Cytotoxic Fatty Acid Amides from Xenorhabdus

Abstract

Simple and bioactive: 26 acyl amides have been identified in cultures of different Xenorhabdus strains and several analogues have been synthesised. Despite their simple chemical structure, several of these compounds show cytotoxicity against mammalian cell lines and insect haemocytes, thus indicating that they have a role in the complex life cycle of these bacteria.

Identification and isolation of insecticidal oxazoles from Pseudomonas spp.

“…Compounds 3 , 5 , 6 , and 9 are active in the MCF-7 assay with EC 50 [µg ml −1 ] values of 58, 363, 26, and 34, respectively. Similar to previous results [19], several tryptamine amide derivatives ( 20 – 24 , 26 ) showed cytotoxic activity against the MCF-7 cells with 24 being the most potent compound (1.02 µg ml −1 ). Interestingly, 26 also showed activity against Galleria hemocytes, although its oxazole derivative 10 did not, which may point to different targets for both compound classes.…”

“…We tested the bioactivity against the human breast-cancer cell line MCF-7, using the XTT assay [18], and against insect hemocytes from the greater wax moth Galleria melonella according to the method described by Proschak et al [19]. Three oxazole compounds show LD 50 [µg ml −1 ] values against Galleria hemocytes of 30 (compound 3 ), 1.7 (compound 6 ), and 103 (compound 9 ) (Table S7).…”

Discovery and Characterization of Gut Microbiota Decarboxylases that Can Produce the Neurotransmitter Tryptamine

“…First, while the decarboxylation of tryptophan to tryptamine is common in the plant kingdom (Facchini et al, 2000), Trp decarboxylation is an exceedingly rare activity among bacteria. To our knowledge, the only bacterial species in which this transformation is known are Xenorhabdus nematophilus and Bacillus atrophaeus , which are thought to produce tryptamine as a building block for the biosynthesis of larger natural products (Lang et al, 2008; Li et al, 1997; Proschak et al, 2011; Yuwen et al, 2013), and Lactobacillus bulgaricus , the only bacterial species known to excrete tryptamine (Chander et al, 1989). …”

Edonamides, the first secondary metabolites from the recently described myxobacterium Aggregicoccus edonensis

“…However, small changes in the fatty acid chain, for example removing a methyl-group, sufficed to get cometabolites with cytotoxic activity similar to 2. 20 Comparing the straight chain fatty-acid of 2 brought up quorum-sensing inhibitors like N-octanoyl-3-amino-2-cyclohexen-1-one from Burkholderia glumae, 21 siderophores such as corrugatin from Pseudomonas corrugata 22 and antibiotics like fragin from Pseudomonas fragi 23,24 . Also the fatty acid residue can be found in pigments like lemonnierin from Pseudomonas lemonnieri.…”