• The Plant Pathology Journal
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• v.15 no.1
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• pp.14-20
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• 1999

Twenty isolates of Helminthosporium species were obtained from various grass plants and tested for controlling efficacy on the development of plant diseases. An isolate of Helminthosporium sp. TP-4 was chosen and six antibiotic substances were purified from cultures of the fungus by repeated silica gel column chromatography and preparative thin-layer chromatography. They were identified as ophiobolin a, 6-epiophiobolin A, 3-anhydroophiobolin A, 3-anhydro-6-epiophiobolin A, iphiobolin B, and iphiobolin I mainly by mass spectrometry and nuclear magnetic resonance spectrometry. Ophiobolins inhibited the growth of a grampositive bacterium Streptomyces griseus, but were not active against gram-negative bacteria. They also showed an antifungal activity. In in vivo tests, iphiobolin B exhibited potent controlling activities against rice blast, tomato late blight, and wheat leaf rust with control values more than 90% and 70% at concentration of $500\mu\textrm{m}$/ml and 100 ${\mu}{\textrm}{m}$/ml. Ophiobolin A and 6-epiophiobolin A controlled the development of wheat leaf rust more than 80% at concentrations of 100 /ml and $500\mu\textrm{m}$/ml respectively. 3-Anhydro-6-epiophiobolin A was not active against any plant disease. On the other hand, the A-series ophiobolins other than 3-anhydroophiobolin A showed stronger phytotoxic activity in a leaf-wounding assay using 8 plant species than those of 3-anhydroophiobolin A, ophiobolin B, and ophiobolin I. The results indicate that there is little correlation between antifungal activity and phytotoxicity of ophiobolins.

• Journal of Microbiology and Biotechnology
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• v.8 no.4
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• pp.406-408
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• 1998

6-Epiophiobolin A, 3-anhydro-6-epiophiobolin A, and ophiobolin I were isolated from culture broth of Bipolaris sp. as cytotoxic agents against human tumor cells. Both 6-epiophiobolin A and 3-anhydro derivatives demonstrated significant cytotoxicity, having $IC_{50}$ values in the range of $1{\mu}g$/ml, which indicates that they have comparable cytotoxic potential with that of etoposide. The activity of ophiobolin I was, however, very weak compared with those of 6-epiophiobolin A and etoposide.