Induced production of mycotoxins in an endophytic fungus from the medicinal plant Datura stramonium L.

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 20, 2012, Pages 6397-6400

  Sun, Jieyin ^a,b   Awakawa, Takayoshi ^a   Noguchi, Hiroshi ^b   Abe, Ikuro ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b UNIVERSITY OF SHIZUOKA   (Japan)

Author keywords

Datura stramonium L.; DNA methyltransferase inhibitor; Endophytic fungi; Epigenetic modifier; Histone deacetylase inhibitor

Indexed keywords

3' HYDROXYALTERNARIOL 5 O METHYL ETHER; ALTENUSIN; ALTERNARIOL; ALTERNARIOL 5 O METHYL ETHER; ALTERTOXIN II; AZACITIDINE; HYOSCYAMINE; MYCOTOXIN; SCOPOLAMINE; TENUAZONIC ACID; TROPANE ALKALOID; UNCLASSIFIED DRUG; VORINOSTAT;

ALTERNARIA; ARTICLE; CONTROLLED STUDY; DATURA STRAMONIUM; DNA MODIFICATION; ENDOPHYTE; EPIGENETICS; FUNGUS ISOLATION; NONHUMAN; TOXIN SYNTHESIS;

ALTERNARIA; AZACITIDINE; CULTURE MEDIA; DATURA STRAMONIUM; DNA MODIFICATION METHYLASES; ENZYME INHIBITORS; FUNGAL PROTEINS; HISTONE DEACETYLASE INHIBITORS; HYDROXAMIC ACIDS; MYCOTOXINS; PLANTS, MEDICINAL;

ALTERNARIA; DATURA STRAMONIUM; FUNGI;

EID: 84866740302     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2012.08.063     Document Type: Article

References (30)

1. N.P. Keller, G. Turner, and J.W. Bennett Nat. Rev. Microbiol. 3 2005 937
2. K. Scherlach, and C. Hertweck Org. Biomol. Chem. 7 2009 1753
3. K.M. Fisch, A.F. Gillaspy, M. Gipson, J.C. Henrikson, A.R. Hoover, L. Jackson, F.Z. Najar, H. Wägele, and R.H. Cichewicz J. Ind. Microbiol. Biotechnol. 36 2009 1199
4. E.K. Shwab, J.W. Bok, M. Tribus, J. Galehr, S. Graessle, and N.P. Keller Eukaryot. Cell. 6 2007 1656
5. R.N. Kharwar, A. Mishra, S.K. Gond, A. Stierle, and D. Stierle Nat. Prod. Rep. 28 2011 1208
6. A. Stierle, G. Strobel, and D. Stierle Science 260 1993 214
7. S.C. Puri, V. Verma, T. Amna, G.N. Qazi, and M. Spiteller J. Nat. Prod. 68 2005 1717
8. H.P. Rang, M.M. Dale, and J.M. Ritter Pharmacology 4th ed. 1999 Churchill Livingstone Edinburgh Elsevier p 139
9. D. stramonium L. plants were harvested from the medicinal plant garden at the University of Shizuoka in July 2011. All of the D. stramonium L. samples were washed in running tap water, and then separated into roots, stems and shells with scissors. Each sample was sterilized by immersion in 70% ethanol for 2 min, dried on sterile cotton cloth for 3 min, cut into small sections, and transferred to Petri dishes containing potato dextrose (PD) agar, amended with 60 μg/ml streptomycin and 100 μg/ml ampicillin. Petri dishes streaked by the surface of the samples were used as a negative control. All Petri dishes were incubated at 28 °C for 10 days. Individual hyphal tips of the various fungi were removed from the agar plates, placed on new PD agar medium, and incubated at 28 °C for 10 days. As a result, we obtained 5 strains from the root (R1-5), 3 strains from the shell (K1-3), and 6 strains from the stem (S1-6).
10. The S1 strain was identified by a DNA fragment within the fungal ribosomal DNA (rDNA) internal transcribed spacer (ITS) region (White, T. J.; Bruns, T.; Lee, S.; Taylor, J. In: Innis, M. A.; Gelfand, D. H.; Sninsky, J. J.; White, T. J. (Eds.); PCR Protocols; A guide to Methods and Applications. Academic Press: San Diego, 1990; pp 315-322). The genomic DNA of S1 was extracted. PCR was performed with the primers ITS1 (5′- TCCGTAGGTGAACCTGCGG-3′) and ITS4 (5′-TCCTCCGCTTATTGATATGC-3′), with DNA isolated from S1 by extraction with phenol/chloroform/isoamyl alcohol = 25:24:1, using PrimeStar HS DNA polymerase (Takara) and the following step program: 96 °C, 2 min; (96 °C, 15 s; 50 °C, 15 s; 72 °C, 30 s) × 35 cycles; 72 °C, 10 min. The amplified fragment was sequenced with an Applied Biosystems 3130XL sequencer. The sequence of the rDNA ITS region of the strain S1 showed 100% identity with that of the Alternaria sp. I426 strain, isolated from grapevine.
11. The mycelia of S1 were grown on PD agar medium at 30 °C for 7 days and then were inoculated into 75 mL of liquid PD medium, containing 250 μM 5-AC and/or 500 μM SBHA, in 500 mL flasks incubated at 28 °C under static conditions for 7 days. Broth culture filtrates were collected and extracted with n-BuOH. The organic layer was concentrated and subjected to HPLC analysis. The extracts were analyzed by HPLC equipped with a Tsk gel ODS-80TsQA column (TOSO), using a solvent system of 0.1% TFA (solvent A) and acetonitrile containing 0.1% TFA (solvent B), at a flow rate of 0.8 ml/min and a column temperature of 40 °C. Separation was performed with a linear gradient from solvent B/solvent A of 10:90 to 100:0 for 30 min, 100:0 for an additional 20 min and a linear gradient from 100:0 to 10:90 for 2 min.
12. T. Asai, Y.M. Chung, H. Sakurai, T. Ozeki, F.R. Chang, K. Yamashita, and Y. Oshima Org. Lett. 14 2012 513
13. Y. Wang, Q.G. Zeng, Z.B. Zhang, R.M. Yan, L.Y. Wang, and D. Zhu Ind. Microbiol. Biotechnol. 38 2011 1267
14. 3/MeOH solvent gradient. Fractions were further purified by preparative HPLC equipped with COSMOSIL cholester column (Nacalai Tesque), with a solvent system of 0.1% TFA (solvent A) and acetonitrile containing 0.1% TFA (solvent B), at a flow rate of 2.5 ml/min and a column temperature of 40 °C. The separation performance was equivalent to that of the analytical method. The yields of each compounds were as follows: 1 (1.5 mg), 2 (2.0 mg), 3 (1.3 mg), 4 (1.4 mg), 5 (20.0 mg), and 6 (2.2 mg).
15. - 257.0445; Calcd 257.0445.
16. E.E. Stinson, W.B. Wise, R.A. Moreau, A.J. Jurewicz, and P.E. Pfeffer Can. J. Chem. 64 1986 1590
17. - 271.0617; Calcd 271.0601.
18. - 287.0575; Calcd 287.0550.
19. - 289.0706; Calcd 289.0706.
20. P.A. Onocha, D.A. Okorie, J.D. Connolly, and D.S. Roycroft Phytochemistry 40 1995 1183
21. A.H. Aly, R. Edrada-Ebel, I.D. Indriani, V. Wray, W.E. Müller, F. Totzke, U. Zirrgiebel, C. Schächtele, M.H. Kubbutat, W.H. Lin, P. Proksch, and R. Ebel J. Nat. Prod. 71 2008 972
22. S. Nakanishi, S. Toki, Y. Saitoh, E. Tsukuda, K. Kawahara, K. Ando, and Y. Matsuda Biosci. Biotechnol. Biochem. 59 1995 1333
23. E.K. Bomati, M.B. Austin, M.E. Bowman, R.A. Dixon, and J.P. Noel J. Biol. Chem. 280 2005 30496
24. - 196.0967; Calcd 196.0968.
25. M. Nolte, P.S. Steyn, and P.L. Wessels J. Chem. Soc., Perkin Trans. 1 1980 1057
26. M.H. Lebrun, L. Nicolas, M. Boutar, F. Gaudemer, S. Ranomenjanahary, and A. Gaudemer Pytochemistry 27 1988 77
27. - 349.0723; Calcd 349.0707.
28. M.E. Stack, E.P. Mazzola, S.W. Page, and A.E. Pohland J. Nat. Prod. 49 1986 866
29. T. Okuno, I. Natsume, K. Sawai, K. Sawamura, A. Furusaki, and T. Matsumoto Tetrahedron Lett. 24 1983 5653
30. R.W. Pero, H. Posner, M. Blois, D. Harvan, and J.W. Spalding Environ. Health Perspect. Experimental issue 4 1973 87