Enzymatic and Microbial Biosynthesis of Novel Violacein Glycosides with Enhanced Water Solubility and Improved Anti-nematode Activity
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Violacein, a microbial metabolite with multiple applications, was produced in Escherichia coli, and glycodiversified using purified Bacillus glycosyltransferase (YjiC) enzyme with glucose, galactose, and N-acetylglucosamine, to generate five novel O-glycoside derivatives. One of the glucose-conjugated derivatives, violacein 5′-O-glucoside, was produced from engineered E. coli harboring entire violacein biosynthetic gene cluster (VioABCDE) and a glycosyltransferase gene (yjiC) in tryptophan supplemented TB medium. Violacein 5′-O-glucoside gained anti-nematodal activity against pine wood nematode Bursaphelenchus xylophilus, a causative agent of pine wilt disease. Moreover, the conjugation of sugar moieties in violacein enhanced water solubility. Violacein 5′-O-diglucoside was completely retained in water fraction, while its aglycone parent molecule was completely insoluble in water.
Keywordsviolacein glycodiversification anti-nematode novel glycosides
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This work was supported by a grant from the Next-Generation BioGreen 21 Program (SSAC, grant#: PJ013137), Rural Development Administration, Republic of Korea.
- 1.Tobie, W. C. (1934) The pigment of Bacillus violaceus I. The production, extraction, and purification of violacein. J. Bacteriol. 29: 223–227.Google Scholar
- 4.Tan, T. L., F. P. Montforts, and D. Meyer (2002) Microbiological method for the biosynthesis of natural blue-violet colorants violacein and desoxyviolacein. PCT Int. Appl. WO 2002050299 A2Google Scholar
- 6.Shirata, A., T. Tsukamoto, H. Yasui, T. Hata, S. Hayasaka, A. Kojima, and H. Kato (2000) Isolation of bacteria producing bluish-purple pigment and use for dyeing. Japan Agric. Res. Quart. 34: 131–140.Google Scholar
- 9.Fang, M. Y., C. Zhang, S. Yang, J. Y. Cui, P. X. Jiang, K. Lou, M. Wachi, and X. H. Xing (2015) High crude violacein production from glucose by Escherichia coli engineered with interactive control of tryptophan pathway and violacein biosynthetic pathway. Microb. Cell Fact. 14: 8.CrossRefGoogle Scholar
- 12.Shirata, A., T. Tsukamoto, H. Yasui, H. Kato, S. Hayasaka, and A. Kojima (1997) Production of bluish-purple pigments by Janthinobacterium lividum isolated from the raw silk and dyeing with them. Nippon Sanshigaku Zasshi 66: 377–385.Google Scholar
- 16.Costa, F. T. M., G. Z. Justo, N. Durán, P. A. Nogueira, and S. C. P. Lopes (2005) The use of violacein in its free and encapsulated form in polymeric systems against malaria. Brazilian Patent PIBr 056399-0.Google Scholar
- 17.Lopes, S. C. P., Y. C. Blanco, G. Z. Justo, P. A. Nogueira, F. L. S. Rodrigues, U. Goelnitz, G. Wunderlich, G. Facchini, M. Brocchi, N. Durán, and F. T. M. Costa (2009) Violacein extracted from Chromobacterium violaceum inhibits Plasmodium growth in vitro and in vivo. Antimocrob. Agents Chemother. 53: 2149–2152.CrossRefGoogle Scholar
- 23.Baek, S. H., H. S. Kang, I. H. Jang, J. S. Lee, S. Y. Kim, J. H. Baek, J. G. Kang, and J. M. Ahn (2007) Insecticide and fungicide containing violacein, and their preparation method. Repub. Korean Kongkae Taeho Kongbo KR 2007088150 AGoogle Scholar
- 28.Hoshino, T. and N. Ogasawara (1990) Biosynthesis of violacein: evidence for the intermediacy of 5-hydroxy-l-tryptophan and the structure of a new pigment, oxyviolacein, produced by the metabolism of 5-hydroxytryptophan. Agric. Bioi. Chern. 54: 2339–2346.Google Scholar
- 30.Toth, A. (2011) Bursaphelenchus xylophilus, the pinewood nematode: its significance and a historical review. Acta Biol. Szeged. 55: 213–217.Google Scholar