title: Isolation of Bioactive Compounds from Sunflower Leaves (Helianthus annuus L.) Extracted with Supercritical Carbon Dioxide.
abstract: The work described herein is a continuation of our initial studies on the supercritical fluid extraction (SFE) with CO2 of bioactive substances from Helianthus annuus L. var. Arianna. The selected SFE extract showed high activity in the wheat coleoptile bioassay, in Petri dish phytotoxicity bioassays, and in the hydroponic culture of tomato seeds. Chromatographic fractionations of the extracts and a spectroscopic analysis of the isolated compounds showed 52 substances belonging to 10 different chemical classes, which were mainly sesquiterpene lactones, diterpenes, and flavonoids. Heliannuol M (31), helivypolides K and L (36, 37), and helieudesmanolide B (38) are described for the first time in the literature. Metabolites have been tested in the etiolated wheat coleoptile bioassay with good results in a noteworthy effect on germination. The most active compounds were also tested on tomato seeds, heliannuol A (30) and leptocarpin (45) being the most active, with values similar to those of the commercial herbicide.
authors.affiliation: †Department of Chemical Engineering and Food Technology and ‡Allelopathy Group, Department of Organic Chemistry, Institute of Biomolecules (INBIO), Campus de Excelencia Internacional (ceiA3), Faculty of Science, University of Cadiz, C/República Saharaui 7, 11510 Puerto Real, Cádiz, Spain.
authors.forename: Zouhir
authors.initials: Z
authors.lastname: El Marsni
authors.affiliation: †Department of Chemical Engineering and Food Technology and ‡Allelopathy Group, Department of Organic Chemistry, Institute of Biomolecules (INBIO), Campus de Excelencia Internacional (ceiA3), Faculty of Science, University of Cadiz, C/República Saharaui 7, 11510 Puerto Real, Cádiz, Spain.
authors.forename: Ascension
authors.initials: A
authors.lastname: Torres
authors.affiliation: †Department of Chemical Engineering and Food Technology and ‡Allelopathy Group, Department of Organic Chemistry, Institute of Biomolecules (INBIO), Campus de Excelencia Internacional (ceiA3), Faculty of Science, University of Cadiz, C/República Saharaui 7, 11510 Puerto Real, Cádiz, Spain.
authors.forename: Rosa M
authors.initials: RM
authors.lastname: Varela
authors.affiliation: †Department of Chemical Engineering and Food Technology and ‡Allelopathy Group, Department of Organic Chemistry, Institute of Biomolecules (INBIO), Campus de Excelencia Internacional (ceiA3), Faculty of Science, University of Cadiz, C/República Saharaui 7, 11510 Puerto Real, Cádiz, Spain.
authors.forename: José M G
authors.initials: JM
authors.lastname: Molinillo
authors.affiliation: †Department of Chemical Engineering and Food Technology and ‡Allelopathy Group, Department of Organic Chemistry, Institute of Biomolecules (INBIO), Campus de Excelencia Internacional (ceiA3), Faculty of Science, University of Cadiz, C/República Saharaui 7, 11510 Puerto Real, Cádiz, Spain.
authors.forename: Lourdes
authors.initials: L
authors.lastname: Casas
authors.affiliation: †Department of Chemical Engineering and Food Technology and ‡Allelopathy Group, Department of Organic Chemistry, Institute of Biomolecules (INBIO), Campus de Excelencia Internacional (ceiA3), Faculty of Science, University of Cadiz, C/República Saharaui 7, 11510 Puerto Real, Cádiz, Spain.
authors.forename: Casimiro
authors.initials: C
authors.lastname: Mantell
authors.affiliation: †Department of Chemical Engineering and Food Technology and ‡Allelopathy Group, Department of Organic Chemistry, Institute of Biomolecules (INBIO), Campus de Excelencia Internacional (ceiA3), Faculty of Science, University of Cadiz, C/República Saharaui 7, 11510 Puerto Real, Cádiz, Spain.
authors.forename: Enrique J
authors.initials: EJ
authors.lastname: Martinez de la Ossa
authors.affiliation: †Department of Chemical Engineering and Food Technology and ‡Allelopathy Group, Department of Organic Chemistry, Institute of Biomolecules (INBIO), Campus de Excelencia Internacional (ceiA3), Faculty of Science, University of Cadiz, C/República Saharaui 7, 11510 Puerto Real, Cádiz, Spain.
authors.forename: Francisco A
authors.initials: FA
authors.lastname: Macias
mesh_terms: D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000494:pharmacology; D025924:Chromatography, Supercritical Fluid; D004224:Diterpenes / Q000032:analysis / Q000737:chemistry / Q000494:pharmacology; D005419:Flavonoids / Q000032:analysis / Q000737:chemistry / Q000494:pharmacology; D018525:Germination / Q000187:drug effects; D006368:Helianthus / Q000737:chemistry*; D006540:Herbicides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D007783:Lactones / Q000032:analysis / Q000737:chemistry / Q000494:pharmacology; D018551:Solanum lycopersicum / Q000187:drug effects; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry*; D018515:Plant Leaves / Q000737:chemistry*; D012639:Seeds / Q000254:growth & development; D012717:Sesquiterpenes / Q000032:analysis / Q000737:chemistry / Q000494:pharmacology
chemical_list: D019086:Bridged Bicyclo Compounds, Heterocyclic; D004224:Diterpenes; D005419:Flavonoids; D006540:Herbicides; D007783:Lactones; D010936:Plant Extracts; D012717:Sesquiterpenes; C476207:heliannuol A; C093534:leptocarpin
keywords: Helianthus annuus L.; bioactive compounds; cytotoxicity and phytoxicity bioassays; flavonoids; heliannuol; sesquiterpene lactones; supercritical carbon dioxide