Bananamides D – G

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General info

Original publicationOmoboye, 2019
Original sourcePseudomonas koreensis. COW3
Other known sources (non-putative)n.a.
Stereochemistry determined byn.a.

Chemical properties

CASn.a.
Molecular formulaC53H92N8O14
Molecular weight1063.4 g/mol
Mono-isotopic mass1064.6733 Da
SolubilityMethanol, acetonitrile, DMF-d7, DMSO
CMCn.a.
Minimal surface tensionn.a.
3D conformationn.a.
NMR data available in literatureDMF-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.

Chemical structure of bananamide D.

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 stereochemistry of all bananamide group members, including bananamide D – G, remains unknow.

Schematic representation of the structures of 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.

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

Vorige MDN-0066
Volgende Bananamide group