title: Isolation and identification of precocenes and piperitone from essential oils as specific inhibitors of trichothecene production by Fusarium graminearum.
abstract: Inhibitors of deoxynivalenol production by Fusarium graminearum are useful for protecting crops from deoxynivalenol contamination. We isolated precocenes and piperitone from the essential oils of Matricaria recutita and Eucalyptus dives, respectively, as specific inhibitors of the production of 3-acetyldeoxynivalenol, a biosynthetic precursor of deoxynivalenol. Precocenes I and II and piperitone inhibited 3-acetyldeoxynivalenol production by F. graminearum in a liquid culture with IC(50) values of 16.6, 1.2, and 306 microM, respectively, without inhibiting fungal growth. Precocene II also inhibited deoxynivalenol production by the fungus in a solid culture on rice with an IC(50) value of 2.0 ppm. Precocene II and piperitone decreased the mRNA levels of Tri4, Tri5, Tri6, and Tri10 encoding proteins required for deoxynivalenol biosynthesis.
authors.affiliation: Department of Applied Biological Chemistry, The University of Tokyo, Tokyo, Japan.
authors.forename: Atsushi
authors.initials: A
authors.lastname: Yaguchi
authors.forename: Tomoya
authors.initials: T
authors.lastname: Yoshinari
authors.forename: Rie
authors.initials: R
authors.lastname: Tsuyuki
authors.forename: Haruo
authors.initials: H
authors.lastname: Takahashi
authors.forename: Takashi
authors.initials: T
authors.lastname: Nakajima
authors.forename: Yoshiko
authors.initials: Y
authors.lastname: Sugita-Konishi
authors.forename: Hiromichi
authors.initials: H
authors.lastname: Nagasawa
authors.forename: Shohei
authors.initials: S
authors.lastname: Sakuda
mesh_terms: D001578:Benzopyrans / Q000302:isolation & purification / Q000494:pharmacology*; D000081005:Cyclohexane Monoterpenes; D005052:Eucalyptus / Q000737:chemistry; D005670:Fusarium / Q000187:drug effects / Q000378:metabolism*; D015870:Gene Expression / Q000187:drug effects; D031168:Matricaria / Q000737:chemistry; D039821:Monoterpenes / Q000302:isolation & purification / Q000494:pharmacology*; D009822:Oils, Volatile / Q000737:chemistry*; D014255:Trichothecenes / Q000037:antagonists & inhibitors* / Q000096:biosynthesis / Q000235:genetics
chemical_list: D001578:Benzopyrans; D000081005:Cyclohexane Monoterpenes; D039821:Monoterpenes; D009822:Oils, Volatile; D014255:Trichothecenes; C496656:piperitone; C014163:precocene II; C019539:precocene I; C007262:deoxynivalenol