Zhan Jixun, Gunatilaka A A Leslie
Southwest Center for Natural Products Research and Commercialization, Office of Arid Lands Studies, College of Agriculture and Life Sciences, The University of Arizona, Tucson, Arizona 85706-6800, USA.
J Nat Prod. 2006 Oct;69(10):1525-7. doi: 10.1021/np060339k.
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.
球孢白僵菌ATCC 7159对四种氨基和羟基蒽醌的微生物生物转化已得到研究。1,2-二氨基蒽醌（1）与球孢白僵菌ATCC 7159一起培养，通过一种前所未有的涉及胺N-糖基化的生物转化反应生成了1-氨基-2-（4'-O-甲基-2β-N-D-吡喃葡萄糖基氨基）蒽醌（5）。1-氨基蒽醌（2）的生物转化反应中，C-2位发生微生物羟基化，随后新引入的羟基进行4'-O-甲基葡萄糖基化，生成1-氨基-2-（4'-O-甲基-2β-O-D-吡喃葡萄糖基氧基）蒽醌（6）。1,8-二羟基蒽醌（3）和1,2-二羟基蒽醌（4）分别通过底物现有羟基的4'-O-甲基葡萄糖基化反应，生成8-羟基-1-（4'-O-甲基-1β-O-D-吡喃葡萄糖基氧基）蒽醌（7）和1-羟基-2-（4'-O-甲基-2β-O-D-吡喃葡萄糖基氧基）蒽醌（8）。这些转化反应的效率表明，微生物生物转化反应为氨基和羟基蒽醌的化学4'-O-甲基葡萄糖基化提供了一种有吸引力的替代方法。
