title: Black perithecial pigmentation in Fusarium species is due to the accumulation of 5-deoxybostrycoidin-based melanin.
abstract: Biosynthesis of the black perithecial pigment in the filamentous fungus Fusarium graminearum is dependent on the polyketide synthase PGL1 (oPKS3). A seven-membered PGL1 gene cluster was identified by over-expression of the cluster specific transcription factor pglR. Targeted gene replacement showed that PGL1, pglJ, pglM and pglV were essential for the production of the perithecial pigment. Over-expression of PGL1 resulted in the production of 6-O-demethyl-5-deoxybostrycoidin (1), 5-deoxybostrycoidin (2), and three novel compounds 5-deoxybostrycoidin anthrone (3), 6-O-demethyl-5-deoxybostrycoidin anthrone (4) and purpurfusarin (5). The novel dimeric bostrycoidin purpurfusarin (5) was found to inhibit the growth of Candida albicans with an IC50 of 8.0 +/- 1.9 μM. The results show that Fusarium species with black perithecia have a previously undescribed form of 5-deoxybostrycoidin based melanin in their fruiting bodies.
authors.affiliation: Department for Systems Biology, Technical University of Denmark, DK-2800 Kgs. Lyngby, Denmark.
authors.forename: Rasmus J N
authors.initials: RJ
authors.lastname: Frandsen
authors.affiliation: Department for Systems Biology, Technical University of Denmark, DK-2800 Kgs. Lyngby, Denmark.
authors.forename: Silas A
authors.initials: SA
authors.lastname: Rasmussen
authors.affiliation: Department for Systems Biology, Technical University of Denmark, DK-2800 Kgs. Lyngby, Denmark.
authors.forename: Peter B
authors.initials: PB
authors.lastname: Knudsen
authors.affiliation: Section for Chemistry and Toxicology, Norwegian Veterinary Institute, Oslo, Norway.
authors.forename: Silvio
authors.initials: S
authors.lastname: Uhlig
authors.affiliation: Department of Chemistry, University of Oslo, Oslo, Norway.
authors.forename: Dirk
authors.initials: D
authors.lastname: Petersen
authors.affiliation: Department of Plant Health and Biotechnology, NIBIO - Norwegian Institute of Bioeconomy Research, Høgskoleveien 7, 1430 Ås, Norway.
authors.forename: Erik
authors.initials: E
authors.lastname: Lysøe
authors.affiliation: Department of Chemistry, Technical University of Denmark, DK-2800 Kgs. Lyngby, Denmark.
authors.forename: Charlotte H
authors.initials: CH
authors.lastname: Gotfredsen
authors.affiliation: Department of Chemistry and BioScience, AAU, Fredrik Bajers Vej 7, 9220 Aalborg, Denmark.
authors.forename: Henriette
authors.initials: H
authors.lastname: Giese
authors.affiliation: Department for Systems Biology, Technical University of Denmark, DK-2800 Kgs. Lyngby, Denmark.
authors.forename: Thomas O
authors.initials: TO
authors.lastname: Larsen
mesh_terms: D000935:Antifungal Agents / Q000378:metabolism; D053898:Biosynthetic Pathways / Q000235:genetics; D002176:Candida albicans / Q000187:drug effects / Q000254:growth & development; D005670:Fusarium / Q000235:genetics / Q000378:metabolism*; D015870:Gene Expression; D055786:Gene Knockout Techniques; D005800:Genes, Fungal; D020128:Inhibitory Concentration 50; D007546:Isoquinolines / Q000378:metabolism; D008543:Melanins / Q000096:biosynthesis*; D005810:Multigene Family; D010858:Pigmentation
chemical_list: D000935:Antifungal Agents; D007546:Isoquinolines; D008543:Melanins; C060461:bostrycoidin