title: Chemically Induced Cryptic Sesquiterpenoids and Expression of Sesquiterpene Cyclases in Botrytis cinerea Revealed New Sporogenic (+)-4-Epieremophil-9-en-11-ols.
abstract: The sequencing of the genomes of the B05.10 and T4 strains of the fungus Botrytis cinerea revealed an abundance of novel biosynthetic gene clusters, the majority of which were unexpected on the basis of the previous analyses of the fermentation of these and closely related species. By systematic alteration of easy accessible cultivation parameters, using chemical induction with copper sulfate, we have found a cryptic sesquiterpenoid family with new structures related to eremophil-9-ene, which had the basic structure of the sesquiterpene (+)-5-epiaristolochene ((+)-4-epieremophil-9-ene). An expression study of the sesquiterpene cyclase genes present in the Botrytis cinerea genome, under culture conditions, is reported. In general, a 3 day delay and a higher BcSTC genes expression were observed when copper (5 ppm) was fed to the fermentation broth. In addition, to the observed effect on the BcBOT2 (BcSTC1) gene, involved in the biosynthesis of the botrydial toxin, a higher expression level for BcSTC3 and BcSTC4 was observed with respect to the control in the strain B05.10. Interestingly, under copper conditions, the BcSTC4 gene was the most expressed gene in the Botrytis cinerea UCA992 strain. In vitro evaluation of the biological role of these metabolites indicates that they contributed to the conidial development in B. cinerea and appear to be involved in self-regulation of the production of asexual spores. Furthermore, they promoted the formation of complex appressoria or infection cushions.
authors.affiliation: Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Cádiz , Campus Universitario Río San Pedro s/n, Torre sur, 4° planta, 11510, Puerto Real, Cádiz, Spain.
authors.forename: Cristina
authors.initials: C
authors.lastname: Pinedo
authors.affiliation: Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Cádiz , Campus Universitario Río San Pedro s/n, Torre sur, 4° planta, 11510, Puerto Real, Cádiz, Spain.
authors.forename: Javier
authors.initials: J
authors.lastname: Moraga
authors.affiliation: Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Cádiz , Campus Universitario Río San Pedro s/n, Torre sur, 4° planta, 11510, Puerto Real, Cádiz, Spain.
authors.forename: Javier
authors.initials: J
authors.lastname: Barua
authors.affiliation: Departamento de Biomedicina y Biotecnología, Laboratorio de Microbiología, Facultad de Ciencias de Mar y Ambientales, Universidad de Cádiz , 11510, Puerto Real, Spain.
authors.forename: Victoria E
authors.initials: VE
authors.lastname: González-Rodríguez
authors.affiliation: Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Cádiz , Campus Universitario Río San Pedro s/n, Torre sur, 4° planta, 11510, Puerto Real, Cádiz, Spain.
authors.forename: Josefina
authors.initials: J
authors.lastname: Aleu
authors.affiliation: Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Cádiz , Campus Universitario Río San Pedro s/n, Torre sur, 4° planta, 11510, Puerto Real, Cádiz, Spain.
authors.forename: Rosa
authors.initials: R
authors.lastname: Durán-Patrón
authors.affiliation: Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Cádiz , Campus Universitario Río San Pedro s/n, Torre sur, 4° planta, 11510, Puerto Real, Cádiz, Spain.
authors.forename: Antonio J
authors.initials: AJ
authors.lastname: Macías-Sánchez
authors.affiliation: Department of Chemistry, University of Sussex , Brighton, Sussex, BN1 9QJ, United Kingdom.
authors.forename: James R
authors.initials: JR
authors.lastname: Hanson
authors.affiliation: UMR BIOGER , INRA, Avenue Lucien Brétignières, 78850 Grignon, France.
authors.forename: Muriel
authors.initials: M
authors.lastname: Viaud
authors.affiliation: Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Cádiz , Campus Universitario Río San Pedro s/n, Torre sur, 4° planta, 11510, Puerto Real, Cádiz, Spain.
authors.forename: Rosario
authors.initials: R
authors.lastname: Hernández-Galán
authors.affiliation: Departamento de Biomedicina y Biotecnología, Laboratorio de Microbiología, Facultad de Ciencias de Mar y Ambientales, Universidad de Cádiz , 11510, Puerto Real, Spain.
authors.forename: Carlos
authors.initials: C
authors.lastname: Garrido
authors.affiliation: Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Cádiz , Campus Universitario Río San Pedro s/n, Torre sur, 4° planta, 11510, Puerto Real, Cádiz, Spain.
authors.forename: Isidro G
authors.initials: IG
authors.lastname: Collado
mesh_terms: D020171:Botrytis / Q000737:chemistry / Q000235:genetics / Q000378:metabolism*; D019755:Carbon-Carbon Lyases / Q000235:genetics / Q000378:metabolism*; D005285:Fermentation; D005656:Fungal Proteins / Q000235:genetics / Q000378:metabolism*; D016681:Genome, Fungal; D005810:Multigene Family; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes / Q000737:chemistry / Q000378:metabolism*
chemical_list: D005656:Fungal Proteins; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes; C018286:eremophilane compounds; D019755:Carbon-Carbon Lyases; C051130:trichodiene synthetase