title: Megalanthine, a bioactive sesquiterpenoid from Heliotropium megalanthum, its degradation products and their bioactivities.
abstract: The new bioactive sesquiterpenoid (3R,6E)-2,6,10-trimethyl-3-(3-p-hydroxyphenylpropanoyloxy)-dodeca-6,11-diene-2,10-diol, named megalanthine, was isolated from the resinous exudates of Heliotropium megalanthum. The degradation products of this compound were identified. Several plant-defensive properties (insecticidal, antifungal, and phytotoxic) were evaluated after obtaining positive results in a preliminary etiolated wheat coleoptile bioassay. This bioassay showed the need to have both the phenolic and sesquiterpene moieties of the natural product present to achieve a biological effect. This result was confirmed in phytotoxicity bioassays. Megalanthine was ruled out as a significant plant-plant defense agent because of its lack of stability. The positive results recorded in the antifungal and antifeedant tests suggest, however, that this chemical is relevant in several ecological interactions involving H. megalanthum.
authors.affiliation: Departamento de Química Orgánica, Universidad de Cádiz, Puerto Real, Spain. famacias@uca.es.
authors.forename: Francisco A
authors.initials: FA
authors.lastname: Macías
authors.forename: Ana M
authors.initials: AM
authors.lastname: Simonet
authors.forename: Brigida
authors.initials: B
authors.lastname: D'Abrosca
authors.forename: Claudia C
authors.initials: CC
authors.lastname: Maya
authors.forename: Matías
authors.initials: M
authors.lastname: Reina
authors.forename: Azucena
authors.initials: A
authors.lastname: González-Coloma
authors.forename: Raimundo
authors.initials: R
authors.lastname: Cabrera
authors.forename: Cristina
authors.initials: C
authors.lastname: Giménez
authors.forename: Luis
authors.initials: L
authors.lastname: Villarroel
mesh_terms: D000818:Animals; D000935:Antifungal Agents / Q000302:isolation & purification* / Q000378:metabolism / Q000494:pharmacology; D001681:Biological Assay; D016466:CHO Cells; D002478:Cells, Cultured; D018548:Cotyledon / Q000187:drug effects / Q000254:growth & development; D006224:Cricetinae; D003412:Cricetulus; D005658:Fungi / Q000187:drug effects / Q000254:growth & development; D028162:Heliotropium / Q000737:chemistry*; D007306:Insecticides / Q000302:isolation & purification* / Q000378:metabolism / Q000494:pharmacology; D018545:Lactuca / Q000187:drug effects / Q000254:growth & development; D018551:Solanum lycopersicum / Q000187:drug effects / Q000254:growth & development; D008826:Microbial Sensitivity Tests; D019697:Onions / Q000187:drug effects / Q000254:growth & development; D010666:Phenylpropionates / Q000302:isolation & purification* / Q000378:metabolism / Q000494:pharmacology*; D018517:Plant Roots / Q000187:drug effects / Q000254:growth & development; D012639:Seeds / Q000187:drug effects / Q000254:growth & development; D014908:Triticum / Q000187:drug effects / Q000254:growth & development
chemical_list: C540652:2,6,10-trimethyl-3-(3-p-hydroxyphenylpropanoyloxy)-dodeca-6,11-diene-2,10-diol; D000935:Antifungal Agents; D007306:Insecticides; D010666:Phenylpropionates