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.