title: Chenopodolans A-C: phytotoxic furopyrans produced by Phoma chenopodiicola, a fungal pathogen of Chenopodium album.
abstract: Three tetrasubstituted furopyrans, named chenopodolans A-C, were isolated together with the well known fungal metabolite (-)-(R)-6-hydroxymellein from the liquid culture of Phoma chenopodiicola, a fungal pathogen proposed for the biological control of Chenopodium album, a common worldwide weed of arable crops. The structures of chenopodolans A-C were established by spectroscopic and chemical methods as 2-(3-methoxy-2,6-dimethyl-7aH-furo[2,3-b]pyran-4-yl)-butane-2,3-diol, 1-(3-methoxy-2,6-dimethyl-7aH-furo[2,3-b]pyran-4-yl)ethanol and 3-methoxy-2,6-dimethyl-4-(1-methylpropenyl)-7aH-furo[2,3-b]pyran, respectively. The absolute configuration R to the hydroxylated secondary carbon (C-11) of the side chain at C-4 of chenopodolan A was determined by applying an advanced Mosher's method. Assayed by leaf puncture on host and non-host weeds chenopodolans A and B, and the 11-O-acetylchenopodolan A showed a strong phytotoxicity. These results showed that the nature of the side chain attached to C-4 is an important feature for the phytotoxicity. A weak zootoxic activity was only showed by chenopodolan B.
authors.affiliation: Dipartimento di Scienze Chimiche, Università di Napoli Federico II, Complesso Universitario Monte S. Angelo, Via Cintia 4, 80126 Napoli, Italy.
authors.forename: Alessio
authors.initials: A
authors.lastname: Cimmino
authors.forename: Anna
authors.initials: A
authors.lastname: Andolfi
authors.forename: Maria Chiara
authors.initials: MC
authors.lastname: Zonno
authors.forename: Fabiana
authors.initials: F
authors.lastname: Avolio
authors.forename: Alexander
authors.initials: A
authors.lastname: Berestetskiy
authors.forename: Maurizio
authors.initials: M
authors.lastname: Vurro
authors.forename: Antonio
authors.initials: A
authors.lastname: Evidente
mesh_terms: D001203:Ascomycota / Q000737:chemistry*; D027463:Chenopodium album / Q000382:microbiology*; D005663:Furans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D015394:Molecular Structure; D009183:Mycotoxins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D018515:Plant Leaves / Q000737:chemistry; D011714:Pyrans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D005663:Furans; D009183:Mycotoxins; D011714:Pyrans; C000588948:chenopodolan A; C000588949:chenopodolan B; C000588950:chenopodolan C
keywords: (−)-(R)-6-Hydroxymellein; Chenopodium album; Chenopodolans A–C; Furopyrans; Herbicides; Phoma chenopodiicola; Phytotoxins