Bananamides D – G

General info

Original publication	Omoboye, 2019
Original source	Pseudomonas koreensis COW3
Other known sources (non-putative)	n.a.
Stereochemistry determined by	n.a.

Chemical properties

CAS	n.a.
Molecular formula	C53H92N8O14
Molecular weight	1063.4 g/mol
Mono-isotopic mass	1064.6733 Da
Solubility	Methanol, acetonitrile, DMF, DMSO
CMC	n.a.
Minimal surface tension	n.a.
3D conformation	n.a.
NMR data available in literature	DMF-d7 (Omoboye, 2019)

Introduction

Bananamides D – G are cyclic lipodepsipeptides that were first extracted from the cocoyam rhizosphere-derived biocontrol strain Pseudomonas koreensis COW3. These CLiPs induce antagonistic activity against several fungi. Structurally, they belong to the bananamide group.

Biological activity

Purified bananamides D -G induce antagonistic activity and mycophagy against Pythium myriotylum between 1 µM and 50 µM, while it mainly shows mycophagy on Pyricularia oryzae in the same concentration range.

Chemical structure

The chemical structures of bananamides D through G were characterized by means of NMR spectroscopy and mass spectrometry. (Omoboye, 2019) These CLiPs consist of 8 amino acids, 6 of which are involved in the macrocycle formed by an ester bond between the C-terminal carboxylic acid and the side chain hydroxyl moiety of Thr3. The bananamides D – G differ solely in the length and saturation of the N-terminal fatty acid tail.

Structurally, bananamides D – G belong to the bananamide group. This group of lipopeptides consists of its name-sake CLiPs bananamides 1 – 3 (also known as bananamides A – C) (Nguyen, 2016) and MDN-0066 (Cautain, 2015). Withing this group, variations are located at position 6 (featuring either Ser6 or Gln6), position 2 (Glu2 or Asp2) or the fatty acid tail. Finally, the stereochemistries of the bananamide D – G remain unknow. Within the bananamide group, only the stereochemical make-up of MDN-0066 has be elucidated.

NMR fingerprint data

Recently, it was established that the planar structure and stereochemistry of CLiPs can be assessed by simple comparison to a reference. (De Roo, 2022) More specifically, by matching NMR spectra of a CLiP from a newly isolated bacterial source with those of existing (reference) CLiPs, one can determine whether they are identical or not. A detailed explanation on what NMR fingerprint matching is, and how to use it, can be found here.

Below, we provide the reference NMR data of bananamides D – G in various formats. These data are recorded in DMF-d7 at room temperature, and can be used to asses similarities of newly isolated CLiPs to the bananamides D – G.

References

Cautain, et al. “Identification of the lipodepsipeptide MDN-0066, a novel inhibitor of VHL/HIF pathway produced by a new Pseudomonas species.” PLoS One10, 5 (2015): https://dx.doi.org/10.1371/journal.pone.0125221.

De Roo, et al. “An nuclear magnetic resonance fingerprint matching approach for the identification and structural re-evaluation of Pseudomonas lipopeptides.” Microbiology Spectrum (2022) https://dx.doi.org/doi:10.1128/spectrum.

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.

Omoboye, et al. “Pseudomonas sp. COW3 Produces New Bananamide-Type Cyclic Lipopeptides with Antimicrobial Activity against Pythium myriotylum and Pyricularia oryzae.” Molecules24, 22 (2019): https://dx.doi.org/10.3390/molecules24224170.

External links

Bananamide D: NORINE database and PubChem

Bananamide E NORINE database and PubChem

Bananamide F: NORINE database and PubChem

Bananamide G NORINE database and PubChem