Sesquiterpene lactones as allelochemicals.
Six new sesquiterpene lactones, annuolide H (3), helivypolides F, H-J (4, 11-13), and helieudesmanolide A (6), together with known compounds, were isolated from polar bioactive fractions of Helianthus annuus cv. SH-222 and Stella fresh leaf water extracts. Spectroscopic analysis of the new data for 1,2-anhydroniveusin A and 1-methoxy-4,5-dihydroniveusin A corrects some previous assignments. The compounds were tested using the etiolated wheat coleoptile bioassay, and the most active compounds were assayed in standard target species (STS) (Lepidium sativum, Allium cepa, Lactucasativa, Lycopersicon esculentum, and Triticum aestivum) from 5 x 10(-4) to 10(-5) M. The most phytotoxic compounds were helivypolide F and 15-hydroxy-3-dehydrodeoxyfruticin, both of which have a carbonyl group at C-3 conjugated with two double bonds.
Macías
Francisco A
FA
Grupo de Alelopatía, Departamento de Química Organica, Facultad de Ciencias, Universidad de Cadiz, 11510 Puerto Real, Spain. famacias@uca.es
Fernández
Adriana
A
Varela
Rosa M
RM
Molinillo
José M G
JM
Torres
Ascensión
A
Alves
Pedro L C A
PL
D006368:Helianthus / Q000737:chemistry*; D007783:Lactones / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D018545:Lactuca / Q000187:drug effects; D018551:Solanum lycopersicum / Q000187:drug effects; D015394:Molecular Structure; D019697:Onions / Q000187:drug effects; D018515:Plant Leaves / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D013030:Spain; D013329:Structure-Activity Relationship; D014908:Triticum / Q000187:drug effects
D007783:Lactones; D012717:Sesquiterpenes