Summary
Reevaluation of the previously proposed structure of helminthosporoside, a host-specific toxin fromHelminthosporium sacchari, reveals a sesquiterpenoid bis-digalactoside. The carbohydrate portion of the toxin was characterized by13C-NMR spectroscopy, methylation analyses, FD and FAB mass spectroscopy. The ring size and anomeric configuration of the galactose moieties were determined by utilizing a13C-NMR structural analysis method. A new partial structure is proposed.
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Literatur
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A typical curve for this separation is found in the Ph.D. Thesis of R. C. Beier, Montana State University, Bozeman 1980.
The details concerning building, operating, and separation capabilities of this column are found in reference 5.
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A previous structure revision has been published11. Although our data do not result in the same conclusions reached by Livingston et al., the importance of understanding the correct structure of this toxin prompts us to report these results. A 2nd effort towards structure determination has been reported12, and again some differences in proposed structures are found.
Livingston, R.S., and Scheffer, R.P., J. biol. Chem.256 (1981) 1705.
Macko, V., Goodfriend, K., Wachs, T., Renwick, J.A.A., Acklin, W., and Arigoni, D., Experientia37 (1981) 923. We thank the authors for providing us with a preprint of their work.
Note added in proof: This residue correlates to an aglycone of formula C15H24O2. In a recent abstract (Macko, V., Acklin, W., and Agrigoni, D., 183rd American Chemical Society National Meeting, Las Vegas, Nevada, 1982, abstract 252) the structures of 3 isomeric aglycones were reported. We thank Prof. Arigoni for bringing this work to our attention. Prof. Arigoni has also suggested that our toxin, although we thought it to be homogenous, may have also contained the 3 isomers.
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Acknowledgment. We extend special thanks to C.E. Costello, Department of Chemistry, M.I.T., Cambridge, MA, for FD mass spectral analyses, and to C.E. Ballou, Department of Biochemistry, University of California, Berkeley, CA, for FAB mass spectral analyses. We submit sincere appreciation to both V.N. Reihold, Harvard Medical School, Boston, MA, and P. Albersheim, Department of Chemistry, University of Colorado, Boulder, CO, for methylation analyses. We thank J.S. Frye at the Colorado State University Regional NMR-Center, funded by National Science Foundation grant No. DHE 78-18581, Department of Chemistry, Colorado State University, Fort Collins, Co, for high resolution CMR and NMR, and we are grateful to P.W. Jennings, Department of Chemistry, Montana State University, Bozeman, Mt, for total carbon analyses. This work was supported in part by a Herman Frasch Foundation grant to G.A. Strobel, by NSF grant PCM-78-22517, and funds from the Montana Agricultural Experiment Station. B.P. Mundy acknowledges the partial support of NSF (ISP-801149).
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Beier, R.C., Mundy, B.P. & Strobel, G.A. Helminthosporoside, a host-specific toxin fromHelminthosporium sacchari: A structure revision and a new partial structure. Experientia 38, 1312–1314 (1982). https://doi.org/10.1007/BF01954921
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DOI: https://doi.org/10.1007/BF01954921