Tryprostatin A, B, Demethoxyfumitremorgin C, Spirotryptostatin B
| Tryprostatin A: |  |
| Tryprostatin B: | |
| Demethoxyfumitremorgin C: | |
| Spirotryprostatin B: | |
- Producing organism
- Aspergillus fumigatus
- Biological activity
- mitotic inhibition, tubulin assemble inhibition
- Abstract
- Two novel diketopiperazines named tryprostatins A (1) and B (2) and a new natural product belonging to the diketopiperazine series, designated as demethoxyfumitremorgin C (3), together with four known diketopiperazines, fumitremorgin C (4), 12,13-dihydroxyfumitremorgin C (5), fumitremorgin B (6) and verruculogen (7), were isolated from the fermentation broth of Aspergillus fumigatus BM939 by the combined use of solvent extraction, silica gel column chromatography, preparative TLC and repeated-preparative HPLC. The diketopiperazines showed an inhibitory activity on the cell cycle progression of mouse tsFT210 cells in the M phase with the MIC values of 16.4 µM (1), 4.4 µM (2), 0.45 µM (3), 4.1 µM (4), 60.8 µM (5), 26.1 µM (6) and 12.2 µM (7), respectively.
- References
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isolation and structural determination
- Cui CB, Kakeya H, Okada G, Onose R, Ubukata M, Takahashi I, Isono K, Osada H.: Tryprostatins A and B, novel mammalian cell cycle inhibitors produced by Aspergillus fumigatus.
J Antibiot, 48(11): 1382-1384 (1995)
- Cui CB, Kakeya H, Okada G, Onose R, Osada H.: Novel mammalian cell cycle inhibitors, tryprostatins A, B and other diketopiperazines produced by Aspergillus fumigatus. I. Taxonomy, fermentation, isolation and biological properties.
J Antibiot, 49(6): 527-533 (1996)- Cui CB, Kakeya H, Osada H.: Novel mammalian cell cycle inhibitors, tryprostatins A, B and other diketopiperazines produced by Aspergillus fumigatus. II. Physico-chemical properties and structures.
J Antibiot, 49(6): 534-540 (1996)- Cui CB, Kakeya H, Osada H.: Spirotryprostatin B, a novel mammalian cell cycle inhibitor produced by Aspergillus fumigatus.
J Antibiot, 49(8): 832-835 (1996)detailed biological activity- Usui T, Kondoh M, Cui CB, Mayumi T, Osada H.: Tryprostatin A, a specific and novel inhibitor of microtubule assembly.
Biochem J, 333( Pt 3): 543-548 (1998)- Kondoh M, Usui T, Mayumi T, Osada H.: Effects of tryprostatin derivatives on microtubule assembly in vitro and in situ.
J Antibiot, 51(8): 801-804 (1998)structure-activity relationship- Wang H, Usui T, Osada H, Ganesan A.: Synthesis and evaluation of tryprostatin B and demethoxyfumitremorgin C analogues.
J Med Chem, 43(8): 1577-1585 (2000)- Sanz-Cervera JF, Stocking EM, Usui T, Osada H, Williams RM.: Synthesis and evaluation of microtubule assembly inhibition and cytotoxicity of prenylated derivatives of cyclo-L-Trp-L-Pro.
Bioorg Med Chem, 8(10): 2407-2415 (2000) - Cui CB, Kakeya H, Okada G, Onose R, Ubukata M, Takahashi I, Isono K, Osada H.: Tryprostatins A and B, novel mammalian cell cycle inhibitors produced by Aspergillus fumigatus.