Enzymatic and Microbial Biosynthesis of Novel Violacein Glycosides with Enhanced Water Solubility and Improved Anti-nematode Activity

다국어 초록 (Multilingual Abstract)

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′-Oglucoside, 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.

참고문헌 (Reference)

1 Costa, F. T. M, "use of violacein in its free and encapsulated form in polymeric systems against malaria"

2 Jones, J. A, "ePathOptimize : A combinatorial approach for transcriptional balancing of metabolic pathways" 5 : 11301-, 2015

3 Lopes, S. C. P, "Violacein extracted from Chromobacterium violaceum inhibits Plasmodium growth in vitro and in vivo" 53 : 2149-2152, 2009

4 Melo, P. S, "Violacein cytotoxicity and induction of apoptosis in V79cells" 36 : 539-543, 2000

5 Melo, P. S, "Violacein and its beta-cyclodextrin complexes induce apoptosis and differentiation in HL60 cells" 186 : 217-225, 2003

6 Durán, N, "Violacein : properties and biological activities" 48 : 127-133, 2007

7 Weymouth-Wilson, A. C, "The role of carbohydrates in biologically active natural products" 14 : 99-110, 1997

8 Tobie, W. C, "The pigment of Bacillus violaceus I, The production, extraction" 29 : 223-227, 1934

9 Parajuli, P, "Synthetic sugar cassettes for the efficient production of flavonol glycosides in Escherichia coli" 14 : 76-, 2015

10 Ahmetagic, A, "Stable high level expression of the violacein indolocarbazole anti-tumour gene cluster and the Streptomyces lividans amyA gene in E" 63 : 79-85, 2010

11 Laatsch, H, "Spectroscopic properties of violacein and related compound: crystal structure of tetramethylviolacein" 8 : 1331-1339, 1984

12 Takii, T, "Simple fibroblast-based assay to test the pyrazinamide susceptibility of Mycobacterium tuberculosis" 49 : 804-807, 2005

13 Yoshitoshi Nakamura, "Production of Antibacterial Violet Pigment by Psychrotropic Bacterium RT102 Strain" 한국생물공학회 8 (8): 37-40, 2003

14 Pandey, R.P, "Production of 3-O-xylosyl quercetin in Escherichia coli" 97 : 1889-1901, 2013

15 Durán, M, "Potential applications of violacein : a microbial pigment" 21 : 1524-1532, 2012

16 Futai, K, "Pine wood nematode, Bursaphelenchus xylophilus" 51 : 61-83, 2013

17 Mota, M. M, "Pine Wilt Disease: A Worldwide Threat to Forest Ecosystems" Springer Verlag GmbH 2008

18 Tan, T. L, "Microbiological method for the biosynthesis of natural blue-violet colorants violacein and desoxyviolacein" 2002

19 Shirata, A, "Kojima(1997)Production of bluish-purple pigments by Janthinobacterium lividum isolated from the raw silk and dyeing with them" 66 : 377-385, 1997

20 Shirata, A, "Isolation of bacteria producing bluish-purple pigment and use for dyeing" 34 : 131-140, 2000

21 Baek, S. H, "Insecticide and fungicide containing violacein, and their preparation method. Repub"

22 Balibar, C. J, "In vitro biosynthesis of violacein from L-tryptophan by the enzymes VioA-E from Chromobacterium violaceum" 45 : 15444-15457, 2006

23 Matz, C, "Impact of violacein-producing bacteria on survival and feeding of bacterivorous nanoflagellates" 70 : 1593-1599, 2004

24 Antonisamy, P, "Immunomodulatory, analgesic and antipyretic effects of violacein isolated from Chromobacterium violaceum" 17 : 300-304, 2010

25 Choi, S. Y, "High-level production of violacein by the newly isolated Duganella violaceinigra str, NI28 and its impact on Staphylococcus aureus" 5 : 15598-, 2015

26 Fang, M. Y, "High crude violacein production from glucose by Escherichia coli engineered with interactive control of tryptophan pathway and violacein biosynthetic pathway" 14 : 8-, 2015

27 Bromberg, N, "Growth inhibition and proapoptotic activity of violacein in Ehrlich ascites tumor" 186 : 43-52, 2010

28 Huang, G, "Glycosylation and activities of natural products" 16 : 1013-1016, 2016

29 Choi, H. Y, "Enzymatic synthesis of avermectin B1a glycosides for the effective prevention of the pine wood nematode Bursaphelenchus xylophilus" 102 : 2155-2165, 2018

30 Andrighetti-Frohner, C. R, "Cytotoxicity and potential antiviral evaluation of violacein produced by Chromobacterium violaceum" 98 : 834-848, 2003

31 Durán, N, "Chromobacterium violaceum : A review of pharmacological and industrial perspectives" 27 : 201-222, 2001

32 Toth, A, "Bursaphelenchus xylophilus, the pinewood nematode : its significance and a historical review" 55 : 213-217, 2011

33 Hoshino, T, "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" 54 : 2339-2346, 1990

34 Antonisamy, P, "Antidiarrhoeal and ulcer-protective effects of violacein isolated from Chromobacterium violaceum in Wistar rats" 23 : 483-490, 2009

35 Elshahawi, S. I, "A comprehensive review of glycosylated bacterial natural products" 44 : 7591-7697, 2015