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@ARTICLE{Mokhlesi:841560,
author = {Mokhlesi, Amin and Stuhldreier, Fabian and Wex, Katharina
W. and Berscheid, Anne and Hartmann, Rudolf and Rehberg,
Nidja and Sureechatchaiyan, Parichat and Chaidir, Chaidir
and Kassack, Matthias and Kalscheuer, Rainer and
Brötz-Oesterhelt, Heike and Wesselborg, Sebastian and
Stork, Björn and Daletos, Georgios and Proksch, Peter},
title = {{C}yclic {C}ystine-{B}ridged {P}eptides from the {M}arine
{S}ponge {C}lathria basilana {I}nduce {A}poptosis in {T}umor
{C}ells and {D}epolarize the {B}acterial {C}ytoplasmic
{M}embrane},
journal = {Journal of natural products},
volume = {80},
number = {11},
issn = {0163-3864},
address = {Washington, DC},
publisher = {Soc.},
reportid = {FZJ-2017-08598},
pages = {2941–2952},
year = {2017},
abstract = {Investigation of the sponge Clathria basilana collected in
Indonesia afforded five new peptides, including
microcionamides C (1) and D (2), gombamides B (4), C (5),
and D (6), and an unusual amide,
(E)-2-amino-3-methyl-N-styrylbutanamide (7), along with 11
known compounds, among them microcionamide A (3). The
structures of the new compounds were elucidated by one- and
two-dimensional NMR spectroscopy as well as by
high-resolution mass spectrometry. The absolute
configurations of the constituent amino acid residues in
1–7 were determined by Marfey’s analysis.
Microcionamides A, C, and D (1–3) showed in vitro
cytotoxicity against lymphoma (Ramos) and leukemia cell
lines (HL-60, Nomo-1, Jurkat J16), as well as against a
human ovarian carcinoma cell line (A2780) with IC50 values
ranging from 0.45 to 28 μM. Mechanistic studies showed that
compounds 1–3 rapidly induce apoptotic cell death in
Jurkat J16 and Ramos cells and that 1 and 2 potently block
autophagy upon starvation conditions, thereby impairing
pro-survival signaling of cancer cells. In addition,
microcionamides C and A (1 and 3) inhibited bacterial growth
of Staphylococcus aureus and Enterococcus faecium with
minimal inhibitory concentrations between 6.2 and 12 μM.
Mechanistic studies indicate dissipation of the bacterial
membrane potential.},
cin = {ICS-6},
ddc = {500},
cid = {I:(DE-Juel1)ICS-6-20110106},
pnm = {551 - Functional Macromolecules and Complexes (POF3-551)},
pid = {G:(DE-HGF)POF3-551},
typ = {PUB:(DE-HGF)16},
pubmed = {pmid:29094598},
UT = {WOS:000416500400011},
doi = {10.1021/acs.jnatprod.7b00477},
url = {https://juser.fz-juelich.de/record/841560},
}