Summary
Fijiensin, a novel phytotoxic metabolite, was isolated from a culture of the fungusMycosphaerella fijiensis, the causal agent of Black Sigatoka disease of banana. Fijiensin is phytotoxic on various banana cultivars, but not toward non-host plants. The structure of fijiensin was determined by X-ray analysis.
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References
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Fijiensin, red needles, m.p. 207–8°.[α]D-95° (CHCl3, c=0.001). IR ν (CHCl3) 2980, 1760, 1660, 1650, 1610 cm−1. UV λmax nm (ɛ) 222 (3416), 258 (16 312), 273 (13 700), 284 (11 200), 295 (6950).1H NMR (400 MHz, CDCl3) δ 7.41 (1H s), 6.96 (1H d, J=1.9 Hz), 6.66 (1H d, J=1.9 Hz), 6.59 (1H dq, J=15.7, 6.8 Hz), 6.44 (1H s), 6.14 (1H s), 6.07 (1H dq, J=15.6, 1.6 Hz), 3.89 (3H s), 3.78 (3H s), 1.90 (3H dd, J=6.8, 1.6).13C NMR (100 MHz, CDCl3)δ 177.3 s, 170.0 s, 163.0 s, 162.1 s, 154.9 s, 153.9d, 135.9 d, 129.3 s, 127.7 s, 123.4 s, 123.1 d, 112.9 d, 105.1 d, 98.9 d, 73.6 d, 56.0 q, 55.8 q, 18.6 q.HRMS (El)m/z 328.0936 daltons. LRMSm/z (rel.int.) 329 (17), 328 (100), 313 (14), 285 (40), 271 (23), 269 (42), 260 (41), 259 (22), 257 (10).
Archival crystallographic data have been deposited with the Cambridge Crystallographic Data Centre, University Chemical Laboratory, Lensfield Road, Cambridge CB2 1EW, UK. Give a complete literature citation when ordering.
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Upadhyay, R.K., Strobel, G.A., Coval, S.J. et al. Fijiensin, the first phytotoxin fromMycosphaerella fijiensis, the causative agent of Black Sigatoka disease. Experientia 46, 982–984 (1990). https://doi.org/10.1007/BF01939396
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DOI: https://doi.org/10.1007/BF01939396