np7b00184_si_001.pdf (3.75 MB)
Sulawesins A–C, Furanosesterterpene Tetronic Acids That Inhibit USP7, from a Psammocinia sp. Marine Sponge
journal contribution
posted on 2017-06-16, 18:20 authored by Ahmed
H. Afifi, Ippei Kagiyama, Ahmed H. El-Desoky, Hikaru Kato, Remy E. P. Mangindaan, Nicole J. de Voogd, Nagwa M. Ammar, Mohammed S. Hifnawy, Sachiko TsukamotoThree new furanosesterterpene tetronic
acids, sulawesins A–C
(1–3), were isolated from a Psammocinia sp. marine sponge, along with the known compounds
ircinins-1 (4) and -2 (5). Although ircinins-1
and -2 were previously isolated as (+)- or (−)-enantiomers
from marine sponges, we isolated them as enantiomeric mixtures. Sulawesins
A and B possess a new carbon skeleton with a 5-(furan-3-yl)-4-hydroxycyclopent-2-enone
moiety and were also found to be diastereomeric mixtures of four isomers
by an HPLC analysis with a chiral-phase column. Sulawesin C has a
dimeric structure of ircinin-1 and is the first dimer in this family.
USP7, a deubiquitinating enzyme, is an emergent target of cancer therapy,
and the isolated compounds inhibited USP7 with IC50 values
in the range of 2.7–4.6 μM.