Kotoku, Naoyuki and Ishida, Ryosuke and Matsumoto, Hirokazu and Arai, Masayoshi and Toda, Kazunari and Setiawan, Andi and Muraoka, Osamu and Kobayashi, Motomasa Biakamides A–D, unique polyketides from a marine sponge, act as selective growth inhibitors of tumor cells adapted to nutrient starvation. ACS Publication.

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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 nuclear magnetic resonance (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 concentration-dependent manner. The primary mode of action of biakamides was found to be inhibition of complex I in the mitochondrial electron transport chain.

Item Type: Other
Subjects: Q Science > Q Science (General)
Depositing User: Dr. Andi Setiawan
Date Deposited: 17 Feb 2022 07:49
Last Modified: 17 Feb 2022 07:49
URI: http://repository.lppm.unila.ac.id/id/eprint/39439

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