Bioactive lignans from a cultivar of Helianthus annuus.
A bioassay-guided fractionation of water extracts from Helianthus annuus cv. SH-222 was carried out. Ten lignans and a phenylpropanoid were isolated from the polar bioactive fractions of H. annuus. This study is the first to report lignans as constituents of sunflower and is the first time that tanegool has been isolated as a natural aglycone. Additionally, we report biological activities of the isolated compounds. The general bioactivity has been evaluated using the wheat coleoptiles bioassay. The phytotoxic activities of compounds pinoresinol, lariciresinol, dihydro-dehydrodiconiferilic alcohol, and l-(4'-hydroxy-3'-methoxyphenyl)-2-[4' '-(3hydroxypropyl)-2' '-methoxyphenoxy]propane-l,3-diol were also evaluated in a bioassay on the standard target species. The structure-activity relationships are discussed.
Macías
Francisco A
FA
Grupo de Alelopatía, Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Cádiz, Apdo 40, 11510-Puerto Real, Cádiz, Spain. famacias@uca.es
López
Adriana
A
Varela
Rosa M
RM
Torres
Ascensión
A
Molinillo
José M G
JM
D005591:Chemical Fractionation; D006368:Helianthus / Q000737:chemistry*; D017705:Lignans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D008958:Models, Molecular; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry; D012639:Seeds / Q000187:drug effects; D014867:Water
D017705:Lignans; D010936:Plant Extracts; C493882:tanegool; D014867:Water