Volume 21, Issue 4, Pages (April 2014)

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Volume 21, Issue 4, Pages 519-529 (April 2014) Molecular and Chemical Characterization of the Biosynthesis of the 6-MSA-Derived Meroterpenoid Yanuthone D in Aspergillus niger Dorte K. Holm, Lene M. Petersen, Andreas Klitgaard, Peter B. Knudsen, Zofia D. Jarczynska, Kristian F. Nielsen, Charlotte H. Gotfredsen, Thomas O. Larsen, Uffe H. Mortensen Chemistry & Biology Volume 21, Issue 4, Pages 519-529 (April 2014) DOI: 10.1016/j.chembiol.2014.01.013 Copyright © 2014 Elsevier Ltd Terms and Conditions

Figure 1 Chemical Structures of 6-MSA and Previously Described Yanuthones (A) Chemical structure of 6-MSA. (B) Chemical structures of previously described yanuthones: yanuthones A–E, 7-deacetoxyyanuthone A, and 22-deacetylyanuthone A (Bugni et al., 2000; Li et al., 2003). Chemistry & Biology 2014 21, 519-529DOI: (10.1016/j.chembiol.2014.01.013) Copyright © 2014 Elsevier Ltd Terms and Conditions

Figure 2 Extracted Ion Chromatograms (A) Extracted ion chromatogram (EIC, m/z 153.0546 ± 0.005) of an A. nidulans reference strain (IBT 29539) and a 6-MSA producing strain (IS1-44965/yanA). (B) Base peak chromatograms (BPC) m/z 100-1,000 of the A. niger reference (KB1001), yanAΔ, and yanRΔ strains. (C) EICs of yanuthone D (1) 503.2640 ± 0.005 (red) and yanuthone E (2) 505.2791 ± 0.005 (black) for KB1001, yanAΔ, and yanRΔ. All chromatograms are to scale. Chemistry & Biology 2014 21, 519-529DOI: (10.1016/j.chembiol.2014.01.013) Copyright © 2014 Elsevier Ltd Terms and Conditions

Figure 3 The Proposed yan Cluster The yanA 6-MSA synthase-encoding gene is flanked by nine cluster genes (yanB, yanC yanD, yanE, yanF, yanG, yanH, yanI, and yanR) whose products contain all necessary activities for conversion of 6-MSA into yanuthone D. Chemistry & Biology 2014 21, 519-529DOI: (10.1016/j.chembiol.2014.01.013) Copyright © 2014 Elsevier Ltd Terms and Conditions

Figure 4 BPC m/z 100–1,000 of Reference Strain KB1001, yanHΔ, yanIΔ, and yanFΔ All NMR-elucidated compounds are shown for comparison of intensity and relative retention times. Below are structures of the yanuthones identified in this study. The structures of yanuthone D (1), yanuthone E (2), 7-deacetoxyyanuthone A (3), and 22-deacetylyanuthone A (6) are shown in Figure 1. Chemistry & Biology 2014 21, 519-529DOI: (10.1016/j.chembiol.2014.01.013) Copyright © 2014 Elsevier Ltd Terms and Conditions

Figure 5 Feeding with Unlabeled m-cresol and Toluquinol Shown are EICs of yanuthone D (1) 503.2640 ± 0.005 (red) and yanuthone E (2) 505.2791 ± 0.005 (black) for KB1001 and the yanAΔ strain with and without feeding. Chromatograms are to scale. Chemistry & Biology 2014 21, 519-529DOI: (10.1016/j.chembiol.2014.01.013) Copyright © 2014 Elsevier Ltd Terms and Conditions

Figure 6 Proposed Biosynthesis of yanuthone D Structures and enzymatic activities in brackets are hypothesized, activities in plain text have been proposed from bioinformatics, and activities in bold have been experimentally verified. Chemistry & Biology 2014 21, 519-529DOI: (10.1016/j.chembiol.2014.01.013) Copyright © 2014 Elsevier Ltd Terms and Conditions