The structure of canescin

Recent advances in the discovery, biosynthesis, and therapeutic potential of isocoumarins derived from fungi: a comprehensive update

“…at a concentration of 5 mg mL −1 with an inhibition zone of 19.7 mm. 71 Six dihydroisocoumarins derivatives including the previously mentioned asperentin (39), 5 ′ -hydroxyasperentin (40), 4 ′ - hydroxyasperentin (41), asperentin-8-methyl ether (42), along with two previously undescribed derivatives, including cladosporin 8-O-a-ribofuranoside (48), and asperentin 6-O-methyl ether (49) (Fig. 9), were obtained from EtOAc extract of the marine-derived fungi Aspergillus sp.…”

“…39,40 The biosynthetic pathway of isocoumarin derivates had been studied by Birch's group. 41,42 Their study investigated the biosynthesis of canescin from Penicillium canescens using stable isotopes ( 13 C labelled) and NMR spectroscopy to determine the sites of incorporation. They pointed out that the isocoumarin portion of the canescin molecule was generated through the acetate/malonate pathway.…”

“…They pointed out that the isocoumarin portion of the canescin molecule was generated through the acetate/malonate pathway. 42,43 Indeed, Birch et al, discovered that canescin's C- 10 and C-14 were generated from methionine. Further study by Lewis's group conrmed canescin biosynthesis using the feeding experiment of [ 13 C,2H 3 ] methionine that was administered to Aspergillus malignus using batch-wise method over 5 days of incubation.…”

Recent Advances in Discovery, Biosynthesis and Therapeutic Potentialities of Isocoumarins Derived from Fungi: A Comprehensive Update

“…Isocoumarin is a well-known polyketide that had been biosynthesized by the polyketide synthase (PKS) pathway 38,39 . The biosynthetic pathway of isocoumarin derivates had been studied by Birch's group 40,41 . Their study investigated the biosynthesis of canescin from Penicillium canescens using stable isotopes ( 13 C labelled) and NMR spectroscopy to determine sites of incorporation.…”

“…Their study investigated the biosynthesis of canescin from Penicillium canescens using stable isotopes ( 13 C labelled) and NMR spectroscopy to determine sites of incorporation. They pointed out that the isocoumarin portion of the canescin molecule being generated through the acetate/malonate pathway 41,42 . Indeed, Birch et al, discovered that canescin's C-10 and C-14 are generated from methionine.…”