Abstract
A bioassay-guided investigation (cancer cell cytotoxicity) of a Moorea producens collection from Key West, Florida, led to the discovery of two new bioactive natural products [(+)-malyngamide Y and a cyclic depsipeptide, (+)-floridamide]. Their planar structures were deduced through extensive analysis of 1D and 2D NMR spectroscopic data and supported by HRFAB mass spectrometry. The new cyclic depsipeptide contains four amino acids units, including N-methyl phenylalanine, proline, valine and alanine, beside the unique unit, 2,2-dimethyl-3-hydroxy-octanoic acid. In addition to the discovery of these two new compounds, two previously reported metabolites were also isolated and identified from this cyanobacterial collection; (−)-C-12 lyngbic acid and the antibacterial agent (−)-malyngolide.
Highlights
A large number of collections of the marine cyanobacterium Moorea producens produce a class of lipopeptide metabolite known as the ‘malyngamides’(Cardellina et al 1978; Moore et al 1978, Ainslie et al 1985; Wright et al 1990; Mynderse, et al 1978; Gerwick et al 1987; Engene et al 2012)
Successive reversed phase solid phase extraction (SPE) and HPLC fractionation resulted in the isolation of two new compounds (1, 2), in addition to two previously known compounds (3, 4)
The isotope pattern observed for the molecular ion (FAB) indicated the presence of one chlorine atom, and HRFABMS established a molecular formula of C23H37ClNO3
Summary
A large number of collections of the marine cyanobacterium Moorea producens produce a class of lipopeptide metabolite known as the ‘malyngamides’(Cardellina et al 1978; Moore et al 1978, Ainslie et al 1985; Wright et al 1990; Mynderse, et al 1978; Gerwick et al 1987; Engene et al 2012). There are two distinct and characteristic portions comprising the malyngamides; a methoxy fatty acid (known trivially as lyngbic acid) and a variety of functionalized amines, linked through an amide bond. These lyngbic acids have varying chain lengths, ranging from C-12 to C-20, with a methoxy group at C-7 as well as a trans double bond at C-4. Two metabolites of known identity were isolated, namely the anti-microbial (−)-malyngolide (3) and the (−)-C-12 lyngbic acid (4)
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