Identification of novel long chain N-acylhomoserine lactones of chain length c20 from the marine phototrophic bacterium rhodovulum sulfidophilum

Naoko Arashida, Kazutaka Shimbo*, Takeshi Terada, Takuya Okimi, Yo Kikuchi, Shuhei Hashiro, So Umekage, Hisashi Yasueda

*Corresponding author for this work

    Research output: Contribution to journalArticlepeer-review

    7 Citations (Scopus)

    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.

    Original languageEnglish
    Pages (from-to)1683-1693
    Number of pages11
    JournalBioscience, Biotechnology and Biochemistry
    Volume82
    Issue number10
    DOIs
    Publication statusPublished - 2018 Jan 1

    Keywords

    • Autoinducer
    • C20-HSL
    • LC-MS/MS
    • N-acylhomoserine lactone (AHL)
    • Rhodovulum sulfidophilum

    ASJC Scopus subject areas

    • Biotechnology
    • Analytical Chemistry
    • Biochemistry
    • Applied Microbiology and Biotechnology
    • Molecular Biology
    • Organic Chemistry

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