title: Fatty acid esters produced by Lasiodiplodia theobromae function as growth regulators in tobacco seedlings.
abstract: The Botryosphaeriaceae are a family of trunk disease fungi that cause dieback and death of various plant hosts. This work sought to characterize fatty acid derivatives in a highly virulent member of this family, Lasiodiplodia theobromae. Nuclear magnetic resonance and gas chromatography-mass spectrometry of an isolated compound revealed (Z, Z)-9,12-ethyl octadecadienoate, (trivial name ethyl linoleate), as one of the most abundant fatty acid esters produced by L. theobromae. A variety of naturally produced esters of fatty acids were identified in Botryosphaeriaceae. In comparison, the production of fatty acid esters in the soil-borne tomato pathogen Fusarium oxysporum, and the non-phytopathogenic fungus Trichoderma asperellum was found to be limited. Ethyl linoleate, ethyl hexadecanoate (trivial name ethyl palmitate), and ethyl octadecanoate, (trivial name ethyl stearate), significantly inhibited tobacco seed germination and altered seedling leaf growth patterns and morphology at the highest concentration (0.2 mg/mL) tested, while ethyl linoleate and ethyl stearate significantly enhanced growth at low concentrations, with both still inducing growth at 98 ng/mL. This work provides new insights into the role of naturally esterified fatty acids from L. theobromae as plant growth regulators with similar activity to the well-known plant growth regulator gibberellic acid.
authors.affiliation: Centro de Investigación Científica y de Educación Superior de Ensenada (CICESE), Carretera Ensenada-Tijuana 3918, Zona Playitas, 22860 Ensenada, B.C., Mexico. Electronic address: curanga@cicese.edu.mx.
authors.forename: Carla C
authors.initials: CC
authors.lastname: Uranga
authors.affiliation: University of California, San Diego, Department of Chemistry and Biochemistry, 9500 Gilman Dr., La Jolla, CA 92093-0358, USA. Electronic address: joris.beld@drexelmed.edu.
authors.forename: Joris
authors.initials: J
authors.lastname: Beld
authors.affiliation: University of California, San Diego, Department of Chemistry and Biochemistry, 9500 Gilman Dr., La Jolla, CA 92093-0358, USA. Electronic address: amrse@ucsd.edu.
authors.forename: Anthony
authors.initials: A
authors.lastname: Mrse
authors.affiliation: Universidad Autónoma de Baja California (UABC), Calzada Universidad 14418 Parque Industrial Internacional Tijuana, Tijuana, B.C. 22390, Mexico. Electronic address: icordova@uabc.edu.mx.
authors.forename: Iván
authors.initials: I
authors.lastname: Córdova-Guerrero
authors.affiliation: University of California, San Diego, Department of Chemistry and Biochemistry, 9500 Gilman Dr., La Jolla, CA 92093-0358, USA. Electronic address: mburkart@ucsd.edu.
authors.forename: Michael D
authors.initials: MD
authors.lastname: Burkart
authors.affiliation: Centro de Investigación Científica y de Educación Superior de Ensenada (CICESE), Carretera Ensenada-Tijuana 3918, Zona Playitas, 22860 Ensenada, B.C., Mexico. Electronic address: ruhernan@cicese.mx.
authors.forename: Rufina
authors.initials: R
authors.lastname: Hernández-Martínez
mesh_terms: D001203:Ascomycota / Q000378:metabolism*; D004305:Dose-Response Relationship, Drug; D004952:Esters / Q000008:administration & dosage; D005227:Fatty Acids / Q000008:administration & dosage*; D010937:Plant Growth Regulators / Q000494:pharmacology*; D036226:Seedlings / Q000187:drug effects / Q000254:growth & development*; D014026:Nicotiana / Q000187:drug effects / Q000254:growth & development*
chemical_list: D004952:Esters; D005227:Fatty Acids; D010937:Plant Growth Regulators
keywords: GC-MS; NMR; Trunk disease fungi