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Molecules 2018, 23(9), 2171; https://doi.org/10.3390/molecules23092171

Microbial Synthesis of Non-Natural Anthraquinone Glucosides Displaying Superior Antiproliferative Properties

1
Department of Life Science and Biochemical Engineering, Sun Moon University, 70 Sunmoon-ro 221, Tangjeong-myeon, Asan-si, Chungnam 31460, Korea
2
Department of BT-Convergent Pharmaceutical Engineering, Sun Moon University, 70 Sunmoon-ro 221, Tangjeong-myeon, Asan-si, Chungnam 31460, Korea
3
Department of Biotechnology, The Catholic University of Korea, Bucheon, Gyeonggi-do 14662, Korea
These authors contributed equally to this work.
*
Author to whom correspondence should be addressed.
Received: 17 July 2018 / Revised: 14 August 2018 / Accepted: 21 August 2018 / Published: 28 August 2018
(This article belongs to the Special Issue Antitumoral Properties of Natural Products)
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Abstract

Anthraquinones, naturally occurring bioactive compounds, have been reported to exhibit various biological activities, including anti-inflammatory, antiviral, antimicrobial, and anticancer effects. In this study, we biotransformed three selected anthraquinones into their novel O-glucoside derivatives, expressing a versatile glycosyltransferase (YjiC) from Bacillus licheniformis DSM 13 in Escherichia coli. Anthraflavic acid, alizarin, and 2-amino-3-hydroxyanthraquinone were exogenously fed to recombinant E. coli as substrate for biotransformation. The products anthraflavic acid-O-glucoside, alizarin 2-O-β-d-glucoside, and 2-amino-3-O-glucosyl anthraquinone produced in the culture broths were characterized by various chromatographic and spectroscopic analyses. The comparative anti-proliferative assay against various cancer cells (gastric cancer-AGS, uterine cervical cancer-HeLa, and liver cancer-HepG2) were remarkable, since the synthesized glucoside compounds showed more than 60% of cell growth inhibition at concentrations ranging from ~50 μM to 100 μM. Importantly, one of the synthesized glucoside derivatives, alizarin 2-O-glucoside inhibited more than 90% of cell growth in all the cancer cell lines tested. View Full-Text
Keywords: anti-cancer agents; anthraquinones; glycosyltransferase anti-cancer agents; anthraquinones; glycosyltransferase
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Nguyen, T.T.H.; Pandey, R.P.; Parajuli, P.; Han, J.M.; Jung, H.J.; Park, Y.I.; Sohng, J.K. Microbial Synthesis of Non-Natural Anthraquinone Glucosides Displaying Superior Antiproliferative Properties. Molecules 2018, 23, 2171.

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