Kotoku, Naoyuki and Ishida, Ryosuke and Matsumoto, Hirokazu and Arai, Masayoshi and Toda, Kazunari and Setiawan, Andi and Muraoka, Osamu and Kobayashi, Motomasa (2017) Biakamides A−D, Unique Polyketides from a Marine Sponge, Act as Selective Growth Inhibitors of Tumor Cells Adapted to Nutrient Starvation. The Journal of Organic Chemistry, 82. pp. 1705-1718. ISSN 1520-6904

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Abstract

Biakamides A−D, novel unusually unique polyketides, were isolated from an Indonesian marine sponge (Petrosaspongia sp.) with a constructed bioassay using PANC-1 human pancreatic cancer cells. Through detailed analyses of the one- and two-dimensional NMR spectra of biakamides, planar chemical structures possessing a terminal thiazole, two N-methyl amides, a chloromethylene, and a substituted butyryl moiety were obtained. After elucidation of the configuration of the secondary alcohol moiety in biakamides A and B, the absolute stereostructures of the two secondary methyl groups in biakamides A−D were determined by the asymmetric total syntheses of all possible stereoisomers from the optically pure monoprotected 2,4-dimethyl-1,5-diol. Biakamides A−D showed selective antiproliferative activities against PANC-1 cells cultured under glucose-deficient conditions in a concentrationdependent manner. The primary mode of action of biakamides was found to be inhibition of complex I in the mitochondrial electron transport chain.

Item Type:	Article
Subjects:	Q Science > QD Chemistry
Divisions:	Fakultas Matematika dan Ilmu Pengetahuan Alam (FMIPA) > Prodi Kimia
Depositing User:	Prof Andi Setiawan
Date Deposited:	25 Jun 2018 02:26
Last Modified:	25 Jun 2018 02:26
URI:	http://repository.lppm.unila.ac.id/id/eprint/7631

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