title: Aryl Polyenes, a Highly Abundant Class of Bacterial Natural Products, Are Functionally Related to Antioxidative Carotenoids.
abstract: Bacterial pigments of the aryl polyene type are structurally similar to the well-known carotenoids with respect to their polyene systems. Their biosynthetic gene cluster is widespread in taxonomically distant bacteria, and four classes of such pigments have been found. Here we report the structure elucidation of the aryl polyene/dialkylresorcinol hybrid pigments of Variovorax paradoxus B4 by HPLC-UV-MS, MALDI-MS and NMR. Furthermore, we show for the first time that this pigment class protects the bacterium from reactive oxygen species, similarly to what is known for carotenoids. An analysis of the distribution of biosynthetic genes for aryl polyenes and carotenoids in bacterial genomes is presented; it shows a complementary distribution of these protective pigments in bacteria.
authors.affiliation: Merck Stiftungsprofessur für Molekulare Biotechnologie, Fachbereich Biowissenschaften, Goethe Universität Frankfurt, Max-von-Laue Strasse 9, 60438, Frankfurt am Main, Germany.
authors.forename: Tim A
authors.initials: TA
authors.lastname: Schöner
authors.affiliation: Biosynthesis Group, Fachbereich Biowissenschaften, Goethe Universität Frankfurt, Max-von-Laue-Strasse 9, 60438, Frankfurt am Main, Germany.
authors.forename: Sören
authors.initials: S
authors.lastname: Gassel
authors.affiliation: Japan Women's University, 2-8-1, Mejirodai, Bunkyo-ku, Tokyo, 112-8681, Japan.
authors.forename: Ayako
authors.initials: A
authors.lastname: Osawa
authors.affiliation: Merck Stiftungsprofessur für Molekulare Biotechnologie, Fachbereich Biowissenschaften, Goethe Universität Frankfurt, Max-von-Laue Strasse 9, 60438, Frankfurt am Main, Germany.
authors.forename: Nicholas J
authors.initials: NJ
authors.lastname: Tobias
authors.affiliation: Japan Women's University, 2-8-1, Mejirodai, Bunkyo-ku, Tokyo, 112-8681, Japan.
authors.forename: Yukari
authors.initials: Y
authors.lastname: Okuno
authors.affiliation: Japan Women's University, 2-8-1, Mejirodai, Bunkyo-ku, Tokyo, 112-8681, Japan.
authors.forename: Yui
authors.initials: Y
authors.lastname: Sakakibara
authors.affiliation: Japan Women's University, 2-8-1, Mejirodai, Bunkyo-ku, Tokyo, 112-8681, Japan.
authors.forename: Kazutoshi
authors.initials: K
authors.lastname: Shindo
authors.affiliation: Biosynthesis Group, Fachbereich Biowissenschaften, Goethe Universität Frankfurt, Max-von-Laue-Strasse 9, 60438, Frankfurt am Main, Germany.
authors.forename: Gerhard
authors.initials: G
authors.lastname: Sandmann
authors.affiliation: Merck Stiftungsprofessur für Molekulare Biotechnologie, Fachbereich Biowissenschaften, Goethe Universität Frankfurt, Max-von-Laue Strasse 9, 60438, Frankfurt am Main, Germany. h.bode@bio.uni-frankfurt.de.|Buchmann Institute for Molecular Life Sciences (BMLS), Goethe Universität Frankfurt, Max-von-Laue-Strasse 15, 60438, Frankfurt am Main, Germany. h.bode@bio.uni-frankfurt.de.
authors.forename: Helge B
authors.identifier: http://orcid.org/0000-0001-6048-5909
authors.initials: HB
authors.lastname: Bode
mesh_terms: D000975:Antioxidants / Q000737:chemistry / Q000378:metabolism*; D001426:Bacterial Proteins / Q000145:classification / Q000235:genetics / Q000378:metabolism; D001688:Biological Products / Q000737:chemistry / Q000378:metabolism*; D002338:Carotenoids / Q000737:chemistry / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid; D042621:Comamonadaceae / Q000235:genetics / Q000378:metabolism*; D016680:Genome, Bacterial; D005810:Multigene Family; D016296:Mutagenesis; D010802:Phylogeny; D011090:Polyenes / Q000737:chemistry / Q000378:metabolism*; D017382:Reactive Oxygen Species / Q000378:metabolism; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
chemical_list: D000975:Antioxidants; D001426:Bacterial Proteins; D001688:Biological Products; D011090:Polyenes; D017382:Reactive Oxygen Species; D002338:Carotenoids
keywords: antioxidants; aryl polyenes; carotenoids; dialkylresorcinols; dyes/pigments; natural products