The effects of betonicine, floridoside, and isethionic acid from the red alga Ahnfeltiopsis flabelliformis on quorum-sensing activity

被引:32
作者
Liu, Hai Bo [1 ,2 ]
Koh, Kyong Pyo [1 ,2 ]
Kim, Jung Sun [3 ]
Seo, Youngwan [4 ]
Park, Sunghoon [1 ,2 ]
机构
[1] Pusan Natl Univ, Dept Chem & Biochem Engn, Pusan 609735, South Korea
[2] Pusan Natl Univ, Inst Environm Technol & Ind, Pusan 609735, South Korea
[3] Dongseo Univ, Div Hlth Sci, Pusan 617716, South Korea
[4] Korea Maritime Univ, Div Marine Environm & Biosci, Pusan 606791, South Korea
关键词
quorum-sensing inhibitor; AHL inhibitor; Ahnfeltiopsis flabelliformis; Agrobacterium tumefaciens; betonicine; floridoside; isethionic acid;
D O I
10.1007/s12257-008-0145-x
中图分类号
Q81 [生物工程学(生物技术)]; Q93 [微生物学];
学科分类号
071005 ; 0836 ; 090102 ; 100705 ;
摘要
A mixture of three compounds (betonicine, floridoside, and isethionic acid) purified from the red alga Ahnfeltiopsis flabelliformis, was reported to have an inhibition activity on bacterial quorum sensing mechanism mediated by N-octanoyl-DL-homoserine lactone (OHL) and the TraR transcriptional activator protein. We subsequently conducted a more detailed investigation of the three compounds using chemically synthesized (betonicine and floridoside) or commercially available (isethionic acid) compounds, individually or in various combinations. When tested alone, none of the three compounds inhibited OHL, but a mixture of floridoside and isethionic acid exhibited a dose-dependent inhibitory effect on the function of OHL. In contrast, betonicine or its isomer exhibited a dose-dependent stimulatory effect, similar to OHL, at concentrations between 10(-3) and 10(-6) M. These three compounds will be useful for elucidating the interaction between OHL and TraR, and for developing novel bacterial quorum-sensing inhibitors. (c) KSBB.
引用
收藏
页码:458 / 463
页数:6
相关论文
共 24 条
[11]   Reinvestigation of the sulfuric acid-catalysed cyclisation of brominated 2-alkyllevulinic acids to 3-alkyl-5-methylene-2(5H)-furanones [J].
Manny, AJ ;
Kjelleberg, S ;
Kumar, N ;
deNys, R ;
Read, RW ;
Steinberg, P .
TETRAHEDRON, 1997, 53 (46) :15813-15826
[12]   Naturally occurring proline analogues [J].
Mauger, AB .
JOURNAL OF NATURAL PRODUCTS, 1996, 59 (12) :1205-1211
[13]   REACTION OF O-METHYL-N,N'-DIISOPROPYLISOUREA WITH AMINO-ACIDS AND AMINES [J].
MUSICH, JA ;
RAPOPORT, H .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (01) :139-141
[14]   Quorum sensing inhibition: Targeting chemical communication in Gram-negative bacteria [J].
Persson, T ;
Givskov, M ;
Nielsen, J .
CURRENT MEDICINAL CHEMISTRY, 2005, 12 (26) :3103-3115
[15]   How Delisea pulchra furanones affect quorum sensing and swarming motility in Serratia liquefaciens MG1 [J].
Rasmussen, TB ;
Manefield, M ;
Andersen, JB ;
Eberl, L ;
Anthoni, U ;
Christophersen, C ;
Steinberg, P ;
Kjelleberg, S ;
Givskov, M .
MICROBIOLOGY-UK, 2000, 146 :3237-3244
[16]   Crystal structure and chirality of natural floridoside [J].
Simon-Colin, C ;
Michaud, F ;
Léger, JM ;
Deslandes, E .
CARBOHYDRATE RESEARCH, 2003, 338 (22) :2413-2416
[17]   Quorum-sensing signals indicate that cystic fibrosis lungs are infected with bacterial biofilms [J].
Singh, PK ;
Schaefer, AL ;
Parsek, MR ;
Moninger, TO ;
Welsh, MJ ;
Greenberg, EP .
NATURE, 2000, 407 (6805) :762-764
[18]   Chemical defenses of seaweeds against microbial colonization [J].
Steinberg, PD ;
Schneider, R ;
Kjelleberg, S .
BIODEGRADATION, 1997, 8 (03) :211-220
[19]   Detection of quorum-sensing N-acyl homoserine lactone signal molecules by bacterial biosensors [J].
Steindler, Laura ;
Venturi, Vittorio .
FEMS MICROBIOLOGY LETTERS, 2007, 266 (01) :1-9
[20]   Induction of settlement of larvae of the sea urchin Holopneustes purpurascens by histamine from a host alga [J].
Swanson, RL ;
Williamson, JE ;
De Nys, R ;
Kumar, N ;
Bucknall, MP ;
Steinberg, PD .
BIOLOGICAL BULLETIN, 2004, 206 (03) :161-172