Structures of Nahuoic Acids B–E Produced in Culture by a Streptomyces sp. Isolated from a Marine Sediment and Evidence for the Inhibition of the Histone Methyl Transferase SETD8 in Human Cancer Cells by Nahuoic Acid A

Abstract : Nahuoic acids A-E (1-5) have been isolated from laboratory cultures of a Streptomyces sp. obtained from a tropical marine sediment. The structures of the new polyketides 2-5 were elucidated by analysis of spectroscopic data of the natural products and the chemical derivatives 6 and 7. Nahuoic acids 1-5 are in vitro inhibitors of the histone methyltransferase SETD8, and nahuoic acid A (1) and its pentaacetate derivative 8 inhibit the proliferation of several cancer cells lines in vitro with modest potency. At the IC50 for cancer cell proliferation, nahuoic acid A (1) showed selective inhibition of SETD8 in U2OS osteosarcoma cells that reflect its selectivity against a panel of pure histone methyl transferases. A cell cycle analysis revealed that the cellular toxicity of nahuoic acid A (1) is likely linked to its ability to inhibit SETD8 activity.
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https://hal.umontpellier.fr/hal-02299117
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Soumis le : vendredi 27 septembre 2019 - 14:51:59
Dernière modification le : samedi 28 septembre 2019 - 01:20:23

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David Williams, Fanny Izard, Stéphanie Arnould, Doralyn Dalisay, Cholpisut Tantapakul, et al.. Structures of Nahuoic Acids B–E Produced in Culture by a Streptomyces sp. Isolated from a Marine Sediment and Evidence for the Inhibition of the Histone Methyl Transferase SETD8 in Human Cancer Cells by Nahuoic Acid A. Journal of Organic Chemistry, American Chemical Society, 2016, 81 (4), pp.1324-1332. ⟨10.1021/acs.joc.5b02569⟩. ⟨hal-02299117⟩

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