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Bionectriol A

Bionectriol A Jared
Julien Monot


Bionectriol A is a new polyketide glycoside produced by a fungal culture of Bionectria sp. which was isolated by Clardy and coworkers1 from a fungus garden of the fungus-growing ant Apterostigma dentigerum, in Costa Rica in 2009. They determined the structure of Bionectriol A, mainly, with NMR spectrometry and mass spectrometry.

Bionectriol A is structurally identical to Roselipins 3 isolated from Clonostachys candelabrum in 2010.2

Roselipins

Roselipins 3A-3E were obtained in mixtures (mixture 1: Roselipins 3A-B; mixture 2: Roselipins 3C-E) and the stereoconfiguration of the polyketide chain C1-C20 was not discussed in the paper. Nevertheless, the structure of Bionectriol A matches perfectly with Roselipins 3A. The only difference between the 5 roselepins 3A-3E is the position where the polyketide chain (C1-C20) was esterified to the arabinitol moiety residue (C1-C5).

The Roselipins family was known to be selective inhibitors of diacylglycerol transferase 23 and to show cytotoxicity against several tumor cell lines in particular, TMC-151F.4 Roselipins 2A and 2B have some HIV-1 integrase inhibition activity.5 These new Roselipins (3A-3E) are the first classes of Roselipins antibiotics to express an anthelmintic activity.

So far, Roselipins are produced by biosynthesis, and no total syntheses of this family of drugs have been described.

References:

1. Freinkman, E.; Oh, D.-C.; Scott, J. J.; Currie, C. R.; Clardy, J. Tetrahedron Lett. 2009, 50, 6834-6837.

2. Ayers, S.; Zink, D. L.; Mohn, K.; Powell, J. S.; Brown, C. M.; Bills, G.; Grund, A.; Thompson, D., Singh, S. B. J. Antibiot. 2010, 63, 119-122.

3. (a) Omura, S.; Tomoda, H.; Tabata, N.; Ohyama, Y.; Abe, T.; Namikoshi, M. J. Antibiot. 1999, 52, 586-589. (b) Tabata, N.; Ohyama, Y.; Tomoda, H. ; Abe, T.; Namikoshi, M.; Omura, S. J. Antibiot. 1999, 52, 815-826. (c) Tomoda et al. J. Antibiot. 1999, 52, 689-694. (d) Inokoshi, J.; Kawamoto, K.; Takagi, Y.; Matsuhama, M.; Omura, S.; Tomoda, H. J. Antibiot. 2009, 62, 51-54.

4. (a) Kohno, J. et al. Tetrahedron 1999, 55, 7771-7786. (b) Kohno, J. et al. J. Antibiot. 1999, 52, 1114-1123.

5. Singh, S. B. et al. J. Ind. Microbiol. Biotechnol. 2003, 30, 721-731.