinin A (7), and tagitinin C (8) were the major products identified. These compounds were active on etiolated wheat coleoptiles, seed germination, and the growth of STS and weeds. The phytotoxic activity shown by these sesquiterpene lactones indicates that they are the compounds responsible for the activity exhibited by the initial extracts.
authors: ‡Departamento de Botânica, Universidade Federal de São Carlos, 13565905-São Carlos, São Paulo, Brazil.
authors: Maria A F M
authors: MA
authors: Miranda
authors: †Grupo de Alelopatía, Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Cádiz, Campus de Excelencia Internacional Agroalimentario, ceiA3, Instituto de Biomoleculas (INBIO), C/República Saharaui n, 7, 11510-Puerto Real, Cádiz, Spain.
authors: Rosa M
authors: RM
authors: Varela
authors: †Grupo de Alelopatía, Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Cádiz, Campus de Excelencia Internacional Agroalimentario, ceiA3, Instituto de Biomoleculas (INBIO), C/República Saharaui n, 7, 11510-Puerto Real, Cádiz, Spain.
authors: Ascension
authors: A
authors: Torres
authors: †Grupo de Alelopatía, Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Cádiz, Campus de Excelencia Internacional Agroalimentario, ceiA3, Instituto de Biomoleculas (INBIO), C/República Saharaui n, 7, 11510-Puerto Real, Cádiz, Spain.
authors: José M G
authors: JM
authors: Molinillo
authors: ‡Departamento de Botânica, Universidade Federal de São Carlos, 13565905-São Carlos, São Paulo, Brazil.
authors: Sonia C J
authors: SC
authors: Gualtieri
authors: †Grupo de Alelopatía, Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Cádiz, Campus de Excelencia Internacional Agroalimentario, ceiA3, Instituto de Biomoleculas (INBIO), C/República Saharaui n, 7, 11510-Puerto Real, Cádiz, Spain.
authors: Francisco A
authors: FA
authors: Macías
mesh_terms: D019659:Asteraceae / Q000737:chemistry*; D001938:Brazil; D007783:Lactones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010936:Plant Extracts / Q000494:pharmacology*; D018515:Plant Leaves / Q000737:chemistry; D018517:Plant Roots / Q000737:chemistry; D018547:Plant Stems / Q000737:chemistry; D057685:Plant Weeds / Q000187:drug effects; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*
chemical_list: D007783:Lactones; D010936:Plant Extracts; D012717:Sesquiterpenes; C115942:tirotundin; C012565:tagitinin