Bananamides 1 – 3
|Original publication||Nguyen, 2016|
|Original source||Pseudomonas fluorescens BW11P2|
|Other known sources (non-putative)||–|
|Stereochemistry determined by||Not determined|
|Molecular weight||1108.4 g/mol|
|Mono-isotopic mass||1107.7155 Da|
|Minimal surface tension||–|
|NMR data available in literature||Methanol-d4 (Nguyen, 2016)|
Bananamides 1, 2 and 3 were discovered by indexing the pseudomonas metabolome through the molecular networking of mass spectrometric sequence tags. Their producing bacterium, P. fluorescens BW11P2, was collected from the banana rhizoplane in the wetlands of Galagedara (Sri Lanka) and represents the only non-putative source of bananamides 1 – 3 to date.
Using MS/MS and liquid state NMR spectroscopy, it was determined that bananamides 1, 2 and 3 all have an identical amino acid sequence, being Leu1 – Asp2 – Thr3 – Leu4 – Leu5 – Gln6 – Leu7 – Ile8, whereby the molecule is cyclized by means of an ester bond between the C-terminal carbonyl carbon of the side chain hydroxyl moiety of Thr3. Both compound differ only in their N-terminal fatty acid moiety, being 3-hydroxy dodecanoic acid (3-OH C12:0), 3-hydroxy dodecenoic acid (3-OH C12:1) and 3-hydroxy decanoic acid (3-OH C10:0) respectively. No information is available concerning the stereochemistry of the individual amino acids.
They are the namesake CLiPs of the bananamide group; a collection of structurally similar cyclic lipodepsipeptides such as MDN-0066 and bananamides D – G.
Nguyen, et al. “Indexing the Pseudomonas specialized metabolome enabled the discovery of poaeamide B and the bananamides.” Nature Microbiology2 (2016): https://dx.doi.org/10.1038/nmicrobiol.2016.197.