A search for BACE inhibitors reveals new biosynthetically related pyrrolidones, furanones and pyrroles from a southern Australian marine sponge, Ianthella sp.

Zhang, Hua, Conte, Melissa M., Huang, Xiao-Cong, Khalil, Zeinab and Capon, Robert J. (2012) A search for BACE inhibitors reveals new biosynthetically related pyrrolidones, furanones and pyrroles from a southern Australian marine sponge, Ianthella sp.. Organic and Biomolecular Chemistry, 10 13: 2656-2663.


Author Zhang, Hua
Conte, Melissa M.
Huang, Xiao-Cong
Khalil, Zeinab
Capon, Robert J.
Title A search for BACE inhibitors reveals new biosynthetically related pyrrolidones, furanones and pyrroles from a southern Australian marine sponge, Ianthella sp.
Journal name Organic and Biomolecular Chemistry  (ERA 2012 Listed)    (ERA 2010 Rank A*)   Check publisher's open access policy
Publication date 2012-04
Sub-type Article
DOI 10.1039/c2ob06747a
Volume number 10
Issue number 13
ISSN 1477-0520;1477-0539
Start page 2656
End page 2663
Total pages 8
Place of publication Cambridge, United Kingdom
Publisher Royal Society of Chemistry
Collection year 2013
Language eng
Formatted abstract Fractionation of a southern Australian marine sponge, Ianthella sp., yielded sixteen metabolites including a new class of pyrrolidone, ianthellidones A-F (1-6), a new class of furanone, ianthellidones G-H (7-8), new and known lamellarins, lamellarins O1 (9), O2 (10), O (11) and Q (12), plus the known 4-hydroxybenzaldehyde (13), 4-hydroxybenzoic acid (14), 4-methoxybenzoic acid (15) and ethyl 4-hydroxybenzoate (16). Structures for all Ianthella metabolites were determined by detailed spectroscopic analysis, supported by a plausible biosynthetic relationship. The ianthellidones were non-cytotoxic towards two human colon cancer cell lines (SW620 and SW620 Ad300), as well as Gram +ve and Gram -ve bacteria, and a fungus. Ianthellidone F (6) and lamellarins O2 (10) and O (11) displayed modest BACE inhibitory properties (IC 50 > 10 μM), while lamellarin O1 (9) was more potent (IC 50 < 10 μM). Lamellarin O (11) exhibited modest cytotoxicity towards SW620 and SW620 Ad300 cell lines (IC 50 > 22 μM), was an inhibitor of the multi-drug resistance efflux pump P-glycoprotein, and displayed selective growth inhibitory activity against the Gram +ve bacterium Bacillus subtilis (ATCC 6633) (IC 50 2.5 μM).
Keyword Aromatic Metabolites
Dendrilla-Cactos
Alkaloids
Assay
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ
Additional Notes First published on the web 13 January 2012.

Document type: Journal Article
Sub-type: Article
Collections: Official 2013 Collection
Institute for Molecular Bioscience - Publications
 
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