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

    Research output: Contribution to journalArticlepeer-review

    6 Citations (Scopus)


    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
    Issue number10
    Publication statusPublished - 2018 Jan 1


    • 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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