Marilines A-C: novel phthalimidines from the sponge-derived fungus Stachylidium sp.
A marine-derived fungus of the genus Stachylidium was isolated from the sponge Callyspongia cf. C. flammea. Chemical investigation of the bioactive fungal extract led to the isolation of the novel phthalimidine derivatives marilines A(1) (1a), A(2) (1b), B (2), and C (3). The absolute configurations of the enantiomeric compounds 1a and 1b were assigned by a combination of experimental circular dichroism (CD) investigations and quantum chemical CD calculations. The skeleton of marilines is most unusual, and its biosynthesis is suggested to require uncommon biochemical reactions in fungal secondary metabolism. Both enantiomers, marilines A(1) (1a) and A(2) (1b), inhibited human leukocyte elastase (HLE) with an IC(50) value of 0.86 μM.
Institute for Pharmaceutical Biology, University of Bonn, Nussallee 6, 53115 Bonn, Germany.
Celso
C
Almeida
Yasmin
Y
Hemberger
Sven Marcel
SM
Schmitt
Sarah
S
Bouhired
Lavanya
L
Natesan
Stefan
S
Kehraus
Konstantinos
K
Dimas
Michael
M
Gütschow
Gerhard
G
Bringmann
Gabriele M
GM
König
D000818:Animals; D001203:Ascomycota / Q000737:chemistry*; D006801:Humans; D019272:Leukocyte Elastase / Q000037:antagonists & inhibitors*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010797:Phthalimides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D011161:Porifera / Q000382:microbiology*
D010797:Phthalimides; C575597:mariline A; C575598:mariline B; C575599:mariline C; C037432:phthalimidine; D019272:Leukocyte Elastase