Oxidative biosynthesis of phenylbenzoisochromenones from phenylphenalenones.
13C NMR analysis demonstrated incorporation of two 13C labelled phenylalanine units into phenylphenalenones and phenylbenzoisochromenones co-occurring in Wachendorfia thyrsiflora. These results suggest oxidative formation of phenylbenzoisochromenones following a late branching from a common phenylphenalenone biosynthetic pathway. A dioxygenase-type mechanism, followed by decarboxylation, is suggested for the key steps of this conversion.
Opitz
Stefan
S
Max-Planck-Institut für Chemische Okologie, Beutenberg Campus, Winzerlaer Str. 10, D-07745 Jena, Germany.
Schneider
Bernd
B
D002247:Carbon Isotopes; D003500:Cyclization; D003653:Decarboxylation; D006571:Heterocyclic Compounds / Q000737:chemistry* / Q000378:metabolism; D007659:Ketones / Q000737:chemistry* / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008958:Models, Molecular; D010084:Oxidation-Reduction; D010105:Oxygenases / Q000378:metabolism; D043803:Phenalenes; D010649:Phenylalanine / Q000737:chemistry; D011084:Polycyclic Aromatic Hydrocarbons / Q000737:chemistry* / Q000378:metabolism; D011083:Polycyclic Compounds / Q000737:chemistry / Q000378:metabolism; D019862:Zingiberales / Q000737:chemistry / Q000378:metabolism
D002247:Carbon Isotopes; D006571:Heterocyclic Compounds; D007659:Ketones; D043803:Phenalenes; D011084:Polycyclic Aromatic Hydrocarbons; D011083:Polycyclic Compounds; D010649:Phenylalanine; C038036:phenalen-1-one; D010105:Oxygenases