Planta Med 2012; 78 - PI44
DOI: 10.1055/s-0032-1320731

Termination of the structural confusion between Plipastatin A1 and Fengycin IX

M Honma 1, K Tanaka 1, K Konno 2, K Tsuge 3, T Okuno 4, M Hashimoto 1
  • 1Department of Agriculture and Bioscience, Hirosaki University, 3-Bunkyo-cho, Hirosaki, 036–8561, Japan
  • 2Institute of Natural Medicine, University of Toyama, 2630 Sugitani, Toyama 930–0194, Japan
  • 3Institute of advanced bioscience, Keio University, Nipponkoku 403–1, Daihouji, Tsuruoka, Yamagata, 997–0035, Japan
  • 4University of Akita Nursing and Welfare, 2–3-4 Shimizu, Odate, 017–0046, Japan

Plipastatin A1 and fengycin IX had been considered as diastereomers due to the permutation of the enantiomeric pair of Tyr in most papers. We succeeded in proving experimentally that these are identical compounds, although their 1H NMR spectral data were reported to be considerably different each other. The 1H NMR spectrum of a depsipeptide from Bacillus subtilis H336B initially showed nice accordance with that of fengycin. However, the spectrum changed to become quite similar to that of plipastatin, when the sample was converted into the potassium salt. Our structural investigations disclosed that the structures of these molecules should be settled into that of plipastatin A1 by Umezawa (L-Tyr4 and D-Tyr10) in spite of more than 200 scientific papers about fengycins. These results consisted with the biogenesis of fengycin rather than old structure.