TY - JOUR
T1 - Identification of novel long chain N-acylhomoserine lactones of chain length c20 from the marine phototrophic bacterium rhodovulum sulfidophilum
AU - Arashida, Naoko
AU - Shimbo, Kazutaka
AU - Terada, Takeshi
AU - Okimi, Takuya
AU - Kikuchi, Yo
AU - Hashiro, Shuhei
AU - Umekage, So
AU - Yasueda, Hisashi
PY - 2018/1/1
Y1 - 2018/1/1
N2 - 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.
AB - 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.
KW - Autoinducer
KW - C20-HSL
KW - LC-MS/MS
KW - N-acylhomoserine lactone (AHL)
KW - Rhodovulum sulfidophilum
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U2 - 10.1080/09168451.2018.1490168
DO - 10.1080/09168451.2018.1490168
M3 - Article
C2 - 30001674
AN - SCOPUS:85054097790
VL - 82
SP - 1683
EP - 1693
JO - Bioscience, Biotechnology and Biochemistry
JF - Bioscience, Biotechnology and Biochemistry
SN - 0916-8451
IS - 10
ER -