Microbial biotransformation as a source of chemical diversity in cane toad steroid toxins

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 6, 2009, Pages 1790-1792

  Hayes, R Andrew ^a   Piggott, Andrew M ^a   Dalle, Kristian ^a   Capon, Robert J ^a  

^a UNIVERSITY OF QUEENSLAND   (Australia)

Author keywords

Biotransformation; Bufadienolide; Bufo marinus; Cane toad; Chemical ecology

Indexed keywords

BUFADIENOLIDE DERIVATIVE; MARINOBUFAGENIN;

ACINETOBACTER; ANIMAL TISSUE; ARTICLE; BACTERIUM CULTURE; BACTERIUM ISOLATE; BIOTRANSFORMATION; COMAMONAS TESTOSTERONI; CONTROLLED STUDY; FEMALE; FLAVOBACTERIA; GENETIC VARIABILITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NONHUMAN; PAROTID GLAND; TOAD;

1-BUTANOL; ANIMALS; BIOTRANSFORMATION; BUFANOLIDES; BUFO MARINUS; CHEMISTRY; CHROMATOGRAPHY; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ECOSYSTEM; EVOLUTION; MODELS, CHEMICAL; SPECIES SPECIFICITY; SPECTROPHOTOMETRY, ULTRAVIOLET; TIME FACTORS; TOXINS, BIOLOGICAL;

BACTERIA (MICROORGANISMS); BUFO MARINUS;

EID: 61349116338     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.01.064     Document Type: Article

References (29)

1. Lever C. The Cane Toad: The History and Ecology of a Successful Colonist (2001), Westbury Academic and Scientific, York, UK
2. Chen K.K., and Kovarikova A. J. Pharm. Sci. 56 (1967) 1535
3. Letnic M., Webb J.K., and Shine R. Biol. Conserv. 141 (2008) 1773
4. Crossland M.R., and Alford R.A. Aust. J. Ecol. 23 (1998) 129
5. Burnett S. Pac. Conserv. Biol. 3 (1997) 65
6. Mungomery R. Cane Grow. Q. Bull. 3 (1935) 21
7. Molloy, K.; Henderson, W. Science of Cane Toad Invasion and Control: Proceedings of the IA CRC/CSIRO/QLD NRM&W Cane Toad Workshop, June 2006, Brisbane; Invasive Animals Cooperative Research Centre: Bruce, A.C.T., 2006.
8. Hayes R.A., Barrett A., Alewood P.A., Grigg G.C., and Capon R.J. In: Hurst J.L., Beynon R.J., Roberts S.C., and Wyatt T.D. (Eds). Chemical Signals in Vertebrates Vol. 11 (2008), Springer, New York 409-417
9. Steyn P.S., and van Heerden F.R. Nat. Prod. Rep. 15 (1998) 397
10. 2O over 15 min, then 100% MeCN for 5 min (constant 0.01% TFA).
11. Zhan J., Guo H., Ning L., Zhang Y., and Guo D. Planta Med. 72 (2006) 346
12. Zhan J., Liu W., Guo H., Zhang Y., and Guo D. Enz. Microb. Tech. 33 (2003) 29
13. Zhan J., Zhang Y., Liu W., Guo H., and Guo D. Biocatal. Biotransform. 21 (2003) 141
14. Ye M., Ning L., Zhan J., Guo H., and Guo D. J. Mol. Catal. B: Enzym. 22 (2003) 89
15. Isolation and cultivation of microorganisms. A mature female cane toad (B. marinus) was euthanised and dissected. Microbial cultures were obtained from the ovaries, tongue, stomach and parotoid gland secretion of the toad by rubbing the tissues directly onto agar plates containing the following medium: peptone (Sigma) 4 g/L, sodium chloride (Univar) 1.5 g/L and agar (Sigma) 18 g/L. The plates were incubated at 26.5 °C until bacterial growth was evident on all plates (48 h). Selected colonies from each plate (total of 22) were sub-cultured onto fresh agar plates and incubated at 26.5 °C for 48 h. A single colony from each isolate was then used to inoculate aliquots of nutrient broth (10 mL) of the following composition: D-glucose (Amresco) 10 g/L, yeast extract (BD BBL) 4 g/L, peptone (Sigma) 2 g/L, sodium chloride (Univar) 1.5 g/L. The inoculated broths were incubated at 26.5 °C with vigorous shaking (140 rpm) until visibly turbid (24 h). A solution of pure 1 (purified from cane toad parotoid secretion) in acetone (15 mg/mL; 30 μL) was added to each culture, and incubation was continued for a further 48 h at 26.5 °C with shaking. Cultures were extracted with ethyl acetate (3 × 3 mL) and the combined organic layers were dried under a stream of nitrogen at 40 °C, then under high vacuum. The extracts were dissolved in methanol to a concentration of 2 mg/mL, filtered through a 0.45 μm PTFE filter and analysed by HPLC-DAD. Extracts showing the biotransformation of 1 were further analysed by HPLC-DAD-MS.
16. Skowasch D., Möbus E., and Maser E. Biochem. Biophys. Res. Comm. 294 (2002) 560
17. Marcus P.I., and Talalay P. J. Biol. Chem. 218 (1956) 661
18. Talalay P., Dobson M.M., and Tapley D.F. Nature 170 (1952) 620
19. Li L., Li P., Ye M., Zhong L., and Guo D. Lett. Org. Chem. 1 (2004) 176
20. Shimada K., Miyashiro Y., and Nishio T. Biomed. Chromatog. 20 (2006) 1321
21. Kamano Y., Kotake A., Hashima H., Inoue M., Morita H., Takeya K., Itokawa H., Nandachi N., Segawa T., Yukita A., Saitou K., Katsuyama M., and Petit G. Bioorg. Med. Chem. 6 (1998) 1103
22. Ribar B., Argay G., Kalman A., Vladimirov S., and Zivanov-Stakic D. J. Chem. Res. Synop. (1983) 90
23. 2O/MeCN to 100% MeCN over 15 min then hold for 5 min.
24. Akimova O.A., Bagrov A.Y., Lopina O.D., Kamernitsky A.V., Tremblay J., Hamet P., and Orlov S.N. J. Biol. Chem. 280 (2005) 832
25. Kesarcodi-Watson A., Kaspar H., Lategan M.J., and Gibson L. Aquiculture 274 (2008) 1
26. Das S., Ward L.R., and Burke C. Appl. Microbiol. Biotechnol. 81 (2008) 419
27. Vanselow B.A., Krause D.O., and McSweeney C.S. Aust. J. Agric. Res. 56 (2005) 219
28. Ritchie K.B. Mar. Ecol. Prog. Ser. 322 (2006) 1
29. Kutter E. In: Goldman E., and Green L.H. (Eds). Practical Handbook of Microbiology (2009), CRC Press, Boca Raton 713-730