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Cytotoxic tetramic acid derivative produced by a plant type-III polyketide synthase


, : Cytotoxic tetramic acid derivative produced by a plant type-III polyketide synthase. Journal of the American Chemical Society 133(13): 4746-4749

The tetramic acid (2,4-pyrrolidinedione) scaffold has been recognized as an important structural feature because of its mycotoxic, antibacterial, antiviral, and antioxidant activities. This important class of natural products is reportedly produced by the type-I polyketide synthase/nonribosomal peptide synthetase (PKS/NRPS) hybrid megaenzyme systems. In contrast, the benzalacetone synthase (BAS) from Rheum palmatum is a structurally simple, plant-specific type-III PKS that catalyzes the one-step decarboxylative condensation of malonyl-CoA with 4-coumaroyl-CoA. The type-III PKS exhibits unusually broad substrate specificity and notable catalytic versatility. Here we report that R. palmatum BAS efficiently produces a series of unnatural, novel tetramic acid derivatives by the condensation of malonyl-CoA with aminoacyl-CoA thioesters chemically synthesized from L- and D-amino acids. Remarkably, the novel tetramic acid dimer D-5 formed from D-phenylalanoyl-CoA showed moderate antiproliferative activity against murine leukemia P388 cells.

US$19.90

PMID: 21391603

DOI: 10.1021/ja2006737


Other references

Sadé, J.; Halevy, A., 1974: The aetiology of bone destruction in chronic otitis media. Journal of Laryngology and Otology 88(2): 139-143

Coakley B.J.; Sinclair H.D.; Allen P.A.; Watts A.B., 1989: Stratigraphic simulation of a foreland basin; a diffusion model of the Molasse Basin, Central Alps. Eos, Transactions, American Geophysical Union 70(15): 464

Kryshtafovych, A.; Albrecht, R.; Baslé, A.; Bule, P.; Caputo, A.T.; Carvalho, A.Luisa.; Chao, K.L.; Diskin, R.; Fidelis, K.; Fontes, C.M.G.A.; Fredslund, F.; Gilbert, H.J.; Goulding, C.W.; Hartmann, M.D.; Hayes, C.S.; Herzberg, O.; Hill, J.C.; Joachimiak, A.; Kohring, G-Wieland.; Koning, R.I.; Lo Leggio, L.; Mangiagalli, M.; Michalska, K.; Moult, J.; Najmudin, S.; Nardini, M.; Nardone, V.; Ndeh, D.; Nguyen, T-Hong.; Pintacuda, G.; Postel, S.; van Raaij, M.J.; Roversi, P.; Shimon, A.; Singh, A.K, 2017: Target highlights from the first post-PSI CASP experiment (CASP12, May-August 2016). The functional and biological significance of the selected CASP12 targets are described by the authors of the structures. The crystallographers discuss the most interesting structural features of the target proteins and assess whether these featur...

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Satriotomo, I.; Miki, T.; Takeuchi, Y., 2001: Hypertestosterone and castration induce reactive astrocytes in suprachiasmatic nucleus of the male mice. The suprachiasmatic nucleus (SCN) has a long been recognized as the primary entraining influence upon circadian rhythms of behavior and physiological processes. The role of the SCN in circadian rhythms has been the subject of the wide variety of f...

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Raffa, I.; Galli, M.; Martínez Boero, M.; Bumaschny, E.; Roca, E., 2014: Multicenter registry of diagnosis, staging and treatment of rectal cancer in Buenos Aires City. Diagnosis and treatment of patients with rectal cancer has changed dramatically in recent decades. In order to assess the approach in this regard in Argentina we conducted a multicenter retrospective study in 18 health care services in Buenos Aire...

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