Microbial transformation of 1,8-dihydroxy-9,10-anthraquinone

Microbial Transformation of Amino- and Hydroxyanthraquinones by Beauveria bassiana ATCC 7159

“…Previous studies on microbial glucosylation of 1-and 2-hydroxyanthraquinones with Streptomyces aureofaciens have been reported to result in their corresponding β-D-glucosides in poor yields. 6 In a recent study, Zhang et al 7 screened 21 microbial strains for their ability to glucosylate anthraquinones of rhubarb and found that only Absidia coerulea was capable of converting these anthraquinones into their corresponding O-glucosides in yields of 6-14%. We and others 8 have previously utilized the microbial strain BeauVeria bassiana ATCC 7159 for efficient 4′-O-methyl-glucosylation of a number of phenolic natural products.…”

“…Although microbial O -glycosylation of phenols is well documented, this constitutes the first report of N -glycosylation of an aromatic amine by microbial biotransformation. Previous studies on microbial glucosylation of 1- and 2-hydroxyanthraquinones with Streptomyces aureofaciens have been reported to result in their corresponding β- d -glucosides in poor yields . In a recent study, Zhang et al screened 21 microbial strains for their ability to glucosylate anthraquinones of rhubarb and found that only Absidia coerulea was capable of converting these anthraquinones into their corresponding O -glucosides in yields of 6−14%.…”

Access to 1,2,3,4-Tetraoxygenated Benzenes via a Double Baeyer–Villiger Reaction of Quinizarin Dimethyl Ether: Application to the Synthesis of Bioactive Natural Products from Antrodia camphorata

“…To the best of our knowledge, and somewhat surprisingly, there are only two reported examples of Baeyer−Villiger reactions of anthraquinones. Microbial transformation of chrysazin (6) gave the oxepine lactone 7 (Scheme 3), 15 a reaction that would be very difficult to replicate through chemical (as opposed to enzymatic) means, since oxygen insertion occurs at the least electron rich site. Treatment of anthraquinone (8) with peroxytrifluoroacetic acid was reported to give a "very low yield" of dibenzo[b,f ]- [1,4]dioxocine-6,11-dione (10).…”

“…5-Bromo-4,7-dimethoxy-6-methyl-1,3-benzodioxole (15). A solution of Br 2 (25 μL, 0.49 mmol) in DCM (1 mL) was added dropwise to a stirred solution of 4 (87 mg, 0.44 mmol) in DCM (2 mL) at 0 °C.…”