title: Botrytone, a new naphthalenone pentaketide produced by Botrytis fabae, the causal agent of chocolate spot disease on Vicia faba.
abstract: A strain of Botrytis fabae isolated from faba bean (Vicia faba L.) plants displaying clear chocolate spot disease symptoms produced phytotoxic metabolites in vitro. The phytotoxins isolated from the culture filtrate organic extract were characterized by spectroscopic and optical methods. A new naphthalenone pentaketide, named botrytone, was isolated and characterized as (4R)-3,4-dihydro-4,5,8-trihydroxy-1(2H)-naphthalenone together with other well-known closely related naphthalenones such as regiolone and cis- and trans-3,4-dihydro-2,4,8-trihydroxynaphthalen-1(2H)-ones. When tested on leaves of the host plant, with the cis- and trans-3,4-dihydro-2,4,8-trihydroxynaphthalen-1(2H)-ones assayed in mixture, regiolone demonstrated the highest level of phytotoxicity together with cis- and trans-3,4-dihydro-2,4,8-trihydroxynaphthalen-1(2H)-ones. Botrytone showed moderate phytotoxic activity at 1 mg/mL and was still phytotoxic at 0.5 mg/mL.
authors.affiliation: Institute for Sustainable Agriculture, CSIC, Apartado 4084, 14080 Córdoba, Spain.
authors.forename: Alessio
authors.initials: A
authors.lastname: Cimmino
authors.forename: Angel M
authors.initials: AM
authors.lastname: Villegas-Fernández
authors.forename: Anna
authors.initials: A
authors.lastname: Andolfi
authors.forename: Dominique
authors.initials: D
authors.lastname: Melck
authors.forename: Diego
authors.initials: D
authors.lastname: Rubiales
authors.forename: Antonio
authors.initials: A
authors.lastname: Evidente
mesh_terms: D020171:Botrytis / Q000378:metabolism*; D003517:Cyclopentanes / Q000302:isolation & purification / Q000378:metabolism* / Q000494:pharmacology; D006540:Herbicides / Q000378:metabolism / Q000494:pharmacology; D010935:Plant Diseases / Q000382:microbiology*; D031307:Vicia faba / Q000382:microbiology*
chemical_list: D003517:Cyclopentanes; D006540:Herbicides; C518561:botrytinone