title: Yakushinamides, Polyoxygenated Fatty Acid Amides That Inhibit HDACs and SIRTs, from the Marine Sponge Theonella swinhoei.
abstract: Yakushinamides A (1) and B (2), prolyl amides of polyoxygenated fatty acids, have been isolated from the marine sponge Theonella swinhoei 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 1 and 2, 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 1 and the isolated 1-hydroxy-2-methyl moiety in 2, we found diagnostic NMR features to distinguish each pair of diastereomers. The absolute configurations of 1 and 2 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 1, this method gave an ambiguous result at C-20 when applied to the methanolysis product of 2, even after oxidative cleavage of the C-14 and C-15 bond.
authors.affiliation: Laboratory of Aquatic Natural Products Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo , Bunkyo-ku, Tokyo 113-8657, Japan.
authors.forename: Kentaro
authors.initials: K
authors.lastname: Takada
authors.affiliation: Laboratory of Aquatic Natural Products Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo , Bunkyo-ku, Tokyo 113-8657, Japan.
authors.forename: Yasufumi
authors.initials: Y
authors.lastname: Imae
authors.affiliation: Sugashima Marine Biological Laboratory, Nagoya University , Toba, Mie 517-0004, Japan.
authors.forename: Yuji
authors.initials: Y
authors.lastname: Ise
authors.affiliation: Takehara Marine Station, Hiroshima University , Takehara, Hiroshima 725-0024, Japan.
authors.forename: Susumu
authors.initials: S
authors.lastname: Ohtsuka
authors.affiliation: Chemical Genomics Reserach Group, RIKEN Center for Sustainable Resource Science , Wako, Saitama 351-0198, Japan.|Chemical Genetics Laboratory, RIKEN , Wako, Saitama 351-0198, Japan.
authors.forename: Akihiro
authors.initials: A
authors.lastname: Ito
authors.affiliation: Laboratory of Aquatic Natural Products Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo , Bunkyo-ku, Tokyo 113-8657, Japan.
authors.forename: Shigeru
authors.initials: S
authors.lastname: Okada
authors.affiliation: Chemical Genomics Reserach Group, RIKEN Center for Sustainable Resource Science , Wako, Saitama 351-0198, Japan.|Chemical Genetics Laboratory, RIKEN , Wako, Saitama 351-0198, Japan.
authors.forename: Minoru
authors.initials: M
authors.lastname: Yoshida
authors.affiliation: Laboratory of Aquatic Natural Products Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo , Bunkyo-ku, Tokyo 113-8657, Japan.
authors.forename: Shigeki
authors.initials: S
authors.lastname: Matsunaga
mesh_terms: D000577:Amides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D000818:Animals; D005227:Fatty Acids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D006655:Histone Deacetylases; D007564:Japan; D008386:Marine Biology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D009792:Oceans and Seas; D010456:Peptides, Cyclic / Q000737:chemistry; D047232:Theonella / Q000737:chemistry*
chemical_list: D000577:Amides; D005227:Fatty Acids; D010456:Peptides, Cyclic; C000620760:yakushinamide A; C000620761:yakushinamide B; D006655:Histone Deacetylases