2 research outputs found
Isolation of Ciliatamide D from a Marine Sponge <i>Stelletta</i> sp. and a Reinvestigation of the Configuration of Ciliatamide A
A new lipopeptide, ciliatamide D
(<b>1</b>), was isolated from a marine sponge <i>Stelletta</i> sp., collected at Oshimashinsone, together with the known compound
ciliatamide A (<b>2</b>). Ciliatamide D (<b>1</b>) is
a congener of <b>2</b>, in which <i>N</i>-Me-Phe is
replaced by <i>N</i>-Me-MetÂ(O). Marfey’s analysis
of the acid hydrolysate of <b>1</b> demonstrated that the two
constituent amino acids were both in the l-form. This result
prompted us to carefully investigate the configuration of <b>2</b>, resulting in the assignment of the l-form for both residues
Yakushinamides, Polyoxygenated Fatty Acid Amides That Inhibit HDACs and SIRTs, from the Marine Sponge <i>Theonella swinhoei</i>
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