Orfamide group

The Orfamide group is a collection of structurally similar cyclic lipopeptides (CLiPs) as produced by various Pseudomonas bacteria. The group owes its name to the cyclic lipopeptide orfamide A (Gross, 2007). Other CLiPs of this group include orfamide B (Ma, 2016), orfamide C (Gross, 2007), orfamides D – G (Ma, 2016), orfamide H (Ma, 2019), orfamide J – M (De Roo, 2022), poaeamide A (Zachow, 2015), poaeamide B (Nguyen, 2016) and the PPZMs (Weisshoff, 2014).

The group features CLiPs with a decapeptide chain, cyclized via an ester bond between the C-terminal carbonyl and the side chain of D-aThr3. At the N-terminal they are linked to a 3-hydroxy fatty. Structural variations that appear within the Orfamide group are mostly related to this fatty acid moiety, with differences occurring in both tail length and saturation.

Currently, no three-dimensional structures are known for the Orfamide group members.

The orfamides generally appear to possess antifungal and insecticidal properties (Jang, 2013, Ma, 2016). Finally, no antibacterial activities have been described for the Orfamide group members. (Geudens, 2018)

References

Geudens, et al. “Cyclic lipodepsipeptides from Pseudomonas spp. – Biological Swiss-Army Knives.” Frontiers in Microbiology9, 1867 (2018): https://dx.doi.org/10.3389/fmicb.2018.01867.

Gross, et al. “The genomisotopic approach: a systematic method to isolate products of orphan biosynthetic gene clusters.” Chemistry & Biology14, 1 (2007): https://dx.doi.org/10.1016/j.chembiol.2006.11.007.

Jang, et al. “Identification of orfamide A as an insecticidal metabolite produced by Pseudomonas protegens F6.” Journal of Agricultural and Food Chemistry61, 28 (2013): https://dx.doi.org/10.1021/jf401218w.

Ma, et al. “Biosynthesis, chemical structure, and structure-activity relationship of orfamide lipopeptides produced by Pseudomonas protegens and related species.” Frontiers in Microbiology7 (2016): https://dx.doi.org/10.3389/fmicb.2016.00382.

Ma, et al. “Isolation and characterization of a new cyclic lipopeptide orfamide H from Pseudomonas protegens CHA0.” Journal of Antibiotics (2019): https://dx.doi.org/10.1038/s41429-019-0254-0.

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.

Weisshoff, et al. “PPZPMs – a novel group of cyclic lipodepsipeptides produced by the Phytophtora alni associated strain Pseudomonas sp. JX090307 – the missing link between the viscosin and amphisin group.” Natural Products Communications9, 7 (2014).

Zachow, et al. “The novel lipopeptide poaeamide of the endophyte Pseudomonas poae RE*1-1-14 is involved in pathogen suppression and root colonization.” Molecular Plant-Microbe Interactions28, 7 (2015): https://dx.doi.org/10.1094/MPMI-12-14-0406-R.