Bananamide group

Introduction

The bananamides are a collection of secondary metabolites produced by Pseudomonas species. They consist of a octapeptide chain, whereby 6 amino acids are involved in a macrocycle formed by an ester bond. Within the group, variations occur at position 2 (Asp vs. Glu), position 6 (Gln vs Ser) or position 8 (Ile vs Val). The pioneering member of the bananamide group, MDN-0066, was described in 2015 for its anticancer activities. (Cautain, 2015) Shortly after, bananamides I-III were characterized while conducting a large scale metabolomic study of Pseudomonas strains. (Nguyen, 2016) Since then, other bananamide-isoforms have been characterized, named bananamides D – G. (Omoboye, 2019) 

Biological activity

There is only limited data available on the biological activities of bananamide group members. Bananamide D – G induced antagonistic effects on fungi (Pyricularia oryzae GUY11 and VT5M1), at concentrations ranging from 1 to 50 µM. No information is available on their activity against other microorganisms. In a biomedical context, MDN0066 was found to be cytotoxic to certain cancer cell lines, inducing apoptosis below cytotoxic levels.

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.