10.1021/acs.jnatprod.6b00588.s001 Kentaro Takada Kentaro Takada Yasufumi Imae Yasufumi Imae Yuji Ise Yuji Ise Susumu Ohtsuka Susumu Ohtsuka Akihiro Ito Akihiro Ito Shigeru Okada Shigeru Okada Minoru Yoshida Minoru Yoshida Shigeki Matsunaga Shigeki Matsunaga Yakushinamides, Polyoxygenated Fatty Acid Amides That Inhibit HDACs and SIRTs, from the Marine Sponge <i>Theonella swinhoei</i> American Chemical Society 2016 C -15 bond marine sponge Theonella swinhoei 1- hydroxy -3-methyl moiety HDAC methanolysis products assignment 1- hydroxy -2-methyl moiety SIRT configuration Marine Sponge Theonella swinhoei Yakushinamides NMR tandem FABMS data Mosher method methanolysis product 2016-08-22 13:03:42 Journal contribution https://acs.figshare.com/articles/journal_contribution/Yakushinamides_Polyoxygenated_Fatty_Acid_Amides_That_Inhibit_HDACs_and_SIRTs_from_the_Marine_Sponge_i_Theonella_swinhoei_i_/3749532 Yakushinamides A (<b>1</b>) and B (<b>2</b>), prolyl amides of polyoxygenated fatty acids, have been isolated from the marine sponge <i>Theonella swinhoei</i> as inhibitors of HDACs and SIRTs. Their planar structures were determined by interpretation of the NMR data of the intact molecules and tandem FABMS data of the methanolysis products. For the assignment of the relative configurations of the three contiguous oxymethine carbons in <b>1</b> and <b>2</b>, Kishi’s universal NMR database was applied to the methanolysis products. During the assignments of relative configurations of the isolated 1-hydroxy-3-methyl moiety in <b>1</b> and the isolated 1-hydroxy-2-methyl moiety in <b>2</b>, we found diagnostic NMR features to distinguish each pair of diastereomers. The absolute configurations of <b>1</b> and <b>2</b> were determined by a combination of the modified Mosher’s method and Marfey’s method. Although the modified Mosher’s method was successfully applied to the methanolysis product of <b>1</b>, this method gave an ambiguous result at C-20 when applied to the methanolysis product of <b>2</b>, even after oxidative cleavage of the C-14 and C-15 bond.