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

Abstract

Microbial biotransformation of four amino- and hydroxyanthraquinones catalyzed by Beauveria bassiana ATCC 7159 has been studied. Incubation of 1,2-diaminoanthraquinone (1) with B. bassiana ATCC 7159 afforded 1-amino-2-(4'-O-methyl-2beta-N-D-glucopyranosylamino)anthraquinone (5) in a hitherto unprecedented biotransformation involving N-glycosylation of an amine. Biotransformation of 1-aminoanthraquinone (2) yielded 1-amino-2-(4'-O-methyl-2beta-O-D-glucopyranosyloxy)anthraquinone (6) as a result of microbial hydroxylation of C-2 followed by 4'-O-methyl-glucosylation of the newly introduced hydroxyl group. 1,8-Dihydroxyanthraquinone (3) and 1,2-dihydroxyanthraquinone (4) afforded 8-hydroxy-1-(4'-O-methyl-1beta-O-D-glucopyranosyloxy)anthraquinone (7) and 1-hydroxy-2-(4'-O-methyl-2beta-O-D-glucopyranosyloxy)anthraquinone (8), respectively, resulting from 4'-O-methyl-glucosylation of the existing hydroxyl groups of the substrates. The efficiency of these conversions suggests that microbial biotransformation reactions offer an attractive alternative to chemical 4'-O-methyl-glucosylation of amino- and hydroxyanthraquinones.

Glycosylation of (–)-maackiain byBeauveria bassianaandCunninghamella echinulatavar.elegans

“…B. bassiana and Cunninghamella spp. have been used for glycosylation of other phenolic natural products (Ibrahim et al 1997;Zhan & Gunatilaka 2006). Our results showed that B. bassiana and C. echinulata var.…”

Microbial Metabolism of Biologically Active Secondary Metabolites from Nerium oleander L.

“…These proton signals were easily linked to the new carbon signals at d 98. 4 38,39) and shown in Table 2. Further evidence came from the 3 3.44 3H, s CH 3 1.02 (d, 6) sylation was deduced from the H-1Љ/C-7 correlation observed in the HMBC spectrum.…”

Three Bianthraquinone Derivatives from the Mangrove Endophytic Fungus Alternaria sp. ZJ9-6B from the South China Sea

“…A wide variety of anthraquinone derivatives isolated from plants, animals and marine fungi have served as candidates for various therapeutic uses [1–3]. Anthraquinones inhibit the proliferation of human breast, colon and lung cancer cells [4].…”