Identification of novel long chain N-acylhomoserine lactones of chain length C20 from the marine phototrophic bacterium Rhodovulum sulfidophilum
Identification of novel long chain N-acylhomoserine lactones of chain length C20 from the marine phototrophic bacterium Rhodovulum sulfidophilum
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DOI：
10.1080/09168451.2018.1490168
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发表时间：
2018-01-01
影响因子：
1.6
通讯作者：
Yasueda, Hisashi
中科院分区：
文献类型：
--
作者：
Arashida, Naoko;Shimbo, Kazutaka;Yasueda, Hisashi
革兰氏阴性菌群体感应主要由细胞外产生的N-酰基高丝氨酸内酯（阿勒）调节。阿勒由内酯环和酰基链组成，其长度通常从C-4到C-18不等，并提供物种特异性变化。建立了超高效液相色谱-串联质谱系统，并从海洋光合细菌Rhodovulum sulfidophilum的培养上清液中检测到两种链长为C-20的长链AHLs。通过碎片搜索分析，发现了少量的阿勒，推测为3-OH-C-18-homoserine lactone（HSL），其中3-OH-C-20-HSL的结构被确定，强烈建议为3-OH-C-20：1-HSL。据我们所知，这是第一份报告，以显示一个新的阿勒与最长的C-20酰基侧链发现的日期。缩写：AGC：自动增益控制;阿勒：N-酰基高丝氨酸内酯; CD：环糊精; CID：碰撞诱导解离; DDA：数据依赖采集; EPI：增强的产物离子; FISh：碎片离子搜索; HCD：高能碰撞解离; HSL：高丝氨酸内酯; IT：进样时间; LC：液相色谱; MS：质谱; PRM：平行反应监测; RP：反相; SRM：选择反应监测; TLC：薄层色谱; UHPLC：超高效液相色谱
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 C-4 to C-18 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 C-20 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-C-18-homoserine lactone (HSL), was also found. Among the detected C-20-HSLs, 3-OH-C-20-HSL was structurally identified and 3-OH-C-20:1-HSL was strongly suggested. To our knowledge, this is the first report to show a novel AHL with the longest C-20 acyl side chain found to date.Abbreviations: 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 dissociation; HSL: homoserine lactone; IT: injection time; LC: liquid chromatography; MS: mass spectrometry; PRM: parallel reaction monitoring; RP: reverse phase; SRM: selected reaction monitoring; TLC: thin layer chromatography; UHPLC: ultra high performance liquid chromatography