A new cytotoxic tambjamine alkaloid from the Azorean nudibranch Tambja ceutae

被引:42
作者
Carbone, Marianna [1 ]
Irace, Carlo [2 ]
Costagliola, Francesca [1 ]
Castelluccio, Francesco [1 ]
Villani, Guido [1 ]
Calado, Goncalo [3 ]
Padula, Vinicius [4 ]
Cimino, Guido [1 ]
Cervera, J. Lucas [5 ]
Santamaria, Rita [2 ]
Gavagnin, Margherita [1 ]
机构
[1] CNR, Ist Chim Biomol, I-80078 Pozzuoli, Na, Italy
[2] Univ Naples Federico 2, Fac Farm, Dipartimento Farmacol Sperimentale, Naples, Italy
[3] Univ Lusofona Humanidades & Tecnol, P-1749024 Lisbon, Portugal
[4] Univ Fed Rio de Janeiro, Dept Invertebrados, Museo Nacl, BR-20940040 Rio De Janeiro, Brazil
[5] Univ Cadiz, Dept Biol, Fac Ciencias Mar & Ambientales, Cadiz 11510, Spain
关键词
Marine natural products; Bromopyrrole alkaloids; Spectroscopic methods; Cytotoxic activity; MARINE OPISTHOBRANCH MOLLUSKS; BRYOZOAN BUGULA-DENTATA; METABOLITES; BE-18591; PIGMENT;
D O I
10.1016/j.bmcl.2010.02.020
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The chemical investigation of Azorean nudibranch mollusk Tambja ceutae led us to isolate a new member of the tambjamine family, tambjamine K (1). The bryozoan Bugula dentata, prey of the nudibranch, was also analyzed and found to contain compound 1 in very small amounts together with known blue pigment 2 and tambjamines A (3) and B (4). The structure of tambjamine 1 was elucidated by the interpretation of the spectroscopic data as well as by the comparison with related compounds. Compounds 1 and 2 possess antiproliferative activity, in particular, tambjamine K (1) displayed high cytotoxicity against both tumor and non-tumor mammalian cells. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2668 / 2670
页数:3
相关论文
共 18 条
[1]   NEW TAMBJAMINE ALKALOIDS FROM THE MARINE BRYOZOAN BUGULA-DENTATA [J].
BLACKMAN, AJ ;
LI, CP .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1994, 47 (08) :1625-1629
[2]   Further syphonosides from the sea hare Syphonota geographica and the sea-grass Halophila stipulacea [J].
Carbone, Marianna ;
Gavagnin, Margherita ;
Mollo, Ernesto ;
Bidello, Margherita ;
Roussis, Vassilios ;
Cimino, Guido .
TETRAHEDRON, 2008, 64 (01) :191-196
[3]   ROLE OF SECONDARY METABOLITES IN FEEDING ASSOCIATIONS BETWEEN A PREDATORY NUDIBRANCH, 2 GRAZING NUDIBRANCHS, AND A BRYOZOAN [J].
CARTE, B ;
FAULKNER, DJ .
JOURNAL OF CHEMICAL ECOLOGY, 1986, 12 (03) :795-804
[4]   DEFENSIVE METABOLITES FROM 3 NEMBROTHID NUDIBRANCHS [J].
CARTE, B ;
FAULKNER, DJ .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (14) :2314-2318
[5]   Cytotoxic and genotoxic effects of tambjamine D, an alkaloid isolated from the nudibranch Tambja eliora, on Chinese hamster lung fibroblasts [J].
Cavalcanti, Bruno C. ;
Junior, Helio V. N. ;
Seleghim, Mirna H. R. ;
Berlinck, Roberto G. S. ;
Cunha, Geanne M. A. ;
Moraes, Manoel O. ;
Pessoa, Claudia .
CHEMICO-BIOLOGICAL INTERACTIONS, 2008, 174 (03) :155-162
[6]  
Cimino G, 2001, BIOACTIVE COMPOUNDS FROM NATURAL SOURCES: ISOLATION CHARACTERISATION AND BIOLOGICAL PROPERTIES, P577
[7]  
Cimino G, 1999, CURR ORG CHEM, V3, P327
[8]  
CIMINO G, 2001, Patent No. 20011
[9]   A new antitumor isoquinoline alkaloid from the marine nudibranch Jorunna funebris [J].
Fontana, A ;
Cavaliere, P ;
Wahidulla, S ;
Naik, CG ;
Cimino, G .
TETRAHEDRON, 2000, 56 (37) :7305-7308
[10]   Isolation and structure elucidation of a novel yellow pigment from the marine bacterium Pseudoalteromonas tunicata [J].
Franks, A ;
Haywood, P ;
Holmström, C ;
Egan, S ;
Kjelleberg, S ;
Kumar, N .
MOLECULES, 2005, 10 (10) :1286-1291