Fischerellin A, a novel photosystem-II-inhibiting allelochemical of the cyanobacterium Fischerella muscicola with antifungal and herbicidal activity

Tetrahedron Letters

Volumn 37, Issue 36, 1996, Pages 6539-6542

  Hagmann, Leonhard ^a   Jüttner, Friedrich ^b  

^a SANDOZ AGRO Ltd   (Switzerland)

^b UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOTOXIC AGENT; FISCHERELLIN A; UNCLASSIFIED DRUG;

ALGA; ANTIFUNGAL ACTIVITY; ARTICLE; CYTOTOXICITY; DRUG ISOLATION; DRUG STRUCTURE; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; PHOTOSYSTEM II; ULTRAVIOLET SPECTROPHOTOMETRY;

ALGAE; CYANOBACTERIA; FISCHERELLA MUSCICOLA; SYNECHOCOCCUS;

EID: 0030565587     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01445-1     Document Type: Article

References (18)

1. Schopf, J.W. Proc.Natl.Acad.Sci. USA 1994, 91, 6735-6742.
2. Mason, C.P.; Edwards, K.R.; Carlson, R.E.; Pignatello, J.; Gleason, F.K.; Wood, J.M. Science (Wash.) 1982, 215, 400-402.
3. Moore, R.E.; Cheuk, C; Patterson, G.M.L. J.Am.Chem.Soc. 1984, 106, 6456-6457.
4. Gross, E.M.; Wolk, C.P.; Jüttner, F. J.Phycol. 1991, 27, 686-692.
5. The biomass was separated with a strainer. Its methanolic (60%, 280 mL) extract was partitioned between 100 mL TBME and 200 mL water.
6. 2O 45:45:10 and passed through the C-18 cartridge (Mega-BondElut, Varian), eluted with the same solvent mixture and collected before green compounds appeared.
7. OW = 3.6 at 25 °C.
8. Low resolution EI-MS were obtained on a GC-MS after separation on a 10 m capillary column (0.32 mm i.d., SIM-DIST-CB, Chrompack, helium carrier gas): m/z (rel. int. %) 408 (100), 365 (35), 351 (40), 337 (35), 242 (43), 207 (94), 176 (71), 148 (41), 94 (48). Thermospray MS were recorded on a Vestec mass spectrometer (1 ml/min., methanol/0.1 M aqueous ammonium acetate 1:1).
9. 15N-nitrate (4 mM). F. muscicola grown in this medium for 28 days was producing 29 g biomass. 27% of the Fischerellin molecules were single-labeled, 66% were double-labeled (shown by MS).
10. 13C-labeled Fischerellin A were obtained. The atom percentage labeling was 3.5 % (by MS).
11. Ahmed, M.; Barley, G.C.; Bentley, R.K.; Hearn, M.T.W.; Higham, C.A.; Jenkins, J.K.; Jones, Sir E.R.H.; Keeping, J.W.; Thaller, V.; Yates, J.A. J. Chem. Soc. Perkin I 1974, 1981-1994.
12. Wittstock, U.; Hadacek, F.; Wurz, G.; Teuscher, E.; Greger, H. Planta Med. 1995, 61, 439-445.
13. m/z 379, 365, 351, 337 and 29, 43, 57, respectively.
14. 13C-Shift-Estimation. In: SpecTool, a Hypermedia Book for Structure Elucidation of Organic Compounds with Spectroscopic Methods, Chemical Concepts, Weinheim, 1995.
15. H-C6 and H-C8 give strong ROESY correlations with one of the C7 methylene protons at 2.47 ppm, indicating that all these protons are on the same side of the five-membered ring, hence both ring substituents must be cis to each other.
16. Todorova, A.; Jüttner, F. Phycologia (in press).
17. Niderman, T.; Genetet, I.; Bruyère, T.; Gees, R.; Stintzi, A.; Legrand, M.; Fritig, B.; Mösinger, E. Plant Physiology 1995, 108, 17-27.
18. Schweizer, P.; Gees, R.; Mösinger, E. ibid. Plant Physiology 1993, 102, 503-511.