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Microbial transformation of amino- and hydroxyanthraquinones by Beauveria bassiana ATCC 7159.
J Nat Prod. 2006 Oct; 69(10):1525-7.JN

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.

Authors+Show Affiliations

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.No affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

17067178

Citation

Zhan, Jixun, and A A Leslie Gunatilaka. "Microbial Transformation of Amino- and Hydroxyanthraquinones By Beauveria Bassiana ATCC 7159." Journal of Natural Products, vol. 69, no. 10, 2006, pp. 1525-7.
Zhan J, Gunatilaka AA. Microbial transformation of amino- and hydroxyanthraquinones by Beauveria bassiana ATCC 7159. J Nat Prod. 2006;69(10):1525-7.
Zhan, J., & Gunatilaka, A. A. (2006). Microbial transformation of amino- and hydroxyanthraquinones by Beauveria bassiana ATCC 7159. Journal of Natural Products, 69(10), 1525-7.
Zhan J, Gunatilaka AA. Microbial Transformation of Amino- and Hydroxyanthraquinones By Beauveria Bassiana ATCC 7159. J Nat Prod. 2006;69(10):1525-7. PubMed PMID: 17067178.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Microbial transformation of amino- and hydroxyanthraquinones by Beauveria bassiana ATCC 7159. AU - Zhan,Jixun, AU - Gunatilaka,A A Leslie, PY - 2006/10/28/pubmed PY - 2006/12/15/medline PY - 2006/10/28/entrez SP - 1525 EP - 7 JF - Journal of natural products JO - J. Nat. Prod. VL - 69 IS - 10 N2 - 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. SN - 0163-3864 UR - https://www.unboundmedicine.com/medline/citation/17067178/Microbial_transformation_of_amino__and_hydroxyanthraquinones_by_Beauveria_bassiana_ATCC_7159_ L2 - https://dx.doi.org/10.1021/np060339k DB - PRIME DP - Unbound Medicine ER -