Identification of novel long chain N-acylhomoserine lactones of chain length C20 from the marine phototrophic bacterium Rhodovulum sulfidophilum

Bioscience, Biotechnology, and Biochemistry
Naoko ArashidaHisashi Yasueda

Abstract

Gram-negative bacterial quorum sensing is mainly regulated by an extracellularly produced N-acylhomoserine lactone (AHL). AHL consists of a lactone ring and an acyl chain, which generally varies from C4 to C18 in length and affords species-specific variety. In this study, we developed an ultra-high performance liquid chromatography tandem mass spectrometry system and detected two kinds of long chain AHLs with chain length C20 from the reverse-phase thin layer chromatography-fractionated cultured supernatant of the marine photosynthetic bacterium Rhodovulum sulfidophilum. By fragmentation search analysis to detect compounds with a homoserine lactone ring moiety for data dependent acquisition, a minor AHL, presumed to be 3-OH-C18-homoserine lactone (HSL), was also found. Among the detected C20-HSLs, 3-OH-C20-HSL was structurally identified and 3-OH-C20:1-HSL was strongly suggested. To our knowledge, this is the first report to show a novel AHL with the longest C20 acyl side chain found to date. AGC: automatic gain control; AHL: N-acylhomoserine lactone; CD: cyclodextrin; CID: collision induced dissociation; DDA: data dependent acquisition; EPI: enhanced product ion; FISh: fragment ion search; HCD: high energy collisional dissocia...Continue Reading

References

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Citations

Apr 26, 2019·Bioscience, Biotechnology, and Biochemistry·Masanori Toyofuku
Feb 7, 2020·Natural Product Reports·Anthony R CarrollMichèle R Prinsep
Apr 16, 2020·Environmental Microbiology Reports·Kana MorinagaMasanori Toyofuku
Feb 1, 2020·Applied Microbiology and Biotechnology·Kana MorinagaMasanori Toyofuku
Feb 4, 2022·Journal of Natural Products·Jessica M DeutschNeha Garg

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