Enhancing the antimicrobial effect of genistein by biotransformation in microbial system

HaeRi Choi; Jin-Soo Park; Kyu-Min Kim; MinSun Kim; Kwang-Wook Ko; Chang-Gu Hyun; Joong Woo Ahn; Joo-Hyun Seo; Seung-Young Kim

Journal of Industrial and Engineering Chemistry, Vol.63, 255-261, July, 2018

DOI10.1016/j.jiec.2018.02.023 Export Citation

Enhancing the antimicrobial effect of genistein by biotransformation in microbial system

HaeRi Choi, Jin-Soo Park¹, Kyu-Min Kim, MinSun Kim, Kwang-Wook Ko², Chang-Gu Hyun³, Joong Woo Ahn⁴, Joo-Hyun Seo^†, and Seung-Young Kim^†

Institute of Biomolecule Reconstruction, Department of BT-Convergent Pharmaceutical Engineering, Sunmoon University, 70 Sunmoon-ro 221, Tangjeong-myeon, Asan-si, Chungnam 31460, Republic of Korea
¹Natural Constituents Research Center, Korea Institute of Science and Technology, Gangneung, Gangwon-do 25451, Republic of Korea
²DaeHo Corporation, 49-4, Oncheon-ro, Paltan-myun, Hwaseong-si, Gyeonggi-do 18577, Republic of Korea
³Cosmetic Science Center, Department of Chemistry and Cosmetics, Jeju National University, Jeju 63243, Republic of Korea
⁴Department of Interdisciplinary ECO Science, Sungshin University, Seoul 01133, Republic of Korea

E-mail:,

In this study, we report Bio-renovation, which is a method to biologically derivatize natural compounds to make drug candidate library. In this method, microorganisms produce various derivatives of natural compounds, thereby converting natural compounds into novel bioactive candidates. Five derivatives of genistein were synthesized by Bio-renovation using Bacillus amyloliquefaciens KCTC 13588. Among the genistein derivatives, 4'-O-isopropyl genistein showed antimicrobial activity against eight strains including methicillin resistant Staphylococcus aureus (MRSA) and methicillin-sensitive Staphylococcus aureus (MSSA) with MIC and MBC values of 8.128 mg/ml. We could find that 4'-O-isopropyl genistein has higher antimicrobial activity than genistein to gram-positive bacteria.

Keywords:Derivatization;Chemical library;Biotransformation;Genistein;Antimicrobial activity

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[2] Huang SS, Su SY, Chang JS, Lin HJ, Wu WT, Deng JS, Huang GJ, Bot. Stud., 57, 38 (2016)

[3] Leyva-Lopez N, Gutierrez-Grijalva EP, Ambriz-Perez DL, Heredia JB, Int. J. Mol. Sci., 17(6), 921 (2016)

[4] Barnes S, Lymphat. Res. Biol., 8(1), 89 (2010)

[5] Davis DD, Diaz-Cruz ES, Landini S, Kim YW, Brueggemeier R, J. Steroid Biochem. Mol. Biol., 108, 23 (2008)

[6] Ma DF, Qin LQ, Wang PY, Katoh R, Clin. Nutr., 27(1), 57 (2008)

[7] Clavel T, Fallani M, Lepage P, Levenez F, Mathey J, Rochet V, et al., J. Nutr., 135(12), 2786 (2005)

[8] Akiyama T, Ishida J, Nakagawa S, Ogawara H, Watanabe S, Itoh N, Shibuya M, Fukami Y, J. Biol. Chem., 262, 5592 (1987)

[9] Wei H, Bowen R, Cai Q, Barnes S, Wang Y, Proc. Soc. Exp. Biol. Med., 208, 124 (1995)

[10] Chebil L, Humeau C, Anthoni J, Dehez F, Engasser JM, Ghoul M, J. Chem. Eng. Data, 52(5), 1552 (2007)

[11] Haddad AQ, Venkateswaran V, Viswanathan L, Teahan SJ, Fleshner NE, Klotz LH, Prostate Cancer Prostatic Dis., 9, 68 (2006)

[12] Wang ST, Fang TF, Hsu C, Chen CH, Lin CJ, Su NW, J. Funct. Foods, 13, 323 (2015)

[13] Wang A, Zhang F, Huang L, Yin X, Li H, Wang Q, Zeng Z, Xie T, J. Med. Plants Res., 4, 847 (2010)

[14] Bartmanska A, Tronina T, Poplonski J, Huszcza E, Curr. Drug Metab., 14, 1083 (2013)

[15] Kim YS, Cho SH, Jeong DY, Uhm TB, Korean J. Microbiol., 48(3), 220 (2012)

[16] Erlacher A, Cardinale M, Grosch R, Grube M, Berg G, Front. Microbiol., 5, 117 (2014)

[17] Wiegand I, Hilpert K, Hancock R, Nat. Protoc., 3(2), 163 (2008)

[18] Mok JS, Song KC, Choi NJ, J. Aquac., 14(3), 157 (2001)

[19] Schrewe M, Julsing MK, Buhler B, Schmid A, Chem. Soc. Rev., 42(15), 6346 (2013)

[20] Kanakubo A, Koga K, Isobe M, Fushimi T, Saitoh T, Ohshima Y, Tsukamoto Y, Tetrahedron, 57(42), 8801 (2001)

[21] Durango D, Quinones W, Torres F, Rosero Y, Gil J, Echeverri F, Molecules, 7(11), 817 (2002)

[22] She GM, Sun FF, Wang S, Liu B, Chem. Nat. Compd., 49(5), 938 (2013)

[23] Toda T, Uesugi T, Hirai K, Nukaya H, Tsuji K, Ishida H, New Biol. Pharm. Bull., 22(11), 1193 (1999)

[24] Whitby M, McLaws ML, Berry G, Med. J. Aust., 175(5), 264 (2001)

[25] Sakagami Y, Iinuma M, Piyasena KG, Dharmaratne HR, Phytomedicine, 12(3), 230 (2005)

[26] Guo Z, Acta Pharm. Sin. B, 7(2), 119 (2017)

[27] Arunasri K, Adil M, Khan PAA, Shivaji S, PLoS One, 9(5), e96701 (2014)

[28] Thierbach S, Birmes FS, Letzel MC, Hennecke U, Fetzner S, ACS Chem. Biol., 12(9), 2305 (2017)