Ianthelliformisamines A-C, Antibacterial Bromotyrosine-Derived Metabolites from the Marine Sponge Suberea ianthelliformis

被引:38
|
作者
Xu, Min [1 ]
Davis, Rohan A. [1 ]
Feng, Yunjiang [1 ]
Sykes, Melissa L. [1 ]
Shelper, Todd [1 ]
Avery, Vicky M. [1 ]
Camp, David [1 ]
Quinn, Ronald J. [1 ]
机构
[1] Griffith Univ, Eskitis Inst, Brisbane, Qld 4111, Australia
来源
JOURNAL OF NATURAL PRODUCTS | 2012年 / 75卷 / 05期
基金
澳大利亚研究理事会;
关键词
MULTIDRUG-RESISTANCE; MECHANISMS; DERIVATIVES; ALKALOIDS;
D O I
10.1021/np300147d
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
A high-throughput screening campaign using a prefractionated natural product library and an in vitro Pseudomonas aeruginosa (PAO200 strain) assay identified two antibacterial fractions derived from the marine sponge Suberea ianthelliformis. Mass-directed isolation of the CH2Cl2/CH3OH extract from S. ianthelliformis resulted in the purification of three new bromotyrosine-derived metabolites, ianthelliformisamines A-C (1-3), together with the known natural products aplysamine 1 (4) and araplysillin I (5). The structures of 1-3 were determined following analysis of 1D and 2D NMR and MS spectroscopic data. This is the first report of chemistry from the marine sponge S. ianthelliformis. Ianthelliformisamine A (1) showed inhibitory activity against the Gram-negative bacterium P. aeruginosa with an IC50 value of 6.8 mu M (MIC = 35 mu M).
引用
收藏
页码:1001 / 1005
页数:5
相关论文
共 50 条
  • [31] Aplysinopsin-type and Bromotyrosine-derived Alkaloids from the South China Sea Sponge Fascaplysinopsis reticulata
    Qi Wang
    Xu-Li Tang
    Xiang-Chao Luo
    Nicole J. de Voog
    Ping-Lin Li
    Guo-Qiang Li
    Scientific Reports, 9
  • [32] Dereplication of Bromotyrosine-derived Metabolites by LC-PDA-MS and Analysis of the Chemical Profile of 14 Aplysina Sponge Specimens from the Brazilian Coastline
    Silva, Michelli M.
    Bergamasco, Juliana
    Lira, Simone P.
    Lopes, Norberto P.
    Hajdu, Eduardo
    Peixinho, Solange
    Berlinck, Roberto G. S.
    AUSTRALIAN JOURNAL OF CHEMISTRY, 2010, 63 (06) : 886 - 894
  • [33] Ianthesine E, a new bromotyrosine-derived metabolite from the Great Barrier Reef sponge Pseudoceratina sp.
    Kalaitzis, John A.
    Leone, Priscila De Almeida
    Hooper, John N. A.
    Quinn, Ronald J.
    NATURAL PRODUCT RESEARCH, 2008, 22 (14) : 1263 - 1269
  • [34] 11,17-dideoxyagelorin A and B, new bromotyrosine derivatives and analogs from the marine sponge Suberea aff. praetensa
    Kijjoa, A
    Watanadilok, R
    Sonchaeng, P
    Silva, AMS
    Eaton, G
    Herz, W
    ZEITSCHRIFT FUR NATURFORSCHUNG C-A JOURNAL OF BIOSCIENCES, 2001, 56 (11-12): : 1116 - 1119
  • [35] Ma'edamines C and D, New Bromotyrosine Alkaloids Possessing a Unique Tetrasubstituted Pyridinium Moiety from an Okinawan Marine Sponge Suberea sp.
    Kurimoto, Shin-ichiro
    Seino, Satsuki
    Fromont, Jane
    Kobayashi, Jun'ichi
    Kubota, Takaaki
    ORGANIC LETTERS, 2019, 21 (21) : 8824 - 8826
  • [36] Cyclotheonazoles A-C, Three Novel Metabolites from Marine Sponge Theonella sp.
    Issac, A.
    Aknin, M.
    Gauvin-Bialecki, A.
    Kashman, Y.
    Carmeli, S.
    PLANTA MEDICA, 2013, 79 (10) : 887 - 887
  • [37] Asmarines A-C; Three novel cytotoxic metabolites from the marine sponge Raspailia sp.
    Yosief, T.
    Rudi, A.
    Stein, Z.
    Goldberg, I.
    Tetrahedron Letters, 39 (20):
  • [38] Asmarines A-C;: Three novel cytotoxic metabolites from the marine sponge Raspailia sp.
    Yosief, T
    Rudi, A
    Stein, Z
    Goldberg, I
    Gravalos, GMD
    Schleyer, M
    Kashman, Y
    TETRAHEDRON LETTERS, 1998, 39 (20) : 3323 - 3326
  • [39] Pseudoceramines A-D, new antibacterial bromotyrosine alkaloids from the marine sponge Pseudoceratina sp.
    Yin, Sheng
    Davis, Rohan A.
    Shelper, Todd
    Sykes, Melissa L.
    Avery, Vicky M.
    Elofsson, Mikael
    Sundin, Charlotta
    Quinn, Ronald J.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (19) : 6755 - 6760
  • [40] Cultures of the Marine Bacterium Pseudovibrio denitrificans Ab134 Produce Bromotyrosine-Derived Alkaloids Previously Only Isolated from Marine Sponges
    Nicacio, Karen J.
    Ioca, Laura P.
    Froes, Adriana M.
    Leomil, Luciana
    Appolinario, Luciana R.
    Thompson, Christiane C.
    Thompson, Fabiano L.
    Ferreira, Antonio G.
    Williams, David E.
    Andersen, Raymond J.
    Eustaquio, Alessandra S.
    Berlinck, Roberto G. S.
    JOURNAL OF NATURAL PRODUCTS, 2017, 80 (02): : 235 - 240